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organic compounds
2-Dibutylamino-1-(2,7-dichloro-9H-fluoren-4-yl)ethanol
aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bSeQuent Scientific Ltd, No. 120 A & B, Industrial Area, Baikampady, New Mangalore, Karnataka, 575 011, India, and cOrganic Chemistry Division, Department of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
*Correspondence e-mail: hkfun@usm.my
In the title compound, C23H29Cl2NO, the fluorene ring is essentially planar, with a maximum deviation from the mean plane of 0.041 (1) Å. The amine group adopts a pyramidal configuration, the sum of the bond angles being 336.2 (3)°. In the crystal, the molecules are linked into dimers by intermolecular O—H⋯N and C—H⋯O hydrogen bonds. Weak C—H⋯π and π–π [centroid–centroid distance = 3.7544 (7) Å] interactions are also observed.
Related literature
For general background and applications of fluorene derivatives, see: Reinhardt et al. (1998); Yao & Belfield (2005
); Werts et al. (2004
); Belfield et al. (2009
); Sun et al. (2009
); Park et al. (2009
); Kotaka et al. (2010
); Wong et al. (2005
); Beulter et al. (2007
). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009
); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008
); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009
).
Supporting information
10.1107/S1600536810037566/fj2335sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810037566/fj2335Isup2.hkl
The title compound was recrystallized from acetone. M.p. 352–354 K. The sample was a gift from SeQuent Scientific Ltd., No: 120 A & B, Industrial Area, Baikampady, New Mangalore, Karnataka, 575 011, India.
The O-bound hydrogen atom was located from difference Fourier map and refined freely. The rest of the hydrogen atoms were positioned geometrically and refined using a riding model. A rotating-group model was applied for the methyl groups.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C23H29Cl2NO | Z = 2 |
Mr = 406.37 | F(000) = 432 |
Triclinic, P1 | Dx = 1.283 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0009 (4) Å | Cell parameters from 9903 reflections |
b = 10.8847 (4) Å | θ = 2.8–35.1° |
c = 11.0853 (4) Å | µ = 0.32 mm−1 |
α = 68.161 (1)° | T = 100 K |
β = 70.999 (1)° | Block, colourless |
γ = 88.904 (1)° | 0.34 × 0.28 × 0.20 mm |
V = 1051.90 (7) Å3 |
Bruker APEXII DUO CCD area-detector diffractometer | 6052 independent reflections |
Radiation source: fine-focus sealed tube | 5448 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ϕ and ω scans | θmax = 30.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −14→14 |
Tmin = 0.900, Tmax = 0.937 | k = −13→15 |
19180 measured reflections | l = −15→15 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0878P)2 + 0.1785P] where P = (Fo2 + 2Fc2)/3 |
6052 reflections | (Δ/σ)max = 0.001 |
250 parameters | Δρmax = 0.65 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C23H29Cl2NO | γ = 88.904 (1)° |
Mr = 406.37 | V = 1051.90 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.0009 (4) Å | Mo Kα radiation |
b = 10.8847 (4) Å | µ = 0.32 mm−1 |
c = 11.0853 (4) Å | T = 100 K |
α = 68.161 (1)° | 0.34 × 0.28 × 0.20 mm |
β = 70.999 (1)° |
Bruker APEXII DUO CCD area-detector diffractometer | 6052 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 5448 reflections with I > 2σ(I) |
Tmin = 0.900, Tmax = 0.937 | Rint = 0.025 |
19180 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.15 | Δρmax = 0.65 e Å−3 |
6052 reflections | Δρmin = −0.39 e Å−3 |
250 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.09361 (3) | 0.21897 (3) | 0.88976 (3) | 0.02143 (10) | |
Cl2 | 0.91082 (3) | 0.72785 (3) | 0.47680 (3) | 0.02310 (10) | |
O1 | 0.34512 (9) | −0.00277 (8) | 0.98844 (9) | 0.01700 (17) | |
N1 | 0.61607 (10) | 0.00676 (9) | 0.76424 (10) | 0.01474 (18) | |
C1 | 0.37158 (11) | 0.35655 (11) | 0.76122 (11) | 0.01307 (19) | |
C2 | 0.51590 (11) | 0.42961 (11) | 0.70234 (11) | 0.0137 (2) | |
C3 | 0.64840 (12) | 0.38878 (11) | 0.70641 (12) | 0.0157 (2) | |
H3A | 0.6557 | 0.3002 | 0.7557 | 0.019* | |
C4 | 0.76946 (12) | 0.48193 (12) | 0.63599 (12) | 0.0174 (2) | |
H4A | 0.8580 | 0.4555 | 0.6380 | 0.021* | |
C5 | 0.75782 (12) | 0.61409 (12) | 0.56297 (12) | 0.0170 (2) | |
C6 | 0.62725 (12) | 0.65831 (11) | 0.55809 (11) | 0.0168 (2) | |
H6A | 0.6208 | 0.7472 | 0.5093 | 0.020* | |
C7 | 0.50725 (12) | 0.56512 (11) | 0.62855 (11) | 0.0147 (2) | |
C8 | 0.35494 (12) | 0.58751 (11) | 0.64065 (12) | 0.0166 (2) | |
H8A | 0.3211 | 0.6472 | 0.6879 | 0.020* | |
H8B | 0.3446 | 0.6239 | 0.5503 | 0.020* | |
C9 | 0.27675 (11) | 0.44936 (11) | 0.72460 (11) | 0.0143 (2) | |
C10 | 0.13297 (12) | 0.41040 (12) | 0.76341 (11) | 0.0161 (2) | |
H10A | 0.0709 | 0.4719 | 0.7390 | 0.019* | |
C11 | 0.08464 (11) | 0.27561 (12) | 0.84032 (12) | 0.0160 (2) | |
C12 | 0.17583 (11) | 0.18198 (11) | 0.87841 (11) | 0.0154 (2) | |
H12A | 0.1399 | 0.0928 | 0.9301 | 0.019* | |
C13 | 0.32054 (11) | 0.22131 (11) | 0.83943 (11) | 0.01356 (19) | |
C14 | 0.41897 (11) | 0.11665 (11) | 0.87700 (11) | 0.0141 (2) | |
H14A | 0.4898 | 0.1530 | 0.9023 | 0.017* | |
C15 | 0.49599 (12) | 0.08479 (11) | 0.74948 (12) | 0.0154 (2) | |
H15A | 0.4284 | 0.0352 | 0.7336 | 0.018* | |
H15B | 0.5313 | 0.1676 | 0.6691 | 0.018* | |
C16 | 0.74550 (12) | 0.06358 (12) | 0.63995 (12) | 0.0162 (2) | |
H16A | 0.8249 | 0.0192 | 0.6611 | 0.019* | |
H16B | 0.7652 | 0.1569 | 0.6218 | 0.019* | |
C17 | 0.74054 (12) | 0.05380 (12) | 0.50737 (12) | 0.0188 (2) | |
H17A | 0.7301 | −0.0393 | 0.5209 | 0.023* | |
H17B | 0.6582 | 0.0929 | 0.4878 | 0.023* | |
C18 | 0.87478 (13) | 0.12510 (13) | 0.38423 (12) | 0.0220 (2) | |
H18A | 0.8838 | 0.2184 | 0.3702 | 0.026* | |
H18B | 0.9570 | 0.0873 | 0.4053 | 0.026* | |
C19 | 0.87480 (18) | 0.11485 (18) | 0.25151 (15) | 0.0351 (3) | |
H19A | 0.9637 | 0.1568 | 0.1791 | 0.053* | |
H19B | 0.7982 | 0.1585 | 0.2259 | 0.053* | |
H19C | 0.8625 | 0.0227 | 0.2655 | 0.053* | |
C20 | 0.57620 (12) | −0.13645 (11) | 0.80309 (12) | 0.0167 (2) | |
H20A | 0.5521 | −0.1476 | 0.7295 | 0.020* | |
H20B | 0.4922 | −0.1680 | 0.8859 | 0.020* | |
C21 | 0.69500 (13) | −0.22106 (12) | 0.82942 (12) | 0.0184 (2) | |
H21A | 0.7679 | −0.2082 | 0.7415 | 0.022* | |
H21B | 0.7381 | −0.1912 | 0.8820 | 0.022* | |
C22 | 0.64153 (15) | −0.36850 (13) | 0.90795 (13) | 0.0229 (2) | |
H22A | 0.5982 | −0.3982 | 0.8554 | 0.027* | |
H22B | 0.5687 | −0.3813 | 0.9959 | 0.027* | |
C23 | 0.7601 (2) | −0.45345 (16) | 0.93422 (16) | 0.0342 (3) | |
H23A | 0.7230 | −0.5460 | 0.9768 | 0.051* | |
H23B | 0.7965 | −0.4309 | 0.9944 | 0.051* | |
H23C | 0.8353 | −0.4369 | 0.8480 | 0.051* | |
H1O1 | 0.359 (2) | 0.001 (2) | 1.062 (2) | 0.036 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.01152 (14) | 0.02463 (17) | 0.02342 (16) | 0.00024 (10) | −0.00496 (11) | −0.00501 (12) |
Cl2 | 0.01794 (15) | 0.02340 (17) | 0.02422 (16) | −0.00603 (11) | −0.00230 (11) | −0.00900 (12) |
O1 | 0.0163 (4) | 0.0142 (4) | 0.0161 (4) | −0.0002 (3) | −0.0040 (3) | −0.0025 (3) |
N1 | 0.0124 (4) | 0.0129 (4) | 0.0171 (4) | 0.0023 (3) | −0.0027 (3) | −0.0058 (3) |
C1 | 0.0123 (4) | 0.0138 (5) | 0.0132 (4) | 0.0025 (3) | −0.0043 (4) | −0.0055 (4) |
C2 | 0.0134 (5) | 0.0145 (5) | 0.0139 (4) | 0.0019 (4) | −0.0047 (4) | −0.0063 (4) |
C3 | 0.0145 (5) | 0.0156 (5) | 0.0176 (5) | 0.0020 (4) | −0.0061 (4) | −0.0065 (4) |
C4 | 0.0135 (5) | 0.0205 (5) | 0.0195 (5) | 0.0011 (4) | −0.0053 (4) | −0.0095 (4) |
C5 | 0.0152 (5) | 0.0194 (5) | 0.0157 (5) | −0.0027 (4) | −0.0029 (4) | −0.0078 (4) |
C6 | 0.0184 (5) | 0.0150 (5) | 0.0161 (5) | 0.0000 (4) | −0.0056 (4) | −0.0052 (4) |
C7 | 0.0156 (5) | 0.0146 (5) | 0.0141 (5) | 0.0020 (4) | −0.0048 (4) | −0.0060 (4) |
C8 | 0.0158 (5) | 0.0141 (5) | 0.0184 (5) | 0.0031 (4) | −0.0061 (4) | −0.0045 (4) |
C9 | 0.0139 (5) | 0.0147 (5) | 0.0145 (5) | 0.0034 (4) | −0.0048 (4) | −0.0060 (4) |
C10 | 0.0136 (5) | 0.0177 (5) | 0.0167 (5) | 0.0050 (4) | −0.0057 (4) | −0.0061 (4) |
C11 | 0.0115 (4) | 0.0183 (5) | 0.0166 (5) | 0.0012 (4) | −0.0036 (4) | −0.0061 (4) |
C12 | 0.0126 (5) | 0.0153 (5) | 0.0162 (5) | 0.0016 (4) | −0.0038 (4) | −0.0048 (4) |
C13 | 0.0125 (4) | 0.0140 (5) | 0.0135 (4) | 0.0029 (4) | −0.0038 (4) | −0.0053 (4) |
C14 | 0.0126 (4) | 0.0118 (5) | 0.0150 (5) | 0.0014 (3) | −0.0033 (4) | −0.0034 (4) |
C15 | 0.0138 (5) | 0.0147 (5) | 0.0173 (5) | 0.0033 (4) | −0.0050 (4) | −0.0061 (4) |
C16 | 0.0126 (5) | 0.0163 (5) | 0.0174 (5) | 0.0007 (4) | −0.0021 (4) | −0.0066 (4) |
C17 | 0.0180 (5) | 0.0181 (5) | 0.0176 (5) | 0.0001 (4) | −0.0025 (4) | −0.0070 (4) |
C18 | 0.0179 (5) | 0.0252 (6) | 0.0183 (5) | 0.0014 (4) | −0.0027 (4) | −0.0064 (4) |
C19 | 0.0343 (8) | 0.0468 (9) | 0.0195 (6) | −0.0015 (6) | −0.0029 (5) | −0.0130 (6) |
C20 | 0.0168 (5) | 0.0130 (5) | 0.0183 (5) | 0.0016 (4) | −0.0042 (4) | −0.0057 (4) |
C21 | 0.0204 (5) | 0.0158 (5) | 0.0180 (5) | 0.0054 (4) | −0.0047 (4) | −0.0073 (4) |
C22 | 0.0339 (7) | 0.0158 (5) | 0.0187 (5) | 0.0064 (5) | −0.0087 (5) | −0.0069 (4) |
C23 | 0.0539 (9) | 0.0255 (7) | 0.0317 (7) | 0.0212 (6) | −0.0222 (7) | −0.0146 (6) |
Cl1—C11 | 1.7358 (11) | C13—C14 | 1.5202 (15) |
Cl2—C5 | 1.7400 (12) | C14—C15 | 1.5354 (15) |
O1—C14 | 1.4175 (13) | C14—H14A | 0.9800 |
O1—H1O1 | 0.89 (2) | C15—H15A | 0.9700 |
N1—C15 | 1.4751 (14) | C15—H15B | 0.9700 |
N1—C20 | 1.4788 (14) | C16—C17 | 1.5290 (16) |
N1—C16 | 1.4805 (14) | C16—H16A | 0.9700 |
C1—C13 | 1.4037 (15) | C16—H16B | 0.9700 |
C1—C9 | 1.4119 (14) | C17—C18 | 1.5252 (16) |
C1—C2 | 1.4785 (15) | C17—H17A | 0.9700 |
C2—C3 | 1.3989 (15) | C17—H17B | 0.9700 |
C2—C7 | 1.4127 (15) | C18—C19 | 1.5162 (19) |
C3—C4 | 1.3950 (16) | C18—H18A | 0.9700 |
C3—H3A | 0.9300 | C18—H18B | 0.9700 |
C4—C5 | 1.3881 (17) | C19—H19A | 0.9600 |
C4—H4A | 0.9300 | C19—H19B | 0.9600 |
C5—C6 | 1.3936 (16) | C19—H19C | 0.9600 |
C6—C7 | 1.3878 (15) | C20—C21 | 1.5261 (16) |
C6—H6A | 0.9300 | C20—H20A | 0.9700 |
C7—C8 | 1.5082 (15) | C20—H20B | 0.9700 |
C8—C9 | 1.5062 (16) | C21—C22 | 1.5197 (17) |
C8—H8A | 0.9700 | C21—H21A | 0.9700 |
C8—H8B | 0.9700 | C21—H21B | 0.9700 |
C9—C10 | 1.3847 (15) | C22—C23 | 1.5259 (19) |
C10—C11 | 1.3932 (16) | C22—H22A | 0.9700 |
C10—H10A | 0.9300 | C22—H22B | 0.9700 |
C11—C12 | 1.3941 (15) | C23—H23A | 0.9600 |
C12—C13 | 1.3940 (15) | C23—H23B | 0.9600 |
C12—H12A | 0.9300 | C23—H23C | 0.9600 |
C14—O1—H1O1 | 105.1 (14) | N1—C15—H15A | 109.0 |
C15—N1—C20 | 111.58 (9) | C14—C15—H15A | 109.0 |
C15—N1—C16 | 111.49 (9) | N1—C15—H15B | 109.0 |
C20—N1—C16 | 113.09 (9) | C14—C15—H15B | 109.0 |
C13—C1—C9 | 119.98 (10) | H15A—C15—H15B | 107.8 |
C13—C1—C2 | 132.12 (10) | N1—C16—C17 | 116.53 (9) |
C9—C1—C2 | 107.90 (9) | N1—C16—H16A | 108.2 |
C3—C2—C7 | 119.17 (10) | C17—C16—H16A | 108.2 |
C3—C2—C1 | 132.54 (10) | N1—C16—H16B | 108.2 |
C7—C2—C1 | 108.28 (9) | C17—C16—H16B | 108.2 |
C4—C3—C2 | 119.50 (11) | H16A—C16—H16B | 107.3 |
C4—C3—H3A | 120.2 | C18—C17—C16 | 111.72 (10) |
C2—C3—H3A | 120.2 | C18—C17—H17A | 109.3 |
C5—C4—C3 | 119.99 (10) | C16—C17—H17A | 109.3 |
C5—C4—H4A | 120.0 | C18—C17—H17B | 109.3 |
C3—C4—H4A | 120.0 | C16—C17—H17B | 109.3 |
C4—C5—C6 | 121.95 (10) | H17A—C17—H17B | 107.9 |
C4—C5—Cl2 | 118.82 (9) | C19—C18—C17 | 113.12 (11) |
C6—C5—Cl2 | 119.23 (9) | C19—C18—H18A | 109.0 |
C7—C6—C5 | 117.74 (10) | C17—C18—H18A | 109.0 |
C7—C6—H6A | 121.1 | C19—C18—H18B | 109.0 |
C5—C6—H6A | 121.1 | C17—C18—H18B | 109.0 |
C6—C7—C2 | 121.64 (10) | H18A—C18—H18B | 107.8 |
C6—C7—C8 | 128.05 (10) | C18—C19—H19A | 109.5 |
C2—C7—C8 | 110.31 (10) | C18—C19—H19B | 109.5 |
C9—C8—C7 | 102.80 (9) | H19A—C19—H19B | 109.5 |
C9—C8—H8A | 111.2 | C18—C19—H19C | 109.5 |
C7—C8—H8A | 111.2 | H19A—C19—H19C | 109.5 |
C9—C8—H8B | 111.2 | H19B—C19—H19C | 109.5 |
C7—C8—H8B | 111.2 | N1—C20—C21 | 112.70 (9) |
H8A—C8—H8B | 109.1 | N1—C20—H20A | 109.1 |
C10—C9—C1 | 121.57 (10) | C21—C20—H20A | 109.1 |
C10—C9—C8 | 127.77 (10) | N1—C20—H20B | 109.1 |
C1—C9—C8 | 110.66 (9) | C21—C20—H20B | 109.1 |
C9—C10—C11 | 117.54 (10) | H20A—C20—H20B | 107.8 |
C9—C10—H10A | 121.2 | C22—C21—C20 | 112.38 (10) |
C11—C10—H10A | 121.2 | C22—C21—H21A | 109.1 |
C10—C11—C12 | 122.07 (10) | C20—C21—H21A | 109.1 |
C10—C11—Cl1 | 120.11 (9) | C22—C21—H21B | 109.1 |
C12—C11—Cl1 | 117.81 (9) | C20—C21—H21B | 109.1 |
C13—C12—C11 | 120.35 (10) | H21A—C21—H21B | 107.9 |
C13—C12—H12A | 119.8 | C21—C22—C23 | 112.52 (12) |
C11—C12—H12A | 119.8 | C21—C22—H22A | 109.1 |
C12—C13—C1 | 118.49 (10) | C23—C22—H22A | 109.1 |
C12—C13—C14 | 119.41 (10) | C21—C22—H22B | 109.1 |
C1—C13—C14 | 122.04 (9) | C23—C22—H22B | 109.1 |
O1—C14—C13 | 112.68 (9) | H22A—C22—H22B | 107.8 |
O1—C14—C15 | 108.89 (9) | C22—C23—H23A | 109.5 |
C13—C14—C15 | 108.43 (9) | C22—C23—H23B | 109.5 |
O1—C14—H14A | 108.9 | H23A—C23—H23B | 109.5 |
C13—C14—H14A | 108.9 | C22—C23—H23C | 109.5 |
C15—C14—H14A | 108.9 | H23A—C23—H23C | 109.5 |
N1—C15—C14 | 112.91 (9) | H23B—C23—H23C | 109.5 |
C13—C1—C2—C3 | −0.9 (2) | C9—C10—C11—C12 | 0.31 (17) |
C9—C1—C2—C3 | 179.75 (11) | C9—C10—C11—Cl1 | −178.74 (8) |
C13—C1—C2—C7 | 178.18 (11) | C10—C11—C12—C13 | −0.25 (18) |
C9—C1—C2—C7 | −1.15 (12) | Cl1—C11—C12—C13 | 178.83 (9) |
C7—C2—C3—C4 | −0.98 (16) | C11—C12—C13—C1 | −0.12 (17) |
C1—C2—C3—C4 | 178.04 (11) | C11—C12—C13—C14 | −177.47 (10) |
C2—C3—C4—C5 | 0.21 (17) | C9—C1—C13—C12 | 0.40 (16) |
C3—C4—C5—C6 | 0.51 (17) | C2—C1—C13—C12 | −178.86 (11) |
C3—C4—C5—Cl2 | 179.76 (9) | C9—C1—C13—C14 | 177.68 (10) |
C4—C5—C6—C7 | −0.40 (17) | C2—C1—C13—C14 | −1.58 (18) |
Cl2—C5—C6—C7 | −179.66 (8) | C12—C13—C14—O1 | −20.91 (14) |
C5—C6—C7—C2 | −0.40 (16) | C1—C13—C14—O1 | 161.83 (10) |
C5—C6—C7—C8 | 179.25 (10) | C12—C13—C14—C15 | 99.69 (11) |
C3—C2—C7—C6 | 1.10 (16) | C1—C13—C14—C15 | −77.56 (13) |
C1—C2—C7—C6 | −178.14 (10) | C20—N1—C15—C14 | 99.92 (11) |
C3—C2—C7—C8 | −178.62 (10) | C16—N1—C15—C14 | −132.56 (10) |
C1—C2—C7—C8 | 2.15 (12) | O1—C14—C15—N1 | −69.47 (11) |
C6—C7—C8—C9 | 178.09 (11) | C13—C14—C15—N1 | 167.61 (9) |
C2—C7—C8—C9 | −2.22 (12) | C15—N1—C16—C17 | −68.12 (12) |
C13—C1—C9—C10 | −0.34 (16) | C20—N1—C16—C17 | 58.58 (13) |
C2—C1—C9—C10 | 179.08 (10) | N1—C16—C17—C18 | 175.50 (10) |
C13—C1—C9—C8 | −179.72 (10) | C16—C17—C18—C19 | 178.77 (12) |
C2—C1—C9—C8 | −0.29 (12) | C15—N1—C20—C21 | −175.79 (9) |
C7—C8—C9—C10 | −177.83 (11) | C16—N1—C20—C21 | 57.56 (12) |
C7—C8—C9—C1 | 1.49 (12) | N1—C20—C21—C22 | 163.47 (10) |
C1—C9—C10—C11 | −0.01 (17) | C20—C21—C22—C23 | 179.89 (11) |
C8—C9—C10—C11 | 179.25 (11) |
Cg2 and Cg3 are the centroids of the C2–C7 and C1/C9–C13 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···N1i | 0.89 (2) | 1.99 (2) | 2.8762 (13) | 175 (2) |
C14—H14A···O1i | 0.98 | 2.57 | 3.1831 (15) | 121 |
C8—H8A···Cg2ii | 0.97 | 2.98 | 3.6293 (13) | 126 |
C22—H22A···Cg2iii | 0.97 | 2.82 | 3.6730 (15) | 148 |
C23—H23B···Cg3i | 0.96 | 2.92 | 3.7920 (18) | 152 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C23H29Cl2NO |
Mr | 406.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 10.0009 (4), 10.8847 (4), 11.0853 (4) |
α, β, γ (°) | 68.161 (1), 70.999 (1), 88.904 (1) |
V (Å3) | 1051.90 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.34 × 0.28 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII DUO CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.900, 0.937 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19180, 6052, 5448 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.703 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.135, 1.15 |
No. of reflections | 6052 |
No. of parameters | 250 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.65, −0.39 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg2 and Cg3 are the centroids of the C2–C7 and C1/C9–C13 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···N1i | 0.89 (2) | 1.99 (2) | 2.8762 (13) | 175 (2) |
C14—H14A···O1i | 0.9800 | 2.5700 | 3.1831 (15) | 121.00 |
C8—H8A···Cg2ii | 0.9700 | 2.9800 | 3.6293 (13) | 126.00 |
C22—H22A···Cg2iii | 0.9700 | 2.8200 | 3.6730 (15) | 148.00 |
C23—H23B···Cg3i | 0.9600 | 2.9200 | 3.7920 (18) | 152.00 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x, y−1, z. |
Acknowledgements
HKF and CSY thank Universiti Sains Malaysia (USM) for the Research University Grant No. 1001/PFIZIK/811160. CSY also thanks USM for the award of a USM Fellowship. AMV is thankful to the management of SeQuent Scientific Ltd, New Mangalore, India, for their invaluable support and allocation of resources for this work. AMI thankful to the Head of the Department of Chemistry and the Director of the National Institute of Technology-Karnataka, Surathkal, India, for providing research facilities.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The fluorene ring is a π-conjugated system that enables facile synthetic manipulation. The synthesis and characterization of fluorene derivatives have attracted much attention in recent years because of their interesting properties and potential applications in various fields, such as two-photon absorption dyes, fluorescent probes, and light-emitting materials (Reinhardt et al., 1998; Yao & Belfield, 2005; Werts et al., 2004; Belfield et al., 2009; Sun et al., 2009; Park et al., 2009; Kotaka et al., 2010; Wong et al., 2005). Fluorene derivatives are also possess biological activities like antimalerial property (Beulter et al., 2007). These diverse applications of fluorene derivatives led us to explore the crystal structure of the title compound.
In the title compound (Fig. 1), the fluorene ring is essentially coplanar with maximum deviation of 0.041 (1) Å at atom C5. The amine group adopts a pyramidal configuration. In the crystal structure, the molecules are linked into dimers (Fig. 2) by intermolecular O1—H1O1···N1 and C14—H14A···O1 hydrogen bonds (Table 1). Weak C—H···π and π···π interactions are observed. Cg1···Cg3ii of 3.7544 (7) Å. Cg1 is centroid of benzene ring C1–C2/C7–C9.