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In the title compound, C22H15BrN2, the phenanthrene moiety is slightly skewed. The dihedral angle between the phenanthro­[9,10-d]­imidazole mean plane and the benzene ring is 37.78 (6)°. The crystal packing is stabilized mainly by aromatic interactions, though a weak intermolecular C—H...N hydrogen bond is also observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007002/cv6465sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007002/cv6465Isup2.hkl
Contains datablock I

CCDC reference: 270286

Key indicators

  • Single-crystal X-ray study
  • T = 122 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.024
  • wR factor = 0.057
  • Data-to-parameter ratio = 22.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) ....... ?
Alert level G ABSTY01_ALERT_1_G Extra text has been found in the _exptl_absorpt_correction_type field, which should be only a single keyword. A literature citation should be included in the _exptl_absorpt_process_details field. 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 31.00 From the CIF: _reflns_number_total 5137 Count of symmetry unique reflns 2723 Completeness (_total/calc) 188.65% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2414 Fraction of Friedel pairs measured 0.887 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

2-(4-bromophenyl)-1-methyl-1H-phenanthro[9,10 - d]imidazole top
Crystal data top
C22H15BrN2F(000) = 784
Mr = 387.27Dx = 1.589 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 26555 reflections
a = 6.0163 (4) Åθ = 2.3–31.0°
b = 29.332 (3) ŵ = 2.55 mm1
c = 9.1726 (8) ÅT = 122 K
V = 1618.7 (2) Å3Plate, pale yellow
Z = 40.55 × 0.46 × 0.08 mm
Data collection top
Nonius KappaCCD
diffractometer
5137 independent reflections
Radiation source: fine-focus sealed tube4771 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ω and φ scansθmax = 31.0°, θmin = 2.3°
Absorption correction: gaussian integration
(Coppens, 1970)
h = 88
Tmin = 0.365, Tmax = 0.903k = 4242
36851 measured reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.057 w = 1/[σ2(Fo2) + (0.0299P)2 + 0.9474P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.001
5137 reflectionsΔρmax = 0.45 e Å3
226 parametersΔρmin = 0.34 e Å3
1 restraintAbsolute structure: Flack (1983), 2414 Friedel reflections
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.009 (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
xyzUiso*/Ueq
Br0.65262 (2)0.079703 (4)0.66608 (2)0.02019 (4)
C10.2810 (3)0.12851 (5)0.63824 (16)0.0147 (3)
C20.4766 (2)0.15389 (5)0.6796 (2)0.0160 (3)
C30.5778 (3)0.15164 (6)0.8179 (2)0.0205 (3)
H30.51600.13250.89110.025*
C40.7664 (3)0.17701 (7)0.8485 (2)0.0232 (3)
H40.83220.17530.94250.028*
C50.8605 (3)0.20499 (7)0.7421 (2)0.0233 (4)
H50.98900.22250.76380.028*
C60.7662 (3)0.20704 (6)0.6052 (2)0.0205 (3)
H60.83270.22590.53320.025*
C70.5733 (3)0.18192 (5)0.56891 (19)0.0161 (3)
C80.4785 (3)0.18403 (5)0.42141 (18)0.0155 (3)
C90.5761 (3)0.20979 (5)0.30803 (19)0.0196 (3)
H90.70850.22650.32680.023*
C100.4831 (3)0.21123 (5)0.1706 (3)0.0205 (3)
H100.55330.22840.09580.025*
C110.2855 (3)0.18750 (5)0.14049 (17)0.0191 (3)
H110.22080.18900.04610.023*
C120.1862 (3)0.16206 (5)0.24821 (18)0.0172 (3)
H120.05220.14610.22820.021*
C130.2816 (3)0.15951 (5)0.38757 (18)0.0145 (3)
C140.1904 (3)0.13112 (5)0.49977 (17)0.0144 (3)
N150.0150 (2)0.10129 (5)0.48414 (15)0.0153 (2)
C160.0005 (3)0.08081 (5)0.61194 (19)0.0155 (3)
N170.1543 (2)0.09612 (5)0.71083 (15)0.0160 (3)
C180.1628 (3)0.08460 (6)0.86542 (19)0.0225 (3)
H18A0.17910.11260.92300.034*
H18B0.28970.06450.88370.034*
H18C0.02510.06900.89340.034*
C190.1581 (3)0.04300 (5)0.63613 (15)0.0148 (3)
C200.3628 (3)0.04461 (5)0.56351 (18)0.0160 (3)
H200.40020.07070.50710.019*
C210.5119 (3)0.00851 (5)0.57303 (18)0.0163 (3)
H210.65140.00980.52470.020*
C220.4530 (2)0.02955 (5)0.6546 (2)0.0153 (3)
C230.2506 (3)0.03255 (5)0.72577 (18)0.0165 (3)
H230.21260.05910.77980.020*
C240.1033 (3)0.00418 (6)0.71667 (19)0.0173 (3)
H240.03560.00270.76580.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.01858 (7)0.01718 (6)0.02480 (7)0.00343 (5)0.00294 (9)0.00021 (8)
C10.0141 (6)0.0144 (6)0.0157 (9)0.0021 (5)0.0018 (5)0.0014 (5)
C20.0138 (6)0.0164 (5)0.0179 (8)0.0026 (4)0.0026 (7)0.0019 (7)
C30.0185 (8)0.0236 (7)0.0193 (8)0.0008 (6)0.0016 (6)0.0007 (6)
C40.0178 (8)0.0305 (8)0.0212 (8)0.0012 (7)0.0045 (7)0.0034 (7)
C50.0166 (9)0.0263 (8)0.0271 (9)0.0021 (7)0.0042 (7)0.0051 (7)
C60.0165 (8)0.0200 (8)0.0250 (8)0.0020 (6)0.0015 (7)0.0013 (7)
C70.0144 (7)0.0151 (6)0.0188 (7)0.0009 (5)0.0005 (6)0.0019 (6)
C80.0158 (7)0.0129 (6)0.0178 (7)0.0012 (5)0.0012 (6)0.0021 (5)
C90.0201 (8)0.0169 (7)0.0217 (8)0.0035 (6)0.0025 (6)0.0011 (6)
C100.0261 (7)0.0177 (6)0.0177 (6)0.0024 (5)0.0046 (9)0.0011 (8)
C110.0260 (7)0.0157 (6)0.0157 (9)0.0021 (6)0.0003 (6)0.0008 (5)
C120.0196 (8)0.0141 (6)0.0180 (7)0.0003 (5)0.0011 (6)0.0007 (6)
C130.0151 (7)0.0121 (6)0.0162 (7)0.0017 (5)0.0009 (6)0.0021 (5)
C140.0145 (7)0.0139 (6)0.0147 (7)0.0019 (5)0.0007 (5)0.0017 (5)
N150.0148 (6)0.0148 (6)0.0164 (6)0.0000 (5)0.0006 (5)0.0000 (5)
C160.0146 (7)0.0143 (6)0.0176 (6)0.0012 (5)0.0008 (6)0.0003 (5)
N170.0161 (6)0.0166 (6)0.0153 (6)0.0003 (5)0.0005 (5)0.0003 (5)
C180.0281 (9)0.0246 (8)0.0146 (7)0.0039 (7)0.0019 (7)0.0013 (6)
C190.0146 (6)0.0151 (6)0.0147 (8)0.0000 (5)0.0027 (5)0.0005 (5)
C200.0163 (7)0.0151 (6)0.0167 (7)0.0021 (5)0.0013 (6)0.0017 (6)
C210.0146 (7)0.0192 (7)0.0152 (7)0.0018 (6)0.0006 (6)0.0014 (6)
C220.0157 (6)0.0155 (5)0.0147 (7)0.0012 (5)0.0023 (7)0.0021 (7)
C230.0184 (7)0.0151 (6)0.0160 (7)0.0029 (6)0.0005 (6)0.0024 (6)
C240.0163 (7)0.0186 (7)0.0169 (6)0.0019 (6)0.0004 (6)0.0013 (6)
Geometric parameters (Å, º) top
Br—C221.9020 (14)C11—H110.9500
C1—C141.384 (2)C12—C131.403 (2)
C1—N171.388 (2)C12—H120.9500
C1—C21.443 (2)C13—C141.433 (2)
C2—C31.409 (3)C14—N151.378 (2)
C2—C71.430 (2)N15—C161.320 (2)
C3—C41.386 (3)C16—N171.376 (2)
C3—H30.9500C16—C191.476 (2)
C4—C51.395 (3)N17—C181.459 (2)
C4—H40.9500C18—H18A0.9800
C5—C61.379 (3)C18—H18B0.9800
C5—H50.9500C18—H18C0.9800
C6—C71.414 (2)C19—C241.397 (2)
C6—H60.9500C19—C201.401 (2)
C7—C81.470 (2)C20—C211.391 (2)
C8—C91.413 (2)C20—H200.9500
C8—C131.420 (2)C21—C221.390 (2)
C9—C101.380 (3)C21—H210.9500
C9—H90.9500C22—C231.384 (2)
C10—C111.405 (2)C23—C241.398 (2)
C10—H100.9500C23—H230.9500
C11—C121.375 (2)C24—H240.9500
C14—C1—N17105.17 (13)C12—C13—C14121.92 (15)
C14—C1—C2122.25 (15)C8—C13—C14117.17 (14)
N17—C1—C2132.43 (15)N15—C14—C1111.21 (14)
C3—C2—C7119.37 (14)N15—C14—C13125.97 (14)
C3—C2—C1124.38 (16)C1—C14—C13122.70 (15)
C7—C2—C1116.22 (16)C16—N15—C14104.51 (13)
C4—C3—C2120.70 (17)N15—C16—N17112.90 (14)
C4—C3—H3119.6N15—C16—C19121.37 (15)
C2—C3—H3119.6N17—C16—C19125.54 (14)
C3—C4—C5120.45 (17)C16—N17—C1106.19 (13)
C3—C4—H4119.8C16—N17—C18126.09 (14)
C5—C4—H4119.8C1—N17—C18127.28 (14)
C6—C5—C4119.72 (17)N17—C18—H18A109.5
C6—C5—H5120.1N17—C18—H18B109.5
C4—C5—H5120.1H18A—C18—H18B109.5
C5—C6—C7121.95 (17)N17—C18—H18C109.5
C5—C6—H6119.0H18A—C18—H18C109.5
C7—C6—H6119.0H18B—C18—H18C109.5
C6—C7—C2117.79 (16)C24—C19—C20119.10 (14)
C6—C7—C8120.88 (15)C24—C19—C16122.71 (14)
C2—C7—C8121.32 (15)C20—C19—C16117.91 (14)
C9—C8—C13117.17 (15)C21—C20—C19120.77 (15)
C9—C8—C7122.59 (15)C21—C20—H20119.6
C13—C8—C7120.24 (14)C19—C20—H20119.6
C10—C9—C8121.34 (16)C22—C21—C20118.74 (15)
C10—C9—H9119.3C22—C21—H21120.6
C8—C9—H9119.3C20—C21—H21120.6
C9—C10—C11120.49 (17)C23—C22—C21121.96 (14)
C9—C10—H10119.8C23—C22—Br118.70 (12)
C11—C10—H10119.8C21—C22—Br119.33 (12)
C12—C11—C10119.70 (16)C22—C23—C24118.73 (15)
C12—C11—H11120.1C22—C23—H23120.6
C10—C11—H11120.1C24—C23—H23120.6
C11—C12—C13120.39 (16)C19—C24—C23120.69 (15)
C11—C12—H12119.8C19—C24—H24119.7
C13—C12—H12119.8C23—C24—H24119.7
C12—C13—C8120.88 (15)
C14—C1—C2—C3178.57 (15)N17—C1—C14—C13176.96 (14)
N17—C1—C2—C33.6 (3)C2—C1—C14—C130.8 (2)
C14—C1—C2—C70.3 (2)C12—C13—C14—N154.9 (2)
N17—C1—C2—C7174.70 (15)C8—C13—C14—N15172.98 (14)
C7—C2—C3—C41.4 (2)C12—C13—C14—C1179.37 (15)
C1—C2—C3—C4179.63 (16)C8—C13—C14—C12.7 (2)
C2—C3—C4—C50.5 (3)C1—C14—N15—C160.01 (17)
C3—C4—C5—C60.6 (3)C13—C14—N15—C16176.15 (15)
C4—C5—C6—C70.8 (3)C14—N15—C16—N170.69 (17)
C5—C6—C7—C20.1 (3)C14—N15—C16—C19174.58 (14)
C5—C6—C7—C8178.83 (16)N15—C16—N17—C11.12 (18)
C3—C2—C7—C61.2 (2)C19—C16—N17—C1173.92 (14)
C1—C2—C7—C6179.55 (14)N15—C16—N17—C18171.76 (15)
C3—C2—C7—C8177.71 (15)C19—C16—N17—C1813.2 (3)
C1—C2—C7—C80.6 (2)C14—C1—N17—C161.03 (16)
C6—C7—C8—C91.8 (2)C2—C1—N17—C16174.61 (16)
C2—C7—C8—C9177.07 (15)C14—C1—N17—C18171.74 (15)
C6—C7—C8—C13178.42 (15)C2—C1—N17—C1812.6 (3)
C2—C7—C8—C132.7 (2)N15—C16—C19—C24139.03 (16)
C13—C8—C9—C100.4 (2)N17—C16—C19—C2435.6 (2)
C7—C8—C9—C10179.86 (15)N15—C16—C19—C2034.9 (2)
C8—C9—C10—C111.0 (2)N17—C16—C19—C20150.48 (15)
C9—C10—C11—C121.1 (2)C24—C19—C20—C211.1 (2)
C10—C11—C12—C130.3 (2)C16—C19—C20—C21175.22 (15)
C11—C12—C13—C81.7 (2)C19—C20—C21—C220.8 (2)
C11—C12—C13—C14176.06 (15)C20—C21—C22—C230.2 (3)
C9—C8—C13—C121.7 (2)C20—C21—C22—Br178.91 (13)
C7—C8—C13—C12178.48 (15)C21—C22—C23—C241.0 (3)
C9—C8—C13—C14176.16 (14)Br—C22—C23—C24179.63 (12)
C7—C8—C13—C143.6 (2)C20—C19—C24—C230.4 (2)
N17—C1—C14—N150.67 (17)C16—C19—C24—C23174.20 (15)
C2—C1—C14—N15175.53 (13)C22—C23—C24—C190.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23···N15i0.952.543.419 (2)154
Symmetry code: (i) x, y, z+1/2.
 

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