



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033521/gg2021sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033521/gg2021Isup2.hkl |
CCDC reference: 674446
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.032
- wR factor = 0.091
- Data-to-parameter ratio = 9.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.68 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT432_ALERT_2_C Short Inter X...Y Contact C6 .. C10 .. 3.18 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. C3 .. 2.93 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H10 .. C6 .. 2.97 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. N1 .. 2.89 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 .. C18 .. 2.96 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13 .. C18 .. 2.98 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 .. N2 .. 2.82 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H17 .. C1 .. 2.99 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H17 .. C8 .. 2.86 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H18 .. N1 .. 2.81 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for C10 .. C6 .. 93.10 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 10 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A 50 ml round-bottomed flask was charged with biphenyl-3,3',4,4'-tetramine (214 mg, 1 mmol), benzil (420 mg, 2 mmol), iodine (51 mg, 0.2 mmol), and acetonitrile (15 ml). The reaction was monitored by thin-layer chromatography until complete consumption of the starting materials (15 min). The resulting amber solution was concentrated to dryness under reduced pressure. The dark-brown crude product was then subjected to flash column chromatography using silica gel (eluent: 9:1 hexane–EtOAc) in order to remove residual iodine. The pale-yellow solution was evaporated to dryness under reduced pressure to give (I) (yield 0.413 mg, 74%), as a white powder (m.p. 573 K). This powder was then crystallized from a minimal amount of toluene, and afforded (I) as pale-yellow cubes.
H atoms were placed in idealized positions (C—H = 0.96 – 1.00 A) and allowed to ride on their parent atoms with Uiso(H) = 1.2 Ueq(C).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: XSHELL (Bruker, 2004); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C40H26N4 | Z = 1 |
Mr = 562.65 | F(000) = 294 |
Triclinic, P1 | Dx = 1.327 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54178 Å |
a = 5.7024 (1) Å | Cell parameters from 585 reflections |
b = 9.9534 (2) Å | θ = 3.6–67.0° |
c = 12.9785 (3) Å | µ = 0.61 mm−1 |
α = 105.352 (1)° | T = 100 K |
β = 96.617 (1)° | Block, colourless |
γ = 91.751 (1)° | 0.19 × 0.12 × 0.06 mm |
V = 704.19 (3) Å3 |
Bruker SMART APEXII CCD diffractometer | 2429 independent reflections |
Radiation source: fine-focus sealed tube | 2156 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω and ψ scans | θmax = 67.0°, θmin = 3.6° |
Absorption correction: numerical (SADABS; Sheldrick, 2004) | h = −6→6 |
Tmin = 0.893, Tmax = 0.964 | k = −11→11 |
12179 measured reflections | l = −15→15 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0496P)2 + 0.1323P] where P = (Fo2 + 2Fc2)/3 |
2429 reflections | (Δ/σ)max < 0.001 |
251 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C40H26N4 | γ = 91.751 (1)° |
Mr = 562.65 | V = 704.19 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 5.7024 (1) Å | Cu Kα radiation |
b = 9.9534 (2) Å | µ = 0.61 mm−1 |
c = 12.9785 (3) Å | T = 100 K |
α = 105.352 (1)° | 0.19 × 0.12 × 0.06 mm |
β = 96.617 (1)° |
Bruker SMART APEXII CCD diffractometer | 2429 independent reflections |
Absorption correction: numerical (SADABS; Sheldrick, 2004) | 2156 reflections with I > 2σ(I) |
Tmin = 0.893, Tmax = 0.964 | Rint = 0.033 |
12179 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.091 | All H-atom parameters refined |
S = 1.06 | Δρmax = 0.23 e Å−3 |
2429 reflections | Δρmin = −0.18 e Å−3 |
251 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.51854 (16) | 0.85128 (10) | 0.69940 (8) | 0.0221 (2) | |
N2 | 0.23046 (17) | 0.60236 (10) | 0.64109 (8) | 0.0224 (2) | |
C1 | 0.03603 (19) | 0.94087 (11) | 0.52202 (9) | 0.0209 (3) | |
C2 | 0.2496 (2) | 0.94755 (12) | 0.58600 (9) | 0.0226 (3) | |
C3 | 0.31629 (19) | 0.83612 (11) | 0.62942 (9) | 0.0211 (3) | |
C4 | 0.57593 (19) | 0.74558 (12) | 0.73939 (9) | 0.0212 (3) | |
C5 | 0.43238 (19) | 0.61520 (12) | 0.70434 (9) | 0.0211 (3) | |
C6 | 0.1661 (2) | 0.71321 (12) | 0.60385 (9) | 0.0217 (3) | |
C7 | −0.0511 (2) | 0.70597 (12) | 0.53726 (9) | 0.0231 (3) | |
C8 | −0.1142 (2) | 0.81609 (12) | 0.49890 (9) | 0.0225 (3) | |
C9 | 0.79004 (19) | 0.77207 (11) | 0.82117 (9) | 0.0219 (3) | |
C10 | 0.9637 (2) | 0.87320 (12) | 0.81830 (10) | 0.0239 (3) | |
C11 | 1.1675 (2) | 0.90121 (13) | 0.89186 (10) | 0.0269 (3) | |
C12 | 1.2013 (2) | 0.82934 (13) | 0.97005 (10) | 0.0288 (3) | |
C13 | 1.0272 (2) | 0.73173 (13) | 0.97578 (10) | 0.0281 (3) | |
C14 | 0.8232 (2) | 0.70364 (12) | 0.90232 (10) | 0.0252 (3) | |
C15 | 0.49998 (19) | 0.48375 (11) | 0.73197 (9) | 0.0215 (3) | |
C16 | 0.7014 (2) | 0.41920 (12) | 0.69865 (9) | 0.0240 (3) | |
C17 | 0.7507 (2) | 0.29096 (12) | 0.71734 (10) | 0.0248 (3) | |
C18 | 0.6025 (2) | 0.22840 (12) | 0.77110 (9) | 0.0244 (3) | |
C19 | 0.4035 (2) | 0.29355 (13) | 0.80581 (10) | 0.0268 (3) | |
C20 | 0.3503 (2) | 0.42037 (12) | 0.78536 (10) | 0.0247 (3) | |
H2 | 0.361 (3) | 1.0290 (16) | 0.6039 (12) | 0.035 (4)* | |
H7 | −0.153 (3) | 0.6200 (16) | 0.5199 (12) | 0.035 (4)* | |
H8 | −0.267 (2) | 0.8096 (13) | 0.4535 (11) | 0.021 (3)* | |
H10 | 0.938 (2) | 0.9233 (14) | 0.7633 (11) | 0.026 (3)* | |
H11 | 1.287 (3) | 0.9694 (15) | 0.8870 (12) | 0.033 (4)* | |
H12 | 1.344 (3) | 0.8484 (16) | 1.0224 (12) | 0.036 (4)* | |
H13 | 1.048 (2) | 0.6786 (16) | 1.0312 (13) | 0.037 (4)* | |
H14 | 0.698 (3) | 0.6366 (16) | 0.9090 (12) | 0.033 (4)* | |
H16 | 0.807 (2) | 0.4646 (15) | 0.6621 (12) | 0.029 (3)* | |
H17 | 0.888 (2) | 0.2451 (14) | 0.6924 (11) | 0.023 (3)* | |
H18 | 0.640 (2) | 0.1387 (15) | 0.7834 (11) | 0.028 (3)* | |
H19 | 0.296 (2) | 0.2499 (15) | 0.8440 (12) | 0.033 (4)* | |
H20 | 0.210 (3) | 0.4660 (15) | 0.8084 (12) | 0.032 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0212 (5) | 0.0209 (5) | 0.0245 (5) | 0.0010 (4) | 0.0015 (4) | 0.0073 (4) |
N2 | 0.0241 (5) | 0.0195 (5) | 0.0240 (5) | 0.0010 (4) | 0.0019 (4) | 0.0070 (4) |
C1 | 0.0227 (6) | 0.0196 (6) | 0.0205 (6) | 0.0010 (5) | 0.0037 (4) | 0.0052 (4) |
C2 | 0.0228 (6) | 0.0193 (6) | 0.0258 (6) | −0.0015 (5) | 0.0015 (4) | 0.0073 (5) |
C3 | 0.0204 (6) | 0.0208 (6) | 0.0216 (6) | 0.0006 (5) | 0.0027 (4) | 0.0049 (4) |
C4 | 0.0219 (6) | 0.0196 (5) | 0.0231 (6) | 0.0019 (4) | 0.0047 (4) | 0.0067 (4) |
C5 | 0.0204 (5) | 0.0208 (6) | 0.0224 (6) | 0.0010 (4) | 0.0035 (4) | 0.0060 (4) |
C6 | 0.0243 (6) | 0.0189 (5) | 0.0217 (6) | 0.0012 (5) | 0.0038 (4) | 0.0051 (4) |
C7 | 0.0238 (6) | 0.0199 (6) | 0.0244 (6) | −0.0024 (5) | 0.0005 (4) | 0.0053 (4) |
C8 | 0.0224 (6) | 0.0217 (6) | 0.0227 (6) | −0.0013 (5) | 0.0003 (4) | 0.0058 (4) |
C9 | 0.0207 (6) | 0.0187 (5) | 0.0249 (6) | 0.0033 (4) | 0.0025 (4) | 0.0034 (4) |
C10 | 0.0247 (6) | 0.0207 (6) | 0.0260 (6) | 0.0034 (5) | 0.0037 (5) | 0.0057 (5) |
C11 | 0.0227 (6) | 0.0256 (6) | 0.0302 (7) | −0.0002 (5) | 0.0041 (5) | 0.0036 (5) |
C12 | 0.0224 (6) | 0.0343 (7) | 0.0261 (6) | 0.0014 (5) | −0.0025 (5) | 0.0042 (5) |
C13 | 0.0279 (6) | 0.0295 (6) | 0.0270 (6) | 0.0038 (5) | 0.0002 (5) | 0.0087 (5) |
C14 | 0.0248 (6) | 0.0235 (6) | 0.0262 (6) | 0.0008 (5) | 0.0015 (5) | 0.0058 (5) |
C15 | 0.0218 (6) | 0.0185 (5) | 0.0225 (6) | −0.0011 (4) | −0.0023 (4) | 0.0050 (4) |
C16 | 0.0240 (6) | 0.0229 (6) | 0.0258 (6) | 0.0002 (5) | 0.0034 (5) | 0.0077 (5) |
C17 | 0.0238 (6) | 0.0225 (6) | 0.0264 (6) | 0.0041 (5) | 0.0008 (5) | 0.0045 (5) |
C18 | 0.0285 (6) | 0.0180 (5) | 0.0253 (6) | 0.0009 (5) | −0.0048 (5) | 0.0069 (4) |
C19 | 0.0260 (6) | 0.0259 (6) | 0.0310 (7) | −0.0011 (5) | 0.0017 (5) | 0.0131 (5) |
C20 | 0.0206 (6) | 0.0248 (6) | 0.0296 (6) | 0.0023 (5) | 0.0030 (5) | 0.0089 (5) |
N1—C4 | 1.3245 (15) | C10—H10 | 0.974 (14) |
N1—C3 | 1.3613 (14) | C11—C12 | 1.3880 (18) |
N2—C5 | 1.3166 (15) | C11—H11 | 0.966 (15) |
N2—C6 | 1.3609 (15) | C12—C13 | 1.3899 (18) |
C1—C2 | 1.3819 (16) | C12—H12 | 0.978 (15) |
C1—C8 | 1.4301 (16) | C13—C14 | 1.3870 (17) |
C1—C1i | 1.488 (2) | C13—H13 | 0.998 (15) |
C2—C3 | 1.4141 (16) | C14—H14 | 0.988 (15) |
C2—H2 | 0.976 (15) | C15—C16 | 1.3898 (17) |
C3—C6 | 1.4129 (16) | C15—C20 | 1.3936 (16) |
C4—C5 | 1.4484 (16) | C16—C17 | 1.3918 (16) |
C4—C9 | 1.4900 (15) | C16—H16 | 0.976 (14) |
C5—C15 | 1.4955 (15) | C17—C18 | 1.3865 (17) |
C6—C7 | 1.4143 (16) | C17—H17 | 0.962 (14) |
C7—C8 | 1.3604 (16) | C18—C19 | 1.3852 (18) |
C7—H7 | 0.977 (15) | C18—H18 | 0.973 (14) |
C8—H8 | 0.986 (13) | C19—C20 | 1.3922 (16) |
C9—C14 | 1.3967 (17) | C19—H19 | 0.990 (15) |
C9—C10 | 1.4010 (16) | C20—H20 | 0.971 (15) |
C10—C11 | 1.3868 (17) | ||
C4—N1—C3 | 118.29 (10) | C9—C10—H10 | 118.5 (8) |
C5—N2—C6 | 117.97 (10) | C12—C11—C10 | 120.12 (11) |
C2—C1—C8 | 117.90 (10) | C12—C11—H11 | 120.4 (8) |
C2—C1—C1i | 121.33 (13) | C10—C11—H11 | 119.4 (8) |
C8—C1—C1i | 120.76 (12) | C11—C12—C13 | 119.59 (11) |
C1—C2—C3 | 121.34 (11) | C11—C12—H12 | 120.8 (9) |
C1—C2—H2 | 122.0 (8) | C13—C12—H12 | 119.6 (9) |
C3—C2—H2 | 116.6 (9) | C14—C13—C12 | 120.35 (11) |
N1—C3—C6 | 120.83 (10) | C14—C13—H13 | 118.8 (9) |
N1—C3—C2 | 119.57 (10) | C12—C13—H13 | 120.9 (9) |
C6—C3—C2 | 119.52 (10) | C13—C14—C9 | 120.67 (11) |
N1—C4—C5 | 120.22 (10) | C13—C14—H14 | 119.5 (8) |
N1—C4—C9 | 115.70 (10) | C9—C14—H14 | 119.8 (8) |
C5—C4—C9 | 124.07 (10) | C16—C15—C20 | 119.65 (10) |
N2—C5—C4 | 121.55 (10) | C16—C15—C5 | 120.82 (10) |
N2—C5—C15 | 114.09 (10) | C20—C15—C5 | 119.38 (10) |
C4—C5—C15 | 124.33 (10) | C15—C16—C17 | 119.93 (11) |
N2—C6—C3 | 120.68 (10) | C15—C16—H16 | 119.3 (8) |
N2—C6—C7 | 120.32 (10) | C17—C16—H16 | 120.8 (8) |
C3—C6—C7 | 118.99 (10) | C18—C17—C16 | 120.38 (11) |
C8—C7—C6 | 120.36 (11) | C18—C17—H17 | 119.8 (8) |
C8—C7—H7 | 121.6 (9) | C16—C17—H17 | 119.8 (8) |
C6—C7—H7 | 118.1 (9) | C19—C18—C17 | 119.78 (11) |
C7—C8—C1 | 121.85 (11) | C19—C18—H18 | 121.0 (8) |
C7—C8—H8 | 119.2 (7) | C17—C18—H18 | 119.2 (8) |
C1—C8—H8 | 119.0 (7) | C18—C19—C20 | 120.18 (11) |
C14—C9—C10 | 118.36 (11) | C18—C19—H19 | 120.6 (8) |
C14—C9—C4 | 123.20 (10) | C20—C19—H19 | 119.2 (8) |
C10—C9—C4 | 118.42 (10) | C15—C20—C19 | 120.05 (11) |
C11—C10—C9 | 120.85 (11) | C15—C20—H20 | 119.3 (8) |
C11—C10—H10 | 120.7 (8) | C19—C20—H20 | 120.7 (8) |
C8—C1—C2—C3 | −1.34 (17) | N1—C4—C9—C14 | 152.27 (11) |
C1i—C1—C2—C3 | 178.88 (12) | C5—C4—C9—C14 | −26.95 (17) |
C4—N1—C3—C6 | 2.79 (16) | N1—C4—C9—C10 | −25.98 (15) |
C4—N1—C3—C2 | 179.56 (10) | C5—C4—C9—C10 | 154.81 (11) |
C1—C2—C3—N1 | −174.44 (10) | C14—C9—C10—C11 | 2.26 (17) |
C1—C2—C3—C6 | 2.37 (17) | C4—C9—C10—C11 | −179.41 (10) |
C3—N1—C4—C5 | 3.29 (16) | C9—C10—C11—C12 | −0.35 (18) |
C3—N1—C4—C9 | −175.95 (9) | C10—C11—C12—C13 | −1.57 (19) |
C6—N2—C5—C4 | 3.88 (16) | C11—C12—C13—C14 | 1.55 (19) |
C6—N2—C5—C15 | −174.05 (9) | C12—C13—C14—C9 | 0.41 (18) |
N1—C4—C5—N2 | −6.97 (17) | C10—C9—C14—C13 | −2.28 (17) |
C9—C4—C5—N2 | 172.21 (10) | C4—C9—C14—C13 | 179.47 (10) |
N1—C4—C5—C15 | 170.75 (10) | N2—C5—C15—C16 | 115.78 (12) |
C9—C4—C5—C15 | −10.07 (17) | C4—C5—C15—C16 | −62.09 (15) |
C5—N2—C6—C3 | 2.27 (16) | N2—C5—C15—C20 | −59.79 (14) |
C5—N2—C6—C7 | −178.84 (10) | C4—C5—C15—C20 | 122.33 (12) |
N1—C3—C6—N2 | −5.86 (17) | C20—C15—C16—C17 | 0.92 (17) |
C2—C3—C6—N2 | 177.37 (10) | C5—C15—C16—C17 | −174.64 (10) |
N1—C3—C6—C7 | 175.23 (10) | C15—C16—C17—C18 | −1.36 (18) |
C2—C3—C6—C7 | −1.54 (16) | C16—C17—C18—C19 | 0.39 (17) |
N2—C6—C7—C8 | −179.17 (10) | C17—C18—C19—C20 | 1.01 (18) |
C3—C6—C7—C8 | −0.26 (17) | C16—C15—C20—C19 | 0.46 (18) |
C6—C7—C8—C1 | 1.31 (18) | C5—C15—C20—C19 | 176.09 (10) |
C2—C1—C8—C7 | −0.51 (17) | C18—C19—C20—C15 | −1.44 (18) |
C1i—C1—C8—C7 | 179.27 (13) |
Symmetry code: (i) −x, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···C18ii | 0.977 (15) | 2.722 (15) | 3.5521 (16) | 143.1 (12) |
C7—H7···N2iii | 0.979 (15) | 2.593 (16) | 3.3635 (15) | 135.6 (11) |
C10—H10···C3iv | 0.974 (13) | 2.935 (12) | 3.2994 (15) | 103.4 (8) |
C10—H10···C6iv | 0.974 (13) | 2.974 (13) | 3.1801 (15) | 93.1 (8) |
C11—H11···N1iv | 0.963 (15) | 2.893 (14) | 3.3233 (14) | 108.3 (10) |
C12—H12···C18v | 0.975 (15) | 2.959 (15) | 3.6146 (16) | 125.6 (10) |
C13—H13···C18v | 0.999 (15) | 2.978 (15) | 3.6141 (16) | 122.5 (10) |
C16—H16···N2iv | 0.978 (14) | 2.815 (14) | 3.7256 (14) | 155.2 (11) |
C17—H17···C1vi | 0.969 (13) | 2.993 (14) | 3.7019 (16) | 131.0 (9) |
C17—H17···C8vi | 0.969 (13) | 2.860 (14) | 3.6338 (15) | 137.5 (9) |
C18—H18···N1vii | 0.975 (14) | 2.808 (14) | 3.6217 (14) | 141.5 (10) |
Symmetry codes: (ii) x, y+1, z; (iii) −x, −y+1, −z+1; (iv) x+1, y, z; (v) −x+2, −y+1, −z+2; (vi) −x+1, −y+1, −z+1; (vii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C40H26N4 |
Mr | 562.65 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 5.7024 (1), 9.9534 (2), 12.9785 (3) |
α, β, γ (°) | 105.352 (1), 96.617 (1), 91.751 (1) |
V (Å3) | 704.19 (3) |
Z | 1 |
Radiation type | Cu Kα |
µ (mm−1) | 0.61 |
Crystal size (mm) | 0.19 × 0.12 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD |
Absorption correction | Numerical (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.893, 0.964 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12179, 2429, 2156 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.091, 1.06 |
No. of reflections | 2429 |
No. of parameters | 251 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.23, −0.18 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SAINT-Plus, SHELXS97 (Sheldrick, 1997), XSHELL (Bruker, 2004), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···C18i | 0.977 (15) | 2.722 (15) | 3.5521 (16) | 143.1 (12) |
C7—H7···N2ii | 0.979 (15) | 2.593 (16) | 3.3635 (15) | 135.6 (11) |
C10—H10···C3iii | 0.974 (13) | 2.935 (12) | 3.2994 (15) | 103.4 (8) |
C10—H10···C6iii | 0.974 (13) | 2.974 (13) | 3.1801 (15) | 93.1 (8) |
C11—H11···N1iii | 0.963 (15) | 2.893 (14) | 3.3233 (14) | 108.3 (10) |
C12—H12···C18iv | 0.975 (15) | 2.959 (15) | 3.6146 (16) | 125.6 (10) |
C13—H13···C18iv | 0.999 (15) | 2.978 (15) | 3.6141 (16) | 122.5 (10) |
C16—H16···N2iii | 0.978 (14) | 2.815 (14) | 3.7256 (14) | 155.2 (11) |
C17—H17···C1v | 0.969 (13) | 2.993 (14) | 3.7019 (16) | 131.0 (9) |
C17—H17···C8v | 0.969 (13) | 2.860 (14) | 3.6338 (15) | 137.5 (9) |
C18—H18···N1vi | 0.975 (14) | 2.808 (14) | 3.6217 (14) | 141.5 (10) |
Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z+1; (iii) x+1, y, z; (iv) −x+2, −y+1, −z+2; (v) −x+1, −y+1, −z+1; (vi) x, y−1, z. |
Quinoxalines and their derivatives have received considerable attention in the past several years due to their electronic properties (Page et al., 1998; Simpson & Gordon, 1995), H-bonding ability (Pascal et al., 1993; Wozniak et al., 1993), and their capacity to coordinate to metals forming interesting three-dimensional structures (Wu et al., 2002; Willett et al., 2001). During our investigations, we have prepared a number of substituted quinoxalines and phenazines, some of which coordinate to metal salts forming novel structures (Dueno, et al., unpublished). Our current work involves the synthesis of new nitrogen heterocycles (Gibson, et al., 2006; Salvatore, et al., 2006) which may lead to novel three dimensional structures upon coordination to metal salts. Here, we report the crystal structure of 2,2',3,3'-Tetraphenyl-7,7'-biquinoxaline (I), (Figure 1).
The structure of (I) has bond distances and angles that are unexceptional, as all fall within ranges found in the literature for similar nitrogen heterocycles (Brown et al., 2004). The one molecule present in the asymmetric unit cell lies on an inversion center, so that half the molecule is related to its counterpart by symmetry (symmetry code, -x,-y,-z). As expected, the steric bulk of the phenyl substituents prevents them from being coplanar with the quinoxaline rings: the dihedral angle N2—C5—C15—C20 (phenyl ring 1) is 59.80 (11)°, and the dihedral angle N1—C4—C9—C10 (phenyl ring 2) is 25.98 (11)°. An interesting feature worth mentioning is that the two rings that make up the quinoxaline unit are not perfectly planar, for the angle between the N containing ring and the carbon-only ring is 3.50 (11)° (based on a least squares mean planes of N1—C4—C5—N2—C6—C3 and C1—C2—C3—C6—C7—C8). It is conceivable that this deviation from a planar structure is due to Van der Waals repulsion interactions between the aromatic substituents. Another interesting aspect of this molecule is that the packing diagram shows short contact interactions between phenyl substituents on one molecule and the quinoxaline ring of an adjacent molecule. Intermolecular distances range from 3.181 (2) Å (C10—C6) to 3.376 (2) Å (C11—C4), which suggests some degree of σ(CH)···π interaction (Figure 2).