Table 1.

Hydrogen bonds obtained for N3 interacting with SARS-CoV-Mpro and N3 interacting with SARS-CoV-2-Mpro models. d(A$···$H) represents the distance between a hydrogen atom (H) and the acceptor (A), d(A$···$D) the distance between acceptor and donor (D), and $\sphericalangle$A$···$H-D the angle involved in the hydrogen bond. The electron density evaluated at a critical point corresponding to a hydrogen bond is represented by $\rho (\mathrm{BCP})$.

Hydrogen bond	N3 interacting with SARS-CoV-Mpro					N3 interacting with SARS-CoV-2-Mpro
	#	d(A–H)	d(A–D)	$\sphericalangle$A–H-D	$\rho (\mathrm{BCP})$	#	d(A–H)	d(A–D)	$\sphericalangle$A–H-D	$\rho (\mathrm{BCP})$
	X-ray structures
		1.615	2.639	104.5	0.004		1.795	2.803	149.8	0.004
N–H$···$O	7	2.162	3.026	150.7	0.022	8	2.073	3.054	163.1	0.023
		2.763	3.529	173.6	0.054		2.815	3.724	172.7	0.034
		1.516	2.508	113.1	0.001		2.124	2.622	104.3	0.001
C–H$···$O	25	2.563	3.389	134.8	0.013	27	2.740	3.520	131.0	0.007
		3.509	4.346	154.3	0.069		3.339	4.096	168.2	0.024
		2.402	2.868	103.4	0.003		–	–	–	–
C–H$···$C	6	2.671	3.490	136.3	0.010	0	–	–	–	–
		3.158	4.215	162.3	0.016		–	–	–	–
		2.407	3.365	108.0	0.002		2.533	3.310	117.8	0.002
C–H$···$N	5	3.192	3.965	133.0	0.004	8	2.860	3.701	134.9	0.007
		3.461	4.396	168.0	0.014		3.591	4.420	153.2	0.011
		3.576	4.118	112.4	0.002
C–H$···$S	2	3.647	4.416	132.5	0.002	1	2.977	3.949	148.6	0.007
		3.718	4.714	152.5	0.003
N–H$···$N	1	3.211	3.976	133.7	0.002	0	–	–	–	–
		1.918	–	–	0.003		1.554	–	–	0.002
H$···$H	16	2.265	–	–	0.007	15	2.249	–	–	0.007
		2.755	-	–	0.014		2.993	–	–	0.029
	Molecular dynamics structures
		1.820	2.771	120.3	0.003		1.846	2.907	117.1	0.007
N–H$···$O	10	2.169	3.068	153.1	0.020	9	2.147	3.074	157.0	0.018
		3.024	3.646	176.2	0.031		2.650	3.338	170.4	0.029
		2.297	3.076	105.9	0.002		2.389	3.112	110.9	0.001
C–H$···$O	20	2.735	3.530	132.5	0.007	18	2.835	3.665	134.6	0.006
		3.315	4.027	172.8	0.014		3.850	4.764	166.0	0.011
		2.742	3.664	142.0	0.003		2.116	2.939	131.7	0.005
C–H$···$C	4	3.022	4.002	150.2	0.004	4	2.859	3.825	148.1	0.033
		3.112	4.334	159.2	0.006		3.530	4.580	158.1	0.091
		2.496	3.336	116.6	0.002		2.740	3.480	132.9	0.002
C–H$···$N	5	2.940	3.811	139.8	0.006	3	2.862	3.786	143.1	0.006
		3.398	4.338	165.7	0.012		3.303	4.129	153.0	0.010
		2.836	3.498	119.0	0.003
C–H$···$S	3	3.128	3.982	137.4	0.006	1	2.944	4.001	162.8	0.007
		3.479	4.473	151.9	0.009
N–H$···$C	0	–	–	–	–	1	2.981	3.712	130.3	0.004
		2.011	–	–	0.001		1.970	–	–	0.002
H$···$H	10	2.468	–	–	0.005	11	2.326	–	–	0.007
		3.077	–	–	0.011		2.708	–	–	0.011