In the title compound, C
12H
10N
4O, the structure is stabilized by an extensive network of N—H
N and N—H
O hydrogen bonds, forming columnar stacks down the
c axis. As a powder, the compound exhibits second-harmonic generation efficiency.
Supporting information
CCDC reference: 610905
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.048
- wR factor = 0.127
- Data-to-parameter ratio = 9.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C9 - C10 ... 1.44 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C11 - C12 ... 1.45 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 22
N4 -C11 -C12 -N3 17.00 0.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 23
C10 -C11 -C12 -N3 1.00 0.00 1.555 1.555 1.555 1.555
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 26.99
From the CIF: _reflns_number_total 1403
Count of symmetry unique reflns 1417
Completeness (_total/calc) 99.01%
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
5 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
2-Amino-3-(4-methoxybenzylideneamino)butenedinitrile
top
Crystal data top
C12H10N4O | F(000) = 472 |
Mr = 226.24 | Dx = 1.321 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 3181 reflections |
a = 11.108 (2) Å | θ = 2.4–27.6° |
b = 25.481 (5) Å | µ = 0.09 mm−1 |
c = 4.0203 (8) Å | T = 298 K |
V = 1137.9 (4) Å3 | Prism, yellow |
Z = 4 | 0.35 × 0.21 × 0.12 mm |
Data collection top
Bruker SMART APEX CCD diffractometer | 1403 independent reflections |
Radiation source: fine-focus sealed tube | 1361 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 27.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→14 |
Tmin = 0.969, Tmax = 0.989 | k = −26→32 |
6445 measured reflections | l = −5→5 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0549P)2 + 0.195P] where P = (Fo2 + 2Fc2)/3 |
S = 1.31 | (Δ/σ)max = 0.011 |
1403 reflections | Δρmax = 0.19 e Å−3 |
156 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.033 (6) |
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. |
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 (Å2) top | x | y | z | Uiso*/Ueq | |
C8 | 0.1575 (2) | 0.63116 (10) | 0.3670 (8) | 0.0397 (6) | |
H10 | 0.2056 | 0.6568 | 0.4643 | 0.048* | |
O1 | 0.28885 (19) | 0.42004 (7) | 0.4809 (8) | 0.0602 (7) | |
C2 | 0.2643 (2) | 0.47242 (9) | 0.4599 (8) | 0.0412 (6) | |
C10 | 0.0359 (2) | 0.69844 (9) | 0.1752 (8) | 0.0387 (6) | |
N1 | 0.06251 (19) | 0.64529 (8) | 0.2098 (6) | 0.0397 (6) | |
C6 | 0.1923 (2) | 0.57631 (9) | 0.3982 (7) | 0.0354 (6) | |
N4 | −0.1410 (2) | 0.67782 (9) | −0.1351 (8) | 0.0523 (8) | |
H6A | −0.1287 | 0.6447 | −0.1138 | 0.063* | |
H5B | −0.2027 | 0.6889 | −0.2432 | 0.063* | |
C11 | −0.0641 (2) | 0.71212 (9) | 0.0000 (8) | 0.0396 (7) | |
C5 | 0.1226 (2) | 0.53581 (10) | 0.2649 (8) | 0.0414 (7) | |
H4 | 0.0512 | 0.5438 | 0.1550 | 0.050* | |
C9 | 0.1095 (2) | 0.73852 (10) | 0.3225 (9) | 0.0421 (7) | |
C7 | 0.2986 (2) | 0.56343 (10) | 0.5594 (8) | 0.0410 (7) | |
H1 | 0.3462 | 0.5900 | 0.6473 | 0.049* | |
N3 | −0.1118 (2) | 0.81051 (10) | −0.0854 (11) | 0.0691 (10) | |
C1 | 0.3353 (2) | 0.51173 (10) | 0.5921 (9) | 0.0439 (7) | |
H2 | 0.4066 | 0.5036 | 0.7015 | 0.053* | |
C4 | 0.1580 (2) | 0.48473 (10) | 0.2941 (9) | 0.0441 (7) | |
H3 | 0.1110 | 0.4581 | 0.2032 | 0.053* | |
N2 | 0.1705 (2) | 0.76848 (9) | 0.4476 (10) | 0.0594 (8) | |
C12 | −0.0912 (2) | 0.76733 (11) | −0.0485 (10) | 0.0465 (7) | |
C3 | 0.3947 (3) | 0.40410 (12) | 0.6547 (13) | 0.0675 (11) | |
H7A | 0.4641 | 0.4192 | 0.5500 | 0.101* | |
H9B | 0.4009 | 0.3665 | 0.6497 | 0.101* | |
H8C | 0.3901 | 0.4158 | 0.8813 | 0.101* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C8 | 0.0414 (12) | 0.0325 (12) | 0.0451 (17) | −0.0009 (9) | −0.0034 (13) | 0.0010 (12) |
O1 | 0.0644 (12) | 0.0296 (9) | 0.0866 (18) | 0.0041 (8) | −0.0037 (14) | 0.0029 (12) |
C2 | 0.0443 (13) | 0.0312 (12) | 0.0480 (16) | −0.0001 (10) | 0.0087 (13) | 0.0047 (12) |
C10 | 0.0374 (12) | 0.0322 (12) | 0.0466 (16) | −0.0030 (9) | −0.0020 (12) | 0.0031 (12) |
N1 | 0.0388 (11) | 0.0336 (11) | 0.0469 (15) | 0.0024 (8) | −0.0026 (11) | 0.0034 (11) |
C6 | 0.0349 (11) | 0.0332 (12) | 0.0381 (15) | −0.0007 (9) | 0.0023 (11) | 0.0035 (11) |
N4 | 0.0474 (12) | 0.0380 (12) | 0.071 (2) | 0.0012 (9) | −0.0174 (14) | 0.0040 (13) |
C11 | 0.0368 (12) | 0.0333 (12) | 0.0487 (18) | 0.0008 (9) | 0.0013 (13) | 0.0047 (12) |
C5 | 0.0343 (12) | 0.0408 (14) | 0.0491 (18) | −0.0007 (10) | −0.0049 (12) | 0.0051 (13) |
C9 | 0.0406 (13) | 0.0331 (13) | 0.0526 (18) | 0.0032 (10) | −0.0040 (13) | 0.0065 (13) |
C7 | 0.0404 (13) | 0.0332 (12) | 0.0494 (17) | −0.0035 (9) | −0.0072 (13) | −0.0004 (12) |
N3 | 0.0662 (16) | 0.0383 (13) | 0.103 (3) | 0.0041 (11) | −0.0190 (19) | 0.0122 (18) |
C1 | 0.0399 (13) | 0.0399 (14) | 0.0519 (19) | 0.0035 (10) | −0.0063 (13) | 0.0030 (14) |
C4 | 0.0436 (13) | 0.0346 (13) | 0.0540 (19) | −0.0088 (11) | −0.0004 (14) | −0.0029 (14) |
N2 | 0.0572 (14) | 0.0417 (12) | 0.079 (2) | −0.0075 (11) | −0.0199 (16) | 0.0002 (15) |
C12 | 0.0408 (13) | 0.0385 (14) | 0.060 (2) | −0.0008 (10) | −0.0091 (15) | 0.0057 (14) |
C3 | 0.075 (2) | 0.0426 (16) | 0.085 (3) | 0.0181 (15) | 0.001 (2) | 0.011 (2) |
Geometric parameters (Å, º) top
C8—N1 | 1.281 (3) | N4—H5B | 0.8600 |
C8—C6 | 1.456 (3) | C11—C12 | 1.452 (4) |
C8—H10 | 0.9300 | C5—C4 | 1.365 (4) |
O1—C2 | 1.365 (3) | C5—H4 | 0.9300 |
O1—C3 | 1.426 (4) | C9—N2 | 1.139 (4) |
C2—C1 | 1.381 (4) | C7—C1 | 1.385 (3) |
C2—C4 | 1.392 (4) | C7—H1 | 0.9300 |
C10—C11 | 1.361 (4) | N3—C12 | 1.134 (3) |
C10—N1 | 1.393 (3) | C1—H2 | 0.9300 |
C10—C9 | 1.436 (4) | C4—H3 | 0.9300 |
C6—C7 | 1.386 (4) | C3—H7A | 0.9600 |
C6—C5 | 1.397 (4) | C3—H9B | 0.9600 |
N4—C11 | 1.337 (4) | C3—H8C | 0.9600 |
N4—H6A | 0.8600 | | |
| | | |
N1—C8—C6 | 122.1 (2) | C4—C5—C6 | 120.8 (2) |
N1—C8—H10 | 119.0 | C4—C5—H4 | 119.6 |
C6—C8—H10 | 119.0 | C6—C5—H4 | 119.6 |
C2—O1—C3 | 118.2 (2) | N2—C9—C10 | 176.7 (3) |
O1—C2—C1 | 124.9 (3) | C1—C7—C6 | 121.3 (2) |
O1—C2—C4 | 114.8 (2) | C1—C7—H1 | 119.3 |
C1—C2—C4 | 120.3 (2) | C6—C7—H1 | 119.3 |
C11—C10—N1 | 118.3 (2) | C2—C1—C7 | 119.0 (2) |
C11—C10—C9 | 119.7 (2) | C2—C1—H2 | 120.5 |
N1—C10—C9 | 122.0 (2) | C7—C1—H2 | 120.5 |
C8—N1—C10 | 119.8 (2) | C5—C4—C2 | 120.0 (2) |
C7—C6—C5 | 118.5 (2) | C5—C4—H3 | 120.0 |
C7—C6—C8 | 119.6 (2) | C2—C4—H3 | 120.0 |
C5—C6—C8 | 121.9 (2) | N3—C12—C11 | 179.7 (4) |
C11—N4—H6A | 120.0 | O1—C3—H7A | 109.5 |
C11—N4—H5B | 120.0 | O1—C3—H9B | 109.5 |
H6A—N4—H5B | 120.0 | H7A—C3—H9B | 109.5 |
N4—C11—C10 | 124.3 (2) | O1—C3—H8C | 109.5 |
N4—C11—C12 | 116.5 (2) | H7A—C3—H8C | 109.5 |
C10—C11—C12 | 119.1 (2) | H9B—C3—H8C | 109.5 |
| | | |
C3—O1—C2—C1 | 0.7 (5) | C8—C6—C5—C4 | 179.2 (3) |
C3—O1—C2—C4 | −178.4 (3) | C5—C6—C7—C1 | −0.6 (4) |
C6—C8—N1—C10 | −177.3 (3) | C8—C6—C7—C1 | −179.5 (3) |
C11—C10—N1—C8 | 178.5 (3) | O1—C2—C1—C7 | −178.6 (3) |
C9—C10—N1—C8 | −2.5 (4) | C4—C2—C1—C7 | 0.5 (5) |
N1—C8—C6—C7 | 177.4 (3) | C6—C7—C1—C2 | 0.2 (5) |
N1—C8—C6—C5 | −1.5 (4) | C6—C5—C4—C2 | 0.4 (5) |
N1—C10—C11—N4 | 1.8 (5) | O1—C2—C4—C5 | 178.4 (3) |
C9—C10—C11—N4 | −177.2 (3) | C1—C2—C4—C5 | −0.8 (5) |
N1—C10—C11—C12 | −177.9 (3) | N4—C11—C12—N3 | 174 (100) |
C9—C10—C11—C12 | 3.0 (5) | C10—C11—C12—N3 | −6 (90) |
C7—C6—C5—C4 | 0.3 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H5B···N2i | 0.86 | 2.17 | 3.012 (4) | 166 |
N4—H6A···O1ii | 0.86 | 2.46 | 3.022 (3) | 124 |
Symmetry codes: (i) x−1/2, −y+3/2, z−1; (ii) −x, −y+1, z−1/2. |