3-Phenyl-2-(2,4,5-tricyano­phenyl­meth­yl)-1H-indene

In the title compound, C₂₅H₁₅N₃, the indene unit is essentially planar and there are inter­molecular C—H...π inter­actions in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.046
• wR factor = 0.110
• Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C18    -   C23    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C20    -   C24    ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C21    -   C25    ...       1.44 Ang.
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........        CGA

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.99
           From the CIF: _reflns_number_total               2160
           Count of symmetry unique reflns         2167
           Completeness (_total/calc)             99.68%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
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
   5 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

3-phenyl-2-(2,4,5-tricyanophenylmethyl)-1H-indene

Crystal data

C25H15N3	Dx = 1.245 Mg m^−3
Mr = 357.40	Melting point: 492.2 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 7.7190 (15) Å	θ = 10–13°
b = 10.155 (2) Å	µ = 0.08 mm^−1
c = 24.316 (5) Å	T = 293 K
V = 1906.0 (7) Å^3	Block, colourless
Z = 4	0.45 × 0.33 × 0.30 mm
F(000) = 744

Data collection

Enraf–Nonius CAD-4 diffractometer	1385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
Graphite monochromator	θmax = 26.0°, θmin = 1.7°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	k = 0→12
Tmin = 0.951, Tmax = 0.978	l = −28→28
4216 measured reflections	3 standard reflections every 200 reflections
2160 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.046	w = 1/[σ^2(Fo^2) + (0.02P)^2 + 0.765P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.110	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.16 e Å^−3
2160 reflections	Δρmin = −0.19 e Å^−3
254 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0339 (16)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.03 (7)

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.

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.0743 (5)	0.8086 (4)	0.22777 (16)	0.0824 (12)
N2	0.4430 (7)	0.7926 (5)	−0.03022 (17)	0.1095 (17)
N3	0.5180 (6)	1.1831 (4)	−0.02033 (15)	0.0938 (15)
C1	0.4459 (7)	1.0300 (4)	0.39588 (17)	0.0684 (13)
H1	0.3544	1.0363	0.4206	0.082*
C2	0.6125 (8)	0.9983 (5)	0.41403 (18)	0.0769 (15)
H2	0.6316	0.9833	0.4513	0.092*
C3	0.7482 (7)	0.9888 (4)	0.37788 (18)	0.0677 (13)
H3	0.8577	0.9671	0.3909	0.081*
C4	0.7247 (6)	1.0110 (4)	0.32259 (18)	0.0579 (11)
H4	0.8174	1.0048	0.2983	0.069*
C5	0.5596 (5)	1.0429 (3)	0.30361 (15)	0.0481 (10)
C6	0.4200 (6)	1.0520 (4)	0.34040 (15)	0.0529 (10)
C7	0.2588 (5)	1.0851 (4)	0.30774 (15)	0.0541 (10)
H7A	0.1732	1.0156	0.3107	0.065*
H7B	0.2079	1.1671	0.3203	0.065*
C8	0.3234 (5)	1.0976 (3)	0.24975 (15)	0.0446 (9)
C9	0.4968 (5)	1.0730 (3)	0.24788 (16)	0.0444 (8)
C10	0.6120 (5)	1.0727 (4)	0.19880 (14)	0.0456 (9)
C11	0.6673 (6)	1.1903 (4)	0.17595 (17)	0.0612 (12)
H11	0.6364	1.2699	0.1921	0.073*
C12	0.7704 (6)	1.1892 (5)	0.12828 (19)	0.0725 (14)
H12	0.8086	1.2682	0.1132	0.087*
C13	0.8152 (5)	1.0720 (6)	0.10386 (18)	0.0723 (13)
H13	0.8810	1.0715	0.0718	0.087*
C14	0.7618 (6)	0.9554 (5)	0.12724 (18)	0.0679 (13)
H14	0.7928	0.8759	0.1111	0.081*
C15	0.6623 (5)	0.9556 (4)	0.17470 (16)	0.0557 (11)
H15	0.6290	0.8761	0.1905	0.067*
C16	0.2065 (5)	1.1322 (4)	0.20264 (14)	0.0497 (10)
H16A	0.0879	1.1122	0.2129	0.060*
H16B	0.2137	1.2263	0.1961	0.060*
C17	0.2482 (4)	1.0613 (3)	0.15028 (14)	0.0399 (8)
C18	0.2205 (4)	0.9252 (4)	0.14570 (15)	0.0442 (9)
C19	0.2674 (5)	0.8551 (4)	0.09917 (16)	0.0536 (10)
H19	0.2474	0.7649	0.0973	0.064*
C20	0.3441 (5)	0.9197 (4)	0.05554 (15)	0.0507 (10)
C21	0.3692 (5)	1.0569 (4)	0.05858 (14)	0.0485 (10)
C22	0.3197 (5)	1.1240 (4)	0.10516 (15)	0.0469 (10)
H22	0.3348	1.2148	0.1063	0.056*
C23	0.1412 (5)	0.8577 (4)	0.19115 (17)	0.0549 (10)
C24	0.3993 (7)	0.8481 (5)	0.00780 (18)	0.0719 (14)
C25	0.4516 (6)	1.1270 (4)	0.01433 (16)	0.0642 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.066 (2)	0.093 (3)	0.088 (3)	−0.015 (2)	0.006 (2)	0.029 (2)
N2	0.110 (4)	0.124 (4)	0.095 (3)	0.004 (4)	0.013 (3)	−0.048 (3)
N3	0.102 (3)	0.113 (3)	0.067 (3)	0.015 (3)	0.024 (3)	0.028 (2)
C1	0.090 (3)	0.062 (3)	0.053 (3)	−0.002 (3)	0.009 (3)	−0.002 (2)
C2	0.111 (4)	0.064 (3)	0.056 (3)	−0.004 (3)	−0.020 (3)	0.005 (2)
C3	0.076 (3)	0.056 (3)	0.071 (3)	−0.001 (3)	−0.015 (3)	0.007 (2)
C4	0.055 (3)	0.053 (2)	0.066 (3)	−0.004 (2)	−0.009 (2)	0.005 (2)
C5	0.056 (2)	0.037 (2)	0.051 (2)	−0.0029 (19)	0.001 (2)	0.0001 (17)
C6	0.064 (3)	0.045 (2)	0.050 (2)	−0.004 (2)	0.005 (2)	−0.0042 (18)
C7	0.054 (2)	0.052 (2)	0.056 (2)	0.003 (2)	0.010 (2)	−0.004 (2)
C8	0.042 (2)	0.045 (2)	0.047 (2)	0.0007 (18)	0.0061 (18)	−0.0018 (18)
C9	0.0461 (19)	0.0405 (19)	0.0465 (19)	−0.0022 (19)	0.0027 (17)	0.0000 (19)
C10	0.0348 (19)	0.055 (2)	0.047 (2)	−0.0002 (19)	0.0005 (17)	0.003 (2)
C11	0.054 (3)	0.062 (3)	0.068 (3)	−0.008 (2)	0.007 (2)	0.006 (2)
C12	0.054 (3)	0.095 (4)	0.068 (3)	−0.016 (3)	0.009 (3)	0.016 (3)
C13	0.039 (2)	0.122 (4)	0.056 (3)	0.007 (3)	0.009 (2)	0.012 (3)
C14	0.052 (3)	0.088 (4)	0.064 (3)	0.027 (3)	0.005 (2)	−0.004 (3)
C15	0.047 (2)	0.060 (3)	0.060 (3)	0.009 (2)	0.006 (2)	0.003 (2)
C16	0.041 (2)	0.050 (2)	0.058 (2)	0.0107 (19)	0.0057 (19)	0.0014 (19)
C17	0.0262 (17)	0.049 (2)	0.045 (2)	0.0067 (18)	−0.0008 (16)	0.0021 (17)
C18	0.0288 (17)	0.047 (2)	0.057 (2)	−0.0024 (19)	−0.0018 (16)	0.0045 (19)
C19	0.044 (2)	0.047 (2)	0.070 (3)	−0.0027 (19)	−0.007 (2)	−0.007 (2)
C20	0.043 (2)	0.058 (2)	0.051 (2)	0.006 (2)	−0.0043 (19)	−0.007 (2)
C21	0.041 (2)	0.063 (3)	0.042 (2)	0.008 (2)	−0.0023 (18)	0.0044 (19)
C22	0.043 (2)	0.043 (2)	0.055 (2)	0.0043 (18)	−0.004 (2)	0.0026 (19)
C23	0.044 (2)	0.056 (2)	0.065 (3)	−0.004 (2)	−0.002 (2)	0.008 (2)
C24	0.068 (3)	0.082 (3)	0.066 (3)	0.006 (3)	−0.002 (3)	−0.024 (3)
C25	0.067 (3)	0.076 (3)	0.049 (2)	0.018 (3)	0.006 (2)	0.008 (2)

Geometric parameters (Å, º)

N1—C23	1.144 (5)	C11—C12	1.406 (5)
N2—C24	1.134 (5)	C11—H11	0.9300
N3—C25	1.139 (5)	C12—C13	1.374 (6)
C1—C6	1.382 (5)	C12—H12	0.9300
C1—C2	1.397 (7)	C13—C14	1.376 (6)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.371 (7)	C14—C15	1.386 (5)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.375 (5)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.498 (5)
C4—C5	1.394 (6)	C16—H16A	0.9700
C4—H4	0.9300	C16—H16B	0.9700
C5—C6	1.403 (5)	C17—C22	1.383 (5)
C5—C9	1.471 (5)	C17—C18	1.404 (5)
C6—C7	1.514 (5)	C18—C19	1.385 (5)
C7—C8	1.501 (5)	C18—C23	1.437 (5)
C7—H7A	0.9700	C19—C20	1.381 (5)
C7—H7B	0.9700	C19—H19	0.9300
C8—C9	1.362 (5)	C20—C21	1.408 (5)
C8—C16	1.500 (5)	C20—C24	1.435 (5)
C9—C10	1.488 (5)	C21—C22	1.376 (5)
C10—C15	1.382 (5)	C21—C25	1.439 (5)
C10—C11	1.385 (5)	C22—H22	0.9300
C6—C1—C2	118.6 (4)	C11—C12—H12	119.8
C6—C1—H1	120.7	C12—C13—C14	119.4 (4)
C2—C1—H1	120.7	C12—C13—H13	120.3
C3—C2—C1	121.1 (4)	C14—C13—H13	120.3
C3—C2—H2	119.4	C13—C14—C15	120.6 (5)
C1—C2—H2	119.4	C13—C14—H14	119.7
C2—C3—C4	121.0 (5)	C15—C14—H14	119.7
C2—C3—H3	119.5	C10—C15—C14	120.7 (4)
C4—C3—H3	119.5	C10—C15—H15	119.7
C3—C4—C5	118.8 (4)	C14—C15—H15	119.7
C3—C4—H4	120.6	C17—C16—C8	114.0 (3)
C5—C4—H4	120.6	C17—C16—H16A	108.8
C4—C5—C6	120.4 (4)	C8—C16—H16A	108.8
C4—C5—C9	130.9 (4)	C17—C16—H16B	108.8
C6—C5—C9	108.7 (3)	C8—C16—H16B	108.8
C1—C6—C5	120.0 (4)	H16A—C16—H16B	107.6
C1—C6—C7	131.8 (4)	C22—C17—C18	116.8 (3)
C5—C6—C7	108.1 (3)	C22—C17—C16	122.6 (3)
C8—C7—C6	103.8 (3)	C18—C17—C16	120.5 (3)
C8—C7—H7A	111.0	C19—C18—C17	122.1 (4)
C6—C7—H7A	111.0	C19—C18—C23	119.6 (3)
C8—C7—H7B	111.0	C17—C18—C23	118.3 (3)
C6—C7—H7B	111.0	C20—C19—C18	119.7 (3)
H7A—C7—H7B	109.0	C20—C19—H19	120.1
C9—C8—C16	127.5 (4)	C18—C19—H19	120.1
C9—C8—C7	110.0 (4)	C19—C20—C21	119.2 (3)
C16—C8—C7	122.5 (3)	C19—C20—C24	120.5 (4)
C8—C9—C5	109.3 (4)	C21—C20—C24	120.2 (4)
C8—C9—C10	127.9 (4)	C22—C21—C20	119.7 (4)
C5—C9—C10	122.8 (3)	C22—C21—C25	119.6 (4)
C15—C10—C11	119.1 (3)	C20—C21—C25	120.7 (4)
C15—C10—C9	120.6 (3)	C21—C22—C17	122.4 (3)
C11—C10—C9	120.3 (4)	C21—C22—H22	118.8
C10—C11—C12	119.9 (4)	C17—C22—H22	118.8
C10—C11—H11	120.1	N1—C23—C18	177.2 (5)
C12—C11—H11	120.1	N2—C24—C20	179.3 (6)
C13—C12—C11	120.4 (4)	N3—C25—C21	179.3 (5)
C13—C12—H12	119.8
C6—C1—C2—C3	0.0 (7)	C9—C10—C11—C12	−177.5 (4)
C1—C2—C3—C4	0.3 (7)	C10—C11—C12—C13	0.7 (6)
C2—C3—C4—C5	−0.3 (7)	C11—C12—C13—C14	−1.6 (7)
C3—C4—C5—C6	−0.1 (6)	C12—C13—C14—C15	0.6 (7)
C3—C4—C5—C9	179.1 (4)	C11—C10—C15—C14	−2.2 (6)
C2—C1—C6—C5	−0.3 (6)	C9—C10—C15—C14	176.5 (3)
C2—C1—C6—C7	178.8 (4)	C13—C14—C15—C10	1.3 (7)
C4—C5—C6—C1	0.4 (6)	C9—C8—C16—C17	37.4 (5)
C9—C5—C6—C1	−179.0 (3)	C7—C8—C16—C17	−142.5 (4)
C4—C5—C6—C7	−178.9 (4)	C8—C16—C17—C22	−109.3 (4)
C9—C5—C6—C7	1.7 (4)	C8—C16—C17—C18	68.7 (4)
C1—C6—C7—C8	179.1 (4)	C22—C17—C18—C19	2.2 (5)
C5—C6—C7—C8	−1.7 (4)	C16—C17—C18—C19	−176.0 (3)
C6—C7—C8—C9	1.1 (4)	C22—C17—C18—C23	−178.0 (3)
C6—C7—C8—C16	−179.0 (3)	C16—C17—C18—C23	3.9 (5)
C16—C8—C9—C5	−179.9 (3)	C17—C18—C19—C20	0.0 (6)
C7—C8—C9—C5	0.0 (5)	C23—C18—C19—C20	−179.8 (4)
C16—C8—C9—C10	−0.8 (7)	C18—C19—C20—C21	−1.7 (6)
C7—C8—C9—C10	179.1 (3)	C18—C19—C20—C24	177.8 (4)
C4—C5—C9—C8	179.7 (4)	C19—C20—C21—C22	1.1 (6)
C6—C5—C9—C8	−1.1 (4)	C24—C20—C21—C22	−178.4 (4)
C4—C5—C9—C10	0.5 (6)	C19—C20—C21—C25	178.8 (4)
C6—C5—C9—C10	179.7 (3)	C24—C20—C21—C25	−0.6 (6)
C8—C9—C10—C15	−101.5 (5)	C20—C21—C22—C17	1.3 (6)
C5—C9—C10—C15	77.5 (5)	C25—C21—C22—C17	−176.5 (4)
C8—C9—C10—C11	77.2 (5)	C18—C17—C22—C21	−2.8 (5)
C5—C9—C10—C11	−103.9 (4)	C16—C17—C22—C21	175.3 (3)
C15—C10—C11—C12	1.2 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···CgA^i	0.93	2.99	3.724 (4)	137

Symmetry code: (i) −x+1, y−1/2, −z+1/2.