Crystal structure of (ferrocenylmeth­yl)di­methyl­ammonium hydrogen oxalate

In the title salt, [Fe(C₅H₅)(C₈H₁₃N)](HC₂O₄), the anions are linked via strong O—H...O hydrogen bonds into linear [100] chains. The cations connect to the anion through bifurcated N—H...(O,O′) hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.022
• wR factor = 0.062
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT051_ALERT_1_C Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .       2.69 %
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.38 Report
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1 Note

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
PLAT164_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct.         17 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT982_ALERT_1_G The  C-f'=     0.015 Deviates from the  IT-value      0.014 Check
PLAT982_ALERT_1_G The Fe-f'=    -0.278 Deviates from the  IT-value     -0.267 Check
PLAT982_ALERT_1_G The  O-f'=     0.041 Deviates from the  IT-value      0.039 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   5 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
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

(Ferrocenylmethyl)dimethylammonium hydrogen oxalate

Crystal data

[Fe(C5H5)(C8H13N)](C2HO4)	Dx = 1.532 Mg m^−3
Mr = 333.16	Ga Kα radiation, λ = 1.34139 Å
Orthorhombic, Pbca	Cell parameters from 9948 reflections
a = 11.2225 (3) Å	θ = 4.8–60.7°
b = 14.8991 (4) Å	µ = 5.72 mm^−1
c = 17.2727 (5) Å	T = 100 K
V = 2888.08 (14) Å^3	Block, clear light orange
Z = 8	0.15 × 0.13 × 0.09 mm
F(000) = 1392

Data collection

Bruker Venture Metaljet diffractometer	3323 independent reflections
Radiation source: Metal Jet, Gallium Liquid Metal Jet Source	3150 reflections with I > 2σ(I)
Helios MX Mirror Optics monochromator	Rint = 0.034
Detector resolution: 10.24 pixels mm^-1	θmax = 60.7°, θmin = 4.5°
ω and φ scans	h = −14→14
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −17→19
Tmin = 0.585, Tmax = 0.752	l = −22→22
56674 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.022	All H-atom parameters refined
wR(F^2) = 0.062	w = 1/[σ^2(Fo^2) + (0.0388P)^2 + 0.8916P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.002
3323 reflections	Δρmax = 0.45 e Å^−3
266 parameters	Δρmin = −0.19 e Å^−3
0 restraints

Special details

Experimental. X-ray crystallographic data for I were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector, a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Fe1	0.34931 (2)	0.64806 (2)	0.49469 (2)	0.01187 (7)
N1	0.11135 (8)	0.53481 (6)	0.31389 (5)	0.01286 (17)
C1	0.22887 (9)	0.57630 (6)	0.43156 (6)	0.01299 (19)
C2	0.17883 (11)	0.60032 (8)	0.50499 (6)	0.0150 (2)
C3	0.25259 (10)	0.56311 (7)	0.56398 (6)	0.0164 (2)
C4	0.34734 (9)	0.51541 (7)	0.52776 (7)	0.0161 (2)
C5	0.33275 (9)	0.52304 (7)	0.44578 (6)	0.0143 (2)
C6	0.35605 (10)	0.77834 (8)	0.45550 (7)	0.0199 (2)
C7	0.35680 (10)	0.77649 (8)	0.53827 (7)	0.0199 (2)
C8	0.45806 (10)	0.72650 (7)	0.56226 (6)	0.0193 (2)
C9	0.52010 (11)	0.69741 (8)	0.49491 (6)	0.0193 (2)
C10	0.45688 (11)	0.72947 (7)	0.42883 (6)	0.0200 (2)
C11	0.18587 (9)	0.60523 (7)	0.35384 (6)	0.0148 (2)
C12	0.07459 (11)	0.56695 (8)	0.23563 (7)	0.0209 (2)
C13	0.00554 (10)	0.50895 (8)	0.36082 (7)	0.0218 (2)
O1	0.30103 (6)	0.41777 (5)	0.27870 (5)	0.01774 (16)
O2	0.38177 (7)	0.28665 (5)	0.24336 (5)	0.01896 (17)
O3	0.15744 (6)	0.21661 (5)	0.23000 (5)	0.01636 (16)
O4	0.08414 (7)	0.35313 (5)	0.25702 (5)	0.01652 (16)
C14	0.29562 (9)	0.33826 (7)	0.25759 (6)	0.01189 (19)
C15	0.16996 (9)	0.29528 (7)	0.24647 (6)	0.01225 (19)
H11A	0.1366 (12)	0.6592 (9)	0.3575 (8)	0.015 (3)*
H5	0.3823 (13)	0.4963 (9)	0.4076 (8)	0.019 (3)*
H9	0.5900 (18)	0.6637 (12)	0.4949 (8)	0.029 (4)*
H4	0.4109 (12)	0.4842 (9)	0.5532 (8)	0.017 (3)*
H6	0.2957 (14)	0.8082 (10)	0.4249 (9)	0.025 (4)*
H1	0.1581 (12)	0.4881 (10)	0.3079 (9)	0.024 (4)*
H2	0.1122 (18)	0.6365 (12)	0.5139 (9)	0.030 (4)*
H11B	0.2507 (12)	0.6154 (9)	0.3202 (8)	0.017 (3)*
H8	0.4786 (14)	0.7118 (10)	0.6155 (9)	0.029 (4)*
H12A	0.0229 (15)	0.6170 (11)	0.2419 (9)	0.032 (4)*
H3	0.2436 (14)	0.5700 (9)	0.6199 (9)	0.027 (4)*
H13A	−0.0415 (15)	0.4691 (11)	0.3319 (9)	0.034 (4)*
H10	0.4764 (15)	0.7189 (10)	0.3752 (9)	0.032 (4)*
H13B	0.0345 (15)	0.4801 (11)	0.4091 (10)	0.033 (4)*
H7	0.2965 (14)	0.8042 (10)	0.5702 (9)	0.028 (4)*
H13C	−0.0372 (14)	0.5622 (10)	0.3732 (9)	0.029 (4)*
H12B	0.1486 (14)	0.5830 (11)	0.2080 (10)	0.031 (4)*
H12C	0.0350 (13)	0.5191 (10)	0.2088 (8)	0.021 (3)*
H4A	0.007 (2)	0.3250 (12)	0.2542 (11)	0.049 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.01085 (10)	0.01291 (10)	0.01184 (10)	−0.00209 (5)	0.00031 (5)	−0.00109 (5)
N1	0.0108 (4)	0.0125 (4)	0.0152 (4)	−0.0001 (3)	−0.0009 (3)	−0.0013 (3)
C1	0.0113 (4)	0.0122 (4)	0.0155 (5)	−0.0030 (4)	0.0000 (4)	−0.0007 (4)
C2	0.0121 (5)	0.0148 (5)	0.0182 (5)	−0.0015 (4)	0.0028 (4)	−0.0012 (4)
C3	0.0174 (5)	0.0168 (5)	0.0150 (5)	−0.0041 (4)	0.0022 (4)	0.0004 (4)
C4	0.0156 (5)	0.0150 (5)	0.0175 (5)	−0.0010 (4)	−0.0016 (4)	0.0016 (4)
C5	0.0122 (4)	0.0145 (5)	0.0160 (5)	−0.0008 (4)	0.0006 (4)	−0.0025 (4)
C6	0.0229 (6)	0.0147 (5)	0.0220 (6)	−0.0039 (4)	−0.0035 (4)	0.0015 (4)
C7	0.0211 (5)	0.0164 (5)	0.0222 (6)	−0.0040 (4)	0.0007 (4)	−0.0064 (4)
C8	0.0200 (5)	0.0206 (5)	0.0173 (5)	−0.0078 (4)	−0.0029 (4)	−0.0012 (4)
C9	0.0131 (5)	0.0184 (5)	0.0264 (6)	−0.0052 (4)	0.0008 (4)	−0.0013 (4)
C10	0.0238 (6)	0.0191 (5)	0.0170 (5)	−0.0093 (4)	0.0039 (4)	−0.0012 (4)
C11	0.0151 (5)	0.0127 (5)	0.0167 (5)	−0.0034 (4)	−0.0027 (4)	0.0002 (4)
C12	0.0258 (6)	0.0178 (5)	0.0189 (5)	0.0016 (4)	−0.0083 (5)	0.0000 (4)
C13	0.0142 (5)	0.0258 (6)	0.0254 (6)	−0.0067 (5)	0.0060 (4)	−0.0091 (5)
O1	0.0121 (3)	0.0154 (3)	0.0257 (4)	−0.0010 (3)	0.0006 (3)	−0.0054 (3)
O2	0.0099 (3)	0.0153 (4)	0.0317 (4)	0.0007 (3)	0.0018 (3)	−0.0011 (3)
O3	0.0143 (4)	0.0129 (3)	0.0219 (4)	−0.0006 (3)	−0.0025 (3)	−0.0002 (3)
O4	0.0088 (3)	0.0149 (4)	0.0258 (4)	0.0005 (3)	−0.0001 (3)	−0.0020 (3)
C14	0.0099 (4)	0.0146 (4)	0.0112 (4)	−0.0006 (4)	−0.0001 (3)	0.0024 (4)
C15	0.0106 (4)	0.0142 (4)	0.0120 (4)	−0.0001 (4)	−0.0008 (3)	0.0022 (4)

Geometric parameters (Å, º)

Fe1—C1	2.0394 (10)	C6—C7	1.4298 (19)
Fe1—C2	2.0490 (12)	C6—C10	1.4223 (17)
Fe1—C3	2.0524 (10)	C6—H6	0.967 (16)
Fe1—C4	2.0574 (11)	C7—C8	1.4206 (17)
Fe1—C5	2.0538 (11)	C7—H7	0.965 (16)
Fe1—C6	2.0570 (12)	C8—C9	1.4233 (16)
Fe1—C7	2.0578 (12)	C8—H8	0.974 (16)
Fe1—C8	2.0536 (11)	C9—C10	1.4263 (16)
Fe1—C9	2.0528 (12)	C9—H9	0.93 (2)
Fe1—C10	2.0549 (11)	C10—H10	0.965 (16)
N1—C11	1.5087 (12)	C11—H11A	0.978 (13)
N1—C12	1.4923 (13)	C11—H11B	0.943 (14)
N1—C13	1.4885 (13)	C12—H12A	0.951 (17)
N1—H1	0.878 (15)	C12—H12B	0.987 (17)
C1—C2	1.4324 (14)	C12—H12C	0.959 (15)
C1—C5	1.4316 (14)	C13—H13A	0.939 (17)
C1—C11	1.4902 (14)	C13—H13B	0.992 (17)
C2—C3	1.4251 (15)	C13—H13C	0.951 (15)
C2—H2	0.935 (19)	O1—C14	1.2410 (12)
C3—C4	1.4237 (15)	O2—C14	1.2595 (13)
C3—H3	0.976 (15)	O3—C15	1.2144 (14)
C4—C5	1.4299 (15)	O4—C15	1.3052 (13)
C4—H4	0.958 (14)	O4—H4A	0.96 (2)
C5—H5	0.950 (15)	C14—C15	1.5607 (14)
C1—Fe1—C2	41.02 (4)	C4—C3—H3	124.4 (9)
C1—Fe1—C3	68.77 (4)	Fe1—C4—H4	125.8 (8)
C1—Fe1—C4	68.76 (4)	C3—C4—Fe1	69.54 (6)
C1—Fe1—C5	40.94 (4)	C3—C4—C5	108.05 (9)
C1—Fe1—C6	110.06 (4)	C3—C4—H4	126.7 (8)
C1—Fe1—C7	135.24 (4)	C5—C4—Fe1	69.51 (6)
C1—Fe1—C8	174.93 (4)	C5—C4—H4	125.3 (8)
C1—Fe1—C9	143.86 (4)	Fe1—C5—H5	127.8 (8)
C1—Fe1—C10	113.75 (4)	C1—C5—Fe1	68.99 (6)
C2—Fe1—C3	40.66 (4)	C1—C5—H5	126.2 (9)
C2—Fe1—C4	68.43 (4)	C4—C5—Fe1	69.78 (6)
C2—Fe1—C5	68.67 (4)	C4—C5—C1	107.89 (9)
C2—Fe1—C6	112.98 (5)	C4—C5—H5	125.9 (9)
C2—Fe1—C7	109.22 (4)	Fe1—C6—H6	126.0 (9)
C2—Fe1—C8	134.68 (4)	C7—C6—Fe1	69.70 (6)
C2—Fe1—C9	174.88 (4)	C7—C6—H6	124.0 (9)
C2—Fe1—C10	143.28 (5)	C10—C6—Fe1	69.68 (6)
C3—Fe1—C4	40.54 (4)	C10—C6—C7	108.02 (10)
C3—Fe1—C5	68.45 (4)	C10—C6—H6	128.0 (9)
C3—Fe1—C6	142.49 (5)	Fe1—C7—H7	125.3 (9)
C3—Fe1—C7	112.44 (5)	C6—C7—Fe1	69.64 (6)
C3—Fe1—C8	109.50 (4)	C6—C7—H7	124.0 (9)
C3—Fe1—C9	135.53 (5)	C8—C7—Fe1	69.63 (6)
C3—Fe1—C10	175.95 (5)	C8—C7—C6	107.85 (10)
C4—Fe1—C7	142.38 (5)	C8—C7—H7	128.2 (9)
C5—Fe1—C4	40.71 (4)	Fe1—C8—H8	123.4 (9)
C5—Fe1—C6	136.37 (5)	C7—C8—Fe1	69.95 (6)
C5—Fe1—C7	175.92 (5)	C7—C8—C9	108.21 (10)
C5—Fe1—C10	111.15 (4)	C7—C8—H8	125.7 (9)
C6—Fe1—C4	176.56 (5)	C9—C8—Fe1	69.69 (6)
C6—Fe1—C7	40.67 (5)	C9—C8—H8	126.0 (9)
C8—Fe1—C4	113.28 (5)	Fe1—C9—H9	126.3 (11)
C8—Fe1—C5	143.48 (5)	C8—C9—Fe1	69.75 (6)
C8—Fe1—C6	68.18 (5)	C8—C9—C10	107.99 (11)
C8—Fe1—C7	40.43 (5)	C8—C9—H9	125.2 (9)
C8—Fe1—C10	68.26 (5)	C10—C9—Fe1	69.76 (6)
C9—Fe1—C4	110.71 (5)	C10—C9—H9	126.8 (9)
C9—Fe1—C5	114.21 (4)	Fe1—C10—H10	124.6 (9)
C9—Fe1—C6	68.18 (5)	C6—C10—Fe1	69.84 (6)
C9—Fe1—C7	68.17 (5)	C6—C10—C9	107.94 (10)
C9—Fe1—C8	40.56 (4)	C6—C10—H10	125.1 (10)
C9—Fe1—C10	40.64 (5)	C9—C10—Fe1	69.60 (6)
C10—Fe1—C4	136.64 (5)	C9—C10—H10	126.9 (10)
C10—Fe1—C6	40.47 (5)	N1—C11—H11A	106.7 (8)
C10—Fe1—C7	68.26 (5)	N1—C11—H11B	104.9 (8)
C11—N1—H1	105.9 (9)	C1—C11—N1	112.98 (8)
C12—N1—C11	110.15 (8)	C1—C11—H11A	111.3 (9)
C12—N1—H1	108.2 (10)	C1—C11—H11B	110.6 (8)
C13—N1—C11	111.91 (8)	H11A—C11—H11B	110.1 (11)
C13—N1—C12	110.84 (9)	N1—C12—H12A	108.5 (9)
C13—N1—H1	109.6 (10)	N1—C12—H12B	106.5 (10)
C2—C1—Fe1	69.85 (6)	N1—C12—H12C	109.1 (8)
C2—C1—C11	126.76 (9)	H12A—C12—H12B	112.3 (14)
C5—C1—Fe1	70.07 (6)	H12A—C12—H12C	110.8 (13)
C5—C1—C2	107.80 (9)	H12B—C12—H12C	109.7 (13)
C5—C1—C11	125.35 (9)	N1—C13—H13A	108.8 (10)
C11—C1—Fe1	123.00 (7)	N1—C13—H13B	107.9 (10)
Fe1—C2—H2	124.2 (11)	N1—C13—H13C	108.0 (9)
C1—C2—Fe1	69.13 (6)	H13A—C13—H13B	111.0 (13)
C1—C2—H2	127.2 (10)	H13A—C13—H13C	111.3 (13)
C3—C2—Fe1	69.80 (6)	H13B—C13—H13C	109.7 (12)
C3—C2—C1	107.95 (10)	C15—O4—H4A	111.6 (11)
C3—C2—H2	124.8 (10)	O1—C14—O2	127.06 (10)
Fe1—C3—H3	124.5 (9)	O1—C14—C15	118.16 (9)
C2—C3—Fe1	69.54 (6)	O2—C14—C15	114.78 (8)
C2—C3—H3	127.3 (9)	O3—C15—O4	125.78 (9)
C4—C3—Fe1	69.92 (6)	O3—C15—C14	121.97 (9)
C4—C3—C2	108.29 (10)	O4—C15—C14	112.25 (8)
Fe1—C1—C2—C3	−59.20 (8)	C5—C1—C11—N1	83.77 (12)
Fe1—C1—C5—C4	59.14 (7)	C6—C7—C8—Fe1	−59.36 (7)
Fe1—C1—C11—N1	171.61 (7)	C6—C7—C8—C9	0.04 (12)
Fe1—C2—C3—C4	−59.38 (7)	C7—C6—C10—Fe1	59.37 (7)
Fe1—C3—C4—C5	−59.03 (7)	C7—C6—C10—C9	−0.03 (12)
Fe1—C4—C5—C1	−58.64 (7)	C7—C8—C9—Fe1	−59.56 (8)
Fe1—C6—C7—C8	59.36 (7)	C7—C8—C9—C10	−0.06 (13)
Fe1—C6—C10—C9	−59.40 (8)	C8—C9—C10—Fe1	−59.50 (8)
Fe1—C7—C8—C9	59.40 (8)	C8—C9—C10—C6	0.05 (13)
Fe1—C8—C9—C10	59.50 (8)	C10—C6—C7—Fe1	−59.36 (7)
Fe1—C9—C10—C6	59.55 (8)	C10—C6—C7—C8	0.00 (11)
C1—C2—C3—Fe1	58.79 (8)	C11—C1—C2—Fe1	−116.75 (10)
C1—C2—C3—C4	−0.59 (13)	C11—C1—C2—C3	−175.95 (9)
C2—C1—C5—Fe1	−59.91 (7)	C11—C1—C5—Fe1	116.95 (10)
C2—C1—C5—C4	−0.78 (11)	C11—C1—C5—C4	176.08 (9)
C2—C1—C11—N1	−99.97 (12)	C12—N1—C11—C1	−178.23 (9)
C2—C3—C4—Fe1	59.15 (8)	C13—N1—C11—C1	57.99 (12)
C2—C3—C4—C5	0.11 (12)	O1—C14—C15—O3	−175.95 (10)
C3—C4—C5—Fe1	59.05 (7)	O1—C14—C15—O4	3.94 (13)
C3—C4—C5—C1	0.41 (11)	O2—C14—C15—O3	4.30 (14)
C5—C1—C2—Fe1	60.05 (7)	O2—C14—C15—O4	−175.81 (9)
C5—C1—C2—C3	0.85 (12)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the Cp ligand C6–C10.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.878 (15)	1.981 (15)	2.8180 (11)	158.9 (14)
N1—H1···O4	0.878 (15)	2.346 (15)	2.8958 (11)	120.8 (11)
C11—H11B···O3^i	0.943 (14)	2.401 (14)	3.2282 (13)	146.3 (11)
C12—H12A···O3^ii	0.951 (17)	2.556 (17)	3.4792 (14)	163.8 (13)
C13—H13A···O4	0.939 (17)	2.578 (16)	3.0631 (14)	112.5 (12)
O4—H4A···O2^iii	0.96 (2)	1.52 (2)	2.4776 (11)	174.1 (18)
C2—H2···Cg2^iv	0.935 (19)	2.743 (19)	3.6564 (13)	165.8 (13)

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