Crystal structures of co­crys­tals of 2,7-di­hydroxy­naphthalene with isoniazid and piracetam

Cocrystals of 2,7-di­hydroxy­naphthalene (DHN, or naphthalene-2,7-diol) with isoniazid (pyridine-4-carbohydrazide) (INH), denoted DHN–INH [C₁₀H₈O₂·C₆H₇N₃O, (I)], and piracetam [2-(2-oxopyrrolidin-1-yl)acetamide] (PIR), denoted DHN–PIR [C₁₀H₈O₂·C₆H₁₀N₂O₂, (II)], were obtained by the solvent-assisted grinding method and characterized by IR spectroscopy, powder X-ray diffraction and single-crystal X-ray diffraction. Cocrystal (I) crystallized in the triclinic space group P and showed a 2:2 stoichiometry. DHN and INH mol­ecules are connected by O—H...N(pyridine) and O—H...N(hydrazide) hydrogen bonds. Cocrystal (II) crystallized in the space group Pca2₁ with a 1:1 stoichiometry. DHN and PIR mol­ecules are connected by O—H...O=C hydrogen bonds. The supra­molecular architecture of co­crys­tal (I) showed inter­linked supra­molecular tapes; meanwhile, in co­crys­tal (II), inter­linked supra­molecular sheets were observed.

Computing details

For both structures, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2020) and WinGX (Farrugia, 2012).

Naphthalene-2,7-diol; pyridine-4-carbohydrazide (I)

Crystal data

C10H8O2·C6H7N3O	Z = 4
Mr = 297.31	F(000) = 624
Triclinic, P1	Dx = 1.413 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0118 (8) Å	Cell parameters from 4934 reflections
b = 11.8026 (8) Å	θ = 3.5–29.3°
c = 13.6496 (8) Å	µ = 0.1 mm^−1
α = 65.234 (6)°	T = 130 K
β = 73.354 (6)°	Block, colourless
γ = 78.437 (6)°	0.56 × 0.44 × 0.38 mm
V = 1397.18 (19) Å^3

Data collection

Agilent Xcalibur Atlas Gemini diffractometer	6386 independent reflections
Graphite monochromator	5427 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm^-1	Rint = 0.019
ω scans	θmax = 29.3°, θmin = 3.5°
Absorption correction: analytical [CrysAlis PRO (Agilent, 2013), based on expressions derived by Clark & Reid (1995)]	h = −13→12
Tmin = 0.957, Tmax = 0.969	k = −15→15
10805 measured reflections	l = −18→18

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2) + (0.0673P)^2 + 0.3595P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.114	(Δ/σ)max = 0.001
S = 1.00	Δρmax = 0.38 e Å^−3
6386 reflections	Δρmin = −0.21 e Å^−3
428 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
10 restraints	Extinction coefficient: 0.053 (3)

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
C1	0.85909 (12)	0.65337 (11)	0.34248 (10)	0.0158 (2)
H1	0.843007	0.581924	0.409855	0.019*
C2	0.79430 (12)	0.67174 (11)	0.26016 (10)	0.0167 (2)
C3	0.82044 (13)	0.77631 (12)	0.15795 (10)	0.0190 (3)
H3	0.7763	0.788104	0.100908	0.023*
C4	0.90878 (13)	0.85967 (11)	0.14172 (10)	0.0179 (2)
H4	0.926344	0.928679	0.072629	0.021*
C5	1.05961 (13)	0.93609 (11)	0.21314 (10)	0.0183 (2)
H5	1.078825	1.005451	0.144484	0.022*
C6	1.11405 (13)	0.92533 (11)	0.29809 (11)	0.0191 (3)
H6	1.169353	0.987362	0.288737	0.023*
C7	1.08761 (12)	0.82142 (11)	0.39991 (10)	0.0167 (2)
C8	1.01197 (12)	0.72894 (11)	0.41290 (10)	0.0165 (2)
H8	1.001155	0.656532	0.479804	0.02*
C9	0.94993 (12)	0.74038 (11)	0.32763 (10)	0.0151 (2)
C10	0.97527 (12)	0.84606 (11)	0.22542 (10)	0.0159 (2)
C11	0.55038 (12)	0.09760 (11)	0.10670 (9)	0.0147 (2)
H11	0.605204	0.020569	0.111595	0.018*
C12	0.41890 (12)	0.11823 (11)	0.08631 (9)	0.0154 (2)
C13	0.33621 (13)	0.23297 (11)	0.07820 (10)	0.0183 (2)
H13	0.245625	0.24648	0.063985	0.022*
C14	0.38663 (13)	0.32406 (11)	0.09081 (10)	0.0183 (2)
H14	0.330489	0.400739	0.084937	0.022*
C15	0.57511 (13)	0.39783 (11)	0.12898 (10)	0.0187 (3)
H15	0.519788	0.474488	0.124787	0.022*
C16	0.70477 (14)	0.37836 (11)	0.15076 (10)	0.0199 (3)
H16	0.738247	0.440264	0.162726	0.024*
C17	0.78886 (13)	0.26494 (12)	0.15533 (10)	0.0190 (3)
C18	0.73928 (13)	0.17370 (11)	0.14105 (10)	0.0169 (2)
H18	0.796396	0.097882	0.145067	0.02*
C19	0.60425 (12)	0.19109 (11)	0.12041 (9)	0.0146 (2)
C20	0.52118 (13)	0.30648 (11)	0.11251 (9)	0.0158 (2)
C23	0.49553 (12)	0.22136 (11)	0.53932 (10)	0.0150 (2)
C24	0.40633 (12)	0.15454 (10)	0.51307 (10)	0.0144 (2)
C25	0.31588 (12)	0.07336 (11)	0.60044 (10)	0.0167 (2)
H25	0.306254	0.065277	0.67431	0.02*
C26	0.24003 (12)	0.00445 (11)	0.57819 (10)	0.0180 (2)
H26	0.177026	−0.049511	0.638212	0.022*
C28	0.33882 (13)	0.08871 (12)	0.39223 (10)	0.0198 (3)
H28	0.347465	0.093993	0.319326	0.024*
C29	0.41741 (13)	0.16252 (11)	0.40646 (10)	0.0182 (2)
H29	0.477633	0.21746	0.344672	0.022*
C33	0.68566 (12)	0.39852 (11)	0.74939 (10)	0.0143 (2)
C34	0.78844 (12)	0.45609 (11)	0.77191 (10)	0.0145 (2)
C35	0.82451 (13)	0.57473 (12)	0.69621 (10)	0.0188 (3)
H35	0.786723	0.615468	0.632185	0.023*
C36	0.91612 (13)	0.63267 (12)	0.71534 (11)	0.0216 (3)
H36	0.939712	0.713849	0.663317	0.026*
C38	0.93879 (13)	0.46494 (12)	0.87561 (11)	0.0196 (3)
H38	0.979353	0.425903	0.93827	0.024*
C39	0.84779 (12)	0.40032 (11)	0.86367 (10)	0.0167 (2)
H39	0.826115	0.319262	0.917141	0.02*
N21	0.63005 (12)	0.39774 (10)	0.47160 (10)	0.0199 (2)
H21D	0.7091 (15)	0.3447 (14)	0.4822 (13)	0.024*
H21E	0.5911 (16)	0.4123 (14)	0.5343 (12)	0.024*
N22	0.53751 (11)	0.33089 (10)	0.45870 (9)	0.0196 (2)
H22D	0.4915 (16)	0.3746 (14)	0.4064 (12)	0.023*
N27	0.25129 (11)	0.01028 (10)	0.47587 (9)	0.0185 (2)
N31	0.55710 (12)	0.21912 (10)	0.81158 (9)	0.0190 (2)
H31D	0.4730 (14)	0.2655 (13)	0.8127 (13)	0.023*
H31E	0.5864 (16)	0.2163 (14)	0.7437 (11)	0.023*
N32	0.65133 (11)	0.28479 (10)	0.82285 (9)	0.0186 (2)
H32D	0.6872 (16)	0.2430 (14)	0.8806 (12)	0.022*
N37	0.97298 (11)	0.57959 (10)	0.80373 (9)	0.0210 (2)
O2	0.70331 (10)	0.59490 (9)	0.26843 (8)	0.0215 (2)
H2D	0.6872 (18)	0.5362 (15)	0.3353 (12)	0.032*
O7	1.13672 (9)	0.81026 (8)	0.48735 (7)	0.0203 (2)
H7D	1.1746 (17)	0.8793 (14)	0.4750 (14)	0.03*
O12	0.36090 (9)	0.03287 (8)	0.07237 (7)	0.01899 (19)
H12D	0.4074 (17)	−0.0412 (13)	0.0987 (14)	0.028*
O17	0.92001 (10)	0.24327 (9)	0.17278 (9)	0.0274 (2)
H17D	0.944 (2)	0.3067 (15)	0.1791 (16)	0.041*
O23	0.53165 (10)	0.17543 (8)	0.62746 (7)	0.0214 (2)
O33	0.63473 (10)	0.45498 (8)	0.66773 (8)	0.0247 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0155 (5)	0.0139 (5)	0.0169 (6)	−0.0026 (4)	−0.0035 (4)	−0.0045 (5)
C2	0.0150 (5)	0.0163 (6)	0.0208 (6)	−0.0030 (4)	−0.0035 (4)	−0.0087 (5)
C3	0.0195 (6)	0.0217 (6)	0.0175 (6)	−0.0018 (5)	−0.0063 (5)	−0.0079 (5)
C4	0.0193 (6)	0.0172 (6)	0.0142 (6)	−0.0026 (4)	−0.0026 (4)	−0.0037 (5)
C5	0.0171 (6)	0.0176 (6)	0.0180 (6)	−0.0052 (4)	−0.0014 (4)	−0.0048 (5)
C6	0.0168 (6)	0.0181 (6)	0.0239 (6)	−0.0062 (5)	−0.0027 (5)	−0.0087 (5)
C7	0.0132 (5)	0.0189 (6)	0.0198 (6)	−0.0007 (4)	−0.0044 (4)	−0.0091 (5)
C8	0.0170 (6)	0.0147 (5)	0.0166 (6)	−0.0020 (4)	−0.0044 (4)	−0.0043 (5)
C9	0.0126 (5)	0.0142 (5)	0.0183 (6)	0.0001 (4)	−0.0027 (4)	−0.0070 (5)
C10	0.0130 (5)	0.0165 (5)	0.0175 (6)	−0.0017 (4)	−0.0012 (4)	−0.0071 (5)
C11	0.0181 (6)	0.0127 (5)	0.0132 (5)	−0.0023 (4)	−0.0032 (4)	−0.0049 (4)
C12	0.0191 (6)	0.0170 (5)	0.0105 (5)	−0.0051 (4)	−0.0019 (4)	−0.0050 (4)
C13	0.0170 (6)	0.0216 (6)	0.0159 (6)	−0.0009 (5)	−0.0045 (4)	−0.0068 (5)
C14	0.0206 (6)	0.0165 (6)	0.0156 (6)	0.0012 (5)	−0.0029 (5)	−0.0062 (5)
C15	0.0256 (6)	0.0141 (6)	0.0158 (6)	−0.0023 (5)	−0.0021 (5)	−0.0066 (5)
C16	0.0281 (7)	0.0160 (6)	0.0182 (6)	−0.0081 (5)	−0.0041 (5)	−0.0070 (5)
C17	0.0222 (6)	0.0181 (6)	0.0166 (6)	−0.0054 (5)	−0.0062 (5)	−0.0039 (5)
C18	0.0197 (6)	0.0145 (5)	0.0171 (6)	−0.0017 (4)	−0.0063 (5)	−0.0052 (5)
C19	0.0193 (6)	0.0140 (5)	0.0096 (5)	−0.0035 (4)	−0.0031 (4)	−0.0030 (4)
C20	0.0208 (6)	0.0141 (5)	0.0112 (5)	−0.0024 (4)	−0.0029 (4)	−0.0036 (4)
C23	0.0161 (5)	0.0138 (5)	0.0157 (6)	0.0003 (4)	−0.0041 (4)	−0.0066 (5)
C24	0.0154 (5)	0.0116 (5)	0.0168 (6)	0.0009 (4)	−0.0058 (4)	−0.0057 (4)
C25	0.0181 (6)	0.0171 (6)	0.0146 (6)	−0.0013 (4)	−0.0034 (4)	−0.0062 (5)
C26	0.0153 (6)	0.0183 (6)	0.0189 (6)	−0.0030 (4)	−0.0023 (4)	−0.0060 (5)
C28	0.0245 (6)	0.0207 (6)	0.0164 (6)	−0.0039 (5)	−0.0065 (5)	−0.0074 (5)
C29	0.0216 (6)	0.0172 (6)	0.0147 (6)	−0.0045 (5)	−0.0037 (5)	−0.0043 (5)
C33	0.0142 (5)	0.0144 (5)	0.0159 (6)	−0.0008 (4)	−0.0029 (4)	−0.0079 (5)
C34	0.0125 (5)	0.0165 (5)	0.0158 (6)	−0.0011 (4)	−0.0016 (4)	−0.0085 (5)
C35	0.0195 (6)	0.0192 (6)	0.0169 (6)	−0.0031 (5)	−0.0046 (5)	−0.0053 (5)
C36	0.0218 (6)	0.0190 (6)	0.0230 (6)	−0.0071 (5)	−0.0027 (5)	−0.0064 (5)
C38	0.0173 (6)	0.0229 (6)	0.0220 (6)	−0.0006 (5)	−0.0073 (5)	−0.0104 (5)
C39	0.0173 (6)	0.0162 (6)	0.0173 (6)	−0.0020 (4)	−0.0043 (4)	−0.0066 (5)
N21	0.0236 (6)	0.0162 (5)	0.0241 (6)	−0.0063 (4)	−0.0107 (4)	−0.0063 (4)
N22	0.0246 (5)	0.0150 (5)	0.0210 (6)	−0.0067 (4)	−0.0129 (4)	−0.0015 (4)
N27	0.0180 (5)	0.0182 (5)	0.0217 (5)	−0.0020 (4)	−0.0071 (4)	−0.0083 (4)
N31	0.0214 (5)	0.0198 (5)	0.0205 (6)	−0.0074 (4)	−0.0076 (4)	−0.0079 (4)
N32	0.0229 (5)	0.0174 (5)	0.0183 (5)	−0.0076 (4)	−0.0107 (4)	−0.0032 (4)
N37	0.0174 (5)	0.0232 (5)	0.0265 (6)	−0.0049 (4)	−0.0042 (4)	−0.0126 (5)
O2	0.0240 (5)	0.0212 (5)	0.0220 (5)	−0.0091 (4)	−0.0088 (4)	−0.0053 (4)
O7	0.0226 (4)	0.0211 (4)	0.0209 (5)	−0.0078 (3)	−0.0087 (4)	−0.0066 (4)
O12	0.0189 (4)	0.0197 (4)	0.0218 (5)	−0.0049 (3)	−0.0054 (3)	−0.0094 (4)
O17	0.0261 (5)	0.0225 (5)	0.0422 (6)	−0.0036 (4)	−0.0175 (4)	−0.0136 (4)
O23	0.0289 (5)	0.0214 (4)	0.0164 (4)	−0.0066 (4)	−0.0089 (4)	−0.0055 (4)
O33	0.0331 (5)	0.0196 (5)	0.0238 (5)	−0.0055 (4)	−0.0176 (4)	−0.0021 (4)

Geometric parameters (Å, º)

C1—C2	1.3739 (17)	C23—O23	1.2232 (15)
C1—C9	1.4203 (16)	C23—N22	1.3490 (15)
C1—H1	0.95	C23—C24	1.5001 (16)
C2—O2	1.3607 (14)	C24—C25	1.3899 (17)
C2—C3	1.4198 (17)	C24—C29	1.3913 (17)
C3—C4	1.3614 (17)	C25—C26	1.3846 (17)
C3—H3	0.95	C25—H25	0.95
C4—C10	1.4190 (17)	C26—N27	1.3418 (16)
C4—H4	0.95	C26—H26	0.95
C5—C6	1.3670 (18)	C28—N27	1.3397 (16)
C5—C10	1.4141 (16)	C28—C29	1.3855 (17)
C5—H5	0.95	C28—H28	0.95
C6—C7	1.4132 (17)	C29—H29	0.95
C6—H6	0.95	C33—O33	1.2303 (14)
C7—O7	1.3647 (15)	C33—N32	1.3361 (15)
C7—C8	1.3742 (16)	C33—C34	1.5004 (16)
C8—C9	1.4170 (17)	C34—C39	1.3907 (17)
C8—H8	0.95	C34—C35	1.3913 (17)
C9—C10	1.4257 (17)	C35—C36	1.3840 (17)
C11—C12	1.3763 (16)	C35—H35	0.95
C11—C19	1.4188 (16)	C36—N37	1.3377 (17)
C11—H11	0.95	C36—H36	0.95
C12—O12	1.3590 (14)	C38—N37	1.3386 (17)
C12—C13	1.4174 (17)	C38—C39	1.3807 (17)
C13—C14	1.3648 (17)	C38—H38	0.95
C13—H13	0.95	C39—H39	0.95
C14—C20	1.4179 (17)	N21—N22	1.4194 (14)
C14—H14	0.95	N21—H21D	0.911 (13)
C15—C16	1.3676 (18)	N21—H21E	0.905 (13)
C15—C20	1.4179 (16)	N22—H22D	0.879 (13)
C15—H15	0.95	N31—N32	1.4108 (14)
C16—C17	1.4188 (18)	N31—H31D	0.908 (13)
C16—H16	0.95	N31—H31E	0.901 (13)
C17—O17	1.3564 (15)	N32—H32D	0.871 (13)
C17—C18	1.3745 (17)	O2—H2D	0.878 (14)
C18—C19	1.4169 (16)	O7—H7D	0.899 (13)
C18—H18	0.95	O12—H12D	0.883 (13)
C19—C20	1.4256 (16)	O17—H17D	0.875 (14)
C2—C1—C9	120.50 (11)	C14—C20—C15	122.68 (11)
C2—C1—H1	119.8	C14—C20—C19	118.56 (11)
C9—C1—H1	119.8	C15—C20—C19	118.74 (11)
O2—C2—C1	124.36 (11)	O23—C23—N22	122.74 (11)
O2—C2—C3	115.35 (10)	O23—C23—C24	121.09 (10)
C1—C2—C3	120.29 (11)	N22—C23—C24	116.11 (10)
C4—C3—C2	119.97 (11)	C25—C24—C29	118.34 (11)
C4—C3—H3	120	C25—C24—C23	118.33 (10)
C2—C3—H3	120	C29—C24—C23	123.15 (11)
C3—C4—C10	121.64 (11)	C26—C25—C24	119.01 (11)
C3—C4—H4	119.2	C26—C25—H25	120.5
C10—C4—H4	119.2	C24—C25—H25	120.5
C6—C5—C10	121.32 (11)	N27—C26—C25	123.11 (11)
C6—C5—H5	119.3	N27—C26—H26	118.4
C10—C5—H5	119.3	C25—C26—H26	118.4
C5—C6—C7	119.63 (11)	N27—C28—C29	123.46 (11)
C5—C6—H6	120.2	N27—C28—H28	118.3
C7—C6—H6	120.2	C29—C28—H28	118.3
O7—C7—C8	118.47 (11)	C28—C29—C24	118.65 (11)
O7—C7—C6	120.94 (10)	C28—C29—H29	120.7
C8—C7—C6	120.59 (11)	C24—C29—H29	120.7
C7—C8—C9	120.73 (11)	O33—C33—N32	122.18 (11)
C7—C8—H8	119.6	O33—C33—C34	121.02 (10)
C9—C8—H8	119.6	N32—C33—C34	116.79 (10)
C8—C9—C1	122.21 (11)	C39—C34—C35	118.01 (11)
C8—C9—C10	118.46 (10)	C39—C34—C33	124.69 (10)
C1—C9—C10	119.27 (11)	C35—C34—C33	117.29 (10)
C5—C10—C4	122.52 (11)	C36—C35—C34	119.18 (11)
C5—C10—C9	119.10 (11)	C36—C35—H35	120.4
C4—C10—C9	118.30 (10)	C34—C35—H35	120.4
C12—C11—C19	120.17 (11)	N37—C36—C35	122.99 (11)
C12—C11—H11	119.9	N37—C36—H36	118.5
C19—C11—H11	119.9	C35—C36—H36	118.5
O12—C12—C11	123.25 (11)	N37—C38—C39	123.58 (11)
O12—C12—C13	116.21 (10)	N37—C38—H38	118.2
C11—C12—C13	120.53 (11)	C39—C38—H38	118.2
C14—C13—C12	120.05 (11)	C38—C39—C34	118.77 (11)
C14—C13—H13	120	C38—C39—H39	120.6
C12—C13—H13	120	C34—C39—H39	120.6
C13—C14—C20	121.29 (11)	N22—N21—H21D	105.9 (10)
C13—C14—H14	119.4	N22—N21—H21E	108.0 (10)
C20—C14—H14	119.4	H21D—N21—H21E	107.8 (14)
C16—C15—C20	121.66 (11)	C23—N22—N21	120.88 (10)
C16—C15—H15	119.2	C23—N22—H22D	121.4 (10)
C20—C15—H15	119.2	N21—N22—H22D	115.3 (10)
C15—C16—C17	119.46 (11)	C28—N27—C26	117.43 (10)
C15—C16—H16	120.3	N32—N31—H31D	107.6 (10)
C17—C16—H16	120.3	N32—N31—H31E	108.0 (10)
O17—C17—C18	117.97 (11)	H31D—N31—H31E	106.3 (14)
O17—C17—C16	121.58 (11)	C33—N32—N31	122.86 (10)
C18—C17—C16	120.44 (11)	C33—N32—H32D	123.5 (10)
C17—C18—C19	120.97 (11)	N31—N32—H32D	113.6 (10)
C17—C18—H18	119.5	C36—N37—C38	117.46 (11)
C19—C18—H18	119.5	C2—O2—H2D	110.1 (11)
C18—C19—C11	121.90 (11)	C7—O7—H7D	112.6 (11)
C18—C19—C20	118.70 (11)	C12—O12—H12D	108.6 (11)
C11—C19—C20	119.40 (11)	C17—O17—H17D	112.1 (12)
C9—C1—C2—O2	−178.35 (11)	C13—C14—C20—C15	−178.26 (11)
C9—C1—C2—C3	1.72 (18)	C13—C14—C20—C19	0.35 (17)
O2—C2—C3—C4	179.30 (11)	C16—C15—C20—C14	179.42 (11)
C1—C2—C3—C4	−0.77 (18)	C16—C15—C20—C19	0.82 (18)
C2—C3—C4—C10	−0.79 (19)	C18—C19—C20—C14	179.41 (11)
C10—C5—C6—C7	0.94 (18)	C11—C19—C20—C14	−0.13 (16)
C5—C6—C7—O7	−177.84 (11)	C18—C19—C20—C15	−1.92 (16)
C5—C6—C7—C8	2.35 (18)	C11—C19—C20—C15	178.54 (10)
O7—C7—C8—C9	175.35 (10)	O23—C23—C24—C25	28.16 (17)
C6—C7—C8—C9	−4.83 (18)	N22—C23—C24—C25	−154.60 (11)
C7—C8—C9—C1	−173.24 (11)	O23—C23—C24—C29	−146.79 (12)
C7—C8—C9—C10	3.98 (17)	N22—C23—C24—C29	30.45 (17)
C2—C1—C9—C8	176.07 (11)	C29—C24—C25—C26	−0.38 (17)
C2—C1—C9—C10	−1.12 (17)	C23—C24—C25—C26	−175.57 (10)
C6—C5—C10—C4	175.12 (12)	C24—C25—C26—N27	1.28 (18)
C6—C5—C10—C9	−1.69 (18)	N27—C28—C29—C24	0.56 (19)
C3—C4—C10—C5	−175.49 (12)	C25—C24—C29—C28	−0.48 (17)
C3—C4—C10—C9	1.35 (18)	C23—C24—C29—C28	174.47 (11)
C8—C9—C10—C5	−0.73 (17)	O33—C33—C34—C39	178.10 (12)
C1—C9—C10—C5	176.57 (11)	N32—C33—C34—C39	−0.95 (17)
C8—C9—C10—C4	−177.69 (11)	O33—C33—C34—C35	−0.69 (17)
C1—C9—C10—C4	−0.39 (17)	N32—C33—C34—C35	−179.74 (11)
C19—C11—C12—O12	−179.99 (10)	C39—C34—C35—C36	−0.57 (18)
C19—C11—C12—C13	0.33 (17)	C33—C34—C35—C36	178.31 (11)
O12—C12—C13—C14	−179.81 (10)	C34—C35—C36—N37	0.30 (19)
C11—C12—C13—C14	−0.11 (18)	N37—C38—C39—C34	0.43 (19)
C12—C13—C14—C20	−0.24 (18)	C35—C34—C39—C38	0.22 (17)
C20—C15—C16—C17	1.03 (19)	C33—C34—C39—C38	−178.56 (11)
C15—C16—C17—O17	177.65 (12)	O23—C23—N22—N21	1.55 (19)
C15—C16—C17—C18	−1.77 (18)	C24—C23—N22—N21	−175.64 (10)
O17—C17—C18—C19	−178.81 (11)	C29—C28—N27—C26	0.26 (18)
C16—C17—C18—C19	0.63 (18)	C25—C26—N27—C28	−1.20 (18)
C17—C18—C19—C11	−179.26 (11)	O33—C33—N32—N31	1.58 (19)
C17—C18—C19—C20	1.22 (17)	C34—C33—N32—N31	−179.39 (10)
C12—C11—C19—C18	−179.73 (11)	C35—C36—N37—C38	0.33 (19)
C12—C11—C19—C20	−0.21 (17)	C39—C38—N37—C36	−0.70 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2D···N21^i	0.88 (1)	1.92 (1)	2.784 (1)	170 (1)
O7—H7D···N27^ii	0.90 (1)	1.86 (1)	2.754 (2)	170 (1)
O12—H12D···N31^iii	0.88 (1)	1.96 (1)	2.801 (1)	160 (1)
O17—H17D···N37^iv	0.87 (2)	1.84 (2)	2.697 (2)	169 (2)
N21—H21D···O7^iv	0.91 (1)	2.12 (1)	3.015 (1)	167 (1)
N21—H21E···O33^i	0.91 (1)	2.25 (1)	3.037 (2)	145 (1)
N22—H22D···O33	0.88 (1)	2.16 (1)	2.939 (1)	147 (1)
N31—H31D···O2^i	0.91 (1)	2.34 (1)	3.183 (1)	154 (1)
N31—H31E···O23^i	0.90 (2)	2.07 (2)	2.855 (2)	145 (1)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+1; (iii) x, y−1, z; (iv) x+1, y, z.

Naphthalene-2,7-diol; 2-(2-oxopyrrolidin-1-yl)acetamide (II)

Crystal data

C10H8O2·C6H10N2O2	F(000) = 640
Mr = 302.32	Dx = 1.381 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 6581 reflections
a = 13.6888 (8) Å	θ = 4.5–29.1°
b = 11.0370 (6) Å	µ = 0.1 mm^−1
c = 9.6269 (5) Å	T = 130 K
V = 1454.46 (14) Å^3	Prism, colourless
Z = 4	0.55 × 0.4 × 0.23 mm

Data collection

Agilent Xcalibur Atlas Gemini diffractometer	3665 independent reflections
Graphite monochromator	3276 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm^-1	Rint = 0.044
ω scans	θmax = 29.5°, θmin = 3.5°
Absorption correction: analytical [CrysAlis PRO (Agilent, 2013), based on expressions derived by Clark & Reid (1995)]	h = −17→17
Tmin = 0.966, Tmax = 0.98	k = −15→14
18467 measured reflections	l = −12→13

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0343P)^2 + 0.2565P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.082	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.20 e Å^−3
3665 reflections	Δρmin = −0.19 e Å^−3
211 parameters	Absolute structure: Flack x determined using 1333 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
5 restraints	Absolute structure parameter: −0.3 (5)

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
C1	0.61096 (15)	1.00794 (18)	0.30552 (19)	0.0193 (4)
H1	0.556956	1.060957	0.317685	0.023*
C2	0.68607 (15)	1.03945 (18)	0.2173 (2)	0.0206 (4)
C3	0.76736 (16)	0.96208 (19)	0.1981 (2)	0.0242 (5)
H3	0.818877	0.985208	0.137478	0.029*
C4	0.77146 (16)	0.85429 (19)	0.2668 (2)	0.0237 (4)
H4	0.826471	0.803046	0.253848	0.028*
C5	0.69822 (16)	0.70453 (19)	0.4264 (2)	0.0221 (4)
H5	0.751282	0.650955	0.409945	0.027*
C6	0.62618 (15)	0.67080 (18)	0.5170 (2)	0.0207 (4)
H6	0.628897	0.594577	0.562669	0.025*
C7	0.54749 (15)	0.75128 (19)	0.5415 (2)	0.0196 (4)
C8	0.54042 (15)	0.85971 (18)	0.4731 (2)	0.0186 (4)
H8	0.485803	0.91097	0.489023	0.022*
C9	0.61446 (14)	0.89580 (18)	0.3784 (2)	0.0173 (4)
C10	0.69557 (15)	0.81700 (18)	0.3569 (2)	0.0195 (4)
C12	0.26117 (15)	0.61573 (17)	0.2630 (2)	0.0174 (4)
C13	0.35342 (15)	0.67544 (19)	0.3215 (2)	0.0206 (4)
H13A	0.33736	0.758476	0.352938	0.025*
H13B	0.37613	0.628893	0.403211	0.025*
C15	0.49265 (14)	0.59022 (18)	0.1972 (2)	0.0179 (4)
C16	0.56161 (17)	0.6229 (2)	0.0820 (2)	0.0247 (5)
H16A	0.551507	0.569408	0.000663	0.03*
H16B	0.630278	0.615411	0.113105	0.03*
C17	0.53752 (18)	0.7540 (2)	0.0456 (3)	0.0285 (5)
H17A	0.526982	0.762831	−0.055629	0.034*
H17B	0.591395	0.808418	0.074063	0.034*
C18	0.44351 (15)	0.78437 (18)	0.1260 (2)	0.0222 (4)
H18A	0.450799	0.861024	0.178349	0.027*
H18B	0.387092	0.791642	0.062161	0.027*
N11	0.18955 (13)	0.60268 (17)	0.35590 (18)	0.0211 (4)
H11E	0.1374 (16)	0.558 (2)	0.327 (2)	0.025*
H11D	0.2017 (18)	0.614 (2)	0.447 (2)	0.025*
N14	0.43120 (13)	0.68142 (15)	0.22042 (18)	0.0191 (4)
O2	0.68941 (12)	1.14487 (13)	0.14322 (17)	0.0261 (3)
H2D	0.6362 (17)	1.187 (2)	0.157 (3)	0.039*
O7	0.47739 (11)	0.72152 (14)	0.63771 (17)	0.0248 (3)
H7D	0.485 (2)	0.650 (2)	0.673 (3)	0.037*
O12	0.25467 (11)	0.58387 (13)	0.14121 (16)	0.0227 (3)
O15	0.49125 (11)	0.49224 (13)	0.26262 (16)	0.0221 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0185 (10)	0.0185 (9)	0.0210 (10)	0.0021 (7)	−0.0008 (8)	−0.0030 (8)
C2	0.0230 (11)	0.0187 (10)	0.0202 (10)	−0.0021 (8)	−0.0023 (9)	−0.0036 (8)
C3	0.0196 (11)	0.0261 (11)	0.0269 (10)	−0.0026 (8)	0.0059 (9)	−0.0055 (9)
C4	0.0201 (11)	0.0240 (10)	0.0270 (11)	0.0027 (8)	0.0031 (9)	−0.0069 (9)
C5	0.0223 (11)	0.0213 (10)	0.0227 (10)	0.0051 (8)	−0.0019 (9)	−0.0036 (8)
C6	0.0238 (11)	0.0166 (9)	0.0218 (10)	0.0024 (8)	−0.0043 (9)	0.0004 (8)
C7	0.0188 (10)	0.0216 (10)	0.0184 (10)	−0.0012 (8)	−0.0028 (8)	−0.0019 (8)
C8	0.0157 (10)	0.0193 (10)	0.0209 (10)	0.0018 (8)	−0.0008 (8)	−0.0030 (8)
C9	0.0168 (10)	0.0173 (9)	0.0177 (10)	−0.0009 (7)	−0.0024 (8)	−0.0051 (8)
C10	0.0203 (11)	0.0191 (9)	0.0190 (10)	0.0009 (8)	−0.0021 (8)	−0.0051 (8)
C12	0.0206 (10)	0.0147 (8)	0.0170 (9)	0.0015 (7)	−0.0014 (8)	0.0006 (8)
C13	0.0174 (10)	0.0252 (10)	0.0191 (10)	0.0014 (8)	−0.0006 (8)	−0.0032 (8)
C15	0.0167 (10)	0.0211 (9)	0.0159 (9)	0.0006 (8)	−0.0053 (8)	−0.0038 (8)
C16	0.0202 (12)	0.0318 (12)	0.0221 (11)	0.0047 (9)	0.0029 (8)	0.0016 (9)
C17	0.0286 (12)	0.0282 (11)	0.0287 (12)	−0.0003 (10)	0.0060 (10)	0.0041 (10)
C18	0.0222 (10)	0.0199 (10)	0.0246 (11)	0.0010 (8)	−0.0034 (9)	0.0025 (9)
N11	0.0214 (10)	0.0269 (9)	0.0150 (9)	−0.0043 (7)	−0.0011 (7)	−0.0002 (7)
N14	0.0185 (9)	0.0185 (8)	0.0202 (9)	0.0016 (6)	0.0000 (7)	−0.0003 (7)
O2	0.0250 (8)	0.0206 (7)	0.0329 (8)	0.0007 (6)	0.0057 (7)	0.0029 (7)
O7	0.0244 (8)	0.0220 (7)	0.0281 (8)	0.0028 (6)	0.0060 (7)	0.0058 (7)
O12	0.0265 (8)	0.0257 (7)	0.0159 (7)	−0.0021 (6)	0.0007 (6)	−0.0019 (6)
O15	0.0259 (8)	0.0199 (7)	0.0206 (7)	0.0028 (6)	−0.0024 (6)	−0.0003 (6)

Geometric parameters (Å, º)

C1—C2	1.378 (3)	C12—C13	1.531 (3)
C1—C9	1.423 (3)	C13—N14	1.444 (3)
C1—H1	0.95	C13—H13A	0.99
C2—O2	1.366 (2)	C13—H13B	0.99
C2—C3	1.415 (3)	C15—O15	1.252 (3)
C3—C4	1.362 (3)	C15—N14	1.331 (3)
C3—H3	0.95	C15—C16	1.500 (3)
C4—C10	1.415 (3)	C16—C17	1.525 (3)
C4—H4	0.95	C16—H16A	0.99
C5—C6	1.368 (3)	C16—H16B	0.99
C5—C10	1.411 (3)	C17—C18	1.539 (3)
C5—H5	0.95	C17—H17A	0.99
C6—C7	1.416 (3)	C17—H17B	0.99
C6—H6	0.95	C18—N14	1.465 (3)
C7—C8	1.370 (3)	C18—H18A	0.99
C7—O7	1.373 (3)	C18—H18B	0.99
C8—C9	1.420 (3)	N11—H11E	0.91 (2)
C8—H8	0.95	N11—H11D	0.90 (2)
C9—C10	1.425 (3)	O2—H2D	0.88 (2)
C12—O12	1.227 (3)	O7—H7D	0.86 (2)
C12—N11	1.335 (3)
C2—C1—C9	119.86 (18)	N14—C13—H13A	109.1
C2—C1—H1	120.1	C12—C13—H13A	109.1
C9—C1—H1	120.1	N14—C13—H13B	109.1
O2—C2—C1	124.19 (18)	C12—C13—H13B	109.1
O2—C2—C3	114.80 (18)	H13A—C13—H13B	107.9
C1—C2—C3	121.01 (19)	O15—C15—N14	124.0 (2)
C4—C3—C2	119.72 (19)	O15—C15—C16	126.09 (18)
C4—C3—H3	120.1	N14—C15—C16	109.89 (18)
C2—C3—H3	120.1	C15—C16—C17	105.17 (18)
C3—C4—C10	121.44 (19)	C15—C16—H16A	110.7
C3—C4—H4	119.3	C17—C16—H16A	110.7
C10—C4—H4	119.3	C15—C16—H16B	110.7
C6—C5—C10	121.56 (19)	C17—C16—H16B	110.7
C6—C5—H5	119.2	H16A—C16—H16B	108.8
C10—C5—H5	119.2	C16—C17—C18	105.80 (18)
C5—C6—C7	118.95 (19)	C16—C17—H17A	110.6
C5—C6—H6	120.5	C18—C17—H17A	110.6
C7—C6—H6	120.5	C16—C17—H17B	110.6
C8—C7—O7	118.95 (18)	C18—C17—H17B	110.6
C8—C7—C6	121.43 (19)	H17A—C17—H17B	108.7
O7—C7—C6	119.61 (19)	N14—C18—C17	103.83 (16)
C7—C8—C9	120.23 (18)	N14—C18—H18A	111
C7—C8—H8	119.9	C17—C18—H18A	111
C9—C8—H8	119.9	N14—C18—H18B	111
C8—C9—C1	122.42 (18)	C17—C18—H18B	111
C8—C9—C10	118.54 (18)	H18A—C18—H18B	109
C1—C9—C10	119.04 (18)	C12—N11—H11E	115.6 (16)
C5—C10—C4	121.88 (19)	C12—N11—H11D	120.1 (16)
C5—C10—C9	119.22 (19)	H11E—N11—H11D	121 (2)
C4—C10—C9	118.90 (18)	C15—N14—C13	123.01 (18)
O12—C12—N11	123.8 (2)	C15—N14—C18	114.19 (17)
O12—C12—C13	122.28 (19)	C13—N14—C18	122.58 (17)
N11—C12—C13	113.95 (18)	C2—O2—H2D	110.4 (18)
N14—C13—C12	112.35 (17)	C7—O7—H7D	113.4 (18)
C9—C1—C2—O2	−179.89 (18)	C8—C9—C10—C5	2.1 (3)
C9—C1—C2—C3	−0.2 (3)	C1—C9—C10—C5	−178.54 (18)
O2—C2—C3—C4	−179.8 (2)	C8—C9—C10—C4	−177.63 (19)
C1—C2—C3—C4	0.5 (3)	C1—C9—C10—C4	1.7 (3)
C2—C3—C4—C10	0.4 (3)	O12—C12—C13—N14	−3.9 (3)
C10—C5—C6—C7	−0.3 (3)	N11—C12—C13—N14	176.52 (17)
C5—C6—C7—C8	2.3 (3)	O15—C15—C16—C17	−176.1 (2)
C5—C6—C7—O7	−176.52 (19)	N14—C15—C16—C17	4.4 (2)
O7—C7—C8—C9	176.74 (18)	C15—C16—C17—C18	−9.2 (2)
C6—C7—C8—C9	−2.1 (3)	C16—C17—C18—N14	10.4 (2)
C7—C8—C9—C1	−179.47 (19)	O15—C15—N14—C13	−2.2 (3)
C7—C8—C9—C10	−0.1 (3)	C16—C15—N14—C13	177.40 (18)
C2—C1—C9—C8	178.48 (18)	O15—C15—N14—C18	−176.89 (18)
C2—C1—C9—C10	−0.9 (3)	C16—C15—N14—C18	2.7 (2)
C6—C5—C10—C4	177.8 (2)	C12—C13—N14—C15	−84.6 (2)
C6—C5—C10—C9	−1.9 (3)	C12—C13—N14—C18	89.7 (2)
C3—C4—C10—C5	178.7 (2)	C17—C18—N14—C15	−8.4 (2)
C3—C4—C10—C9	−1.5 (3)	C17—C18—N14—C13	176.82 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2D···O7^i	0.87 (2)	1.86 (2)	2.719 (2)	166 (3)
O2—H2D···O15^ii	0.87 (2)	1.82 (2)	2.683 (2)	174 (2)
O7—H7D···O15^ii	0.87 (2)	1.82 (2)	2.683 (2)	174 (2)
N11—H11D···O12^ii	0.90 (2)	1.99 (2)	2.858 (2)	161 (2)
N11—H11E···O15^iii	0.91 (2)	2.17 (2)	3.045 (2)	162 (2)

Symmetry codes: (i) −x, −y, z−1/2; (ii) −x+1/2, y, z+1/2; (iii) x−1/2, −y+1, z.