(N-Ferrocenylmeth­yl)dimethyl­ammonium nitrate

The cation of the title compound, [Fe(C₅H₅)(C₈H₁₃N)]NO₃, forms a bifurcated N—H...O hydrogen bond to the nitrate anion.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.067
• wR factor = 0.163
• Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N2
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97.

(N-Ferrocenylmethyl)dimethylammonium nitrate

Crystal data

[Fe(C5H5)(C8H13N)]NO3	F(000) = 640
Mr = 306.14	Dx = 1.471 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4120 reflections
a = 17.4375 (14) Å	θ = 2.4–25.1°
b = 7.4054 (5) Å	µ = 1.10 mm^−1
c = 11.0348 (9) Å	T = 293 K
β = 104.049 (2)°	Block, brown
V = 1382.32 (18) Å^3	0.31 × 0.25 × 0.18 mm
Z = 4

Data collection

Rigaku Weissenberg IP diffractometer	2445 independent reflections
Radiation source: fine-focus sealed tube	1886 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scans	θmax = 25.1°, θmin = 2.4°
Absorption correction: ψ scan (TEXRAY; Molecular Structure Corporation, 1999)	h = −20→14
Tmin = 0.727, Tmax = 0.821	k = −8→6
4660 measured reflections	l = −8→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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.163	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0446P)^2 + 6.2892P] where P = (Fo^2 + 2Fc^2)/3
2406 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

Special details

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	0.35579 (5)	0.52379 (10)	0.30504 (7)	0.0378 (3)
O1	0.0973 (4)	0.7562 (9)	0.5980 (7)	0.118 (3)
O2	0.1167 (4)	0.4799 (8)	0.5513 (5)	0.0933 (19)
O3	0.1241 (3)	0.6883 (7)	0.4251 (5)	0.0756 (15)
N2	0.1118 (3)	0.6436 (8)	0.5255 (6)	0.0573 (14)
N1	0.1262 (3)	0.3027 (6)	0.3241 (4)	0.0443 (12)
H1N	0.1195	0.3949	0.3845	0.07 (2)*
C1	0.2691 (3)	0.3604 (7)	0.3361 (5)	0.0389 (13)
H1A	0.4283	0.8463	0.3723	0.088*
C2	0.2975 (3)	0.4756 (8)	0.4410 (5)	0.0439 (14)
H2A	0.2822	0.8484	0.2586	0.087*
C3	0.3796 (4)	0.4413 (9)	0.4871 (5)	0.0518 (16)
H3A	0.2608	0.6264	0.0821	0.084*
C4	0.4020 (4)	0.3068 (9)	0.4112 (6)	0.0538 (17)
H4A	0.3946	0.4835	0.0817	0.094*
C5	0.3336 (4)	0.2554 (7)	0.3189 (6)	0.0468 (15)
H5A	0.4973	0.6205	0.2626	0.089*
C6	0.4033 (5)	0.7719 (10)	0.3000 (7)	0.074 (2)
C7	0.4408 (4)	0.6496 (12)	0.2397 (8)	0.074 (2)
H7A	0.2661	0.5632	0.4749	0.053*
C8	0.3847 (6)	0.5739 (10)	0.1409 (7)	0.078 (3)
H8A	0.4149	0.5021	0.5580	0.062*
C9	0.3114 (5)	0.6526 (10)	0.1412 (7)	0.070 (2)
H9A	0.4553	0.2576	0.4207	0.065*
C10	0.3232 (5)	0.7735 (9)	0.2367 (8)	0.073 (2)
H10A	0.3316	0.1648	0.2535	0.056*
C11	0.1868 (3)	0.3616 (8)	0.2546 (5)	0.0430 (14)
H11A	0.1843	0.2815	0.1843	0.052*
H11B	0.1740	0.4825	0.2221	0.052*
C12	0.1405 (4)	0.1185 (9)	0.3758 (6)	0.0615 (18)
H12A	0.1925	0.1121	0.4303	0.092*
H12B	0.1363	0.0336	0.3088	0.092*
H12C	0.1019	0.0902	0.4220	0.092*
C13	0.0447 (4)	0.3187 (10)	0.2400 (7)	0.0622 (18)
H13A	0.0063	0.2829	0.2847	0.093*
H13B	0.0405	0.2419	0.1686	0.093*
H13C	0.0352	0.4416	0.2129	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0398 (5)	0.0324 (4)	0.0421 (5)	0.0005 (4)	0.0115 (3)	0.0024 (4)
O1	0.133 (6)	0.106 (5)	0.143 (6)	−0.037 (4)	0.087 (5)	−0.077 (5)
O2	0.142 (6)	0.064 (4)	0.079 (4)	−0.005 (4)	0.035 (4)	0.015 (3)
O3	0.090 (4)	0.070 (3)	0.071 (3)	0.017 (3)	0.027 (3)	0.018 (3)
N1	0.049 (3)	0.039 (3)	0.045 (3)	−0.006 (2)	0.013 (2)	−0.004 (2)
N2	0.053 (3)	0.057 (4)	0.065 (4)	−0.004 (3)	0.020 (3)	−0.006 (3)
C1	0.041 (3)	0.035 (3)	0.043 (3)	−0.004 (2)	0.013 (3)	0.004 (2)
C2	0.042 (3)	0.053 (4)	0.040 (3)	0.003 (3)	0.017 (2)	0.001 (3)
C3	0.056 (4)	0.060 (4)	0.035 (3)	−0.010 (3)	0.004 (3)	0.005 (3)
C4	0.045 (4)	0.047 (4)	0.069 (4)	0.004 (3)	0.015 (3)	0.024 (3)
C5	0.056 (4)	0.028 (3)	0.062 (4)	0.000 (3)	0.025 (3)	0.003 (3)
C6	0.099 (6)	0.045 (4)	0.071 (5)	−0.034 (4)	0.011 (5)	0.002 (4)
C7	0.050 (4)	0.093 (6)	0.082 (6)	−0.005 (4)	0.020 (4)	0.043 (5)
C8	0.137 (8)	0.056 (5)	0.057 (5)	−0.002 (5)	0.054 (5)	0.009 (4)
C9	0.073 (5)	0.055 (5)	0.070 (5)	−0.020 (4)	−0.004 (4)	0.026 (4)
C10	0.080 (6)	0.038 (4)	0.108 (6)	0.009 (4)	0.038 (5)	0.023 (4)
C11	0.044 (3)	0.039 (3)	0.046 (3)	−0.006 (3)	0.009 (3)	0.004 (3)
C12	0.064 (4)	0.059 (4)	0.064 (4)	−0.007 (3)	0.019 (4)	0.021 (3)
C13	0.039 (4)	0.067 (4)	0.078 (5)	−0.002 (3)	0.009 (3)	−0.008 (4)

Geometric parameters (Å, º)

Fe1—C1	2.029 (5)	C11—H11A	0.970
Fe1—C2	2.038 (5)	C11—H11B	0.970
Fe1—C3	2.043 (6)	C6—C7	1.379 (11)
Fe1—C4	2.036 (6)	C6—C10	1.402 (11)
Fe1—C5	2.037 (6)	C6—H1A	0.980
Fe1—C6	2.022 (7)	C3—H8A	0.980
Fe1—C7	2.025 (7)	C13—H13A	0.960
Fe1—C8	2.028 (7)	C13—H13B	0.960
Fe1—C9	2.024 (7)	C13—H13C	0.960
Fe1—C10	2.025 (7)	C7—C8	1.393 (11)
N1—C12	1.476 (8)	C7—H5A	0.980
N1—C13	1.502 (8)	C12—H12A	0.960
N1—C11	1.513 (7)	C12—H12B	0.960
N1—H1N	0.980	C12—H12C	0.960
C5—C1	1.418 (8)	C8—C9	1.405 (11)
C5—C4	1.418 (9)	C8—H4A	0.980
C5—H10A	0.980	C10—C9	1.360 (11)
C2—C3	1.421 (8)	C10—H2A	0.980
C2—C1	1.427 (8)	C9—H3A	0.980
C2—H7A	0.980	N2—O1	1.223 (7)
C1—C11	1.497 (8)	N2—O3	1.225 (7)
C4—C3	1.416 (9)	N2—O2	1.243 (7)
C4—H9A	0.980
C6—Fe1—C9	67.5 (3)	C5—C1—Fe1	69.9 (3)
C6—Fe1—C10	40.5 (3)	C2—C1—Fe1	69.8 (3)
C9—Fe1—C10	39.3 (3)	C11—C1—Fe1	122.7 (4)
C6—Fe1—C7	39.8 (3)	C3—C4—C5	108.0 (6)
C9—Fe1—C7	67.7 (3)	C3—C4—Fe1	70.0 (3)
C10—Fe1—C7	67.1 (3)	C5—C4—Fe1	69.7 (3)
C6—Fe1—C8	67.5 (3)	C3—C4—H9A	126.0
C9—Fe1—C8	40.6 (3)	C5—C4—H9A	126.0
C10—Fe1—C8	67.0 (3)	Fe1—C4—H9A	126.0
C7—Fe1—C8	40.2 (3)	C1—C11—N1	112.3 (4)
C6—Fe1—C1	150.9 (3)	C1—C11—H11A	109.1
C9—Fe1—C1	107.0 (3)	N1—C11—H11A	109.1
C10—Fe1—C1	117.0 (3)	C1—C11—H11B	109.1
C7—Fe1—C1	166.8 (3)	N1—C11—H11B	109.1
C8—Fe1—C1	128.1 (3)	H11A—C11—H11B	107.9
C6—Fe1—C4	128.7 (3)	C7—C6—C10	107.2 (7)
C9—Fe1—C4	153.9 (3)	C7—C6—Fe1	70.2 (4)
C10—Fe1—C4	166.1 (3)	C10—C6—Fe1	69.9 (4)
C7—Fe1—C4	110.3 (3)	C7—C6—H1A	126.4
C8—Fe1—C4	120.6 (3)	C10—C6—H1A	126.4
C1—Fe1—C4	68.8 (2)	Fe1—C6—H1A	126.4
C6—Fe1—C5	167.1 (3)	C4—C3—C2	108.2 (5)
C9—Fe1—C5	119.2 (3)	C4—C3—Fe1	69.4 (3)
C10—Fe1—C5	151.3 (3)	C2—C3—Fe1	69.4 (3)
C7—Fe1—C5	130.1 (3)	C4—C3—H8A	125.9
C8—Fe1—C5	109.8 (3)	C2—C3—H8A	125.9
C1—Fe1—C5	40.8 (2)	Fe1—C3—H8A	125.9
C4—Fe1—C5	40.8 (2)	N1—C13—H13A	109.5
C6—Fe1—C2	117.4 (3)	N1—C13—H13B	109.5
C9—Fe1—C2	126.1 (3)	H13A—C13—H13B	109.5
C10—Fe1—C2	106.8 (3)	N1—C13—H13C	109.5
C7—Fe1—C2	151.8 (3)	H13A—C13—H13C	109.5
C8—Fe1—C2	165.0 (3)	H13B—C13—H13C	109.5
C1—Fe1—C2	41.1 (2)	C6—C7—C8	108.5 (7)
C4—Fe1—C2	68.7 (2)	C6—C7—Fe1	70.0 (4)
C5—Fe1—C2	68.7 (2)	C8—C7—Fe1	70.0 (4)
C6—Fe1—C3	108.2 (3)	C6—C7—H5A	125.8
C9—Fe1—C3	164.0 (3)	C8—C7—H5A	125.8
C10—Fe1—C3	127.6 (3)	Fe1—C7—H5A	125.8
C7—Fe1—C3	119.7 (3)	N1—C12—H12A	109.5
C8—Fe1—C3	153.8 (3)	N1—C12—H12B	109.5
C1—Fe1—C3	68.8 (2)	H12A—C12—H12B	109.5
C4—Fe1—C3	40.6 (3)	N1—C12—H12C	109.5
C5—Fe1—C3	68.4 (3)	H12A—C12—H12C	109.5
C2—Fe1—C3	40.8 (2)	H12B—C12—H12C	109.5
C12—N1—C13	110.9 (5)	C7—C8—C9	107.3 (7)
C12—N1—C11	112.9 (5)	C7—C8—Fe1	69.8 (4)
C13—N1—C11	109.7 (5)	C9—C8—Fe1	69.6 (4)
C12—N1—H1N	114.7	C7—C8—H4A	126.3
C13—N1—H1N	96.5	C9—C8—H4A	126.3
C11—N1—H1N	110.9	Fe1—C8—H4A	126.3
C1—C5—C4	108.2 (5)	C9—C10—C6	109.0 (7)
C1—C5—Fe1	69.3 (3)	C9—C10—Fe1	70.3 (4)
C4—C5—Fe1	69.6 (3)	C6—C10—Fe1	69.6 (4)
C1—C5—H10A	125.9	C9—C10—H2A	125.5
C4—C5—H10A	125.9	C6—C10—H2A	125.5
Fe1—C5—H10A	125.9	Fe1—C10—H2A	125.5
C3—C2—C1	107.7 (5)	C10—C9—C8	107.9 (7)
C3—C2—Fe1	69.8 (3)	C10—C9—Fe1	70.4 (4)
C1—C2—Fe1	69.1 (3)	C8—C9—Fe1	69.9 (4)
C3—C2—H7A	126.1	C10—C9—H3A	126.0
C1—C2—H7A	126.1	C8—C9—H3A	126.0
Fe1—C2—H7A	126.1	Fe1—C9—H3A	126.0
C5—C1—C2	107.8 (5)	O1—N2—O3	121.1 (7)
C5—C1—C11	126.8 (5)	O1—N2—O2	121.9 (7)
C2—C1—C11	125.2 (5)	O3—N2—O2	116.9 (6)
C6—Fe1—C5—C1	158.8 (12)	C3—Fe1—C1—C5	−81.1 (4)
C9—Fe1—C5—C1	−82.2 (5)	C6—Fe1—C1—C2	−51.7 (7)
C10—Fe1—C5—C1	−48.0 (7)	C9—Fe1—C1—C2	−125.9 (4)
C7—Fe1—C5—C1	−166.6 (4)	C10—Fe1—C1—C2	−84.8 (4)
C8—Fe1—C5—C1	−125.9 (4)	C7—Fe1—C1—C2	170.1 (11)
C4—Fe1—C5—C1	119.9 (5)	C8—Fe1—C1—C2	−165.6 (4)
C2—Fe1—C5—C1	38.2 (3)	C4—Fe1—C1—C2	81.4 (4)
C3—Fe1—C5—C1	82.1 (4)	C5—Fe1—C1—C2	118.8 (5)
C6—Fe1—C5—C4	39.0 (14)	C3—Fe1—C1—C2	37.7 (4)
C9—Fe1—C5—C4	157.9 (4)	C6—Fe1—C1—C11	68.0 (7)
C10—Fe1—C5—C4	−167.8 (6)	C9—Fe1—C1—C11	−6.3 (6)
C7—Fe1—C5—C4	73.6 (5)	C10—Fe1—C1—C11	34.9 (6)
C8—Fe1—C5—C4	114.3 (5)	C7—Fe1—C1—C11	−70.3 (13)
C1—Fe1—C5—C4	−119.9 (5)	C8—Fe1—C1—C11	−46.0 (6)
C2—Fe1—C5—C4	−81.7 (4)	C4—Fe1—C1—C11	−158.9 (5)
C3—Fe1—C5—C4	−37.7 (4)	C5—Fe1—C1—C11	−121.6 (6)
C6—Fe1—C2—C3	−86.3 (5)	C2—Fe1—C1—C11	119.6 (6)
C9—Fe1—C2—C3	−167.5 (4)	C3—Fe1—C1—C11	157.3 (5)
C10—Fe1—C2—C3	−128.8 (4)	C1—C5—C4—C3	1.1 (7)
C7—Fe1—C2—C3	−56.1 (7)	Fe1—C5—C4—C3	59.7 (4)
C8—Fe1—C2—C3	168.1 (10)	C1—C5—C4—Fe1	−58.7 (4)
C1—Fe1—C2—C3	119.1 (5)	C6—Fe1—C4—C3	71.3 (5)
C4—Fe1—C2—C3	37.3 (4)	C9—Fe1—C4—C3	−167.2 (6)
C5—Fe1—C2—C3	81.2 (4)	C10—Fe1—C4—C3	36.0 (13)
C6—Fe1—C2—C1	154.5 (4)	C7—Fe1—C4—C3	112.4 (5)
C9—Fe1—C2—C1	73.4 (5)	C8—Fe1—C4—C3	155.7 (4)
C10—Fe1—C2—C1	112.1 (4)	C1—Fe1—C4—C3	−81.6 (4)
C7—Fe1—C2—C1	−175.2 (6)	C5—Fe1—C4—C3	−119.1 (5)
C8—Fe1—C2—C1	49.0 (12)	C2—Fe1—C4—C3	−37.4 (4)
C4—Fe1—C2—C1	−81.8 (4)	C6—Fe1—C4—C5	−169.7 (4)
C5—Fe1—C2—C1	−37.9 (3)	C9—Fe1—C4—C5	−48.2 (8)
C3—Fe1—C2—C1	−119.1 (5)	C10—Fe1—C4—C5	155.1 (11)
C4—C5—C1—C2	−0.9 (6)	C7—Fe1—C4—C5	−128.5 (4)
Fe1—C5—C1—C2	−59.8 (4)	C8—Fe1—C4—C5	−85.2 (5)
C4—C5—C1—C11	175.2 (5)	C1—Fe1—C4—C5	37.4 (3)
Fe1—C5—C1—C11	116.4 (5)	C2—Fe1—C4—C5	81.7 (4)
C4—C5—C1—Fe1	58.8 (4)	C3—Fe1—C4—C5	119.1 (5)
C3—C2—C1—C5	0.4 (6)	C5—C1—C11—N1	118.8 (6)
Fe1—C2—C1—C5	59.8 (4)	C2—C1—C11—N1	−65.7 (7)
C3—C2—C1—C11	−175.8 (5)	Fe1—C1—C11—N1	−152.9 (4)
Fe1—C2—C1—C11	−116.4 (5)	C12—N1—C11—C1	−59.5 (6)
C3—C2—C1—Fe1	−59.4 (4)	C13—N1—C11—C1	176.2 (5)
C6—Fe1—C1—C5	−170.5 (6)	C9—Fe1—C6—C7	−81.6 (5)
C9—Fe1—C1—C5	115.3 (4)	C10—Fe1—C6—C7	−117.8 (7)
C10—Fe1—C1—C5	156.4 (4)	C8—Fe1—C6—C7	−37.5 (5)
C7—Fe1—C1—C5	51.3 (13)	C1—Fe1—C6—C7	−166.3 (5)
C8—Fe1—C1—C5	75.6 (5)	C4—Fe1—C6—C7	74.5 (6)
C4—Fe1—C1—C5	−37.4 (4)	C3—Fe1—C9—C8	158.6 (9)
C2—Fe1—C1—C5	−118.8 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.98	1.96	2.870 (8)	154
N1—H1N···O3	0.98	2.22	3.068 (7)	145