Prediction of molecular crystal structures by a crystallographic QM/MM model with full space-group symmetry

A crystallographic quantum-mechanical/molecular-mechanical model (c-QM/MM model) with full space-group symmetry has been developed for molecular crystals. The lattice energy was calculated by quantum-mechanical methods for short-range interactions and force-field methods for long-range interactions. The quantum-mechanical calculations covered the interactions within the molecule and the interactions of a reference molecule with each of the surrounding 12–15 molecules. The interactions with all other molecules were treated by force-field methods. In each optimization step the energies in the QM and MM shells were calculated separately as single-point energies; after adding both energy contributions, the crystal structure (including the lattice parameters) was optimized accordingly. The space-group symmetry was main­tained throughout. Crystal structures with more than one molecule per asymmetric unit, e.g. structures with Z′ = 2, hydrates and solvates, have been optimized as well. Test calculations with different quantum-mechanical methods on nine small organic molecules revealed that the density functional theory methods with dispersion correction using the B97-D functional with 6-31G* basis set in combination with the DREIDING force field reproduced the experimental crystal structures with good accuracy. Subsequently the c-QM/MM method was applied to nine compounds from the CCDC blind tests resulting in good energy rankings and excellent geometric accuracies.

Computing details

Figures

(1_ethane.cif)

Crystal data

?	β = 90.416°
Mr = ?	V = 122.75 Å^3
Monoclinic, P21/n	Z = ?
a = 4.225 Å	? radiation, λ = ? Å
b = 5.441 Å	× × mm
c = 5.592 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	−0.04014	0.10223	−0.09583
H2	0.07587	0.07091	−0.27665
H3	−0.28572	0.10915	−0.13262
H4	0.02734	0.28518	−0.02697

(2_propane.cif)

Crystal data

?	β = 91.033°
Mr = ?	V = 342.66 Å^3
Monoclinic, P2_1/n	Z = ?
a = 4.1832 Å	? radiation, λ = ? Å
b = 12.7487 Å	× × mm
c = 7.0031 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	0.21539	−0.05478	0.22443
H2	−0.04922	−0.05712	0.19162
H3	0.34094	−0.07861	0.08832
H4	0.28146	0.02880	0.25622
C5	0.30727	−0.12883	0.39745
H6	0.17925	−0.10298	0.53182
H7	0.57023	−0.12039	0.43299
C8	0.22961	−0.24644	0.35443
H9	−0.03398	−0.25867	0.32679
H10	0.35762	−0.27428	0.22179
H11	0.30432	−0.29850	0.47853

(3_congressane.cif)

Crystal data

?	V = 891.26 Å^3
Mr = ?	Z = ?
Cubic, Pa3	? radiation, λ = ? Å
a = 9.6325 Å	× × mm

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	−0.35998	−0.64002	−0.14002
C2	−0.26964	−0.54790	−0.04559
C3	−0.36218	−0.45578	0.04601
H4	−0.29968	−0.70032	−0.20032
H5	−0.22825	−0.60221	0.03361
H6	−0.23497	−0.48739	−0.09570

(4_hexamethylenetetramine.cif)

Crystal data

?	V = 320.15 Å^3
Mr = ?	Z = ?
Cubic, I43m	? radiation, λ = ? Å
a = 6.841 Å	× × mm

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	0.24660	−0.00162	−0.00162
N2	0.12340	0.12340	0.12340
H3	0.33434	0.08946	−0.09271

(5_benzene_P21c.cif)

Crystal data

?	β = 110.028°
Mr = ?	V = 208.89 Å^3
Monoclinic, P21/c	Z = ?
a = 5.4170 Å	? radiation, λ = ? Å
b = 5.4492 Å	× × mm
c = 7.5320 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	−0.26140	−0.02341	−0.11498
C2	−0.08015	−0.20216	−0.11875
C3	−0.18117	0.17844	0.00379
H4	−0.44012	−0.03919	−0.19358
H5	−0.13486	−0.34060	−0.20008
H6	−0.30517	0.30109	0.00653

(5_benzene_Pbca.cif)

Crystal data

?	c = 6.7042 Å
Mr = ?	V = 448.59 Å^3
Orthorhombic, Pbca	Z = ?
a = 7.3429 Å	? radiation, λ = ? Å
b = 9.1125 Å	× × mm

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	−0.43891	−0.14400	−0.50701
C2	−0.36142	−0.04621	−0.37201
C3	−0.57749	−0.09903	−0.63459
H4	−0.39473	−0.25864	−0.51249
H5	−0.25262	−0.08074	−0.27236
H6	−0.63798	−0.17377	−0.73972

(6_methanole_P-1.cif)

Crystal data

?	β = 102.890°
Mr = ?	γ = 93.850°
Triclinic, P1	V = 238.16 Å^3
a = 7.6700 Å	Z = ?
b = 4.4101 Å	? radiation, λ = ? Å
c = 7.2405 Å	× × mm
α = 88.100°

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
O1	−0.2720	−0.4961	−0.1371
C2	−0.3927	−0.7409	−0.1166
H3	−0.2977	−0.4238	−0.2648
H4	−0.3284	−0.8951	−0.0054
H5	−0.5101	−0.6565	−0.0789
H6	−0.4335	−0.8614	−0.2497
O7	−0.1345	−0.3119	−0.7937
C8	−0.0237	−0.0441	−0.7717
H9	−0.2562	−0.2627	−0.8317
H10	0.0971	−0.0802	−0.6636
H11	0.0126	0.0186	−0.9056
H12	−0.0947	0.1378	−0.7289
O13	−0.2260	−0.4839	−0.4987
C14	−0.3332	−0.7437	−0.5665
H15	−0.1035	−0.5296	−0.4710
H16	−0.4625	−0.7383	−0.5283
H17	−0.3531	−0.7492	−0.7201
H18	−0.2674	−0.9457	−0.5038

(methanol_P212121)

Crystal data

?	c = 8.8671 Å
Mr = ?	V = 200.53 Å^3
Orthorhombic, P212121	Z = ?
a = 4.8728 Å	? radiation, λ = ? Å
b = 4.6411 Å	× × mm

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	−0.4960	−0.0051	−0.1052
O1	−0.2331	0.0254	−0.1727
H1	−0.1980	−0.1475	−0.2296
H2	−0.5325	0.1909	−0.0413
H3	−0.6596	−0.0280	−0.1887
H4	−0.5057	−0.1880	−0.0277

(7_ethanole_Pc.cif)

Crystal data

?	β = 100.6°
Mr = ?	V = 314.34 Å^3
Monoclinic, Pc	Z = ?
a = 5.482 Å	? radiation, λ = ? Å
b = 6.962 Å	× × mm
c = 8.401 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	0.0046	0.2957	0.1431
C4	0.2133	0.2740	0.0459
H1	−0.0495	0.0215	0.1778
H8	0.0421	0.4206	0.2256
H9	−0.1791	0.3205	0.0586
H10	0.1760	0.1497	−0.0377
H11	0.3958	0.2516	0.1303
H12	0.2256	0.4030	−0.0287
O1	−0.0076	0.1335	0.2485
C2	−0.3951	0.2291	−0.4792
C3	−0.4682	0.2537	−0.3133
H2	−0.0839	0.1634	−0.5523
H3	−0.5114	0.1154	−0.5512
H4	−0.4306	0.3642	−0.5506
H5	−0.3542	0.3679	−0.2426
H6	−0.4342	0.1191	−0.2430
H7	−0.6685	0.2919	−0.3298
O2	−0.1318	0.1790	−0.4470

(7_ethanole_P21c)

Crystal data

?	β = 114.800°
Mr = ?	V = 312.40 Å^3
Monoclinic, P21/c	Z = ?
a = 7.8260 Å	? radiation, λ = ? Å
b = 5.6038 Å	× × mm
c = 7.8470 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
O1	−0.0663	0.2968	0.1625
C2	−0.2920	0.0235	−0.0371
C3	−0.2464	0.2847	0.0071
H4	−0.0365	0.4630	0.1915
H5	−0.2451	0.3770	−0.1154
H6	−0.3545	0.3695	0.0409
H7	−0.2945	−0.0675	0.0844
H8	−0.1852	−0.0600	−0.0719
H9	−0.4286	0.0025	−0.1552

(8_acetac_Pna21.cif)

Crystal data

?	c = 5.7499 Å
Mr = ?	V = 312.70 Å^3
Orthorhombic, Pna21	Z = ?
a = 13.3086 Å	? radiation, λ = ? Å
b = 4.0890 Å	× × mm

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	0.14478	0.28747	0.17375
C2	0.06909	0.37791	0.35168
H1	0.16167	0.05261	−0.11431
H2	0.10769	0.51174	0.49515
H3	0.01268	0.54173	0.28231
H4	0.03268	0.16968	0.42490
O1	0.10837	0.10913	0.00217
O2	0.23259	0.37199	0.17975

(oxalic_acid_P21c.cif)

Crystal data

?	β = 115.830°
Mr = ?	V = 157.43 Å^3
Monoclinic, P21/c	Z = ?
a = 5.8510 Å	? radiation, λ = ? Å
b = 6.0150 Å	× × mm
c = 4.9699 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	0.1282	0.004953	−0.006372
H2	0.459247	−0.098608	0.200781
O3	0.166604	0.103896	−0.195963
O4	0.302354	−0.111628	0.22216

(9_oxalic_acid_Pbca.cif)

Crystal data

?	c = 7.8524 Å
Mr = ?	V = 313.88 Å^3
Orthorhombic, Pcab	Z = ?
a = 6.5594 Å	? radiation, λ = ? Å
b = 6.0940 Å	× × mm

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
O1	0.15710	0.26470	0.00130
O2	0.02330	0.45710	−0.22090
C3	0.05540	0.41490	−0.05480
H4	0.09730	0.34410	−0.28260

(I_1_opt.cif)

Crystal data

?	c = 14.2229 Å
Mr = ?	V = 900.33 Å^3
Orthorhombic, Pbca	Z = ?
a = 5.3187 Å	? radiation, λ = ? Å
b = 12.4468 Å	× × mm

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
O1	0.03465	0.20387	0.11795
C2	0.15450	0.11877	0.16644
H3	0.32472	0.14152	0.20446
C4	0.01897	0.02604	0.15096
C5	−0.05653	−0.09417	0.15630
H6	−0.10860	−0.12419	0.22796
H7	0.07785	−0.15151	0.12389
C8	−0.28824	−0.06325	0.08957
H9	−0.47394	−0.07560	0.12227
H10	−0.28607	−0.10180	0.01838
C11	−0.18999	0.05343	0.09140
C12	−0.17805	0.16211	0.07195
H13	−0.28534	0.22124	0.03099

(I_2_opt.cif)

Crystal data

?	β = 90.982°
Mr = ?	V = 455.43 Å^3
Monoclinic, P2_1/c	Z = ?
a = 4.9684 Å	? radiation, λ = ? Å
b = 10.0375 Å	× × mm
c = 9.8077 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	−0.04061	0.31655	0.00302
C2	−0.22854	0.34860	0.10251
C3	−0.40578	0.43516	0.19798
C4	−0.52490	0.29889	0.25916
C5	−0.33240	0.22631	0.15934
C6	−0.20468	0.12249	0.09377
O7	−0.02320	0.17713	−0.00337
H8	0.09173	0.36917	−0.06939
H9	−0.29066	0.49562	0.27612
H10	−0.55778	0.49942	0.14366
H11	−0.48453	0.28298	0.37246
H12	−0.74467	0.28395	0.23632
H13	−0.20824	0.01359	0.09613

(II_opt.cif)

Crystal data

?	β = 103.204°
Mr = ?	V = 514.25 Å^3
Monoclinic, P2_1/n	Z = ?
a = 7.2899 Å	? radiation, λ = ? Å
b = 8.7833 Å	× × mm
c = 8.8590 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
S1	−0.35738	−0.41783	−0.16207
C1	−0.30447	−0.59640	−0.08377
H1	−0.35939	−0.69575	−0.15630
C2	−0.19602	−0.59166	0.07423
O1	−0.13085	−0.71280	0.16983
H2	−0.17207	−0.81134	0.11241
C3	−0.15789	−0.44040	0.13219
H3	−0.07891	−0.41264	0.25359
C3	−0.23735	−0.33285	0.01645
C5	−0.23366	−0.17363	0.03157
N1	−0.23288	−0.04048	0.04163

(III_opt.cif)

Crystal data

?	β = 96.479°
Mr = ?	V = 1094.45 Å^3
Monoclinic, P2_1/c	Z = ?
a = 6.8127 Å	? radiation, λ = ? Å
b = 7.4710 Å	× × mm
c = 21.6413 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	−0.29095	0.10388	0.07261
H1	−0.18064	0.02623	0.10181
C2	−0.48075	0.09857	0.08534
H2	−0.59178	0.17596	0.05622
B1	−0.21701	0.21146	0.01998
O1	−0.33271	0.31426	−0.02471
O2	−0.01714	0.21779	0.00976
C11	−0.20160	0.38378	−0.06271
C12	−0.01051	0.32548	−0.04175
C13	0.15226	0.37419	−0.07079
H13	0.30090	0.33045	−0.05374
C14	0.11469	0.48419	−0.12331
H14	0.23742	0.52493	−0.14820
C15	−0.07635	0.54213	−0.14446
H15	−0.09991	0.62709	−0.18548
C16	−0.23953	0.49369	−0.11409
H16	−0.38815	0.53853	−0.13043
C21	−0.55709	0.00010	0.13584
C22	−0.75599	0.02408	0.14581
H22	−0.84720	0.11376	0.11500
C23	−0.83454	−0.06325	0.19435
H23	−0.98816	−0.04132	0.20180
C24	−0.71689	−0.17878	0.23331
H24	−0.77812	−0.24999	0.27064
C25	−0.51963	−0.20576	0.22355
H25	−0.42842	−0.29826	0.25320
C26	−0.44067	−0.11732	0.17555
H26	−0.28788	−0.14259	0.16793

(IV_opt.cif)

Crystal data

?	β = 95.520°
Mr = ?	V = 767.00 Å^3
Monoclinic, P2_1/a	Z = ?
a = 8.3314 Å	? radiation, λ = ? Å
b = 10.6836 Å	× × mm
c = 8.6502 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
N1	0.02139	−0.09105	−0.19413
H2	−0.07503	−0.15293	−0.19814
C3	0.17231	−0.14203	−0.19564
O4	0.18829	−0.25837	−0.20412
C5	0.31122	−0.05152	−0.19097
H6	0.41345	−0.10058	−0.13036
C7	0.27270	0.07144	−0.10973
H8	0.37226	0.13790	−0.11299
H9	0.25509	0.05446	0.01268
C10	0.12285	0.12826	−0.19676
H11	0.08830	0.21560	−0.14066
C12	−0.01525	0.03755	−0.19261
O13	−0.15497	0.07132	−0.19057
C14	0.15234	0.15878	−0.36706
H15	0.23894	0.23662	−0.36073
H16	0.04235	0.19539	−0.43009
C17	0.21526	0.04564	−0.45366
H18	0.11830	−0.02218	−0.48354
H19	0.25388	0.07723	−0.56508
C20	0.35158	−0.02281	−0.35827
H21	0.38166	−0.11096	−0.41570
H22	0.46010	0.03534	−0.34661

(VI_opt.cif)

Crystal data

?	β = 86.157°
Mr = ?	V = 1069.64 Å^3
Monoclinic, P2_1/c	Z = ?
a = 8.8320 Å	? radiation, λ = ? Å
b = 9.2134 Å	× × mm
c = 14.0267 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
H1	−0.0039	−0.0157	0.1941
C2	−0.1621	0.0934	0.1186
C3	−0.0776	−0.1552	0.0925
C4	−0.1685	−0.1676	0.0145
H5	−0.1684	−0.2688	−0.0251
C6	−0.2531	−0.0483	−0.0104
H7	−0.3222	−0.0565	−0.0717
C8	−0.2521	0.0821	0.0404
H9	−0.3191	0.1740	0.0198
C10	−0.4094	0.3627	0.1613
C11	−0.4820	0.4753	0.1156
H12	−0.4153	0.5584	0.0769
C13	−0.6401	0.4783	0.1197
H14	−0.6991	0.5640	0.0837
C15	−0.7234	0.3691	0.1682
H16	−0.8467	0.3700	0.1694
C17	−0.6499	0.2571	0.2137
H18	−0.7152	0.1708	0.2501
C19	−0.4918	0.2538	0.2107
H20	−0.4328	0.1671	0.2456
N21	−0.1467	0.2057	0.1804
N22	−0.0777	−0.0262	0.1401
N23	0.0115	−0.2626	0.1217
H24	−0.0057	−0.3630	0.0938
H25	0.0574	−0.2583	0.1868
O26	−0.1711	0.4532	0.2418
O27	−0.1513	0.4227	0.0658
S28	−0.2074	0.3637	0.1591

(VII_opt.cif)

Crystal data

?	β = 91.033°
Mr = ?	V = 342.66 Å^3
Monoclinic, P2_1/n	Z = ?
a = 4.1832 Å	? radiation, λ = ? Å
b = 12.7487 Å	× × mm
c = 7.0031 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	0.21539	−0.05478	0.22443
H2	−0.04922	−0.05712	0.19162
H3	0.34094	−0.07861	0.08832
H4	0.28146	0.02880	0.25622
C5	0.30727	−0.12883	0.39745
H6	0.17925	−0.10298	0.53182
H7	0.57023	−0.12039	0.43299
C8	0.22961	−0.24644	0.35443
H9	−0.03398	−0.25867	0.32679
H10	0.35762	−0.27428	0.22179
H11	0.30432	−0.29850	0.47853

(VIII_opt.cif)

Crystal data

?	β = 103.129°
Mr = ?	V = 836.67 Å^3
Monoclinic, C2/c	Z = ?
a = 9.8958 Å	? radiation, λ = ? Å
b = 12.7552 Å	× × mm
c = 6.8064 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	0.30211	0.00154	0.31942
N1	0.34787	−0.09596	0.37425
C2	0.26424	−0.17546	0.25115
C3	0.15294	−0.11068	0.11405
N2	0.18063	−0.00840	0.16571
O1	0.35167	0.08704	0.38721
O2	0.05431	−0.14328	−0.01869
H1	0.44054	−0.10723	0.47861
H2	0.21592	−0.23082	0.33779
H3	0.32271	−0.22134	0.16192
H4	0.12369	0.05531	0.09455

(X_opt.cif)

Crystal data

?	β = 98.980°
Mr = ?	V = 1069.64 Å^3
Monoclinic, P2_1/n	Z = ?
a = 12.5087 Å	? radiation, λ = ? Å
b = 4.9545 Å	× × mm
c = 17.4595 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
C1	−0.11774	0.52738	0.17310
C2	−0.07990	0.39962	0.11100
C3	0.00453	0.21446	0.12563
C4	0.05320	0.15552	0.20102
C5	0.01586	0.29194	0.26276
C6	−0.06926	0.47885	0.24835
N7	0.06278	0.23281	0.33894
C8	0.08137	0.41741	0.39804
O9	0.06715	0.66340	0.38653
C10	0.11929	0.30247	0.47698
C11	0.14579	−0.03920	0.21590
N12	−0.11919	0.47467	0.03137
O13	−0.10271	0.31602	−0.02082
O14	−0.16500	0.69701	0.01913
N15	−0.21681	0.69251	0.16307
O16	−0.20976	0.91980	0.19283
O17	−0.30093	0.58895	0.12906
H18	0.07841	0.03350	0.35284
H19	0.03525	0.12329	0.07681
H20	−0.10146	0.57383	0.29580
H21	0.15229	0.09879	0.47477
H22	0.04993	0.29095	0.50859
H23	0.17895	0.43889	0.50903
H24	0.16720	−0.11528	0.16153
H25	0.21705	0.05676	0.24972
H26	0.12512	−0.21170	0.25023

(XI_opt.cif)

Crystal data

?	β = 118.930°
Mr = ?	V = 744.43 Å^3
Monoclinic, P2_1/c	Z = ?
a = 9.8094 Å	? radiation, λ = ? Å
b = 9.0253 Å	× × mm
c = 9.6364 Å

Data collection

h = ?→?	l = ?→?
k = ?→?

Refinement

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Biso*/Beq
N1	−0.37842	0.03127	−0.13986
C1	−0.33541	0.10078	0.01616
C2	−0.25065	0.22508	−0.02299
C3	−0.24901	0.11435	−0.14447
H1	−0.36946	−0.08385	−0.13769
H2	−0.43364	0.13172	0.03489
H3	−0.25346	0.03234	0.11740
H4	−0.32775	0.31969	−0.08160
H5	−0.13888	0.26496	0.07175
H6	−0.27564	0.15748	−0.26132
H7	−0.13900	0.05056	−0.09552
N2	−0.33858	−0.30294	−0.10363
C4	−0.30378	−0.34815	0.05897
C5	−0.12768	−0.34413	0.11140
C6	−0.17797	−0.34770	−0.06690
H8	−0.42664	−0.36474	−0.19315
H9	−0.34722	−0.27185	0.11763
H10	−0.34489	−0.46113	0.06379
H11	−0.07322	−0.23812	0.16664
H12	−0.05538	−0.43579	0.18495
H13	−0.12013	−0.27003	−0.10972
H14	−0.17203	−0.46045	−0.10865