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The crystal structures and packing features of two homologous Meyer's bicyclic lactams with fused pyrrolidone and medium-sized perhydropyrimidine rings, namely, 8a-phenyl-2,3,4,7,8,8a-hexahydropyrrolo[1,2-
a]pyrimidin-6(1
H)-one, C
13H
16N
2O (
1), and 8a-(4-methylphenyl)-2,3,4,7,8,8a-hexahydropyrrolo[1,2-
a]pyrimidin-6(1
H)-one, C
14H
18N
2O (
2), were elucidated, and Hirshfeld surface plots were calculated and drawn for visualization and a deeper analysis of the intermolecular noncovalent interactions. Molecules of
1 and
2 are weakly linked by intermolecular C=O
H—N hydrogen bonds into chains, which are in turn weakly linked by other C=O
H—C
ar interactions. The steric volume of the substituent significantly affects the crystal packing pattern.
Supporting information
CCDC references: 1980026; 1980027
Data collection: APEX2 (Bruker, 2014) for (1); CrysAlis PRO (Agilent, 2014) for (2). Cell refinement: SAINT (Bruker, 2014) for (1); CrysAlis PRO (Agilent, 2014) for (2). Data reduction: SAINT (Bruker, 2014) for (1); CrysAlis PRO (Agilent, 2014) for (2). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (1); SHELXS97 (Sheldrick, 2008) for (2). For both structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
8a-Phenyl-2,3,4,7,8,8a-hexahydropyrrolo[1,2-
a]pyrimidin-6(1
H)-one (1)
top
Crystal data top
C13H16N2O | F(000) = 464 |
Mr = 216.28 | Dx = 1.295 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0910 (13) Å | Cell parameters from 346 reflections |
b = 17.016 (4) Å | θ = 3–25° |
c = 10.707 (2) Å | µ = 0.08 mm−1 |
β = 90.581 (5)° | T = 120 K |
V = 1109.6 (4) Å3 | Needle, clear colourless |
Z = 4 | 0.3 × 0.11 × 0.09 mm |
Data collection top
Bruker SMART APEXII diffractometer | 3456 measured reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 3456 independent reflections |
Mirror optics monochromator | 2533 reflections with I > 2σ(I) |
Detector resolution: 7.9 pixels mm-1 | θmax = 30.9°, θmin = 2.3° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | k = −24→24 |
Tmin = 0.609, Tmax = 0.746 | l = −15→15 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.208 | w = 1/[σ2(Fo2) + (0.1028P)2 + 0.8443P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
3456 reflections | Δρmax = 0.35 e Å−3 |
264 parameters | Δρmin = −0.35 e Å−3 |
137 restraints | |
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. |
Refinement. Refined as a 2-component twin.
Twin law 1 0 0 0 -1 0 -0.036 0 -1 as determined with PLATON (Spek 2009). The refinement was carried out using the SHELX software package
version 2016/6 (Sheldrick, 2015). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.4836 (4) | 0.08090 (13) | 0.3214 (2) | 0.0152 (5) | 0.921 (4) |
N1 | 0.5999 (4) | 0.11258 (18) | 0.2270 (2) | 0.0138 (5) | 0.921 (4) |
O1 | 0.3219 (3) | 0.03783 (10) | 0.30857 (19) | 0.0206 (4) | 0.921 (4) |
C2 | 0.5851 (5) | 0.10959 (18) | 0.4429 (3) | 0.0217 (6) | 0.921 (4) |
H2A | 0.602477 | 0.065796 | 0.503067 | 0.026* | 0.921 (4) |
H2B | 0.493338 | 0.150976 | 0.481055 | 0.026* | 0.921 (4) |
N2 | 0.9784 (3) | 0.15293 (12) | 0.1970 (2) | 0.0166 (4) | 0.921 (4) |
H2 | 1.035 (7) | 0.108 (3) | 0.228 (4) | 0.053 (13)* | 0.921 (4) |
C3 | 0.8083 (5) | 0.14239 (15) | 0.4057 (2) | 0.0206 (5) | 0.921 (4) |
H3A | 0.924216 | 0.101996 | 0.415147 | 0.025* | 0.921 (4) |
H3B | 0.847812 | 0.188516 | 0.457581 | 0.025* | 0.921 (4) |
C4 | 0.7790 (4) | 0.16616 (17) | 0.2675 (3) | 0.0144 (5) | 0.921 (4) |
C5 | 0.9372 (4) | 0.14838 (15) | 0.0621 (3) | 0.0201 (5) | 0.921 (4) |
H5A | 1.077124 | 0.137261 | 0.019327 | 0.024* | 0.921 (4) |
H5B | 0.882744 | 0.199912 | 0.032093 | 0.024* | 0.921 (4) |
C6 | 0.7698 (4) | 0.08480 (15) | 0.0273 (2) | 0.0199 (5) | 0.921 (4) |
H6A | 0.743844 | 0.085066 | −0.064164 | 0.024* | 0.921 (4) |
H6B | 0.827834 | 0.032506 | 0.051106 | 0.024* | 0.921 (4) |
C7 | 0.5545 (4) | 0.09994 (15) | 0.0945 (2) | 0.0166 (5) | 0.921 (4) |
H7A | 0.481220 | 0.146814 | 0.058574 | 0.020* | 0.921 (4) |
H7B | 0.455239 | 0.054324 | 0.083646 | 0.020* | 0.921 (4) |
C8 | 0.7093 (6) | 0.25260 (17) | 0.2538 (4) | 0.0145 (5) | 0.921 (4) |
C9 | 0.4926 (5) | 0.27548 (15) | 0.2269 (4) | 0.0160 (5) | 0.921 (4) |
H9 | 0.381244 | 0.236931 | 0.215932 | 0.019* | 0.921 (4) |
C10 | 0.4416 (4) | 0.35504 (14) | 0.2163 (3) | 0.0169 (5) | 0.921 (4) |
H10 | 0.294774 | 0.370667 | 0.198879 | 0.020* | 0.921 (4) |
C11 | 0.6039 (6) | 0.41160 (19) | 0.2311 (4) | 0.0192 (7) | 0.921 (4) |
H11 | 0.569100 | 0.465616 | 0.220260 | 0.023* | 0.921 (4) |
C12 | 0.8179 (7) | 0.3892 (2) | 0.2618 (6) | 0.0190 (10) | 0.921 (4) |
H12 | 0.927703 | 0.427967 | 0.275887 | 0.023* | 0.921 (4) |
C13 | 0.8696 (5) | 0.30968 (17) | 0.2718 (4) | 0.0169 (6) | 0.921 (4) |
H13 | 1.015990 | 0.294321 | 0.291188 | 0.020* | 0.921 (4) |
C1A | 0.491 (5) | 0.0814 (18) | 0.161 (3) | 0.030 (6) | 0.079 (4) |
N1A | 0.590 (7) | 0.107 (3) | 0.266 (2) | 0.027 (6) | 0.079 (4) |
O1A | 0.338 (4) | 0.0370 (15) | 0.176 (3) | 0.037 (6) | 0.079 (4) |
C2A | 0.632 (5) | 0.103 (2) | 0.050 (3) | 0.031 (6) | 0.079 (4) |
H2AA | 0.547629 | 0.135851 | −0.009354 | 0.037* | 0.079 (4) |
H2AB | 0.678539 | 0.054381 | 0.005710 | 0.037* | 0.079 (4) |
N2A | 0.973 (4) | 0.1564 (16) | 0.319 (2) | 0.024 (5) | 0.079 (4) |
H2AC | 1.041512 | 0.112028 | 0.303136 | 0.029* | 0.079 (4) |
C3A | 0.831 (6) | 0.147 (2) | 0.099 (3) | 0.033 (7) | 0.079 (4) |
H3AA | 0.846898 | 0.198329 | 0.056234 | 0.040* | 0.079 (4) |
H3AB | 0.967445 | 0.116088 | 0.087103 | 0.040* | 0.079 (4) |
C4A | 0.781 (5) | 0.158 (2) | 0.238 (3) | 0.021 (6) | 0.079 (4) |
C5A | 0.918 (5) | 0.1543 (16) | 0.452 (2) | 0.024 (5) | 0.079 (4) |
H5AA | 0.871348 | 0.207421 | 0.478545 | 0.028* | 0.079 (4) |
H5AB | 1.050360 | 0.139965 | 0.500942 | 0.028* | 0.079 (4) |
C6A | 0.735 (5) | 0.096 (2) | 0.481 (3) | 0.034 (6) | 0.079 (4) |
H6AA | 0.792512 | 0.041838 | 0.472348 | 0.041* | 0.079 (4) |
H6AB | 0.690551 | 0.102888 | 0.569346 | 0.041* | 0.079 (4) |
C7A | 0.533 (5) | 0.105 (3) | 0.397 (3) | 0.028 (6) | 0.079 (4) |
H7AA | 0.431041 | 0.060686 | 0.412597 | 0.034* | 0.079 (4) |
H7AB | 0.455657 | 0.154269 | 0.419277 | 0.034* | 0.079 (4) |
C8A | 0.709 (6) | 0.243 (2) | 0.247 (5) | 0.020* | 0.079 (4) |
C9A | 0.497 (6) | 0.2717 (17) | 0.265 (3) | 0.009 (8)* | 0.079 (4) |
H9A | 0.381025 | 0.234504 | 0.272745 | 0.010* | 0.079 (4) |
C10A | 0.444 (6) | 0.3511 (16) | 0.273 (3) | 0.026 (8)* | 0.079 (4) |
H10A | 0.294248 | 0.364117 | 0.285830 | 0.032* | 0.079 (4) |
C11A | 0.590 (7) | 0.412 (3) | 0.262 (4) | 0.019 (12)* | 0.079 (4) |
H11A | 0.551984 | 0.466378 | 0.265931 | 0.022* | 0.079 (4) |
C12A | 0.803 (10) | 0.384 (4) | 0.246 (7) | 0.05 (3)* | 0.079 (4) |
H12A | 0.918753 | 0.421052 | 0.240082 | 0.055* | 0.079 (4) |
C13A | 0.855 (10) | 0.304 (3) | 0.237 (5) | 0.034 (17)* | 0.079 (4) |
H13A | 1.003834 | 0.291209 | 0.222422 | 0.041* | 0.079 (4) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0170 (10) | 0.0079 (9) | 0.0207 (11) | 0.0008 (8) | 0.0029 (9) | 0.0017 (8) |
N1 | 0.0157 (9) | 0.0100 (10) | 0.0158 (10) | −0.0029 (7) | 0.0014 (9) | 0.0022 (10) |
O1 | 0.0172 (8) | 0.0127 (8) | 0.0320 (10) | −0.0027 (6) | 0.0021 (7) | 0.0029 (7) |
C2 | 0.0312 (15) | 0.0178 (12) | 0.0160 (12) | −0.0041 (11) | 0.0013 (10) | 0.0004 (11) |
N2 | 0.0144 (9) | 0.0119 (9) | 0.0236 (10) | 0.0006 (7) | −0.0014 (8) | 0.0007 (7) |
C3 | 0.0269 (13) | 0.0160 (11) | 0.0189 (11) | −0.0044 (9) | −0.0045 (10) | 0.0021 (9) |
C4 | 0.0156 (10) | 0.0092 (11) | 0.0184 (12) | −0.0020 (8) | −0.0032 (10) | −0.0012 (10) |
C5 | 0.0180 (11) | 0.0199 (11) | 0.0224 (12) | −0.0005 (9) | 0.0050 (10) | 0.0000 (9) |
C6 | 0.0211 (12) | 0.0191 (11) | 0.0195 (11) | −0.0014 (9) | 0.0034 (9) | −0.0038 (9) |
C7 | 0.0171 (11) | 0.0158 (11) | 0.0169 (11) | −0.0012 (9) | −0.0013 (9) | −0.0025 (9) |
C8 | 0.0151 (10) | 0.0093 (11) | 0.0191 (12) | 0.0005 (8) | 0.0011 (8) | −0.0011 (9) |
C9 | 0.0163 (12) | 0.0150 (12) | 0.0166 (15) | −0.0009 (8) | −0.0017 (11) | −0.0016 (10) |
C10 | 0.0178 (11) | 0.0159 (11) | 0.0170 (13) | 0.0036 (8) | −0.0012 (9) | −0.0001 (9) |
C11 | 0.0230 (15) | 0.0121 (13) | 0.0224 (19) | 0.0031 (9) | 0.0039 (13) | −0.0015 (12) |
C12 | 0.0194 (16) | 0.0089 (13) | 0.0288 (16) | −0.0029 (9) | 0.0013 (12) | −0.0011 (11) |
C13 | 0.0145 (12) | 0.0126 (12) | 0.0237 (18) | −0.0014 (8) | 0.0004 (12) | −0.0005 (11) |
C1A | 0.031 (12) | 0.022 (12) | 0.036 (9) | −0.003 (9) | −0.003 (8) | −0.004 (11) |
N1A | 0.030 (10) | 0.022 (13) | 0.028 (7) | −0.002 (8) | −0.002 (7) | 0.003 (11) |
O1A | 0.021 (10) | 0.028 (12) | 0.061 (16) | 0.000 (7) | −0.014 (9) | 0.008 (10) |
C2A | 0.038 (13) | 0.024 (12) | 0.030 (8) | 0.002 (10) | 0.001 (8) | −0.015 (10) |
N2A | 0.021 (7) | 0.023 (8) | 0.029 (7) | 0.011 (6) | 0.001 (5) | −0.007 (7) |
C3A | 0.038 (14) | 0.037 (16) | 0.026 (7) | −0.008 (11) | 0.003 (7) | −0.004 (11) |
C4A | 0.026 (8) | 0.013 (10) | 0.025 (7) | 0.003 (6) | 0.000 (5) | −0.003 (7) |
C5A | 0.030 (11) | 0.014 (11) | 0.026 (6) | 0.003 (8) | −0.002 (7) | −0.004 (10) |
C6A | 0.029 (11) | 0.043 (14) | 0.030 (9) | −0.011 (9) | −0.008 (8) | −0.001 (11) |
C7A | 0.022 (10) | 0.031 (16) | 0.031 (8) | 0.006 (10) | 0.001 (8) | 0.006 (12) |
Geometric parameters (Å, º) top
C1—N1 | 1.353 (3) | C1A—N1A | 1.339 (19) |
C1—O1 | 1.234 (3) | C1A—O1A | 1.213 (19) |
C1—C2 | 1.515 (4) | C1A—C2A | 1.52 (2) |
N1—C4 | 1.483 (3) | N1A—C4A | 1.485 (19) |
N1—C7 | 1.458 (3) | N1A—C7A | 1.45 (2) |
C2—H2A | 0.9900 | C2A—H2AA | 0.9900 |
C2—H2B | 0.9900 | C2A—H2AB | 0.9900 |
C2—C3 | 1.526 (4) | C2A—C3A | 1.52 (2) |
N2—H2 | 0.90 (5) | N2A—H2AC | 0.8805 |
N2—C4 | 1.454 (4) | N2A—C4A | 1.453 (19) |
N2—C5 | 1.466 (4) | N2A—C5A | 1.465 (19) |
C3—H3A | 0.9900 | C3A—H3AA | 0.9900 |
C3—H3B | 0.9900 | C3A—H3AB | 0.9900 |
C3—C4 | 1.542 (4) | C3A—C4A | 1.54 (2) |
C4—C8 | 1.538 (3) | C4A—C8A | 1.525 (19) |
C5—H5A | 0.9900 | C5A—H5AA | 0.9900 |
C5—H5B | 0.9900 | C5A—H5AB | 0.9900 |
C5—C6 | 1.530 (4) | C5A—C6A | 1.527 (19) |
C6—H6A | 0.9900 | C6A—H6AA | 0.9900 |
C6—H6B | 0.9900 | C6A—H6AB | 0.9900 |
C6—C7 | 1.524 (4) | C6A—C7A | 1.52 (2) |
C7—H7A | 0.9900 | C7A—H7AA | 0.9900 |
C7—H7B | 0.9900 | C7A—H7AB | 0.9900 |
C8—C9 | 1.403 (4) | C8A—C9A | 1.394 (19) |
C8—C13 | 1.389 (4) | C8A—C13A | 1.37 (2) |
C9—H9 | 0.9500 | C9A—H9A | 0.9500 |
C9—C10 | 1.393 (3) | C9A—C10A | 1.391 (19) |
C10—H10 | 0.9500 | C10A—H10A | 0.9500 |
C10—C11 | 1.387 (4) | C10A—C11A | 1.378 (19) |
C11—H11 | 0.9500 | C11A—H11A | 0.9500 |
C11—C12 | 1.394 (5) | C11A—C12A | 1.39 (2) |
C12—H12 | 0.9500 | C12A—H12A | 0.9500 |
C12—C13 | 1.394 (3) | C12A—C13A | 1.40 (2) |
C13—H13 | 0.9500 | C13A—H13A | 0.9500 |
| | | |
N1—C1—C2 | 107.5 (2) | N1A—C1A—C2A | 109 (2) |
O1—C1—N1 | 125.2 (2) | O1A—C1A—N1A | 115 (3) |
O1—C1—C2 | 127.3 (2) | O1A—C1A—C2A | 134 (3) |
C1—N1—C4 | 114.6 (2) | C1A—N1A—C4A | 111 (2) |
C1—N1—C7 | 124.9 (2) | C1A—N1A—C7A | 134 (3) |
C7—N1—C4 | 120.4 (2) | C7A—N1A—C4A | 114 (3) |
C1—C2—H2A | 110.8 | C1A—C2A—H2AA | 110.2 |
C1—C2—H2B | 110.8 | C1A—C2A—H2AB | 110.2 |
C1—C2—C3 | 104.5 (2) | C1A—C2A—C3A | 108 (2) |
H2A—C2—H2B | 108.9 | H2AA—C2A—H2AB | 108.5 |
C3—C2—H2A | 110.8 | C3A—C2A—H2AA | 110.2 |
C3—C2—H2B | 110.8 | C3A—C2A—H2AB | 110.2 |
C4—N2—H2 | 105 (3) | C4A—N2A—H2AC | 106.1 |
C4—N2—C5 | 112.6 (2) | C4A—N2A—C5A | 113 (2) |
C5—N2—H2 | 112 (3) | C5A—N2A—H2AC | 106.4 |
C2—C3—H3A | 110.8 | C2A—C3A—H3AA | 111.2 |
C2—C3—H3B | 110.8 | C2A—C3A—H3AB | 111.2 |
C2—C3—C4 | 104.6 (2) | C2A—C3A—C4A | 103 (2) |
H3A—C3—H3B | 108.9 | H3AA—C3A—H3AB | 109.1 |
C4—C3—H3A | 110.8 | C4A—C3A—H3AA | 111.2 |
C4—C3—H3B | 110.8 | C4A—C3A—H3AB | 111.2 |
N1—C4—C3 | 101.3 (2) | N1A—C4A—C3A | 107 (2) |
N1—C4—C8 | 111.0 (3) | N1A—C4A—C8A | 109 (3) |
N2—C4—N1 | 111.6 (2) | N2A—C4A—N1A | 120 (3) |
N2—C4—C3 | 111.6 (2) | N2A—C4A—C3A | 114 (3) |
N2—C4—C8 | 109.3 (2) | N2A—C4A—C8A | 102 (3) |
C8—C4—C3 | 111.8 (3) | C8A—C4A—C3A | 104 (3) |
N2—C5—H5A | 109.1 | N2A—C5A—H5AA | 109.0 |
N2—C5—H5B | 109.1 | N2A—C5A—H5AB | 109.0 |
N2—C5—C6 | 112.6 (2) | N2A—C5A—C6A | 113 (3) |
H5A—C5—H5B | 107.8 | H5AA—C5A—H5AB | 107.8 |
C6—C5—H5A | 109.1 | C6A—C5A—H5AA | 109.0 |
C6—C5—H5B | 109.1 | C6A—C5A—H5AB | 109.0 |
C5—C6—H6A | 109.7 | C5A—C6A—H6AA | 108.9 |
C5—C6—H6B | 109.7 | C5A—C6A—H6AB | 108.9 |
H6A—C6—H6B | 108.2 | H6AA—C6A—H6AB | 107.7 |
C7—C6—C5 | 109.9 (2) | C7A—C6A—C5A | 114 (3) |
C7—C6—H6A | 109.7 | C7A—C6A—H6AA | 108.9 |
C7—C6—H6B | 109.7 | C7A—C6A—H6AB | 108.9 |
N1—C7—C6 | 109.2 (2) | N1A—C7A—C6A | 112 (3) |
N1—C7—H7A | 109.8 | N1A—C7A—H7AA | 109.2 |
N1—C7—H7B | 109.8 | N1A—C7A—H7AB | 109.2 |
C6—C7—H7A | 109.8 | C6A—C7A—H7AA | 109.2 |
C6—C7—H7B | 109.8 | C6A—C7A—H7AB | 109.2 |
H7A—C7—H7B | 108.3 | H7AA—C7A—H7AB | 107.9 |
C9—C8—C4 | 122.9 (3) | C9A—C8A—C4A | 127 (4) |
C13—C8—C4 | 117.5 (3) | C13A—C8A—C4A | 122 (4) |
C13—C8—C9 | 119.5 (3) | C13A—C8A—C9A | 111 (4) |
C8—C9—H9 | 120.2 | C8A—C9A—H9A | 118.0 |
C10—C9—C8 | 119.6 (3) | C10A—C9A—C8A | 124 (3) |
C10—C9—H9 | 120.2 | C10A—C9A—H9A | 118.0 |
C9—C10—H10 | 119.8 | C9A—C10A—H10A | 117.3 |
C11—C10—C9 | 120.5 (3) | C11A—C10A—C9A | 125 (4) |
C11—C10—H10 | 119.8 | C11A—C10A—H10A | 117.3 |
C10—C11—H11 | 120.0 | C10A—C11A—H11A | 124.7 |
C10—C11—C12 | 120.0 (3) | C10A—C11A—C12A | 111 (5) |
C12—C11—H11 | 120.0 | C12A—C11A—H11A | 124.7 |
C11—C12—H12 | 120.2 | C11A—C12A—H12A | 118.1 |
C13—C12—C11 | 119.6 (4) | C11A—C12A—C13A | 124 (7) |
C13—C12—H12 | 120.2 | C13A—C12A—H12A | 118.1 |
C8—C13—C12 | 120.7 (4) | C8A—C13A—C12A | 126 (6) |
C8—C13—H13 | 119.7 | C8A—C13A—H13A | 117.2 |
C12—C13—H13 | 119.7 | C12A—C13A—H13A | 117.2 |
| | | |
C1—N1—C4—N2 | 137.1 (3) | C1A—N1A—C4A—N2A | −146 (4) |
C1—N1—C4—C3 | 18.2 (3) | C1A—N1A—C4A—C3A | −14 (5) |
C1—N1—C4—C8 | −100.7 (3) | C1A—N1A—C4A—C8A | 98 (4) |
C1—N1—C7—C6 | −136.0 (3) | C1A—N1A—C7A—C6A | 146 (6) |
C1—C2—C3—C4 | 25.7 (3) | C1A—C2A—C3A—C4A | −6 (4) |
N1—C1—C2—C3 | −15.2 (3) | N1A—C1A—C2A—C3A | −1 (5) |
N1—C4—C8—C9 | 10.0 (5) | N1A—C4A—C8A—C9A | −7 (5) |
N1—C4—C8—C13 | −171.4 (3) | N1A—C4A—C8A—C13A | 174 (3) |
O1—C1—N1—C4 | 176.5 (2) | O1A—C1A—N1A—C4A | 177 (3) |
O1—C1—N1—C7 | −0.9 (5) | O1A—C1A—N1A—C7A | −13 (8) |
O1—C1—C2—C3 | 166.2 (2) | O1A—C1A—C2A—C3A | −166 (4) |
C2—C1—N1—C4 | −2.2 (3) | C2A—C1A—N1A—C4A | 9 (5) |
C2—C1—N1—C7 | −179.6 (3) | C2A—C1A—N1A—C7A | 178 (5) |
C2—C3—C4—N1 | −26.0 (3) | C2A—C3A—C4A—N1A | 12 (4) |
C2—C3—C4—N2 | −145.0 (2) | C2A—C3A—C4A—N2A | 147 (3) |
C2—C3—C4—C8 | 92.2 (3) | C2A—C3A—C4A—C8A | −103 (3) |
N2—C4—C8—C9 | 133.6 (4) | N2A—C4A—C8A—C9A | −134 (4) |
N2—C4—C8—C13 | −47.9 (4) | N2A—C4A—C8A—C13A | 47 (5) |
N2—C5—C6—C7 | 57.6 (3) | N2A—C5A—C6A—C7A | −50 (4) |
C3—C4—C8—C9 | −102.4 (4) | C3A—C4A—C8A—C9A | 107 (4) |
C3—C4—C8—C13 | 76.2 (4) | C3A—C4A—C8A—C13A | −72 (4) |
C4—N1—C7—C6 | 46.7 (4) | C4A—N1A—C7A—C6A | −45 (5) |
C4—N2—C5—C6 | −56.5 (3) | C4A—N2A—C5A—C6A | 44 (4) |
C4—C8—C9—C10 | 179.7 (3) | C4A—C8A—C9A—C10A | −180 (5) |
C4—C8—C13—C12 | −179.5 (4) | C4A—C8A—C13A—C12A | −179 (5) |
C5—N2—C4—N1 | 47.4 (3) | C5A—N2A—C4A—N1A | −42 (4) |
C5—N2—C4—C3 | 160.1 (2) | C5A—N2A—C4A—C3A | −171 (3) |
C5—N2—C4—C8 | −75.7 (3) | C5A—N2A—C4A—C8A | 78 (3) |
C5—C6—C7—N1 | −49.9 (3) | C5A—C6A—C7A—N1A | 50 (5) |
C7—N1—C4—N2 | −45.3 (4) | C7A—N1A—C4A—N2A | 43 (5) |
C7—N1—C4—C3 | −164.3 (3) | C7A—N1A—C4A—C3A | 175 (4) |
C7—N1—C4—C8 | 76.9 (4) | C7A—N1A—C4A—C8A | −74 (5) |
C8—C9—C10—C11 | 0.6 (6) | C8A—C9A—C10A—C11A | 1 (3) |
C9—C8—C13—C12 | −0.9 (7) | C9A—C8A—C13A—C12A | 1 (6) |
C9—C10—C11—C12 | −2.7 (6) | C9A—C10A—C11A—C12A | −1 (5) |
C10—C11—C12—C13 | 3.0 (8) | C10A—C11A—C12A—C13A | 2 (7) |
C11—C12—C13—C8 | −1.2 (8) | C11A—C12A—C13A—C8A | −2 (9) |
C13—C8—C9—C10 | 1.2 (6) | C13A—C8A—C9A—C10A | −1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.90 (5) | 2.28 (5) | 3.097 (3) | 151 (4) |
Symmetry code: (i) x+1, y, z. |
8a-(4-Methylphenyl)-2,3,4,7,8,8a-hexahydropyrrolo[1,2-
a]pyrimidin-6(1
H)-one (2)
top
Crystal data top
C14H18N2O | F(000) = 496 |
Mr = 230.30 | Dx = 1.256 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.143 (2) Å | Cell parameters from 2097 reflections |
b = 11.703 (3) Å | θ = 3.7–28.2° |
c = 10.776 (3) Å | µ = 0.08 mm−1 |
β = 107.84 (3)° | T = 295 K |
V = 1217.7 (6) Å3 | Block, clear colourless |
Z = 4 | 0.5 × 0.45 × 0.3 mm |
Data collection top
Agilent Xcalibur Ruby diffractometer | 2848 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2191 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 10.4752 pixels mm-1 | θmax = 29.4°, θmin = 3.0° |
ω scans | h = −12→8 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −14→14 |
Tmin = 0.601, Tmax = 1.000 | l = −12→13 |
5980 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0635P)2 + 0.2084P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2848 reflections | Δρmax = 0.24 e Å−3 |
159 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | |
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 | |
O1 | 0.70057 (11) | 0.12818 (10) | 0.80679 (12) | 0.0507 (3) | |
N1 | 0.59664 (11) | 0.30192 (10) | 0.80043 (11) | 0.0311 (3) | |
N2 | 0.55037 (12) | 0.49806 (11) | 0.72902 (12) | 0.0365 (3) | |
H1 | 0.6249 (18) | 0.5054 (15) | 0.7026 (17) | 0.048 (5)* | |
C1 | 0.62698 (13) | 0.20578 (13) | 0.74720 (15) | 0.0353 (3) | |
C2 | 0.55360 (16) | 0.21083 (15) | 0.60237 (16) | 0.0469 (4) | |
H2A | 0.472849 | 0.161530 | 0.578899 | 0.056* | |
H2B | 0.615012 | 0.187678 | 0.553429 | 0.056* | |
C3 | 0.51168 (15) | 0.33512 (15) | 0.57597 (14) | 0.0411 (4) | |
H3A | 0.422828 | 0.341447 | 0.508911 | 0.049* | |
H3B | 0.580360 | 0.377030 | 0.548401 | 0.049* | |
C4 | 0.50283 (13) | 0.38078 (12) | 0.70756 (13) | 0.0300 (3) | |
C5 | 0.58799 (15) | 0.53061 (13) | 0.86624 (16) | 0.0415 (4) | |
H5A | 0.505354 | 0.530092 | 0.893597 | 0.050* | |
H5B | 0.623850 | 0.608029 | 0.875765 | 0.050* | |
C6 | 0.69547 (16) | 0.45218 (14) | 0.95521 (15) | 0.0424 (4) | |
H6A | 0.781744 | 0.457989 | 0.934410 | 0.051* | |
H6B | 0.712783 | 0.475537 | 1.045166 | 0.051* | |
C7 | 0.64502 (15) | 0.32973 (14) | 0.93868 (14) | 0.0385 (4) | |
H7A | 0.719797 | 0.278714 | 0.983561 | 0.046* | |
H7B | 0.570158 | 0.320183 | 0.976219 | 0.046* | |
C8 | 0.35515 (13) | 0.37256 (12) | 0.71721 (13) | 0.0292 (3) | |
C9 | 0.30920 (15) | 0.28178 (13) | 0.77474 (16) | 0.0380 (4) | |
H9 | 0.370659 | 0.223704 | 0.813388 | 0.046* | |
C10 | 0.17292 (16) | 0.27566 (14) | 0.77592 (17) | 0.0434 (4) | |
H10 | 0.144806 | 0.213274 | 0.814970 | 0.052* | |
C11 | 0.07854 (14) | 0.35979 (13) | 0.72063 (16) | 0.0395 (4) | |
C12 | 0.12425 (15) | 0.45027 (13) | 0.66201 (16) | 0.0413 (4) | |
H12 | 0.062586 | 0.508303 | 0.623650 | 0.050* | |
C13 | 0.25920 (14) | 0.45645 (13) | 0.65909 (15) | 0.0370 (4) | |
H13 | 0.286285 | 0.517718 | 0.617584 | 0.044* | |
C14 | −0.07029 (17) | 0.35342 (17) | 0.7210 (2) | 0.0644 (6) | |
H14A | −0.097103 | 0.425618 | 0.748090 | 0.097* | |
H14B | −0.079059 | 0.294855 | 0.780383 | 0.097* | |
H14C | −0.129147 | 0.335739 | 0.634871 | 0.097* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0431 (6) | 0.0424 (7) | 0.0636 (8) | 0.0144 (5) | 0.0119 (5) | −0.0004 (6) |
N1 | 0.0266 (6) | 0.0343 (7) | 0.0313 (6) | 0.0050 (5) | 0.0070 (4) | 0.0008 (5) |
N2 | 0.0315 (6) | 0.0356 (7) | 0.0436 (7) | −0.0044 (5) | 0.0134 (5) | 0.0057 (6) |
C1 | 0.0235 (7) | 0.0372 (8) | 0.0460 (8) | 0.0004 (6) | 0.0118 (6) | −0.0038 (7) |
C2 | 0.0378 (8) | 0.0551 (11) | 0.0455 (9) | 0.0031 (7) | 0.0094 (7) | −0.0153 (8) |
C3 | 0.0353 (8) | 0.0572 (10) | 0.0316 (8) | −0.0004 (7) | 0.0115 (6) | 0.0010 (7) |
C4 | 0.0259 (7) | 0.0326 (8) | 0.0307 (7) | 0.0011 (5) | 0.0077 (5) | 0.0049 (6) |
C5 | 0.0372 (8) | 0.0346 (8) | 0.0518 (9) | −0.0048 (6) | 0.0121 (7) | −0.0051 (7) |
C6 | 0.0354 (8) | 0.0494 (10) | 0.0387 (8) | −0.0016 (7) | 0.0059 (6) | −0.0093 (7) |
C7 | 0.0373 (8) | 0.0454 (9) | 0.0303 (7) | 0.0091 (6) | 0.0067 (6) | 0.0021 (7) |
C8 | 0.0272 (7) | 0.0293 (7) | 0.0302 (7) | 0.0002 (5) | 0.0074 (5) | −0.0001 (6) |
C9 | 0.0334 (8) | 0.0316 (8) | 0.0514 (9) | 0.0066 (6) | 0.0164 (6) | 0.0095 (7) |
C10 | 0.0410 (9) | 0.0356 (9) | 0.0599 (10) | −0.0012 (7) | 0.0248 (7) | 0.0072 (8) |
C11 | 0.0304 (7) | 0.0363 (8) | 0.0539 (9) | −0.0023 (6) | 0.0160 (6) | −0.0082 (7) |
C12 | 0.0303 (8) | 0.0342 (8) | 0.0544 (10) | 0.0050 (6) | 0.0054 (6) | 0.0011 (7) |
C13 | 0.0322 (8) | 0.0318 (8) | 0.0445 (8) | −0.0004 (6) | 0.0079 (6) | 0.0084 (7) |
C14 | 0.0366 (9) | 0.0560 (12) | 0.1085 (17) | −0.0010 (8) | 0.0339 (10) | −0.0055 (11) |
Geometric parameters (Å, º) top
O1—C1 | 1.2250 (18) | C7—C6 | 1.514 (2) |
N1—C1 | 1.3409 (18) | C8—C4 | 1.5360 (18) |
N1—C4 | 1.4749 (17) | C8—C9 | 1.381 (2) |
N1—C7 | 1.4554 (18) | C8—C13 | 1.3892 (19) |
N2—C5 | 1.460 (2) | C9—C10 | 1.388 (2) |
C1—C2 | 1.510 (2) | C11—C10 | 1.375 (2) |
C3—C2 | 1.518 (2) | C11—C12 | 1.384 (2) |
C4—N2 | 1.4497 (19) | C11—C14 | 1.513 (2) |
C4—C3 | 1.543 (2) | C13—C12 | 1.381 (2) |
C6—C5 | 1.520 (2) | | |
| | | |
C1—N1—C4 | 114.82 (12) | C8—C4—C3 | 111.90 (11) |
C1—N1—C7 | 125.17 (12) | N2—C5—C6 | 113.31 (13) |
C7—N1—C4 | 119.98 (11) | C7—C6—C5 | 110.26 (12) |
C4—N2—C5 | 112.31 (12) | N1—C7—C6 | 109.15 (12) |
O1—C1—N1 | 125.50 (14) | C9—C8—C4 | 123.29 (12) |
O1—C1—C2 | 126.79 (14) | C9—C8—C13 | 117.38 (12) |
N1—C1—C2 | 107.70 (12) | C13—C8—C4 | 119.23 (12) |
C1—C2—C3 | 104.61 (12) | C8—C9—C10 | 121.18 (13) |
C2—C3—C4 | 104.56 (12) | C11—C10—C9 | 121.47 (14) |
N1—C4—C3 | 101.52 (11) | C10—C11—C12 | 117.36 (13) |
N1—C4—C8 | 110.77 (11) | C10—C11—C14 | 121.75 (15) |
N2—C4—N1 | 111.74 (11) | C12—C11—C14 | 120.88 (14) |
N2—C4—C3 | 111.36 (12) | C13—C12—C11 | 121.58 (13) |
N2—C4—C8 | 109.39 (11) | C12—C13—C8 | 121.01 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1···O1i | 0.890 (18) | 2.306 (18) | 3.0737 (17) | 144.4 (15) |
Symmetry code: (i) −x+3/2, y+1/2, −z+3/2. |
Calculated hydrogen-bond geometry (Å, °) and energy (kcal mol-1) topPh is phenyl and p-Tol is p-tolyl or 4-methylphenyl. |
Functional | R | D—H | H···A | D···A | D—H···A | Energy |
MPWB95 | Ph | 1.027 | 2.125 | 3.090 | 155.63 | 1.06 |
MPWB95 | p-Tol | - | - | - | - | - |
WB97XD | Ph | 1.018 | 2.034 | 2.975 | 152.52 | 8.53 |
WB97XD | p-Tol | - | - | - | - | - |
M06-2X | Ph | 1.019 | 2.082 | 3.028 | 153.82 | 6.45 |
M06-2X | p-Tol | 1.017 | 2.058 | 2.977 | 148.83 | 5.56 |
B97-D3 | Ph | 1.022 | 2.069 | 3.018 | 153.63 | 7.59 |
B97-D3 | p-Tol | 1.020 | 2.036 | 3.056 | 178.53 | 6.78 |
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