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In the salt trimethoprimium ferrocenecarboxylate [systematic name: 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium ferrocene-1-carboxylate], (C
14H
19N
4O
3)[Fe(C
5H
5)(C
6H
4O
2)], (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(C
5H
5)(C
6H
5O
2)]·C
6H
8ClN
3, (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
CgCgC 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
CgCgC pseudo-torsion angles, which are in the range 79.26–80.94°. Both crystal structures are further stabilized by weak π–π interactions.
Supporting information
CCDC references: 1569235; 1569234
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 |
Mr = 520.36 | Dx = 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 | Rint = 0.025 |
Detector resolution: 10.4933 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −17→17 |
Tmin = 0.888, Tmax = 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(Fo2) + (0.0374P)2 + 1.0417P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
5532 reflections | Δρmax = 0.29 e Å−3 |
380 parameters | Δρmin = −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 | Uiso*/Ueq | 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 |
Mr = 387.64 | Dx = 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 | Rint = 0.029 |
Detector resolution: 10.4933 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
ω scans | h = −27→27 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | k = −9→9 |
Tmin = 0.840, Tmax = 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(Fo2) + (0.036P)2 + 2.0431P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.002 |
3927 reflections | Δρmax = 0.29 e Å−3 |
228 parameters | Δρmin = −0.32 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 | Uiso*/Ueq | |
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.
CgJperp is the perpendicular distance of J on ring
I. topCompound | CgI···CgJ | Cg···Cg (Å) | α (°) | β (°) | CgJperp (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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