1-Ferrocenyl-N-(1-phenyl­ethyl)ethyl­amine

The title compound, [Fe(C₅H₅)(C₁₅H₁₈N)], has been synthesized as a prochiral agent by refluxing equimolar mixtures of acetyl­ferrocene and 1-phenyl­ethyl­amine followed by reduction with sodium borohydride. The crystal structure exhibits normal geometrical parameters. The C-N-C angle is 118.6 (4)° due to the steric effect of the benzene ring and the substituted ferrocene ring.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.056
• wR factor = 0.127
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1A    ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A    ..  CG3     ..       2.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17A   ..  CG1     ..       3.05 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.99
           From the CIF: _reflns_number_total               3222
           Count of symmetry unique reflns         1931
           Completeness (_total/calc)            166.86%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1291
           Fraction of Friedel pairs measured     0.669
           Are heavy atom types Z>Si present        yes

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

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

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-Ferrocenyl-N-(1-phenylethyl)ethylamine

Crystal data

[Fe(C5H5)(C15H18N)]	F(000) = 704
Mr = 333.24	Dx = 1.300 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1335 reflections
a = 7.3401 (15) Å	θ = 2.2–25.3°
b = 11.688 (2) Å	µ = 0.88 mm^−1
c = 19.841 (4) Å	T = 291 K
V = 1702.1 (6) Å^3	Block, orange
Z = 4	0.27 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3222 independent reflections
Radiation source: sealed tube	2629 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
φ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→9
Tmin = 0.797, Tmax = 0.857	k = −14→14
7239 measured reflections	l = −24→24

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.06P)^2 + 0.66P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
3222 reflections	Δρmax = 0.26 e Å^−3
200 parameters	Δρmin = −0.56 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (3)

Special details

Experimental. Bruker (2000). XSCANS and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

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
Fe1	0.95390 (9)	0.11697 (6)	0.14394 (3)	0.03828 (19)
N1	0.5398 (7)	0.0029 (3)	0.2918 (2)	0.0523 (11)
H1A	0.4433	−0.0374	0.2853	0.063*
C1	1.2167 (7)	0.0644 (4)	0.1559 (3)	0.0495 (13)
H1B	1.2924	0.0722	0.1963	0.059*
C2	1.2039 (7)	0.1425 (4)	0.1011 (3)	0.0466 (13)
H2A	1.2679	0.2158	0.0970	0.056*
C3	1.0815 (7)	0.0952 (5)	0.0540 (3)	0.0484 (14)
H3A	1.0450	0.1315	0.0116	0.058*
C4	1.0205 (8)	−0.0090 (4)	0.0765 (3)	0.0560 (14)
H4A	0.9362	−0.0607	0.0533	0.067*
C5	1.1060 (7)	−0.0280 (5)	0.1386 (3)	0.0549 (14)
H5A	1.0873	−0.0958	0.1668	0.066*
C6	0.8611 (8)	0.1802 (5)	0.2325 (3)	0.0521 (14)
H6A	0.9310	0.1812	0.2746	0.063*
C7	0.8619 (7)	0.2683 (5)	0.1845 (3)	0.0487 (13)
H7A	0.9299	0.3403	0.1873	0.058*
C8	0.7492 (7)	0.2318 (5)	0.1297 (3)	0.0534 (14)
H8A	0.7231	0.2746	0.0883	0.064*
C9	0.6789 (6)	0.1234 (4)	0.1477 (3)	0.0498 (11)
H9A	0.5971	0.0775	0.1196	0.060*
C10	0.7462 (6)	0.0895 (4)	0.2119 (2)	0.0389 (11)
C11	0.7017 (7)	−0.0150 (4)	0.2508 (3)	0.0457 (11)
H11A	0.8040	−0.0311	0.2811	0.055*
C12	0.6695 (7)	−0.1219 (5)	0.2066 (3)	0.0538 (13)
H12A	0.6411	−0.1860	0.2348	0.081*
H12B	0.7776	−0.1381	0.1810	0.081*
H12C	0.5699	−0.1078	0.1763	0.081*
C13	0.5445 (8)	0.0902 (4)	0.3441 (2)	0.0490 (12)
H13A	0.5591	0.1645	0.3218	0.059*
C14	0.6973 (7)	0.0777 (4)	0.3945 (3)	0.0430 (11)
C15	0.7804 (8)	0.1752 (5)	0.4203 (3)	0.0534 (14)
H15A	0.7429	0.2466	0.4051	0.064*
C16	0.9179 (8)	0.1687 (5)	0.4683 (3)	0.0515 (15)
H16A	0.9682	0.2353	0.4860	0.062*
C17	0.9799 (7)	0.0625 (5)	0.4897 (3)	0.0499 (13)
H17A	1.0736	0.0572	0.5211	0.060*
C18	0.8995 (8)	−0.0367 (5)	0.4633 (3)	0.0517 (14)
H18A	0.9397	−0.1085	0.4770	0.062*
C19	0.7605 (8)	−0.0273 (5)	0.4169 (3)	0.0501 (13)
H19A	0.7075	−0.0937	0.4000	0.060*
C20	0.3601 (8)	0.0902 (4)	0.3793 (3)	0.0503 (13)
H20A	0.2654	0.1014	0.3466	0.075*
H20B	0.3565	0.1510	0.4118	0.075*
H20C	0.3423	0.0183	0.4017	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0307 (3)	0.0447 (3)	0.0395 (3)	0.0022 (3)	0.0019 (3)	−0.0042 (3)
N1	0.049 (2)	0.057 (3)	0.051 (2)	−0.027 (2)	0.004 (2)	−0.013 (2)
C1	0.041 (3)	0.052 (3)	0.056 (3)	0.018 (2)	−0.010 (2)	−0.006 (2)
C2	0.045 (3)	0.047 (3)	0.048 (3)	−0.006 (2)	0.032 (2)	−0.001 (2)
C3	0.049 (3)	0.052 (3)	0.045 (3)	0.017 (2)	0.019 (2)	0.002 (2)
C4	0.056 (3)	0.050 (3)	0.062 (3)	0.006 (3)	0.015 (3)	−0.020 (3)
C5	0.052 (3)	0.049 (3)	0.064 (3)	0.018 (2)	0.022 (3)	0.014 (3)
C6	0.047 (3)	0.063 (3)	0.047 (3)	−0.014 (3)	0.000 (2)	−0.015 (3)
C7	0.050 (3)	0.041 (3)	0.055 (3)	0.001 (2)	0.024 (3)	−0.005 (2)
C8	0.052 (3)	0.052 (3)	0.057 (4)	0.025 (2)	0.013 (3)	0.014 (3)
C9	0.041 (2)	0.048 (3)	0.060 (3)	0.005 (2)	0.000 (2)	0.007 (3)
C10	0.027 (2)	0.051 (3)	0.039 (2)	−0.005 (2)	0.0035 (17)	−0.009 (2)
C11	0.046 (3)	0.047 (3)	0.044 (3)	−0.009 (2)	0.004 (2)	−0.004 (2)
C12	0.062 (3)	0.053 (3)	0.046 (3)	−0.018 (3)	0.002 (2)	−0.023 (3)
C13	0.058 (3)	0.045 (3)	0.045 (3)	−0.012 (3)	0.010 (2)	−0.004 (2)
C14	0.043 (3)	0.045 (3)	0.041 (3)	−0.001 (2)	0.012 (2)	−0.001 (2)
C15	0.062 (4)	0.047 (3)	0.051 (3)	0.000 (3)	0.014 (3)	0.002 (2)
C16	0.055 (4)	0.050 (3)	0.049 (3)	−0.022 (3)	0.002 (2)	−0.007 (3)
C17	0.040 (3)	0.070 (4)	0.040 (2)	−0.006 (3)	−0.006 (2)	0.002 (2)
C18	0.056 (3)	0.047 (3)	0.052 (3)	0.021 (2)	−0.005 (2)	0.018 (2)
C19	0.048 (3)	0.049 (3)	0.053 (3)	0.000 (2)	−0.002 (2)	0.014 (2)
C20	0.057 (3)	0.042 (3)	0.051 (3)	−0.001 (2)	0.014 (2)	−0.002 (2)

Geometric parameters (Å, º)

Fe1—C9	2.021 (5)	C8—C9	1.414 (7)
Fe1—C6	2.025 (5)	C8—H8A	0.9800
Fe1—C3	2.032 (5)	C9—C10	1.421 (7)
Fe1—C5	2.032 (5)	C9—H9A	0.9800
Fe1—C8	2.034 (5)	C10—C11	1.481 (7)
Fe1—C1	2.038 (5)	C11—C12	1.545 (6)
Fe1—C2	2.044 (4)	C11—H11A	0.9800
Fe1—C4	2.049 (5)	C12—H12A	0.9600
Fe1—C7	2.057 (5)	C12—H12B	0.9600
Fe1—C10	2.060 (4)	C12—H12C	0.9600
N1—C13	1.455 (6)	C13—C14	1.510 (7)
N1—C11	1.456 (7)	C13—C20	1.523 (7)
N1—H1A	0.8600	C13—H13A	0.9800
C1—C5	1.394 (8)	C14—C19	1.385 (7)
C1—C2	1.422 (7)	C14—C15	1.390 (7)
C1—H1B	0.9800	C15—C16	1.389 (8)
C2—C3	1.410 (8)	C15—H15A	0.9300
C2—H2A	0.9800	C16—C17	1.389 (8)
C3—C4	1.372 (8)	C16—H16A	0.9300
C3—H3A	0.9800	C17—C18	1.402 (8)
C4—C5	1.400 (9)	C17—H17A	0.9300
C4—H4A	0.9800	C18—C19	1.378 (7)
C5—H5A	0.9800	C18—H18A	0.9300
C6—C7	1.402 (8)	C19—H19A	0.9300
C6—C10	1.415 (7)	C20—H20A	0.9600
C6—H6A	0.9800	C20—H20B	0.9600
C7—C8	1.431 (8)	C20—H20C	0.9600
C7—H7A	0.9800
C9—Fe1—C6	67.6 (2)	C1—C5—H5A	124.6
C9—Fe1—C3	119.8 (2)	C4—C5—H5A	124.6
C6—Fe1—C3	164.5 (2)	Fe1—C5—H5A	124.6
C9—Fe1—C5	125.6 (2)	C7—C6—C10	110.8 (5)
C6—Fe1—C5	122.3 (3)	C7—C6—Fe1	71.1 (3)
C3—Fe1—C5	66.2 (2)	C10—C6—Fe1	71.1 (3)
C9—Fe1—C8	40.8 (2)	C7—C6—H6A	124.6
C6—Fe1—C8	68.4 (2)	C10—C6—H6A	124.6
C3—Fe1—C8	107.5 (2)	Fe1—C6—H6A	124.6
C5—Fe1—C8	161.6 (2)	C6—C7—C8	107.2 (5)
C9—Fe1—C1	162.2 (2)	C6—C7—Fe1	68.7 (3)
C6—Fe1—C1	109.1 (2)	C8—C7—Fe1	68.7 (3)
C3—Fe1—C1	68.2 (2)	C6—C7—H7A	126.4
C5—Fe1—C1	40.1 (2)	C8—C7—H7A	126.4
C8—Fe1—C1	156.1 (2)	Fe1—C7—H7A	126.4
C9—Fe1—C2	155.0 (2)	C9—C8—C7	106.6 (5)
C6—Fe1—C2	127.5 (2)	C9—C8—Fe1	69.1 (3)
C3—Fe1—C2	40.5 (2)	C7—C8—Fe1	70.4 (3)
C5—Fe1—C2	66.9 (2)	C9—C8—H8A	126.7
C8—Fe1—C2	120.6 (2)	C7—C8—H8A	126.7
C1—Fe1—C2	40.8 (2)	Fe1—C8—H8A	126.7
C9—Fe1—C4	106.8 (2)	C8—C9—C10	110.4 (5)
C6—Fe1—C4	155.4 (2)	C8—C9—Fe1	70.1 (3)
C3—Fe1—C4	39.3 (2)	C10—C9—Fe1	71.1 (3)
C5—Fe1—C4	40.1 (2)	C8—C9—H9A	124.8
C8—Fe1—C4	124.0 (3)	C10—C9—H9A	124.8
C1—Fe1—C4	68.5 (2)	Fe1—C9—H9A	124.8
C2—Fe1—C4	67.6 (2)	C6—C10—C9	105.0 (4)
C9—Fe1—C7	68.0 (2)	C6—C10—C11	126.7 (5)
C6—Fe1—C7	40.2 (2)	C9—C10—C11	128.3 (4)
C3—Fe1—C7	127.1 (2)	C6—C10—Fe1	68.4 (3)
C5—Fe1—C7	156.6 (3)	C9—C10—Fe1	68.2 (3)
C8—Fe1—C7	40.9 (2)	C11—C10—Fe1	129.2 (3)
C1—Fe1—C7	121.6 (2)	N1—C11—C10	110.7 (4)
C2—Fe1—C7	109.4 (2)	N1—C11—C12	108.0 (4)
C4—Fe1—C7	162.1 (2)	C10—C11—C12	113.9 (4)
C9—Fe1—C10	40.8 (2)	N1—C11—H11A	108.0
C6—Fe1—C10	40.53 (19)	C10—C11—H11A	108.0
C3—Fe1—C10	153.7 (2)	C12—C11—H11A	108.0
C5—Fe1—C10	108.1 (2)	C11—C12—H12A	109.5
C8—Fe1—C10	69.3 (2)	C11—C12—H12B	109.5
C1—Fe1—C10	125.3 (2)	H12A—C12—H12B	109.5
C2—Fe1—C10	163.5 (2)	C11—C12—H12C	109.5
C4—Fe1—C10	119.5 (2)	H12A—C12—H12C	109.5
C7—Fe1—C10	68.58 (19)	H12B—C12—H12C	109.5
C13—N1—C11	118.6 (4)	N1—C13—C14	115.0 (5)
C13—N1—H1A	120.7	N1—C13—C20	107.8 (4)
C11—N1—H1A	120.7	C14—C13—C20	110.8 (4)
C5—C1—C2	105.7 (5)	N1—C13—H13A	107.7
C5—C1—Fe1	69.7 (3)	C14—C13—H13A	107.7
C2—C1—Fe1	69.8 (3)	C20—C13—H13A	107.7
C5—C1—H1B	127.1	C19—C14—C15	117.4 (5)
C2—C1—H1B	127.1	C19—C14—C13	123.2 (5)
Fe1—C1—H1B	127.1	C15—C14—C13	119.4 (5)
C3—C2—C1	107.3 (4)	C16—C15—C14	121.8 (5)
C3—C2—Fe1	69.3 (3)	C16—C15—H15A	119.1
C1—C2—Fe1	69.4 (3)	C14—C15—H15A	119.1
C3—C2—H2A	126.4	C15—C16—C17	119.7 (5)
C1—C2—H2A	126.4	C15—C16—H16A	120.1
Fe1—C2—H2A	126.4	C17—C16—H16A	120.1
C4—C3—C2	109.9 (5)	C16—C17—C18	119.2 (5)
C4—C3—Fe1	71.0 (3)	C16—C17—H17A	120.4
C2—C3—Fe1	70.2 (3)	C18—C17—H17A	120.4
C4—C3—H3A	125.1	C19—C18—C17	119.7 (5)
C2—C3—H3A	125.1	C19—C18—H18A	120.2
Fe1—C3—H3A	125.1	C17—C18—H18A	120.2
C3—C4—C5	106.3 (5)	C18—C19—C14	122.2 (5)
C3—C4—Fe1	69.7 (3)	C18—C19—H19A	118.9
C5—C4—Fe1	69.3 (3)	C14—C19—H19A	118.9
C3—C4—H4A	126.8	C13—C20—H20A	109.5
C5—C4—H4A	126.8	C13—C20—H20B	109.5
Fe1—C4—H4A	126.8	H20A—C20—H20B	109.5
C1—C5—C4	110.8 (5)	C13—C20—H20C	109.5
C1—C5—Fe1	70.2 (3)	H20A—C20—H20C	109.5
C4—C5—Fe1	70.6 (3)	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···Cg3^i	0.98	2.99	3.819 (6)	143
C17—H17A···Cg1^ii	0.93	3.05	3.932 (6)	158

Symmetry codes: (i) −x+3/2, −y, z−1/2; (ii) −x+5/2, −y, z+1/2.