Oxymatrinium tetra­chloridoferrate(III)

He, X.; Wei, X.C.; Tian, Y.C.; Lai, J.X.

doi:10.1107/S1600536812000281

Oxymatrinium tetrachloridoferrate(III)

X. He, X. C. Wei, Y. C. Tian and J. X. Lai

The asymmetric unit of the title compound, (C₁₅H₂₅N₂O₂)[FeCl₄], contains a tetrachloridoferrate(III) anion and a oxymatrinium cation [oxymatrine is (4R,7aS,13aR,13bR,13cS)-dodecahydro-1H,5H,10H-dipyrido[2,1-f:3′,2′,1′-ij][1,6]naphthyridin-10-one 4-oxide]. The conformation of oxymatrine is similar to that of matrine with one ring having a half-chair conformation, while the others have chair conformations. Chiral chains of cations along the c axis are formed by O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812000281/mw2043sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812000281/mw2043Isup2.hkl Contains datablock I

CCDC reference: 867962

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.026
wR factor = 0.061
Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         15
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          5

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           27.08
           From the CIF: _reflns_number_total               4267
           Count of symmetry unique reflns         2470
           Completeness (_total/calc)            172.75%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1797
           Fraction of Friedel pairs measured     0.728
           Are heavy atom types Z>Si present        yes
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          1
PLAT791_ALERT_4_G Note: The Model has Chirality at N1     (Verify)          R
PLAT791_ALERT_4_G Note: The Model has Chirality at C5     (Verify)          S
PLAT791_ALERT_4_G Note: The Model has Chirality at C6     (Verify)          S
PLAT791_ALERT_4_G Note: The Model has Chirality at C7     (Verify)          R
PLAT791_ALERT_4_G Note: The Model has Chirality at C11    (Verify)          R

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

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

Comment top

Oxymatrine is an alkaloid extracted from the Chinese herb Sophora alopecuraides L (Lai et al., 2003). It has been reported that oxymatrine plays important roles as an anti-arrhythmic, in immunity regulation, as an anti-tumor agent among other applications (Song et al., 2006). It is extensively used in China for treatment of viral hepatitis, cancer, cardiac diseases (such as viral myocarditis), and skin diseases (such as psoriasis and eczema) (Wang et al., 2005). A mechanistic study showed that oxymatrine could inhibit apoptotic cell death in hepatocytes (Xiang et al., 2002) as well as scavenge hydroxyradicals and influence ion channels of cardiomyocytes (Sun et al., 2008). The synthesis of similar compounds has been reported (Jin et al., 2005).

The asymmetric unit of (I) is illustrated in Fig. 1. The geometry of the [FeCl₄]^- ion compares favorably with that reported previously (Zhang et al., 2003). In the oxymatrinium cation (oxygen O2 is protonated) (Fig. 1), the D ring (containing atom C15) has a half-chair conformation while the other rings adopt chair forms. The cations are linked via O—H···O hydrogen bonds forming a zigzag chain motif (Fig. 2, Table 1).

Related literature top

For related structures, see: Chen et al. (2011); Jin et al. (2005, 2009); Zhang et al. (2003). For hydrogen-bond motifs see: Bernstein et al. (1995). For the biological activity of oxymatrine, see: Song et al. (2006); Wang et al. (2005); Xiang et al. (2002); Zhang et al. (2001, 2009); Sun et al. (2008). Oxymatrine is an alkaloid extracted from the Chinese herb Sophora alopecuraides L, see: Lai et al. (2003). For the preparation and studies of related salts see: Mao et al. (2008); Li (2006).

Experimental top

A mixture of FeCl₃.6H₂O (0.135 g, 0.5 mmol) and oxymatrine (0.132 g, 0.5 mmol) dissolved in ethanol (20 ml) was refluxed with stirring. A light-yellow precipitate appeared after a few minutes and an aqueous HCl solution (1 M) was added drop-wise until the solution became clear. After standing for two days yellow prismatic crystals were observed which were immediately recovered by filtration and copiously washed with methanol.Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I) with atom labels and 50% probability displacement ellipsoids.
	Fig. 2. Part of the packing of (I) showing the chiral chain running along the c axis. Hydrogen bonds are depicted as dashed lines. H atoms not involved in these interactions have been omitted.

Oxymatrinium tetrachloridoferrate(III) top

Crystal data top

(C₁₅H₂₅N₂O₂)[FeCl₄]	F(000) = 956
M_r = 463.02	D_x = 1.563 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6437 reflections
a = 7.7919 (4) Å	θ = 2.6–27.1°
b = 11.9518 (6) Å	µ = 1.32 mm⁻¹
c = 21.1315 (10) Å	T = 173 K
V = 1967.92 (17) Å³	Prism, yellow
Z = 4	0.45 × 0.26 × 0.25 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	4267 independent reflections
Radiation source: fine-focus sealed tube	3812 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
T_min = 0.588, T_max = 0.734	k = −7→15
9963 measured reflections	l = −23→27

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.061	w = 1/[σ²(F_o²) + (0.0334P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4267 reflections	Δρ_max = 0.31 e Å⁻³
218 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1787 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.006 (14)

Crystal data top

(C₁₅H₂₅N₂O₂)[FeCl₄]	V = 1967.92 (17) Å³
M_r = 463.02	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.7919 (4) Å	µ = 1.32 mm⁻¹
b = 11.9518 (6) Å	T = 173 K
c = 21.1315 (10) Å	0.45 × 0.26 × 0.25 mm

Data collection top

Bruker SMART 1000 CCD diffractometer	4267 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3812 reflections with I > 2σ(I)
T_min = 0.588, T_max = 0.734	R_int = 0.020
9963 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.061	Δρ_max = 0.31 e Å⁻³
S = 1.03	Δρ_min = −0.28 e Å⁻³
4267 reflections	Absolute structure: Flack (1983), 1787 Friedel pairs
218 parameters	Absolute structure parameter: 0.006 (14)
0 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	0.48378 (4)	0.01347 (2)	0.169548 (12)	0.02484 (8)
Cl1	0.48652 (8)	−0.12257 (4)	0.23956 (2)	0.03028 (12)
Cl2	0.72310 (9)	0.10944 (6)	0.17647 (3)	0.04546 (17)
Cl3	0.25496 (9)	0.11672 (6)	0.18583 (3)	0.04688 (18)
Cl4	0.46744 (8)	−0.05810 (5)	0.07447 (2)	0.03739 (14)
N1	1.1039 (2)	0.60782 (15)	0.13234 (8)	0.0221 (4)
C2	1.1716 (3)	0.72196 (19)	0.14985 (10)	0.0276 (5)
H2A	1.2898	0.7305	0.1334	0.033*
H2B	1.1759	0.7290	0.1965	0.033*
C3	1.0591 (3)	0.81319 (19)	0.12295 (11)	0.0298 (5)
H3A	1.0615	0.8094	0.0762	0.036*
H3B	1.1048	0.8870	0.1358	0.036*
C4	0.8751 (3)	0.8018 (2)	0.14585 (11)	0.0325 (5)
H4A	0.8030	0.8576	0.1237	0.039*
H4B	0.8708	0.8189	0.1917	0.039*
C5	0.8001 (3)	0.68571 (19)	0.13492 (10)	0.0259 (5)
H5	0.6964	0.6806	0.1627	0.031*
C6	0.9204 (3)	0.59318 (19)	0.15665 (9)	0.0248 (5)
H6	0.9271	0.5996	0.2038	0.030*
C7	0.8473 (3)	0.47659 (19)	0.14298 (10)	0.0272 (5)
H7	0.7408	0.4703	0.1692	0.033*
C8	0.9697 (3)	0.38652 (19)	0.16806 (11)	0.0381 (5)
H8A	0.9718	0.3896	0.2149	0.046*
H8B	0.9267	0.3118	0.1555	0.046*
C9	1.1505 (3)	0.40203 (19)	0.14288 (12)	0.0366 (6)
H9A	1.2269	0.3446	0.1615	0.044*
H9B	1.1506	0.3921	0.0964	0.044*
C10	1.2176 (3)	0.51723 (19)	0.15907 (10)	0.0298 (5)
H10A	1.2239	0.5253	0.2056	0.036*
H10B	1.3351	0.5258	0.1419	0.036*
C11	0.7893 (3)	0.46034 (17)	0.07363 (9)	0.0235 (4)
H11	0.8923	0.4642	0.0455	0.028*
C12	0.7037 (3)	0.34673 (18)	0.06509 (11)	0.0328 (5)
H12A	0.7916	0.2870	0.0663	0.039*
H12B	0.6216	0.3335	0.1000	0.039*
C13	0.6095 (3)	0.3433 (2)	0.00198 (12)	0.0369 (6)
H13A	0.6897	0.3611	−0.0329	0.044*
H13B	0.5620	0.2675	−0.0054	0.044*
C14	0.4664 (3)	0.4280 (2)	0.00382 (12)	0.0402 (6)
H14A	0.4237	0.4395	−0.0398	0.048*
H14B	0.3706	0.3968	0.0291	0.048*
C15	0.5150 (3)	0.53988 (18)	0.03113 (9)	0.0267 (4)
N16	0.6714 (2)	0.55307 (14)	0.05703 (8)	0.0213 (4)
C17	0.7358 (3)	0.66798 (17)	0.06706 (10)	0.0232 (4)
H17A	0.6427	0.7220	0.0580	0.028*
H17B	0.8308	0.6829	0.0371	0.028*
O1	0.41292 (18)	0.62004 (14)	0.02719 (7)	0.0319 (4)
O2	1.09826 (17)	0.59837 (13)	0.06528 (6)	0.0218 (3)
H2	1.1963	0.6109	0.0503	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.03331 (16)	0.02190 (14)	0.01931 (13)	−0.00039 (14)	0.00051 (12)	−0.00073 (11)
Cl1	0.0359 (3)	0.0272 (2)	0.0277 (2)	−0.0024 (3)	−0.0005 (2)	0.00547 (19)
Cl2	0.0571 (4)	0.0398 (4)	0.0395 (3)	−0.0238 (3)	−0.0061 (3)	0.0081 (3)
Cl3	0.0607 (4)	0.0372 (4)	0.0427 (4)	0.0213 (3)	0.0135 (3)	0.0028 (3)
Cl4	0.0444 (3)	0.0461 (3)	0.0216 (2)	0.0090 (3)	−0.0043 (2)	−0.0082 (2)
N1	0.0239 (8)	0.0255 (9)	0.0169 (8)	−0.0008 (8)	−0.0052 (7)	−0.0010 (8)
C2	0.0260 (11)	0.0290 (12)	0.0277 (11)	−0.0047 (9)	−0.0072 (9)	−0.0038 (10)
C3	0.0318 (12)	0.0205 (10)	0.0372 (12)	−0.0016 (9)	−0.0087 (9)	−0.0025 (9)
C4	0.0284 (11)	0.0307 (13)	0.0383 (13)	0.0028 (10)	−0.0043 (10)	−0.0100 (11)
C5	0.0211 (10)	0.0325 (13)	0.0240 (11)	0.0007 (9)	0.0035 (8)	−0.0054 (9)
C6	0.0249 (10)	0.0335 (12)	0.0160 (10)	−0.0037 (9)	0.0030 (8)	−0.0001 (9)
C7	0.0281 (10)	0.0297 (12)	0.0237 (10)	−0.0040 (10)	0.0018 (8)	0.0046 (10)
C8	0.0486 (14)	0.0297 (11)	0.0359 (12)	−0.0076 (11)	−0.0129 (12)	0.0132 (10)
C9	0.0415 (13)	0.0247 (12)	0.0436 (14)	0.0044 (10)	−0.0142 (11)	0.0045 (11)
C10	0.0322 (11)	0.0299 (12)	0.0272 (11)	0.0048 (10)	−0.0105 (9)	0.0030 (10)
C11	0.0203 (9)	0.0239 (11)	0.0265 (11)	−0.0011 (8)	0.0002 (8)	0.0028 (9)
C12	0.0337 (12)	0.0228 (11)	0.0419 (13)	−0.0032 (10)	−0.0013 (10)	0.0007 (10)
C13	0.0362 (13)	0.0304 (13)	0.0441 (14)	−0.0097 (11)	0.0005 (11)	−0.0084 (11)
C14	0.0318 (13)	0.0401 (13)	0.0487 (14)	−0.0093 (12)	−0.0080 (11)	−0.0059 (11)
C15	0.0210 (10)	0.0336 (11)	0.0257 (10)	−0.0028 (10)	0.0029 (9)	0.0030 (8)
N16	0.0190 (8)	0.0225 (9)	0.0226 (9)	−0.0022 (7)	0.0014 (6)	0.0005 (7)
C17	0.0204 (10)	0.0214 (10)	0.0278 (10)	0.0004 (8)	−0.0010 (9)	−0.0013 (9)
O1	0.0194 (7)	0.0359 (9)	0.0404 (9)	−0.0004 (7)	−0.0015 (6)	0.0040 (8)
O2	0.0190 (7)	0.0307 (8)	0.0157 (6)	−0.0011 (6)	0.0001 (5)	−0.0008 (6)

Geometric parameters (Å, º) top

Fe1—Cl4	2.1874 (6)	C8—H8A	0.9900
Fe1—Cl2	2.1942 (7)	C8—H8B	0.9900
Fe1—Cl3	2.1954 (7)	C9—C10	1.512 (3)
Fe1—Cl1	2.1984 (5)	C9—H9A	0.9900
N1—O2	1.422 (2)	C9—H9B	0.9900
N1—C2	1.509 (3)	C10—H10A	0.9900
N1—C10	1.509 (3)	C10—H10B	0.9900
N1—C6	1.529 (3)	C11—N16	1.482 (3)
C2—C3	1.510 (3)	C11—C12	1.523 (3)
C2—H2A	0.9900	C11—H11	1.0000
C2—H2B	0.9900	C12—C13	1.523 (3)
C3—C4	1.520 (3)	C12—H12A	0.9900
C3—H3A	0.9900	C12—H12B	0.9900
C3—H3B	0.9900	C13—C14	1.507 (3)
C4—C5	1.523 (3)	C13—H13A	0.9900
C4—H4A	0.9900	C13—H13B	0.9900
C4—H4B	0.9900	C14—C15	1.505 (3)
C5—C6	1.521 (3)	C14—H14A	0.9900
C5—C17	1.534 (3)	C14—H14B	0.9900
C5—H5	1.0000	C15—O1	1.248 (3)
C6—C7	1.533 (3)	C15—N16	1.345 (3)
C6—H6	1.0000	N16—C17	1.478 (3)
C7—C8	1.533 (3)	C17—H17A	0.9900
C7—C11	1.546 (3)	C17—H17B	0.9900
C7—H7	1.0000	O2—H2	0.8400
C8—C9	1.518 (4)

Cl4—Fe1—Cl2	108.37 (3)	C7—C8—H8B	109.3
Cl4—Fe1—Cl3	108.45 (3)	H8A—C8—H8B	107.9
Cl2—Fe1—Cl3	112.70 (3)	C10—C9—C8	110.7 (2)
Cl4—Fe1—Cl1	109.23 (2)	C10—C9—H9A	109.5
Cl2—Fe1—Cl1	109.48 (3)	C8—C9—H9A	109.5
Cl3—Fe1—Cl1	108.55 (3)	C10—C9—H9B	109.5
O2—N1—C2	109.09 (15)	C8—C9—H9B	109.5
O2—N1—C10	109.52 (15)	H9A—C9—H9B	108.1
C2—N1—C10	110.59 (15)	N1—C10—C9	111.44 (17)
O2—N1—C6	107.26 (14)	N1—C10—H10A	109.3
C2—N1—C6	110.36 (17)	C9—C10—H10A	109.3
C10—N1—C6	109.95 (16)	N1—C10—H10B	109.3
N1—C2—C3	110.95 (16)	C9—C10—H10B	109.3
N1—C2—H2A	109.4	H10A—C10—H10B	108.0
C3—C2—H2A	109.4	N16—C11—C12	111.55 (17)
N1—C2—H2B	109.4	N16—C11—C7	108.17 (16)
C3—C2—H2B	109.4	C12—C11—C7	110.63 (18)
H2A—C2—H2B	108.0	N16—C11—H11	108.8
C2—C3—C4	111.3 (2)	C12—C11—H11	108.8
C2—C3—H3A	109.4	C7—C11—H11	108.8
C4—C3—H3A	109.4	C13—C12—C11	109.82 (18)
C2—C3—H3B	109.4	C13—C12—H12A	109.7
C4—C3—H3B	109.4	C11—C12—H12A	109.7
H3A—C3—H3B	108.0	C13—C12—H12B	109.7
C3—C4—C5	113.30 (19)	C11—C12—H12B	109.7
C3—C4—H4A	108.9	H12A—C12—H12B	108.2
C5—C4—H4A	108.9	C14—C13—C12	108.42 (19)
C3—C4—H4B	108.9	C14—C13—H13A	110.0
C5—C4—H4B	108.9	C12—C13—H13A	110.0
H4A—C4—H4B	107.7	C14—C13—H13B	110.0
C6—C5—C4	112.33 (17)	C12—C13—H13B	110.0
C6—C5—C17	112.53 (17)	H13A—C13—H13B	108.4
C4—C5—C17	113.14 (19)	C15—C14—C13	114.89 (19)
C6—C5—H5	106.0	C15—C14—H14A	108.5
C4—C5—H5	106.0	C13—C14—H14A	108.5
C17—C5—H5	106.0	C15—C14—H14B	108.5
C5—C6—N1	113.07 (17)	C13—C14—H14B	108.5
C5—C6—C7	112.02 (17)	H14A—C14—H14B	107.5
N1—C6—C7	112.84 (18)	O1—C15—N16	120.96 (19)
C5—C6—H6	106.1	O1—C15—C14	119.75 (19)
N1—C6—H6	106.1	N16—C15—C14	119.22 (19)
C7—C6—H6	106.1	C15—N16—C17	118.37 (17)
C8—C7—C6	110.00 (17)	C15—N16—C11	124.78 (17)
C8—C7—C11	114.93 (19)	C17—N16—C11	116.77 (15)
C6—C7—C11	113.68 (17)	N16—C17—C5	111.93 (17)
C8—C7—H7	105.8	N16—C17—H17A	109.2
C6—C7—H7	105.8	C5—C17—H17A	109.2
C11—C7—H7	105.8	N16—C17—H17B	109.2
C9—C8—C7	111.76 (18)	C5—C17—H17B	109.2
C9—C8—H8A	109.3	H17A—C17—H17B	107.9
C7—C8—H8A	109.3	N1—O2—H2	109.5
C9—C8—H8B	109.3

O2—N1—C2—C3	59.1 (2)	C2—N1—C10—C9	179.15 (19)
C10—N1—C2—C3	179.66 (18)	C6—N1—C10—C9	57.0 (2)
C6—N1—C2—C3	−58.5 (2)	C8—C9—C10—N1	−58.5 (2)
N1—C2—C3—C4	57.9 (2)	C8—C7—C11—N16	179.53 (16)
C2—C3—C4—C5	−52.4 (3)	C6—C7—C11—N16	−52.5 (2)
C3—C4—C5—C6	47.8 (2)	C8—C7—C11—C12	57.1 (2)
C3—C4—C5—C17	−81.0 (2)	C6—C7—C11—C12	−174.92 (18)
C4—C5—C6—N1	−48.8 (2)	N16—C11—C12—C13	45.7 (2)
C17—C5—C6—N1	80.3 (2)	C7—C11—C12—C13	166.21 (18)
C4—C5—C6—C7	−177.63 (17)	C11—C12—C13—C14	−64.4 (2)
C17—C5—C6—C7	−48.6 (2)	C12—C13—C14—C15	44.5 (3)
O2—N1—C6—C5	−64.5 (2)	C13—C14—C15—O1	170.62 (19)
C2—N1—C6—C5	54.2 (2)	C13—C14—C15—N16	−6.5 (3)
C10—N1—C6—C5	176.50 (16)	O1—C15—N16—C17	−14.0 (3)
O2—N1—C6—C7	63.9 (2)	C14—C15—N16—C17	163.0 (2)
C2—N1—C6—C7	−177.34 (16)	O1—C15—N16—C11	169.15 (18)
C10—N1—C6—C7	−55.1 (2)	C14—C15—N16—C11	−13.8 (3)
C5—C6—C7—C8	−177.77 (18)	C12—C11—N16—C15	−6.8 (3)
N1—C6—C7—C8	53.3 (2)	C7—C11—N16—C15	−128.66 (19)
C5—C6—C7—C11	51.7 (2)	C12—C11—N16—C17	176.39 (17)
N1—C6—C7—C11	−77.2 (2)	C7—C11—N16—C17	54.5 (2)
C6—C7—C8—C9	−53.7 (2)	C15—N16—C17—C5	129.11 (19)
C11—C7—C8—C9	76.1 (2)	C11—N16—C17—C5	−53.8 (2)
C7—C8—C9—C10	56.7 (2)	C6—C5—C17—N16	48.7 (2)
O2—N1—C10—C9	−60.6 (2)	C4—C5—C17—N16	177.31 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.84	1.76	2.5935 (19)	171

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	(C₁₅H₂₅N₂O₂)[FeCl₄]
M_r	463.02
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	7.7919 (4), 11.9518 (6), 21.1315 (10)
V (Å³)	1967.92 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.45 × 0.26 × 0.25

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.588, 0.734
No. of measured, independent and observed [I > 2σ(I)] reflections	9963, 4267, 3812
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.061, 1.03
No. of reflections	4267
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.28
Absolute structure	Flack (1983), 1787 Friedel pairs
Absolute structure parameter	0.006 (14)

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008).