N-(9H-Fluoren-9-yl­idene)-N-(4-methoxy­phenyl)­amine

The title compound, C₂₀H₁₅NO, was synthesized by the p-toluene­sulfonic acid-assisted Schiff base reaction between 9-fluorenone and 4-methoxy­aniline. The crystal structure of the title compound has been determined at 100 K.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• R factor = 0.042
• wR factor = 0.115
• Data-to-parameter ratio = 17.9

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

N-9H-fluoren-9-ylidene-N-(4-methoxyphenyl)amine

Crystal data

C20H15NO	F(000) = 1200
Mr = 285.33	Dx = 1.319 Mg m^−3
Monoclinic, C2/c	Melting point: 404 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 19.0275 (10) Å	Cell parameters from 14878 reflections
b = 9.8262 (5) Å	θ = 2.4–28.3°
c = 17.4862 (10) Å	µ = 0.08 mm^−1
β = 118.486 (1)°	T = 100 K
V = 2873.5 (3) Å^3	Parallelepiped, orange
Z = 8	0.60 × 0.56 × 0.35 mm

Data collection

Bruker SMART APEX CCD diffractometer	3565 independent reflections
Radiation source: fine-focus sealed tube	3287 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
ω scans	θmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS in SAINT+; Bruker, 1997–1999)	h = −25→25
Tmin = 0.922, Tmax = 0.968	k = −13→13
14415 measured reflections	l = −23→23

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0646P)^2 + 1.5364P] where P = (Fo^2 + 2Fc^2)/3
3565 reflections	(Δ/σ)max = 0.003
199 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. All hydrogen atoms were included in calculated positions with aromatic C—H and methyl C—H distances of 0.95 Å and 0.98 Å, respectively, and were included in the refinement in riding motion approximation with U_iso = 1.2U_eq of the carrier atom.

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
O1	0.11641 (4)	0.49833 (7)	0.18984 (5)	0.02016 (17)
N1	0.15358 (5)	1.02690 (9)	0.09761 (5)	0.01828 (19)
C19	0.06690 (6)	0.82948 (10)	0.07573 (6)	0.0193 (2)
H19A	0.0225	0.8780	0.0326	0.023*
C9	0.14305 (5)	1.06652 (10)	0.02309 (6)	0.0161 (2)
C18	0.05559 (6)	0.69902 (10)	0.09946 (6)	0.0182 (2)
H18A	0.0038	0.6593	0.0730	0.022*
C10	0.12514 (5)	0.99313 (10)	−0.05937 (6)	0.0163 (2)
C15	0.20692 (6)	0.81758 (10)	0.17869 (6)	0.0187 (2)
H15A	0.2583	0.8586	0.2068	0.022*
C14	0.14225 (6)	0.88951 (10)	0.11424 (6)	0.0173 (2)
C16	0.19662 (6)	0.68730 (10)	0.20184 (6)	0.0188 (2)
H16A	0.2411	0.6385	0.2447	0.023*
C7	0.17963 (6)	1.44972 (11)	0.03076 (7)	0.0211 (2)
H7A	0.1937	1.5270	0.0678	0.025*
C12	0.13805 (6)	1.22669 (10)	−0.07956 (6)	0.0166 (2)
C13	0.15141 (5)	1.21239 (10)	0.00612 (6)	0.0166 (2)
C5	0.14565 (6)	1.35275 (10)	−0.11066 (6)	0.0193 (2)
H5A	0.1364	1.3632	−0.1688	0.023*
C17	0.12078 (6)	0.62765 (10)	0.16219 (6)	0.0167 (2)
C4	0.10922 (6)	1.05372 (10)	−0.20211 (6)	0.0198 (2)
H4A	0.1055	1.1205	−0.2432	0.024*
C1	0.11852 (6)	0.85569 (10)	−0.08048 (6)	0.0198 (2)
H1A	0.1214	0.7886	−0.0400	0.024*
C11	0.12147 (6)	1.09117 (10)	−0.12024 (6)	0.0168 (2)
C8	0.17144 (6)	1.32305 (10)	0.06162 (6)	0.0192 (2)
H8A	0.1794	1.3130	0.1192	0.023*
C3	0.10248 (6)	0.91581 (11)	−0.22273 (7)	0.0220 (2)
H3A	0.0944	0.8880	−0.2784	0.026*
C2	0.10751 (6)	0.81826 (11)	−0.16263 (7)	0.0223 (2)
H2A	0.1034	0.7246	−0.1777	0.027*
C6	0.16730 (6)	1.46373 (10)	−0.05415 (7)	0.0208 (2)
H6A	0.1738	1.5505	−0.0739	0.025*
C20	0.04077 (7)	0.43231 (11)	0.14680 (7)	0.0262 (2)
H20A	0.0449	0.3414	0.1717	0.039*
H20B	0.0242	0.4241	0.0846	0.039*
H20C	0.0011	0.4859	0.1544	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0201 (4)	0.0173 (4)	0.0197 (4)	0.0012 (3)	0.0067 (3)	0.0029 (3)
N1	0.0187 (4)	0.0204 (4)	0.0156 (4)	−0.0005 (3)	0.0082 (3)	0.0007 (3)
C19	0.0181 (4)	0.0221 (5)	0.0160 (4)	0.0024 (4)	0.0068 (4)	0.0038 (4)
C9	0.0138 (4)	0.0181 (4)	0.0162 (4)	0.0004 (3)	0.0070 (3)	−0.0002 (3)
C18	0.0159 (4)	0.0215 (5)	0.0165 (4)	0.0002 (3)	0.0071 (4)	0.0010 (3)
C10	0.0158 (4)	0.0191 (5)	0.0147 (4)	0.0001 (3)	0.0077 (4)	0.0002 (3)
C15	0.0164 (4)	0.0230 (5)	0.0155 (4)	−0.0003 (3)	0.0067 (4)	−0.0016 (3)
C14	0.0205 (4)	0.0196 (5)	0.0137 (4)	0.0005 (4)	0.0097 (4)	−0.0001 (3)
C16	0.0176 (4)	0.0209 (5)	0.0154 (4)	0.0033 (3)	0.0060 (4)	0.0001 (3)
C7	0.0204 (5)	0.0191 (5)	0.0232 (5)	0.0016 (4)	0.0100 (4)	−0.0034 (4)
C12	0.0151 (4)	0.0185 (5)	0.0166 (4)	0.0012 (3)	0.0080 (3)	0.0001 (3)
C13	0.0147 (4)	0.0182 (5)	0.0173 (4)	0.0013 (3)	0.0080 (4)	0.0011 (3)
C5	0.0203 (4)	0.0192 (5)	0.0197 (5)	0.0025 (4)	0.0107 (4)	0.0024 (4)
C17	0.0195 (4)	0.0167 (4)	0.0148 (4)	0.0018 (3)	0.0090 (4)	0.0005 (3)
C4	0.0225 (5)	0.0214 (5)	0.0173 (5)	−0.0018 (4)	0.0110 (4)	0.0005 (4)
C1	0.0226 (5)	0.0189 (5)	0.0189 (5)	−0.0010 (4)	0.0108 (4)	0.0010 (4)
C11	0.0159 (4)	0.0177 (4)	0.0174 (4)	0.0001 (3)	0.0086 (4)	0.0006 (3)
C8	0.0188 (4)	0.0213 (5)	0.0175 (4)	0.0020 (4)	0.0087 (4)	−0.0012 (4)
C3	0.0261 (5)	0.0234 (5)	0.0180 (4)	−0.0028 (4)	0.0119 (4)	−0.0036 (4)
C2	0.0281 (5)	0.0189 (5)	0.0211 (5)	−0.0024 (4)	0.0128 (4)	−0.0033 (4)
C6	0.0210 (5)	0.0163 (5)	0.0258 (5)	0.0021 (4)	0.0119 (4)	0.0018 (4)
C20	0.0228 (5)	0.0228 (5)	0.0282 (5)	−0.0030 (4)	0.0082 (4)	0.0052 (4)

Geometric parameters (Å, º)

O1—C17	1.3761 (11)	C7—H7A	0.9500
O1—C20	1.4231 (13)	C12—C5	1.3879 (13)
N1—C9	1.2808 (12)	C12—C13	1.4021 (13)
N1—C14	1.4189 (13)	C12—C11	1.4713 (13)
C19—C14	1.3914 (14)	C13—C8	1.3844 (13)
C19—C18	1.3954 (14)	C5—C6	1.3954 (14)
C19—H19A	0.9500	C5—H5A	0.9500
C9—C13	1.4876 (13)	C4—C11	1.3859 (13)
C9—C10	1.4989 (13)	C4—C3	1.3924 (14)
C18—C17	1.3914 (13)	C4—H4A	0.9500
C18—H18A	0.9500	C1—C2	1.3986 (14)
C10—C1	1.3898 (14)	C1—H1A	0.9500
C10—C11	1.4124 (13)	C8—H8A	0.9500
C15—C16	1.3845 (14)	C3—C2	1.3915 (14)
C15—C14	1.4003 (13)	C3—H3A	0.9500
C15—H15A	0.9500	C2—H2A	0.9500
C16—C17	1.3971 (14)	C6—H6A	0.9500
C16—H16A	0.9500	C20—H20A	0.9800
C7—C8	1.3947 (14)	C20—H20B	0.9800
C7—C6	1.3950 (14)	C20—H20C	0.9800
C17—O1—C20	116.78 (8)	C12—C5—H5A	121.0
C9—N1—C14	122.16 (9)	C6—C5—H5A	121.0
C14—C19—C18	121.00 (9)	O1—C17—C18	124.19 (9)
C14—C19—H19A	119.5	O1—C17—C16	115.74 (8)
C18—C19—H19A	119.5	C18—C17—C16	120.08 (9)
N1—C9—C13	121.07 (9)	C11—C4—C3	118.38 (9)
N1—C9—C10	133.31 (9)	C11—C4—H4A	120.8
C13—C9—C10	105.57 (8)	C3—C4—H4A	120.8
C17—C18—C19	119.44 (9)	C10—C1—C2	118.59 (9)
C17—C18—H18A	120.3	C10—C1—H1A	120.7
C19—C18—H18A	120.3	C2—C1—H1A	120.7
C1—C10—C11	119.80 (9)	C4—C11—C10	121.38 (9)
C1—C10—C9	132.31 (9)	C4—C11—C12	129.15 (9)
C11—C10—C9	107.68 (8)	C10—C11—C12	109.32 (8)
C16—C15—C14	120.63 (9)	C13—C8—C7	118.29 (9)
C16—C15—H15A	119.7	C13—C8—H8A	120.9
C14—C15—H15A	119.7	C7—C8—H8A	120.9
C19—C14—C15	118.85 (9)	C2—C3—C4	120.67 (9)
C19—C14—N1	121.76 (9)	C2—C3—H3A	119.7
C15—C14—N1	118.95 (9)	C4—C3—H3A	119.7
C15—C16—C17	119.97 (9)	C3—C2—C1	121.15 (10)
C15—C16—H16A	120.0	C3—C2—H2A	119.4
C17—C16—H16A	120.0	C1—C2—H2A	119.4
C8—C7—C6	120.45 (9)	C7—C6—C5	121.31 (9)
C8—C7—H7A	119.8	C7—C6—H6A	119.3
C6—C7—H7A	119.8	C5—C6—H6A	119.3
C5—C12—C13	120.57 (9)	O1—C20—H20A	109.5
C5—C12—C11	131.05 (9)	O1—C20—H20B	109.5
C13—C12—C11	108.28 (8)	H20A—C20—H20B	109.5
C8—C13—C12	121.29 (9)	O1—C20—H20C	109.5
C8—C13—C9	129.56 (9)	H20A—C20—H20C	109.5
C12—C13—C9	109.12 (8)	H20B—C20—H20C	109.5
C12—C5—C6	118.08 (9)