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

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

doi:10.1107/S2056989020000572

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

In the title 1:2 co-crystal, ⁴LH₂:2CBA, two independent three-molecule aggregates, i.e. ⁴LH₂(CBA)₂, are formed, each located about a centre of inversion and sustained by carboxylic acid-O—H

N(pyridyl) hydrogen bonding. The three-molecule aggregates are connected into a supramolecular tape by amide-N—H

O(amide) hydrogen bonding.

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/S2056989020000572/hb7889sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020000572/hb7889Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020000572/hb7889Isup3.cml Supplementary material

CCDC reference: 1978104

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.032
wR factor = 0.090
Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C7       - C7_a     .       1.54 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C14      - C14_b    .       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
PLAT432_ALERT_2_G Short Inter X...Y Contact  Cl2      ..C14              3.21 Ang.
                                              -1+x,-1+y,1+z  =      1_446 Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          3 Note
              C7 H5 Cl O2
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.         20 Info

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   3 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 (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–4-chlorobenzoic acid (1/2) top

Crystal data top

C₁₄H₁₄N₄O₂·2C₇H₅ClO₂	Z = 2
M_r = 583.41	F(000) = 604
Triclinic, P1	D_x = 1.475 Mg m⁻³
a = 9.9401 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.2002 (2) Å	Cell parameters from 14644 reflections
c = 12.3308 (3) Å	θ = 3.7–76.1°
α = 78.871 (2)°	µ = 2.67 mm⁻¹
β = 78.816 (2)°	T = 100 K
γ = 81.992 (2)°	Plate, colourless
V = 1313.98 (5) Å³	0.13 × 0.04 × 0.03 mm

Data collection top

XtaLAB Synergy, Dualflex, AtlasS2 diffractometer	5486 independent reflections
Radiation source: micro-focus sealed X-ray tube	4814 reflections with I > 2σ(I)
Detector resolution: 5.2558 pixels mm^-1	R_int = 0.034
ω scans	θ_max = 76.5°, θ_min = 3.7°
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018)	h = −9→12
T_min = 0.847, T_max = 1.000	k = −14→14
33133 measured reflections	l = −15→15

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)] = 0.032	Hydrogen site location: mixed
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0502P)² + 0.3813P] where P = (F_o² + 2F_c²)/3
5486 reflections	(Δ/σ)_max = 0.002
373 parameters	Δρ_max = 0.29 e Å⁻³
4 restraints	Δρ_min = −0.33 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	0.60739 (8)	0.97776 (8)	0.10123 (7)	0.01871 (18)
N1	0.18629 (11)	0.75161 (10)	0.46595 (9)	0.0226 (2)
N2	0.37710 (10)	1.03739 (10)	0.11754 (9)	0.0171 (2)
H2N	0.3042 (12)	1.0441 (15)	0.0858 (13)	0.021*
C1	0.10938 (13)	0.85755 (12)	0.43978 (11)	0.0219 (3)
H1	0.014870	0.864969	0.473525	0.026*
C2	0.16098 (12)	0.95678 (12)	0.36591 (11)	0.0200 (2)
H2	0.102752	1.030329	0.349550	0.024*
C3	0.29944 (12)	0.94745 (11)	0.31582 (10)	0.0179 (2)
C4	0.38016 (13)	0.83804 (12)	0.34405 (11)	0.0213 (3)
H4	0.475365	0.828721	0.312628	0.026*
C5	0.32023 (13)	0.74264 (12)	0.41854 (11)	0.0235 (3)
H5	0.376045	0.668080	0.436755	0.028*
C6	0.35802 (12)	1.05429 (12)	0.23434 (11)	0.0197 (2)
H6A	0.295105	1.129610	0.244075	0.024*
H6B	0.447977	1.065548	0.251964	0.024*
C7	0.50027 (11)	1.00274 (10)	0.06174 (10)	0.0146 (2)
O2	1.10206 (8)	0.99617 (8)	0.10296 (7)	0.02007 (19)
N3	0.69677 (11)	0.75172 (10)	0.47531 (9)	0.0211 (2)
N4	0.86920 (10)	1.03345 (10)	0.11304 (9)	0.0173 (2)
H4N	0.8027 (13)	1.0328 (15)	0.0771 (12)	0.021*
C8	0.65934 (13)	0.86787 (12)	0.49045 (11)	0.0216 (3)
H8	0.599965	0.882524	0.557915	0.026*
C9	0.70303 (12)	0.96737 (12)	0.41257 (11)	0.0202 (2)
H9	0.674340	1.048201	0.426901	0.024*
C10	0.78943 (11)	0.94780 (11)	0.31302 (10)	0.0174 (2)
C11	0.82958 (12)	0.82740 (12)	0.29757 (11)	0.0210 (3)
H11	0.889290	0.810106	0.231079	0.025*
C12	0.78155 (13)	0.73269 (12)	0.38030 (11)	0.0221 (3)
H12	0.810108	0.650822	0.368968	0.027*
C13	0.83531 (12)	1.05668 (11)	0.22714 (10)	0.0186 (2)
H13A	0.760868	1.125137	0.231071	0.022*
H13B	0.917196	1.082945	0.246930	0.022*
C14	0.99697 (11)	1.00732 (11)	0.06123 (10)	0.0154 (2)
Cl1	−0.37720 (3)	0.26656 (3)	1.00591 (3)	0.02890 (10)
O3	−0.07627 (10)	0.73883 (9)	0.67521 (9)	0.0304 (2)
O4	0.03544 (10)	0.58218 (9)	0.59372 (8)	0.0268 (2)
H4O	0.0841 (18)	0.6388 (14)	0.5594 (16)	0.040*
C15	−0.06010 (13)	0.63083 (12)	0.66763 (11)	0.0222 (3)
C16	−0.14493 (12)	0.53923 (12)	0.74585 (11)	0.0205 (3)
C17	−0.23844 (13)	0.57765 (12)	0.83541 (11)	0.0216 (3)
H17	−0.252419	0.661813	0.841895	0.026*
C18	−0.31121 (13)	0.49417 (12)	0.91512 (11)	0.0220 (3)
H18	−0.374727	0.520178	0.976363	0.026*
C19	−0.28935 (13)	0.37174 (12)	0.90357 (12)	0.0217 (3)
C20	−0.19944 (13)	0.33124 (12)	0.81370 (12)	0.0240 (3)
H20	−0.187517	0.247331	0.806467	0.029*
C21	−0.12741 (13)	0.41610 (12)	0.73471 (12)	0.0230 (3)
H21	−0.065666	0.390163	0.672537	0.028*
Cl2	0.09083 (4)	0.27800 (3)	0.98266 (3)	0.03057 (10)
O5	0.42589 (10)	0.74219 (9)	0.67193 (9)	0.0298 (2)
O6	0.56489 (9)	0.58098 (9)	0.61812 (8)	0.0242 (2)
H6O	0.6094 (17)	0.6374 (14)	0.5776 (14)	0.036*
C22	0.45469 (13)	0.63220 (12)	0.67727 (11)	0.0205 (3)
C23	0.36560 (12)	0.54182 (12)	0.75218 (11)	0.0194 (2)
C24	0.22992 (13)	0.58221 (12)	0.79557 (11)	0.0221 (3)
H24	0.196233	0.665934	0.777238	0.026*
C25	0.14420 (13)	0.50108 (12)	0.86510 (11)	0.0227 (3)
H25	0.051448	0.527996	0.893646	0.027*
C26	0.19648 (14)	0.37974 (12)	0.89221 (11)	0.0223 (3)
C27	0.33072 (14)	0.33723 (12)	0.85065 (12)	0.0237 (3)
H27	0.364433	0.253713	0.870218	0.028*
C28	0.41476 (13)	0.41920 (12)	0.77991 (11)	0.0212 (3)
H28	0.506744	0.391414	0.750081	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0124 (4)	0.0244 (4)	0.0184 (4)	−0.0031 (3)	−0.0020 (3)	−0.0012 (3)
N1	0.0252 (5)	0.0229 (6)	0.0182 (5)	−0.0028 (4)	0.0006 (4)	−0.0039 (4)
N2	0.0126 (4)	0.0213 (5)	0.0165 (5)	−0.0018 (4)	−0.0001 (4)	−0.0036 (4)
C1	0.0181 (5)	0.0265 (7)	0.0199 (6)	−0.0024 (5)	0.0006 (5)	−0.0049 (5)
C2	0.0179 (6)	0.0229 (6)	0.0181 (6)	0.0003 (5)	−0.0019 (5)	−0.0041 (5)
C3	0.0184 (5)	0.0217 (6)	0.0145 (5)	−0.0025 (4)	−0.0016 (4)	−0.0063 (5)
C4	0.0189 (6)	0.0246 (6)	0.0192 (6)	0.0007 (5)	−0.0001 (5)	−0.0062 (5)
C5	0.0256 (6)	0.0223 (6)	0.0202 (6)	0.0029 (5)	−0.0018 (5)	−0.0041 (5)
C6	0.0198 (6)	0.0208 (6)	0.0179 (6)	−0.0033 (5)	0.0015 (5)	−0.0061 (5)
C7	0.0134 (5)	0.0125 (5)	0.0166 (6)	−0.0038 (4)	−0.0002 (4)	0.0002 (4)
O2	0.0128 (4)	0.0279 (5)	0.0189 (4)	−0.0032 (3)	−0.0018 (3)	−0.0028 (4)
N3	0.0195 (5)	0.0227 (5)	0.0200 (5)	−0.0023 (4)	−0.0010 (4)	−0.0031 (4)
N4	0.0118 (4)	0.0227 (5)	0.0168 (5)	−0.0019 (4)	−0.0011 (4)	−0.0036 (4)
C8	0.0219 (6)	0.0249 (6)	0.0179 (6)	−0.0028 (5)	0.0006 (5)	−0.0069 (5)
C9	0.0196 (6)	0.0207 (6)	0.0202 (6)	−0.0014 (5)	−0.0001 (5)	−0.0070 (5)
C10	0.0124 (5)	0.0220 (6)	0.0185 (6)	−0.0020 (4)	−0.0026 (4)	−0.0047 (5)
C11	0.0179 (5)	0.0227 (6)	0.0205 (6)	−0.0003 (5)	0.0024 (5)	−0.0062 (5)
C12	0.0202 (6)	0.0199 (6)	0.0247 (7)	−0.0001 (5)	0.0004 (5)	−0.0057 (5)
C13	0.0161 (5)	0.0202 (6)	0.0184 (6)	−0.0020 (4)	0.0015 (4)	−0.0053 (5)
C14	0.0134 (5)	0.0142 (5)	0.0171 (6)	−0.0036 (4)	−0.0005 (4)	0.0003 (4)
Cl1	0.02788 (17)	0.02064 (16)	0.03483 (19)	−0.00701 (12)	−0.00165 (13)	0.00283 (13)
O3	0.0325 (5)	0.0191 (5)	0.0334 (6)	−0.0029 (4)	0.0071 (4)	−0.0023 (4)
O4	0.0290 (5)	0.0232 (5)	0.0250 (5)	−0.0049 (4)	0.0060 (4)	−0.0053 (4)
C15	0.0219 (6)	0.0215 (6)	0.0221 (6)	−0.0008 (5)	−0.0026 (5)	−0.0030 (5)
C16	0.0186 (5)	0.0205 (6)	0.0224 (6)	−0.0020 (5)	−0.0038 (5)	−0.0037 (5)
C17	0.0223 (6)	0.0171 (6)	0.0252 (7)	−0.0015 (5)	−0.0034 (5)	−0.0043 (5)
C18	0.0204 (6)	0.0213 (6)	0.0237 (6)	−0.0029 (5)	−0.0012 (5)	−0.0045 (5)
C19	0.0186 (5)	0.0195 (6)	0.0268 (7)	−0.0047 (5)	−0.0052 (5)	−0.0005 (5)
C20	0.0220 (6)	0.0174 (6)	0.0337 (7)	−0.0016 (5)	−0.0057 (5)	−0.0065 (5)
C21	0.0202 (6)	0.0228 (6)	0.0265 (7)	−0.0012 (5)	−0.0026 (5)	−0.0078 (5)
Cl2	0.03914 (19)	0.02243 (17)	0.02819 (18)	−0.01267 (13)	0.00685 (14)	−0.00548 (13)
O5	0.0297 (5)	0.0185 (5)	0.0339 (6)	−0.0007 (4)	0.0079 (4)	−0.0010 (4)
O6	0.0214 (4)	0.0210 (5)	0.0258 (5)	−0.0010 (4)	0.0039 (4)	−0.0023 (4)
C22	0.0199 (6)	0.0198 (6)	0.0206 (6)	−0.0004 (5)	−0.0027 (5)	−0.0027 (5)
C23	0.0199 (6)	0.0196 (6)	0.0184 (6)	−0.0018 (5)	−0.0025 (5)	−0.0037 (5)
C24	0.0218 (6)	0.0180 (6)	0.0247 (6)	0.0009 (5)	−0.0026 (5)	−0.0030 (5)
C25	0.0205 (6)	0.0233 (6)	0.0237 (6)	−0.0019 (5)	−0.0009 (5)	−0.0053 (5)
C26	0.0272 (6)	0.0207 (6)	0.0196 (6)	−0.0073 (5)	−0.0007 (5)	−0.0046 (5)
C27	0.0298 (7)	0.0167 (6)	0.0238 (6)	−0.0007 (5)	−0.0029 (5)	−0.0039 (5)
C28	0.0214 (6)	0.0200 (6)	0.0216 (6)	0.0010 (5)	−0.0022 (5)	−0.0059 (5)

Geometric parameters (Å, º) top

O1—C7	1.2307 (14)	C13—H13A	0.9900
N1—C1	1.3386 (17)	C13—H13B	0.9900
N1—C5	1.3445 (17)	C14—C14ⁱⁱ	1.539 (2)
N2—C7	1.3292 (15)	Cl1—C19	1.7402 (13)
N2—C6	1.4612 (16)	O3—C15	1.2172 (17)
N2—H2N	0.876 (9)	O4—C15	1.3196 (16)
C1—C2	1.3838 (19)	O4—H4O	0.847 (9)
C1—H1	0.9500	C15—C16	1.4958 (18)
C2—C3	1.3935 (17)	C16—C17	1.3938 (19)
C2—H2	0.9500	C16—C21	1.3957 (18)
C3—C4	1.3915 (18)	C17—C18	1.3861 (19)
C3—C6	1.5111 (17)	C17—H17	0.9500
C4—C5	1.3879 (19)	C18—C19	1.3886 (19)
C4—H4	0.9500	C18—H18	0.9500
C5—H5	0.9500	C19—C20	1.389 (2)
C6—H6A	0.9900	C20—C21	1.388 (2)
C6—H6B	0.9900	C20—H20	0.9500
C7—C7ⁱ	1.537 (2)	C21—H21	0.9500
O2—C14	1.2325 (14)	Cl2—C26	1.7418 (13)
N3—C12	1.3385 (17)	O5—C22	1.2173 (17)
N3—C8	1.3408 (17)	O6—C22	1.3181 (16)
N4—C14	1.3269 (15)	O6—H6O	0.846 (9)
N4—C13	1.4471 (16)	C22—C23	1.4945 (18)
N4—H4N	0.865 (9)	C23—C28	1.3923 (18)
C8—C9	1.3830 (19)	C23—C24	1.3977 (17)
C8—H8	0.9500	C24—C25	1.3850 (19)
C9—C10	1.3911 (17)	C24—H24	0.9500
C9—H9	0.9500	C25—C26	1.3871 (19)
C10—C11	1.3906 (18)	C25—H25	0.9500
C10—C13	1.5118 (17)	C26—C27	1.3862 (19)
C11—C12	1.3886 (19)	C27—C28	1.3869 (19)
C11—H11	0.9500	C27—H27	0.9500
C12—H12	0.9500	C28—H28	0.9500

C1—N1—C5	117.89 (11)	N4—C13—H13B	108.7
C7—N2—C6	121.67 (10)	C10—C13—H13B	108.7
C7—N2—H2N	119.5 (11)	H13A—C13—H13B	107.6
C6—N2—H2N	118.6 (11)	O2—C14—N4	125.67 (11)
N1—C1—C2	123.12 (12)	O2—C14—C14ⁱⁱ	121.76 (13)
N1—C1—H1	118.4	N4—C14—C14ⁱⁱ	112.57 (12)
C2—C1—H1	118.4	C15—O4—H4O	106.4 (14)
C1—C2—C3	119.15 (12)	O3—C15—O4	124.16 (12)
C1—C2—H2	120.4	O3—C15—C16	122.31 (12)
C3—C2—H2	120.4	O4—C15—C16	113.49 (11)
C4—C3—C2	117.87 (12)	C17—C16—C21	119.62 (12)
C4—C3—C6	121.98 (11)	C17—C16—C15	118.56 (12)
C2—C3—C6	120.14 (11)	C21—C16—C15	121.73 (12)
C5—C4—C3	119.37 (11)	C18—C17—C16	120.60 (12)
C5—C4—H4	120.3	C18—C17—H17	119.7
C3—C4—H4	120.3	C16—C17—H17	119.7
N1—C5—C4	122.59 (12)	C17—C18—C19	118.62 (12)
N1—C5—H5	118.7	C17—C18—H18	120.7
C4—C5—H5	118.7	C19—C18—H18	120.7
N2—C6—C3	112.69 (10)	C18—C19—C20	122.06 (12)
N2—C6—H6A	109.1	C18—C19—Cl1	118.50 (10)
C3—C6—H6A	109.1	C20—C19—Cl1	119.44 (10)
N2—C6—H6B	109.1	C21—C20—C19	118.52 (12)
C3—C6—H6B	109.1	C21—C20—H20	120.7
H6A—C6—H6B	107.8	C19—C20—H20	120.7
O1—C7—N2	125.33 (11)	C20—C21—C16	120.55 (12)
O1—C7—C7ⁱ	121.12 (13)	C20—C21—H21	119.7
N2—C7—C7ⁱ	113.55 (12)	C16—C21—H21	119.7
C12—N3—C8	117.64 (11)	C22—O6—H6O	108.1 (13)
C14—N4—C13	123.73 (10)	O5—C22—O6	124.16 (12)
C14—N4—H4N	117.5 (11)	O5—C22—C23	122.35 (12)
C13—N4—H4N	118.7 (11)	O6—C22—C23	113.49 (11)
N3—C8—C9	123.14 (12)	C28—C23—C24	119.54 (12)
N3—C8—H8	118.4	C28—C23—C22	121.62 (11)
C9—C8—H8	118.4	C24—C23—C22	118.84 (11)
C8—C9—C10	119.28 (12)	C25—C24—C23	120.48 (12)
C8—C9—H9	120.4	C25—C24—H24	119.8
C10—C9—H9	120.4	C23—C24—H24	119.8
C11—C10—C9	117.71 (12)	C24—C25—C26	118.68 (12)
C11—C10—C13	123.06 (11)	C24—C25—H25	120.7
C9—C10—C13	119.23 (11)	C26—C25—H25	120.7
C12—C11—C10	119.35 (12)	C27—C26—C25	122.06 (12)
C12—C11—H11	120.3	C27—C26—Cl2	118.96 (10)
C10—C11—H11	120.3	C25—C26—Cl2	118.97 (10)
N3—C12—C11	122.87 (12)	C26—C27—C28	118.61 (12)
N3—C12—H12	118.6	C26—C27—H27	120.7
C11—C12—H12	118.6	C28—C27—H27	120.7
N4—C13—C10	114.16 (10)	C27—C28—C23	120.62 (12)
N4—C13—H13A	108.7	C27—C28—H28	119.7
C10—C13—H13A	108.7	C23—C28—H28	119.7

C5—N1—C1—C2	0.7 (2)	O4—C15—C16—C17	172.82 (12)
N1—C1—C2—C3	−0.1 (2)	O3—C15—C16—C21	178.55 (13)
C1—C2—C3—C4	−0.79 (18)	O4—C15—C16—C21	−3.73 (18)
C1—C2—C3—C6	179.63 (11)	C21—C16—C17—C18	1.81 (19)
C2—C3—C4—C5	1.09 (18)	C15—C16—C17—C18	−174.81 (12)
C6—C3—C4—C5	−179.34 (12)	C16—C17—C18—C19	−0.24 (19)
C1—N1—C5—C4	−0.3 (2)	C17—C18—C19—C20	−1.41 (19)
C3—C4—C5—N1	−0.5 (2)	C17—C18—C19—Cl1	178.20 (10)
C7—N2—C6—C3	−101.17 (13)	C18—C19—C20—C21	1.4 (2)
C4—C3—C6—N2	76.87 (14)	Cl1—C19—C20—C21	−178.18 (10)
C2—C3—C6—N2	−103.57 (13)	C19—C20—C21—C16	0.20 (19)
C6—N2—C7—O1	2.55 (18)	C17—C16—C21—C20	−1.79 (19)
C6—N2—C7—C7ⁱ	−176.74 (11)	C15—C16—C21—C20	174.72 (12)
C12—N3—C8—C9	0.65 (19)	O5—C22—C23—C28	−163.13 (13)
N3—C8—C9—C10	0.33 (19)	O6—C22—C23—C28	17.41 (17)
C8—C9—C10—C11	−0.96 (18)	O5—C22—C23—C24	16.56 (19)
C8—C9—C10—C13	179.04 (11)	O6—C22—C23—C24	−162.89 (12)
C9—C10—C11—C12	0.65 (18)	C28—C23—C24—C25	−0.43 (19)
C13—C10—C11—C12	−179.36 (11)	C22—C23—C24—C25	179.87 (12)
C8—N3—C12—C11	−0.99 (19)	C23—C24—C25—C26	1.1 (2)
C10—C11—C12—N3	0.3 (2)	C24—C25—C26—C27	−0.9 (2)
C14—N4—C13—C10	−98.77 (13)	C24—C25—C26—Cl2	178.27 (10)
C11—C10—C13—N4	26.33 (16)	C25—C26—C27—C28	0.1 (2)
C9—C10—C13—N4	−153.67 (11)	Cl2—C26—C27—C28	−179.13 (10)
C13—N4—C14—O2	2.03 (19)	C26—C27—C28—C23	0.6 (2)
C13—N4—C14—C14ⁱⁱ	−177.41 (12)	C24—C23—C28—C27	−0.46 (19)
O3—C15—C16—C17	−4.90 (19)	C22—C23—C28—C27	179.24 (12)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.88 (1)	2.35 (2)	2.7088 (14)	105 (1)
N4—H4N···O2ⁱⁱ	0.87 (1)	2.30 (2)	2.7028 (14)	108 (1)
O4—H4O···N1	0.85 (2)	1.82 (2)	2.6559 (15)	171 (2)
O6—H6O···N3	0.85 (2)	1.80 (2)	2.6419 (15)	172 (2)
C8—H8···O5	0.95	2.53	3.1708 (17)	125
N2—H2N···O2ⁱⁱⁱ	0.88 (1)	2.11 (1)	2.8800 (13)	146 (1)
N4—H4N···O1	0.87 (1)	2.07 (1)	2.7959 (13)	141 (1)
C2—H2···O3^iv	0.95	2.53	3.3597 (17)	146
C6—H6A···O3^iv	0.99	2.59	3.5262 (17)	157
C9—H9···O5^v	0.95	2.59	3.3701 (17)	140
C13—H13A···O5^v	0.99	2.48	3.4006 (16)	155
C27—H27···O1^vi	0.95	2.53	3.4505 (16)	163

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

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

Contact	Distance	Symmetry operation
O5···H9	2.49	1 - x, 2 - y, 1 - z
O5···H13A	2.40	1 - x, 2 - y, 1 - z
Cl2···C14	3.21	-1 + x, -1 + y, 1 + z
Cl2···O2	3.22	-1 + x, -1 + y, 1 + z
O1···H27	2.92	1 - x, 1 - y, 1 - z
O1···H4N^b	1.96	x, y, z
O2···H2N^b	2.00	-1 + x, y, z
O5···H8	2.46	x, y, z
N3···H6O^b	1.67	x, y, z
O3···H2	2.42	1 - x, 2 - y, 1 - z
O3···H6A	2.51	1 - x, 2 - y, 1 - z
C7···Cl1	3.25	x, 1 + y, -1 + z
N1···H4O^b	1.68	-1 + x, y, z
O3···H1	2.60	-1 + x, y, z
O1···Cl1	3.24	x, 1 + 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 mol¹) calculated for (I) top

Contact	E_ele	E_pol	E_dis	E_rep	E_tot	Symmetry operation
N2—H2N···O2/
N4—H4N···O1	-51.0	-12.4	-49.4	71.6	-61.9	x, y, z
O4—H4O···N1/
C1—H1···O3	-84.3	-20.1	-12.7	106.3	-49.4	-1 + x, y, z
O6—H6O···N3/
C8—H8···O5	-90.9	-21.4	-13.1	115.6	-52.0	x, y, z
C7···Cl1/ O1···Cl1	-5.3	-1.0	-25.4	19.3	-16.6	x, 1 + y, -1 + z
C6—H6A···O3/
C2—H2···O3	-11.9	-3.2	-12.5	16.5	-15.8	1 - x, 2 - y, 1 - z
C9—H9···O5/
C13—H13A···O5	-12.8	-3.6	-13.3	18.5	-16.3	1 - x, 2 - y, 1 - z
C14···Cl2/ O2···Cl2	-6.6	-0.8	-27.3	27.2	-14.5	-1 + x, -1 + y, 1 + z
C25—H25···Cl2	-6.4	-0.7	-13.5	16.7	-8.7	-x, - y, - z
C27—H27···O1	-10.4	-1.6	-23.4	19.7	-20.4	1 - x, 1 - y, 1 - z

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

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