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The achiral title compound, C12H6N2, crystallizes in the non-centrosymmetric space group P212121. Its structure is compared with that of the triclinic polymorph, which crystallizes with two independent molecules in space group P1. In the crystal structure, the molecules stack along the a direction, and zigzag chains, extending in the b direction, are formed owing to the presence of C—H...N intermolecular contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031757/sj6037sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031757/sj6037Isup2.hkl
Contains datablock I

CCDC reference: 262437

Key indicators

  • Single-crystal X-ray study
  • T = 153 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.105
  • Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found



Alert level A DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards.
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.98 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C12 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C3 - C11 ... 1.44 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 26.07 From the CIF: _reflns_number_total 1054 Count of symmetry unique reflns 1062 Completeness (_total/calc) 99.25% 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
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2004); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

naphthalene-2,3-dicarbonitrile top
Crystal data top
C12H6N2F(000) = 368
Mr = 178.19Dx = 1.355 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6447 reflections
a = 3.8144 (5) Åθ = 1.7–26.1°
b = 12.175 (2) ŵ = 0.08 mm1
c = 18.806 (3) ÅT = 153 K
V = 873.4 (2) Å3Block, colourless
Z = 40.45 × 0.25 × 0.15 mm
Data collection top
Stoe IPDS-II
diffractometer
915 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.066
Graphite monochromatorθmax = 26.1°, θmin = 2.0°
Detector resolution: 0.81Å pixels mm-1h = 44
φ or ω scans?k = 1515
6296 measured reflectionsl = 2321
1054 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: difference Fourier map
wR(F2) = 0.105All H-atom parameters refined
S = 0.87 w1/[σ2(Fo2) + (0.0678P)2]
where P(Fo2 + 2Fc2)/3
1054 reflections(Δ/σ)max < 0.001
151 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.14 e Å3
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
xyzUiso*/Ueq
N10.5375 (5)0.36284 (13)0.31544 (8)0.0492 (5)
N20.2937 (5)0.67649 (13)0.33499 (9)0.0492 (4)
C10.0198 (5)0.62915 (14)0.16283 (9)0.0376 (4)
H10.093 (6)0.7065 (18)0.1693 (9)0.036 (5)*
C20.1440 (5)0.57532 (14)0.21771 (9)0.0363 (4)
C30.2388 (5)0.46213 (14)0.20996 (9)0.0367 (4)
C40.1722 (5)0.40828 (15)0.14776 (10)0.0387 (4)
H40.243 (6)0.3321 (17)0.1415 (10)0.039 (5)*
C50.0706 (6)0.40796 (17)0.02555 (10)0.0447 (5)
H50.016 (7)0.3286 (19)0.0198 (11)0.055 (6)*
C60.2324 (6)0.46300 (18)0.02889 (11)0.0502 (5)
H60.282 (8)0.427 (2)0.0739 (13)0.060 (7)*
C70.3309 (6)0.57365 (19)0.02107 (11)0.0485 (5)
H70.435 (7)0.610 (2)0.0627 (13)0.068 (7)*
C80.2647 (6)0.62829 (16)0.04127 (10)0.0427 (5)
H80.341 (6)0.7043 (19)0.0479 (10)0.044 (5)*
C90.0951 (5)0.57420 (14)0.09836 (9)0.0380 (4)
C100.0024 (5)0.46204 (15)0.09042 (9)0.0388 (4)
C110.4059 (5)0.40701 (14)0.26844 (10)0.0390 (4)
C120.2243 (6)0.63200 (14)0.28299 (9)0.0401 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0576 (11)0.0388 (8)0.0512 (9)0.0007 (8)0.0056 (9)0.0027 (7)
N20.0583 (11)0.0386 (8)0.0509 (9)0.0008 (8)0.0035 (9)0.0034 (7)
C10.0365 (9)0.0295 (7)0.0469 (9)0.0003 (8)0.0038 (9)0.0020 (6)
C20.0354 (9)0.0325 (8)0.0410 (9)0.0035 (7)0.0043 (7)0.0004 (7)
C30.0355 (9)0.0320 (8)0.0427 (9)0.0008 (8)0.0017 (8)0.0034 (6)
C40.0390 (10)0.0298 (8)0.0473 (10)0.0018 (8)0.0038 (8)0.0005 (7)
C50.0439 (10)0.0427 (9)0.0476 (10)0.0005 (9)0.0018 (9)0.0057 (8)
C60.0446 (11)0.0631 (13)0.0428 (10)0.0019 (11)0.0001 (9)0.0046 (8)
C70.0427 (11)0.0590 (12)0.0438 (10)0.0005 (10)0.0028 (9)0.0064 (9)
C80.0394 (11)0.0430 (10)0.0458 (10)0.0012 (9)0.0022 (9)0.0074 (8)
C90.0357 (9)0.0355 (9)0.0429 (9)0.0010 (8)0.0047 (8)0.0031 (7)
C100.0365 (10)0.0368 (9)0.0431 (9)0.0023 (9)0.0040 (8)0.0002 (7)
C110.0401 (10)0.0307 (7)0.0463 (9)0.0026 (8)0.0003 (9)0.0011 (7)
C120.0422 (11)0.0320 (8)0.0460 (10)0.0004 (8)0.0011 (9)0.0006 (7)
Geometric parameters (Å, º) top
N1—C111.150 (2)C5—C61.371 (3)
N2—C121.149 (2)C5—C101.414 (3)
C1—C21.373 (3)C5—H51.00 (2)
C1—C91.414 (2)C6—C71.406 (3)
C1—H10.99 (2)C6—H60.97 (2)
C2—C31.432 (2)C7—C81.371 (3)
C2—C121.441 (2)C7—H70.98 (3)
C3—C41.365 (3)C8—C91.416 (3)
C3—C111.437 (3)C8—H80.98 (2)
C4—C101.418 (3)C9—C101.423 (2)
C4—H40.97 (2)
C2—C1—C9120.74 (15)C5—C6—H6121.1 (15)
C2—C1—H1119.4 (11)C7—C6—H6118.2 (15)
C9—C1—H1119.9 (11)C8—C7—C6120.3 (2)
C1—C2—C3119.85 (16)C8—C7—H7122.6 (15)
C1—C2—C12120.56 (15)C6—C7—H7117.0 (15)
C3—C2—C12119.58 (17)C7—C8—C9120.45 (18)
C4—C3—C2120.16 (16)C7—C8—H8120.9 (12)
C4—C3—C11120.93 (15)C9—C8—H8118.6 (12)
C2—C3—C11118.91 (16)C8—C9—C1121.52 (16)
C3—C4—C10120.99 (15)C8—C9—C10119.09 (17)
C3—C4—H4120.6 (12)C1—C9—C10119.39 (16)
C10—C4—H4118.4 (12)C5—C10—C4122.08 (16)
C6—C5—C10120.37 (18)C5—C10—C9119.07 (17)
C6—C5—H5119.2 (12)C4—C10—C9118.85 (16)
C10—C5—H5120.3 (12)N1—C11—C3179.5 (2)
C5—C6—C7120.70 (19)N2—C12—C2178.9 (2)
C9—C1—C2—C30.3 (3)C7—C8—C9—C100.6 (3)
C9—C1—C2—C12179.22 (17)C2—C1—C9—C8179.82 (18)
C1—C2—C3—C41.2 (3)C2—C1—C9—C100.4 (3)
C12—C2—C3—C4178.34 (18)C6—C5—C10—C4179.41 (18)
C1—C2—C3—C11179.20 (18)C6—C5—C10—C90.1 (3)
C12—C2—C3—C111.3 (3)C3—C4—C10—C5179.76 (18)
C2—C3—C4—C101.4 (3)C3—C4—C10—C90.7 (3)
C11—C3—C4—C10179.00 (17)C8—C9—C10—C50.4 (3)
C10—C5—C6—C70.5 (3)C1—C9—C10—C5179.37 (18)
C5—C6—C7—C80.3 (3)C8—C9—C10—C4179.98 (18)
C6—C7—C8—C90.3 (3)C1—C9—C10—C40.2 (3)
C7—C8—C9—C1179.15 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···N1i0.99 (2)2.57 (2)3.487 (2)154.7 (16)
C4—H4···N2ii0.97 (2)2.63 (2)3.496 (3)148.6 (16)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y1/2, z+1/2.
 

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