2-Amino-3-(4-methoxy­benzyl­ideneamino)butenedinitrile

Wu, C.-J.; Zhang, X.; Zhang, G.-Q.; Liu, L.-D.; Shi, J.-M.

doi:10.1107/S160053680601960X

2-Amino-3-(4-methoxybenzylideneamino)butenedinitrile

C.-J. Wu, X. Zhang, G.-Q. Zhang, L.-D. Liu and J.-M. Shi

In the title compound, C₁₂H₁₀N₄O, 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601960X/sj2073sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680601960X/sj2073Isup2.hkl Contains datablock I

CCDC reference: 610905

checkCIF report

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

Computing details top

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
M_r = 226.24	D_x = 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	R_int = 0.047
φ and ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→14
T_min = 0.969, T_max = 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(F_o²) + (0.0549P)² + 0.195P] where P = (F_o² + 2F_c²)/3
S = 1.31	(Δ/σ)_max = 0.011
1403 reflections	Δρ_max = 0.19 e Å⁻³
156 parameters	Δρ_min = −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	U_iso*/U_eq
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.

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2-Amino-3-(4-methoxy­benzyl­ideneamino)butenedinitrile

Supporting information

Key indicators

checkCIF/PLATON results

2-Amino-3-(4-methoxybenzylideneamino)butenedinitrile