In the title compound, C
21H
19NO
2, the carbazole ring system is planar to within 0.032 (1) Å, and forms a dihedral angle of 74.42 (3)° with the plane of the attached benzene ring. Inversion-related molecules are linked by C—H
π hydrogen bonds into cyclic centrosymmetric dimers, which are interlinked into a chain along the
c axis by π–π stacking interactions. Adjacent glide-related chains are interlinked
via C—H
π interactions into a sheet parallel to the
bc plane.
Supporting information
CCDC reference: 618316
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C)= 0.002 Å
- R factor = 0.046
- wR factor = 0.137
- Data-to-parameter ratio = 22.5
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
9-(2,5-Dimethoxybenzyl)-9
H-carbazole
top
Crystal data top
C21H19NO2 | F(000) = 672 |
Mr = 317.37 | Dx = 1.306 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9179 reflections |
a = 9.2766 (1) Å | θ = 2.6–34.9° |
b = 25.0761 (3) Å | µ = 0.08 mm−1 |
c = 7.0947 (1) Å | T = 100 K |
β = 101.935 (1)° | Block, colourless |
V = 1614.70 (4) Å3 | 0.34 × 0.23 × 0.17 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX2 CCD area-detector diffractometer | 4935 independent reflections |
Radiation source: fine-focus sealed tube | 3880 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.6°, θmin = 1.6° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −35→35 |
Tmin = 0.938, Tmax = 0.986 | l = −10→10 |
51344 measured reflections | |
Refinement top
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0743P)2 + 0.2926P] where P = (Fo2 + 2Fc2)/3 |
4935 reflections | (Δ/σ)max = 0.001 |
219 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
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 | |
O1 | 0.37608 (9) | 0.02222 (3) | 0.31654 (13) | 0.0232 (2) | |
O2 | −0.20698 (9) | −0.03998 (4) | 0.18087 (13) | 0.0236 (2) | |
N1 | −0.05011 (11) | −0.14428 (4) | 0.31018 (14) | 0.0189 (2) | |
C1 | −0.19339 (13) | −0.15983 (4) | 0.31217 (17) | 0.0194 (2) | |
C2 | −0.32316 (14) | −0.15176 (5) | 0.17521 (18) | 0.0237 (3) | |
H2 | −0.3226 | −0.1330 | 0.0590 | 0.028* | |
C3 | −0.45306 (14) | −0.17202 (5) | 0.21467 (19) | 0.0266 (3) | |
H3 | −0.5426 | −0.1668 | 0.1237 | 0.032* | |
C4 | −0.45556 (15) | −0.19999 (5) | 0.3857 (2) | 0.0266 (3) | |
H4 | −0.5460 | −0.2137 | 0.4080 | 0.032* | |
C5 | −0.32668 (14) | −0.20771 (5) | 0.52207 (19) | 0.0242 (3) | |
H5 | −0.3282 | −0.2265 | 0.6380 | 0.029* | |
C6 | −0.19443 (13) | −0.18743 (4) | 0.48622 (17) | 0.0200 (2) | |
C7 | −0.04427 (14) | −0.18836 (4) | 0.59344 (16) | 0.0193 (2) | |
C8 | 0.02477 (15) | −0.21044 (5) | 0.77008 (17) | 0.0233 (3) | |
H8 | −0.0314 | −0.2284 | 0.8484 | 0.028* | |
C9 | 0.17616 (15) | −0.20578 (5) | 0.82938 (17) | 0.0251 (3) | |
H9 | 0.2239 | −0.2208 | 0.9490 | 0.030* | |
C10 | 0.25985 (14) | −0.17917 (5) | 0.71462 (18) | 0.0238 (3) | |
H10 | 0.3636 | −0.1765 | 0.7580 | 0.029* | |
C11 | 0.19379 (13) | −0.15659 (5) | 0.53850 (17) | 0.0208 (2) | |
H11 | 0.2506 | −0.1385 | 0.4613 | 0.025* | |
C12 | 0.04126 (13) | −0.16145 (4) | 0.47943 (16) | 0.0181 (2) | |
C13 | 0.00128 (13) | −0.11550 (5) | 0.15713 (16) | 0.0191 (2) | |
H13A | −0.0776 | −0.1159 | 0.0394 | 0.023* | |
H13B | 0.0876 | −0.1344 | 0.1275 | 0.023* | |
C14 | 0.04372 (13) | −0.05831 (5) | 0.20854 (15) | 0.0176 (2) | |
C15 | 0.18913 (13) | −0.04193 (4) | 0.24080 (15) | 0.0182 (2) | |
H15 | 0.2637 | −0.0671 | 0.2305 | 0.022* | |
C16 | 0.22831 (13) | 0.01097 (5) | 0.28835 (16) | 0.0186 (2) | |
C17 | 0.11954 (14) | 0.04754 (5) | 0.30566 (16) | 0.0200 (2) | |
H17 | 0.1454 | 0.0833 | 0.3414 | 0.024* | |
C18 | −0.02770 (13) | 0.03175 (5) | 0.27066 (16) | 0.0206 (2) | |
H18 | −0.1021 | 0.0570 | 0.2809 | 0.025* | |
C19 | −0.06593 (13) | −0.02055 (5) | 0.22108 (16) | 0.0185 (2) | |
C20 | 0.41994 (15) | 0.07468 (5) | 0.3816 (2) | 0.0271 (3) | |
H20A | 0.5276 | 0.0774 | 0.4057 | 0.041* | |
H20B | 0.3860 | 0.0821 | 0.5009 | 0.041* | |
H20C | 0.3764 | 0.1006 | 0.2828 | 0.041* | |
C21 | −0.32260 (14) | −0.00362 (6) | 0.19335 (19) | 0.0268 (3) | |
H21A | −0.4172 | −0.0224 | 0.1648 | 0.040* | |
H21B | −0.3236 | 0.0253 | 0.1001 | 0.040* | |
H21C | −0.3065 | 0.0113 | 0.3237 | 0.040* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0192 (4) | 0.0210 (4) | 0.0294 (5) | −0.0015 (3) | 0.0049 (3) | −0.0039 (3) |
O2 | 0.0163 (4) | 0.0271 (5) | 0.0274 (4) | 0.0014 (3) | 0.0046 (3) | 0.0016 (3) |
N1 | 0.0179 (5) | 0.0196 (5) | 0.0190 (4) | −0.0019 (4) | 0.0036 (4) | 0.0012 (3) |
C1 | 0.0188 (6) | 0.0174 (5) | 0.0221 (5) | −0.0015 (4) | 0.0048 (4) | −0.0030 (4) |
C2 | 0.0229 (6) | 0.0242 (6) | 0.0234 (6) | −0.0019 (5) | 0.0032 (5) | −0.0028 (4) |
C3 | 0.0188 (6) | 0.0267 (6) | 0.0332 (7) | −0.0014 (5) | 0.0027 (5) | −0.0076 (5) |
C4 | 0.0219 (6) | 0.0222 (6) | 0.0378 (7) | −0.0044 (5) | 0.0114 (5) | −0.0068 (5) |
C5 | 0.0262 (6) | 0.0179 (6) | 0.0313 (6) | −0.0024 (5) | 0.0127 (5) | −0.0025 (4) |
C6 | 0.0219 (6) | 0.0148 (5) | 0.0244 (5) | −0.0005 (4) | 0.0075 (4) | −0.0026 (4) |
C7 | 0.0220 (6) | 0.0153 (5) | 0.0213 (5) | 0.0005 (4) | 0.0064 (4) | −0.0012 (4) |
C8 | 0.0325 (7) | 0.0169 (5) | 0.0220 (5) | 0.0005 (5) | 0.0090 (5) | 0.0017 (4) |
C9 | 0.0322 (7) | 0.0210 (6) | 0.0209 (5) | 0.0033 (5) | 0.0025 (5) | 0.0018 (4) |
C10 | 0.0217 (6) | 0.0221 (6) | 0.0257 (6) | 0.0020 (5) | 0.0006 (4) | −0.0012 (4) |
C11 | 0.0207 (6) | 0.0183 (5) | 0.0233 (6) | 0.0003 (4) | 0.0048 (4) | −0.0002 (4) |
C12 | 0.0208 (6) | 0.0151 (5) | 0.0183 (5) | −0.0003 (4) | 0.0043 (4) | −0.0013 (4) |
C13 | 0.0206 (6) | 0.0198 (5) | 0.0177 (5) | −0.0015 (4) | 0.0059 (4) | −0.0005 (4) |
C14 | 0.0200 (6) | 0.0197 (5) | 0.0133 (5) | −0.0001 (4) | 0.0039 (4) | 0.0014 (4) |
C15 | 0.0191 (6) | 0.0191 (5) | 0.0171 (5) | 0.0030 (4) | 0.0054 (4) | 0.0008 (4) |
C16 | 0.0191 (6) | 0.0213 (5) | 0.0154 (5) | −0.0006 (4) | 0.0035 (4) | 0.0009 (4) |
C17 | 0.0245 (6) | 0.0185 (5) | 0.0168 (5) | 0.0014 (4) | 0.0040 (4) | 0.0000 (4) |
C18 | 0.0213 (6) | 0.0226 (6) | 0.0185 (5) | 0.0057 (4) | 0.0054 (4) | 0.0017 (4) |
C19 | 0.0169 (5) | 0.0231 (6) | 0.0160 (5) | 0.0009 (4) | 0.0046 (4) | 0.0026 (4) |
C20 | 0.0260 (7) | 0.0222 (6) | 0.0331 (7) | −0.0046 (5) | 0.0058 (5) | −0.0040 (5) |
C21 | 0.0204 (6) | 0.0352 (7) | 0.0256 (6) | 0.0071 (5) | 0.0069 (5) | 0.0049 (5) |
Geometric parameters (Å, º) top
O1—C16 | 1.3731 (14) | C9—H9 | 0.95 |
O1—C20 | 1.4252 (15) | C10—C11 | 1.3931 (17) |
O2—C19 | 1.3698 (14) | C10—H10 | 0.95 |
O2—C21 | 1.4244 (15) | C11—C12 | 1.3955 (17) |
N1—C12 | 1.3873 (14) | C11—H11 | 0.95 |
N1—C1 | 1.3880 (15) | C13—C14 | 1.5117 (16) |
N1—C13 | 1.4634 (14) | C13—H13A | 0.99 |
C1—C2 | 1.3966 (17) | C13—H13B | 0.99 |
C1—C6 | 1.4174 (16) | C14—C15 | 1.3831 (16) |
C2—C3 | 1.3885 (18) | C14—C19 | 1.4059 (16) |
C2—H2 | 0.95 | C15—C16 | 1.3982 (16) |
C3—C4 | 1.4058 (19) | C15—H15 | 0.95 |
C3—H3 | 0.95 | C16—C17 | 1.3877 (17) |
C4—C5 | 1.3873 (19) | C17—C18 | 1.3942 (17) |
C4—H4 | 0.95 | C17—H17 | 0.95 |
C5—C6 | 1.3991 (17) | C18—C19 | 1.3849 (17) |
C5—H5 | 0.95 | C18—H18 | 0.95 |
C6—C7 | 1.4427 (17) | C20—H20A | 0.98 |
C7—C8 | 1.3983 (16) | C20—H20B | 0.98 |
C7—C12 | 1.4158 (16) | C20—H20C | 0.98 |
C8—C9 | 1.3850 (19) | C21—H21A | 0.98 |
C8—H8 | 0.95 | C21—H21B | 0.98 |
C9—C10 | 1.4045 (18) | C21—H21C | 0.98 |
| | | |
C16—O1—C20 | 116.51 (9) | N1—C12—C7 | 109.16 (10) |
C19—O2—C21 | 117.29 (10) | C11—C12—C7 | 121.55 (10) |
C12—N1—C1 | 108.60 (9) | N1—C13—C14 | 113.42 (9) |
C12—N1—C13 | 124.11 (10) | N1—C13—H13A | 108.9 |
C1—N1—C13 | 127.28 (10) | C14—C13—H13A | 108.9 |
N1—C1—C2 | 129.92 (11) | N1—C13—H13B | 108.9 |
N1—C1—C6 | 108.97 (10) | C14—C13—H13B | 108.9 |
C2—C1—C6 | 121.11 (11) | H13A—C13—H13B | 107.7 |
C3—C2—C1 | 117.76 (12) | C15—C14—C19 | 118.89 (11) |
C3—C2—H2 | 121.1 | C15—C14—C13 | 121.20 (10) |
C1—C2—H2 | 121.1 | C19—C14—C13 | 119.90 (10) |
C2—C3—C4 | 121.77 (12) | C14—C15—C16 | 121.17 (11) |
C2—C3—H3 | 119.1 | C14—C15—H15 | 119.4 |
C4—C3—H3 | 119.1 | C16—C15—H15 | 119.4 |
C5—C4—C3 | 120.39 (12) | O1—C16—C17 | 125.00 (11) |
C5—C4—H4 | 119.8 | O1—C16—C15 | 115.60 (10) |
C3—C4—H4 | 119.8 | C17—C16—C15 | 119.40 (11) |
C4—C5—C6 | 118.96 (12) | C16—C17—C18 | 120.00 (11) |
C4—C5—H5 | 120.5 | C16—C17—H17 | 120.0 |
C6—C5—H5 | 120.5 | C18—C17—H17 | 120.0 |
C5—C6—C1 | 120.01 (11) | C19—C18—C17 | 120.28 (11) |
C5—C6—C7 | 133.28 (11) | C19—C18—H18 | 119.9 |
C1—C6—C7 | 106.71 (10) | C17—C18—H18 | 119.9 |
C8—C7—C12 | 119.59 (11) | O2—C19—C18 | 124.97 (11) |
C8—C7—C6 | 133.82 (11) | O2—C19—C14 | 114.81 (10) |
C12—C7—C6 | 106.56 (10) | C18—C19—C14 | 120.22 (11) |
C9—C8—C7 | 119.12 (11) | O1—C20—H20A | 109.5 |
C9—C8—H8 | 120.4 | O1—C20—H20B | 109.5 |
C7—C8—H8 | 120.4 | H20A—C20—H20B | 109.5 |
C8—C9—C10 | 120.75 (11) | O1—C20—H20C | 109.5 |
C8—C9—H9 | 119.6 | H20A—C20—H20C | 109.5 |
C10—C9—H9 | 119.6 | H20B—C20—H20C | 109.5 |
C11—C10—C9 | 121.31 (12) | O2—C21—H21A | 109.5 |
C11—C10—H10 | 119.3 | O2—C21—H21B | 109.5 |
C9—C10—H10 | 119.3 | H21A—C21—H21B | 109.5 |
C10—C11—C12 | 117.68 (11) | O2—C21—H21C | 109.5 |
C10—C11—H11 | 121.2 | H21A—C21—H21C | 109.5 |
C12—C11—H11 | 121.2 | H21B—C21—H21C | 109.5 |
N1—C12—C11 | 129.26 (11) | | |
| | | |
C12—N1—C1—C2 | 179.87 (12) | C10—C11—C12—N1 | −177.85 (11) |
C13—N1—C1—C2 | −1.2 (2) | C10—C11—C12—C7 | −0.06 (17) |
C12—N1—C1—C6 | 0.13 (13) | C8—C7—C12—N1 | 178.56 (10) |
C13—N1—C1—C6 | 179.09 (10) | C6—C7—C12—N1 | 0.28 (12) |
N1—C1—C2—C3 | 179.84 (11) | C8—C7—C12—C11 | 0.38 (17) |
C6—C1—C2—C3 | −0.45 (18) | C6—C7—C12—C11 | −177.90 (10) |
C1—C2—C3—C4 | −0.27 (18) | C12—N1—C13—C14 | −73.22 (14) |
C2—C3—C4—C5 | 0.64 (19) | C1—N1—C13—C14 | 107.97 (13) |
C3—C4—C5—C6 | −0.28 (18) | N1—C13—C14—C15 | 110.43 (12) |
C4—C5—C6—C1 | −0.43 (17) | N1—C13—C14—C19 | −70.63 (13) |
C4—C5—C6—C7 | −179.73 (12) | C19—C14—C15—C16 | 1.05 (16) |
N1—C1—C6—C5 | −179.43 (10) | C13—C14—C15—C16 | 180.00 (10) |
C2—C1—C6—C5 | 0.81 (17) | C20—O1—C16—C17 | 4.62 (16) |
N1—C1—C6—C7 | 0.04 (13) | C20—O1—C16—C15 | −174.67 (10) |
C2—C1—C6—C7 | −179.73 (10) | C14—C15—C16—O1 | −179.91 (9) |
C5—C6—C7—C8 | 1.2 (2) | C14—C15—C16—C17 | 0.75 (16) |
C1—C6—C7—C8 | −178.12 (12) | O1—C16—C17—C18 | 179.01 (10) |
C5—C6—C7—C12 | 179.17 (12) | C15—C16—C17—C18 | −1.72 (17) |
C1—C6—C7—C12 | −0.19 (12) | C16—C17—C18—C19 | 0.87 (17) |
C12—C7—C8—C9 | −0.43 (17) | C21—O2—C19—C18 | −0.77 (16) |
C6—C7—C8—C9 | 177.28 (12) | C21—O2—C19—C14 | 179.34 (10) |
C7—C8—C9—C10 | 0.18 (18) | C17—C18—C19—O2 | −178.92 (10) |
C8—C9—C10—C11 | 0.13 (19) | C17—C18—C19—C14 | 0.97 (17) |
C9—C10—C11—C12 | −0.19 (17) | C15—C14—C19—O2 | 177.99 (9) |
C1—N1—C12—C11 | 177.74 (11) | C13—C14—C19—O2 | −0.97 (15) |
C13—N1—C12—C11 | −1.26 (18) | C15—C14—C19—C18 | −1.91 (16) |
C1—N1—C12—C7 | −0.26 (12) | C13—C14—C19—C18 | 179.12 (10) |
C13—N1—C12—C7 | −179.26 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cg2i | 0.95 | 2.78 | 3.6510 (14) | 152 |
C8—H8···Cg1i | 0.95 | 2.74 | 3.5000 (14) | 137 |
C17—H17···Cg1ii | 0.95 | 2.77 | 3.5808 (13) | 144 |
C20—H20B···Cg2ii | 0.98 | 2.78 | 3.4752 (14) | 129 |
Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) −x, −y, −z+1. |