4,4′-[Propane-1,2-diyl­bis(nitrilo­methyl­idyne)]­dibenzo­nitrile–4,4′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]dibenzonitrile [0.796 (2)/0.204 (2)]

Fun, H.-K.; Kia, R.; Kargar, H.

doi:10.1107/S1600536808031097

4,4′-[Propane-1,2-diylbis(nitrilomethylidyne)]dibenzonitrile–4,4′-[ethane-1,2-diylbis(nitrilomethylidyne)]dibenzonitrile [0.796 (2)/0.204 (2)]

The title cocrystal, 0.796C₁₉H₁₆N₄·0.204C₁₈H₁₄N₄, is a disordered mixture of two potentially bidentate Schiff base ligands. The difference in the two components of the cocrystal is the replacement of the methyl group in the linkage between the imine N atoms in the major component of the Schiff base ligand by an H atom. The imino (C=N) functional groups are coplanar with the benzene rings (only the major component) and extend in opposite directions (both components). Intermolecular π–π interactions with a centroid-to-centroid distance of 3.7371 (8) Å are observed in the crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808031097/ez2140sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808031097/ez2140Isup2.hkl Contains datablock I

CCDC reference: 709362

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R factor = 0.059
wR factor = 0.182
Data-to-parameter ratio = 20.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C8A    --  C19A    ..       9.18 su

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.572
            Test value =      0.525
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.57 e/A   
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     --  C17     ..       5.12 su
PLAT301_ALERT_3_C Main Residue  Disorder .........................      18.00 Perc.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3     -   C17    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C14    -   C18    ...       1.44 Ang.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)         20 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_4_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Labels ..........          7
PLAT779_ALERT_4_C Suspect or Irrelevant (Bond) Angle in CIF ......      24.50 Deg.
              N1B  -C7   -N1A     1.555   1.555   1.555
PLAT779_ALERT_4_C Suspect or Irrelevant (Bond) Angle in CIF ......      23.90 Deg.
              H7A  -C7   -H7B     1.555   1.555   1.555
PLAT779_ALERT_4_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.90 Deg.
              N2A  -C10  -N2B     1.555   1.555   1.555
PLAT779_ALERT_4_C Suspect or Irrelevant (Bond) Angle in CIF ......      32.00 Deg.
              H10A -C10  -H10B    1.555   1.555   1.555

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C18.81 H15.61 N4
            Atom count from _chemical_formula_moiety:C18.8 H15.6 N4
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C18.81 H15.61 N4
            Atom count from the _atom_site data:  C18.796 H15.59200 N4
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies.
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C18.81 H15.61 N4
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         37.62     37.59    0.03
           H         31.22     31.18    0.04
           N          8.00      8.00    0.00
PLAT793_ALERT_4_G Check the Absolute Configuration of C8A    .....          R

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

   9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Schiff bases are among the most prevalent mixed-donor ligands in the field of coordination chemistry. They play an important role in the development of catalysts and enzymatic reactions, magnetic materials and supramolecular architectures. Structures of Schiff bases derived from substituted benzaldehydes and closely related to the title compound have been reported recently (Li et al., 2005; Bomfim et al., 2005; Glidewell et al., 2005, 2006; Sun et al., 2004; Fun, Kargar & Kia, 2008; Fun, Kia & Kargar, 2008).

The title cocrystal consists of two bidentate Schiff base ligands. The bond lengths and angles in the two molecules (I, Fig. 1) are within normal ranges (Allen et al., 1987). In the major component, the imino (C=N) functional groups are coplanar with the benzene rings. The difference in the two components of the co-crystal, which are disordered over two sites, is the replacement of the methyl group in the major component by a hydrogen atom in the linkage between the imino N atoms. The ratio of the refined site occupancy factors of the major and minor components is 0.796 (2)/0.204 (2). The short distance between the centroids of the six-membered rings indicates the existence of π-π interactions (Fig. 2), with a Cg1···Cg1 distance of 3.7371 (8) Å (symmetry code: -x, -y, 2 - z; Cg1 is the centroid of the C11–C16 benzene ring).

Related literature top

For values of bond lengths, see: Allen et al. (1987). For related structures, see, for example: Li et al. (2005); Bomfim et al. (2005); Glidewell et al. (2005, 2006); Sun et al. (2004); Fun, Kia & Kargar (2008); Fun, Kargar & Kia (2008).

Experimental top

The synthetic method has been described previously (Fun, Kargar & Kia, 2008). Single crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol solution at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title cocrystal, with atom labels and 50% probability ellipsoids for non-H atoms. Open bonds indicate the minor component.
	Fig. 2. The crystal packing of the major component of (I), viewed down the b-axis.

4,4'-[propane-1,2-diylbis(nitrilomethylidyne)]dibenzonitrile– 4,4'-[ethane-1,2-diylbis(nitrilomethylidyne)]dibenzonitrile [0.796 (2)/0.204 (2)] top

Crystal data top

0.796C₁₉H₁₆N₄·0.204C₁₈H₁₄N₄	Z = 2
M_r = 297.68	F(000) = 313
Triclinic, P1	D_x = 1.251 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2370 (2) Å	Cell parameters from 6569 reflections
b = 9.7769 (2) Å	θ = 3.2–30.8°
c = 9.8169 (2) Å	µ = 0.08 mm⁻¹
α = 81.846 (1)°	T = 100 K
β = 75.098 (1)°	Block, colourless
γ = 67.421 (1)°	0.39 × 0.38 × 0.27 mm
V = 790.15 (3) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4628 independent reflections
Radiation source: fine-focus sealed tube	3746 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
T_min = 0.890, T_max = 0.979	k = −13→13
17295 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0996P)² + 0.2311P] where P = (F_o² + 2F_c²)/3
4628 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

0.796C₁₉H₁₆N₄·0.204C₁₈H₁₄N₄	γ = 67.421 (1)°
M_r = 297.68	V = 790.15 (3) Å³
Triclinic, P1	Z = 2
a = 9.2370 (2) Å	Mo Kα radiation
b = 9.7769 (2) Å	µ = 0.08 mm⁻¹
c = 9.8169 (2) Å	T = 100 K
α = 81.846 (1)°	0.39 × 0.38 × 0.27 mm
β = 75.098 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4628 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3746 reflections with I > 2σ(I)
T_min = 0.890, T_max = 0.979	R_int = 0.020
17295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.182	H-atom parameters constrained
S = 1.05	Δρ_max = 0.57 e Å⁻³
4628 reflections	Δρ_min = −0.48 e Å⁻³
230 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	Occ. (<1)
N1A	0.44472 (19)	0.58449 (16)	0.76563 (18)	0.0277 (3)	0.796 (2)
N2A	0.31537 (17)	0.28586 (16)	0.96983 (15)	0.0294 (3)	0.796 (2)
C8A	0.41965 (19)	0.44248 (17)	0.78683 (17)	0.0276 (3)	0.796 (2)
H8AA	0.5235	0.3602	0.7675	0.033*	0.796 (2)
C9A	0.3328 (2)	0.42957 (19)	0.93985 (17)	0.0311 (4)	0.796 (2)
H9AA	0.3933	0.4409	1.0021	0.037*	0.796 (2)
H9AB	0.2275	0.5079	0.9569	0.037*	0.796 (2)
C19A	0.3162 (2)	0.44326 (18)	0.68371 (15)	0.0302 (4)	0.796 (2)
H19A	0.3770	0.4426	0.5883	0.045*	0.796 (2)
H19B	0.2204	0.5308	0.6954	0.045*	0.796 (2)
H19C	0.2873	0.3569	0.7039	0.045*	0.796 (2)
N1B	0.4751 (7)	0.5817 (7)	0.8069 (6)	0.0236 (13)*	0.204 (2)
N2B	0.2894 (7)	0.2948 (6)	0.8959 (6)	0.0294 (3)	0.204 (2)
C8B	0.4619 (7)	0.4375 (6)	0.8536 (6)	0.0225 (11)*	0.204 (2)
H8BA	0.4726	0.4144	0.9508	0.027*	0.204 (2)
H8BB	0.5478	0.3612	0.7959	0.027*	0.204 (2)
C9B	0.2974 (6)	0.4397 (6)	0.8414 (6)	0.0203 (10)	0.204 (2)
H9BA	0.2106	0.5179	0.8962	0.024*	0.204 (2)
H9BB	0.2881	0.4571	0.7437	0.024*	0.204 (2)
N3	0.77232 (14)	1.20704 (14)	0.53274 (13)	0.0356 (3)
N4	0.04293 (17)	−0.36229 (15)	1.22228 (16)	0.0481 (4)
C1	0.77783 (15)	0.70764 (15)	0.59144 (14)	0.0310 (3)
H1A	0.8552	0.6156	0.5652	0.037*
C2	0.81727 (15)	0.83368 (15)	0.55783 (13)	0.0301 (3)
H2A	0.9207	0.8263	0.5101	0.036*
C3	0.70001 (14)	0.97147 (14)	0.59648 (12)	0.0250 (2)
C4	0.54475 (14)	0.98285 (14)	0.66949 (13)	0.0281 (3)
H4A	0.4671	1.0749	0.6957	0.034*
C5	0.50763 (14)	0.85626 (14)	0.70243 (13)	0.0274 (3)
H5A	0.4043	0.8635	0.7507	0.033*
C6	0.62345 (14)	0.71778 (14)	0.66410 (12)	0.0248 (2)
C7	0.58542 (16)	0.58172 (14)	0.69901 (14)	0.0302 (3)
H7A	0.6682	0.4882	0.6713	0.036*	0.796 (2)
H7B	0.6427	0.4971	0.6419	0.036*	0.204 (2)
C10	0.18277 (17)	0.28390 (16)	1.04041 (17)	0.0379 (3)
H10A	0.0979	0.3754	1.0711	0.045*	0.796 (2)
H10B	0.1389	0.3631	1.1042	0.045*	0.204 (2)
C11	0.15451 (14)	0.14439 (14)	1.07915 (13)	0.0269 (3)
C12	0.00891 (15)	0.14545 (14)	1.16669 (14)	0.0309 (3)
H12A	−0.0691	0.2345	1.2005	0.037*
C13	−0.02034 (15)	0.01501 (14)	1.20368 (13)	0.0285 (3)
H13A	−0.1174	0.0161	1.2625	0.034*
C14	0.09638 (15)	−0.11766 (14)	1.15229 (13)	0.0269 (3)
C15	0.24291 (15)	−0.12015 (15)	1.06462 (14)	0.0316 (3)
H15A	0.3205	−0.2092	1.0303	0.038*
C16	0.27163 (14)	0.01010 (14)	1.02930 (13)	0.0283 (3)
H16A	0.3695	0.0086	0.9720	0.034*
C17	0.73983 (15)	1.10277 (15)	0.56153 (13)	0.0281 (3)
C18	0.06622 (17)	−0.25355 (16)	1.19090 (15)	0.0348 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0290 (7)	0.0270 (7)	0.0282 (7)	−0.0139 (5)	−0.0013 (6)	−0.0031 (5)
N2A	0.0304 (6)	0.0287 (6)	0.0298 (7)	−0.0149 (5)	−0.0010 (5)	−0.0024 (5)
C8A	0.0276 (7)	0.0234 (7)	0.0311 (8)	−0.0119 (6)	−0.0002 (6)	−0.0034 (6)
C9A	0.0340 (8)	0.0303 (8)	0.0313 (8)	−0.0176 (6)	0.0008 (6)	−0.0062 (6)
C19A	0.0537 (10)	0.0276 (7)	0.0222 (7)	−0.0273 (7)	−0.0126 (6)	0.0023 (5)
N2B	0.0304 (6)	0.0287 (6)	0.0298 (7)	−0.0149 (5)	−0.0010 (5)	−0.0024 (5)
C9B	0.024 (2)	0.016 (2)	0.021 (2)	−0.0076 (19)	−0.0053 (18)	0.0005 (18)
N3	0.0337 (6)	0.0363 (6)	0.0387 (6)	−0.0187 (5)	0.0002 (5)	−0.0055 (5)
N4	0.0457 (7)	0.0340 (7)	0.0585 (8)	−0.0165 (6)	0.0000 (6)	0.0008 (6)
C1	0.0258 (6)	0.0283 (6)	0.0341 (6)	−0.0090 (5)	0.0027 (5)	−0.0060 (5)
C2	0.0239 (5)	0.0335 (7)	0.0312 (6)	−0.0127 (5)	0.0020 (4)	−0.0046 (5)
C3	0.0253 (5)	0.0294 (6)	0.0229 (5)	−0.0134 (5)	−0.0033 (4)	−0.0031 (4)
C4	0.0235 (5)	0.0265 (6)	0.0325 (6)	−0.0096 (4)	−0.0006 (4)	−0.0051 (5)
C5	0.0225 (5)	0.0294 (6)	0.0298 (6)	−0.0116 (5)	−0.0006 (4)	−0.0036 (5)
C6	0.0252 (5)	0.0268 (6)	0.0219 (5)	−0.0112 (4)	−0.0011 (4)	−0.0029 (4)
C7	0.0304 (6)	0.0258 (6)	0.0308 (6)	−0.0108 (5)	0.0010 (5)	−0.0025 (5)
C10	0.0293 (6)	0.0273 (6)	0.0558 (9)	−0.0129 (5)	0.0018 (6)	−0.0112 (6)
C11	0.0248 (5)	0.0261 (6)	0.0312 (6)	−0.0105 (4)	−0.0043 (4)	−0.0055 (4)
C12	0.0260 (6)	0.0257 (6)	0.0360 (6)	−0.0066 (5)	0.0000 (5)	−0.0066 (5)
C13	0.0236 (5)	0.0305 (6)	0.0283 (6)	−0.0094 (5)	−0.0015 (4)	−0.0008 (5)
C14	0.0269 (6)	0.0263 (6)	0.0263 (5)	−0.0094 (5)	−0.0046 (4)	−0.0005 (4)
C15	0.0271 (6)	0.0265 (6)	0.0358 (6)	−0.0072 (5)	0.0004 (5)	−0.0057 (5)
C16	0.0232 (5)	0.0299 (6)	0.0303 (6)	−0.0100 (5)	−0.0006 (4)	−0.0054 (5)
C17	0.0256 (5)	0.0330 (6)	0.0269 (6)	−0.0134 (5)	−0.0013 (4)	−0.0054 (5)
C18	0.0326 (6)	0.0304 (7)	0.0372 (7)	−0.0113 (5)	−0.0012 (5)	−0.0005 (5)

Geometric parameters (Å, º) top

N1A—C7	1.2878 (18)	C2—C3	1.3947 (18)
N1A—C8A	1.4714 (19)	C2—H2A	0.9300
N2A—C10	1.2484 (18)	C3—C4	1.3979 (16)
N2A—C9A	1.455 (2)	C3—C17	1.4400 (16)
C8A—C9A	1.523 (2)	C4—C5	1.3818 (16)
C8A—C19A	1.558 (2)	C4—H4A	0.9300
C8A—H8AA	0.9800	C5—C6	1.3944 (17)
C9A—H9AA	0.9700	C5—H5A	0.9300
C9A—H9AB	0.9700	C6—C7	1.4758 (16)
C19A—H19A	0.9600	C7—H7A	0.9600
C19A—H19B	0.9600	C7—H7B	0.9600
C19A—H19C	0.9600	C10—C11	1.4658 (17)
N1B—C7	1.267 (6)	C10—H10A	0.9600
N1B—C8B	1.460 (8)	C10—H10B	0.9600
N2B—C9B	1.464 (7)	C11—C12	1.3945 (17)
N2B—C10	1.521 (6)	C11—C16	1.3975 (17)
C8B—C9B	1.546 (8)	C12—C13	1.3834 (17)
C8B—H8BA	0.9700	C12—H12A	0.9300
C8B—H8BB	0.9700	C13—C14	1.3897 (17)
C9B—H9BA	0.9700	C13—H13A	0.9300
C9B—H9BB	0.9700	C14—C15	1.3982 (17)
N3—C17	1.1484 (17)	C14—C18	1.4400 (18)
N4—C18	1.1489 (19)	C15—C16	1.3781 (17)
C1—C2	1.3883 (17)	C15—H15A	0.9300
C1—C6	1.3930 (16)	C16—H16A	0.9300
C1—H1A	0.9300

C7—N1A—C8A	116.77 (13)	C1—C6—C5	119.43 (11)
C10—N2A—C9A	117.17 (13)	C1—C6—C7	119.38 (11)
N1A—C8A—C9A	107.68 (13)	C5—C6—C7	121.19 (10)
N1A—C8A—C19A	108.24 (13)	N1B—C7—N1A	24.5 (2)
C9A—C8A—C19A	111.02 (13)	N1B—C7—C6	117.3 (3)
N1A—C8A—H8AA	110.0	N1A—C7—C6	122.07 (12)
C9A—C8A—H8AA	110.0	N1B—C7—H7A	117.8
C19A—C8A—H8AA	110.0	N1A—C7—H7A	119.0
N2A—C9A—C8A	110.09 (13)	C6—C7—H7A	119.0
N2A—C9A—H9AA	109.6	N1B—C7—H7B	121.9
C8A—C9A—H9AA	109.6	N1A—C7—H7B	111.9
N2A—C9A—H9AB	109.6	C6—C7—H7B	120.8
C8A—C9A—H9AB	109.6	H7A—C7—H7B	23.9
H9AA—C9A—H9AB	108.2	N2A—C10—C11	121.33 (13)
C7—N1B—C8B	115.5 (5)	N2A—C10—N2B	31.9 (2)
C9B—N2B—C10	118.6 (4)	C11—C10—N2B	116.6 (2)
N1B—C8B—C9B	110.0 (5)	N2A—C10—H10A	119.5
N1B—C8B—H8BA	109.7	C11—C10—H10A	119.2
C9B—C8B—H8BA	109.7	N2B—C10—H10A	114.8
N1B—C8B—H8BB	109.7	N2A—C10—H10B	107.4
C9B—C8B—H8BB	109.7	C11—C10—H10B	121.7
H8BA—C8B—H8BB	108.2	N2B—C10—H10B	121.8
N2B—C9B—C8B	107.0 (4)	H10A—C10—H10B	32.0
N2B—C9B—H9BA	110.3	C12—C11—C16	119.49 (11)
C8B—C9B—H9BA	110.3	C12—C11—C10	119.68 (11)
N2B—C9B—H9BB	110.3	C16—C11—C10	120.83 (11)
C8B—C9B—H9BB	110.3	C13—C12—C11	120.51 (11)
H9BA—C9B—H9BB	108.6	C13—C12—H12A	119.7
C2—C1—C6	120.64 (11)	C11—C12—H12A	119.7
C2—C1—H1A	119.7	C12—C13—C14	119.49 (11)
C6—C1—H1A	119.7	C12—C13—H13A	120.3
C1—C2—C3	119.28 (11)	C14—C13—H13A	120.3
C1—C2—H2A	120.4	C13—C14—C15	120.52 (12)
C3—C2—H2A	120.4	C13—C14—C18	119.56 (11)
C2—C3—C4	120.53 (11)	C15—C14—C18	119.92 (11)
C2—C3—C17	119.61 (10)	C16—C15—C14	119.61 (11)
C4—C3—C17	119.86 (11)	C16—C15—H15A	120.2
C5—C4—C3	119.44 (11)	C14—C15—H15A	120.2
C5—C4—H4A	120.3	C15—C16—C11	120.37 (11)
C3—C4—H4A	120.3	C15—C16—H16A	119.8
C4—C5—C6	120.68 (11)	C11—C16—H16A	119.8
C4—C5—H5A	119.7	N3—C17—C3	179.50 (14)
C6—C5—H5A	119.7	N4—C18—C14	179.53 (16)

C7—N1A—C8A—C9A	134.28 (16)	C1—C6—C7—N1B	152.5 (3)
C7—N1A—C8A—C19A	−105.62 (18)	C5—C6—C7—N1B	−27.5 (4)
C10—N2A—C9A—C8A	−136.91 (16)	C1—C6—C7—N1A	−179.80 (14)
N1A—C8A—C9A—N2A	−175.76 (13)	C5—C6—C7—N1A	0.2 (2)
C19A—C8A—C9A—N2A	65.92 (17)	C9A—N2A—C10—C11	−178.46 (13)
C7—N1B—C8B—C9B	−116.7 (5)	C9A—N2A—C10—N2B	90.8 (4)
C10—N2B—C9B—C8B	105.6 (5)	C9B—N2B—C10—N2A	−83.9 (6)
N1B—C8B—C9B—N2B	−177.4 (5)	C9B—N2B—C10—C11	168.8 (4)
C6—C1—C2—C3	−0.6 (2)	N2A—C10—C11—C12	175.33 (15)
C1—C2—C3—C4	0.61 (19)	N2B—C10—C11—C12	−148.5 (3)
C1—C2—C3—C17	−179.77 (11)	N2A—C10—C11—C16	−4.8 (2)
C2—C3—C4—C5	−0.45 (19)	N2B—C10—C11—C16	31.4 (3)
C17—C3—C4—C5	179.94 (11)	C16—C11—C12—C13	−0.31 (19)
C3—C4—C5—C6	0.25 (19)	C10—C11—C12—C13	179.60 (12)
C2—C1—C6—C5	0.38 (19)	C11—C12—C13—C14	−0.35 (19)
C2—C1—C6—C7	−179.66 (11)	C12—C13—C14—C15	0.44 (19)
C4—C5—C6—C1	−0.22 (19)	C12—C13—C14—C18	179.89 (12)
C4—C5—C6—C7	179.83 (11)	C13—C14—C15—C16	0.1 (2)
C8B—N1B—C7—N1A	83.2 (8)	C18—C14—C15—C16	−179.31 (12)
C8B—N1B—C7—C6	−168.7 (4)	C14—C15—C16—C11	−0.8 (2)
C8A—N1A—C7—N1B	−97.6 (8)	C12—C11—C16—C15	0.90 (19)
C8A—N1A—C7—C6	176.59 (13)	C10—C11—C16—C15	−179.01 (12)

Experimental details

Crystal data
Chemical formula	0.796C₁₉H₁₆N₄·0.204C₁₈H₁₄N₄
M_r	297.68
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.2370 (2), 9.7769 (2), 9.8169 (2)
α, β, γ (°)	81.846 (1), 75.098 (1), 67.421 (1)
V (Å³)	790.15 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.39 × 0.38 × 0.27

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.890, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	17295, 4628, 3746
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.182, 1.05
No. of reflections	4628
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.48

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

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4,4′-[Propane-1,2-diyl­bis(nitrilo­methyl­idyne)]­dibenzo­nitrile–4,4′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]dibenzonitrile [0.796 (2)/0.204 (2)]

Supporting information

Key indicators

checkCIF/PLATON results

4,4′-[Propane-1,2-diylbis(nitrilomethylidyne)]dibenzonitrile–4,4′-[ethane-1,2-diylbis(nitrilomethylidyne)]dibenzonitrile [0.796 (2)/0.204 (2)]