Crystal structures, packing features, Hirshfeld surface analyses and DFT calculations of hydrogen-bond energy of two homologous 8a-aryl-2,3,4,7,8,8a-hexa­hydro­pyrrolo­[1,2-a]pyrimidin-6(1H)-ones

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(1H)-one, C₁₃H₁₆N₂O (1), and 8a-(4-methyl­phen­yl)-2,3,4,7,8,8a-hexa­hydro­pyrrolo­[1,2-a]pyrimidin-6(1H)-one, C₁₄H₁₈N₂O (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.

Computing details

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(1H)-one (1)

Crystal data

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) Å^3	Needle, clear colourless
Z = 4	0.3 × 0.11 × 0.09 mm

Data collection

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

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.070	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.208	w = 1/[σ^2(Fo^2) + (0.1028P)^2 + 0.8443P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	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(1H)-one (2)

Crystal data

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) Å^3	Block, clear colourless
Z = 4	0.5 × 0.45 × 0.3 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0635P)^2 + 0.2084P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1^i	0.890 (18)	2.306 (18)	3.0737 (17)	144.4 (15)

Symmetry code: (i) −x+3/2, y+1/2, −z+3/2.