2-[3-Dicyano­methyl­ene-2-(3-methoxy­benzyl­idene)indan-1-yl­idene]malononitrile

The title compound, C₂₃H₁₂N₄O, has potential application in non-linear optics; it has a chiral crystal structure despite the lack of a stereogenic centre. The crystal structure involves two intermolecular C—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.031
• wR factor = 0.065
• Data-to-parameter ratio = 7.4

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.130
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.37
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C20    -   C22     ..       5.42 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C20    -   C21    ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C20    -   C22    ...       1.42 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C50    -   C51    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C50    -   C52    ...       1.43 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16    ..  N22     ..       2.73 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8     ..  N21     ..       2.64 Ang.

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           25.00
           From the CIF: _reflns_number_total               1873
           Count of symmetry unique reflns         1886
           Completeness (_total/calc)             99.31%
           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

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

   1 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
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON and WinGX (Farrugia, 1999).

2-[3-Dicyanomethylene-2-(3-methoxybenzylidene)indan-1-ylidene]malononitrile

Crystal data

C23H12N4O	F(000) = 744
Mr = 360.37	Dx = 1.319 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 16.023 (7) Å	θ = 12.7–14.5°
b = 20.624 (5) Å	µ = 0.08 mm^−1
c = 5.493 (8) Å	T = 293 K
V = 1815 (3) Å^3	Needle, orange
Z = 4	0.5 × 0.1 × 0.1 mm

Data collection

Rigaku AFC-5S diffractometer	θmax = 25°, θmin = 3.2°
Graphite monochromator	h = −19→19
ω scans	k = −6→24
8817 measured reflections	l = −6→6
1873 independent reflections	3 standard reflections every 150 reflections
962 reflections with I > 2σ(I)	intensity decay: 0.7%
Rint = 0.130

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.031	[exp{5(sinθ/λ)^2}]/[σ^2(Fo^2) + (0.01P)^2] where P = 0.33333Fo^2 + 0.66667Fc^2
wR(F^2) = 0.065	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.10 e Å^−3
1873 reflections	Δρmin = −0.15 e Å^−3
254 parameters

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
O12	0.47073 (12)	−0.03265 (10)	1.4997 (4)	0.0577 (6)
N21	0.71262 (16)	0.23941 (16)	0.9065 (6)	0.0811 (10)
N22	0.63851 (16)	0.11142 (14)	1.4656 (6)	0.0662 (8)
N51	0.16714 (16)	0.14447 (16)	0.7009 (5)	0.0743 (9)
N52	0.26308 (16)	0.04338 (16)	1.3240 (6)	0.0729 (9)
C1	0.45671 (15)	0.10595 (13)	1.0052 (5)	0.0403 (7)
C2	0.52195 (15)	0.15360 (13)	0.9374 (5)	0.0404 (7)
C3	0.48845 (16)	0.19343 (14)	0.7412 (5)	0.0410 (7)
C4	0.40294 (16)	0.17737 (15)	0.7043 (5)	0.0425 (7)
C5	0.37832 (16)	0.12854 (14)	0.8841 (5)	0.0417 (7)
C6	0.52466 (18)	0.24247 (15)	0.6028 (5)	0.0494 (8)
H6	0.5798	0.2546	0.6303	0.059*
C7	0.47857 (19)	0.27289 (15)	0.4250 (6)	0.0603 (9)
H7	0.5028	0.3054	0.3314	0.072*
C8	0.39593 (19)	0.25531 (17)	0.3843 (6)	0.0643 (9)
H8	0.366	0.2757	0.2611	0.077*
C9	0.35732 (17)	0.20814 (14)	0.5235 (6)	0.0536 (8)
H9	0.3018	0.1973	0.4963	0.064*
C10	0.46473 (16)	0.04674 (15)	1.1060 (5)	0.0479 (8)
H10	0.4147	0.0274	1.1515	0.057*
C11	0.53922 (15)	0.00764 (14)	1.1558 (5)	0.0422 (7)
C12	0.53899 (16)	−0.03583 (15)	1.3485 (5)	0.0439 (7)
C13	0.60584 (17)	−0.07807 (16)	1.3847 (6)	0.0513 (8)
H13	0.6055	−0.1071	1.5143	0.062*
C14	0.67214 (18)	−0.07632 (16)	1.2269 (6)	0.0569 (8)
H14	0.7173	−0.1039	1.2523	0.068*
C15	0.67308 (17)	−0.03454 (14)	1.0316 (6)	0.0535 (8)
H15	0.7181	−0.0346	0.9247	0.064*
C16	0.60744 (16)	0.00735 (13)	0.9945 (5)	0.0460 (7)
H16	0.6082	0.0355	0.8623	0.055*
C20	0.59639 (15)	0.16271 (14)	1.0572 (5)	0.0434 (7)
C21	0.65937 (18)	0.20652 (16)	0.9716 (6)	0.0544 (8)
C22	0.61838 (16)	0.13192 (16)	1.2798 (7)	0.0509 (8)
C50	0.29919 (16)	0.11060 (14)	0.9425 (5)	0.0446 (8)
C51	0.22689 (17)	0.12992 (17)	0.8039 (6)	0.0519 (9)
C52	0.27968 (16)	0.07206 (16)	1.1523 (7)	0.0504 (8)
C120	0.45753 (19)	−0.08533 (17)	1.6662 (6)	0.0646 (9)
H122	0.4515	−0.125	1.5766	0.097*
H123	0.4078	−0.0775	1.7593	0.097*
H121	0.5044	−0.0887	1.7742	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O12	0.0523 (11)	0.0593 (13)	0.0616 (13)	0.0038 (12)	0.0082 (11)	0.0157 (13)
N21	0.0595 (16)	0.085 (2)	0.099 (2)	−0.025 (2)	0.0084 (18)	−0.007 (2)
N22	0.0630 (15)	0.0738 (19)	0.0617 (18)	0.0163 (17)	−0.0146 (14)	−0.0088 (18)
N51	0.0478 (13)	0.090 (2)	0.085 (2)	0.0048 (18)	−0.0089 (15)	0.0034 (19)
N52	0.0734 (18)	0.077 (2)	0.069 (2)	−0.0004 (19)	0.0142 (16)	0.009 (2)
C1	0.0358 (14)	0.0399 (16)	0.0451 (17)	0.0032 (14)	−0.0001 (14)	0.0037 (16)
C2	0.0374 (14)	0.0354 (16)	0.0483 (18)	0.0060 (15)	0.0002 (13)	−0.0049 (15)
C3	0.0383 (15)	0.0337 (15)	0.0509 (18)	0.0026 (15)	−0.0018 (13)	−0.0034 (16)
C4	0.0400 (14)	0.0398 (17)	0.0477 (17)	0.0024 (16)	−0.0015 (14)	0.0004 (16)
C5	0.0407 (14)	0.0373 (16)	0.0472 (16)	0.0024 (15)	−0.0006 (13)	−0.0010 (14)
C6	0.0399 (14)	0.0472 (18)	0.061 (2)	0.0002 (17)	0.0006 (15)	0.0036 (18)
C7	0.0584 (18)	0.050 (2)	0.072 (2)	0.0019 (19)	0.0073 (18)	0.0124 (19)
C8	0.0580 (19)	0.062 (2)	0.073 (2)	0.004 (2)	−0.0118 (18)	0.015 (2)
C9	0.0419 (16)	0.0488 (18)	0.070 (2)	0.0007 (16)	−0.0060 (15)	0.010 (2)
C10	0.0429 (16)	0.0479 (19)	0.0529 (17)	−0.0006 (17)	0.0052 (13)	0.0043 (17)
C11	0.0419 (15)	0.0355 (16)	0.0493 (18)	0.0015 (15)	−0.0023 (14)	0.0018 (15)
C12	0.0426 (16)	0.0396 (17)	0.0496 (17)	−0.0015 (16)	−0.0025 (15)	−0.0041 (16)
C13	0.0532 (17)	0.0419 (17)	0.0589 (18)	0.0025 (18)	−0.0050 (17)	0.0055 (16)
C14	0.0462 (17)	0.0467 (19)	0.078 (2)	0.0096 (18)	−0.0051 (18)	0.000 (2)
C15	0.0477 (16)	0.0444 (17)	0.068 (2)	0.0042 (17)	0.0050 (16)	−0.0035 (19)
C16	0.0480 (16)	0.0385 (16)	0.0514 (17)	−0.0003 (16)	0.0024 (14)	0.0020 (17)
C20	0.0381 (14)	0.0416 (17)	0.0505 (18)	0.0068 (15)	0.0007 (14)	−0.0031 (16)
C21	0.0466 (17)	0.055 (2)	0.062 (2)	0.0016 (18)	−0.0023 (17)	−0.0133 (19)
C22	0.0406 (16)	0.054 (2)	0.058 (2)	0.0041 (17)	−0.0059 (16)	−0.0130 (19)
C50	0.0400 (15)	0.0443 (18)	0.0496 (19)	−0.0005 (16)	−0.0006 (13)	−0.0005 (16)
C51	0.0432 (16)	0.055 (2)	0.057 (2)	0.0008 (17)	0.0007 (15)	0.0013 (18)
C52	0.0392 (16)	0.053 (2)	0.059 (2)	−0.0014 (17)	0.0049 (15)	−0.007 (2)
C120	0.0628 (19)	0.072 (2)	0.059 (2)	−0.018 (2)	0.0004 (18)	0.0121 (19)

Geometric parameters (Å, º)

O12—C12	1.375 (3)	C8—H8	0.93
O12—C120	1.436 (4)	C9—H9	0.93
N21—C21	1.147 (4)	C10—C11	1.466 (4)
N22—C22	1.151 (4)	C10—H10	0.93
N51—C51	1.152 (4)	C11—C12	1.387 (4)
N52—C52	1.145 (4)	C11—C16	1.407 (4)
C1—C10	1.347 (4)	C12—C13	1.395 (4)
C1—C2	1.482 (4)	C13—C14	1.372 (4)
C1—C5	1.496 (4)	C13—H13	0.93
C2—C20	1.375 (4)	C14—C15	1.376 (4)
C2—C3	1.458 (4)	C14—H14	0.93
C3—C6	1.392 (4)	C15—C16	1.376 (3)
C3—C4	1.424 (3)	C15—H15	0.93
C4—C9	1.387 (4)	C16—H16	0.93
C4—C5	1.464 (4)	C20—C22	1.422 (5)
C5—C50	1.359 (3)	C20—C21	1.434 (4)
C6—C7	1.376 (4)	C50—C52	1.434 (5)
C6—H6	0.93	C50—C51	1.442 (4)
C7—C8	1.391 (4)	C120—H122	0.96
C7—H7	0.93	C120—H123	0.96
C8—C9	1.383 (4)	C120—H121	0.96
N52···C52^i	3.064 (7)	N52···C51^ii	3.236 (7)
C12—O12—C120	117.8 (2)	C16—C11—C10	121.1 (3)
C10—C1—C2	129.6 (2)	O12—C12—C11	115.6 (3)
C10—C1—C5	123.0 (3)	O12—C12—C13	123.7 (3)
C2—C1—C5	105.9 (2)	C11—C12—C13	120.7 (3)
C20—C2—C3	126.6 (3)	C14—C13—C12	119.2 (3)
C20—C2—C1	125.6 (3)	C14—C13—H13	120.4
C3—C2—C1	107.4 (2)	C12—C13—H13	120.4
C6—C3—C4	119.5 (3)	C13—C14—C15	121.2 (3)
C6—C3—C2	131.3 (2)	C13—C14—H14	119.4
C4—C3—C2	109.2 (3)	C15—C14—H14	119.4
C9—C4—C3	120.2 (3)	C14—C15—C16	120.0 (3)
C9—C4—C5	131.0 (2)	C14—C15—H15	120
C3—C4—C5	108.8 (3)	C16—C15—H15	120
C50—C5—C4	126.7 (2)	C15—C16—C11	120.2 (3)
C50—C5—C1	126.4 (3)	C15—C16—H16	119.9
C4—C5—C1	106.7 (2)	C11—C16—H16	119.9
C7—C6—C3	119.7 (3)	C2—C20—C22	124.4 (3)
C7—C6—H6	120.2	C2—C20—C21	122.7 (3)
C3—C6—H6	120.2	C22—C20—C21	112.9 (2)
C6—C7—C8	120.4 (3)	N21—C21—C20	176.7 (3)
C6—C7—H7	119.8	N22—C22—C20	174.9 (4)
C8—C7—H7	119.8	C5—C50—C52	122.9 (2)
C9—C8—C7	121.4 (3)	C5—C50—C51	123.3 (3)
C9—C8—H8	119.3	C52—C50—C51	113.7 (2)
C7—C8—H8	119.3	N51—C51—C50	177.2 (3)
C8—C9—C4	118.8 (3)	N52—C52—C50	177.4 (3)
C8—C9—H9	120.6	O12—C120—H122	109.5
C4—C9—H9	120.6	O12—C120—H123	109.5
C1—C10—C11	130.8 (3)	H122—C120—H123	109.5
C1—C10—H10	114.6	O12—C120—H121	109.5
C11—C10—H10	114.6	H122—C120—H121	109.5
C12—C11—C16	118.7 (3)	H123—C120—H121	109.5
C12—C11—C10	119.7 (2)
C10—C1—C2—C20	−32.9 (4)	C5—C4—C9—C8	177.0 (3)
C5—C1—C2—C20	161.0 (3)	C2—C1—C10—C11	−7.6 (5)
C10—C1—C2—C3	153.6 (3)	C5—C1—C10—C11	156.4 (3)
C5—C1—C2—C3	−12.5 (3)	C1—C10—C11—C12	151.0 (3)
C20—C2—C3—C6	10.6 (5)	C1—C10—C11—C16	−36.9 (5)
C1—C2—C3—C6	−176.0 (3)	C120—O12—C12—C11	166.0 (2)
C20—C2—C3—C4	−166.9 (3)	C120—O12—C12—C13	−15.8 (4)
C1—C2—C3—C4	6.4 (3)	C16—C11—C12—O12	179.6 (2)
C6—C3—C4—C9	3.2 (4)	C10—C11—C12—O12	−8.1 (4)
C2—C3—C4—C9	−178.9 (3)	C16—C11—C12—C13	1.3 (4)
C6—C3—C4—C5	−175.4 (2)	C10—C11—C12—C13	173.6 (2)
C2—C3—C4—C5	2.4 (3)	O12—C12—C13—C14	−178.3 (3)
C9—C4—C5—C50	−13.1 (5)	C11—C12—C13—C14	−0.1 (4)
C3—C4—C5—C50	165.3 (3)	C12—C13—C14—C15	−1.2 (5)
C9—C4—C5—C1	171.3 (3)	C13—C14—C15—C16	1.2 (5)
C3—C4—C5—C1	−10.3 (3)	C14—C15—C16—C11	0.0 (4)
C10—C1—C5—C50	31.0 (5)	C12—C11—C16—C15	−1.3 (4)
C2—C1—C5—C50	−161.7 (3)	C10—C11—C16—C15	−173.4 (2)
C10—C1—C5—C4	−153.4 (3)	C3—C2—C20—C22	165.7 (3)
C2—C1—C5—C4	13.9 (3)	C1—C2—C20—C22	−6.5 (4)
C4—C3—C6—C7	−2.8 (4)	C3—C2—C20—C21	−12.3 (4)
C2—C3—C6—C7	179.9 (3)	C1—C2—C20—C21	175.4 (2)
C3—C6—C7—C8	0.5 (5)	C4—C5—C50—C52	−167.3 (3)
C6—C7—C8—C9	1.4 (5)	C1—C5—C50—C52	7.4 (5)
C7—C8—C9—C4	−1.0 (5)	C4—C5—C50—C51	10.9 (5)
C3—C4—C9—C8	−1.3 (4)	C1—C5—C50—C51	−174.3 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···N22^iii	0.93	2.73	3.646 (6)	170
C8—H8···N21^iv	0.93	2.64	3.345 (6)	133

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