Supramolecular Arrangement in Styphnic Acid and Naphthalene-1,4-diol (1 : 1) through a Novel Synthetic Rote for Styphnic Acid

Table 2

Selected interatomic distances, angles, and hydrogen bond geometries (Å, °).

(a)  

Bond	Lengths	Bond	Lengths
N1–C1	1.457(4)	C1–C2	1.400(3)
N2–C3	1.466(3)	C1–C2i	1.400(2)
O1–C2	1.342(4)	C2–C3	1.397(3)
O1–H1	0.89(5)	C3–C4	1.375(2)
O2–N1	1.228(3)	C4–H4	1.09(3)
O3–N2	1.183(3)	C5–C5i	1.405(4)
O4–N2	1.212(3)	C5–C6	1.372(3)
O5–C6	1.243(4)	C5–H5	0.94(3)
O5–H5O	0.8400	C6–C7	1.420(3)
C7–C8	1.422(3)	C7–C7i	1.424(3)
	Angles		Angles
N1–C1–C2	118.39(13)	C1–C2–C3	116.3(2)
N2–C3–C2	119.56(18)	C2–C1–C2i	123.2(2)
N2–C3–C4	117.56(18)	C2–C3–C4	122.9(2)
O1–C2–C1	122.9(2)	C3–C4–C3i	118.4(2)
O1–C2–C3	120.8(2)	C5–C6–C7	120.1(2)
O2–N1–C1	118.41(14)	C5i–C5–C6	120.8(2)
O2–N1–O2^i	123.2(3)	C6–C7–C7i	119.19(19)
O3–N2–C3	119.16(19)	C6–C7–C8	122.2(2)
O3–N2–O4	123.2(2)	C7–C8–C9	120.7(2)
O4–N2–C3	117.65(18)	C7i–C7–C8	118.63(19)
O5–C6–C5	127.7(3)	C8–C9–C9i	120.6(2)
O5–C6–C7	112.2(2)	C6–O5–H5O	109

(b)   

D–H⋯ A	D–H	H⋯ A	D ⋯A	D–H⋯ A
O1–H1⋯O2	0.89(6)	1.59(6)	2.454(4)	161(5)
C5–H5⋯O2^ii	0.94(3)	2.69(2)	3.379(3)	131.2(18)
C9–H9⋯O4^iii	0.97(3)	2.94(3)	3.788(3)	146.6(18)
C8–H8⋯O1^iv	0.91(3)	2.68(3)	3.432(5)	141(2)
C9–H9⋯O3^iv	0.96(3)	2.62(3)	3.235(4)	122.2(19)
O5–H5O⋯O4^v	0.84	1.99	2.790(3)	160
C5–H5⋯O3^v	0.94(3)	2.79(3)	3.668(3)	157(2)
O2^i⋯H5⋯O3^v	2.69(2)	2.79(3)	3.051(2)	67.65(18)
O3^iv⋯H9⋯O4^iii	2.62(3)	2.94(3)	3.698(3)	83.14(18)

i: 𝑥,1/2−𝑦,𝑧; ii: 𝑥+1/2, 𝑦, −𝑧+1/2; iii: 𝑥−1/2, 𝑦, −𝑧+1/2; iv: −𝑥,−𝑦+1, −𝑧+1; v: −𝑥+1/2, −𝑦+1, 𝑧+1/2.