The title compound, C
18H
12Br
2N
2, was synthesized by
N-alkylation of 4-chloromethylpyridine with 3,6-dibromo-9
H-carbazole. The carbazole ring system is essentially planar, with a mean deviation of 0.012 Å, and makes a dihedral angle of 83.2 (8)° with the plane of the pyridine ring. In the crystal structure, weak C—H
Br interactions are observed.
Supporting information
CCDC reference: 601782
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.038
- wR factor = 0.114
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
Tmin and Tmax reported: 0.240 0.353
Tmin and Tmax expected: 0.211 0.353
RR = 1.141
Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.12
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.52 Ratio
PLAT432_ALERT_2_C Short Inter X...Y Contact Br1 .. C10 .. 3.31 Ang.
0 ALERT level A = In general: serious problem
0 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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
3,6-Dibromo-9-(4-pyridylmethyl)-9
H-carbazole
top
Crystal data top
C18H12Br2N2 | F(000) = 816 |
Mr = 416.12 | Dx = 1.774 Mg m−3 |
Monoclinic, P21/n | Melting point = 510–511 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 11.266 (4) Å | Cell parameters from 3336 reflections |
b = 9.729 (4) Å | θ = 2.5–26.3° |
c = 14.367 (5) Å | µ = 5.20 mm−1 |
β = 98.341 (6)° | T = 294 K |
V = 1558.1 (10) Å3 | Rod, colourless |
Z = 4 | 0.32 × 0.26 × 0.20 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3207 independent reflections |
Radiation source: fine-focus sealed tube | 2376 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
φ and ω scans | θmax = 26.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −14→9 |
Tmin = 0.240, Tmax = 0.353 | k = −12→10 |
8543 measured reflections | l = −17→18 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0619P)2 + 0.1399P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
3207 reflections | Δρmax = 0.70 e Å−3 |
200 parameters | Δρmin = −0.80 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0067 (7) |
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 | x | y | z | Uiso*/Ueq | |
Br1 | −0.09928 (4) | 0.11077 (4) | 0.40415 (3) | 0.04612 (18) | |
Br2 | 0.58071 (4) | 0.47024 (5) | 0.63655 (4) | 0.0611 (2) | |
N1 | 0.0678 (3) | 0.5376 (3) | 0.6946 (2) | 0.0310 (7) | |
N2 | −0.1581 (4) | 0.3652 (4) | 0.9477 (3) | 0.0686 (13) | |
C1 | 0.0134 (3) | 0.4414 (3) | 0.6319 (2) | 0.0286 (7) | |
C2 | −0.1064 (3) | 0.4060 (4) | 0.6104 (3) | 0.0360 (8) | |
H2 | −0.1642 | 0.4479 | 0.6409 | 0.043* | |
C3 | −0.1382 (3) | 0.3075 (4) | 0.5429 (3) | 0.0378 (9) | |
H3 | −0.2182 | 0.2824 | 0.5271 | 0.045* | |
C4 | −0.0510 (3) | 0.2453 (4) | 0.4982 (2) | 0.0340 (8) | |
C5 | 0.0687 (3) | 0.2777 (4) | 0.5187 (2) | 0.0318 (8) | |
H5 | 0.1259 | 0.2339 | 0.4886 | 0.038* | |
C6 | 0.1010 (3) | 0.3786 (3) | 0.5862 (2) | 0.0270 (7) | |
C7 | 0.2142 (3) | 0.4396 (3) | 0.6236 (2) | 0.0270 (7) | |
C8 | 0.3310 (3) | 0.4200 (4) | 0.6064 (3) | 0.0321 (8) | |
H8 | 0.3490 | 0.3553 | 0.5629 | 0.039* | |
C9 | 0.4193 (3) | 0.4993 (4) | 0.6560 (3) | 0.0374 (9) | |
C10 | 0.3958 (4) | 0.5975 (4) | 0.7212 (3) | 0.0387 (9) | |
H10 | 0.4584 | 0.6494 | 0.7528 | 0.046* | |
C11 | 0.2802 (3) | 0.6185 (4) | 0.7392 (2) | 0.0332 (8) | |
H11 | 0.2634 | 0.6840 | 0.7826 | 0.040* | |
C12 | 0.1899 (3) | 0.5385 (3) | 0.6906 (2) | 0.0274 (7) | |
C13 | 0.0045 (4) | 0.6191 (4) | 0.7562 (3) | 0.0406 (9) | |
H13A | −0.0578 | 0.6720 | 0.7184 | 0.049* | |
H13B | 0.0600 | 0.6833 | 0.7910 | 0.049* | |
C14 | −0.0513 (4) | 0.5321 (4) | 0.8243 (3) | 0.0362 (9) | |
C15 | −0.1673 (4) | 0.5552 (5) | 0.8409 (3) | 0.0483 (11) | |
H15 | −0.2125 | 0.6267 | 0.8109 | 0.058* | |
C16 | −0.2155 (5) | 0.4697 (5) | 0.9035 (4) | 0.0677 (15) | |
H16 | −0.2932 | 0.4874 | 0.9148 | 0.081* | |
C17 | −0.0465 (5) | 0.3453 (5) | 0.9326 (3) | 0.0623 (13) | |
H17 | −0.0032 | 0.2747 | 0.9653 | 0.075* | |
C18 | 0.0099 (4) | 0.4224 (4) | 0.8714 (3) | 0.0481 (10) | |
H18 | 0.0877 | 0.4014 | 0.8617 | 0.058* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0493 (3) | 0.0409 (3) | 0.0446 (3) | −0.00835 (19) | −0.0055 (2) | −0.00776 (17) |
Br2 | 0.0206 (2) | 0.0740 (4) | 0.0891 (4) | 0.0008 (2) | 0.0093 (2) | 0.0005 (3) |
N1 | 0.0244 (15) | 0.0328 (16) | 0.0374 (16) | −0.0016 (13) | 0.0103 (14) | −0.0070 (13) |
N2 | 0.081 (3) | 0.056 (3) | 0.079 (3) | −0.005 (2) | 0.047 (3) | 0.005 (2) |
C1 | 0.0239 (18) | 0.0284 (16) | 0.0343 (18) | −0.0003 (15) | 0.0071 (15) | 0.0000 (15) |
C2 | 0.0212 (18) | 0.043 (2) | 0.045 (2) | −0.0017 (16) | 0.0103 (17) | −0.0036 (17) |
C3 | 0.0226 (18) | 0.040 (2) | 0.049 (2) | −0.0079 (16) | 0.0012 (17) | −0.0001 (17) |
C4 | 0.033 (2) | 0.0313 (18) | 0.0354 (18) | −0.0054 (17) | −0.0009 (16) | −0.0014 (16) |
C5 | 0.0264 (18) | 0.0345 (18) | 0.0346 (17) | 0.0010 (15) | 0.0048 (16) | −0.0025 (15) |
C6 | 0.0229 (18) | 0.0285 (17) | 0.0294 (17) | 0.0011 (14) | 0.0035 (15) | 0.0025 (14) |
C7 | 0.0224 (17) | 0.0293 (16) | 0.0297 (17) | 0.0008 (14) | 0.0045 (15) | 0.0039 (14) |
C8 | 0.0248 (18) | 0.0327 (18) | 0.0382 (19) | 0.0023 (15) | 0.0025 (16) | 0.0017 (15) |
C9 | 0.0201 (18) | 0.041 (2) | 0.050 (2) | 0.0008 (16) | 0.0007 (17) | 0.0106 (18) |
C10 | 0.030 (2) | 0.039 (2) | 0.044 (2) | −0.0085 (17) | −0.0044 (17) | 0.0037 (17) |
C11 | 0.031 (2) | 0.0321 (19) | 0.0364 (19) | −0.0002 (16) | 0.0045 (17) | −0.0005 (15) |
C12 | 0.0254 (18) | 0.0301 (18) | 0.0273 (16) | −0.0020 (15) | 0.0058 (15) | 0.0036 (14) |
C13 | 0.039 (2) | 0.0339 (19) | 0.053 (2) | −0.0010 (17) | 0.022 (2) | −0.0064 (17) |
C14 | 0.037 (2) | 0.0334 (19) | 0.040 (2) | −0.0018 (17) | 0.0118 (18) | −0.0072 (16) |
C15 | 0.041 (2) | 0.047 (2) | 0.061 (3) | 0.000 (2) | 0.023 (2) | −0.002 (2) |
C16 | 0.052 (3) | 0.070 (3) | 0.092 (4) | −0.008 (3) | 0.045 (3) | −0.007 (3) |
C17 | 0.081 (4) | 0.053 (3) | 0.058 (3) | 0.003 (3) | 0.027 (3) | 0.006 (2) |
C18 | 0.047 (3) | 0.048 (2) | 0.053 (2) | 0.006 (2) | 0.019 (2) | −0.001 (2) |
Geometric parameters (Å, º) top
Br1—C4 | 1.904 (3) | C8—C9 | 1.373 (5) |
Br2—C9 | 1.901 (4) | C8—H8 | 0.9300 |
N1—C1 | 1.380 (4) | C9—C10 | 1.390 (6) |
N1—C12 | 1.385 (4) | C10—C11 | 1.380 (5) |
N1—C13 | 1.450 (5) | C10—H10 | 0.9300 |
N2—C16 | 1.317 (7) | C11—C12 | 1.386 (5) |
N2—C17 | 1.320 (7) | C11—H11 | 0.9300 |
C1—C2 | 1.384 (5) | C13—C14 | 1.499 (5) |
C1—C6 | 1.402 (5) | C13—H13A | 0.9700 |
C2—C3 | 1.373 (5) | C13—H13B | 0.9700 |
C2—H2 | 0.9300 | C14—C15 | 1.381 (6) |
C3—C4 | 1.387 (5) | C14—C18 | 1.391 (6) |
C3—H3 | 0.9300 | C15—C16 | 1.392 (6) |
C4—C5 | 1.375 (5) | C15—H15 | 0.9300 |
C5—C6 | 1.391 (5) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | C17—C18 | 1.379 (6) |
C6—C7 | 1.438 (5) | C17—H17 | 0.9300 |
C7—C8 | 1.387 (5) | C18—H18 | 0.9300 |
C7—C12 | 1.415 (5) | | |
| | | |
C1—N1—C12 | 109.0 (3) | C11—C10—C9 | 120.3 (4) |
C1—N1—C13 | 123.9 (3) | C11—C10—H10 | 119.8 |
C12—N1—C13 | 127.0 (3) | C9—C10—H10 | 119.8 |
C16—N2—C17 | 116.5 (4) | C10—C11—C12 | 117.8 (3) |
N1—C1—C2 | 129.9 (3) | C10—C11—H11 | 121.1 |
N1—C1—C6 | 109.0 (3) | C12—C11—H11 | 121.1 |
C2—C1—C6 | 121.1 (3) | N1—C12—C11 | 130.0 (3) |
C3—C2—C1 | 118.5 (3) | N1—C12—C7 | 108.4 (3) |
C3—C2—H2 | 120.8 | C11—C12—C7 | 121.6 (3) |
C1—C2—H2 | 120.8 | N1—C13—C14 | 112.3 (3) |
C2—C3—C4 | 120.1 (3) | N1—C13—H13A | 109.1 |
C2—C3—H3 | 119.9 | C14—C13—H13A | 109.1 |
C4—C3—H3 | 119.9 | N1—C13—H13B | 109.1 |
C5—C4—C3 | 122.7 (3) | C14—C13—H13B | 109.1 |
C5—C4—Br1 | 118.7 (3) | H13A—C13—H13B | 107.9 |
C3—C4—Br1 | 118.7 (3) | C15—C14—C18 | 117.1 (4) |
C4—C5—C6 | 117.4 (3) | C15—C14—C13 | 121.2 (4) |
C4—C5—H5 | 121.3 | C18—C14—C13 | 121.7 (4) |
C6—C5—H5 | 121.3 | C14—C15—C16 | 118.8 (5) |
C5—C6—C1 | 120.3 (3) | C14—C15—H15 | 120.6 |
C5—C6—C7 | 132.8 (3) | C16—C15—H15 | 120.6 |
C1—C6—C7 | 106.9 (3) | N2—C16—C15 | 124.3 (5) |
C8—C7—C12 | 119.8 (3) | N2—C16—H16 | 117.9 |
C8—C7—C6 | 133.6 (3) | C15—C16—H16 | 117.9 |
C12—C7—C6 | 106.6 (3) | N2—C17—C18 | 124.3 (5) |
C9—C8—C7 | 117.7 (4) | N2—C17—H17 | 117.9 |
C9—C8—H8 | 121.2 | C18—C17—H17 | 117.9 |
C7—C8—H8 | 121.2 | C17—C18—C14 | 119.0 (4) |
C8—C9—C10 | 122.8 (4) | C17—C18—H18 | 120.5 |
C8—C9—Br2 | 118.4 (3) | C14—C18—H18 | 120.5 |
C10—C9—Br2 | 118.7 (3) | | |
| | | |
C12—N1—C1—C2 | −178.8 (4) | C8—C9—C10—C11 | 0.5 (6) |
C13—N1—C1—C2 | 3.3 (6) | Br2—C9—C10—C11 | −178.0 (3) |
C12—N1—C1—C6 | 0.0 (4) | C9—C10—C11—C12 | 0.2 (5) |
C13—N1—C1—C6 | −177.9 (3) | C1—N1—C12—C11 | 179.0 (3) |
N1—C1—C2—C3 | 178.6 (4) | C13—N1—C12—C11 | −3.1 (6) |
C6—C1—C2—C3 | −0.1 (6) | C1—N1—C12—C7 | −0.2 (4) |
C1—C2—C3—C4 | 0.3 (6) | C13—N1—C12—C7 | 177.6 (3) |
C2—C3—C4—C5 | 0.2 (6) | C10—C11—C12—N1 | −180.0 (3) |
C2—C3—C4—Br1 | −179.3 (3) | C10—C11—C12—C7 | −0.8 (5) |
C3—C4—C5—C6 | −0.9 (5) | C8—C7—C12—N1 | −179.8 (3) |
Br1—C4—C5—C6 | 178.6 (2) | C6—C7—C12—N1 | 0.3 (4) |
C4—C5—C6—C1 | 1.2 (5) | C8—C7—C12—C11 | 0.9 (5) |
C4—C5—C6—C7 | −178.6 (4) | C6—C7—C12—C11 | −179.0 (3) |
N1—C1—C6—C5 | −179.6 (3) | C1—N1—C13—C14 | 62.3 (5) |
C2—C1—C6—C5 | −0.7 (5) | C12—N1—C13—C14 | −115.2 (4) |
N1—C1—C6—C7 | 0.2 (4) | N1—C13—C14—C15 | −135.0 (4) |
C2—C1—C6—C7 | 179.1 (3) | N1—C13—C14—C18 | 43.1 (5) |
C5—C6—C7—C8 | −0.4 (7) | C18—C14—C15—C16 | 0.6 (6) |
C1—C6—C7—C8 | 179.8 (4) | C13—C14—C15—C16 | 178.8 (4) |
C5—C6—C7—C12 | 179.5 (3) | C17—N2—C16—C15 | 2.1 (8) |
C1—C6—C7—C12 | −0.4 (4) | C14—C15—C16—N2 | −1.1 (8) |
C12—C7—C8—C9 | −0.3 (5) | C16—N2—C17—C18 | −2.9 (8) |
C6—C7—C8—C9 | 179.5 (4) | N2—C17—C18—C14 | 2.5 (8) |
C7—C8—C9—C10 | −0.4 (6) | C15—C14—C18—C17 | −1.2 (6) |
C7—C8—C9—Br2 | 178.1 (3) | C13—C14—C18—C17 | −179.4 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···Br2i | 0.93 | 2.87 | 3.653 (4) | 142 |
Symmetry code: (i) x−1, y, z. |