The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmeth­yl)ethanedi­amide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study

Tan, S.L.; Tiekink, E.R.T.

doi:10.1107/S2056989019016840

The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study

The 4-pyridyl residues lie to either side of the central, planar C₂N₂O₂ chromophore of the oxalamide molecule which has a + anti-periplanar conformation. Conventional hydrogen-bonding interactions lead to supramolecular tapes in the crystal.

Keywords: crystal structure; oxalamide; hydrogen bonding; Hirshfeld surface analysis; computational chemistry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019016840/hb7875sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019016840/hb7875Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019016840/hb7875Isup3.cml Supplementary material

CCDC reference: 1972449

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.034
wR factor = 0.093
Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C7       - C8       .       1.54 Ang.

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         30 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         16 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   6 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXS (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

N,N'-bis(pyridin-4-ylmethyl)ethanediamide; bis(benzoic acid) top

Crystal data top

C₁₄H₁₄N₄O₂·2C₇H₆O₂	Z = 2
M_r = 514.53	F(000) = 540
Triclinic, P1	D_x = 1.369 Mg m⁻³
a = 9.6543 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.9235 (2) Å	Cell parameters from 16947 reflections
c = 14.1670 (3) Å	θ = 3.3–76.2°
α = 100.755 (2)°	µ = 0.81 mm⁻¹
β = 108.318 (2)°	T = 100 K
γ = 95.617 (2)°	Prism, colourless
V = 1247.90 (5) Å³	0.12 × 0.07 × 0.05 mm

Data collection top

Rigaku XtaLAB Synergy Dualflex AtlasS2 diffractometer	5220 independent reflections
Radiation source: micro-focus sealed X-ray tube	4736 reflections with I > 2σ(I)
Detector resolution: 5.2558 pixels mm^-1	R_int = 0.031
ω scans	θ_max = 76.4°, θ_min = 3.4°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018)	h = −12→12
T_min = 0.832, T_max = 1.000	k = −12→12
31534 measured reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: mixed
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0539P)² + 0.3396P] where P = (F_o² + 2F_c²)/3
5220 reflections	(Δ/σ)_max = 0.001
359 parameters	Δρ_max = 0.21 e Å⁻³
4 restraints	Δρ_min = −0.28 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.11169 (8)	0.35585 (8)	0.52445 (6)	0.02229 (17)
O2	0.49733 (8)	0.39415 (8)	0.58292 (6)	0.02091 (16)
N1	−0.09947 (10)	0.21060 (9)	0.09622 (7)	0.02157 (19)
N2	0.25702 (9)	0.46333 (9)	0.45149 (6)	0.01791 (18)
H2N	0.3484 (10)	0.4904 (14)	0.4548 (10)	0.024 (3)*
N3	0.35581 (9)	0.31253 (9)	0.66765 (6)	0.01757 (18)
H3N	0.2664 (11)	0.2971 (14)	0.6716 (11)	0.025 (3)*
N4	0.75967 (10)	0.62970 (10)	0.97336 (7)	0.0225 (2)
C1	−0.14959 (11)	0.32758 (11)	0.12456 (8)	0.0211 (2)
H1	−0.240536	0.343746	0.080891	0.025*
C2	−0.07474 (11)	0.42577 (11)	0.21457 (8)	0.0198 (2)
H2	−0.113267	0.507935	0.231404	0.024*
C3	0.05805 (11)	0.40266 (11)	0.28035 (8)	0.0178 (2)
C4	0.11019 (11)	0.28206 (11)	0.25088 (8)	0.0209 (2)
H4	0.200412	0.262855	0.293315	0.025*
C5	0.02905 (12)	0.18954 (11)	0.15858 (8)	0.0226 (2)
H5	0.066421	0.107775	0.138881	0.027*
C6	0.13776 (11)	0.50952 (11)	0.37960 (8)	0.0190 (2)
H6A	0.178912	0.594422	0.363694	0.023*
H6B	0.064816	0.535030	0.412815	0.023*
C7	0.23279 (11)	0.39410 (10)	0.51848 (7)	0.0168 (2)
C8	0.37639 (11)	0.36670 (10)	0.59305 (7)	0.0165 (2)
C9	0.47933 (11)	0.27763 (11)	0.74404 (8)	0.0198 (2)
H9A	0.539689	0.227162	0.709171	0.024*
H9B	0.439995	0.214321	0.779400	0.024*
C10	0.57768 (11)	0.40374 (10)	0.82273 (7)	0.0179 (2)
C11	0.51872 (12)	0.50271 (12)	0.87410 (9)	0.0261 (2)
H11	0.414595	0.494664	0.858090	0.031*
C12	0.61289 (13)	0.61374 (12)	0.94915 (9)	0.0274 (2)
H12	0.571438	0.680499	0.984407	0.033*
C13	0.81637 (12)	0.53568 (12)	0.92284 (8)	0.0242 (2)
H13	0.920690	0.547791	0.938956	0.029*
C14	0.73011 (12)	0.42117 (12)	0.84793 (8)	0.0224 (2)
H14	0.774771	0.355655	0.814404	0.027*
O3	0.55315 (9)	1.14822 (8)	0.95498 (6)	0.02525 (18)
O4	0.72142 (9)	1.01211 (8)	0.94323 (6)	0.02496 (18)
H4O	0.778 (2)	1.0790 (17)	0.9921 (12)	0.073 (6)*
C15	0.58610 (11)	1.04164 (11)	0.91631 (8)	0.0187 (2)
C16	0.47533 (12)	0.93433 (11)	0.82989 (8)	0.0190 (2)
C17	0.32865 (12)	0.95458 (11)	0.79630 (8)	0.0212 (2)
H17	0.299289	1.032279	0.830770	0.025*
C18	0.22525 (12)	0.86117 (12)	0.71238 (9)	0.0251 (2)
H18	0.125298	0.875244	0.689406	0.030*
C19	0.26769 (13)	0.74743 (12)	0.66210 (9)	0.0277 (2)
H19	0.197060	0.684161	0.604343	0.033*
C20	0.41328 (14)	0.72607 (12)	0.69617 (9)	0.0285 (3)
H20	0.442188	0.648021	0.661755	0.034*
C21	0.51726 (12)	0.81880 (11)	0.78076 (9)	0.0234 (2)
H21	0.616527	0.803107	0.804782	0.028*
O5	−0.16140 (8)	0.74669 (8)	0.22439 (6)	0.02307 (17)
O6	−0.03885 (9)	0.80244 (9)	0.12317 (6)	0.02892 (19)
H6O	−0.1140 (19)	0.747 (2)	0.0769 (14)	0.088 (8)*
C22	−0.05202 (11)	0.80401 (10)	0.21249 (8)	0.0187 (2)
C23	0.08033 (11)	0.88364 (10)	0.30063 (8)	0.0180 (2)
C24	0.20594 (11)	0.94266 (11)	0.28499 (8)	0.0192 (2)
H24	0.209182	0.931865	0.217699	0.023*
C25	0.32654 (12)	1.01739 (11)	0.36799 (8)	0.0220 (2)
H25	0.412647	1.056907	0.357507	0.026*
C26	0.32108 (12)	1.03425 (11)	0.46627 (8)	0.0238 (2)
H26	0.402958	1.086590	0.522807	0.029*
C27	0.19693 (13)	0.97515 (12)	0.48208 (8)	0.0263 (2)
H27	0.193811	0.986854	0.549439	0.032*
C28	0.07667 (12)	0.89864 (12)	0.39969 (8)	0.0234 (2)
H28	−0.007838	0.856648	0.410794	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0163 (3)	0.0268 (4)	0.0250 (4)	0.0018 (3)	0.0078 (3)	0.0085 (3)
O2	0.0161 (3)	0.0251 (4)	0.0224 (4)	0.0018 (3)	0.0071 (3)	0.0073 (3)
N1	0.0217 (4)	0.0236 (4)	0.0177 (4)	0.0029 (3)	0.0053 (3)	0.0035 (3)
N2	0.0144 (4)	0.0222 (4)	0.0158 (4)	0.0011 (3)	0.0041 (3)	0.0041 (3)
N3	0.0153 (4)	0.0199 (4)	0.0159 (4)	0.0001 (3)	0.0042 (3)	0.0037 (3)
N4	0.0231 (4)	0.0248 (5)	0.0158 (4)	−0.0006 (4)	0.0035 (3)	0.0036 (3)
C1	0.0189 (5)	0.0246 (5)	0.0190 (5)	0.0039 (4)	0.0040 (4)	0.0072 (4)
C2	0.0193 (5)	0.0200 (5)	0.0205 (5)	0.0045 (4)	0.0064 (4)	0.0055 (4)
C3	0.0171 (5)	0.0206 (5)	0.0168 (5)	0.0014 (4)	0.0068 (4)	0.0058 (4)
C4	0.0189 (5)	0.0245 (5)	0.0188 (5)	0.0056 (4)	0.0050 (4)	0.0058 (4)
C5	0.0241 (5)	0.0230 (5)	0.0207 (5)	0.0072 (4)	0.0072 (4)	0.0039 (4)
C6	0.0187 (5)	0.0203 (5)	0.0171 (5)	0.0039 (4)	0.0045 (4)	0.0046 (4)
C7	0.0166 (5)	0.0166 (4)	0.0151 (4)	0.0012 (4)	0.0048 (4)	0.0008 (4)
C8	0.0166 (4)	0.0147 (4)	0.0154 (4)	0.0005 (3)	0.0041 (4)	0.0005 (4)
C9	0.0199 (5)	0.0194 (5)	0.0178 (5)	0.0021 (4)	0.0033 (4)	0.0051 (4)
C10	0.0193 (5)	0.0200 (5)	0.0138 (4)	0.0020 (4)	0.0038 (4)	0.0061 (4)
C11	0.0174 (5)	0.0309 (6)	0.0248 (5)	0.0033 (4)	0.0044 (4)	−0.0005 (5)
C12	0.0249 (5)	0.0285 (6)	0.0241 (5)	0.0046 (4)	0.0065 (4)	−0.0020 (4)
C13	0.0171 (5)	0.0319 (6)	0.0211 (5)	0.0005 (4)	0.0041 (4)	0.0058 (4)
C14	0.0213 (5)	0.0258 (5)	0.0199 (5)	0.0044 (4)	0.0077 (4)	0.0035 (4)
O3	0.0264 (4)	0.0233 (4)	0.0216 (4)	0.0062 (3)	0.0047 (3)	−0.0006 (3)
O4	0.0220 (4)	0.0262 (4)	0.0213 (4)	0.0050 (3)	0.0038 (3)	−0.0017 (3)
C15	0.0226 (5)	0.0211 (5)	0.0139 (4)	0.0036 (4)	0.0071 (4)	0.0057 (4)
C16	0.0239 (5)	0.0191 (5)	0.0151 (5)	0.0011 (4)	0.0077 (4)	0.0062 (4)
C17	0.0250 (5)	0.0207 (5)	0.0196 (5)	0.0028 (4)	0.0091 (4)	0.0067 (4)
C18	0.0233 (5)	0.0277 (6)	0.0231 (5)	−0.0008 (4)	0.0054 (4)	0.0095 (4)
C19	0.0312 (6)	0.0246 (5)	0.0219 (5)	−0.0066 (4)	0.0061 (4)	0.0030 (4)
C20	0.0346 (6)	0.0211 (5)	0.0271 (6)	−0.0005 (5)	0.0121 (5)	−0.0009 (4)
C21	0.0249 (5)	0.0216 (5)	0.0238 (5)	0.0025 (4)	0.0096 (4)	0.0042 (4)
O5	0.0201 (4)	0.0254 (4)	0.0238 (4)	0.0009 (3)	0.0082 (3)	0.0061 (3)
O6	0.0266 (4)	0.0374 (5)	0.0158 (4)	−0.0093 (3)	0.0058 (3)	−0.0004 (3)
C22	0.0203 (5)	0.0175 (5)	0.0187 (5)	0.0035 (4)	0.0070 (4)	0.0045 (4)
C23	0.0203 (5)	0.0158 (4)	0.0174 (5)	0.0041 (4)	0.0055 (4)	0.0038 (4)
C24	0.0216 (5)	0.0196 (5)	0.0171 (5)	0.0048 (4)	0.0067 (4)	0.0049 (4)
C25	0.0192 (5)	0.0218 (5)	0.0233 (5)	0.0023 (4)	0.0053 (4)	0.0050 (4)
C26	0.0234 (5)	0.0226 (5)	0.0194 (5)	0.0054 (4)	0.0010 (4)	0.0011 (4)
C27	0.0315 (6)	0.0310 (6)	0.0156 (5)	0.0068 (5)	0.0072 (4)	0.0042 (4)
C28	0.0251 (5)	0.0267 (5)	0.0205 (5)	0.0034 (4)	0.0102 (4)	0.0066 (4)

Geometric parameters (Å, º) top

O1—C7	1.2270 (12)	C13—H13	0.9500
O2—C8	1.2312 (12)	C14—H14	0.9500
N1—C5	1.3395 (14)	O3—C15	1.2162 (13)
N1—C1	1.3421 (14)	O4—C15	1.3197 (13)
N2—C7	1.3336 (13)	O4—H4O	0.860 (10)
N2—C6	1.4538 (13)	C15—C16	1.4980 (14)
N2—H2N	0.881 (9)	C16—C21	1.3902 (15)
N3—C8	1.3298 (13)	C16—C17	1.3929 (15)
N3—C9	1.4570 (13)	C17—C18	1.3895 (15)
N3—H3N	0.883 (9)	C17—H17	0.9500
N4—C12	1.3346 (15)	C18—C19	1.3867 (17)
N4—C13	1.3338 (15)	C18—H18	0.9500
C1—C2	1.3845 (15)	C19—C20	1.3869 (18)
C1—H1	0.9500	C19—H19	0.9500
C2—C3	1.3968 (14)	C20—C21	1.3935 (16)
C2—H2	0.9500	C20—H20	0.9500
C3—C4	1.3869 (15)	C21—H21	0.9500
C3—C6	1.5157 (14)	O5—C22	1.2237 (13)
C4—C5	1.3906 (15)	O6—C22	1.3084 (13)
C4—H4	0.9500	O6—H6O	0.865 (10)
C5—H5	0.9500	C22—C23	1.4991 (14)
C6—H6A	0.9900	C23—C24	1.3932 (15)
C6—H6B	0.9900	C23—C28	1.3955 (15)
C7—C8	1.5402 (14)	C24—C25	1.3904 (15)
C9—C10	1.5139 (14)	C24—H24	0.9500
C9—H9A	0.9900	C25—C26	1.3893 (16)
C9—H9B	0.9900	C25—H25	0.9500
C10—C11	1.3861 (15)	C26—C27	1.3824 (17)
C10—C14	1.3857 (15)	C26—H26	0.9500
C11—C12	1.3894 (16)	C27—C28	1.3899 (16)
C11—H11	0.9500	C27—H27	0.9500
C12—H12	0.9500	C28—H28	0.9500
C13—C14	1.3857 (15)

C5—N1—C1	117.75 (9)	N4—C13—C14	123.03 (10)
C7—N2—C6	121.82 (9)	N4—C13—H13	118.5
C7—N2—H2N	119.7 (9)	C14—C13—H13	118.5
C6—N2—H2N	118.1 (9)	C13—C14—C10	118.93 (10)
C8—N3—C9	120.98 (9)	C13—C14—H14	120.5
C8—N3—H3N	120.2 (9)	C10—C14—H14	120.5
C9—N3—H3N	118.8 (9)	C15—O4—H4O	108.5 (15)
C12—N4—C13	118.30 (9)	O3—C15—O4	123.81 (9)
N1—C1—C2	122.96 (10)	O3—C15—C16	122.06 (10)
N1—C1—H1	118.5	O4—C15—C16	114.08 (9)
C2—C1—H1	118.5	C21—C16—C17	119.87 (10)
C1—C2—C3	119.25 (10)	C21—C16—C15	121.37 (10)
C1—C2—H2	120.4	C17—C16—C15	118.72 (9)
C3—C2—H2	120.4	C16—C17—C18	120.01 (10)
C4—C3—C2	117.79 (9)	C16—C17—H17	120.0
C4—C3—C6	123.35 (9)	C18—C17—H17	120.0
C2—C3—C6	118.85 (9)	C19—C18—C17	120.12 (11)
C3—C4—C5	119.32 (10)	C19—C18—H18	119.9
C3—C4—H4	120.3	C17—C18—H18	119.9
C5—C4—H4	120.3	C18—C19—C20	119.98 (10)
N1—C5—C4	122.91 (10)	C18—C19—H19	120.0
N1—C5—H5	118.5	C20—C19—H19	120.0
C4—C5—H5	118.5	C19—C20—C21	120.18 (11)
N2—C6—C3	114.41 (8)	C19—C20—H20	119.9
N2—C6—H6A	108.7	C21—C20—H20	119.9
C3—C6—H6A	108.7	C16—C21—C20	119.82 (11)
N2—C6—H6B	108.7	C16—C21—H21	120.1
C3—C6—H6B	108.7	C20—C21—H21	120.1
H6A—C6—H6B	107.6	C22—O6—H6O	108.4 (17)
O1—C7—N2	125.93 (9)	O5—C22—O6	123.94 (9)
O1—C7—C8	121.14 (9)	O5—C22—C23	122.33 (9)
N2—C7—C8	112.92 (8)	O6—C22—C23	113.73 (9)
O2—C8—N3	124.54 (9)	C24—C23—C28	119.83 (9)
O2—C8—C7	121.86 (9)	C24—C23—C22	121.07 (9)
N3—C8—C7	113.60 (9)	C28—C23—C22	119.10 (9)
N3—C9—C10	113.22 (8)	C25—C24—C23	119.91 (10)
N3—C9—H9A	108.9	C25—C24—H24	120.0
C10—C9—H9A	108.9	C23—C24—H24	120.0
N3—C9—H9B	108.9	C26—C25—C24	119.98 (10)
C10—C9—H9B	108.9	C26—C25—H25	120.0
H9A—C9—H9B	107.7	C24—C25—H25	120.0
C11—C10—C14	117.99 (9)	C27—C26—C25	120.23 (10)
C11—C10—C9	121.18 (9)	C27—C26—H26	119.9
C14—C10—C9	120.79 (9)	C25—C26—H26	119.9
C10—C11—C12	119.57 (10)	C26—C27—C28	120.18 (10)
C10—C11—H11	120.2	C26—C27—H27	119.9
C12—C11—H11	120.2	C28—C27—H27	119.9
N4—C12—C11	122.16 (11)	C27—C28—C23	119.85 (10)
N4—C12—H12	118.9	C27—C28—H28	120.1
C11—C12—H12	118.9	C23—C28—H28	120.1

C5—N1—C1—C2	−0.12 (16)	N4—C13—C14—C10	1.01 (17)
N1—C1—C2—C3	−0.91 (16)	C11—C10—C14—C13	0.07 (16)
C1—C2—C3—C4	1.13 (15)	C9—C10—C14—C13	−177.84 (10)
C1—C2—C3—C6	−178.91 (9)	O3—C15—C16—C21	174.45 (10)
C2—C3—C4—C5	−0.39 (15)	O4—C15—C16—C21	−3.20 (14)
C6—C3—C4—C5	179.65 (10)	O3—C15—C16—C17	−3.13 (15)
C1—N1—C5—C4	0.91 (16)	O4—C15—C16—C17	179.22 (9)
C3—C4—C5—N1	−0.66 (17)	C21—C16—C17—C18	−1.48 (15)
C7—N2—C6—C3	−87.36 (12)	C15—C16—C17—C18	176.13 (9)
C4—C3—C6—N2	−12.00 (14)	C16—C17—C18—C19	0.20 (16)
C2—C3—C6—N2	168.05 (9)	C17—C18—C19—C20	0.61 (17)
C6—N2—C7—O1	3.86 (16)	C18—C19—C20—C21	−0.12 (18)
C6—N2—C7—C8	−175.03 (8)	C17—C16—C21—C20	1.96 (16)
C9—N3—C8—O2	−1.50 (15)	C15—C16—C21—C20	−175.59 (10)
C9—N3—C8—C7	178.88 (8)	C19—C20—C21—C16	−1.17 (17)
O1—C7—C8—O2	173.94 (9)	O5—C22—C23—C24	177.14 (10)
N2—C7—C8—O2	−7.10 (13)	O6—C22—C23—C24	−3.01 (14)
O1—C7—C8—N3	−6.43 (13)	O5—C22—C23—C28	−2.98 (16)
N2—C7—C8—N3	172.52 (8)	O6—C22—C23—C28	176.87 (10)
C8—N3—C9—C10	75.45 (12)	C28—C23—C24—C25	−0.63 (15)
N3—C9—C10—C11	50.59 (14)	C22—C23—C24—C25	179.25 (9)
N3—C9—C10—C14	−131.57 (10)	C23—C24—C25—C26	−0.63 (16)
C14—C10—C11—C12	−0.84 (17)	C24—C25—C26—C27	1.00 (16)
C9—C10—C11—C12	177.05 (10)	C25—C26—C27—C28	−0.10 (17)
C13—N4—C12—C11	0.40 (18)	C26—C27—C28—C23	−1.16 (17)
C10—C11—C12—N4	0.64 (19)	C24—C23—C28—C27	1.52 (16)
C12—N4—C13—C14	−1.24 (17)	C22—C23—C28—C27	−178.36 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O2	0.88 (1)	2.36 (1)	2.7192 (12)	105 (1)
N3—H3N···O1	0.88 (1)	2.36 (1)	2.7154 (12)	104 (1)
O4—H4O···N1ⁱ	0.86 (2)	1.78 (2)	2.6366 (12)	177 (2)
O6—H6O···N4ⁱⁱ	0.86 (2)	1.72 (2)	2.5731 (13)	169 (2)
N2—H2N···O2ⁱⁱⁱ	0.88 (1)	2.05 (1)	2.8618 (12)	152 (1)
N3—H3N···O5^iv	0.88 (1)	2.12 (1)	2.8516 (12)	140 (1)
C1—H1···O3^v	0.95	2.58	3.2009 (14)	124
C2—H2···O5	0.95	2.47	3.3602 (14)	155
C6—H6B···O1^iv	0.99	2.41	3.3826 (14)	166
C12—H12···O3^vi	0.95	2.36	3.3025 (15)	171

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

A summary of short interatomic contacts (Å) in (I)^a top

Contact	Distance	Symmetry operation
O2···H2N^b	1.94	1 - x, 1 - y, 1 - z
C1···H13	2.79	-1 + x, y, -1 + z
N1···H4O^b	1.65	-1 + x, -1 + y, -1 + z
O3···H1	2.50	1 + x, 1 + y, 1 + z
N4···H6O^b	1.60	1 + x, y, 1 + z
O5···H3N^b	2.02	-x, 1 - y, 1 - z
O1···H28	2.57	-x, 1 - y, 1 - z
O1···H6B	2.32	-x, 1 - y, 1 - z
C8···H20	2.61	x, y, z
C12···C21	3.39	x, y, z
C8···C26	3.35	x, -1 + y, z
O5···H2	2.35	x, y, z
O3···H9B	2.56	x, 1 + y, z
C17···H9B	2.69	x, 1 + y, z
O3···H12	2.23	1 - x, 2 - y, 2 - z
C21···H25	2.62	1 - x, 2 - y, 1 - z
C18···H27	2.67	x, y, z
O4···H24	2.58	1 - x, 2 - y, 1 - z

Notes: (a) The interatomic distances are calculated in Crystal Explorer 17 (Turner et al., 2017) whereby the X—H bond lengths are adjusted to their neutron values; (b) these interactions correspond to conventional hydrogen bonds.

A summary of interaction energies (kJ mol^-1) calculated for (I) top

Contact	E_ele	E_pol	E_dis	E_rep	E_tot	Symmetry operation
N2—H2N···O2/
C13—H13···C1	-60.9	-14.6	-58.5	82.5	-75.2	1 - x, 1 - y, 1 - z
O4—H4O···N1/
C1—H1···O3	-90.7	-21.3	-13.0	118.0	-50.1	-1 + x, -1 + y, -1 + z
O6—H6O···N4	-95.2	-22.2	-11.3	134.4	-43.9	1 + x, y, 1 + z
N3—H3N···O5/
C28—H28···O1	-32.8	-8.6	-16.1	30.3	-36.3	- x, 1 - y, 1 - z
C6—H6B···O1	-11.4	-5.1	-29.5	26.4	-25.1	- x, 1 - y, 1 - z
C20—H20···C8/
C12···C21	-5.8	-1.5	-32.7	23.8	-21.0	x, y, z
C8···C26	-3.7	-1.0	-31.9	21.1	-19.4	x, -1 + y, z
C2—H2···O5	-9.4	-1.9	-14.0	12.9	-15.6	x, y, z
C9—H9B···O3/
C9—H9B···C17	-6.0	-2.2	-17.3	13.5	-14.7	x, 1 + y, z
C12—H12···O3	-9.5	-2.4	-4.9	12.6	-8.3	1 - x, 2 - y, 2 - z

Selected geometric data, i.e. central C—C bond length, O—H···N and NC—H···O(carbonyl) separations (Å) for ⁴LH₂ in its co-crystals with carboxylic acids and salt with a carboxylate anion top

Carboxylic acid (CA)	Symmetry of ⁴LH₂	C—C	O—H···N(pyridyl)	NC—H···O(carbonyl)	REFCODE	Reference
1:1 co-crystal
bis(carboxymethyl)urea	–	1.53 (2)	1.73	2.54	CAJRAH	Nguyen et al. (2001)
			1.75	4.21
diglycineoxamide	1	1.514 (5)	1.74	3.11	SEPSIP01	Nguyen et al. (2001)
poly(1,2-bis(2-carboxyethyl)tetra-1-en-3-yn-1,4-diyl	1	1.537 (13)	1.80	2.98	DOVSIR	Curtis et al. (2005)

2:1 co-crystal
(4-nitrophenyl)acetic acid	1	1.543 (2)	1.57	2.72	NAXMEG	Arman, Kaulgud et al. (2012)
benzoic acid	–	1.5401 (14)	1.67	2.59	–	This work
			1.72	3.46
2-methylbenzoic acid	1	1.5356 (19)	1.79	2.60	WADXUX	Syed et al. (2016)
acetic acid^a	1	1.5397 (17)	1.75	2.81	GOQQIP	Tan & Tiekink (2019b)
2-[(4-hydroxyphenyl)diazenyl]benzoic acid^b	1	1.542 (2)	1.89	–	AJEZEV	Arman et al. (2009)
2,6-dinitrobenzoate^c	1	1.543 (3)	1.96^c	2.51	TIPGUW	Arman, Miller et al. (2012)

Notes: (a) Characterized as a di-hydrate; (b) hydroxy-O—N(pyridyl) hydrogen bond; (c) salt with a pyridinium-N—H···O(carboxylate) hydrogen bond.

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The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmeth­yl)ethanedi­amide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study

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The 1:2 co-crystal formed between N,N′-bis(pyridin-4-ylmethyl)ethanediamide and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study