N-9H-Fluoren-9-yl­idene-3,4-dimethylaniline

The title compound, C₂₁H₁₇N, was synthesized by the p-toluene­sulfonic acid-assisted Schiff base reaction between 9-fluorenone and 3,4-di­methyl­aniline. The crystal structure has been determined at 100 K.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.054
• wR factor = 0.147
• Data-to-parameter ratio = 18.5

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Computing details

Data collection: SMART (1997-1999); cell refinement: SMART; data reduction: SAINT-Plus (1997–1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

N-9H-Fluoren-9-ylidene-3,4-dimethyaniline

Crystal data

C21H17N	Z = 2
Mr = 283.36	F(000) = 300
Triclinic, P1	Dx = 1.251 Mg m^−3
Hall symbol: -P 1	Melting point: 355.8 K
a = 8.476 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.870 (3) Å	Cell parameters from 6350 reflections
c = 10.376 (4) Å	θ = 2.3–28.4°
α = 78.886 (6)°	µ = 0.07 mm^−1
β = 79.375 (6)°	T = 100 K
γ = 89.483 (6)°	Parallelepiped, orange
V = 752.1 (5) Å^3	0.40 × 0.34 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer	3722 independent reflections
Radiation source: sealed tube	3472 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
/w scans	θmax = 28.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→11
Tmin = 0.967, Tmax = 0.995	k = −11→11
7401 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0842P)^2 + 0.226P] where P = (Fo^2 + 2Fc^2)/3
3722 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. All hydrogen atoms were included in calculated positions with C—H distances of 0.95 Å and 0.98 Å (for aromatic and methyl H atoms respectively) and were included in the refinement in riding motion approximation with U_iso = 1.2U_eq of the carrier atom. Other details are mentioned above in the text.

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.17433 (12)	0.46338 (11)	0.67607 (10)	0.0192 (2)
C1	−0.04904 (13)	0.25424 (13)	0.90276 (11)	0.0185 (2)
H1B	0.0335	0.1957	0.8625	0.022*
C2	−0.16822 (14)	0.18367 (13)	1.00806 (11)	0.0202 (2)
H2A	−0.1672	0.0759	1.0399	0.024*
C3	−0.28873 (14)	0.27017 (14)	1.06676 (12)	0.0216 (3)
H3A	−0.3690	0.2205	1.1385	0.026*
C4	−0.29349 (14)	0.42875 (14)	1.02188 (11)	0.0204 (2)
H4A	−0.3757	0.4874	1.0623	0.024*
C5	−0.23586 (14)	0.78863 (13)	0.86896 (11)	0.0201 (2)
H5A	−0.3286	0.7805	0.9374	0.024*
C6	−0.18410 (15)	0.93022 (14)	0.78815 (12)	0.0219 (3)
H6A	−0.2426	1.0195	0.8015	0.026*
C7	−0.04821 (14)	0.94273 (13)	0.68831 (12)	0.0213 (3)
H7A	−0.0147	1.0405	0.6348	0.026*
C8	0.03990 (14)	0.81344 (13)	0.66552 (11)	0.0190 (2)
H8A	0.1326	0.8222	0.5970	0.023*
C9	0.05504 (13)	0.51429 (12)	0.74783 (11)	0.0158 (2)
C10	−0.05363 (13)	0.41135 (13)	0.85820 (11)	0.0161 (2)
C11	−0.17535 (13)	0.49860 (12)	0.91689 (11)	0.0164 (2)
C12	−0.14870 (13)	0.65976 (13)	0.84713 (11)	0.0168 (2)
C13	−0.01134 (13)	0.67170 (12)	0.74549 (11)	0.0162 (2)
C14	0.27151 (13)	0.56591 (12)	0.56911 (11)	0.0181 (2)
C15	0.40697 (13)	0.63838 (13)	0.59043 (11)	0.0182 (2)
H15A	0.4322	0.6207	0.6775	0.022*
C16	0.50606 (13)	0.73612 (13)	0.48654 (11)	0.0183 (2)
C17	0.47049 (13)	0.76004 (13)	0.35730 (11)	0.0188 (2)
C18	0.33727 (14)	0.68383 (14)	0.33679 (12)	0.0205 (2)
H18A	0.3136	0.6982	0.2493	0.025*
C19	0.23786 (14)	0.58724 (14)	0.44088 (12)	0.0209 (2)
H19A	0.1476	0.5362	0.4245	0.025*
C20	0.65200 (15)	0.81173 (15)	0.51315 (13)	0.0260 (3)
H20A	0.6592	0.7798	0.6076	0.039*
H20B	0.6432	0.9237	0.4917	0.039*
H20C	0.7485	0.7810	0.4574	0.039*
C21	0.57716 (15)	0.86252 (15)	0.24221 (13)	0.0270 (3)
H21A	0.5281	0.8747	0.1625	0.040*
H21B	0.6824	0.8162	0.2244	0.040*
H21C	0.5904	0.9634	0.2648	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0174 (5)	0.0174 (5)	0.0217 (5)	0.0023 (3)	−0.0009 (4)	−0.0039 (4)
C1	0.0185 (5)	0.0173 (5)	0.0202 (5)	0.0028 (4)	−0.0039 (4)	−0.0046 (4)
C2	0.0239 (6)	0.0164 (5)	0.0200 (5)	0.0002 (4)	−0.0051 (4)	−0.0022 (4)
C3	0.0225 (6)	0.0227 (6)	0.0180 (5)	−0.0017 (4)	−0.0004 (4)	−0.0036 (4)
C4	0.0206 (5)	0.0218 (6)	0.0187 (5)	0.0026 (4)	−0.0011 (4)	−0.0063 (4)
C5	0.0204 (5)	0.0208 (6)	0.0206 (5)	0.0049 (4)	−0.0033 (4)	−0.0088 (4)
C6	0.0249 (6)	0.0177 (5)	0.0267 (6)	0.0072 (4)	−0.0085 (5)	−0.0095 (4)
C7	0.0248 (6)	0.0148 (5)	0.0252 (6)	0.0018 (4)	−0.0070 (4)	−0.0041 (4)
C8	0.0185 (5)	0.0176 (5)	0.0214 (5)	0.0015 (4)	−0.0041 (4)	−0.0049 (4)
C9	0.0155 (5)	0.0152 (5)	0.0178 (5)	0.0016 (4)	−0.0046 (4)	−0.0044 (4)
C10	0.0157 (5)	0.0172 (5)	0.0166 (5)	0.0014 (4)	−0.0043 (4)	−0.0054 (4)
C11	0.0172 (5)	0.0168 (5)	0.0169 (5)	0.0021 (4)	−0.0046 (4)	−0.0063 (4)
C12	0.0176 (5)	0.0170 (5)	0.0172 (5)	0.0023 (4)	−0.0043 (4)	−0.0062 (4)
C13	0.0158 (5)	0.0162 (5)	0.0183 (5)	0.0030 (4)	−0.0045 (4)	−0.0062 (4)
C14	0.0168 (5)	0.0150 (5)	0.0212 (5)	0.0048 (4)	−0.0001 (4)	−0.0043 (4)
C15	0.0196 (5)	0.0174 (5)	0.0180 (5)	0.0043 (4)	−0.0017 (4)	−0.0067 (4)
C16	0.0172 (5)	0.0158 (5)	0.0224 (5)	0.0037 (4)	−0.0019 (4)	−0.0068 (4)
C17	0.0175 (5)	0.0157 (5)	0.0216 (5)	0.0055 (4)	−0.0004 (4)	−0.0030 (4)
C18	0.0199 (5)	0.0218 (5)	0.0201 (5)	0.0052 (4)	−0.0054 (4)	−0.0035 (4)
C19	0.0170 (5)	0.0210 (5)	0.0249 (6)	0.0016 (4)	−0.0052 (4)	−0.0039 (4)
C20	0.0240 (6)	0.0246 (6)	0.0303 (6)	−0.0040 (5)	−0.0048 (5)	−0.0073 (5)
C21	0.0232 (6)	0.0262 (6)	0.0267 (6)	0.0015 (5)	0.0003 (5)	0.0020 (5)

Geometric parameters (Å, º)

N1—C9	1.2745 (15)	C9—C13	1.4982 (15)
N1—C14	1.4229 (15)	C10—C11	1.4035 (15)
C1—C10	1.3837 (16)	C11—C12	1.4714 (16)
C1—C2	1.3953 (16)	C12—C13	1.4090 (16)
C1—H1B	0.9500	C14—C19	1.3890 (17)
C2—C3	1.3928 (16)	C14—C15	1.3937 (16)
C2—H2A	0.9500	C15—C16	1.3922 (16)
C3—C4	1.3966 (17)	C15—H15A	0.9500
C3—H3A	0.9500	C16—C17	1.4045 (17)
C4—C11	1.3864 (16)	C16—C20	1.5061 (16)
C4—H4A	0.9500	C17—C18	1.3911 (17)
C5—C12	1.3880 (15)	C17—C21	1.5059 (16)
C5—C6	1.3933 (17)	C18—C19	1.3897 (16)
C5—H5A	0.9500	C18—H18A	0.9500
C6—C7	1.3893 (18)	C19—H19A	0.9500
C6—H6A	0.9500	C20—H20A	0.9800
C7—C8	1.3975 (16)	C20—H20B	0.9800
C7—H7A	0.9500	C20—H20C	0.9800
C8—C13	1.3902 (16)	C21—H21A	0.9800
C8—H8A	0.9500	C21—H21B	0.9800
C9—C10	1.4888 (15)	C21—H21C	0.9800
C9—N1—C14	119.74 (10)	C5—C12—C11	129.79 (10)
C10—C1—C2	118.56 (10)	C13—C12—C11	109.39 (10)
C10—C1—H1B	120.7	C8—C13—C12	120.44 (10)
C2—C1—H1B	120.7	C8—C13—C9	131.69 (10)
C3—C2—C1	120.44 (11)	C12—C13—C9	107.86 (9)
C3—C2—H2A	119.8	C19—C14—C15	119.39 (11)
C1—C2—H2A	119.8	C19—C14—N1	120.24 (10)
C2—C3—C4	121.04 (11)	C15—C14—N1	120.24 (10)
C2—C3—H3A	119.5	C16—C15—C14	121.25 (11)
C4—C3—H3A	119.5	C16—C15—H15A	119.4
C11—C4—C3	118.44 (11)	C14—C15—H15A	119.4
C11—C4—H4A	120.8	C15—C16—C17	119.39 (11)
C3—C4—H4A	120.8	C15—C16—C20	119.78 (11)
C12—C5—C6	118.42 (11)	C17—C16—C20	120.81 (11)
C12—C5—H5A	120.8	C18—C17—C16	118.73 (10)
C6—C5—H5A	120.8	C18—C17—C21	120.55 (11)
C7—C6—C5	120.97 (11)	C16—C17—C21	120.70 (11)
C7—C6—H6A	119.5	C19—C18—C17	121.75 (11)
C5—C6—H6A	119.5	C19—C18—H18A	119.1
C6—C7—C8	120.93 (11)	C17—C18—H18A	119.1
C6—C7—H7A	119.5	C14—C19—C18	119.45 (11)
C8—C7—H7A	119.5	C14—C19—H19A	120.3
C13—C8—C7	118.41 (11)	C18—C19—H19A	120.3
C13—C8—H8A	120.8	C16—C20—H20A	109.5
C7—C8—H8A	120.8	C16—C20—H20B	109.5
N1—C9—C10	121.98 (10)	H20A—C20—H20B	109.5
N1—C9—C13	132.58 (10)	C16—C20—H20C	109.5
C10—C9—C13	105.44 (9)	H20A—C20—H20C	109.5
C1—C10—C11	121.07 (10)	H20B—C20—H20C	109.5
C1—C10—C9	129.78 (10)	C17—C21—H21A	109.5
C11—C10—C9	109.14 (10)	C17—C21—H21B	109.5
C4—C11—C10	120.44 (10)	H21A—C21—H21B	109.5
C4—C11—C12	131.40 (10)	C17—C21—H21C	109.5
C10—C11—C12	108.16 (10)	H21A—C21—H21C	109.5
C5—C12—C13	120.82 (11)	H21B—C21—H21C	109.5
C10—C1—C2—C3	−0.09 (17)	C7—C8—C13—C12	−0.18 (16)
C1—C2—C3—C4	0.09 (18)	C7—C8—C13—C9	−179.54 (11)
C2—C3—C4—C11	0.16 (17)	C5—C12—C13—C8	0.35 (16)
C12—C5—C6—C7	−0.23 (17)	C11—C12—C13—C8	−179.52 (10)
C5—C6—C7—C8	0.41 (18)	C5—C12—C13—C9	179.85 (9)
C6—C7—C8—C13	−0.19 (17)	C11—C12—C13—C9	−0.01 (12)
C14—N1—C9—C10	178.03 (9)	N1—C9—C13—C8	−2.0 (2)
C14—N1—C9—C13	−0.52 (19)	C10—C9—C13—C8	179.26 (11)
C2—C1—C10—C11	−0.16 (16)	N1—C9—C13—C12	178.56 (12)
C2—C1—C10—C9	−178.89 (10)	C10—C9—C13—C12	−0.16 (11)
N1—C9—C10—C1	0.25 (18)	C9—N1—C14—C19	−92.47 (14)
C13—C9—C10—C1	179.14 (11)	C9—N1—C14—C15	91.52 (13)
N1—C9—C10—C11	−178.60 (10)	C19—C14—C15—C16	2.33 (17)
C13—C9—C10—C11	0.29 (11)	N1—C14—C15—C16	178.37 (9)
C3—C4—C11—C10	−0.42 (17)	C14—C15—C16—C17	−1.15 (16)
C3—C4—C11—C12	179.19 (11)	C14—C15—C16—C20	−179.64 (10)
C1—C10—C11—C4	0.42 (16)	C15—C16—C17—C18	−0.53 (16)
C9—C10—C11—C4	179.39 (9)	C20—C16—C17—C18	177.95 (11)
C1—C10—C11—C12	−179.27 (10)	C15—C16—C17—C21	−178.75 (10)
C9—C10—C11—C12	−0.30 (12)	C20—C16—C17—C21	−0.27 (16)
C6—C5—C12—C13	−0.14 (16)	C16—C17—C18—C19	1.04 (17)
C6—C5—C12—C11	179.70 (11)	C21—C17—C18—C19	179.26 (11)
C4—C11—C12—C5	0.7 (2)	C15—C14—C19—C18	−1.80 (17)
C10—C11—C12—C5	−179.65 (11)	N1—C14—C19—C18	−177.84 (10)
C4—C11—C12—C13	−179.45 (11)	C17—C18—C19—C14	0.13 (17)
C10—C11—C12—C13	0.20 (12)