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In the title compound, C21H19NO2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028790/rz2067sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028790/rz2067Isup2.hkl
Contains datablock I

CCDC reference: 618316

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Computing details top

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)-9H-carbazole top
Crystal data top
C21H19NO2F(000) = 672
Mr = 317.37Dx = 1.306 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9179 reflections
a = 9.2766 (1) Åθ = 2.6–34.9°
b = 25.0761 (3) ŵ = 0.08 mm1
c = 7.0947 (1) ÅT = 100 K
β = 101.935 (1)°Block, colourless
V = 1614.70 (4) Å30.34 × 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 tube3880 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 8.33 pixels mm-1θmax = 30.6°, θmin = 1.6°
ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 3535
Tmin = 0.938, Tmax = 0.986l = 1010
51344 measured reflections
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-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 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.24 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
O10.37608 (9)0.02222 (3)0.31654 (13)0.0232 (2)
O20.20698 (9)0.03998 (4)0.18087 (13)0.0236 (2)
N10.05011 (11)0.14428 (4)0.31018 (14)0.0189 (2)
C10.19339 (13)0.15983 (4)0.31217 (17)0.0194 (2)
C20.32316 (14)0.15176 (5)0.17521 (18)0.0237 (3)
H20.32260.13300.05900.028*
C30.45306 (14)0.17202 (5)0.21467 (19)0.0266 (3)
H30.54260.16680.12370.032*
C40.45556 (15)0.19999 (5)0.3857 (2)0.0266 (3)
H40.54600.21370.40800.032*
C50.32668 (14)0.20771 (5)0.52207 (19)0.0242 (3)
H50.32820.22650.63800.029*
C60.19443 (13)0.18743 (4)0.48622 (17)0.0200 (2)
C70.04427 (14)0.18836 (4)0.59344 (16)0.0193 (2)
C80.02477 (15)0.21044 (5)0.77008 (17)0.0233 (3)
H80.03140.22840.84840.028*
C90.17616 (15)0.20578 (5)0.82938 (17)0.0251 (3)
H90.22390.22080.94900.030*
C100.25985 (14)0.17917 (5)0.71462 (18)0.0238 (3)
H100.36360.17650.75800.029*
C110.19379 (13)0.15659 (5)0.53850 (17)0.0208 (2)
H110.25060.13850.46130.025*
C120.04126 (13)0.16145 (4)0.47943 (16)0.0181 (2)
C130.00128 (13)0.11550 (5)0.15713 (16)0.0191 (2)
H13A0.07760.11590.03940.023*
H13B0.08760.13440.12750.023*
C140.04372 (13)0.05831 (5)0.20854 (15)0.0176 (2)
C150.18913 (13)0.04193 (4)0.24080 (15)0.0182 (2)
H150.26370.06710.23050.022*
C160.22831 (13)0.01097 (5)0.28835 (16)0.0186 (2)
C170.11954 (14)0.04754 (5)0.30566 (16)0.0200 (2)
H170.14540.08330.34140.024*
C180.02770 (13)0.03175 (5)0.27066 (16)0.0206 (2)
H180.10210.05700.28090.025*
C190.06593 (13)0.02055 (5)0.22108 (16)0.0185 (2)
C200.41994 (15)0.07468 (5)0.3816 (2)0.0271 (3)
H20A0.52760.07740.40570.041*
H20B0.38600.08210.50090.041*
H20C0.37640.10060.28280.041*
C210.32260 (14)0.00362 (6)0.19335 (19)0.0268 (3)
H21A0.41720.02240.16480.040*
H21B0.32360.02530.10010.040*
H21C0.30650.01130.32370.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0192 (4)0.0210 (4)0.0294 (5)0.0015 (3)0.0049 (3)0.0039 (3)
O20.0163 (4)0.0271 (5)0.0274 (4)0.0014 (3)0.0046 (3)0.0016 (3)
N10.0179 (5)0.0196 (5)0.0190 (4)0.0019 (4)0.0036 (4)0.0012 (3)
C10.0188 (6)0.0174 (5)0.0221 (5)0.0015 (4)0.0048 (4)0.0030 (4)
C20.0229 (6)0.0242 (6)0.0234 (6)0.0019 (5)0.0032 (5)0.0028 (4)
C30.0188 (6)0.0267 (6)0.0332 (7)0.0014 (5)0.0027 (5)0.0076 (5)
C40.0219 (6)0.0222 (6)0.0378 (7)0.0044 (5)0.0114 (5)0.0068 (5)
C50.0262 (6)0.0179 (6)0.0313 (6)0.0024 (5)0.0127 (5)0.0025 (4)
C60.0219 (6)0.0148 (5)0.0244 (5)0.0005 (4)0.0075 (4)0.0026 (4)
C70.0220 (6)0.0153 (5)0.0213 (5)0.0005 (4)0.0064 (4)0.0012 (4)
C80.0325 (7)0.0169 (5)0.0220 (5)0.0005 (5)0.0090 (5)0.0017 (4)
C90.0322 (7)0.0210 (6)0.0209 (5)0.0033 (5)0.0025 (5)0.0018 (4)
C100.0217 (6)0.0221 (6)0.0257 (6)0.0020 (5)0.0006 (4)0.0012 (4)
C110.0207 (6)0.0183 (5)0.0233 (6)0.0003 (4)0.0048 (4)0.0002 (4)
C120.0208 (6)0.0151 (5)0.0183 (5)0.0003 (4)0.0043 (4)0.0013 (4)
C130.0206 (6)0.0198 (5)0.0177 (5)0.0015 (4)0.0059 (4)0.0005 (4)
C140.0200 (6)0.0197 (5)0.0133 (5)0.0001 (4)0.0039 (4)0.0014 (4)
C150.0191 (6)0.0191 (5)0.0171 (5)0.0030 (4)0.0054 (4)0.0008 (4)
C160.0191 (6)0.0213 (5)0.0154 (5)0.0006 (4)0.0035 (4)0.0009 (4)
C170.0245 (6)0.0185 (5)0.0168 (5)0.0014 (4)0.0040 (4)0.0000 (4)
C180.0213 (6)0.0226 (6)0.0185 (5)0.0057 (4)0.0054 (4)0.0017 (4)
C190.0169 (5)0.0231 (6)0.0160 (5)0.0009 (4)0.0046 (4)0.0026 (4)
C200.0260 (7)0.0222 (6)0.0331 (7)0.0046 (5)0.0058 (5)0.0040 (5)
C210.0204 (6)0.0352 (7)0.0256 (6)0.0071 (5)0.0069 (5)0.0049 (5)
Geometric parameters (Å, º) top
O1—C161.3731 (14)C9—H90.95
O1—C201.4252 (15)C10—C111.3931 (17)
O2—C191.3698 (14)C10—H100.95
O2—C211.4244 (15)C11—C121.3955 (17)
N1—C121.3873 (14)C11—H110.95
N1—C11.3880 (15)C13—C141.5117 (16)
N1—C131.4634 (14)C13—H13A0.99
C1—C21.3966 (17)C13—H13B0.99
C1—C61.4174 (16)C14—C151.3831 (16)
C2—C31.3885 (18)C14—C191.4059 (16)
C2—H20.95C15—C161.3982 (16)
C3—C41.4058 (19)C15—H150.95
C3—H30.95C16—C171.3877 (17)
C4—C51.3873 (19)C17—C181.3942 (17)
C4—H40.95C17—H170.95
C5—C61.3991 (17)C18—C191.3849 (17)
C5—H50.95C18—H180.95
C6—C71.4427 (17)C20—H20A0.98
C7—C81.3983 (16)C20—H20B0.98
C7—C121.4158 (16)C20—H20C0.98
C8—C91.3850 (19)C21—H21A0.98
C8—H80.95C21—H21B0.98
C9—C101.4045 (18)C21—H21C0.98
C16—O1—C20116.51 (9)N1—C12—C7109.16 (10)
C19—O2—C21117.29 (10)C11—C12—C7121.55 (10)
C12—N1—C1108.60 (9)N1—C13—C14113.42 (9)
C12—N1—C13124.11 (10)N1—C13—H13A108.9
C1—N1—C13127.28 (10)C14—C13—H13A108.9
N1—C1—C2129.92 (11)N1—C13—H13B108.9
N1—C1—C6108.97 (10)C14—C13—H13B108.9
C2—C1—C6121.11 (11)H13A—C13—H13B107.7
C3—C2—C1117.76 (12)C15—C14—C19118.89 (11)
C3—C2—H2121.1C15—C14—C13121.20 (10)
C1—C2—H2121.1C19—C14—C13119.90 (10)
C2—C3—C4121.77 (12)C14—C15—C16121.17 (11)
C2—C3—H3119.1C14—C15—H15119.4
C4—C3—H3119.1C16—C15—H15119.4
C5—C4—C3120.39 (12)O1—C16—C17125.00 (11)
C5—C4—H4119.8O1—C16—C15115.60 (10)
C3—C4—H4119.8C17—C16—C15119.40 (11)
C4—C5—C6118.96 (12)C16—C17—C18120.00 (11)
C4—C5—H5120.5C16—C17—H17120.0
C6—C5—H5120.5C18—C17—H17120.0
C5—C6—C1120.01 (11)C19—C18—C17120.28 (11)
C5—C6—C7133.28 (11)C19—C18—H18119.9
C1—C6—C7106.71 (10)C17—C18—H18119.9
C8—C7—C12119.59 (11)O2—C19—C18124.97 (11)
C8—C7—C6133.82 (11)O2—C19—C14114.81 (10)
C12—C7—C6106.56 (10)C18—C19—C14120.22 (11)
C9—C8—C7119.12 (11)O1—C20—H20A109.5
C9—C8—H8120.4O1—C20—H20B109.5
C7—C8—H8120.4H20A—C20—H20B109.5
C8—C9—C10120.75 (11)O1—C20—H20C109.5
C8—C9—H9119.6H20A—C20—H20C109.5
C10—C9—H9119.6H20B—C20—H20C109.5
C11—C10—C9121.31 (12)O2—C21—H21A109.5
C11—C10—H10119.3O2—C21—H21B109.5
C9—C10—H10119.3H21A—C21—H21B109.5
C10—C11—C12117.68 (11)O2—C21—H21C109.5
C10—C11—H11121.2H21A—C21—H21C109.5
C12—C11—H11121.2H21B—C21—H21C109.5
N1—C12—C11129.26 (11)
C12—N1—C1—C2179.87 (12)C10—C11—C12—N1177.85 (11)
C13—N1—C1—C21.2 (2)C10—C11—C12—C70.06 (17)
C12—N1—C1—C60.13 (13)C8—C7—C12—N1178.56 (10)
C13—N1—C1—C6179.09 (10)C6—C7—C12—N10.28 (12)
N1—C1—C2—C3179.84 (11)C8—C7—C12—C110.38 (17)
C6—C1—C2—C30.45 (18)C6—C7—C12—C11177.90 (10)
C1—C2—C3—C40.27 (18)C12—N1—C13—C1473.22 (14)
C2—C3—C4—C50.64 (19)C1—N1—C13—C14107.97 (13)
C3—C4—C5—C60.28 (18)N1—C13—C14—C15110.43 (12)
C4—C5—C6—C10.43 (17)N1—C13—C14—C1970.63 (13)
C4—C5—C6—C7179.73 (12)C19—C14—C15—C161.05 (16)
N1—C1—C6—C5179.43 (10)C13—C14—C15—C16180.00 (10)
C2—C1—C6—C50.81 (17)C20—O1—C16—C174.62 (16)
N1—C1—C6—C70.04 (13)C20—O1—C16—C15174.67 (10)
C2—C1—C6—C7179.73 (10)C14—C15—C16—O1179.91 (9)
C5—C6—C7—C81.2 (2)C14—C15—C16—C170.75 (16)
C1—C6—C7—C8178.12 (12)O1—C16—C17—C18179.01 (10)
C5—C6—C7—C12179.17 (12)C15—C16—C17—C181.72 (17)
C1—C6—C7—C120.19 (12)C16—C17—C18—C190.87 (17)
C12—C7—C8—C90.43 (17)C21—O2—C19—C180.77 (16)
C6—C7—C8—C9177.28 (12)C21—O2—C19—C14179.34 (10)
C7—C8—C9—C100.18 (18)C17—C18—C19—O2178.92 (10)
C8—C9—C10—C110.13 (19)C17—C18—C19—C140.97 (17)
C9—C10—C11—C120.19 (17)C15—C14—C19—O2177.99 (9)
C1—N1—C12—C11177.74 (11)C13—C14—C19—O20.97 (15)
C13—N1—C12—C111.26 (18)C15—C14—C19—C181.91 (16)
C1—N1—C12—C70.26 (12)C13—C14—C19—C18179.12 (10)
C13—N1—C12—C7179.26 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···Cg2i0.952.783.6510 (14)152
C8—H8···Cg1i0.952.743.5000 (14)137
C17—H17···Cg1ii0.952.773.5808 (13)144
C20—H20B···Cg2ii0.982.783.4752 (14)129
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y, z+1.
 

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