N-(9H-Fluoren-9-yl­idene)-N-(-2-methoxy­phenyl)­amine

The title compound, alternatively called N-(9H-fluoren-9-yl­idene)-2-methoxy­aniline, C₂₀H₁₅NO, was synthesized by the p-toluene­sulfonic acid-assisted Schiff base reaction between 9-fluorenone and 2-methoxy­aniline. The crystal structure of the title compound 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 = 0.051
• wR factor = 0.139
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1997-1999); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 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)-N-(-2-methoxyphenyl)amine

Crystal data

C20H15NO	F(000) = 600
Mr = 285.33	Dx = 1.313 Mg m^−3
Monoclinic, P21/c	Melting point: 407 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.0517 (5) Å	Cell parameters from 12300 reflections
b = 9.3304 (4) Å	θ = 2.2–31.7°
c = 15.6876 (9) Å	µ = 0.08 mm^−1
β = 116.832 (1)°	T = 100 K
V = 1443.49 (12) Å^3	Block, orange
Z = 4	0.6 × 0.6 × 0.5 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3578 independent reflections
Radiation source: sealed tube	3381 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→14
Tmin = 0.951, Tmax = 0.960	k = −12→12
12925 measured reflections	l = −20→20

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0802P)^2 + 0.4989P] where P = (Fo^2 + 2Fc^2)/3
3578 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. Hydrogen atoms were included in calculated positions with a C—H distance of 0.95 Å 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	0.84155 (10)	0.21629 (10)	0.19758 (7)	0.0293 (2)
N1	0.89284 (11)	0.41806 (11)	0.09280 (8)	0.0232 (2)
C1	0.68909 (13)	0.19529 (13)	−0.07085 (9)	0.0225 (3)
H1A	0.7697	0.1428	−0.0340	0.027*
C2	0.57988 (14)	0.13121 (14)	−0.14745 (9)	0.0257 (3)
H2A	0.5868	0.0343	−0.1634	0.031*
C3	0.46097 (14)	0.20717 (15)	−0.20084 (9)	0.0272 (3)
H3A	0.3878	0.1615	−0.2526	0.033*
C4	0.44796 (13)	0.34949 (15)	−0.17924 (9)	0.0257 (3)
H4A	0.3663	0.4008	−0.2152	0.031*
C5	0.48311 (14)	0.67726 (14)	−0.09553 (10)	0.0268 (3)
H5A	0.3939	0.6679	−0.1460	0.032*
C6	0.52862 (15)	0.80676 (14)	−0.04736 (11)	0.0303 (3)
H6A	0.4694	0.8871	−0.0658	0.036*
C7	0.65843 (16)	0.82111 (14)	0.02695 (11)	0.0302 (3)
H7A	0.6870	0.9112	0.0578	0.036*
C8	0.74776 (14)	0.70452 (14)	0.05697 (10)	0.0262 (3)
H8A	0.8361	0.7131	0.1087	0.031*
C9	0.77374 (12)	0.43601 (12)	0.02524 (8)	0.0197 (2)
C10	0.67717 (12)	0.33749 (13)	−0.04984 (8)	0.0199 (2)
C11	0.55665 (12)	0.41459 (13)	−0.10429 (9)	0.0215 (3)
C12	0.57253 (13)	0.56218 (13)	−0.06729 (9)	0.0222 (3)
C13	0.70251 (13)	0.57638 (12)	0.00852 (9)	0.0218 (3)
C14	0.95705 (12)	0.28210 (13)	0.10895 (9)	0.0218 (3)
C15	0.93461 (12)	0.17910 (13)	0.16577 (9)	0.0224 (3)
C16	1.00403 (13)	0.04971 (14)	0.18537 (9)	0.0248 (3)
H16A	0.9889	−0.0203	0.2235	0.030*
C17	1.09583 (13)	0.02271 (14)	0.14901 (9)	0.0271 (3)
H17A	1.1423	−0.0664	0.1619	0.033*
C18	1.11985 (14)	0.12432 (15)	0.09440 (10)	0.0289 (3)
H18A	1.1828	0.1052	0.0700	0.035*
C19	1.05154 (13)	0.25466 (14)	0.07532 (9)	0.0259 (3)
H19A	1.0696	0.3254	0.0390	0.031*
C20	0.81970 (14)	0.11575 (15)	0.25791 (10)	0.0302 (3)
H20A	0.7531	0.1546	0.2769	0.045*
H20B	0.9054	0.0980	0.3150	0.045*
H20C	0.7856	0.0256	0.2232	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0319 (5)	0.0260 (5)	0.0370 (5)	0.0089 (4)	0.0218 (4)	0.0074 (4)
N1	0.0261 (5)	0.0190 (5)	0.0246 (5)	0.0032 (4)	0.0115 (4)	0.0002 (4)
C1	0.0265 (6)	0.0201 (6)	0.0234 (6)	0.0037 (4)	0.0135 (5)	0.0016 (4)
C2	0.0330 (7)	0.0229 (6)	0.0250 (6)	−0.0011 (5)	0.0164 (5)	−0.0028 (5)
C3	0.0281 (6)	0.0311 (7)	0.0221 (6)	−0.0044 (5)	0.0111 (5)	−0.0011 (5)
C4	0.0246 (6)	0.0294 (6)	0.0238 (6)	0.0025 (5)	0.0113 (5)	0.0060 (5)
C5	0.0310 (6)	0.0246 (6)	0.0308 (6)	0.0095 (5)	0.0190 (5)	0.0100 (5)
C6	0.0420 (8)	0.0205 (6)	0.0401 (7)	0.0134 (5)	0.0287 (7)	0.0110 (5)
C7	0.0455 (8)	0.0171 (6)	0.0386 (7)	0.0041 (5)	0.0284 (7)	0.0024 (5)
C8	0.0343 (7)	0.0195 (6)	0.0301 (6)	0.0019 (5)	0.0190 (6)	0.0005 (5)
C9	0.0256 (6)	0.0154 (5)	0.0223 (5)	0.0029 (4)	0.0144 (5)	0.0015 (4)
C10	0.0234 (6)	0.0189 (5)	0.0201 (5)	0.0018 (4)	0.0123 (5)	0.0016 (4)
C11	0.0248 (6)	0.0211 (6)	0.0229 (6)	0.0038 (4)	0.0146 (5)	0.0050 (4)
C12	0.0283 (6)	0.0194 (6)	0.0251 (6)	0.0052 (5)	0.0175 (5)	0.0057 (4)
C13	0.0289 (6)	0.0168 (5)	0.0258 (6)	0.0049 (4)	0.0178 (5)	0.0044 (4)
C14	0.0210 (5)	0.0196 (6)	0.0212 (5)	0.0026 (4)	0.0063 (4)	−0.0006 (4)
C15	0.0199 (5)	0.0231 (6)	0.0223 (6)	0.0026 (4)	0.0077 (4)	−0.0004 (4)
C16	0.0255 (6)	0.0234 (6)	0.0234 (6)	0.0041 (5)	0.0092 (5)	0.0031 (4)
C17	0.0267 (6)	0.0246 (6)	0.0280 (6)	0.0094 (5)	0.0106 (5)	0.0029 (5)
C18	0.0282 (6)	0.0309 (7)	0.0302 (7)	0.0080 (5)	0.0155 (5)	0.0026 (5)
C19	0.0264 (6)	0.0249 (6)	0.0263 (6)	0.0033 (5)	0.0118 (5)	0.0028 (5)
C20	0.0320 (7)	0.0297 (7)	0.0339 (7)	0.0046 (5)	0.0193 (6)	0.0051 (5)

Geometric parameters (Å, º)

O1—C15	1.3750 (15)	C8—C13	1.3835 (18)
O1—C20	1.4284 (16)	C8—H8A	0.9500
N1—C9	1.2746 (16)	C9—C13	1.4891 (15)
N1—C14	1.4194 (15)	C9—C10	1.4955 (17)
C1—C10	1.3877 (16)	C10—C11	1.4122 (16)
C1—C2	1.3960 (18)	C11—C12	1.4738 (17)
C1—H1A	0.9500	C12—C13	1.3976 (18)
C2—C3	1.3919 (19)	C14—C19	1.3898 (18)
C2—H2A	0.9500	C14—C15	1.4069 (17)
C3—C4	1.3938 (19)	C15—C16	1.3885 (17)
C3—H3A	0.9500	C16—C17	1.3929 (18)
C4—C11	1.3854 (18)	C16—H16A	0.9500
C4—H4A	0.9500	C17—C18	1.3815 (19)
C5—C12	1.3895 (17)	C17—H17A	0.9500
C5—C6	1.393 (2)	C18—C19	1.3909 (18)
C5—H5A	0.9500	C18—H18A	0.9500
C6—C7	1.388 (2)	C19—H19A	0.9500
C6—H6A	0.9500	C20—H20A	0.9800
C7—C8	1.4000 (18)	C20—H20B	0.9800
C7—H7A	0.9500	C20—H20C	0.9800
C15—O1—C20	116.91 (10)	C4—C11—C12	130.35 (12)
C9—N1—C14	120.75 (11)	C10—C11—C12	109.00 (11)
C10—C1—C2	118.43 (12)	C5—C12—C13	120.53 (12)
C10—C1—H1A	120.8	C5—C12—C11	130.94 (12)
C2—C1—H1A	120.8	C13—C12—C11	108.52 (10)
C3—C2—C1	120.96 (12)	C8—C13—C12	121.82 (11)
C3—C2—H2A	119.5	C8—C13—C9	129.20 (12)
C1—C2—H2A	119.5	C12—C13—C9	108.97 (10)
C2—C3—C4	120.79 (12)	C19—C14—C15	119.49 (11)
C2—C3—H3A	119.6	C19—C14—N1	119.84 (11)
C4—C3—H3A	119.6	C15—C14—N1	120.44 (11)
C11—C4—C3	118.62 (12)	O1—C15—C16	124.62 (11)
C11—C4—H4A	120.7	O1—C15—C14	115.61 (11)
C3—C4—H4A	120.7	C16—C15—C14	119.76 (11)
C12—C5—C6	117.81 (13)	C15—C16—C17	119.89 (12)
C12—C5—H5A	121.1	C15—C16—H16A	120.1
C6—C5—H5A	121.1	C17—C16—H16A	120.1
C7—C6—C5	121.51 (12)	C18—C17—C16	120.61 (12)
C7—C6—H6A	119.2	C18—C17—H17A	119.7
C5—C6—H6A	119.2	C16—C17—H17A	119.7
C6—C7—C8	120.82 (13)	C17—C18—C19	119.73 (12)
C6—C7—H7A	119.6	C17—C18—H18A	120.1
C8—C7—H7A	119.6	C19—C18—H18A	120.1
C13—C8—C7	117.48 (13)	C14—C19—C18	120.48 (12)
C13—C8—H8A	121.3	C14—C19—H19A	119.8
C7—C8—H8A	121.3	C18—C19—H19A	119.8
N1—C9—C13	121.83 (11)	O1—C20—H20A	109.5
N1—C9—C10	132.55 (11)	O1—C20—H20B	109.5
C13—C9—C10	105.62 (10)	H20A—C20—H20B	109.5
C1—C10—C11	120.54 (12)	O1—C20—H20C	109.5
C1—C10—C9	131.63 (11)	H20A—C20—H20C	109.5
C11—C10—C9	107.84 (10)	H20B—C20—H20C	109.5
C4—C11—C10	120.65 (12)
C10—C1—C2—C3	−0.88 (19)	C7—C8—C13—C12	−0.34 (18)
C1—C2—C3—C4	0.1 (2)	C7—C8—C13—C9	−179.16 (12)
C2—C3—C4—C11	0.92 (19)	C5—C12—C13—C8	−1.06 (18)
C12—C5—C6—C7	−0.50 (19)	C11—C12—C13—C8	179.06 (11)
C5—C6—C7—C8	−0.9 (2)	C5—C12—C13—C9	177.97 (11)
C6—C7—C8—C13	1.31 (19)	C11—C12—C13—C9	−1.90 (13)
C14—N1—C9—C13	178.18 (11)	N1—C9—C13—C8	1.4 (2)
C14—N1—C9—C10	−1.6 (2)	C10—C9—C13—C8	−178.81 (12)
C2—C1—C10—C11	0.63 (18)	N1—C9—C13—C12	−177.56 (11)
C2—C1—C10—C9	−179.36 (12)	C10—C9—C13—C12	2.25 (13)
N1—C9—C10—C1	−2.0 (2)	C9—N1—C14—C19	99.66 (15)
C13—C9—C10—C1	178.26 (12)	C9—N1—C14—C15	−85.84 (15)
N1—C9—C10—C11	178.04 (13)	C20—O1—C15—C16	2.46 (19)
C13—C9—C10—C11	−1.73 (13)	C20—O1—C15—C14	−178.10 (11)
C3—C4—C11—C10	−1.16 (18)	C19—C14—C15—O1	178.69 (11)
C3—C4—C11—C12	178.52 (12)	N1—C14—C15—O1	4.17 (17)
C1—C10—C11—C4	0.39 (18)	C19—C14—C15—C16	−1.83 (18)
C9—C10—C11—C4	−179.62 (11)	N1—C14—C15—C16	−176.36 (11)
C1—C10—C11—C12	−179.36 (10)	O1—C15—C16—C17	179.65 (12)
C9—C10—C11—C12	0.64 (13)	C14—C15—C16—C17	0.23 (19)
C6—C5—C12—C13	1.46 (18)	C15—C16—C17—C18	0.8 (2)
C6—C5—C12—C11	−178.70 (12)	C16—C17—C18—C19	−0.2 (2)
C4—C11—C12—C5	1.2 (2)	C15—C14—C19—C18	2.46 (19)
C10—C11—C12—C5	−179.06 (12)	N1—C14—C19—C18	177.02 (12)
C4—C11—C12—C13	−178.92 (12)	C17—C18—C19—C14	−1.5 (2)
C10—C11—C12—C13	0.79 (13)