Supra­molecular architectures in the salt trimethoprimium ferrocene-1-carboxyl­ate and the cocrystal 4-amino-5-chloro-2,6-di­methyl­pyrimidine–ferrocene-1-carb­oxy­lic acid (1/1)

Swinton Darious, R.; Thomas Muthiah, P.; Perdih, F.

doi:10.1107/S2053229617011913

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Supramolecular architectures in the salt trimethoprimium ferrocene-1-carboxylate and the cocrystal 4-amino-5-chloro-2,6-dimethylpyrimidine–ferrocene-1-carboxylic acid (1/1)

R. Swinton Darious, P. Thomas Muthiah and F. Perdih

In the salt trimethoprimium ferrocenecarboxylate [systematic name: 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium ferrocene-1-carboxylate], (C₁₄H₁₉N₄O₃)[Fe(C₅H₅)(C₆H₄O₂)], (I), of the antibacterial compound trimethoprim, the carboxylate group interacts with the protonated aminopyrimidine group of trimethoprim via two N—H

O hydrogen bonds, generating a robust R₂²(8) ring motif (heterosynthon). However, in the cocrystal 4-amino-5-chloro-2,6-dimethylpyrimidine–ferrocene-1-carboxylic acid (1/1), [Fe(C₅H₅)(C₆H₅O₂)]·C₆H₈ClN₃, (II), the carboxyl–aminopyrimidine interaction [R₂²(8) motif] is absent. The carboxyl group interacts with the pyrimidine ring via a single O—H

N hydrogen bond. The pyrimidine rings, however, form base pairs via a pair of N—H

N hydrogen bonds, generating an R₂²(8) supramolecular homosynthon. In salt (I), the unsubstituted cyclopentadienyl ring is disordered over two positions, with a refined site-occupation ratio of 0.573 (10):0.427 (10). In this study, the two five-membered cyclopentadienyl (Cp) rings of ferrocene are in a staggered conformation, as is evident from the C

C pseudo-torsion angles, which are in the range 36.13–37.53° for (I) and 22.58–23.46° for (II). Regarding the Cp ring of the minor component in salt (I), the geometry of the ferrocene ring is in an eclipsed conformation, as is evident from the C

C pseudo-torsion angles, which are in the range 79.26–80.94°. Both crystal structures are further stabilized by weak π–π interactions.

Keywords: trimethoprim; ferrocene-1-carboxylic acid; cocrystal; salt; supramolecular architectures; π–π stacking interactions; eclipsed; staggered; crystal structure; antibacterial compound.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617011913/ku3202sup1.cif Contains datablocks I, II
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229617011913/ku3202Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229617011913/ku3202IIsup3.hkl Contains datablock II

CCDC references: 1569235; 1569234

Computing details top

For both structures, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium ferrocene-1-carboxylate (I) top

Crystal data top

(C₁₄H₁₉N₄O₃)[Fe(C₅H₅)(C₆H₄O₂)]	F(000) = 1088
M_r = 520.36	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.3583 (2) Å	Cell parameters from 9929 reflections
b = 13.1393 (3) Å	θ = 3.9–29.8°
c = 17.7722 (4) Å	µ = 0.67 mm⁻¹
β = 92.291 (2)°	T = 293 K
V = 2416.88 (9) Å³	Prism, orange
Z = 4	0.20 × 0.18 × 0.12 mm

Data collection top

Agilent SuperNova Dual Source diffractometer with an Atlas detector	5532 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4661 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.025
Detector resolution: 10.4933 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −17→17
T_min = 0.888, T_max = 1.000	l = −22→23
22853 measured reflections

Refinement top

Refinement on F²	65 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0374P)² + 1.0417P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
5532 reflections	Δρ_max = 0.29 e Å⁻³
380 parameters	Δρ_min = −0.26 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Fe1	0.89753 (2)	0.35264 (2)	0.28429 (2)	0.03347 (9)
O10	0.23223 (15)	0.45715 (11)	−0.02959 (8)	0.0504 (4)
O11	0.36542 (13)	0.60489 (11)	−0.10063 (7)	0.0418 (3)
O12	0.38883 (16)	0.78851 (11)	−0.04493 (8)	0.0545 (4)
N1	0.36468 (14)	0.56069 (12)	0.30455 (8)	0.0315 (3)
H1	0.4201 (17)	0.5125 (14)	0.3016 (11)	0.038*
N2	0.38288 (19)	0.55051 (17)	0.43304 (9)	0.0525 (5)
H2A	0.367 (2)	0.5739 (18)	0.4764 (9)	0.063*
H2B	0.452 (2)	0.513 (2)	0.4268 (14)	0.063*
N3	0.22436 (14)	0.65420 (11)	0.37945 (8)	0.0332 (3)
N4	0.06909 (15)	0.75512 (13)	0.32431 (9)	0.0371 (3)
H4A	0.0403 (19)	0.7634 (16)	0.3680 (8)	0.045*
H4B	0.029 (2)	0.7868 (16)	0.2860 (12)	0.045*
C2	0.32288 (16)	0.58995 (14)	0.37236 (9)	0.0323 (4)
C4	0.16645 (15)	0.69117 (12)	0.31625 (9)	0.0271 (3)
C5	0.20534 (15)	0.66280 (12)	0.24231 (9)	0.0262 (3)
C6	0.30454 (15)	0.59710 (13)	0.24068 (9)	0.0297 (3)
H6	0.3331	0.5758	0.1943	0.036*
C7	0.12945 (16)	0.70021 (15)	0.17324 (9)	0.0333 (4)
H7A	0.1213	0.7736	0.1763	0.040*
H7B	0.0431	0.6716	0.1734	0.040*
C8	0.18928 (16)	0.67319 (14)	0.09954 (9)	0.0302 (3)
C9	0.17956 (17)	0.57484 (14)	0.07094 (9)	0.0338 (4)
H9	0.1340	0.5255	0.0964	0.041*
C10	0.23812 (17)	0.55041 (13)	0.00416 (9)	0.0335 (4)
C11	0.30972 (17)	0.62370 (14)	−0.03303 (9)	0.0325 (4)
C12	0.31718 (17)	0.72197 (14)	−0.00447 (9)	0.0350 (4)
C13	0.25607 (17)	0.74691 (14)	0.06150 (9)	0.0353 (4)
H13	0.2602	0.8131	0.0799	0.042*
C14	0.1625 (2)	0.37839 (17)	0.00545 (15)	0.0598 (6)
H14A	0.2030	0.3629	0.0536	0.090*
H14B	0.1619	0.3187	−0.0257	0.090*
H14C	0.0753	0.4003	0.0122	0.090*
C15	0.4678 (2)	0.53350 (17)	−0.09913 (13)	0.0563 (6)
H15A	0.4380	0.4697	−0.0800	0.084*
H15B	0.5378	0.5583	−0.0671	0.084*
H15C	0.4972	0.5241	−0.1492	0.084*
C16	0.3895 (3)	0.89192 (19)	−0.02347 (16)	0.0814 (9)
H16A	0.4118	0.8973	0.0293	0.122*
H16B	0.3053	0.9206	−0.0335	0.122*
H16C	0.4518	0.9282	−0.0517	0.122*
O1	0.53629 (11)	0.41127 (10)	0.28772 (7)	0.0349 (3)
O2	0.61499 (14)	0.44439 (13)	0.40353 (7)	0.0543 (4)
C17	0.82803 (18)	0.30408 (16)	0.38428 (12)	0.0441 (5)
H17	0.8410	0.3350	0.4310	0.053*
C18	0.90718 (19)	0.22895 (16)	0.35336 (15)	0.0548 (6)
H18	0.9819	0.2019	0.3762	0.066*
C19	0.8540 (2)	0.20179 (15)	0.28207 (16)	0.0561 (6)
H19	0.8871	0.1533	0.2500	0.067*
C20	0.74153 (17)	0.26098 (14)	0.26751 (13)	0.0432 (5)
H20	0.6885	0.2587	0.2241	0.052*
C21	0.72409 (16)	0.32428 (13)	0.33097 (10)	0.0335 (4)
C22A	0.8799 (6)	0.4776 (5)	0.2125 (4)	0.0428 (13)	0.573 (10)
H22A	0.8044	0.5047	0.1907	0.051*	0.573 (10)
C23A	0.9390 (10)	0.5058 (7)	0.2822 (4)	0.0475 (17)	0.573 (10)
H23A	0.9081	0.5543	0.3150	0.057*	0.573 (10)
C24A	1.0509 (9)	0.4492 (9)	0.2935 (6)	0.061 (2)	0.573 (10)
H24A	1.1078	0.4536	0.3352	0.073*	0.573 (10)
C25A	1.0639 (7)	0.3851 (6)	0.2325 (6)	0.066 (2)	0.573 (10)
H25A	1.1315	0.3398	0.2261	0.079*	0.573 (10)
C26A	0.9571 (9)	0.4001 (5)	0.1817 (4)	0.0557 (17)	0.573 (10)
H26A	0.9407	0.3657	0.1366	0.067*	0.573 (10)
C22B	0.9161 (11)	0.5008 (10)	0.2590 (8)	0.054 (3)	0.427 (10)
H22B	0.8580	0.5522	0.2698	0.065*	0.427 (10)
C23B	1.0227 (13)	0.4685 (10)	0.3061 (8)	0.042 (2)	0.427 (10)
H23B	1.0457	0.4939	0.3536	0.050*	0.427 (10)
C24B	1.0868 (7)	0.3911 (6)	0.2677 (5)	0.0390 (16)	0.427 (10)
H24B	1.1619	0.3584	0.2850	0.047*	0.427 (10)
C25B	1.0200 (10)	0.3709 (9)	0.1994 (5)	0.053 (2)	0.427 (10)
H25B	1.0398	0.3214	0.1643	0.063*	0.427 (10)
C26B	0.9146 (9)	0.4420 (10)	0.1944 (5)	0.058 (2)	0.427 (10)
H26B	0.8549	0.4476	0.1541	0.070*	0.427 (10)
C27	0.61875 (16)	0.39922 (14)	0.34184 (10)	0.0322 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.02669 (13)	0.03286 (14)	0.04103 (15)	−0.00177 (10)	0.00363 (10)	0.00341 (11)
O10	0.0730 (10)	0.0394 (7)	0.0398 (7)	−0.0100 (7)	0.0163 (7)	−0.0081 (6)
O11	0.0554 (8)	0.0485 (8)	0.0222 (6)	0.0097 (6)	0.0121 (5)	0.0010 (5)
O12	0.0776 (10)	0.0441 (8)	0.0441 (8)	−0.0137 (7)	0.0312 (7)	−0.0015 (6)
N1	0.0297 (7)	0.0378 (8)	0.0272 (7)	0.0090 (6)	0.0036 (5)	−0.0010 (6)
N2	0.0559 (11)	0.0769 (13)	0.0246 (8)	0.0280 (10)	−0.0012 (7)	−0.0003 (8)
N3	0.0343 (7)	0.0418 (8)	0.0235 (7)	0.0059 (6)	0.0033 (6)	−0.0031 (6)
N4	0.0391 (8)	0.0469 (9)	0.0259 (7)	0.0139 (7)	0.0085 (6)	−0.0018 (7)
C2	0.0328 (8)	0.0384 (9)	0.0257 (8)	0.0019 (7)	0.0017 (6)	−0.0005 (7)
C4	0.0260 (8)	0.0305 (8)	0.0251 (7)	−0.0022 (6)	0.0048 (6)	−0.0025 (6)
C5	0.0259 (7)	0.0306 (8)	0.0227 (7)	−0.0002 (6)	0.0063 (6)	−0.0001 (6)
C6	0.0300 (8)	0.0368 (9)	0.0227 (7)	0.0021 (7)	0.0059 (6)	−0.0019 (7)
C7	0.0318 (8)	0.0445 (10)	0.0240 (8)	0.0095 (7)	0.0062 (6)	0.0015 (7)
C8	0.0296 (8)	0.0403 (9)	0.0210 (7)	0.0073 (7)	0.0029 (6)	0.0020 (7)
C9	0.0358 (9)	0.0402 (9)	0.0258 (8)	−0.0009 (8)	0.0058 (7)	0.0043 (7)
C10	0.0390 (9)	0.0357 (9)	0.0259 (8)	0.0015 (7)	0.0007 (7)	−0.0012 (7)
C11	0.0375 (9)	0.0408 (9)	0.0195 (7)	0.0041 (7)	0.0050 (6)	0.0006 (7)
C12	0.0386 (9)	0.0399 (10)	0.0271 (8)	−0.0006 (8)	0.0080 (7)	0.0033 (7)
C13	0.0440 (10)	0.0356 (9)	0.0267 (8)	0.0022 (8)	0.0073 (7)	−0.0029 (7)
C14	0.0697 (15)	0.0401 (11)	0.0708 (16)	−0.0098 (11)	0.0187 (12)	−0.0080 (11)
C15	0.0716 (15)	0.0512 (12)	0.0484 (12)	0.0195 (11)	0.0299 (11)	0.0090 (10)
C16	0.130 (3)	0.0467 (14)	0.0704 (17)	−0.0218 (16)	0.0438 (17)	0.0007 (13)
O1	0.0326 (6)	0.0411 (7)	0.0309 (6)	0.0066 (5)	−0.0012 (5)	−0.0018 (5)
O2	0.0486 (8)	0.0816 (11)	0.0323 (7)	0.0195 (8)	−0.0019 (6)	−0.0120 (7)
C17	0.0344 (9)	0.0498 (12)	0.0481 (11)	−0.0014 (8)	0.0008 (8)	0.0203 (9)
C18	0.0337 (10)	0.0407 (11)	0.0898 (17)	0.0036 (9)	−0.0010 (10)	0.0248 (11)
C19	0.0365 (10)	0.0307 (10)	0.1015 (19)	0.0018 (8)	0.0080 (11)	−0.0077 (11)
C20	0.0292 (9)	0.0335 (9)	0.0668 (13)	−0.0025 (7)	0.0019 (8)	−0.0084 (9)
C21	0.0268 (8)	0.0327 (9)	0.0412 (9)	−0.0019 (7)	0.0027 (7)	0.0083 (7)
C22A	0.044 (3)	0.040 (3)	0.044 (3)	0.0012 (19)	0.004 (2)	0.011 (2)
C23A	0.063 (4)	0.036 (2)	0.043 (3)	−0.018 (3)	−0.003 (2)	0.008 (2)
C24A	0.040 (4)	0.064 (6)	0.078 (5)	−0.018 (3)	−0.003 (3)	0.024 (4)
C25A	0.039 (4)	0.072 (4)	0.088 (6)	0.004 (3)	0.021 (4)	0.026 (4)
C26A	0.067 (5)	0.054 (3)	0.048 (3)	0.008 (3)	0.022 (3)	0.005 (2)
C22B	0.039 (4)	0.047 (5)	0.075 (7)	0.004 (3)	−0.001 (4)	0.026 (5)
C23B	0.036 (5)	0.035 (3)	0.055 (4)	−0.008 (3)	0.013 (3)	−0.002 (3)
C24B	0.029 (3)	0.046 (3)	0.043 (4)	−0.004 (2)	0.006 (3)	0.004 (3)
C25B	0.044 (5)	0.076 (5)	0.039 (4)	−0.015 (4)	0.012 (3)	−0.003 (3)
C26B	0.047 (5)	0.075 (7)	0.052 (5)	−0.007 (4)	−0.005 (4)	0.028 (4)
C27	0.0288 (8)	0.0376 (9)	0.0306 (8)	−0.0008 (7)	0.0051 (6)	0.0037 (7)

Geometric parameters (Å, º) top

Fe1—C26B	1.996 (7)	C13—H13	0.9300
Fe1—C22B	2.009 (13)	C14—H14A	0.9600
Fe1—C25B	2.023 (7)	C14—H14B	0.9600
Fe1—C23B	2.027 (14)	C14—H14C	0.9600
Fe1—C20	2.0277 (18)	C15—H15A	0.9600
Fe1—C25A	2.031 (6)	C15—H15B	0.9600
Fe1—C19	2.033 (2)	C15—H15C	0.9600
Fe1—C24A	2.035 (11)	C16—H16A	0.9600
Fe1—C18	2.037 (2)	C16—H16B	0.9600
Fe1—C21	2.0430 (17)	C16—H16C	0.9600
Fe1—C26A	2.045 (6)	O1—C27	1.271 (2)
Fe1—C17	2.046 (2)	O2—C27	1.249 (2)
O10—C10	1.365 (2)	C17—C18	1.409 (3)
O10—C14	1.420 (3)	C17—C21	1.430 (2)
O11—C11	1.376 (2)	C17—H17	0.9300
O11—C15	1.415 (2)	C18—C19	1.407 (3)
O12—C12	1.369 (2)	C18—H18	0.9300
O12—C16	1.411 (3)	C19—C20	1.416 (3)
N1—C2	1.352 (2)	C19—H19	0.9300
N1—C6	1.360 (2)	C20—C21	1.419 (3)
N1—H1	0.858 (15)	C20—H20	0.9300
N2—C2	1.328 (2)	C21—C27	1.488 (2)
N2—H2A	0.853 (13)	C22A—C23A	1.409 (7)
N2—H2B	0.88 (3)	C22A—C26A	1.418 (7)
N3—C2	1.334 (2)	C22A—H22A	0.9300
N3—C4	1.343 (2)	C23A—C24A	1.385 (11)
N4—C4	1.325 (2)	C23A—H23A	0.9300
N4—H4A	0.850 (12)	C24A—C25A	1.384 (11)
N4—H4B	0.89 (2)	C24A—H24A	0.9300
C4—C5	1.439 (2)	C25A—C26A	1.413 (9)
C5—C6	1.343 (2)	C25A—H25A	0.9300
C5—C7	1.513 (2)	C26A—H26A	0.9300
C6—H6	0.9300	C22B—C26B	1.385 (13)
C7—C8	1.514 (2)	C22B—C23B	1.423 (15)
C7—H7A	0.9700	C22B—H22B	0.9300
C7—H7B	0.9700	C23B—C24B	1.407 (10)
C8—C13	1.382 (2)	C23B—H23B	0.9300
C8—C9	1.391 (2)	C24B—C25B	1.397 (9)
C9—C10	1.392 (2)	C24B—H24B	0.9300
C9—H9	0.9300	C25B—C26B	1.437 (12)
C10—C11	1.398 (2)	C25B—H25B	0.9300
C11—C12	1.388 (3)	C26B—H26B	0.9300
C12—C13	1.394 (2)

C26B—Fe1—C22B	40.4 (4)	H14A—C14—H14C	109.5
C26B—Fe1—C25B	41.9 (3)	H14B—C14—H14C	109.5
C22B—Fe1—C25B	69.5 (4)	O11—C15—H15A	109.5
C26B—Fe1—C23B	68.6 (5)	O11—C15—H15B	109.5
C22B—Fe1—C23B	41.3 (4)	H15A—C15—H15B	109.5
C25B—Fe1—C23B	68.8 (4)	O11—C15—H15C	109.5
C26B—Fe1—C20	109.1 (2)	H15A—C15—H15C	109.5
C22B—Fe1—C20	128.7 (3)	H15B—C15—H15C	109.5
C25B—Fe1—C20	118.7 (2)	O12—C16—H16A	109.5
C23B—Fe1—C20	166.9 (3)	O12—C16—H16B	109.5
C20—Fe1—C25A	138.1 (3)	H16A—C16—H16B	109.5
C26B—Fe1—C19	125.8 (4)	O12—C16—H16C	109.5
C22B—Fe1—C19	164.5 (4)	H16A—C16—H16C	109.5
C25B—Fe1—C19	104.3 (3)	H16B—C16—H16C	109.5
C23B—Fe1—C19	151.1 (4)	C18—C17—C21	107.82 (19)
C20—Fe1—C19	40.83 (8)	C18—C17—Fe1	69.46 (12)
C25A—Fe1—C19	112.8 (2)	C21—C17—Fe1	69.42 (11)
C20—Fe1—C24A	175.8 (3)	C18—C17—H17	126.1
C25A—Fe1—C24A	39.8 (3)	C21—C17—H17	126.1
C19—Fe1—C24A	141.4 (3)	Fe1—C17—H17	126.6
C26B—Fe1—C18	161.4 (5)	C19—C18—C17	108.43 (18)
C22B—Fe1—C18	154.8 (4)	C19—C18—Fe1	69.61 (13)
C25B—Fe1—C18	121.8 (4)	C17—C18—Fe1	70.17 (11)
C23B—Fe1—C18	117.9 (4)	C19—C18—H18	125.8
C20—Fe1—C18	68.55 (9)	C17—C18—H18	125.8
C25A—Fe1—C18	114.7 (2)	Fe1—C18—H18	126.0
C19—Fe1—C18	40.46 (10)	C18—C19—C20	108.34 (19)
C24A—Fe1—C18	115.4 (3)	C18—C19—Fe1	69.93 (12)
C26B—Fe1—C21	122.7 (3)	C20—C19—Fe1	69.40 (11)
C22B—Fe1—C21	111.2 (3)	C18—C19—H19	125.8
C25B—Fe1—C21	155.8 (3)	C20—C19—H19	125.8
C23B—Fe1—C21	128.7 (3)	Fe1—C19—H19	126.4
C20—Fe1—C21	40.79 (8)	C19—C20—C21	107.86 (19)
C25A—Fe1—C21	176.5 (3)	C19—C20—Fe1	69.77 (11)
C19—Fe1—C21	68.42 (8)	C21—C20—Fe1	70.18 (10)
C24A—Fe1—C21	141.0 (3)	C19—C20—H20	126.1
C18—Fe1—C21	68.44 (8)	C21—C20—H20	126.1
C20—Fe1—C26A	108.5 (3)	Fe1—C20—H20	125.6
C25A—Fe1—C26A	40.6 (3)	C20—C21—C17	107.54 (17)
C19—Fe1—C26A	110.77 (18)	C20—C21—C27	127.48 (16)
C24A—Fe1—C26A	67.6 (3)	C17—C21—C27	124.98 (17)
C18—Fe1—C26A	140.5 (2)	C20—C21—Fe1	69.03 (10)
C21—Fe1—C26A	136.0 (3)	C17—C21—Fe1	69.63 (10)
C26B—Fe1—C17	157.5 (4)	C27—C21—Fe1	126.39 (12)
C22B—Fe1—C17	122.4 (4)	C23A—C22A—C26A	107.2 (7)
C25B—Fe1—C17	159.6 (4)	C23A—C22A—Fe1	69.2 (4)
C23B—Fe1—C17	108.2 (4)	C26A—C22A—Fe1	68.5 (4)
C20—Fe1—C17	68.69 (9)	C23A—C22A—H22A	126.4
C25A—Fe1—C17	142.5 (3)	C26A—C22A—H22A	126.4
C19—Fe1—C17	68.12 (10)	Fe1—C22A—H22A	127.5
C24A—Fe1—C17	115.1 (3)	C24A—C23A—C22A	108.6 (8)
C18—Fe1—C17	40.37 (9)	C24A—C23A—Fe1	69.3 (6)
C21—Fe1—C17	40.95 (7)	C22A—C23A—Fe1	71.0 (4)
C26A—Fe1—C17	176.9 (3)	C24A—C23A—H23A	125.7
C10—O10—C14	118.44 (15)	C22A—C23A—H23A	125.7
C11—O11—C15	116.28 (14)	Fe1—C23A—H23A	125.5
C12—O12—C16	118.02 (17)	C25A—C24A—C23A	108.6 (8)
C2—N1—C6	119.44 (15)	C25A—C24A—Fe1	70.0 (5)
C2—N1—H1	120.2 (13)	C23A—C24A—Fe1	71.2 (5)
C6—N1—H1	119.6 (13)	C25A—C24A—H24A	125.7
C2—N2—H2A	119.5 (17)	C23A—C24A—H24A	125.7
C2—N2—H2B	118.2 (16)	Fe1—C24A—H24A	124.8
H2A—N2—H2B	120 (2)	C24A—C25A—C26A	108.5 (6)
C2—N3—C4	117.88 (14)	C24A—C25A—Fe1	70.3 (5)
C4—N4—H4A	118.5 (14)	C26A—C25A—Fe1	70.3 (3)
C4—N4—H4B	123.3 (14)	C24A—C25A—H25A	125.7
H4A—N4—H4B	118 (2)	C26A—C25A—H25A	125.7
N2—C2—N3	120.34 (16)	Fe1—C25A—H25A	125.3
N2—C2—N1	117.16 (16)	C25A—C26A—C22A	107.0 (6)
N3—C2—N1	122.50 (15)	C25A—C26A—Fe1	69.2 (4)
N4—C4—N3	117.10 (14)	C22A—C26A—Fe1	71.3 (4)
N4—C4—C5	120.34 (15)	C25A—C26A—H26A	126.5
N3—C4—C5	122.56 (15)	C22A—C26A—H26A	126.5
C6—C5—C4	115.37 (14)	Fe1—C26A—H26A	124.6
C6—C5—C7	124.36 (14)	C26B—C22B—C23B	107.7 (9)
C4—C5—C7	120.09 (14)	C26B—C22B—Fe1	69.3 (6)
C5—C6—N1	122.24 (15)	C23B—C22B—Fe1	70.0 (7)
C5—C6—H6	118.9	C26B—C22B—H22B	126.1
N1—C6—H6	118.9	C23B—C22B—H22B	126.1
C5—C7—C8	114.11 (13)	Fe1—C22B—H22B	126.1
C5—C7—H7A	108.7	C24B—C23B—C22B	107.5 (11)
C8—C7—H7A	108.7	C24B—C23B—Fe1	71.0 (6)
C5—C7—H7B	108.7	C22B—C23B—Fe1	68.7 (7)
C8—C7—H7B	108.7	C24B—C23B—H23B	126.3
H7A—C7—H7B	107.6	C22B—C23B—H23B	126.3
C13—C8—C9	120.17 (15)	Fe1—C23B—H23B	125.6
C13—C8—C7	119.28 (16)	C25B—C24B—C23B	109.4 (10)
C9—C8—C7	120.53 (16)	C25B—C24B—Fe1	68.7 (5)
C8—C9—C10	119.89 (16)	C23B—C24B—Fe1	68.7 (7)
C8—C9—H9	120.1	C25B—C24B—H24B	125.3
C10—C9—H9	120.1	C23B—C24B—H24B	125.3
O10—C10—C9	124.66 (16)	Fe1—C24B—H24B	128.9
O10—C10—C11	115.22 (15)	C24B—C25B—C26B	106.2 (8)
C9—C10—C11	120.12 (16)	C24B—C25B—Fe1	71.3 (5)
O11—C11—C12	117.85 (16)	C26B—C25B—Fe1	68.1 (4)
O11—C11—C10	122.56 (16)	C24B—C25B—H25B	126.9
C12—C11—C10	119.39 (15)	C26B—C25B—H25B	126.9
O12—C12—C11	115.16 (15)	Fe1—C25B—H25B	125.4
O12—C12—C13	124.45 (17)	C22B—C26B—C25B	109.1 (7)
C11—C12—C13	120.38 (16)	C22B—C26B—Fe1	70.3 (6)
C8—C13—C12	119.98 (17)	C25B—C26B—Fe1	70.1 (4)
C8—C13—H13	120.0	C22B—C26B—H26B	125.5
C12—C13—H13	120.0	C25B—C26B—H26B	125.5
O10—C14—H14A	109.5	Fe1—C26B—H26B	125.8
O10—C14—H14B	109.5	O2—C27—O1	124.18 (16)
H14A—C14—H14B	109.5	O2—C27—C21	118.51 (15)
O10—C14—H14C	109.5	O1—C27—C21	117.29 (15)

C4—N3—C2—N2	−179.46 (18)	C18—C19—C20—Fe1	59.28 (15)
C4—N3—C2—N1	−0.6 (3)	C19—C20—C21—C17	0.7 (2)
C6—N1—C2—N2	178.51 (18)	Fe1—C20—C21—C17	−59.20 (13)
C6—N1—C2—N3	−0.3 (3)	C19—C20—C21—C27	−179.70 (17)
C2—N3—C4—N4	−179.78 (16)	Fe1—C20—C21—C27	120.45 (18)
C2—N3—C4—C5	1.1 (2)	C19—C20—C21—Fe1	59.85 (14)
N4—C4—C5—C6	−179.61 (16)	C18—C17—C21—C20	−0.2 (2)
N3—C4—C5—C6	−0.5 (2)	Fe1—C17—C21—C20	58.82 (13)
N4—C4—C5—C7	−4.2 (2)	C18—C17—C21—C27	−179.89 (16)
N3—C4—C5—C7	174.97 (16)	Fe1—C17—C21—C27	−120.84 (17)
C4—C5—C6—N1	−0.6 (2)	C18—C17—C21—Fe1	−59.05 (13)
C7—C5—C6—N1	−175.78 (16)	C26A—C22A—C23A—C24A	1.2 (9)
C2—N1—C6—C5	1.0 (3)	Fe1—C22A—C23A—C24A	59.3 (6)
C6—C5—C7—C8	−10.9 (3)	C26A—C22A—C23A—Fe1	−58.1 (4)
C4—C5—C7—C8	174.13 (15)	C22A—C23A—C24A—C25A	−0.2 (10)
C5—C7—C8—C13	−102.38 (19)	Fe1—C23A—C24A—C25A	60.2 (6)
C5—C7—C8—C9	76.4 (2)	C22A—C23A—C24A—Fe1	−60.4 (5)
C13—C8—C9—C10	0.5 (3)	C23A—C24A—C25A—C26A	−0.9 (10)
C7—C8—C9—C10	−178.22 (15)	Fe1—C24A—C25A—C26A	60.1 (5)
C14—O10—C10—C9	−0.4 (3)	C23A—C24A—C25A—Fe1	−60.9 (6)
C14—O10—C10—C11	179.23 (18)	C24A—C25A—C26A—C22A	1.6 (8)
C8—C9—C10—O10	−178.51 (16)	Fe1—C25A—C26A—C22A	61.7 (4)
C8—C9—C10—C11	1.8 (3)	C24A—C25A—C26A—Fe1	−60.1 (6)
C15—O11—C11—C12	118.0 (2)	C23A—C22A—C26A—C25A	−1.7 (7)
C15—O11—C11—C10	−67.2 (2)	Fe1—C22A—C26A—C25A	−60.3 (4)
O10—C10—C11—O11	2.9 (2)	C23A—C22A—C26A—Fe1	58.5 (5)
C9—C10—C11—O11	−177.43 (16)	C26B—C22B—C23B—C24B	1.4 (13)
O10—C10—C11—C12	177.59 (16)	Fe1—C22B—C23B—C24B	60.7 (8)
C9—C10—C11—C12	−2.7 (3)	C26B—C22B—C23B—Fe1	−59.3 (7)
C16—O12—C12—C11	173.6 (2)	C22B—C23B—C24B—C25B	−2.6 (12)
C16—O12—C12—C13	−7.4 (3)	Fe1—C23B—C24B—C25B	56.6 (7)
O11—C11—C12—O12	−4.7 (2)	C22B—C23B—C24B—Fe1	−59.2 (8)
C10—C11—C12—O12	−179.66 (17)	C23B—C24B—C25B—C26B	2.8 (10)
O11—C11—C12—C13	176.24 (16)	Fe1—C24B—C25B—C26B	59.4 (5)
C10—C11—C12—C13	1.3 (3)	C23B—C24B—C25B—Fe1	−56.6 (8)
C9—C8—C13—C12	−2.0 (3)	C23B—C22B—C26B—C25B	0.2 (12)
C7—C8—C13—C12	176.80 (15)	Fe1—C22B—C26B—C25B	−59.5 (6)
O12—C12—C13—C8	−177.92 (17)	C23B—C22B—C26B—Fe1	59.7 (8)
C11—C12—C13—C8	1.0 (3)	C24B—C25B—C26B—C22B	−1.8 (10)
C21—C17—C18—C19	−0.3 (2)	Fe1—C25B—C26B—C22B	59.6 (7)
Fe1—C17—C18—C19	−59.30 (15)	C24B—C25B—C26B—Fe1	−61.5 (6)
C21—C17—C18—Fe1	59.02 (13)	C20—C21—C27—O2	176.03 (19)
C17—C18—C19—C20	0.7 (2)	C17—C21—C27—O2	−4.4 (3)
Fe1—C18—C19—C20	−58.95 (15)	Fe1—C21—C27—O2	−93.7 (2)
C17—C18—C19—Fe1	59.64 (14)	C20—C21—C27—O1	−2.4 (3)
C18—C19—C20—C21	−0.8 (2)	C17—C21—C27—O1	177.17 (16)
Fe1—C19—C20—C21	−60.11 (13)	Fe1—C21—C27—O1	87.86 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86 (2)	1.82 (2)	2.673 (2)	176 (2)
N2—H2A···O2ⁱ	0.85 (2)	2.15 (2)	2.905 (2)	148 (2)
N2—H2B···O2	0.88 (2)	1.97 (2)	2.846 (3)	172 (2)
N4—H4A···O11ⁱⁱ	0.85 (2)	2.58 (2)	3.137 (2)	124 (2)
N4—H4A···O12ⁱⁱ	0.85 (2)	2.35 (2)	3.092 (2)	146 (2)
N4—H4B···O1ⁱⁱⁱ	0.89 (2)	2.19 (2)	3.032 (2)	159.3 (18)
C7—H7A···O1ⁱⁱⁱ	0.97	2.54	3.349 (2)	141

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

4-Amino-5-chloro-2,6-dimethylpyrimidine–ferrocene-1-carboxylic acid (1/1) (II) top

Crystal data top

[Fe(C₅H₅)(C₆H₅O₂)]·C₆H₈ClN₃	F(000) = 1600
M_r = 387.64	D_x = 1.508 Mg m⁻³
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 20.8783 (7) Å	Cell parameters from 7025 reflections
b = 7.4013 (2) Å	θ = 2.9–28.0°
c = 23.2605 (8) Å	µ = 1.05 mm⁻¹
β = 108.146 (4)°	T = 293 K
V = 3415.6 (2) Å³	Prism, orange
Z = 8	0.50 × 0.50 × 0.30 mm

Data collection top

Agilent SuperNova Dual Source diffractometer with an Atlas detector	3927 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3201 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4933 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ω scans	h = −27→27
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −9→9
T_min = 0.840, T_max = 1.000	l = −28→30
16278 measured reflections

Refinement top

Refinement on F²	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.036P)² + 2.0431P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.002
3927 reflections	Δρ_max = 0.29 e Å⁻³
228 parameters	Δρ_min = −0.32 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	0.61085 (2)	0.16262 (4)	0.45770 (2)	0.03673 (10)
Cl1	0.19629 (3)	0.22306 (9)	0.12622 (2)	0.06016 (17)
N1	0.37720 (8)	0.3149 (2)	0.24276 (7)	0.0459 (4)
H4A	0.1965 (11)	0.6788 (19)	0.2078 (9)	0.055*
H4B	0.1606 (7)	0.523 (3)	0.1710 (9)	0.055*
N3	0.30822 (7)	0.5651 (2)	0.24712 (7)	0.0389 (4)
N4	0.19707 (8)	0.5764 (3)	0.19025 (9)	0.0511 (4)
C2	0.36629 (9)	0.4749 (3)	0.26381 (8)	0.0417 (4)
C4	0.25552 (9)	0.4869 (3)	0.20593 (8)	0.0374 (4)
C5	0.26386 (10)	0.3185 (3)	0.18129 (8)	0.0402 (4)
C6	0.32505 (11)	0.2356 (3)	0.20013 (8)	0.0447 (5)
C7	0.42403 (10)	0.5619 (4)	0.31091 (11)	0.0605 (6)
H7A	0.4656	0.5076	0.3102	0.091*
H7B	0.4187	0.5450	0.3501	0.091*
H7C	0.4248	0.6887	0.3026	0.091*
C8	0.33960 (14)	0.0581 (4)	0.17576 (12)	0.0708 (7)
H8A	0.3841	0.0187	0.1985	0.106*
H8B	0.3368	0.0719	0.1340	0.106*
H8C	0.3073	−0.0300	0.1792	0.106*
O1	0.49744 (8)	0.1712 (2)	0.29745 (7)	0.0620 (5)
H1	0.4582 (15)	0.206 (4)	0.2805 (14)	0.093*
O2	0.44799 (7)	0.0097 (2)	0.35270 (8)	0.0679 (5)
C20	0.62777 (9)	0.0999 (3)	0.37852 (9)	0.0422 (4)
H20	0.6319	0.1819	0.3496	0.051*
C19	0.68095 (10)	0.0318 (3)	0.42753 (10)	0.0486 (5)
H19	0.7263	0.0613	0.4364	0.058*
C18	0.65368 (10)	−0.0882 (3)	0.46072 (10)	0.0505 (5)
H18	0.6778	−0.1512	0.4953	0.061*
C17	0.58328 (10)	−0.0961 (3)	0.43225 (10)	0.0480 (5)
H17	0.5530	−0.1657	0.4447	0.058*
C21	0.56683 (9)	0.0204 (3)	0.38139 (9)	0.0390 (4)
C24	0.57882 (15)	0.2283 (4)	0.52958 (12)	0.0736 (8)
H24	0.5645	0.1469	0.5535	0.088*
C23	0.53825 (13)	0.3130 (4)	0.47643 (13)	0.0711 (8)
H23	0.4920	0.2977	0.4592	0.085*
C22	0.57878 (16)	0.4231 (3)	0.45397 (12)	0.0707 (7)
H22	0.5645	0.4934	0.4192	0.085*
C26	0.64452 (16)	0.4097 (4)	0.49270 (14)	0.0757 (8)
H26	0.6818	0.4698	0.4883	0.091*
C25	0.64479 (14)	0.2899 (4)	0.53952 (11)	0.0744 (8)
H25	0.6823	0.2571	0.5716	0.089*
C27	0.49805 (10)	0.0650 (3)	0.34262 (9)	0.0454 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.03878 (15)	0.03346 (15)	0.03900 (16)	0.00127 (11)	0.01363 (11)	−0.00112 (11)
Cl1	0.0653 (3)	0.0600 (4)	0.0477 (3)	−0.0124 (3)	0.0068 (2)	−0.0110 (3)
N1	0.0488 (9)	0.0473 (10)	0.0393 (8)	0.0156 (8)	0.0101 (7)	0.0013 (7)
N3	0.0372 (8)	0.0378 (9)	0.0392 (8)	0.0044 (7)	0.0083 (6)	−0.0006 (7)
N4	0.0358 (8)	0.0464 (11)	0.0614 (11)	0.0028 (8)	0.0012 (8)	−0.0069 (9)
C2	0.0396 (9)	0.0457 (11)	0.0382 (9)	0.0076 (9)	0.0098 (8)	0.0034 (9)
C4	0.0389 (9)	0.0376 (10)	0.0343 (9)	0.0012 (8)	0.0096 (7)	0.0055 (8)
C5	0.0484 (10)	0.0395 (10)	0.0311 (9)	−0.0020 (9)	0.0103 (8)	0.0017 (8)
C6	0.0619 (12)	0.0403 (11)	0.0342 (9)	0.0086 (10)	0.0181 (9)	0.0024 (8)
C7	0.0444 (11)	0.0645 (15)	0.0619 (13)	0.0065 (11)	0.0008 (10)	−0.0132 (12)
C8	0.0909 (18)	0.0596 (16)	0.0616 (14)	0.0218 (14)	0.0231 (13)	−0.0142 (12)
O1	0.0522 (9)	0.0751 (12)	0.0568 (9)	0.0240 (9)	0.0142 (8)	0.0143 (8)
O2	0.0364 (7)	0.0676 (11)	0.0881 (12)	−0.0091 (8)	0.0026 (8)	0.0116 (9)
C20	0.0451 (10)	0.0420 (10)	0.0434 (10)	0.0017 (9)	0.0194 (8)	−0.0037 (9)
C19	0.0348 (9)	0.0526 (13)	0.0579 (12)	0.0036 (9)	0.0137 (9)	−0.0077 (10)
C18	0.0463 (11)	0.0406 (11)	0.0572 (12)	0.0114 (10)	0.0054 (9)	0.0050 (10)
C17	0.0450 (10)	0.0305 (10)	0.0655 (13)	−0.0013 (9)	0.0128 (10)	0.0053 (9)
C21	0.0367 (9)	0.0303 (9)	0.0473 (10)	0.0020 (8)	0.0092 (8)	−0.0055 (8)
C24	0.094 (2)	0.0814 (19)	0.0604 (15)	0.0179 (17)	0.0455 (15)	−0.0009 (14)
C23	0.0608 (14)	0.0794 (19)	0.0742 (17)	0.0231 (14)	0.0225 (13)	−0.0206 (15)
C22	0.104 (2)	0.0408 (13)	0.0637 (15)	0.0191 (14)	0.0212 (15)	−0.0074 (12)
C26	0.093 (2)	0.0534 (15)	0.0851 (19)	−0.0194 (15)	0.0338 (17)	−0.0303 (15)
C25	0.0762 (17)	0.083 (2)	0.0519 (14)	0.0200 (15)	0.0023 (12)	−0.0257 (14)
C27	0.0412 (10)	0.0359 (11)	0.0528 (12)	0.0036 (9)	0.0053 (9)	−0.0084 (9)

Geometric parameters (Å, º) top

Fe1—C21	2.0215 (18)	C8—H8B	0.9600
Fe1—C22	2.034 (2)	C8—H8C	0.9600
Fe1—C17	2.034 (2)	O1—C27	1.309 (3)
Fe1—C23	2.034 (2)	O1—H1	0.83 (3)
Fe1—C20	2.0342 (19)	O2—C27	1.211 (2)
Fe1—C26	2.036 (3)	C20—C19	1.413 (3)
Fe1—C25	2.042 (2)	C20—C21	1.422 (3)
Fe1—C24	2.043 (2)	C20—H20	0.9300
Fe1—C18	2.052 (2)	C19—C18	1.408 (3)
Fe1—C19	2.052 (2)	C19—H19	0.9300
Cl1—C5	1.7334 (19)	C18—C17	1.413 (3)
N1—C2	1.328 (3)	C18—H18	0.9300
N1—C6	1.357 (3)	C17—C21	1.417 (3)
N3—C2	1.332 (2)	C17—H17	0.9300
N3—C4	1.344 (2)	C21—C27	1.476 (3)
N4—C4	1.336 (2)	C24—C25	1.400 (4)
N4—H4A	0.862 (9)	C24—C23	1.410 (4)
N4—H4B	0.852 (9)	C24—H24	0.9300
C2—C7	1.498 (3)	C23—C22	1.389 (4)
C4—C5	1.405 (3)	C23—H23	0.9300
C5—C6	1.361 (3)	C22—C26	1.391 (4)
C6—C8	1.499 (3)	C22—H22	0.9300
C7—H7A	0.9600	C26—C25	1.403 (4)
C7—H7B	0.9600	C26—H26	0.9300
C7—H7C	0.9600	C25—H25	0.9300
C8—H8A	0.9600

C21—Fe1—C22	113.73 (9)	C6—C8—H8B	109.5
C21—Fe1—C17	40.91 (8)	H8A—C8—H8B	109.5
C22—Fe1—C17	145.14 (11)	C6—C8—H8C	109.5
C21—Fe1—C23	107.91 (9)	H8A—C8—H8C	109.5
C22—Fe1—C23	39.92 (11)	H8B—C8—H8C	109.5
C17—Fe1—C23	114.54 (11)	C27—O1—H1	109 (2)
C21—Fe1—C20	41.05 (8)	C19—C20—C21	107.72 (18)
C22—Fe1—C20	108.99 (10)	C19—C20—Fe1	70.45 (11)
C17—Fe1—C20	68.58 (9)	C21—C20—Fe1	68.99 (11)
C23—Fe1—C20	132.07 (10)	C19—C20—H20	126.1
C21—Fe1—C26	145.55 (11)	C21—C20—H20	126.1
C22—Fe1—C26	39.98 (11)	Fe1—C20—H20	126.0
C17—Fe1—C26	173.37 (11)	C18—C19—C20	108.47 (17)
C23—Fe1—C26	67.07 (12)	C18—C19—Fe1	69.93 (12)
C20—Fe1—C26	115.55 (11)	C20—C19—Fe1	69.08 (11)
C21—Fe1—C25	171.57 (11)	C18—C19—H19	125.8
C22—Fe1—C25	67.46 (11)	C20—C19—H19	125.8
C17—Fe1—C25	133.63 (11)	Fe1—C19—H19	126.8
C23—Fe1—C25	67.27 (11)	C19—C18—C17	107.97 (18)
C20—Fe1—C25	147.28 (11)	C19—C18—Fe1	69.94 (12)
C26—Fe1—C25	40.25 (12)	C17—C18—Fe1	69.06 (11)
C21—Fe1—C24	131.84 (11)	C19—C18—H18	126.0
C22—Fe1—C24	67.81 (12)	C17—C18—H18	126.0
C17—Fe1—C24	109.09 (11)	Fe1—C18—H18	126.6
C23—Fe1—C24	40.45 (11)	C18—C17—C21	108.20 (18)
C20—Fe1—C24	171.32 (10)	C18—C17—Fe1	70.48 (12)
C26—Fe1—C24	67.63 (12)	C21—C17—Fe1	69.09 (11)
C25—Fe1—C24	40.08 (11)	C18—C17—H17	125.9
C21—Fe1—C18	68.49 (8)	C21—C17—H17	125.9
C22—Fe1—C18	173.25 (11)	Fe1—C17—H17	126.1
C17—Fe1—C18	40.46 (8)	C17—C21—C20	107.64 (16)
C23—Fe1—C18	146.46 (11)	C17—C21—C27	125.65 (18)
C20—Fe1—C18	68.14 (9)	C20—C21—C27	126.42 (19)
C26—Fe1—C18	134.93 (11)	C17—C21—Fe1	70.01 (11)
C25—Fe1—C18	111.36 (10)	C20—C21—Fe1	69.96 (10)
C24—Fe1—C18	115.93 (11)	C27—C21—Fe1	120.68 (13)
C21—Fe1—C19	68.40 (8)	C25—C24—C23	106.9 (3)
C22—Fe1—C19	133.86 (11)	C25—C24—Fe1	69.93 (14)
C17—Fe1—C19	67.90 (9)	C23—C24—Fe1	69.42 (14)
C23—Fe1—C19	171.79 (11)	C25—C24—H24	126.5
C20—Fe1—C19	40.47 (8)	C23—C24—H24	126.5
C26—Fe1—C19	111.48 (11)	Fe1—C24—H24	125.7
C25—Fe1—C19	117.30 (10)	C22—C23—C24	108.7 (2)
C24—Fe1—C19	147.35 (10)	C22—C23—Fe1	70.02 (14)
C18—Fe1—C19	40.13 (9)	C24—C23—Fe1	70.13 (14)
C2—N1—C6	117.66 (17)	C22—C23—H23	125.6
C2—N3—C4	117.44 (17)	C24—C23—H23	125.6
C4—N4—H4A	116.9 (16)	Fe1—C23—H23	125.8
C4—N4—H4B	120.3 (16)	C23—C22—C26	108.0 (2)
H4A—N4—H4B	121 (2)	C23—C22—Fe1	70.06 (14)
N1—C2—N3	125.78 (18)	C26—C22—Fe1	70.09 (15)
N1—C2—C7	117.46 (17)	C23—C22—H22	126.0
N3—C2—C7	116.76 (18)	C26—C22—H22	126.0
N4—C4—N3	117.16 (18)	Fe1—C22—H22	125.4
N4—C4—C5	123.19 (18)	C22—C26—C25	108.2 (3)
N3—C4—C5	119.65 (17)	C22—C26—Fe1	69.93 (14)
C6—C5—C4	119.46 (18)	C25—C26—Fe1	70.13 (15)
C6—C5—Cl1	121.37 (16)	C22—C26—H26	125.9
C4—C5—Cl1	119.15 (15)	C25—C26—H26	125.9
N1—C6—C5	119.98 (18)	Fe1—C26—H26	125.6
N1—C6—C8	116.38 (19)	C24—C25—C26	108.2 (2)
C5—C6—C8	123.6 (2)	C24—C25—Fe1	70.00 (14)
C2—C7—H7A	109.5	C26—C25—Fe1	69.62 (14)
C2—C7—H7B	109.5	C24—C25—H25	125.9
H7A—C7—H7B	109.5	C26—C25—H25	125.9
C2—C7—H7C	109.5	Fe1—C25—H25	126.0
H7A—C7—H7C	109.5	O2—C27—O1	124.39 (19)
H7B—C7—H7C	109.5	O2—C27—C21	122.7 (2)
C6—C8—H8A	109.5	O1—C27—C21	112.89 (18)

C6—N1—C2—N3	0.5 (3)	Fe1—C17—C21—C27	−114.03 (19)
C6—N1—C2—C7	179.97 (19)	C18—C17—C21—Fe1	−59.85 (15)
C4—N3—C2—N1	0.9 (3)	C19—C20—C21—C17	−0.1 (2)
C4—N3—C2—C7	−178.49 (18)	Fe1—C20—C21—C17	−60.14 (14)
C2—N3—C4—N4	178.73 (18)	C19—C20—C21—C27	174.01 (19)
C2—N3—C4—C5	−1.6 (3)	Fe1—C20—C21—C27	113.94 (19)
N4—C4—C5—C6	−179.46 (19)	C19—C20—C21—Fe1	60.07 (14)
N3—C4—C5—C6	0.9 (3)	C25—C24—C23—C22	0.5 (3)
N4—C4—C5—Cl1	1.9 (3)	Fe1—C24—C23—C22	−59.60 (17)
N3—C4—C5—Cl1	−177.69 (14)	C25—C24—C23—Fe1	60.15 (18)
C2—N1—C6—C5	−1.3 (3)	C24—C23—C22—C26	−0.4 (3)
C2—N1—C6—C8	178.0 (2)	Fe1—C23—C22—C26	−60.10 (17)
C4—C5—C6—N1	0.6 (3)	C24—C23—C22—Fe1	59.67 (18)
Cl1—C5—C6—N1	179.15 (14)	C23—C22—C26—C25	0.1 (3)
C4—C5—C6—C8	−178.6 (2)	Fe1—C22—C26—C25	−59.93 (18)
Cl1—C5—C6—C8	0.0 (3)	C23—C22—C26—Fe1	60.08 (17)
C21—C20—C19—C18	−0.1 (2)	C23—C24—C25—C26	−0.5 (3)
Fe1—C20—C19—C18	59.01 (15)	Fe1—C24—C25—C26	59.37 (18)
C21—C20—C19—Fe1	−59.15 (13)	C23—C24—C25—Fe1	−59.83 (17)
C20—C19—C18—C17	0.3 (2)	C22—C26—C25—C24	0.2 (3)
Fe1—C19—C18—C17	58.78 (15)	Fe1—C26—C25—C24	−59.61 (18)
C20—C19—C18—Fe1	−58.48 (14)	C22—C26—C25—Fe1	59.81 (17)
C19—C18—C17—C21	−0.3 (2)	C17—C21—C27—O2	3.2 (3)
Fe1—C18—C17—C21	58.98 (14)	C20—C21—C27—O2	−169.9 (2)
C19—C18—C17—Fe1	−59.32 (15)	Fe1—C21—C27—O2	−83.2 (2)
C18—C17—C21—C20	0.3 (2)	C17—C21—C27—O1	−177.75 (19)
Fe1—C17—C21—C20	60.11 (13)	C20—C21—C27—O1	9.2 (3)
C18—C17—C21—C27	−173.88 (19)	Fe1—C21—C27—O1	95.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.83 (3)	1.83 (3)	2.658 (2)	172 (3)
N4—H4A···N3ⁱ	0.86 (2)	2.18 (2)	3.046 (3)	178 (2)
N4—H4B···O2ⁱⁱ	0.85 (2)	2.17 (2)	2.948 (2)	151 (2)
C24—H24···O2ⁱⁱⁱ	0.93	2.55	3.445 (3)	160

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

Comparison of the pseudo-torsion angle values for the compounds (I) and (II).
The ring centroids Cg1 and Cg3 correspond to C17-C21 atoms, whereas Cg2, Cg4 and Cg5 correspond to C22–C26 atoms. A and B correspond respectively to major and minor component of the disordered Cp ring of compound (I). top

(I)		(II)
C17—Cg3—Cg4—C24A	36.44	C17—Cg1—Cg2—C24	23.06
C17—Cg3—Cg5—C24B	79.73
C18—Cg3—Cg4—C25A	36.13	C18—Cg3—Cg5—C25B	79.26
C18—Cg1—Cg2—C25	22.86
C19—Cg3—Cg4—C26A	36.88	C19—Cg3—Cg5—C26B	80.94
C19—Cg1—Cg2—C26	23.46
C20—Cg3—Cg4—C22A	37.10	C20—Cg3—Cg5—C22B	79.51
C20–Cg1—Cg2—C22	23.15
C21–Cg3—Cg4—C23A	37.53	C21–Cg3—Cg5—C23B	80.28
C21—Cg1—Cg2—C23	22.58

Details of weak π–π stacking interactions for compounds (I) and (II).
Cg1 is the centroid of the pyrimidine ring of TMP (N1/C2/N3/C4–C6) and Cg4 is the centroid of the unsubstituted Cp ring (C22–C26) in compound (I), and Cg3 is the centroid of the pyrimidine ring (N1/C2/N3/C4–C6) and Cg1 is the centroid of the substituted Cp ring (C17–C21) in compound (II). Cg···Cg is the perpendicular distance between the first ring centroid and that of the second ring. α is the dihedral angle between planes I and J. β is the angle between the vector linking the ring centroids and the normal ring to I. CgJ_perp is the perpendicular distance of J on ring I. top

Compound	CgI···CgJ	Cg···Cg (Å)	α (°)	β (°)	CgJ_perp (Å)
(I)	Cg1···Cg4	3.969 (4)	28.26	20.50	3.718
(II)	Cg3···Cg1	3.9079 (12)	22.63	16.88	3.740

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Supra­molecular architectures in the salt trimethoprimium ferrocene-1-carboxyl­ate and the cocrystal 4-amino-5-chloro-2,6-di­methyl­pyrimidine–ferrocene-1-carb­oxy­lic acid (1/1)

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Supramolecular architectures in the salt trimethoprimium ferrocene-1-carboxylate and the cocrystal 4-amino-5-chloro-2,6-dimethylpyrimidine–ferrocene-1-carboxylic acid (1/1)