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In the title compound, C33H25N5, the central benzene ring is not coplanar with any other rings. The mol­ecules are linked through an inter­molecular C—H...N hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807005533/om2095sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807005533/om2095Isup2.hkl
Contains datablock I

CCDC reference: 640432

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.068
  • wR factor = 0.095
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.152 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.15 PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 33 Perc.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.82 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

2-[4-(Diethylamino)phenyl]-1-ethylimidazo[4,5-f][1,10]phenanthroline top
Crystal data top
C33H25N5F(000) = 1032
Mr = 491.58Dx = 1.271 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 18.412 (2) ÅCell parameters from 881 reflections
b = 15.396 (2) Åθ = 2.6–22.3°
c = 9.236 (1) ŵ = 0.08 mm1
β = 101.02 (1)°T = 298 K
V = 2569.9 (5) Å3Needle, yellow
Z = 40.38 × 0.10 × 0.08 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4422 independent reflections
Radiation source: fine-focus sealed tube1458 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.152
ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2121
Tmin = 0.932, Tmax = 0.997k = 1816
11297 measured reflectionsl = 107
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.0123P)2]
where P = (Fo2 + 2Fc2)/3
4422 reflections(Δ/σ)max < 0.001
343 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.18 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
N10.5650 (2)1.1537 (3)0.3624 (4)0.0535 (12)
N20.4671 (2)1.2641 (3)0.4479 (4)0.0584 (13)
N30.3633 (2)0.9339 (2)0.2951 (4)0.0367 (10)
N40.28551 (19)1.0265 (2)0.3744 (4)0.0409 (11)
N50.0873 (2)0.6704 (3)0.2891 (4)0.0595 (13)
C10.6142 (3)1.1007 (4)0.3215 (5)0.0573 (17)
H1A0.66131.12230.32020.069*
C20.5995 (3)1.0150 (4)0.2805 (5)0.0543 (15)
H2A0.63620.98030.25420.065*
C30.5305 (3)0.9822 (3)0.2794 (4)0.0465 (14)
H3A0.51960.92480.25260.056*
C40.4763 (3)1.0364 (3)0.3192 (4)0.0355 (13)
C50.4011 (2)1.0120 (3)0.3241 (4)0.0359 (13)
C60.3517 (2)1.0671 (3)0.3714 (5)0.0363 (13)
C70.3721 (3)1.1539 (3)0.4183 (5)0.0407 (13)
C80.3243 (3)1.2116 (3)0.4710 (5)0.0543 (15)
H8A0.27711.19400.47980.065*
C90.3481 (3)1.2944 (3)0.5097 (5)0.0636 (17)
H9A0.31761.33440.54410.076*
C100.4197 (3)1.3161 (3)0.4953 (5)0.0668 (18)
H10A0.43561.37230.52140.080*
C110.4434 (3)1.1819 (3)0.4105 (5)0.0438 (14)
C120.4968 (3)1.1231 (3)0.3619 (5)0.0407 (13)
C130.3838 (2)0.8607 (3)0.2068 (5)0.0469 (14)
H13A0.34890.81350.20630.056*
H13B0.43260.83960.25170.056*
C140.3841 (2)0.8887 (3)0.0501 (4)0.0606 (16)
H14A0.39730.84030.00490.091*
H14B0.41940.93460.05040.091*
H14C0.33570.90910.00530.091*
C150.2947 (3)0.9468 (3)0.3274 (5)0.0382 (13)
C160.2396 (2)0.8765 (3)0.3204 (5)0.0371 (13)
C170.2592 (2)0.7969 (3)0.3866 (4)0.0455 (14)
H17A0.30760.78790.43600.055*
C180.2080 (3)0.7310 (3)0.3801 (5)0.0511 (14)
H18A0.22170.67830.42670.061*
C190.1363 (3)0.7429 (3)0.3045 (5)0.0460 (14)
C200.1150 (2)0.8229 (3)0.2419 (5)0.0522 (15)
H20A0.06660.83210.19350.063*
C210.1667 (3)0.8890 (3)0.2522 (5)0.0510 (15)
H21A0.15200.94310.21230.061*
C220.1177 (3)0.5863 (4)0.2774 (6)0.0520 (15)
C230.1605 (3)0.5721 (4)0.1730 (5)0.0578 (16)
H23A0.16720.61650.10860.069*
C240.1938 (3)0.4920 (5)0.1631 (6)0.082 (2)
H24A0.22240.48260.09170.098*
C250.1844 (4)0.4282 (4)0.2571 (8)0.100 (2)
H25A0.20860.37550.25320.120*
C260.1396 (4)0.4395 (4)0.3589 (7)0.097 (2)
H26A0.13150.39390.41990.116*
C270.1065 (3)0.5201 (4)0.3696 (6)0.0729 (18)
H27A0.07690.52880.43930.088*
C280.0114 (3)0.6782 (3)0.2908 (5)0.0497 (14)
C290.0392 (3)0.6215 (3)0.2071 (5)0.0615 (16)
H29A0.02290.58030.14700.074*
C300.1136 (3)0.6267 (4)0.2136 (6)0.0714 (19)
H30A0.14680.58830.15850.086*
C310.1386 (3)0.6871 (4)0.2993 (7)0.0726 (19)
H31A0.18880.69070.30140.087*
C320.0893 (3)0.7429 (4)0.3831 (6)0.0732 (18)
H32A0.10630.78400.44260.088*
C330.0145 (3)0.7381 (3)0.3792 (5)0.0601 (16)
H33A0.01850.77570.43680.072*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.049 (3)0.054 (4)0.056 (3)0.014 (3)0.007 (2)0.006 (2)
N20.068 (3)0.045 (3)0.062 (3)0.018 (3)0.014 (3)0.011 (3)
N30.032 (3)0.028 (3)0.050 (3)0.001 (2)0.007 (2)0.003 (2)
N40.032 (3)0.031 (3)0.059 (3)0.002 (2)0.007 (2)0.000 (2)
N50.038 (3)0.040 (3)0.100 (4)0.010 (3)0.012 (2)0.006 (3)
C10.036 (4)0.078 (5)0.056 (4)0.022 (4)0.003 (3)0.000 (3)
C20.038 (4)0.068 (5)0.056 (4)0.003 (3)0.008 (3)0.002 (3)
C30.047 (3)0.047 (4)0.043 (3)0.002 (3)0.002 (3)0.003 (3)
C40.035 (3)0.037 (4)0.034 (3)0.001 (3)0.005 (2)0.004 (2)
C50.036 (3)0.030 (4)0.039 (3)0.008 (3)0.002 (2)0.002 (2)
C60.035 (3)0.028 (4)0.043 (3)0.002 (3)0.000 (3)0.001 (3)
C70.045 (3)0.036 (4)0.040 (3)0.007 (3)0.007 (3)0.003 (3)
C80.052 (4)0.049 (4)0.063 (4)0.007 (3)0.013 (3)0.004 (3)
C90.076 (5)0.038 (4)0.080 (4)0.001 (3)0.022 (4)0.009 (3)
C100.094 (5)0.034 (4)0.073 (4)0.016 (4)0.018 (4)0.016 (3)
C110.055 (4)0.032 (4)0.044 (3)0.011 (3)0.009 (3)0.001 (3)
C120.037 (3)0.046 (4)0.037 (3)0.011 (3)0.002 (3)0.002 (3)
C130.046 (3)0.028 (4)0.068 (4)0.005 (3)0.014 (3)0.009 (3)
C140.067 (4)0.061 (4)0.055 (4)0.005 (3)0.014 (3)0.013 (3)
C150.031 (3)0.032 (4)0.047 (4)0.006 (3)0.005 (3)0.002 (3)
C160.029 (3)0.034 (4)0.049 (4)0.002 (3)0.006 (3)0.006 (3)
C170.037 (3)0.035 (4)0.061 (4)0.000 (3)0.002 (3)0.003 (3)
C180.045 (4)0.034 (4)0.071 (4)0.004 (3)0.002 (3)0.012 (3)
C190.037 (3)0.039 (4)0.060 (4)0.012 (3)0.006 (3)0.003 (3)
C200.037 (3)0.042 (4)0.070 (4)0.005 (3)0.009 (3)0.007 (3)
C210.051 (4)0.031 (4)0.069 (4)0.000 (3)0.006 (3)0.003 (3)
C220.055 (4)0.046 (4)0.054 (4)0.018 (3)0.010 (3)0.003 (3)
C230.061 (4)0.045 (5)0.066 (4)0.009 (3)0.008 (3)0.002 (3)
C240.079 (5)0.074 (6)0.094 (6)0.012 (5)0.019 (4)0.026 (4)
C250.110 (6)0.051 (6)0.137 (8)0.009 (5)0.016 (5)0.017 (5)
C260.139 (7)0.052 (5)0.098 (6)0.007 (5)0.020 (5)0.021 (4)
C270.090 (5)0.062 (5)0.068 (4)0.008 (4)0.019 (4)0.000 (4)
C280.047 (4)0.044 (4)0.057 (4)0.010 (3)0.006 (3)0.003 (3)
C290.057 (4)0.051 (4)0.074 (4)0.016 (3)0.006 (3)0.006 (3)
C300.058 (5)0.071 (5)0.078 (5)0.033 (4)0.005 (4)0.012 (4)
C310.045 (4)0.093 (6)0.080 (5)0.008 (4)0.012 (4)0.016 (4)
C320.067 (4)0.085 (5)0.070 (5)0.001 (4)0.019 (4)0.004 (4)
C330.041 (4)0.066 (5)0.072 (4)0.011 (3)0.008 (3)0.005 (3)
Geometric parameters (Å, º) top
N1—C11.326 (5)C14—H14C0.9600
N1—C121.340 (5)C15—C161.477 (5)
N2—C101.319 (5)C16—C211.382 (5)
N2—C111.362 (5)C16—C171.386 (5)
N3—C151.366 (5)C17—C181.380 (5)
N3—C51.390 (5)C17—H17A0.9300
N3—C131.481 (4)C18—C191.383 (5)
N4—C151.323 (5)C18—H18A0.9300
N4—C61.374 (5)C19—C201.384 (5)
N5—C281.405 (5)C20—C211.384 (5)
N5—C221.423 (5)C20—H20A0.9300
N5—C191.425 (5)C21—H21A0.9300
C1—C21.384 (6)C22—C271.369 (6)
C1—H1A0.9300C22—C231.374 (6)
C2—C31.365 (5)C23—C241.388 (6)
C2—H2A0.9300C23—H23A0.9300
C3—C41.403 (5)C24—C251.344 (7)
C3—H3A0.9300C24—H24A0.9300
C4—C121.422 (5)C25—C261.375 (7)
C4—C51.444 (5)C25—H25A0.9300
C5—C61.375 (5)C26—C271.394 (7)
C6—C71.432 (5)C26—H26A0.9300
C7—C111.397 (6)C27—H27A0.9300
C7—C81.401 (5)C28—C331.376 (6)
C8—C91.374 (6)C28—C291.396 (5)
C8—H8A0.9300C29—C301.385 (6)
C9—C101.391 (6)C29—H29A0.9300
C9—H9A0.9300C30—C311.357 (6)
C10—H10A0.9300C30—H30A0.9300
C11—C121.468 (6)C31—C321.375 (6)
C13—C141.510 (4)C31—H31A0.9300
C13—H13A0.9700C32—C331.388 (6)
C13—H13B0.9700C32—H32A0.9300
C14—H14A0.9600C33—H33A0.9300
C14—H14B0.9600
C1—N1—C12118.3 (5)N4—C15—N3112.8 (4)
C10—N2—C11116.6 (5)N4—C15—C16124.3 (5)
C15—N3—C5106.4 (4)N3—C15—C16122.7 (5)
C15—N3—C13125.1 (4)C21—C16—C17118.2 (5)
C5—N3—C13126.3 (4)C21—C16—C15121.1 (5)
C15—N4—C6104.2 (4)C17—C16—C15120.6 (4)
C28—N5—C22119.0 (5)C18—C17—C16120.8 (4)
C28—N5—C19123.0 (5)C18—C17—H17A119.6
C22—N5—C19118.0 (4)C16—C17—H17A119.6
N1—C1—C2123.7 (5)C17—C18—C19120.2 (5)
N1—C1—H1A118.2C17—C18—H18A119.9
C2—C1—H1A118.2C19—C18—H18A119.9
C3—C2—C1119.2 (5)C18—C19—C20119.7 (5)
C3—C2—H2A120.4C18—C19—N5118.1 (5)
C1—C2—H2A120.4C20—C19—N5122.2 (5)
C2—C3—C4119.0 (5)C19—C20—C21119.4 (4)
C2—C3—H3A120.5C19—C20—H20A120.3
C4—C3—H3A120.5C21—C20—H20A120.3
C3—C4—C12117.8 (5)C16—C21—C20121.5 (5)
C3—C4—C5126.0 (5)C16—C21—H21A119.2
C12—C4—C5116.2 (4)C20—C21—H21A119.2
C6—C5—N3104.9 (4)C27—C22—C23119.5 (6)
C6—C5—C4123.1 (5)C27—C22—N5121.5 (6)
N3—C5—C4131.9 (5)C23—C22—N5119.0 (5)
N4—C6—C5111.6 (4)C22—C23—C24120.5 (5)
N4—C6—C7126.9 (5)C22—C23—H23A119.8
C5—C6—C7121.4 (5)C24—C23—H23A119.8
C11—C7—C8118.7 (5)C25—C24—C23119.6 (6)
C11—C7—C6117.9 (5)C25—C24—H24A120.2
C8—C7—C6123.4 (5)C23—C24—H24A120.2
C9—C8—C7119.3 (5)C24—C25—C26121.2 (7)
C9—C8—H8A120.4C24—C25—H25A119.4
C7—C8—H8A120.4C26—C25—H25A119.4
C8—C9—C10117.3 (5)C25—C26—C27119.2 (6)
C8—C9—H9A121.3C25—C26—H26A120.4
C10—C9—H9A121.3C27—C26—H26A120.4
N2—C10—C9125.8 (5)C22—C27—C26119.9 (6)
N2—C10—H10A117.1C22—C27—H27A120.0
C9—C10—H10A117.1C26—C27—H27A120.0
N2—C11—C7122.2 (5)C33—C28—C29118.5 (5)
N2—C11—C12116.7 (5)C33—C28—N5121.4 (5)
C7—C11—C12121.1 (5)C29—C28—N5120.0 (5)
N1—C12—C4121.9 (5)C30—C29—C28120.0 (5)
N1—C12—C11117.7 (5)C30—C29—H29A120.0
C4—C12—C11120.3 (5)C28—C29—H29A120.0
N3—C13—C14111.0 (4)C31—C30—C29120.9 (6)
N3—C13—H13A109.4C31—C30—H30A119.6
C14—C13—H13A109.4C29—C30—H30A119.6
N3—C13—H13B109.4C30—C31—C32119.7 (6)
C14—C13—H13B109.4C30—C31—H31A120.2
H13A—C13—H13B108.0C32—C31—H31A120.2
C13—C14—H14A109.5C31—C32—C33120.2 (5)
C13—C14—H14B109.5C31—C32—H32A119.9
H14A—C14—H14B109.5C33—C32—H32A119.9
C13—C14—H14C109.5C28—C33—C32120.6 (5)
H14A—C14—H14C109.5C28—C33—H33A119.7
H14B—C14—H14C109.5C32—C33—H33A119.7
C12—N1—C1—C21.1 (7)C6—N4—C15—C16176.0 (4)
N1—C1—C2—C31.0 (7)C5—N3—C15—N40.1 (5)
C1—C2—C3—C40.2 (7)C13—N3—C15—N4163.9 (4)
C2—C3—C4—C121.2 (6)C5—N3—C15—C16175.7 (4)
C2—C3—C4—C5179.8 (4)C13—N3—C15—C1620.3 (7)
C15—N3—C5—C60.4 (5)N4—C15—C16—C2150.9 (7)
C13—N3—C5—C6163.3 (4)N3—C15—C16—C21133.8 (5)
C15—N3—C5—C4175.9 (4)N4—C15—C16—C17126.9 (5)
C13—N3—C5—C420.3 (7)N3—C15—C16—C1748.4 (6)
C3—C4—C5—C6176.6 (4)C21—C16—C17—C182.2 (7)
C12—C4—C5—C62.0 (6)C15—C16—C17—C18179.9 (4)
C3—C4—C5—N30.8 (8)C16—C17—C18—C191.3 (7)
C12—C4—C5—N3177.8 (4)C17—C18—C19—C203.4 (7)
C15—N4—C6—C50.6 (5)C17—C18—C19—N5174.2 (4)
C15—N4—C6—C7177.0 (4)C28—N5—C19—C18144.8 (5)
N3—C5—C6—N40.6 (5)C22—N5—C19—C1832.7 (7)
C4—C5—C6—N4176.1 (4)C28—N5—C19—C2037.6 (7)
N3—C5—C6—C7177.3 (4)C22—N5—C19—C20144.9 (5)
C4—C5—C6—C70.5 (7)C18—C19—C20—C212.0 (7)
N4—C6—C7—C11177.9 (4)N5—C19—C20—C21175.6 (4)
C5—C6—C7—C111.8 (6)C17—C16—C21—C203.7 (7)
N4—C6—C7—C82.1 (7)C15—C16—C21—C20178.4 (4)
C5—C6—C7—C8178.2 (4)C19—C20—C21—C161.6 (7)
C11—C7—C8—C91.7 (7)C28—N5—C22—C2751.5 (7)
C6—C7—C8—C9178.2 (4)C19—N5—C22—C27126.1 (5)
C7—C8—C9—C100.7 (7)C28—N5—C22—C23129.9 (5)
C11—N2—C10—C90.2 (8)C19—N5—C22—C2352.5 (7)
C8—C9—C10—N20.1 (9)C27—C22—C23—C241.6 (8)
C10—N2—C11—C71.4 (7)N5—C22—C23—C24177.1 (5)
C10—N2—C11—C12178.2 (4)C22—C23—C24—C250.5 (9)
C8—C7—C11—N22.2 (7)C23—C24—C25—C263.0 (10)
C6—C7—C11—N2177.8 (4)C24—C25—C26—C273.4 (11)
C8—C7—C11—C12177.5 (4)C23—C22—C27—C261.2 (8)
C6—C7—C11—C122.6 (6)N5—C22—C27—C26177.4 (5)
C1—N1—C12—C40.0 (7)C25—C26—C27—C221.2 (9)
C1—N1—C12—C11178.7 (4)C22—N5—C28—C33142.1 (5)
C3—C4—C12—N11.1 (6)C19—N5—C28—C3335.4 (7)
C5—C4—C12—N1179.8 (4)C22—N5—C28—C2934.8 (7)
C3—C4—C12—C11177.5 (4)C19—N5—C28—C29147.7 (5)
C5—C4—C12—C111.2 (6)C33—C28—C29—C300.3 (8)
N2—C11—C12—N12.0 (6)N5—C28—C29—C30177.2 (5)
C7—C11—C12—N1177.6 (4)C28—C29—C30—C310.8 (9)
N2—C11—C12—C4179.3 (4)C29—C30—C31—C321.2 (9)
C7—C11—C12—C41.1 (6)C30—C31—C32—C330.6 (9)
C15—N3—C13—C14100.1 (5)C29—C28—C33—C321.0 (8)
C5—N3—C13—C1460.7 (5)N5—C28—C33—C32177.9 (5)
C6—N4—C15—N30.3 (5)C31—C32—C33—C280.5 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C24—H24A···N4i0.932.513.430 (4)171
Symmetry code: (i) x, y+3/2, z1/2.
 

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