The title compound, C
23H
12N
4O, 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.
Supporting information
CCDC reference: 613779
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | Needle, orange |
Z = 4 | 0.5 × 0.1 × 0.1 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.031 |
[exp{5(sinθ/λ)2}]/[σ2(Fo2) + (0.01P)2]
where P = 0.33333Fo2 + 0.66667Fc2 |
wR(F2) = 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 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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···C52i | 3.064 (7) | N52···C51ii | 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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···N22iii | 0.93 | 2.73 | 3.646 (6) | 170 |
C8—H8···N21iv | 0.93 | 2.64 | 3.345 (6) | 133 |
Symmetry codes: (iii) x, y, z−1; (iv) x−1/2, −y+1/2, −z+1. |