The design of novel metronidazole benzoate structures: exploring stoichiometric diversity

Santiago de Oliveira, Y.; Saraiva Costa, W.; Ferreira Borges, P.; Silmara Alves de Santana, M.; Ayala, A.P.

doi:10.1107/S2053229619003838

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The design of novel metronidazole benzoate structures: exploring stoichiometric diversity

Y. Santiago de Oliveira, W. Saraiva Costa, P. Ferreira Borges, M. Silmara Alves de Santana and A. P. Ayala

The use of supramolecular synthons as a strategy to control crystalline structure is a crucial factor in developing new solid forms with physicochemical properties optimized by design. However, to achieve this objective, it is necessary to understand the intermolecular interactions in the context of crystal packing. The feasibility of a given synthon depends on its flexibility to combine the drug with a variety of coformers. In the present work, the imidazole–hydroxy synthon is investigated using as the target molecule benzoylmetronidazole [BZMD; systematic name 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate], whose imidazole group seems to be a suitable acceptor for hydrogen bonds. Thus, coformers with carboxylic acid and phenol groups were chosen. According to the availability of binding sites presented in the coformer, and considering the proposed synthon and hydrogen-bond complementarity as major factors, different drug–coformer stoichiometric ratios were explored (1:1, 2:1 and 3:1). Thirteen new solid forms (two salts and eleven cocrystals) were produced, namely BZMD–benzoic acid (1/1), C₁₃H₁₃N₃O₄·C₇H₆O₂, BZMD–β-naphthol (1/1), C₁₃H₁₃N₃O₄·C₁₀H₈O, BZMD–4-methoxybenzoic acid (1/1), C₁₃H₁₃N₃O₄·C₈H₈O₃, BZMD–3,5-dinitrobenzoic acid (1/1), C₁₃H₁₃N₃O₄·C₇H₄N₂O₆, BZMD–3-aminobenzoic acid (1/1), C₁₃H₁₃N₃O₄·C₇H₇NO₂, BZMD–salicylic acid (1/1), C₁₃H₁₃N₃O₄·C₇H₆O₃, BZMD–maleic acid (1/1) {as the salt 1-[2-(benzoyloxy)ethyl]-2-methyl-5-nitro-1H-imidazol-3-ium 3-carboxyprop-2-enoate}, C₁₃H₁₄N₃O₄⁺·C₄H₃O₄⁻, BZMD–isophthalic acid (1/1), C₁₃H₁₃N₃O₄·C₈H₆O4, BZMD–resorcinol (2/1), 2C₁₃H₁₃N₃O₄·C₆H₆O₂, BZMD–fumaric acid (2/1), C₁₃H₁₃N₃O₄·0.5C₄H₄O₄, BZMD–malonic acid (2/1), 2C₁₃H₁₃N₃O₄·C₃H₂O₄, BZMD–2,6-dihydroxybenzoic acid (1/1) {as the salt 1-[2-(benzoyloxy)ethyl]-2-methyl-5-nitro-1H-imidazol-3-ium 2,6-dihydroxybenzoate}, C₁₃H₁₄N₃O₄⁺·C₇H₅O₄⁻, and BZMD–3,5-dihydroxybenzoic acid (3/1), 3C₁₃H₁₃N₃O₄·C₇H₆O₄, and their crystalline structures elucidated, confirming the robustness of the selected synthon.

Keywords: metronidazole benzoate; crystal engineering; cocrystal; salt; physicochemical; crystal structure; pharmaceutical; API; cocrystal.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619003838/jx3032sup1.cif Contains datablocks bzmdbzc, bzmdnaf, bzmdmac, bzmd35dnz, bzmdabn, bzmdslc, bzmdmlc, bzmdiac, bzmdres, bzmdfma, bzmdmln, bzmd26dba, bzmd35dba, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdbzcsup2.hkl Contains datablock bzmdbzc
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdnafsup3.hkl Contains datablock bzmdnaf
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdmacsup4.hkl Contains datablock bzmdmac
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmd35dnzsup5.hkl Contains datablock bzmd35dnz
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdabnsup6.hkl Contains datablock bzmdabn
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdslcsup7.hkl Contains datablock bzmdslc
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdmlcsup8.hkl Contains datablock bzmdmlc
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdiacsup9.hkl Contains datablock bzmdiac
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdressup10.hkl Contains datablock bzmdres
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdfmasup11.hkl Contains datablock bzmdfma
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdmlnsup12.hkl Contains datablock bzmdmln
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmd26dbasup13.hkl Contains datablock bzmd26dba
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdbzcsup14.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmd35dbasup14.hkl Contains datablock bzmd35dba
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdnafsup15.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdmacsup16.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmd35dnzsup17.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdabnsup18.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdslcsup19.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdmlcsup20.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdiacsup21.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmd26dbasup22.cml Supplementary material
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619003838/jx3032sup23.pdf Hydrogen-bonding details, list of coformers and stoichiometry, and displacement ellipsoid plots

CCDC references: 1890422; 1890421; 1890430; 1890426; 1890432; 1890427; 1890429; 1890433; 1890424; 1890423; 1890428; 1890431; 1890425

Computing details top

For all structures, data collection: APEX3 (Bruker, 2012); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009), Mercury (Version 3.10; Macrae et al., 2008) and VEGA (Pedretti et al., 2004); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–benzoic acid (1/1) (bzmdbzc) top

Crystal data top

C₁₃H₁₃N₃O₄·C₇H₆O₂	F(000) = 832
M_r = 397.38	D_x = 1.366 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 13.5997 (6) Å	Cell parameters from 9997 reflections
b = 9.0354 (4) Å	θ = 5.1–68.0°
c = 16.5974 (8) Å	µ = 0.86 mm⁻¹
β = 108.646 (2)°	T = 300 K
V = 1932.42 (15) Å³	Prism, clear light colourless
Z = 4	0.8 × 0.2 × 0.2 mm

Data collection top

Bruker APEXII CCD diffractometer	2669 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.053
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 68.3°, θ_min = 3.7°
T_min = 0.675, T_max = 0.753	h = −16→16
60527 measured reflections	k = −10→10
3542 independent reflections	l = −19→20

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.045	w = 1/[σ²(F_o²) + (0.0462P)² + 0.7992P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.130	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.16 e Å⁻³
3542 reflections	Δρ_min = −0.14 e Å⁻³
339 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0027 (4)

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.

Refinement. Single-crystal X-ray diffraction data collection (ϕ scans and ω scans with κ and θ offsets) were performed at room temperature on a Bruker D8 VENTURE equipped with a Kappa goniometer, PHOTON II CPAD detector, a Mo Kα INCOATEC IµS 3.0 microfocus source (λ = 0.71073 Å). The crystal centring, unit-cell determination, refinement of the unit-cell parameters and data collection was controlled through the program APEX3 (Bruker, 2012). The frame integration was performed using SAINT (Bruker, 2016) and the intensities were scaled and absorption corrected using SADABS (Bruker, 2001). Using OLEX2 (Dolomanov et al., 2009), the structure was solved by intrinsic phasing using SHELXT (Sheldrick, 2015) and refined by full-matrix least-squares calculation based on F² for all reflection using SHELXL (Sheldrick, 2007). All non-H atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O3	0.57161 (11)	0.97707 (18)	0.14818 (9)	0.0723 (4)
O1'	0.65654 (13)	0.60123 (18)	0.53629 (11)	0.0806 (5)
N1	0.62802 (12)	0.99073 (17)	0.32969 (9)	0.0568 (4)
O2'	0.52139 (13)	0.69513 (19)	0.56528 (12)	0.0887 (5)
N3	0.79953 (14)	0.9851 (2)	0.30460 (11)	0.0681 (5)
O1	0.87927 (13)	0.9118 (2)	0.31765 (12)	0.0933 (5)
N2	0.65260 (13)	0.80491 (19)	0.42084 (11)	0.0655 (5)
O4	0.43536 (12)	0.8503 (2)	0.06689 (11)	0.0930 (6)
O2	0.78341 (14)	1.1005 (2)	0.26413 (12)	0.0933 (6)
C1'	0.61614 (14)	0.4999 (2)	0.65137 (12)	0.0543 (4)
C1	0.72512 (15)	0.9308 (2)	0.34107 (12)	0.0584 (5)
C8	0.60097 (15)	0.8057 (2)	0.05160 (12)	0.0605 (5)
C7'	0.59173 (15)	0.6076 (2)	0.57987 (12)	0.0587 (5)
C3	0.58695 (16)	0.9091 (2)	0.37957 (12)	0.0587 (5)
C6'	0.54581 (18)	0.4792 (2)	0.69523 (14)	0.0660 (5)
C2'	0.70976 (16)	0.4248 (2)	0.67683 (15)	0.0670 (5)
C7	0.52666 (16)	0.8765 (3)	0.08774 (12)	0.0642 (5)
C2	0.73912 (17)	0.8177 (2)	0.39708 (14)	0.0660 (5)
C5	0.5730 (2)	1.1090 (2)	0.27249 (15)	0.0692 (6)
C9	0.5671 (2)	0.6840 (3)	−0.00055 (15)	0.0765 (6)
C4	0.4827 (2)	0.9323 (3)	0.38706 (18)	0.0732 (6)
C6	0.50507 (19)	1.0484 (3)	0.18877 (14)	0.0755 (6)
C5'	0.5698 (2)	0.3854 (3)	0.76467 (15)	0.0746 (6)
C13	0.70145 (18)	0.8566 (3)	0.06717 (15)	0.0725 (6)
C4'	0.6644 (2)	0.3150 (3)	0.79135 (16)	0.0786 (7)
C12	0.7663 (2)	0.7852 (3)	0.03012 (18)	0.0836 (7)
C11	0.7312 (2)	0.6645 (3)	−0.02131 (17)	0.0872 (8)
C3'	0.7339 (2)	0.3331 (3)	0.74715 (17)	0.0807 (7)
C10	0.6321 (2)	0.6133 (3)	−0.03665 (18)	0.0900 (8)
H9	0.497 (2)	0.656 (3)	−0.0102 (16)	0.086 (7)*
H12	0.838 (2)	0.821 (3)	0.0425 (18)	0.107 (9)*
H11	0.774 (2)	0.614 (3)	−0.0500 (16)	0.095 (8)*
H2'	0.7584 (18)	0.435 (3)	0.6439 (14)	0.080 (7)*
H4'	0.679 (2)	0.249 (3)	0.8403 (18)	0.105 (9)*
H6'	0.477 (2)	0.532 (3)	0.6729 (15)	0.092 (8)*
H5'	0.520 (2)	0.375 (3)	0.7942 (16)	0.094 (8)*
H3'	0.801 (2)	0.276 (3)	0.7636 (18)	0.111 (9)*
H13	0.7269 (19)	0.943 (3)	0.1044 (16)	0.087 (8)*
H2	0.8006 (19)	0.756 (3)	0.4194 (15)	0.083 (7)*
H6A	0.450 (2)	0.972 (3)	0.1934 (17)	0.101 (9)*
H6B	0.468 (2)	1.128 (3)	0.1501 (17)	0.098 (8)*
H1'	0.647 (2)	0.681 (4)	0.494 (2)	0.138 (12)*
H5A	0.6277 (18)	1.174 (3)	0.2639 (15)	0.081 (7)*
H5B	0.5303 (18)	1.163 (3)	0.3013 (15)	0.079 (7)*
H4A	0.474 (2)	0.864 (3)	0.4331 (19)	0.110 (9)*
H4B	0.428 (2)	0.917 (3)	0.336 (2)	0.109 (10)*
H4C	0.476 (2)	1.031 (4)	0.4081 (17)	0.102 (9)*
H10	0.608 (2)	0.526 (4)	−0.072 (2)	0.123 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0652 (9)	0.0906 (11)	0.0624 (8)	−0.0003 (8)	0.0223 (7)	−0.0020 (8)
O1'	0.0944 (11)	0.0741 (10)	0.0880 (11)	0.0183 (8)	0.0497 (9)	0.0230 (9)
N1	0.0661 (10)	0.0539 (9)	0.0508 (8)	0.0004 (7)	0.0194 (7)	0.0009 (7)
O2'	0.0776 (10)	0.0867 (12)	0.1086 (13)	0.0266 (9)	0.0395 (9)	0.0356 (10)
N3	0.0712 (11)	0.0709 (11)	0.0642 (10)	−0.0079 (9)	0.0246 (9)	−0.0045 (9)
O1	0.0775 (11)	0.0989 (13)	0.1149 (14)	0.0056 (10)	0.0466 (10)	0.0036 (11)
N2	0.0694 (10)	0.0638 (10)	0.0634 (10)	−0.0010 (8)	0.0213 (8)	0.0078 (8)
O4	0.0621 (9)	0.1282 (15)	0.0868 (11)	−0.0115 (10)	0.0211 (8)	−0.0059 (11)
O2	0.0977 (12)	0.0898 (12)	0.0998 (13)	−0.0056 (10)	0.0421 (10)	0.0267 (10)
C1'	0.0576 (10)	0.0471 (10)	0.0568 (10)	−0.0020 (8)	0.0164 (8)	−0.0019 (8)
C1	0.0622 (11)	0.0585 (11)	0.0560 (11)	−0.0049 (9)	0.0211 (9)	−0.0028 (9)
C8	0.0641 (11)	0.0678 (12)	0.0490 (10)	−0.0042 (9)	0.0171 (9)	0.0126 (9)
C7'	0.0580 (11)	0.0538 (11)	0.0630 (12)	−0.0023 (9)	0.0173 (9)	0.0011 (9)
C3	0.0682 (12)	0.0574 (11)	0.0519 (10)	−0.0038 (9)	0.0211 (9)	−0.0028 (9)
C6'	0.0706 (13)	0.0630 (12)	0.0693 (13)	0.0057 (10)	0.0293 (11)	0.0018 (10)
C2'	0.0599 (12)	0.0633 (12)	0.0773 (14)	0.0022 (10)	0.0211 (10)	0.0091 (10)
C7	0.0631 (12)	0.0762 (14)	0.0506 (11)	−0.0043 (10)	0.0144 (9)	0.0122 (10)
C2	0.0655 (12)	0.0642 (12)	0.0668 (13)	0.0012 (10)	0.0192 (10)	0.0044 (10)
C5	0.0848 (15)	0.0568 (12)	0.0707 (14)	0.0127 (11)	0.0315 (12)	0.0103 (10)
C9	0.0744 (15)	0.0848 (16)	0.0674 (13)	−0.0092 (13)	0.0188 (11)	0.0021 (12)
C4	0.0734 (14)	0.0808 (16)	0.0712 (15)	0.0014 (12)	0.0311 (12)	0.0003 (13)
C6	0.0740 (14)	0.0941 (17)	0.0592 (12)	0.0181 (13)	0.0223 (11)	0.0103 (12)
C5'	0.0915 (16)	0.0737 (14)	0.0683 (13)	0.0026 (12)	0.0394 (13)	0.0054 (11)
C13	0.0696 (13)	0.0772 (15)	0.0733 (14)	−0.0081 (12)	0.0263 (11)	0.0079 (12)
C4'	0.0926 (17)	0.0731 (15)	0.0672 (14)	0.0018 (13)	0.0215 (12)	0.0134 (12)
C12	0.0728 (15)	0.0937 (19)	0.0905 (17)	−0.0004 (13)	0.0351 (13)	0.0171 (15)
C11	0.100 (2)	0.0925 (19)	0.0790 (16)	0.0190 (16)	0.0419 (15)	0.0129 (14)
C3'	0.0693 (14)	0.0779 (15)	0.0886 (16)	0.0102 (12)	0.0165 (12)	0.0210 (13)
C10	0.100 (2)	0.0892 (19)	0.0812 (17)	0.0005 (16)	0.0299 (15)	−0.0058 (14)

Geometric parameters (Å, º) top

O3—C7	1.347 (3)	C1'—C2'	1.384 (3)
O3—C6	1.441 (3)	C1—C2	1.353 (3)
O1'—C7'	1.308 (2)	C8—C7	1.476 (3)
N1—C1	1.383 (2)	C8—C9	1.384 (3)
N1—C3	1.355 (2)	C8—C13	1.386 (3)
N1—C5	1.466 (3)	C3—C4	1.477 (3)
O2'—C7'	1.205 (2)	C6'—C5'	1.383 (3)
N3—O1	1.230 (2)	C2'—C3'	1.382 (3)
N3—O2	1.221 (2)	C5—C6	1.504 (3)
N3—C1	1.422 (3)	C9—C10	1.374 (4)
N2—C3	1.327 (3)	C5'—C4'	1.376 (3)
N2—C2	1.360 (3)	C13—C12	1.385 (4)
O4—C7	1.201 (2)	C4'—C3'	1.379 (4)
C1'—C7'	1.488 (3)	C12—C11	1.373 (4)
C1'—C6'	1.387 (3)	C11—C10	1.370 (4)

C7—O3—C6	116.51 (17)	N1—C3—C4	124.6 (2)
C1—N1—C5	129.89 (17)	N2—C3—N1	111.14 (17)
C3—N1—C1	105.40 (16)	N2—C3—C4	124.22 (19)
C3—N1—C5	124.57 (18)	C5'—C6'—C1'	120.1 (2)
O1—N3—C1	116.53 (19)	C3'—C2'—C1'	119.9 (2)
O2—N3—O1	123.4 (2)	O3—C7—C8	112.86 (17)
O2—N3—C1	120.10 (19)	O4—C7—O3	121.9 (2)
C3—N2—C2	106.95 (17)	O4—C7—C8	125.2 (2)
C6'—C1'—C7'	119.43 (18)	C1—C2—N2	108.58 (19)
C2'—C1'—C7'	120.86 (18)	N1—C5—C6	111.62 (19)
C2'—C1'—C6'	119.65 (19)	C10—C9—C8	120.7 (2)
N1—C1—N3	125.81 (18)	O3—C6—C5	107.62 (19)
C2—C1—N1	107.93 (18)	C4'—C5'—C6'	119.9 (2)
C2—C1—N3	126.15 (19)	C12—C13—C8	119.5 (3)
C9—C8—C7	117.7 (2)	C5'—C4'—C3'	120.2 (2)
C9—C8—C13	119.5 (2)	C11—C12—C13	120.1 (3)
C13—C8—C7	122.9 (2)	C10—C11—C12	120.6 (3)
O1'—C7'—C1'	113.23 (17)	C4'—C3'—C2'	120.2 (2)
O2'—C7'—O1'	123.35 (19)	C11—C10—C9	119.6 (3)
O2'—C7'—C1'	123.38 (19)

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–β-naphthol (1/1) (bzmdnaf) top

Crystal data top

C₁₃H₁₃N₃O₄·C₁₀H₈O	F(000) = 880
M_r = 419.43	D_x = 1.311 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 8.5105 (8) Å	Cell parameters from 9803 reflections
b = 22.387 (2) Å	θ = 4.4–69.6°
c = 11.7752 (11) Å	µ = 0.78 mm⁻¹
β = 108.664 (4)°	T = 300 K
V = 2125.4 (3) Å³	Prism, clear light yellow
Z = 4	0.42 × 0.09 × 0.07 mm

Data collection top

Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer	2810 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.084
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 68.3°, θ_min = 4.0°
T_min = 0.678, T_max = 1.000	h = −10→10
39131 measured reflections	k = −26→26
3884 independent reflections	l = −14→13

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.058	w = 1/[σ²(F_o²) + (0.1113P)² + 0.4215P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.193	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.30 e Å⁻³
3884 reflections	Δρ_min = −0.23 e Å⁻³
365 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0041 (7)

Special details top

Refinement. Single-crystal X-ray diffraction data collection (ϕ scans and ω scans with κ and θ offsets) were performed at room temperature on a Bruker AXS D8 VENTURE equipped with a Kappa goniometer, PHOTON II CPAD detector, a Mo Kα INCOATEC IµS 3.0 microfocus source (λ = 0.71073 Å). The crystal centring, unit-cell determination, refinement of the unit-cell parameters and data collection was controlled through the program APEX3 (Bruker, 2012). The frame integration was performed using SAINT (Bruker, 2016) and the intensities were scaled and absorption corrected using SADABS (Bruker, 2001). Using OLEX2 (Dolomanov et al., 2009), the structure was solved by intrinsic phasing using SHELXT (Sheldrick, 2015) and refined by full-matrix least-squares calculation based on F² for all reflection using SHELXL (Sheldrick, 2007). All non-H atoms were refined anisotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O3	−0.36072 (19)	0.49428 (7)	0.19944 (13)	0.0624 (4)
O2	−0.2808 (2)	0.51266 (9)	0.57654 (16)	0.0842 (6)
N1	−0.2220 (2)	0.58230 (8)	0.39335 (15)	0.0563 (4)
O1	−0.0234 (3)	0.52273 (9)	0.68439 (16)	0.0850 (6)
O1'	0.2411 (3)	0.70227 (10)	0.35022 (19)	0.0908 (6)
N3	−0.1417 (3)	0.53251 (9)	0.59314 (17)	0.0652 (5)
O4	−0.3769 (3)	0.39564 (9)	0.21856 (18)	0.0892 (6)
N2	0.0181 (2)	0.62642 (9)	0.40900 (18)	0.0681 (5)
C1	−0.1092 (3)	0.56838 (9)	0.50416 (18)	0.0562 (5)
C3	−0.1374 (3)	0.61722 (10)	0.3393 (2)	0.0634 (6)
C8	−0.2958 (3)	0.43345 (12)	0.05661 (19)	0.0658 (6)
C2	0.0348 (3)	0.59617 (11)	0.5115 (2)	0.0649 (6)
C7	−0.3486 (3)	0.43791 (11)	0.1652 (2)	0.0633 (6)
C10'	0.4667 (3)	0.67583 (11)	0.5266 (2)	0.0675 (6)
C5	−0.3963 (3)	0.56412 (11)	0.3424 (2)	0.0645 (6)
C9'	0.6381 (3)	0.67996 (10)	0.5925 (2)	0.0688 (6)
C1'	0.4025 (3)	0.70428 (11)	0.4195 (2)	0.0727 (7)
C6	−0.4166 (3)	0.50046 (11)	0.3028 (2)	0.0623 (6)
C9	−0.2418 (3)	0.48176 (15)	0.0078 (2)	0.0772 (7)
C4'	0.7415 (3)	0.71446 (11)	0.5461 (3)	0.0799 (8)
C4	−0.2096 (5)	0.64272 (17)	0.2172 (3)	0.0859 (8)
C13	−0.2986 (4)	0.37744 (15)	0.0059 (2)	0.0836 (8)
C8'	0.7088 (4)	0.65030 (14)	0.7035 (3)	0.0846 (8)
C2'	0.5090 (5)	0.73895 (14)	0.3747 (4)	0.0921 (9)
C3'	0.6720 (4)	0.74335 (14)	0.4367 (4)	0.0989 (11)
C12	−0.2455 (5)	0.37083 (19)	−0.0939 (3)	0.0984 (10)
C11	−0.1911 (4)	0.4196 (2)	−0.1412 (3)	0.0977 (10)
C5'	0.9152 (4)	0.71857 (15)	0.6162 (5)	0.1008 (12)
C10	−0.1889 (4)	0.47476 (19)	−0.0920 (3)	0.0913 (9)
C6'	0.9762 (5)	0.68936 (17)	0.7222 (4)	0.1071 (12)
C7'	0.8736 (4)	0.65473 (17)	0.7664 (3)	0.0969 (10)
H5A	−0.448 (4)	0.5694 (12)	0.403 (3)	0.082 (8)*
H10'	0.394 (3)	0.6541 (11)	0.559 (2)	0.070 (7)*
H6A	−0.540 (4)	0.4903 (11)	0.280 (2)	0.076 (7)*
H5B	−0.448 (3)	0.5927 (11)	0.277 (2)	0.071 (7)*
H6B	−0.355 (3)	0.4734 (12)	0.365 (2)	0.071 (7)*
H8'	0.629 (5)	0.6273 (16)	0.736 (3)	0.125 (12)*
H10	−0.146 (4)	0.5098 (15)	−0.128 (3)	0.112 (11)*
H13	−0.341 (4)	0.3442 (15)	0.041 (3)	0.096 (10)*
H9	−0.246 (4)	0.5203 (15)	0.043 (3)	0.095 (10)*
H1'	0.180 (4)	0.6777 (16)	0.382 (3)	0.107 (11)*
H2	0.134 (4)	0.5959 (12)	0.575 (3)	0.083 (8)*
H4A	−0.132 (5)	0.6636 (18)	0.200 (3)	0.122 (13)*
H3'	0.751 (4)	0.7664 (16)	0.413 (3)	0.113 (10)*
H6'	1.104 (5)	0.6919 (18)	0.771 (3)	0.133 (13)*
H12	−0.249 (5)	0.3291 (18)	−0.124 (3)	0.124 (12)*
H4B	−0.267 (5)	0.6107 (19)	0.157 (4)	0.138 (14)*
H11	−0.150 (4)	0.4097 (16)	−0.213 (3)	0.120 (11)*
H2'	0.458 (4)	0.7552 (16)	0.306 (3)	0.102 (11)*
H4C	−0.304 (6)	0.670 (2)	0.212 (4)	0.148 (15)*
H5'	0.974 (4)	0.7413 (15)	0.573 (3)	0.104 (10)*
H7'	0.937 (6)	0.634 (2)	0.855 (5)	0.170 (18)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0638 (9)	0.0724 (10)	0.0572 (8)	−0.0028 (7)	0.0280 (7)	0.0008 (7)
O2	0.0876 (13)	0.1041 (14)	0.0733 (11)	−0.0111 (10)	0.0431 (10)	0.0035 (9)
N1	0.0562 (9)	0.0573 (10)	0.0581 (10)	0.0053 (8)	0.0221 (8)	0.0002 (8)
O1	0.0934 (13)	0.0978 (14)	0.0590 (10)	0.0078 (10)	0.0177 (9)	0.0115 (9)
O1'	0.0843 (13)	0.0958 (14)	0.0938 (13)	0.0026 (10)	0.0305 (11)	0.0253 (11)
N3	0.0746 (13)	0.0691 (12)	0.0586 (11)	0.0051 (10)	0.0308 (10)	−0.0026 (9)
O4	0.1245 (16)	0.0762 (11)	0.0852 (12)	−0.0154 (10)	0.0589 (11)	−0.0029 (9)
N2	0.0683 (12)	0.0661 (12)	0.0741 (12)	−0.0026 (9)	0.0287 (10)	0.0014 (9)
C1	0.0613 (12)	0.0563 (11)	0.0538 (11)	0.0060 (9)	0.0226 (9)	0.0004 (9)
C3	0.0694 (14)	0.0577 (12)	0.0677 (13)	0.0034 (10)	0.0286 (11)	0.0043 (10)
C8	0.0571 (12)	0.0904 (17)	0.0500 (11)	0.0015 (11)	0.0173 (9)	−0.0006 (10)
C2	0.0649 (14)	0.0645 (13)	0.0660 (14)	0.0048 (11)	0.0219 (11)	−0.0037 (11)
C7	0.0619 (13)	0.0732 (15)	0.0581 (12)	−0.0052 (11)	0.0239 (10)	−0.0017 (10)
C10'	0.0707 (14)	0.0613 (13)	0.0796 (15)	−0.0055 (11)	0.0368 (12)	−0.0040 (11)
C5	0.0541 (12)	0.0740 (15)	0.0679 (14)	0.0079 (11)	0.0230 (11)	0.0019 (11)
C9'	0.0758 (15)	0.0580 (13)	0.0816 (16)	−0.0034 (11)	0.0381 (12)	−0.0181 (11)
C1'	0.0757 (16)	0.0597 (13)	0.0914 (17)	0.0017 (11)	0.0390 (14)	0.0034 (12)
C6	0.0593 (13)	0.0755 (15)	0.0585 (13)	−0.0031 (11)	0.0278 (10)	−0.0014 (11)
C9	0.0732 (15)	0.103 (2)	0.0595 (14)	−0.0112 (14)	0.0272 (12)	−0.0008 (13)
C4'	0.0784 (17)	0.0543 (13)	0.121 (2)	−0.0065 (12)	0.0508 (16)	−0.0169 (14)
C4	0.094 (2)	0.088 (2)	0.0754 (17)	−0.0009 (18)	0.0263 (16)	0.0244 (15)
C13	0.0924 (19)	0.094 (2)	0.0640 (15)	0.0123 (16)	0.0245 (14)	−0.0047 (14)
C8'	0.0856 (18)	0.0873 (19)	0.0835 (18)	−0.0045 (15)	0.0306 (15)	−0.0211 (15)
C2'	0.106 (2)	0.0732 (17)	0.113 (2)	0.0034 (16)	0.057 (2)	0.0197 (17)
C3'	0.096 (2)	0.0680 (17)	0.157 (3)	−0.0086 (15)	0.075 (2)	0.0096 (18)
C12	0.103 (2)	0.123 (3)	0.0663 (16)	0.030 (2)	0.0229 (16)	−0.0136 (17)
C11	0.0785 (18)	0.157 (3)	0.0607 (16)	0.0163 (19)	0.0268 (13)	0.0002 (19)
C5'	0.083 (2)	0.0666 (17)	0.168 (4)	−0.0161 (15)	0.062 (2)	−0.032 (2)
C10	0.0742 (17)	0.140 (3)	0.0655 (16)	−0.0110 (17)	0.0302 (13)	0.0037 (18)
C6'	0.085 (2)	0.088 (2)	0.138 (3)	−0.0008 (18)	0.021 (2)	−0.042 (2)
C7'	0.0807 (19)	0.100 (2)	0.104 (2)	−0.0034 (17)	0.0213 (17)	−0.0365 (19)

Geometric parameters (Å, º) top

O3—C7	1.339 (3)	C1'—C2'	1.417 (4)
O3—C6	1.448 (3)	C6—H6A	1.02 (3)
O2—N3	1.221 (3)	C6—H6B	0.96 (3)
N1—C1	1.385 (3)	C9—C10	1.395 (4)
N1—C3	1.352 (3)	C9—H9	0.96 (3)
N1—C5	1.468 (3)	C4'—C3'	1.393 (5)
O1—N3	1.234 (3)	C4'—C5'	1.447 (5)
O1'—C1'	1.356 (3)	C4—H4A	0.88 (4)
O1'—H1'	0.91 (4)	C4—H4B	1.02 (5)
N3—C1	1.416 (3)	C4—H4C	1.00 (5)
O4—C7	1.202 (3)	C13—C12	1.395 (4)
N2—C3	1.332 (3)	C13—H13	0.98 (3)
N2—C2	1.351 (3)	C8'—C7'	1.364 (4)
C1—C2	1.352 (3)	C8'—H8'	1.02 (4)
C3—C4	1.484 (4)	C2'—C3'	1.348 (5)
C8—C7	1.488 (3)	C2'—H2'	0.87 (3)
C8—C9	1.371 (4)	C3'—H3'	0.95 (4)
C8—C13	1.386 (4)	C12—C11	1.372 (5)
C2—H2	0.93 (3)	C12—H12	1.00 (4)
C10'—C9'	1.419 (4)	C11—C10	1.362 (5)
C10'—C1'	1.361 (4)	C11—H11	1.04 (4)
C10'—H10'	0.95 (3)	C5'—C6'	1.356 (6)
C5—C6	1.492 (3)	C5'—H5'	0.96 (3)
C5—H5A	0.95 (3)	C10—H10	1.01 (4)
C5—H5B	0.99 (3)	C6'—C7'	1.388 (6)
C9'—C4'	1.406 (4)	C6'—H6'	1.05 (4)
C9'—C8'	1.418 (4)	C7'—H7'	1.11 (5)

C7—O3—C6	114.89 (17)	H6A—C6—H6B	109 (2)
C1—N1—C5	128.84 (19)	C8—C9—C10	120.4 (3)
C3—N1—C1	105.12 (18)	C8—C9—H9	117.6 (19)
C3—N1—C5	126.04 (19)	C10—C9—H9	122 (2)
C1'—O1'—H1'	112 (2)	C9'—C4'—C5'	117.7 (3)
O2—N3—O1	123.6 (2)	C3'—C4'—C9'	118.7 (3)
O2—N3—C1	119.8 (2)	C3'—C4'—C5'	123.5 (3)
O1—N3—C1	116.5 (2)	C3—C4—H4A	109 (3)
C3—N2—C2	105.8 (2)	C3—C4—H4B	111 (2)
N1—C1—N3	125.74 (19)	C3—C4—H4C	112 (3)
C2—C1—N1	107.28 (19)	H4A—C4—H4B	116 (3)
C2—C1—N3	127.0 (2)	H4A—C4—H4C	107 (4)
N1—C3—C4	124.1 (2)	H4B—C4—H4C	101 (4)
N2—C3—N1	111.9 (2)	C8—C13—C12	119.5 (3)
N2—C3—C4	124.0 (2)	C8—C13—H13	117.7 (19)
C9—C8—C7	122.8 (2)	C12—C13—H13	122.7 (19)
C9—C8—C13	119.7 (2)	C9'—C8'—H8'	116 (2)
C13—C8—C7	117.5 (2)	C7'—C8'—C9'	121.7 (3)
N2—C2—C1	109.9 (2)	C7'—C8'—H8'	122 (2)
N2—C2—H2	121.8 (18)	C1'—C2'—H2'	113 (2)
C1—C2—H2	128.3 (18)	C3'—C2'—C1'	120.5 (3)
O3—C7—C8	113.3 (2)	C3'—C2'—H2'	126 (2)
O4—C7—O3	122.5 (2)	C4'—C3'—H3'	113 (2)
O4—C7—C8	124.2 (2)	C2'—C3'—C4'	121.7 (3)
C9'—C10'—H10'	119.9 (15)	C2'—C3'—H3'	125 (2)
C1'—C10'—C9'	120.9 (2)	C13—C12—H12	115 (2)
C1'—C10'—H10'	119.1 (15)	C11—C12—C13	120.0 (3)
N1—C5—C6	113.15 (19)	C11—C12—H12	125 (2)
N1—C5—H5A	107.8 (17)	C12—C11—H11	114 (2)
N1—C5—H5B	106.3 (14)	C10—C11—C12	120.6 (3)
C6—C5—H5A	108.5 (17)	C10—C11—H11	125 (2)
C6—C5—H5B	113.1 (14)	C4'—C5'—H5'	110 (2)
H5A—C5—H5B	108 (2)	C6'—C5'—C4'	121.0 (3)
C4'—C9'—C10'	119.0 (3)	C6'—C5'—H5'	129 (2)
C4'—C9'—C8'	118.8 (3)	C9—C10—H10	121 (2)
C8'—C9'—C10'	122.2 (2)	C11—C10—C9	119.8 (3)
O1'—C1'—C10'	124.8 (2)	C11—C10—H10	119 (2)
O1'—C1'—C2'	116.1 (3)	C5'—C6'—C7'	120.9 (4)
C10'—C1'—C2'	119.1 (3)	C5'—C6'—H6'	120 (2)
O3—C6—C5	108.53 (19)	C7'—C6'—H6'	119 (2)
O3—C6—H6A	110.0 (15)	C8'—C7'—C6'	119.9 (4)
O3—C6—H6B	109.4 (15)	C8'—C7'—H7'	126 (3)
C5—C6—H6A	107.5 (14)	C6'—C7'—H7'	114 (3)
C5—C6—H6B	112.5 (15)

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–4-methoxybenzoic acid (1/1) (bzmdmac) top

Crystal data top

C₁₃H₁₃N₃O₄·C₈H₈O₃	Z = 2
M_r = 427.41	F(000) = 448
Triclinic, P1	D_x = 1.416 Mg m⁻³
a = 9.1309 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1274 (4) Å	Cell parameters from 9919 reflections
c = 11.8538 (5) Å	θ = 2.5–27.5°
α = 107.365 (1)°	µ = 0.11 mm⁻¹
β = 103.270 (1)°	T = 300 K
γ = 110.091 (1)°	Plate, clear light colourless
V = 1002.73 (7) Å³	0.73 × 0.49 × 0.21 mm

Data collection top

Bruker APEX3 microsource diffractometer	3795 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.063
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 27.5°, θ_min = 3.6°
T_min = 0.587, T_max = 0.746	h = −11→11
32021 measured reflections	k = −14→14
4583 independent reflections	l = −15→15

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.059	All H-atom parameters refined
wR(F²) = 0.165	w = 1/[σ²(F_o²) + (0.0785P)² + 0.4129P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4583 reflections	Δρ_max = 0.76 e Å⁻³
364 parameters	Δρ_min = −0.24 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O3	0.25372 (18)	0.92488 (15)	0.54618 (12)	0.0501 (3)
O1'	0.8663 (2)	0.60162 (19)	0.82192 (14)	0.0593 (4)
O3'	1.3864 (2)	0.35358 (17)	0.84208 (14)	0.0603 (4)
O2'	0.8625 (2)	0.56494 (18)	0.62520 (14)	0.0617 (4)
O4	0.3621 (2)	0.82888 (18)	0.41261 (14)	0.0592 (4)
O2	0.2647 (2)	0.86239 (18)	0.88018 (15)	0.0624 (4)
O1	0.4097 (2)	0.84360 (19)	1.03975 (14)	0.0675 (5)
N1	0.43006 (18)	0.75915 (15)	0.73271 (14)	0.0395 (3)
N3	0.3715 (2)	0.83160 (16)	0.92979 (14)	0.0442 (4)
N2	0.63325 (19)	0.70185 (17)	0.79998 (15)	0.0463 (4)
C2'	1.0933 (2)	0.44853 (18)	0.66222 (16)	0.0404 (4)
C1'	1.0392 (2)	0.50531 (17)	0.75630 (15)	0.0372 (4)
C8	0.1692 (2)	0.91266 (18)	0.33808 (16)	0.0395 (4)
C5	0.3002 (2)	0.76950 (19)	0.64032 (17)	0.0423 (4)
C3'	1.2086 (2)	0.39608 (19)	0.68643 (17)	0.0420 (4)
C3	0.4572 (2)	0.77942 (18)	0.85787 (16)	0.0391 (4)
C4'	1.2720 (2)	0.40079 (19)	0.80701 (17)	0.0418 (4)
C7	0.2705 (2)	0.88207 (19)	0.43220 (17)	0.0420 (4)
C1	0.5419 (2)	0.71451 (18)	0.70306 (17)	0.0403 (4)
C7'	0.9147 (2)	0.55954 (19)	0.72677 (17)	0.0422 (4)
C6'	1.1052 (2)	0.5099 (2)	0.87698 (17)	0.0434 (4)
C2	0.5799 (2)	0.7421 (2)	0.89668 (18)	0.0460 (4)
C6	0.3670 (3)	0.9180 (2)	0.64893 (18)	0.0482 (4)
C4	0.5590 (3)	0.6836 (3)	0.5775 (2)	0.0540 (5)
C5'	1.2197 (3)	0.4587 (2)	0.90209 (18)	0.0474 (4)
C9	0.1616 (3)	0.8622 (2)	0.21389 (18)	0.0508 (5)
C8'	1.4517 (4)	0.2998 (3)	0.7517 (3)	0.0650 (6)
C13	0.0911 (3)	0.9973 (3)	0.3722 (2)	0.0545 (5)
C11	−0.0037 (3)	0.9767 (3)	0.1587 (2)	0.0651 (6)
C10	0.0749 (3)	0.8943 (3)	0.1246 (2)	0.0639 (6)
C12	0.0049 (3)	1.0293 (3)	0.2823 (3)	0.0670 (6)
H5A	0.269 (3)	0.702 (2)	0.552 (2)	0.046 (5)*
H5B	0.194 (3)	0.744 (2)	0.6573 (19)	0.041 (5)*
H6A	0.480 (3)	0.942 (2)	0.640 (2)	0.055 (6)*
H6B	0.373 (3)	0.985 (2)	0.734 (2)	0.054 (6)*
H6'	1.069 (3)	0.549 (2)	0.941 (2)	0.062 (6)*
H2'	1.055 (3)	0.446 (2)	0.578 (2)	0.051 (6)*
H4A	0.645 (3)	0.659 (2)	0.577 (2)	0.056 (6)*
H2	0.624 (3)	0.739 (3)	0.977 (3)	0.070 (7)*
H3'	1.243 (3)	0.357 (2)	0.620 (2)	0.062 (7)*
H5'	1.261 (3)	0.460 (3)	0.983 (3)	0.071 (7)*
H8'A	1.509 (4)	0.375 (3)	0.726 (3)	0.081 (8)*
H9	0.219 (3)	0.804 (3)	0.190 (2)	0.069 (7)*
H13	0.095 (3)	1.031 (3)	0.451 (3)	0.066 (7)*
H4B	0.458 (4)	0.606 (3)	0.509 (3)	0.090 (9)*
H1'	0.798 (4)	0.636 (3)	0.811 (3)	0.086 (9)*
H4C	0.579 (4)	0.759 (3)	0.556 (3)	0.084 (9)*
H8'B	1.362 (4)	0.219 (3)	0.681 (3)	0.088 (9)*
H8'C	1.527 (4)	0.271 (3)	0.796 (3)	0.079 (8)*
H10	0.069 (4)	0.855 (3)	0.037 (3)	0.096 (9)*
H12	−0.045 (4)	1.088 (3)	0.313 (3)	0.095 (10)*
H11	−0.073 (4)	0.990 (3)	0.088 (3)	0.082 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0631 (8)	0.0679 (8)	0.0405 (7)	0.0422 (7)	0.0235 (6)	0.0306 (6)
O1'	0.0634 (9)	0.0923 (11)	0.0499 (8)	0.0555 (9)	0.0293 (7)	0.0337 (8)
O3'	0.0698 (9)	0.0814 (10)	0.0511 (8)	0.0548 (8)	0.0214 (7)	0.0307 (7)
O2'	0.0699 (9)	0.0916 (11)	0.0458 (8)	0.0558 (9)	0.0213 (7)	0.0333 (8)
O4	0.0709 (9)	0.0877 (10)	0.0554 (8)	0.0566 (9)	0.0350 (7)	0.0419 (8)
O2	0.0763 (10)	0.0866 (11)	0.0602 (9)	0.0601 (9)	0.0375 (8)	0.0386 (8)
O1	0.0819 (11)	0.0950 (12)	0.0368 (7)	0.0490 (10)	0.0272 (7)	0.0260 (8)
N1	0.0455 (7)	0.0473 (8)	0.0370 (7)	0.0274 (6)	0.0182 (6)	0.0213 (6)
N3	0.0501 (8)	0.0473 (8)	0.0407 (8)	0.0245 (7)	0.0208 (7)	0.0187 (6)
N2	0.0451 (8)	0.0586 (9)	0.0472 (8)	0.0310 (7)	0.0185 (7)	0.0265 (7)
C2'	0.0439 (9)	0.0471 (9)	0.0325 (8)	0.0221 (7)	0.0136 (7)	0.0177 (7)
C1'	0.0361 (8)	0.0417 (8)	0.0364 (8)	0.0177 (6)	0.0144 (6)	0.0178 (7)
C8	0.0384 (8)	0.0490 (9)	0.0381 (8)	0.0209 (7)	0.0165 (7)	0.0235 (7)
C5	0.0425 (9)	0.0461 (9)	0.0400 (9)	0.0214 (7)	0.0145 (7)	0.0187 (7)
C3'	0.0480 (9)	0.0476 (9)	0.0355 (8)	0.0257 (8)	0.0183 (7)	0.0162 (7)
C3	0.0433 (8)	0.0438 (8)	0.0353 (8)	0.0216 (7)	0.0163 (7)	0.0186 (7)
C4'	0.0427 (9)	0.0462 (9)	0.0405 (9)	0.0240 (7)	0.0133 (7)	0.0194 (7)
C7	0.0463 (9)	0.0523 (9)	0.0405 (9)	0.0277 (8)	0.0205 (7)	0.0256 (8)
C1	0.0431 (9)	0.0440 (9)	0.0417 (9)	0.0237 (7)	0.0192 (7)	0.0201 (7)
C7'	0.0397 (8)	0.0483 (9)	0.0399 (9)	0.0215 (7)	0.0150 (7)	0.0174 (7)
C6'	0.0461 (9)	0.0562 (10)	0.0371 (9)	0.0265 (8)	0.0211 (7)	0.0226 (8)
C2	0.0468 (9)	0.0588 (11)	0.0402 (9)	0.0285 (8)	0.0152 (7)	0.0249 (8)
C6	0.0546 (11)	0.0501 (10)	0.0388 (9)	0.0232 (8)	0.0120 (8)	0.0209 (8)
C4	0.0650 (13)	0.0688 (13)	0.0497 (11)	0.0431 (11)	0.0311 (10)	0.0287 (10)
C5'	0.0550 (10)	0.0630 (11)	0.0346 (9)	0.0320 (9)	0.0178 (8)	0.0254 (8)
C9	0.0606 (11)	0.0591 (11)	0.0383 (9)	0.0316 (10)	0.0186 (8)	0.0209 (8)
C8'	0.0742 (15)	0.0746 (15)	0.0626 (14)	0.0540 (14)	0.0248 (12)	0.0250 (12)
C13	0.0622 (12)	0.0804 (14)	0.0480 (11)	0.0464 (11)	0.0302 (9)	0.0363 (10)
C11	0.0629 (13)	0.0952 (17)	0.0603 (13)	0.0452 (13)	0.0218 (11)	0.0504 (13)
C10	0.0773 (15)	0.0840 (15)	0.0384 (10)	0.0415 (13)	0.0187 (10)	0.0308 (10)
C12	0.0744 (15)	0.0998 (18)	0.0706 (15)	0.0638 (14)	0.0384 (12)	0.0524 (14)

Geometric parameters (Å, º) top

O3—C7	1.355 (2)	C3'—C4'	1.391 (2)
O3—C6	1.446 (2)	C3'—H3'	0.96 (3)
O1'—C7'	1.320 (2)	C3—C2	1.355 (2)
O1'—H1'	0.84 (3)	C4'—C5'	1.392 (3)
O3'—C4'	1.359 (2)	C1—C4	1.482 (3)
O3'—C8'	1.421 (3)	C6'—C5'	1.369 (3)
O2'—C7'	1.217 (2)	C6'—H6'	0.94 (3)
O4—C7	1.204 (2)	C2—H2	0.97 (3)
O2—N3	1.225 (2)	C6—H6A	1.01 (2)
O1—N3	1.222 (2)	C6—H6B	1.04 (2)
N1—C5	1.480 (2)	C4—H4A	0.92 (3)
N1—C3	1.381 (2)	C4—H4B	0.97 (3)
N1—C1	1.350 (2)	C4—H4C	0.92 (3)
N3—C3	1.414 (2)	C5'—H5'	0.94 (3)
N2—C1	1.331 (2)	C9—C10	1.382 (3)
N2—C2	1.361 (2)	C9—H9	0.98 (3)
C2'—C1'	1.391 (2)	C8'—H8'A	1.00 (3)
C2'—C3'	1.384 (2)	C8'—H8'B	0.95 (3)
C2'—H2'	0.97 (2)	C8'—H8'C	0.98 (3)
C1'—C7'	1.481 (2)	C13—C12	1.384 (3)
C1'—C6'	1.397 (2)	C13—H13	0.88 (3)
C8—C7	1.478 (2)	C11—C10	1.372 (4)
C8—C9	1.386 (3)	C11—C12	1.379 (4)
C8—C13	1.388 (3)	C11—H11	1.01 (3)
C5—C6	1.513 (3)	C10—H10	0.98 (3)
C5—H5A	1.00 (2)	C12—H12	0.95 (3)
C5—H5B	1.00 (2)

C7—O3—C6	115.93 (14)	C1'—C6'—H6'	118.4 (15)
C7'—O1'—H1'	117 (2)	C5'—C6'—C1'	120.87 (17)
C4'—O3'—C8'	118.47 (17)	C5'—C6'—H6'	120.7 (15)
C3—N1—C5	130.29 (14)	N2—C2—H2	122.3 (16)
C1—N1—C5	123.92 (15)	C3—C2—N2	109.30 (16)
C1—N1—C3	105.61 (14)	C3—C2—H2	128.3 (16)
O2—N3—C3	119.27 (15)	O3—C6—C5	109.66 (15)
O1—N3—O2	123.58 (16)	O3—C6—H6A	109.6 (13)
O1—N3—C3	117.15 (16)	O3—C6—H6B	107.7 (12)
C1—N2—C2	106.00 (15)	C5—C6—H6A	107.2 (12)
C1'—C2'—H2'	121.8 (13)	C5—C6—H6B	109.6 (12)
C3'—C2'—C1'	121.08 (16)	H6A—C6—H6B	113.0 (18)
C3'—C2'—H2'	117.1 (13)	C1—C4—H4A	110.3 (15)
C2'—C1'—C7'	119.62 (15)	C1—C4—H4B	112.5 (18)
C2'—C1'—C6'	118.55 (16)	C1—C4—H4C	111.9 (19)
C6'—C1'—C7'	121.83 (16)	H4A—C4—H4B	107 (2)
C9—C8—C7	118.52 (16)	H4A—C4—H4C	109 (2)
C9—C8—C13	119.36 (17)	H4B—C4—H4C	106 (3)
C13—C8—C7	121.99 (16)	C4'—C5'—H5'	119.7 (16)
N1—C5—C6	108.80 (15)	C6'—C5'—C4'	120.21 (17)
N1—C5—H5A	111.9 (12)	C6'—C5'—H5'	120.1 (16)
N1—C5—H5B	111.0 (11)	C8—C9—H9	119.7 (15)
C6—C5—H5A	109.4 (12)	C10—C9—C8	120.3 (2)
C6—C5—H5B	110.5 (11)	C10—C9—H9	120.1 (15)
H5A—C5—H5B	105.3 (16)	O3'—C8'—H8'A	108.8 (17)
C2'—C3'—C4'	119.46 (16)	O3'—C8'—H8'B	108.8 (19)
C2'—C3'—H3'	119.6 (15)	O3'—C8'—H8'C	104.0 (17)
C4'—C3'—H3'	120.9 (15)	H8'A—C8'—H8'B	111 (3)
N1—C3—N3	124.90 (15)	H8'A—C8'—H8'C	114 (2)
C2—C3—N1	107.41 (15)	H8'B—C8'—H8'C	109 (2)
C2—C3—N3	127.68 (16)	C8—C13—H13	120.7 (17)
O3'—C4'—C3'	124.69 (17)	C12—C13—C8	120.1 (2)
O3'—C4'—C5'	115.47 (16)	C12—C13—H13	119.3 (17)
C3'—C4'—C5'	119.83 (16)	C10—C11—C12	120.4 (2)
O3—C7—C8	112.45 (14)	C10—C11—H11	116.3 (16)
O4—C7—O3	122.94 (16)	C12—C11—H11	123.2 (17)
O4—C7—C8	124.57 (16)	C9—C10—H10	118.5 (19)
N1—C1—C4	123.52 (16)	C11—C10—C9	120.0 (2)
N2—C1—N1	111.65 (15)	C11—C10—H10	121.4 (19)
N2—C1—C4	124.83 (16)	C13—C12—H12	115 (2)
O1'—C7'—C1'	113.17 (15)	C11—C12—C13	119.9 (2)
O2'—C7'—O1'	123.39 (17)	C11—C12—H12	125 (2)
O2'—C7'—C1'	123.44 (16)

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–3,5-dinitrobenzoic acid (1/1) (bzmd35dnz) top

Crystal data top

C₁₃H₁₃N₃O₄·C₇H₄N₂O₆	F(000) = 1008
M_r = 487.39	D_x = 1.533 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.0988 (13) Å	Cell parameters from 9941 reflections
b = 8.4322 (5) Å	θ = 2.6–27.3°
c = 12.0341 (8) Å	µ = 0.13 mm⁻¹
β = 99.505 (2)°	T = 300 K
V = 2111.6 (2) Å³	Plate, clear light colourless
Z = 4	0.46 × 0.40 × 0.06 mm

Data collection top

Bruker APEXII CCD diffractometer	3321 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.108
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 27.5°, θ_min = 2.6°
T_min = 0.587, T_max = 0.746	h = −27→27
71598 measured reflections	k = −10→10
4820 independent reflections	l = −15→15

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.065	w = 1/[σ²(F_o²) + (0.0808P)² + 2.0317P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.213	(Δ/σ)_max < 0.001
S = 1.14	Δρ_max = 0.40 e Å⁻³
4820 reflections	Δρ_min = −0.35 e Å⁻³
385 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.026 (4)
Primary atom site location: dual

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O3	0.88887 (9)	0.4296 (3)	0.67819 (18)	0.0501 (5)
O1'	0.62334 (9)	0.4206 (3)	0.8640 (2)	0.0519 (6)
O6'	0.41665 (11)	0.3221 (3)	0.9795 (2)	0.0617 (7)
O2'	0.62851 (10)	0.6000 (3)	0.7300 (2)	0.0691 (8)
N1	0.84690 (10)	0.3243 (3)	0.8853 (2)	0.0403 (5)
O3'	0.42660 (12)	0.6852 (3)	0.4624 (2)	0.0659 (7)
O5'	0.32969 (10)	0.4181 (4)	0.8826 (2)	0.0672 (7)
O4'	0.33601 (11)	0.6115 (4)	0.5067 (2)	0.0731 (8)
N2	0.74971 (11)	0.4037 (3)	0.9065 (2)	0.0485 (6)
N1'	0.38764 (11)	0.3936 (3)	0.8979 (2)	0.0500 (6)
O2	0.95921 (11)	0.3723 (4)	1.0441 (2)	0.0787 (9)
O4	0.97119 (11)	0.5544 (4)	0.6211 (3)	0.0766 (8)
N3	0.90992 (12)	0.4399 (4)	1.0593 (2)	0.0521 (7)
O1	0.90695 (14)	0.5286 (4)	1.1385 (2)	0.0810 (9)
N2'	0.39462 (13)	0.6237 (3)	0.5270 (2)	0.0533 (7)
C5'	0.52600 (12)	0.5108 (3)	0.7595 (3)	0.0419 (6)
C1'	0.42448 (12)	0.4538 (3)	0.8136 (3)	0.0419 (6)
C4'	0.49473 (13)	0.5679 (3)	0.6577 (3)	0.0437 (7)
C6'	0.49130 (13)	0.4515 (4)	0.8391 (3)	0.0427 (7)
C1	0.78368 (13)	0.3235 (4)	0.8418 (3)	0.0434 (7)
C3'	0.42799 (13)	0.5640 (3)	0.6359 (3)	0.0436 (7)
C3	0.85199 (13)	0.4118 (4)	0.9835 (2)	0.0424 (6)
C7'	0.59800 (13)	0.5155 (4)	0.7827 (3)	0.0461 (7)
C2'	0.39175 (13)	0.5094 (4)	0.7128 (3)	0.0454 (7)
C7	0.91451 (14)	0.5258 (4)	0.6079 (3)	0.0493 (7)
C8	0.86719 (15)	0.5910 (4)	0.5147 (3)	0.0482 (7)
C5	0.89796 (15)	0.2510 (4)	0.8332 (3)	0.0493 (7)
C6	0.93347 (15)	0.3681 (5)	0.7725 (3)	0.0523 (8)
C2	0.79212 (14)	0.4589 (4)	0.9961 (3)	0.0480 (7)
C11	0.7809 (2)	0.7221 (5)	0.3390 (4)	0.0706 (11)
C4	0.75565 (19)	0.2433 (6)	0.7357 (4)	0.0639 (10)
C10	0.75929 (19)	0.6644 (5)	0.4327 (4)	0.0685 (10)
C9	0.80146 (16)	0.5962 (4)	0.5207 (3)	0.0569 (8)
C13	0.8889 (2)	0.6517 (4)	0.4218 (3)	0.0613 (9)
C12	0.8460 (2)	0.7149 (5)	0.3335 (3)	0.0718 (11)
H4'	0.5171 (15)	0.612 (4)	0.593 (3)	0.046 (8)*
H2'	0.3449 (16)	0.512 (4)	0.695 (3)	0.041 (8)*
H5A	0.8774 (17)	0.173 (4)	0.780 (3)	0.057 (10)*
H6'	0.5098 (15)	0.409 (4)	0.912 (3)	0.044 (8)*
H5B	0.9296 (17)	0.201 (4)	0.897 (3)	0.059 (10)*
H2	0.7782 (19)	0.516 (5)	1.051 (3)	0.066 (11)*
H6A	0.9522 (16)	0.454 (4)	0.825 (3)	0.049 (9)*
H9	0.7866 (16)	0.548 (4)	0.590 (3)	0.047 (9)*
H1'	0.671 (2)	0.429 (5)	0.882 (3)	0.073 (12)*
H6B	0.9718 (18)	0.319 (4)	0.747 (3)	0.060 (10)*
H13	0.935 (2)	0.639 (6)	0.419 (4)	0.089 (14)*
H10	0.714 (2)	0.669 (5)	0.439 (4)	0.084 (13)*
H12	0.866 (2)	0.751 (6)	0.265 (5)	0.110 (17)*
H11	0.7488 (19)	0.769 (5)	0.276 (3)	0.067 (11)*
H4A	0.759 (2)	0.131 (7)	0.751 (4)	0.104 (17)*
H4B	0.773 (2)	0.282 (5)	0.668 (4)	0.072 (12)*
H4C	0.711 (3)	0.267 (6)	0.716 (4)	0.099 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0329 (10)	0.0680 (14)	0.0492 (12)	−0.0043 (9)	0.0063 (8)	0.0048 (10)
O1'	0.0273 (9)	0.0594 (13)	0.0677 (14)	0.0030 (9)	0.0035 (9)	0.0137 (11)
O6'	0.0479 (12)	0.0870 (18)	0.0510 (13)	0.0040 (12)	0.0107 (10)	−0.0001 (12)
O2'	0.0353 (11)	0.0812 (17)	0.0884 (19)	−0.0069 (11)	0.0032 (11)	0.0323 (15)
N1	0.0306 (11)	0.0462 (13)	0.0442 (13)	0.0038 (9)	0.0064 (9)	0.0033 (10)
O3'	0.0580 (14)	0.0854 (18)	0.0528 (14)	0.0023 (13)	0.0047 (11)	0.0062 (13)
O5'	0.0304 (11)	0.099 (2)	0.0742 (17)	0.0064 (11)	0.0144 (10)	−0.0028 (14)
O4'	0.0410 (12)	0.095 (2)	0.0752 (18)	−0.0037 (12)	−0.0136 (12)	0.0065 (15)
N2	0.0296 (11)	0.0577 (15)	0.0581 (16)	0.0034 (10)	0.0075 (11)	0.0069 (12)
N1'	0.0341 (12)	0.0632 (16)	0.0539 (16)	0.0018 (11)	0.0107 (11)	−0.0132 (13)
O2	0.0378 (12)	0.124 (2)	0.0699 (17)	0.0138 (14)	−0.0042 (11)	−0.0054 (16)
O4	0.0367 (12)	0.104 (2)	0.089 (2)	−0.0152 (13)	0.0115 (12)	0.0193 (16)
N3	0.0404 (13)	0.0696 (18)	0.0443 (15)	−0.0002 (12)	0.0013 (11)	0.0053 (13)
O1	0.0725 (18)	0.109 (2)	0.0557 (16)	0.0028 (16)	−0.0065 (13)	−0.0216 (16)
N2'	0.0437 (14)	0.0577 (16)	0.0536 (16)	0.0041 (12)	−0.0061 (12)	−0.0073 (13)
C5'	0.0296 (12)	0.0395 (14)	0.0551 (17)	0.0026 (10)	0.0029 (11)	−0.0038 (13)
C1'	0.0292 (12)	0.0481 (15)	0.0481 (16)	0.0014 (11)	0.0054 (11)	−0.0098 (12)
C4'	0.0327 (13)	0.0443 (15)	0.0529 (17)	0.0021 (11)	0.0033 (12)	−0.0045 (13)
C6'	0.0321 (13)	0.0448 (15)	0.0498 (17)	0.0014 (11)	0.0024 (12)	−0.0065 (13)
C1	0.0313 (13)	0.0468 (15)	0.0514 (16)	−0.0034 (11)	0.0048 (11)	0.0044 (13)
C3'	0.0355 (14)	0.0448 (15)	0.0480 (16)	0.0046 (11)	0.0001 (12)	−0.0053 (12)
C3	0.0347 (13)	0.0499 (16)	0.0420 (15)	0.0029 (11)	0.0042 (11)	0.0082 (12)
C7'	0.0333 (13)	0.0466 (16)	0.0569 (18)	−0.0009 (12)	0.0029 (12)	0.0028 (14)
C2'	0.0305 (13)	0.0500 (16)	0.0542 (17)	0.0036 (11)	0.0027 (12)	−0.0101 (14)
C7	0.0379 (14)	0.0588 (18)	0.0526 (18)	−0.0064 (13)	0.0118 (13)	−0.0055 (14)
C8	0.0451 (15)	0.0503 (17)	0.0493 (17)	−0.0048 (13)	0.0079 (13)	−0.0066 (13)
C5	0.0384 (15)	0.0557 (18)	0.0552 (18)	0.0062 (13)	0.0119 (13)	0.0000 (15)
C6	0.0348 (14)	0.072 (2)	0.0505 (18)	0.0036 (14)	0.0081 (13)	0.0011 (16)
C2	0.0408 (15)	0.0587 (18)	0.0456 (17)	0.0085 (13)	0.0100 (13)	0.0043 (14)
C11	0.081 (3)	0.055 (2)	0.067 (2)	0.0016 (19)	−0.013 (2)	−0.0025 (18)
C4	0.050 (2)	0.077 (3)	0.061 (2)	−0.0153 (18)	0.0006 (16)	−0.0085 (19)
C10	0.052 (2)	0.063 (2)	0.085 (3)	−0.0061 (17)	−0.0068 (19)	−0.006 (2)
C9	0.0441 (17)	0.0586 (19)	0.066 (2)	−0.0098 (14)	0.0048 (15)	−0.0023 (17)
C13	0.065 (2)	0.059 (2)	0.063 (2)	0.0035 (17)	0.0208 (18)	0.0003 (17)
C12	0.103 (3)	0.058 (2)	0.055 (2)	0.007 (2)	0.016 (2)	0.0025 (17)

Geometric parameters (Å, º) top

O3—C7	1.347 (4)	C6'—H6'	0.97 (3)
O3—C6	1.446 (4)	C1—C4	1.478 (5)
O1'—C7'	1.308 (4)	C3'—C2'	1.374 (4)
O1'—H1'	0.99 (4)	C3—C2	1.356 (4)
O6'—N1'	1.227 (4)	C2'—H2'	0.98 (3)
O2'—C7'	1.208 (4)	C7—C8	1.479 (5)
N1—C1	1.350 (3)	C8—C9	1.401 (4)
N1—C3	1.382 (4)	C8—C13	1.375 (5)
N1—C5	1.469 (4)	C5—C6	1.501 (5)
O3'—N2'	1.225 (4)	C5—H5A	0.97 (4)
O5'—N1'	1.223 (3)	C5—H5B	1.02 (4)
O4'—N2'	1.225 (3)	C6—H6A	1.00 (4)
N2—C1	1.328 (4)	C6—H6B	1.00 (4)
N2—C2	1.364 (4)	C2—H2	0.91 (4)
N1'—C1'	1.467 (4)	C11—C10	1.373 (6)
O2—N3	1.226 (4)	C11—C12	1.387 (6)
O4—C7	1.204 (4)	C11—H11	1.01 (4)
N3—O1	1.221 (4)	C4—H4A	0.97 (6)
N3—C3	1.419 (4)	C4—H4B	1.01 (4)
N2'—C3'	1.469 (4)	C4—H4C	0.95 (5)
C5'—C4'	1.379 (4)	C10—C9	1.390 (5)
C5'—C6'	1.391 (4)	C10—H10	0.97 (5)
C5'—C7'	1.499 (4)	C9—H9	1.02 (3)
C1'—C6'	1.393 (4)	C13—C12	1.384 (6)
C1'—C2'	1.375 (4)	C13—H13	0.98 (4)
C4'—C3'	1.390 (4)	C12—H12	1.04 (5)
C4'—H4'	1.05 (3)

C7—O3—C6	115.6 (2)	O3—C7—C8	114.1 (2)
C7'—O1'—H1'	113 (2)	O4—C7—O3	122.1 (3)
C1—N1—C3	105.5 (2)	O4—C7—C8	123.8 (3)
C1—N1—C5	125.4 (3)	C9—C8—C7	121.5 (3)
C3—N1—C5	129.1 (2)	C13—C8—C7	118.8 (3)
C1—N2—C2	106.9 (2)	C13—C8—C9	119.7 (3)
O6'—N1'—C1'	118.2 (2)	N1—C5—C6	113.0 (3)
O5'—N1'—O6'	123.9 (3)	N1—C5—H5A	107 (2)
O5'—N1'—C1'	117.9 (3)	N1—C5—H5B	107 (2)
O2—N3—C3	119.2 (3)	C6—C5—H5A	109 (2)
O1—N3—O2	123.7 (3)	C6—C5—H5B	108 (2)
O1—N3—C3	117.0 (3)	H5A—C5—H5B	113 (3)
O3'—N2'—C3'	118.5 (3)	O3—C6—C5	107.8 (3)
O4'—N2'—O3'	123.6 (3)	O3—C6—H6A	112.3 (19)
O4'—N2'—C3'	117.9 (3)	O3—C6—H6B	111 (2)
C4'—C5'—C6'	120.5 (3)	C5—C6—H6A	110.1 (19)
C4'—C5'—C7'	118.5 (3)	C5—C6—H6B	112 (2)
C6'—C5'—C7'	120.9 (3)	H6A—C6—H6B	104 (3)
C6'—C1'—N1'	118.4 (3)	N2—C2—H2	121 (2)
C2'—C1'—N1'	118.8 (2)	C3—C2—N2	108.2 (3)
C2'—C1'—C6'	122.8 (3)	C3—C2—H2	131 (3)
C5'—C4'—C3'	118.8 (3)	C10—C11—C12	119.3 (4)
C5'—C4'—H4'	125.4 (18)	C10—C11—H11	119 (2)
C3'—C4'—H4'	115.8 (18)	C12—C11—H11	122 (2)
C5'—C6'—C1'	118.2 (3)	C1—C4—H4A	106 (3)
C5'—C6'—H6'	125.2 (18)	C1—C4—H4B	114 (2)
C1'—C6'—H6'	116.6 (19)	C1—C4—H4C	111 (3)
N1—C1—C4	124.5 (3)	H4A—C4—H4B	116 (4)
N2—C1—N1	111.3 (3)	H4A—C4—H4C	107 (4)
N2—C1—C4	124.2 (3)	H4B—C4—H4C	102 (4)
C4'—C3'—N2'	118.8 (3)	C11—C10—C9	121.0 (4)
C2'—C3'—N2'	118.5 (3)	C11—C10—H10	121 (3)
C2'—C3'—C4'	122.7 (3)	C9—C10—H10	118 (3)
N1—C3—N3	125.1 (3)	C8—C9—H9	117.9 (19)
C2—C3—N1	108.0 (3)	C10—C9—C8	119.2 (4)
C2—C3—N3	126.7 (3)	C10—C9—H9	122.9 (19)
O1'—C7'—C5'	113.6 (3)	C8—C13—C12	120.3 (4)
O2'—C7'—O1'	124.5 (3)	C8—C13—H13	117 (3)
O2'—C7'—C5'	122.0 (3)	C12—C13—H13	123 (3)
C1'—C2'—H2'	122.6 (18)	C11—C12—H12	124 (3)
C3'—C2'—C1'	117.0 (3)	C13—C12—C11	120.5 (4)
C3'—C2'—H2'	120.4 (18)	C13—C12—H12	115 (3)

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–3-aminobenzoic acid (1/1) (bzmdabn) top

Crystal data top

C₁₃H₁₃N₃O₄·C₇H₇NO₂	Z = 2
M_r = 412.40	F(000) = 432
Triclinic, P1	D_x = 1.254 Mg m⁻³
a = 7.9316 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.9585 (12) Å	Cell parameters from 6174 reflections
c = 12.1978 (12) Å	θ = 2.7–29.7°
α = 76.362 (3)°	µ = 0.09 mm⁻¹
β = 78.927 (3)°	T = 300 K
γ = 79.583 (3)°	Plate, clear light colourless
V = 1092.21 (18) Å³	0.91 × 0.09 × 0.05 mm

Data collection top

Bruker APEXII CCD diffractometer	2711 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.090
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 27.5°, θ_min = 2.6°
T_min = 0.587, T_max = 0.746	h = −10→10
38219 measured reflections	k = −15→15
5008 independent reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.168	w = 1/[σ²(F_o²) + (0.0722P)² + 0.2049P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
5008 reflections	Δρ_max = 0.25 e Å⁻³
340 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.4965 (2)	−0.14226 (17)	0.07569 (17)	0.0875 (6)
O2	0.2393 (2)	−0.07338 (15)	0.03516 (16)	0.0810 (5)
O3	0.13769 (18)	0.29191 (12)	0.00673 (13)	0.0578 (4)
O4	0.1642 (3)	0.33490 (16)	−0.18307 (15)	0.0845 (6)
N1	0.2025 (2)	0.08578 (15)	0.17918 (14)	0.0541 (4)
N2	0.3948 (3)	0.0924 (2)	0.28556 (17)	0.0710 (6)
N3	0.3595 (3)	−0.07569 (17)	0.08576 (17)	0.0646 (5)
C1	0.3443 (3)	0.00215 (19)	0.15970 (18)	0.0558 (5)
C2	0.4600 (3)	0.0087 (3)	0.2261 (2)	0.0691 (7)
H2	0.569 (4)	−0.039 (2)	0.230 (2)	0.083 (8)*
C3	0.2405 (3)	0.1382 (2)	0.25590 (18)	0.0612 (6)
C4	0.1251 (4)	0.2346 (3)	0.3018 (2)	0.0881 (8)
H4A	0.103783	0.299389	0.240158	0.132*
H4B	0.179996	0.257855	0.354842	0.132*
H4C	0.017095	0.208828	0.340157	0.132*
C5	0.0448 (3)	0.1185 (2)	0.1250 (2)	0.0619 (6)
H5A	−0.003 (3)	0.051 (2)	0.1289 (18)	0.063 (6)*
H5B	−0.040 (3)	0.1650 (19)	0.1716 (19)	0.062 (6)*
C6	0.0791 (3)	0.1848 (2)	0.0046 (2)	0.0604 (6)
H6A	0.170 (3)	0.141 (2)	−0.0427 (19)	0.065 (7)*
H6B	−0.029 (3)	0.204 (2)	−0.027 (2)	0.070 (7)*
C7	0.1776 (3)	0.3604 (2)	−0.0960 (2)	0.0584 (5)
C8	0.2397 (3)	0.46813 (19)	−0.0895 (2)	0.0578 (5)
C9	0.2958 (4)	0.5415 (2)	−0.1918 (3)	0.0776 (7)
H9	0.294 (3)	0.518 (2)	−0.264 (2)	0.080 (8)*
C10	0.3595 (4)	0.6420 (3)	−0.1898 (4)	0.0939 (10)
H10	0.397 (5)	0.693 (3)	−0.261 (3)	0.130 (12)*
C11	0.3661 (4)	0.6693 (3)	−0.0888 (4)	0.0907 (9)
H11	0.415 (4)	0.744 (3)	−0.091 (2)	0.104 (9)*
C12	0.3096 (3)	0.5983 (3)	0.0117 (3)	0.0803 (8)
H12	0.316 (4)	0.613 (2)	0.085 (3)	0.098 (9)*
C13	0.2470 (3)	0.4974 (2)	0.0121 (2)	0.0657 (6)
H13	0.210 (3)	0.448 (2)	0.081 (2)	0.075 (8)*
O1'	0.4959 (2)	0.15720 (18)	0.45717 (16)	0.0845 (6)
H1'	0.474 (4)	0.122 (3)	0.396 (3)	0.122 (11)*
O2'	0.7592 (3)	0.06517 (18)	0.41258 (17)	0.0914 (6)
N1'	1.0963 (3)	0.1476 (3)	0.6945 (2)	0.0842 (7)
H1'A	1.138 (4)	0.198 (3)	0.722 (3)	0.110 (11)*
H1'B	1.168 (4)	0.102 (3)	0.652 (3)	0.095 (10)*
C7'	0.6603 (3)	0.1271 (2)	0.4682 (2)	0.0643 (6)
C1'	0.7135 (3)	0.1792 (2)	0.55349 (18)	0.0617 (6)
C2'	0.6028 (4)	0.2643 (3)	0.6018 (2)	0.0823 (8)
H2'	0.478 (4)	0.298 (2)	0.574 (2)	0.103 (9)*
C3'	0.6603 (4)	0.3099 (3)	0.6800 (3)	0.0954 (10)
H3'	0.580 (4)	0.379 (3)	0.712 (3)	0.127 (11)*
C4'	0.8236 (4)	0.2728 (3)	0.7085 (3)	0.0847 (8)
H4'	0.872 (3)	0.309 (2)	0.762 (2)	0.093 (8)*
C5'	0.9352 (3)	0.1877 (2)	0.66121 (19)	0.0648 (6)
C6'	0.8774 (3)	0.1406 (2)	0.58364 (18)	0.0582 (5)
H6'	0.955 (3)	0.073 (2)	0.5552 (19)	0.068 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0721 (11)	0.0846 (13)	0.0996 (14)	0.0064 (10)	−0.0086 (10)	−0.0243 (11)
O2	0.0819 (12)	0.0795 (12)	0.0981 (13)	−0.0162 (9)	−0.0341 (10)	−0.0308 (10)
O3	0.0616 (9)	0.0565 (9)	0.0611 (9)	−0.0122 (7)	−0.0197 (7)	−0.0130 (7)
O4	0.1176 (15)	0.0857 (13)	0.0643 (11)	−0.0287 (11)	−0.0359 (10)	−0.0148 (9)
N1	0.0496 (10)	0.0614 (11)	0.0536 (10)	−0.0155 (8)	−0.0120 (8)	−0.0075 (8)
N2	0.0744 (13)	0.0885 (15)	0.0583 (12)	−0.0274 (11)	−0.0234 (10)	−0.0090 (11)
N3	0.0614 (12)	0.0627 (12)	0.0695 (12)	−0.0124 (10)	−0.0100 (10)	−0.0106 (10)
C1	0.0496 (12)	0.0627 (13)	0.0567 (12)	−0.0138 (10)	−0.0131 (9)	−0.0073 (10)
C2	0.0572 (14)	0.0846 (18)	0.0661 (15)	−0.0151 (13)	−0.0201 (12)	−0.0047 (13)
C3	0.0686 (14)	0.0683 (15)	0.0503 (12)	−0.0228 (12)	−0.0090 (11)	−0.0098 (11)
C4	0.105 (2)	0.093 (2)	0.0704 (17)	−0.0207 (17)	−0.0032 (15)	−0.0293 (15)
C5	0.0464 (12)	0.0662 (15)	0.0762 (16)	−0.0133 (11)	−0.0165 (11)	−0.0113 (13)
C6	0.0582 (13)	0.0589 (14)	0.0733 (15)	−0.0104 (11)	−0.0284 (12)	−0.0154 (12)
C7	0.0557 (12)	0.0619 (14)	0.0627 (14)	−0.0050 (10)	−0.0226 (10)	−0.0149 (11)
C8	0.0489 (11)	0.0547 (13)	0.0701 (15)	−0.0012 (9)	−0.0143 (10)	−0.0142 (11)
C9	0.0828 (18)	0.0676 (17)	0.0798 (18)	−0.0069 (13)	−0.0178 (14)	−0.0089 (14)
C10	0.092 (2)	0.0645 (18)	0.115 (3)	−0.0164 (15)	−0.0123 (19)	0.0019 (19)
C11	0.0734 (18)	0.0643 (18)	0.137 (3)	−0.0069 (14)	−0.0119 (18)	−0.032 (2)
C12	0.0664 (16)	0.0819 (19)	0.106 (2)	−0.0073 (14)	−0.0108 (15)	−0.0497 (18)
C13	0.0560 (13)	0.0693 (16)	0.0783 (17)	−0.0086 (11)	−0.0107 (12)	−0.0282 (14)
O1'	0.0754 (12)	0.1161 (15)	0.0759 (12)	−0.0193 (10)	−0.0249 (9)	−0.0324 (11)
O2'	0.0919 (13)	0.1102 (15)	0.0926 (13)	−0.0068 (11)	−0.0299 (11)	−0.0545 (12)
N1'	0.0798 (16)	0.0992 (18)	0.0921 (17)	−0.0008 (14)	−0.0358 (13)	−0.0468 (15)
C7'	0.0691 (15)	0.0757 (16)	0.0531 (13)	−0.0201 (12)	−0.0146 (11)	−0.0113 (12)
C1'	0.0692 (14)	0.0726 (15)	0.0482 (12)	−0.0178 (12)	−0.0107 (10)	−0.0153 (11)
C2'	0.0738 (17)	0.097 (2)	0.0850 (18)	0.0000 (15)	−0.0232 (14)	−0.0374 (16)
C3'	0.087 (2)	0.115 (2)	0.100 (2)	0.0085 (18)	−0.0258 (17)	−0.061 (2)
C4'	0.0858 (19)	0.100 (2)	0.0841 (19)	−0.0021 (16)	−0.0251 (15)	−0.0491 (17)
C5'	0.0704 (15)	0.0771 (16)	0.0535 (12)	−0.0120 (12)	−0.0150 (11)	−0.0209 (11)
C6'	0.0675 (14)	0.0623 (14)	0.0478 (12)	−0.0125 (11)	−0.0107 (10)	−0.0132 (10)

Geometric parameters (Å, º) top

O1—N3	1.229 (3)	C9—C10	1.393 (4)
O2—N3	1.224 (2)	C10—H10	0.96 (4)
O3—C6	1.446 (3)	C10—C11	1.360 (5)
O3—C7	1.341 (3)	C11—H11	1.02 (3)
O4—C7	1.201 (3)	C11—C12	1.364 (5)
N1—C1	1.387 (3)	C12—H12	0.96 (3)
N1—C3	1.346 (3)	C12—C13	1.385 (4)
N1—C5	1.474 (3)	C13—H13	0.94 (3)
N2—C2	1.344 (3)	O1'—H1'	1.00 (4)
N2—C3	1.328 (3)	O1'—C7'	1.312 (3)
N3—C1	1.417 (3)	O2'—C7'	1.202 (3)
C1—C2	1.358 (3)	N1'—H1'A	0.90 (3)
C2—H2	0.95 (3)	N1'—H1'B	0.89 (3)
C3—C4	1.485 (4)	N1'—C5'	1.383 (3)
C4—H4A	0.9600	C7'—C1'	1.490 (3)
C4—H4B	0.9600	C1'—C2'	1.384 (4)
C4—H4C	0.9600	C1'—C6'	1.388 (3)
C5—H5A	0.95 (2)	C2'—H2'	1.08 (3)
C5—H5B	0.98 (2)	C2'—C3'	1.384 (4)
C5—C6	1.495 (3)	C3'—H3'	1.05 (3)
C6—H6A	0.99 (2)	C3'—C4'	1.374 (4)
C6—H6B	0.97 (2)	C4'—H4'	1.02 (3)
C7—C8	1.484 (3)	C4'—C5'	1.381 (4)
C8—C9	1.391 (4)	C5'—C6'	1.391 (3)
C8—C13	1.379 (3)	C6'—H6'	1.01 (2)
C9—H9	0.98 (3)

C7—O3—C6	115.09 (17)	C8—C9—H9	118.2 (15)
C1—N1—C5	129.03 (19)	C8—C9—C10	119.7 (3)
C3—N1—C1	105.68 (18)	C10—C9—H9	122.1 (15)
C3—N1—C5	125.2 (2)	C9—C10—H10	119 (2)
C3—N2—C2	106.95 (19)	C11—C10—C9	120.5 (3)
O1—N3—C1	116.9 (2)	C11—C10—H10	121 (2)
O2—N3—O1	123.5 (2)	C10—C11—H11	117.9 (17)
O2—N3—C1	119.6 (2)	C10—C11—C12	120.1 (3)
N1—C1—N3	125.25 (18)	C12—C11—H11	122.0 (17)
C2—C1—N1	106.9 (2)	C11—C12—H12	122.7 (18)
C2—C1—N3	127.8 (2)	C11—C12—C13	120.6 (3)
N2—C2—C1	109.2 (2)	C13—C12—H12	116.7 (18)
N2—C2—H2	125.6 (16)	C8—C13—C12	120.2 (3)
C1—C2—H2	125.2 (16)	C8—C13—H13	119.1 (15)
N1—C3—C4	124.6 (2)	C12—C13—H13	120.7 (16)
N2—C3—N1	111.2 (2)	C7'—O1'—H1'	108.1 (19)
N2—C3—C4	124.2 (2)	H1'A—N1'—H1'B	120 (3)
C3—C4—H4A	109.5	C5'—N1'—H1'A	114 (2)
C3—C4—H4B	109.5	C5'—N1'—H1'B	115.7 (19)
C3—C4—H4C	109.5	O1'—C7'—C1'	113.7 (2)
H4A—C4—H4B	109.5	O2'—C7'—O1'	122.9 (2)
H4A—C4—H4C	109.5	O2'—C7'—C1'	123.3 (2)
H4B—C4—H4C	109.5	C2'—C1'—C7'	121.1 (2)
N1—C5—H5A	108.9 (13)	C2'—C1'—C6'	120.4 (2)
N1—C5—H5B	107.3 (13)	C6'—C1'—C7'	118.5 (2)
N1—C5—C6	112.39 (18)	C1'—C2'—H2'	120.0 (16)
H5A—C5—H5B	106.2 (19)	C1'—C2'—C3'	118.3 (3)
C6—C5—H5A	111.2 (13)	C3'—C2'—H2'	121.6 (16)
C6—C5—H5B	110.6 (13)	C2'—C3'—H3'	117.9 (19)
O3—C6—C5	107.92 (19)	C4'—C3'—C2'	121.2 (3)
O3—C6—H6A	108.7 (13)	C4'—C3'—H3'	120.7 (19)
O3—C6—H6B	108.6 (14)	C3'—C4'—H4'	122.7 (15)
C5—C6—H6A	111.5 (13)	C3'—C4'—C5'	121.1 (3)
C5—C6—H6B	108.9 (13)	C5'—C4'—H4'	116.1 (15)
H6A—C6—H6B	111.2 (19)	N1'—C5'—C6'	121.5 (2)
O3—C7—C8	113.10 (19)	C4'—C5'—N1'	120.5 (2)
O4—C7—O3	122.3 (2)	C4'—C5'—C6'	118.0 (2)
O4—C7—C8	124.6 (2)	C1'—C6'—C5'	121.0 (2)
C9—C8—C7	117.7 (2)	C1'—C6'—H6'	121.5 (13)
C13—C8—C7	123.3 (2)	C5'—C6'—H6'	117.4 (13)
C13—C8—C9	119.0 (2)

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–salicylic acid (1/1) (bzmdslc) top

Crystal data top

C₁₃H₁₃N₃O₄·C₇H₆O₃	F(000) = 864
M_r = 413.38	D_x = 1.382 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.5055 (6) Å	Cell parameters from 9833 reflections
b = 31.2239 (19) Å	θ = 2.6–27.4°
c = 6.8578 (4) Å	µ = 0.11 mm⁻¹
β = 102.628 (2)°	T = 301 K
V = 1986.2 (2) Å³	Prismatic, colourless
Z = 4	0.68 × 0.24 × 0.16 mm

Data collection top

Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer	3883 reflections with I > 2σ(I)
Multilayer mirrors monochromator	R_int = 0.035
φ and ω scans	θ_max = 27.5°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −12→12
T_min = 0.706, T_max = 0.746	k = −40→40
69959 measured reflections	l = −8→8
4553 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	All H-atom parameters refined
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0521P)² + 0.3493P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
4553 reflections	Δρ_max = 0.17 e Å⁻³
347 parameters	Δρ_min = −0.20 e Å⁻³
100 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.87803 (16)	0.63094 (4)	0.3909 (2)	0.0887 (4)
O2	0.92555 (13)	0.66308 (4)	0.67677 (19)	0.0803 (3)
O3	0.56700 (10)	0.71973 (3)	0.84768 (15)	0.0583 (2)
O4	0.64060 (13)	0.78754 (3)	0.84757 (19)	0.0771 (3)
N1	0.66295 (11)	0.63293 (3)	0.75126 (15)	0.0468 (2)
N2	0.52072 (13)	0.58617 (4)	0.56128 (18)	0.0598 (3)
N3	0.84921 (13)	0.64050 (4)	0.55066 (19)	0.0603 (3)
C1	0.54094 (14)	0.60942 (4)	0.7272 (2)	0.0536 (3)
C2	0.63221 (16)	0.59466 (4)	0.4743 (2)	0.0564 (3)
H2	0.6423 (17)	0.5809 (6)	0.355 (3)	0.073 (5)*
C3	0.71994 (14)	0.62349 (4)	0.58763 (18)	0.0480 (3)
C4	0.4412 (2)	0.60928 (8)	0.8662 (4)	0.0823 (5)
H4A	0.478 (3)	0.5934 (11)	0.988 (5)	0.159 (11)*
H4B	0.427 (3)	0.6365 (9)	0.916 (4)	0.135 (10)*
H4C	0.360 (4)	0.5953 (10)	0.805 (5)	0.156 (11)*
C5	0.72381 (16)	0.65981 (5)	0.92458 (19)	0.0558 (3)
H5A	0.8236 (17)	0.6512 (5)	0.969 (2)	0.058 (4)*
H5B	0.6706 (17)	0.6528 (5)	1.028 (2)	0.064 (4)*
C6	0.71571 (16)	0.70700 (5)	0.8807 (2)	0.0588 (3)
H6A	0.7540 (17)	0.7136 (5)	0.761 (3)	0.068 (4)*
C7	0.54390 (15)	0.76221 (4)	0.83503 (18)	0.0529 (3)
O1'	0.30972 (14)	0.53009 (4)	0.43561 (19)	0.0822 (4)
H1'	0.387 (2)	0.5478 (7)	0.473 (3)	0.102 (7)*
O2'	0.39947 (13)	0.51848 (4)	0.16738 (19)	0.0785 (3)
O3'	0.26597 (14)	0.46438 (4)	−0.10302 (19)	0.0787 (3)
H3'	0.333 (3)	0.4843 (7)	−0.043 (3)	0.105 (7)*
C7'	0.30950 (15)	0.51100 (4)	0.2653 (2)	0.0590 (3)
C1'	0.18997 (14)	0.48065 (4)	0.2017 (2)	0.0519 (3)
C2'	0.17227 (15)	0.45986 (4)	0.0179 (2)	0.0565 (3)
C3'	0.05451 (17)	0.43294 (5)	−0.0447 (3)	0.0659 (4)
H3'A	0.0427 (19)	0.4198 (6)	−0.172 (3)	0.080 (5)*
C4'	−0.04243 (17)	0.42646 (5)	0.0733 (3)	0.0686 (4)
H4'	−0.127 (2)	0.4075 (6)	0.022 (3)	0.085 (5)*
C5'	−0.02454 (16)	0.44612 (5)	0.2583 (3)	0.0668 (4)
H5'	−0.091 (2)	0.4411 (6)	0.340 (3)	0.088 (6)*
C6'	0.09104 (15)	0.47294 (5)	0.3210 (2)	0.0597 (3)
H6'	0.1065 (17)	0.4880 (5)	0.456 (3)	0.073 (5)*
C9	0.28162 (16)	0.74263 (5)	0.7797 (2)	0.0616 (3)
C10	0.1392 (2)	0.75472 (7)	0.7613 (3)	0.0787 (5)
C11	0.1046 (2)	0.79697 (7)	0.7762 (3)	0.0899 (6)
C12	0.2100 (3)	0.82743 (7)	0.8071 (3)	0.0932 (6)
C13	0.3531 (2)	0.81613 (5)	0.8229 (2)	0.0733 (4)
C8	0.38974 (16)	0.77321 (4)	0.81035 (17)	0.0544 (3)
H6B	0.7712 (18)	0.7223 (5)	0.994 (3)	0.069 (4)*
H13	0.4267 (19)	0.8361 (6)	0.839 (3)	0.072 (5)*
H9	0.3077 (18)	0.7123 (5)	0.771 (2)	0.070 (5)*
H12	0.190 (3)	0.8559 (8)	0.811 (4)	0.123 (8)*
H10	0.062 (3)	0.7333 (8)	0.741 (3)	0.112 (7)*
H11	0.000 (3)	0.8054 (7)	0.766 (3)	0.116 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1115 (10)	0.0842 (8)	0.0896 (8)	−0.0158 (7)	0.0642 (8)	−0.0120 (6)
O2	0.0697 (7)	0.0785 (7)	0.0976 (8)	−0.0226 (6)	0.0291 (6)	−0.0181 (6)
O3	0.0585 (5)	0.0463 (5)	0.0674 (6)	−0.0003 (4)	0.0077 (4)	−0.0079 (4)
O4	0.0822 (7)	0.0528 (6)	0.0979 (8)	−0.0125 (5)	0.0230 (6)	−0.0080 (5)
N1	0.0541 (6)	0.0414 (5)	0.0460 (5)	0.0006 (4)	0.0134 (4)	0.0012 (4)
N2	0.0613 (7)	0.0471 (6)	0.0695 (7)	−0.0066 (5)	0.0107 (5)	−0.0016 (5)
N3	0.0680 (7)	0.0500 (6)	0.0698 (7)	−0.0058 (5)	0.0300 (6)	−0.0020 (5)
C1	0.0541 (7)	0.0466 (6)	0.0614 (7)	−0.0008 (5)	0.0157 (6)	0.0071 (5)
C2	0.0697 (8)	0.0442 (6)	0.0557 (7)	−0.0018 (6)	0.0148 (6)	−0.0039 (5)
C3	0.0566 (7)	0.0405 (6)	0.0496 (6)	0.0001 (5)	0.0174 (5)	0.0016 (5)
C4	0.0773 (12)	0.0870 (13)	0.0938 (13)	−0.0075 (10)	0.0428 (10)	0.0071 (11)
C5	0.0621 (8)	0.0579 (8)	0.0451 (6)	0.0046 (6)	0.0070 (6)	−0.0045 (5)
C6	0.0568 (7)	0.0531 (7)	0.0638 (8)	−0.0014 (6)	0.0072 (6)	−0.0134 (6)
C7	0.0714 (8)	0.0457 (6)	0.0413 (6)	−0.0026 (6)	0.0116 (5)	−0.0068 (5)
O1'	0.0769 (7)	0.0870 (8)	0.0883 (8)	−0.0321 (6)	0.0302 (6)	−0.0276 (6)
O2'	0.0726 (7)	0.0773 (7)	0.0948 (8)	−0.0190 (6)	0.0387 (6)	−0.0027 (6)
O3'	0.0817 (8)	0.0850 (8)	0.0804 (7)	−0.0055 (6)	0.0414 (6)	−0.0145 (6)
C7'	0.0577 (7)	0.0500 (7)	0.0723 (9)	−0.0018 (6)	0.0211 (6)	0.0011 (6)
C1'	0.0501 (6)	0.0414 (6)	0.0664 (8)	0.0038 (5)	0.0177 (6)	0.0003 (5)
C2'	0.0573 (7)	0.0489 (7)	0.0672 (8)	0.0090 (5)	0.0224 (6)	−0.0005 (6)
C3'	0.0641 (8)	0.0579 (8)	0.0750 (10)	0.0052 (6)	0.0136 (7)	−0.0139 (7)
C4'	0.0542 (8)	0.0570 (8)	0.0942 (11)	−0.0026 (6)	0.0150 (7)	−0.0108 (8)
C5'	0.0552 (8)	0.0628 (9)	0.0882 (11)	−0.0045 (6)	0.0284 (7)	−0.0056 (7)
C6'	0.0575 (7)	0.0537 (7)	0.0728 (9)	−0.0007 (6)	0.0250 (6)	−0.0065 (6)
C9	0.0675 (8)	0.0617 (8)	0.0529 (7)	0.0029 (7)	0.0076 (6)	−0.0094 (6)
C10	0.0697 (10)	0.0947 (13)	0.0667 (9)	0.0059 (9)	0.0041 (8)	−0.0144 (8)
C11	0.0814 (12)	0.1051 (15)	0.0744 (11)	0.0296 (11)	−0.0021 (9)	−0.0137 (10)
C12	0.1147 (16)	0.0723 (11)	0.0852 (12)	0.0411 (11)	0.0056 (11)	−0.0024 (9)
C13	0.0964 (12)	0.0533 (8)	0.0661 (9)	0.0106 (8)	0.0089 (8)	−0.0010 (7)
C8	0.0739 (8)	0.0508 (7)	0.0363 (6)	0.0074 (6)	0.0077 (5)	−0.0034 (5)

Geometric parameters (Å, º) top

O1—N3	1.2229 (16)	O2'—C7'	1.2196 (17)
O2—N3	1.2236 (16)	O3'—H3'	0.92 (2)
O3—C6	1.4378 (17)	O3'—C2'	1.3507 (17)
O3—C7	1.3441 (15)	C7'—C1'	1.4704 (19)
O4—C7	1.2015 (17)	C1'—C2'	1.3950 (19)
N1—C1	1.3518 (16)	C1'—C6'	1.3953 (19)
N1—C3	1.3803 (15)	C2'—C3'	1.391 (2)
N1—C5	1.4667 (16)	C3'—H3'A	0.951 (18)
N2—C1	1.3281 (18)	C3'—C4'	1.368 (2)
N2—C2	1.3509 (19)	C4'—H4'	1.001 (19)
N3—C3	1.4116 (17)	C4'—C5'	1.386 (2)
C1—C4	1.484 (2)	C5'—H5'	0.95 (2)
C2—H2	0.948 (17)	C5'—C6'	1.374 (2)
C2—C3	1.3514 (18)	C6'—H6'	1.019 (17)
C4—H4A	0.97 (3)	C9—C10	1.384 (2)
C4—H4B	0.94 (3)	C9—C8	1.385 (2)
C4—H4C	0.91 (3)	C9—H9	0.984 (17)
C5—H5A	0.969 (16)	C10—C11	1.369 (3)
C5—H5B	0.980 (16)	C10—H10	0.98 (2)
C5—C6	1.503 (2)	C11—C12	1.364 (3)
C6—H6A	0.988 (17)	C11—H11	1.02 (2)
C6—H6B	0.965 (17)	C12—C13	1.386 (3)
C7—C8	1.478 (2)	C12—H12	0.91 (2)
O1'—H1'	0.91 (2)	C13—C8	1.392 (2)
O1'—C7'	1.3111 (18)	C13—H13	0.925 (18)

C7—O3—C6	115.08 (11)	O1'—C7'—C1'	114.06 (12)
C1—N1—C3	105.29 (10)	O2'—C7'—O1'	122.59 (14)
C1—N1—C5	125.82 (11)	O2'—C7'—C1'	123.34 (14)
C3—N1—C5	128.73 (11)	C2'—C1'—C7'	120.02 (12)
C1—N2—C2	106.89 (11)	C2'—C1'—C6'	119.06 (12)
O1—N3—O2	124.02 (13)	C6'—C1'—C7'	120.90 (13)
O1—N3—C3	116.32 (12)	O3'—C2'—C1'	122.74 (13)
O2—N3—C3	119.66 (12)	O3'—C2'—C3'	117.89 (14)
N1—C1—C4	125.10 (15)	C3'—C2'—C1'	119.37 (13)
N2—C1—N1	111.15 (11)	C2'—C3'—H3'A	118.1 (11)
N2—C1—C4	123.75 (15)	C4'—C3'—C2'	120.49 (15)
N2—C2—H2	122.0 (10)	C4'—C3'—H3'A	121.4 (11)
N2—C2—C3	108.78 (12)	C3'—C4'—H4'	118.4 (11)
C3—C2—H2	129.2 (10)	C3'—C4'—C5'	120.82 (14)
N1—C3—N3	125.27 (11)	C5'—C4'—H4'	120.7 (11)
C2—C3—N1	107.88 (11)	C4'—C5'—H5'	120.2 (12)
C2—C3—N3	126.83 (12)	C6'—C5'—C4'	119.11 (15)
C1—C4—H4A	113.1 (19)	C6'—C5'—H5'	120.7 (12)
C1—C4—H4B	113.2 (17)	C1'—C6'—H6'	118.1 (9)
C1—C4—H4C	107.7 (19)	C5'—C6'—C1'	121.13 (14)
H4A—C4—H4B	102 (2)	C5'—C6'—H6'	120.8 (9)
H4A—C4—H4C	105 (2)	C10—C9—C8	120.28 (15)
H4B—C4—H4C	116 (3)	C10—C9—H9	120.7 (10)
N1—C5—H5A	106.3 (9)	C8—C9—H9	119.0 (10)
N1—C5—H5B	106.4 (9)	C9—C10—H10	121.0 (14)
N1—C5—C6	113.88 (11)	C11—C10—C9	120.15 (19)
H5A—C5—H5B	109.7 (13)	C11—C10—H10	118.8 (14)
C6—C5—H5A	109.7 (9)	C10—C11—H11	119.4 (13)
C6—C5—H5B	110.6 (9)	C12—C11—C10	120.21 (19)
O3—C6—C5	107.94 (12)	C12—C11—H11	120.3 (13)
O3—C6—H6A	109.8 (10)	C11—C12—C13	120.64 (18)
O3—C6—H6B	109.6 (10)	C11—C12—H12	122.2 (17)
C5—C6—H6A	111.0 (9)	C13—C12—H12	117.1 (17)
C5—C6—H6B	109.3 (10)	C12—C13—C8	119.65 (19)
H6A—C6—H6B	109.1 (13)	C12—C13—H13	122.8 (11)
O3—C7—C8	112.36 (11)	C8—C13—H13	117.5 (11)
O4—C7—O3	122.24 (13)	C9—C8—C7	122.78 (12)
O4—C7—C8	125.38 (12)	C9—C8—C13	119.05 (15)
C7'—O1'—H1'	111.8 (14)	C13—C8—C7	118.15 (14)
C2'—O3'—H3'	106.2 (14)

1-[2-(Benzoyloxy)ethyl]-2-methyl-5-nitro-1H-imidazol-3-ium 3-carboxyprop-2-enoate (bzmdmlc) top

Crystal data top

C₁₃H₁₄N₃O₄⁺·C₄H₃O₄⁻	F(000) = 1632
M_r = 391.33	D_x = 1.447 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 43.130 (3) Å	Cell parameters from 6422 reflections
b = 5.7944 (4) Å	θ = 2.7–26.1°
c = 15.2645 (11) Å	µ = 0.12 mm⁻¹
β = 109.600 (3)°	T = 302 K
V = 3593.7 (5) Å³	Prism, clear light colourless
Z = 8	0.57 × 0.23 × 0.05 mm

Data collection top

Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer	2159 reflections with I > 2σ(I)
Multilayer mirrors monochromator	R_int = 0.089
φ and ω scans	θ_max = 27.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −56→49
T_min = 0.261, T_max = 0.746	k = −7→7
20803 measured reflections	l = −19→19
4130 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.056	w = 1/[σ²(F_o²) + (0.0536P)² + 0.8177P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.147	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.18 e Å⁻³
4130 reflections	Δρ_min = −0.21 e Å⁻³
322 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0015 (3)

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O3	0.68004 (4)	0.6877 (3)	0.23662 (13)	0.0507 (5)
O1'	0.55288 (4)	−0.0276 (3)	0.21210 (14)	0.0618 (6)
O4	0.66174 (4)	0.3229 (3)	0.22612 (14)	0.0603 (5)
N1	0.61358 (4)	0.6620 (3)	0.25880 (13)	0.0390 (5)
N2	0.58882 (5)	0.3456 (4)	0.27408 (15)	0.0478 (5)
O3'	0.45356 (6)	0.2178 (3)	0.08155 (16)	0.0761 (6)
O2'	0.51306 (5)	0.2206 (3)	0.15210 (17)	0.0820 (7)
O4'	0.41448 (5)	−0.0382 (4)	0.03379 (16)	0.0823 (7)
O2	0.65266 (6)	0.9311 (4)	0.41184 (14)	0.0826 (7)
N3	0.64430 (5)	0.7380 (4)	0.42711 (17)	0.0569 (6)
O1	0.65247 (6)	0.6494 (4)	0.50428 (14)	0.0831 (7)
C3	0.62288 (6)	0.6050 (4)	0.35213 (17)	0.0421 (6)
C1	0.59273 (6)	0.4969 (4)	0.21254 (17)	0.0424 (6)
C8	0.71780 (6)	0.4014 (4)	0.31383 (17)	0.0434 (6)
C7	0.68393 (6)	0.4588 (4)	0.25489 (18)	0.0444 (6)
C5	0.62531 (7)	0.8476 (4)	0.2115 (2)	0.0442 (6)
C2	0.60735 (6)	0.4094 (4)	0.3611 (2)	0.0491 (7)
C6	0.64965 (7)	0.7620 (5)	0.1677 (2)	0.0495 (7)
C13	0.74353 (7)	0.5571 (5)	0.3278 (2)	0.0499 (7)
C1'	0.52336 (7)	0.0167 (4)	0.1699 (2)	0.0511 (7)
C2'	0.50025 (7)	−0.1817 (4)	0.1411 (2)	0.0532 (7)
C9	0.72408 (7)	0.1829 (4)	0.35499 (19)	0.0507 (7)
C4'	0.44353 (7)	0.0053 (5)	0.07005 (19)	0.0556 (7)
C3'	0.46770 (7)	−0.1857 (5)	0.1014 (2)	0.0543 (7)
C12	0.77498 (7)	0.4969 (5)	0.3810 (2)	0.0568 (7)
C11	0.78124 (8)	0.2810 (5)	0.4226 (2)	0.0587 (8)
C10	0.75578 (8)	0.1264 (5)	0.4091 (2)	0.0585 (8)
C4	0.57704 (9)	0.4779 (6)	0.1113 (2)	0.0587 (8)
H5A	0.6059 (6)	0.907 (4)	0.1597 (16)	0.045 (7)*
H13	0.7388 (6)	0.707 (4)	0.2973 (16)	0.052 (7)*
H5B	0.6357 (5)	0.968 (4)	0.2571 (16)	0.043 (7)*
H6A	0.6413 (6)	0.631 (5)	0.1212 (18)	0.063 (8)*
H2'	0.5118 (6)	−0.330 (4)	0.1577 (16)	0.055 (7)*
H2A	0.6072 (6)	0.328 (4)	0.4128 (17)	0.048 (7)*
H12	0.7929 (7)	0.609 (5)	0.3919 (18)	0.070 (9)*
H6B	0.6568 (6)	0.893 (5)	0.1377 (19)	0.067 (8)*
H10	0.7590 (6)	−0.031 (5)	0.4418 (19)	0.073 (9)*
H4A	0.5560 (9)	0.388 (6)	0.096 (2)	0.107 (12)*
H4B	0.5743 (8)	0.625 (6)	0.082 (2)	0.093 (11)*
H9	0.7040 (7)	0.076 (5)	0.3437 (19)	0.077 (9)*
H3'A	0.4572 (7)	−0.335 (5)	0.0881 (19)	0.073 (9)*
H2	0.5745 (8)	0.206 (5)	0.255 (2)	0.089 (10)*
H11	0.8042 (7)	0.243 (5)	0.4636 (19)	0.074 (9)*
H4C	0.5910 (8)	0.392 (6)	0.085 (2)	0.107 (13)*
H3'	0.4806 (11)	0.222 (6)	0.104 (3)	0.125 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0424 (10)	0.0375 (9)	0.0727 (12)	−0.0004 (8)	0.0200 (9)	0.0034 (8)
O1'	0.0417 (11)	0.0478 (11)	0.0899 (15)	−0.0047 (9)	0.0142 (10)	−0.0070 (10)
O4	0.0523 (11)	0.0405 (10)	0.0828 (14)	−0.0081 (9)	0.0158 (10)	−0.0015 (9)
N1	0.0381 (11)	0.0325 (10)	0.0461 (12)	−0.0026 (9)	0.0136 (10)	−0.0003 (9)
N2	0.0472 (13)	0.0411 (12)	0.0550 (14)	−0.0090 (10)	0.0171 (11)	−0.0029 (11)
O3'	0.0631 (14)	0.0454 (12)	0.1100 (18)	0.0084 (10)	0.0160 (13)	0.0107 (11)
O2'	0.0565 (13)	0.0390 (11)	0.140 (2)	−0.0027 (10)	0.0187 (14)	0.0045 (12)
O4'	0.0483 (13)	0.0800 (15)	0.1015 (17)	0.0036 (11)	0.0027 (12)	−0.0202 (13)
O2	0.0995 (17)	0.0666 (14)	0.0724 (15)	−0.0391 (13)	0.0165 (13)	−0.0087 (11)
N3	0.0533 (14)	0.0563 (14)	0.0560 (16)	−0.0119 (12)	0.0115 (12)	−0.0057 (12)
O1	0.0933 (17)	0.0892 (16)	0.0482 (13)	−0.0182 (13)	−0.0010 (12)	0.0089 (12)
C3	0.0391 (14)	0.0414 (13)	0.0442 (15)	−0.0025 (11)	0.0120 (12)	−0.0001 (11)
C1	0.0382 (13)	0.0389 (13)	0.0495 (16)	−0.0009 (11)	0.0139 (12)	−0.0009 (12)
C8	0.0455 (15)	0.0389 (13)	0.0502 (15)	−0.0023 (11)	0.0217 (13)	−0.0074 (11)
C7	0.0493 (16)	0.0345 (13)	0.0566 (16)	−0.0036 (12)	0.0273 (13)	−0.0049 (12)
C5	0.0449 (15)	0.0337 (13)	0.0541 (17)	−0.0012 (12)	0.0169 (14)	0.0069 (13)
C2	0.0500 (16)	0.0452 (15)	0.0514 (18)	−0.0066 (12)	0.0163 (14)	0.0037 (14)
C6	0.0489 (16)	0.0453 (15)	0.0570 (17)	−0.0004 (13)	0.0215 (14)	0.0077 (14)
C13	0.0472 (16)	0.0434 (15)	0.0611 (18)	−0.0022 (13)	0.0208 (14)	−0.0014 (13)
C1'	0.0471 (16)	0.0410 (15)	0.0672 (19)	−0.0036 (13)	0.0221 (14)	−0.0058 (13)
C2'	0.0520 (17)	0.0337 (13)	0.0702 (19)	−0.0014 (13)	0.0157 (15)	−0.0083 (13)
C9	0.0582 (18)	0.0403 (14)	0.0547 (17)	−0.0007 (14)	0.0205 (15)	−0.0046 (12)
C4'	0.0481 (17)	0.0578 (17)	0.0555 (18)	0.0052 (14)	0.0101 (14)	−0.0062 (14)
C3'	0.0491 (17)	0.0397 (15)	0.0679 (19)	−0.0043 (13)	0.0113 (14)	−0.0115 (13)
C12	0.0500 (17)	0.0546 (17)	0.068 (2)	−0.0046 (15)	0.0224 (15)	−0.0073 (15)
C11	0.0530 (18)	0.0646 (19)	0.0543 (18)	0.0110 (16)	0.0122 (15)	−0.0082 (15)
C10	0.071 (2)	0.0482 (16)	0.0541 (18)	0.0090 (16)	0.0189 (16)	−0.0020 (14)
C4	0.062 (2)	0.0612 (19)	0.0483 (18)	−0.0114 (17)	0.0126 (16)	−0.0067 (16)

Geometric parameters (Å, º) top

O3—C7	1.354 (3)	C5—C6	1.505 (4)
O3—C6	1.444 (3)	C5—H5A	1.00 (2)
O1'—C1'	1.246 (3)	C5—H5B	0.98 (2)
O4—C7	1.202 (3)	C2—H2A	0.92 (2)
N1—C3	1.384 (3)	C6—H6A	1.02 (3)
N1—C1	1.340 (3)	C6—H6B	0.99 (3)
N1—C5	1.476 (3)	C13—C12	1.372 (4)
N2—C1	1.336 (3)	C13—H13	0.97 (2)
N2—C2	1.351 (3)	C1'—C2'	1.488 (3)
N2—H2	1.00 (3)	C2'—C3'	1.330 (4)
O3'—C4'	1.297 (3)	C2'—H2'	0.98 (2)
O3'—H3'	1.10 (4)	C9—C10	1.379 (4)
O2'—C1'	1.259 (3)	C9—H9	1.03 (3)
O2'—H3'	1.35 (4)	C4'—C3'	1.485 (4)
O4'—C4'	1.214 (3)	C3'—H3'A	0.97 (3)
O2—N3	1.222 (3)	C12—C11	1.388 (4)
N3—O1	1.223 (3)	C12—H12	0.98 (3)
N3—C3	1.431 (3)	C11—C10	1.378 (4)
C3—C2	1.347 (3)	C11—H11	1.00 (3)
C1—C4	1.469 (4)	C10—H10	1.02 (3)
C8—C7	1.474 (3)	C4—H4A	1.00 (4)
C8—C13	1.390 (3)	C4—H4B	0.95 (3)
C8—C9	1.399 (3)	C4—H4C	0.96 (3)

C7—O3—C6	117.5 (2)	C5—C6—H6A	114.8 (15)
C3—N1—C5	130.4 (2)	C5—C6—H6B	109.1 (15)
C1—N1—C3	106.48 (19)	H6A—C6—H6B	110 (2)
C1—N1—C5	122.8 (2)	C8—C13—H13	118.5 (14)
C1—N2—C2	109.8 (2)	C12—C13—C8	120.4 (3)
C1—N2—H2	122.4 (17)	C12—C13—H13	121.0 (15)
C2—N2—H2	127.8 (17)	O1'—C1'—O2'	122.0 (2)
C4'—O3'—H3'	109.5 (19)	O1'—C1'—C2'	117.4 (2)
C1'—O2'—H3'	110.5 (16)	O2'—C1'—C2'	120.6 (2)
O2—N3—O1	124.0 (2)	C1'—C2'—H2'	111.7 (14)
O2—N3—C3	119.5 (2)	C3'—C2'—C1'	130.4 (3)
O1—N3—C3	116.4 (2)	C3'—C2'—H2'	117.9 (14)
N1—C3—N3	125.5 (2)	C8—C9—H9	116.3 (15)
C2—C3—N1	108.8 (2)	C10—C9—C8	119.2 (3)
C2—C3—N3	125.6 (2)	C10—C9—H9	124.5 (15)
N1—C1—C4	126.8 (2)	O3'—C4'—C3'	119.8 (2)
N2—C1—N1	108.6 (2)	O4'—C4'—O3'	120.3 (3)
N2—C1—C4	124.6 (2)	O4'—C4'—C3'	119.8 (3)
C13—C8—C7	121.6 (2)	C2'—C3'—C4'	130.8 (3)
C13—C8—C9	119.6 (3)	C2'—C3'—H3'A	117.3 (17)
C9—C8—C7	118.8 (2)	C4'—C3'—H3'A	111.9 (17)
O3—C7—C8	112.0 (2)	C13—C12—C11	120.1 (3)
O4—C7—O3	122.5 (2)	C13—C12—H12	119.9 (16)
O4—C7—C8	125.4 (2)	C11—C12—H12	119.9 (16)
N1—C5—C6	112.4 (2)	C12—C11—H11	119.0 (16)
N1—C5—H5A	107.7 (13)	C10—C11—C12	119.6 (3)
N1—C5—H5B	108.7 (13)	C10—C11—H11	121.3 (16)
C6—C5—H5A	106.7 (13)	C9—C10—H10	116.6 (16)
C6—C5—H5B	109.2 (13)	C11—C10—C9	121.0 (3)
H5A—C5—H5B	112.1 (18)	C11—C10—H10	122.3 (15)
N2—C2—H2A	121.9 (15)	C1—C4—H4A	110.6 (19)
C3—C2—N2	106.3 (2)	C1—C4—H4B	111.2 (19)
C3—C2—H2A	131.7 (15)	C1—C4—H4C	110 (2)
O3—C6—C5	111.9 (2)	H4A—C4—H4B	113 (3)
O3—C6—H6A	107.9 (15)	H4A—C4—H4C	106 (3)
O3—C6—H6B	102.6 (15)	H4B—C4—H4C	106 (3)

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–isophthalic acid (1/1) (bzmdiac) top

Crystal data top

C₁₃H₁₃N₃O₄·C₈H₆O₄	F(000) = 920
M_r = 441.39	D_x = 1.414 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.8300 (3) Å	Cell parameters from 9928 reflections
b = 33.7182 (10) Å	θ = 2.4–30.4°
c = 7.3199 (2) Å	µ = 0.11 mm⁻¹
β = 107.878 (1)°	T = 304 K
V = 2074.13 (11) Å³	Prism, clear light colourless
Z = 4	0.95 × 0.3 × 0.11 mm

Data collection top

Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer	4809 reflections with I > 2σ(I)
Multilayer mirrors monochromator	R_int = 0.037
φ and ω scans	θ_max = 30.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −12→12
T_min = 0.649, T_max = 0.746	k = −48→48
38842 measured reflections	l = −10→10
6344 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	All H-atom parameters refined
wR(F²) = 0.145	w = 1/[σ²(F_o²) + (0.0601P)² + 0.4881P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
6344 reflections	Δρ_max = 0.20 e Å⁻³
365 parameters	Δρ_min = −0.21 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O3	0.36882 (11)	0.28188 (3)	−0.12385 (16)	0.0549 (3)
O4'	1.31886 (13)	0.48005 (4)	0.42956 (16)	0.0617 (3)
O1'	0.78049 (13)	0.42754 (4)	0.32394 (16)	0.0610 (3)
O3'	1.47167 (13)	0.49211 (4)	0.72771 (17)	0.0697 (4)
N1	0.28442 (13)	0.36122 (3)	−0.03743 (16)	0.0452 (3)
O1	0.12528 (17)	0.37021 (4)	0.3517 (2)	0.0760 (4)
N2	0.48973 (15)	0.39681 (4)	0.13450 (19)	0.0537 (3)
N3	0.12377 (16)	0.36110 (4)	0.1893 (2)	0.0550 (3)
O2	0.01225 (15)	0.34423 (5)	0.0737 (2)	0.0833 (4)
O4	0.30372 (15)	0.21816 (4)	−0.1125 (3)	0.0846 (4)
O2'	0.68960 (17)	0.41614 (6)	0.5685 (2)	0.0982 (6)
C6'	1.07098 (15)	0.45287 (4)	0.5617 (2)	0.0431 (3)
C5'	1.21363 (15)	0.46743 (4)	0.68527 (19)	0.0438 (3)
C3	0.26003 (16)	0.37089 (4)	0.1350 (2)	0.0440 (3)
C8'	1.33969 (15)	0.48031 (4)	0.6041 (2)	0.0476 (3)
C1'	0.95064 (16)	0.44156 (4)	0.6348 (2)	0.0455 (3)
C8	0.56805 (17)	0.23453 (4)	−0.1057 (2)	0.0491 (3)
C1	0.42668 (17)	0.37765 (4)	−0.0295 (2)	0.0507 (3)
C2	0.38648 (18)	0.39278 (4)	0.2375 (2)	0.0509 (3)
C7	0.40177 (17)	0.24289 (5)	−0.1124 (2)	0.0526 (3)
C4'	1.23414 (18)	0.47070 (5)	0.8801 (2)	0.0522 (3)
C7'	0.79402 (18)	0.42688 (5)	0.5072 (2)	0.0539 (3)
C5	0.18737 (19)	0.33572 (5)	−0.1921 (2)	0.0544 (3)
C2'	0.97138 (19)	0.44485 (5)	0.8302 (2)	0.0552 (3)
C6	0.20736 (17)	0.29250 (5)	−0.1403 (3)	0.0539 (4)
C9	0.67651 (18)	0.26461 (5)	−0.0982 (3)	0.0578 (4)
C3'	1.1133 (2)	0.45954 (5)	0.9526 (2)	0.0585 (4)
C10	0.8293 (2)	0.25530 (6)	−0.0977 (3)	0.0664 (4)
C11	0.8741 (2)	0.21669 (6)	−0.1068 (3)	0.0664 (4)
C13	0.6152 (2)	0.19536 (5)	−0.1115 (3)	0.0669 (4)
C12	0.7681 (2)	0.18670 (6)	−0.1130 (3)	0.0739 (5)
C4	0.4995 (3)	0.37538 (8)	−0.1860 (4)	0.0781 (6)
H6'	1.0525 (19)	0.4509 (5)	0.425 (2)	0.049 (4)*
H5A	0.219 (2)	0.3419 (5)	−0.307 (3)	0.059 (5)*
H5B	0.077 (2)	0.3443 (5)	−0.217 (3)	0.060 (5)*
H6A	0.138 (2)	0.2775 (5)	−0.242 (3)	0.062 (5)*
H2	0.405 (2)	0.4048 (6)	0.365 (3)	0.066 (5)*
H4'	1.335 (2)	0.4810 (5)	0.964 (3)	0.059 (5)*
H6B	0.187 (2)	0.2868 (5)	−0.018 (3)	0.060 (5)*
H3'A	1.128 (2)	0.4626 (6)	1.089 (3)	0.072 (5)*
H9	0.645 (2)	0.2931 (6)	−0.091 (3)	0.076 (6)*
H13	0.538 (3)	0.1757 (7)	−0.116 (3)	0.083 (6)*
H2'	0.881 (2)	0.4366 (6)	0.884 (3)	0.074 (6)*
H1'	0.683 (3)	0.4171 (7)	0.249 (3)	0.099 (7)*
H11	0.983 (3)	0.2095 (6)	−0.109 (3)	0.084 (6)*
H10	0.906 (3)	0.2768 (6)	−0.092 (3)	0.080 (6)*
H12	0.796 (3)	0.1580 (7)	−0.126 (3)	0.091 (7)*
H4A	0.493 (4)	0.3484 (12)	−0.248 (5)	0.150 (12)*
H4B	0.598 (5)	0.3788 (12)	−0.136 (5)	0.154 (14)*
H3'	1.543 (4)	0.5032 (9)	0.655 (4)	0.125 (9)*
H4C	0.469 (5)	0.3945 (12)	−0.266 (6)	0.163 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0382 (5)	0.0566 (6)	0.0703 (7)	−0.0101 (4)	0.0171 (5)	−0.0127 (5)
O4'	0.0450 (5)	0.0863 (8)	0.0503 (6)	−0.0193 (5)	0.0093 (5)	−0.0118 (5)
O1'	0.0457 (5)	0.0788 (8)	0.0533 (6)	−0.0230 (5)	0.0073 (5)	−0.0005 (5)
O3'	0.0412 (5)	0.1084 (10)	0.0535 (6)	−0.0234 (6)	0.0055 (5)	−0.0159 (6)
N1	0.0418 (5)	0.0493 (6)	0.0435 (6)	−0.0070 (5)	0.0115 (4)	0.0015 (5)
O1	0.0815 (9)	0.0851 (9)	0.0766 (8)	−0.0039 (7)	0.0465 (7)	−0.0137 (7)
N2	0.0459 (6)	0.0519 (7)	0.0593 (7)	−0.0118 (5)	0.0102 (5)	0.0050 (5)
N3	0.0505 (7)	0.0522 (7)	0.0681 (8)	−0.0035 (5)	0.0269 (6)	−0.0042 (6)
O2	0.0555 (7)	0.1038 (10)	0.0973 (10)	−0.0306 (7)	0.0334 (7)	−0.0289 (8)
O4	0.0567 (7)	0.0643 (8)	0.1410 (13)	−0.0193 (6)	0.0427 (8)	−0.0104 (8)
O2'	0.0695 (8)	0.1590 (15)	0.0670 (8)	−0.0616 (9)	0.0225 (7)	−0.0070 (9)
C6'	0.0385 (6)	0.0428 (6)	0.0438 (7)	−0.0046 (5)	0.0067 (5)	−0.0041 (5)
C5'	0.0375 (6)	0.0416 (6)	0.0479 (7)	−0.0009 (5)	0.0067 (5)	−0.0034 (5)
C3	0.0405 (6)	0.0434 (6)	0.0481 (7)	−0.0028 (5)	0.0134 (5)	0.0009 (5)
C8'	0.0353 (6)	0.0517 (7)	0.0497 (7)	−0.0039 (5)	0.0041 (5)	−0.0087 (6)
C1'	0.0413 (6)	0.0425 (6)	0.0497 (7)	−0.0051 (5)	0.0092 (5)	−0.0002 (5)
C8	0.0444 (7)	0.0548 (8)	0.0476 (7)	−0.0079 (6)	0.0135 (6)	−0.0088 (6)
C1	0.0459 (7)	0.0529 (8)	0.0538 (8)	−0.0077 (6)	0.0162 (6)	0.0088 (6)
C2	0.0500 (7)	0.0476 (7)	0.0517 (8)	−0.0063 (6)	0.0104 (6)	−0.0012 (6)
C7	0.0454 (7)	0.0569 (8)	0.0566 (8)	−0.0129 (6)	0.0170 (6)	−0.0117 (6)
C4'	0.0453 (7)	0.0558 (8)	0.0486 (7)	−0.0023 (6)	0.0040 (6)	−0.0054 (6)
C7'	0.0463 (7)	0.0564 (8)	0.0570 (8)	−0.0159 (6)	0.0128 (6)	0.0003 (6)
C5	0.0444 (7)	0.0689 (9)	0.0445 (7)	−0.0055 (7)	0.0054 (6)	−0.0050 (6)
C2'	0.0510 (8)	0.0609 (9)	0.0536 (8)	−0.0032 (7)	0.0158 (7)	0.0033 (7)
C6	0.0353 (6)	0.0627 (9)	0.0614 (9)	−0.0116 (6)	0.0115 (6)	−0.0147 (7)
C9	0.0441 (7)	0.0587 (9)	0.0722 (10)	−0.0089 (6)	0.0201 (7)	−0.0106 (7)
C3'	0.0577 (9)	0.0701 (10)	0.0446 (7)	−0.0016 (7)	0.0111 (6)	−0.0018 (7)
C10	0.0454 (8)	0.0737 (11)	0.0820 (12)	−0.0092 (8)	0.0224 (8)	−0.0097 (9)
C11	0.0487 (8)	0.0821 (12)	0.0681 (10)	0.0060 (8)	0.0177 (8)	−0.0065 (9)
C13	0.0632 (10)	0.0555 (9)	0.0840 (12)	−0.0094 (8)	0.0254 (9)	−0.0075 (8)
C12	0.0688 (11)	0.0645 (11)	0.0887 (13)	0.0105 (9)	0.0250 (10)	−0.0045 (9)
C4	0.0825 (15)	0.0893 (15)	0.0776 (13)	−0.0158 (12)	0.0468 (12)	0.0077 (12)

Geometric parameters (Å, º) top

O3—C7	1.3435 (19)	C8—C9	1.384 (2)
O3—C6	1.4388 (17)	C8—C13	1.389 (2)
O4'—C8'	1.2338 (18)	C1—C4	1.478 (3)
O1'—C7'	1.3101 (19)	C2—H2	0.983 (19)
O1'—H1'	0.93 (3)	C4'—C3'	1.382 (2)
O3'—C8'	1.2991 (16)	C4'—H4'	0.973 (19)
O3'—H3'	1.02 (3)	C5—C6	1.502 (2)
N1—C3	1.3829 (18)	C5—H5A	0.989 (18)
N1—C1	1.3578 (17)	C5—H5B	0.976 (18)
N1—C5	1.4694 (18)	C2'—C3'	1.389 (2)
O1—N3	1.2243 (18)	C2'—H2'	1.03 (2)
N2—C1	1.326 (2)	C6—H6A	0.952 (19)
N2—C2	1.357 (2)	C6—H6B	0.988 (18)
N3—O2	1.2236 (18)	C9—C10	1.384 (2)
N3—C3	1.4171 (18)	C9—H9	1.01 (2)
O4—C7	1.2019 (18)	C3'—H3'A	0.97 (2)
O2'—C7'	1.1986 (19)	C10—C11	1.368 (3)
C6'—C5'	1.3953 (18)	C10—H10	0.98 (2)
C6'—C1'	1.3821 (19)	C11—C12	1.369 (3)
C6'—H6'	0.968 (16)	C11—H11	1.00 (2)
C5'—C8'	1.479 (2)	C13—C12	1.385 (3)
C5'—C4'	1.386 (2)	C13—H13	0.94 (2)
C3—C2	1.3564 (19)	C12—H12	1.01 (2)
C1'—C7'	1.4955 (19)	C4—H4A	1.01 (4)
C1'—C2'	1.389 (2)	C4—H4B	0.84 (4)
C8—C7	1.481 (2)	C4—H4C	0.86 (4)

C7—O3—C6	116.03 (11)	O2'—C7'—O1'	123.34 (14)
C7'—O1'—H1'	111.7 (15)	O2'—C7'—C1'	122.45 (15)
C8'—O3'—H3'	108.4 (16)	N1—C5—C6	112.20 (13)
C3—N1—C5	128.58 (12)	N1—C5—H5A	106.5 (10)
C1—N1—C3	105.42 (11)	N1—C5—H5B	106.3 (10)
C1—N1—C5	125.80 (13)	C6—C5—H5A	112.2 (10)
C1—N2—C2	106.69 (12)	C6—C5—H5B	111.5 (10)
O1—N3—C3	117.19 (13)	H5A—C5—H5B	107.7 (15)
O2—N3—O1	123.67 (14)	C1'—C2'—H2'	120.0 (11)
O2—N3—C3	119.14 (13)	C3'—C2'—C1'	120.03 (15)
C5'—C6'—H6'	121.9 (10)	C3'—C2'—H2'	119.9 (11)
C1'—C6'—C5'	119.62 (13)	O3—C6—C5	107.41 (12)
C1'—C6'—H6'	118.5 (10)	O3—C6—H6A	108.6 (11)
C6'—C5'—C8'	118.94 (12)	O3—C6—H6B	109.3 (11)
C4'—C5'—C6'	120.14 (13)	C5—C6—H6A	108.8 (11)
C4'—C5'—C8'	120.90 (12)	C5—C6—H6B	112.1 (10)
N1—C3—N3	125.76 (12)	H6A—C6—H6B	110.6 (15)
C2—C3—N1	107.51 (12)	C8—C9—H9	120.0 (12)
C2—C3—N3	126.67 (13)	C10—C9—C8	119.72 (16)
O4'—C8'—O3'	122.69 (14)	C10—C9—H9	120.3 (12)
O4'—C8'—C5'	121.51 (12)	C4'—C3'—C2'	119.96 (15)
O3'—C8'—C5'	115.80 (13)	C4'—C3'—H3'A	119.1 (12)
C6'—C1'—C7'	121.54 (13)	C2'—C3'—H3'A	120.9 (12)
C6'—C1'—C2'	120.17 (13)	C9—C10—H10	119.3 (13)
C2'—C1'—C7'	118.26 (13)	C11—C10—C9	120.78 (17)
C9—C8—C7	121.91 (14)	C11—C10—H10	119.9 (13)
C9—C8—C13	119.19 (15)	C10—C11—C12	119.97 (17)
C13—C8—C7	118.88 (14)	C10—C11—H11	121.8 (12)
N1—C1—C4	124.24 (16)	C12—C11—H11	118.2 (12)
N2—C1—N1	111.31 (13)	C8—C13—H13	116.8 (13)
N2—C1—C4	124.42 (16)	C12—C13—C8	120.17 (17)
N2—C2—C3	109.07 (13)	C12—C13—H13	123.1 (13)
N2—C2—H2	122.9 (11)	C11—C12—C13	120.15 (18)
C3—C2—H2	128.1 (11)	C11—C12—H12	121.6 (13)
O3—C7—C8	112.45 (12)	C13—C12—H12	118.2 (13)
O4—C7—O3	122.45 (14)	C1—C4—H4A	114.7 (19)
O4—C7—C8	125.08 (15)	C1—C4—H4B	107 (2)
C5'—C4'—H4'	118.9 (10)	C1—C4—H4C	112 (3)
C3'—C4'—C5'	120.08 (14)	H4A—C4—H4B	103 (3)
C3'—C4'—H4'	121.1 (10)	H4A—C4—H4C	114 (3)
O1'—C7'—C1'	114.20 (12)	H4B—C4—H4C	105 (3)

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–resorcinol (2/1) (bzmdres) top

Crystal data top

2C₁₃H₁₃N₃O₄·C₆H₆O₂	D_x = 1.376 Mg m⁻³
M_r = 660.63	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbca	Cell parameters from 9896 reflections
a = 26.3241 (4) Å	θ = 3.1–68.2°
b = 7.1612 (1) Å	µ = 0.88 mm⁻¹
c = 33.8433 (5) Å	T = 300 K
V = 6379.87 (16) Å³	Plate, clear light colourless
Z = 8	0.25 × 0.12 × 0.11 mm
F(000) = 2768

Data collection top

Bruker APEXII CCD diffractometer	4816 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.066
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 68.3°, θ_min = 2.6°
T_min = 0.623, T_max = 0.753	h = −31→31
121051 measured reflections	k = −8→8
5865 independent reflections	l = −40→40

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.0733P)² + 1.6636P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.147	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.30 e Å⁻³
5865 reflections	Δρ_min = −0.31 e Å⁻³
540 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00043 (6)
Primary atom site location: dual

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O3B	0.29177 (5)	0.7763 (2)	0.21878 (3)	0.0676 (3)
O3A	0.70575 (5)	−0.1189 (2)	0.52879 (4)	0.0691 (3)
N1A	0.60485 (5)	−0.0111 (2)	0.55009 (4)	0.0594 (4)
N1B	0.39439 (5)	0.6490 (2)	0.19753 (4)	0.0606 (4)
O4B	0.21161 (6)	0.7410 (3)	0.19886 (5)	0.0946 (5)
N2A	0.55969 (6)	0.1485 (2)	0.50650 (5)	0.0698 (4)
O2'	0.52718 (8)	0.3814 (3)	0.44659 (5)	0.0978 (5)
O4A	0.78574 (6)	−0.1384 (3)	0.55011 (5)	0.1011 (6)
N2B	0.44240 (6)	0.5183 (3)	0.24363 (5)	0.0721 (4)
O1'	0.48855 (7)	0.5514 (3)	0.31647 (5)	0.1049 (6)
O2A	0.63071 (7)	0.1226 (3)	0.62598 (5)	0.1110 (6)
N3A	0.61124 (7)	0.2312 (3)	0.60258 (6)	0.0859 (5)
C8B	0.22773 (7)	0.8238 (2)	0.26590 (5)	0.0603 (4)
O2B	0.36980 (8)	0.4818 (4)	0.12448 (6)	0.1210 (7)
N3B	0.39162 (7)	0.3882 (3)	0.14929 (7)	0.0919 (6)
C8A	0.77042 (7)	−0.0609 (2)	0.48271 (5)	0.0616 (4)
C3A	0.59504 (6)	0.1642 (3)	0.56527 (5)	0.0629 (4)
O1A	0.60434 (8)	0.3983 (3)	0.60894 (7)	0.1274 (8)
C7B	0.24133 (7)	0.7746 (3)	0.22482 (5)	0.0637 (4)
C1B	0.41703 (7)	0.6707 (3)	0.23323 (5)	0.0633 (4)
C1A	0.58274 (7)	−0.0115 (3)	0.51389 (5)	0.0647 (4)
C7A	0.75635 (7)	−0.1104 (3)	0.52361 (5)	0.0660 (5)
C9A	0.73439 (8)	−0.0105 (3)	0.45482 (5)	0.0644 (4)
C3B	0.40651 (6)	0.4703 (3)	0.18565 (6)	0.0661 (5)
C2A	0.56744 (7)	0.2580 (3)	0.53836 (6)	0.0678 (5)
C6'	0.51323 (7)	0.3226 (3)	0.40973 (6)	0.0687 (5)
C2'	0.49229 (7)	0.4103 (3)	0.34347 (6)	0.0721 (5)
C9B	0.26411 (8)	0.8558 (3)	0.29468 (6)	0.0689 (5)
C1'	0.50863 (8)	0.4587 (3)	0.38117 (6)	0.0741 (5)
C2B	0.43581 (7)	0.3946 (3)	0.21394 (7)	0.0730 (5)
C3'	0.48105 (7)	0.2277 (3)	0.33438 (6)	0.0734 (5)
C5'	0.50283 (8)	0.1381 (3)	0.40091 (7)	0.0735 (5)
C6B	0.30779 (8)	0.7433 (4)	0.17856 (6)	0.0731 (5)
C5B	0.36357 (8)	0.7879 (3)	0.17681 (7)	0.0741 (5)
C5A	0.63229 (9)	−0.1684 (3)	0.56795 (7)	0.0777 (6)
C13B	0.17693 (8)	0.8428 (4)	0.27569 (7)	0.0797 (6)
C13A	0.82152 (8)	−0.0597 (3)	0.47209 (8)	0.0801 (6)
C10A	0.74957 (10)	0.0442 (3)	0.41755 (6)	0.0790 (6)
C4'	0.48680 (8)	0.0933 (3)	0.36331 (7)	0.0780 (5)
C10B	0.24940 (10)	0.9079 (3)	0.33226 (6)	0.0824 (6)
C6A	0.68875 (9)	−0.1410 (5)	0.56883 (6)	0.0838 (7)
C11B	0.19922 (10)	0.9302 (4)	0.34139 (7)	0.0853 (6)
O1B	0.40194 (8)	0.2250 (4)	0.14505 (9)	0.1469 (10)
C11A	0.79998 (11)	0.0491 (3)	0.40780 (8)	0.0891 (7)
C12A	0.83596 (10)	−0.0054 (4)	0.43460 (8)	0.0919 (7)
C4B	0.41432 (9)	0.8429 (4)	0.25758 (8)	0.0914 (7)
H4BA	0.436862	0.935305	0.246868	0.137*
H4BB	0.424152	0.814614	0.284228	0.137*
H4BC	0.380182	0.890062	0.257375	0.137*
C4A	0.58372 (10)	−0.1713 (4)	0.48615 (8)	0.0960 (7)
H4AA	0.617788	−0.218047	0.484027	0.144*
H4AB	0.572169	−0.131042	0.460625	0.144*
H4AC	0.561838	−0.268338	0.495797	0.144*
C12B	0.16312 (10)	0.8963 (4)	0.31324 (8)	0.0908 (7)
H3'	0.4671 (5)	0.1999 (19)	0.3050 (4)	0.036 (3)*
H5'	0.5072 (7)	0.034 (3)	0.4230 (5)	0.058 (5)*
H6BA	0.2885 (8)	0.827 (3)	0.1608 (7)	0.077 (6)*
H2A	0.5542 (9)	0.370 (4)	0.5409 (7)	0.081 (7)*
H9A	0.6979 (8)	−0.011 (3)	0.4627 (6)	0.075 (6)*
H1'A	0.5167 (8)	0.593 (3)	0.3891 (7)	0.081 (6)*
H13A	0.8432 (9)	−0.106 (3)	0.4913 (7)	0.082 (7)*
H4'	0.4801 (9)	−0.041 (4)	0.3582 (7)	0.090 (7)*
H5AA	0.6207 (10)	−0.178 (4)	0.5943 (9)	0.100 (8)*
H2B	0.4502 (9)	0.278 (4)	0.2145 (7)	0.093 (7)*
H9B	0.3015 (9)	0.846 (3)	0.2874 (7)	0.090 (7)*
H6BB	0.2999 (9)	0.602 (4)	0.1714 (7)	0.092 (7)*
H6AA	0.7045 (10)	−0.250 (4)	0.5801 (8)	0.103 (8)*
H5BA	0.3718 (9)	0.909 (3)	0.1898 (7)	0.084 (7)*
H11B	0.1864 (9)	0.985 (4)	0.3692 (8)	0.098 (7)*
H6AB	0.6966 (11)	−0.033 (4)	0.5822 (9)	0.103 (9)*
H13B	0.1530 (10)	0.809 (4)	0.2561 (8)	0.105 (8)*
H5BB	0.3746 (9)	0.788 (3)	0.1508 (8)	0.093 (7)*
H5AB	0.6241 (9)	−0.280 (4)	0.5517 (7)	0.086 (7)*
H11A	0.8124 (10)	0.095 (4)	0.3826 (9)	0.110 (9)*
H10A	0.7236 (10)	0.082 (4)	0.3987 (8)	0.103 (8)*
H10B	0.2797 (12)	0.934 (4)	0.3530 (9)	0.127 (10)*
H12B	0.1301 (11)	0.918 (4)	0.3203 (8)	0.109 (9)*
H12A	0.8730 (12)	−0.002 (4)	0.4288 (9)	0.124 (10)*
H1'	0.4698 (13)	0.507 (5)	0.2907 (11)	0.145 (12)*
H2'	0.5357 (15)	0.266 (6)	0.4639 (12)	0.174 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3B	0.0638 (7)	0.0860 (9)	0.0530 (6)	0.0111 (6)	−0.0044 (5)	0.0048 (6)
O3A	0.0637 (7)	0.0888 (9)	0.0549 (7)	0.0131 (6)	−0.0043 (5)	0.0036 (6)
N1A	0.0560 (7)	0.0656 (8)	0.0567 (8)	0.0012 (6)	0.0005 (6)	0.0059 (7)
N1B	0.0565 (8)	0.0702 (9)	0.0550 (8)	−0.0013 (7)	0.0003 (6)	0.0026 (7)
O4B	0.0744 (9)	0.1351 (14)	0.0744 (9)	0.0050 (9)	−0.0176 (7)	−0.0187 (9)
N2A	0.0701 (9)	0.0748 (10)	0.0646 (9)	0.0050 (8)	−0.0072 (7)	0.0050 (8)
O2'	0.1317 (14)	0.0893 (11)	0.0724 (9)	0.0065 (10)	−0.0237 (9)	0.0092 (8)
O4A	0.0755 (9)	0.1502 (16)	0.0777 (10)	0.0214 (10)	−0.0196 (8)	0.0123 (10)
N2B	0.0614 (8)	0.0855 (11)	0.0694 (9)	−0.0011 (8)	−0.0056 (7)	0.0111 (8)
O1'	0.1253 (14)	0.1048 (12)	0.0845 (10)	−0.0311 (10)	−0.0359 (10)	0.0347 (9)
O2A	0.0989 (12)	0.1692 (19)	0.0649 (9)	0.0149 (12)	−0.0146 (8)	−0.0071 (11)
N3A	0.0617 (9)	0.1170 (16)	0.0789 (11)	0.0060 (10)	−0.0095 (8)	−0.0261 (12)
C8B	0.0630 (9)	0.0559 (9)	0.0620 (9)	0.0073 (7)	−0.0047 (7)	0.0082 (8)
O2B	0.1083 (13)	0.177 (2)	0.0778 (10)	0.0200 (14)	−0.0198 (10)	−0.0295 (12)
N3B	0.0644 (10)	0.1138 (16)	0.0974 (14)	0.0070 (10)	−0.0029 (10)	−0.0408 (13)
C8A	0.0653 (10)	0.0546 (9)	0.0650 (10)	0.0009 (7)	−0.0032 (8)	−0.0134 (8)
C3A	0.0531 (9)	0.0731 (11)	0.0626 (10)	−0.0047 (8)	0.0008 (7)	−0.0051 (8)
O1A	0.1041 (13)	0.1358 (17)	0.1422 (18)	0.0224 (12)	−0.0328 (12)	−0.0735 (15)
C7B	0.0642 (10)	0.0633 (10)	0.0637 (10)	0.0086 (8)	−0.0112 (8)	0.0031 (8)
C1B	0.0574 (9)	0.0748 (11)	0.0578 (9)	−0.0063 (8)	0.0001 (7)	0.0008 (8)
C1A	0.0600 (9)	0.0712 (11)	0.0631 (10)	0.0022 (8)	−0.0023 (8)	−0.0012 (9)
C7A	0.0638 (10)	0.0679 (11)	0.0663 (10)	0.0121 (8)	−0.0102 (8)	−0.0054 (9)
C9A	0.0735 (11)	0.0595 (10)	0.0603 (10)	0.0014 (9)	−0.0032 (8)	−0.0057 (8)
C3B	0.0542 (9)	0.0754 (12)	0.0686 (11)	−0.0017 (8)	0.0020 (8)	−0.0090 (9)
C2A	0.0649 (10)	0.0597 (11)	0.0789 (12)	0.0006 (9)	−0.0028 (9)	0.0007 (9)
C6'	0.0618 (10)	0.0817 (13)	0.0626 (10)	0.0057 (9)	−0.0018 (8)	0.0095 (9)
C2'	0.0595 (10)	0.0903 (14)	0.0665 (11)	−0.0062 (9)	−0.0054 (8)	0.0188 (10)
C9B	0.0677 (11)	0.0771 (12)	0.0620 (10)	0.0084 (9)	−0.0060 (8)	0.0044 (9)
C1'	0.0758 (12)	0.0728 (12)	0.0737 (12)	−0.0028 (10)	−0.0119 (9)	0.0096 (10)
C2B	0.0590 (10)	0.0697 (12)	0.0901 (14)	0.0022 (9)	0.0012 (9)	0.0022 (11)
C3'	0.0629 (10)	0.0871 (14)	0.0702 (12)	−0.0060 (10)	0.0006 (9)	0.0015 (10)
C5'	0.0661 (11)	0.0772 (13)	0.0771 (12)	0.0032 (9)	0.0049 (9)	0.0168 (10)
C6B	0.0735 (11)	0.0950 (15)	0.0507 (9)	0.0169 (11)	−0.0042 (8)	0.0097 (10)
C5B	0.0786 (12)	0.0832 (14)	0.0604 (11)	0.0058 (10)	0.0039 (9)	0.0183 (10)
C5A	0.0805 (13)	0.0806 (14)	0.0720 (13)	0.0147 (11)	0.0060 (10)	0.0226 (11)
C13B	0.0654 (11)	0.0961 (15)	0.0777 (13)	0.0082 (11)	−0.0049 (10)	0.0039 (11)
C13A	0.0679 (11)	0.0853 (14)	0.0870 (15)	−0.0032 (10)	−0.0037 (11)	−0.0200 (12)
C10A	0.1019 (15)	0.0701 (12)	0.0649 (11)	−0.0068 (11)	−0.0003 (12)	−0.0053 (9)
C4'	0.0696 (12)	0.0771 (13)	0.0872 (14)	−0.0044 (10)	0.0064 (10)	0.0008 (11)
C10B	0.0908 (14)	0.0944 (15)	0.0621 (11)	0.0141 (12)	−0.0076 (11)	0.0014 (10)
C6A	0.0753 (13)	0.118 (2)	0.0580 (11)	0.0275 (13)	0.0007 (9)	0.0181 (13)
C11B	0.0988 (16)	0.0913 (15)	0.0657 (12)	0.0218 (12)	0.0088 (11)	0.0113 (11)
O1B	0.1119 (15)	0.1435 (19)	0.185 (2)	0.0282 (14)	−0.0336 (15)	−0.0900 (18)
C11A	0.1141 (19)	0.0790 (14)	0.0743 (14)	−0.0256 (13)	0.0189 (14)	−0.0207 (11)
C12A	0.0846 (15)	0.0949 (16)	0.0961 (17)	−0.0210 (13)	0.0233 (14)	−0.0306 (14)
C4B	0.0849 (14)	0.0990 (16)	0.0902 (15)	−0.0038 (12)	−0.0086 (12)	−0.0245 (13)
C4A	0.0959 (16)	0.0983 (17)	0.0939 (16)	0.0162 (13)	−0.0162 (13)	−0.0305 (14)
C12B	0.0744 (13)	0.1126 (19)	0.0853 (15)	0.0143 (13)	0.0163 (12)	0.0081 (13)

Geometric parameters (Å, º) top

O3B—C7B	1.344 (2)	N3B—C3B	1.419 (3)
O3B—C6B	1.444 (2)	N3B—O1B	1.208 (3)
O3A—C7A	1.345 (2)	C8A—C7A	1.476 (3)
O3A—C6A	1.436 (2)	C8A—C9A	1.386 (3)
N1A—C3A	1.381 (2)	C8A—C13A	1.392 (3)
N1A—C1A	1.356 (2)	C3A—C2A	1.344 (3)
N1A—C5A	1.468 (2)	C1B—C4B	1.485 (3)
N1B—C1B	1.356 (2)	C1A—C4A	1.480 (3)
N1B—C3B	1.379 (3)	C9A—C10A	1.380 (3)
N1B—C5B	1.462 (3)	C3B—C2B	1.344 (3)
O4B—C7B	1.201 (2)	C6'—C1'	1.378 (3)
N2A—C1A	1.321 (3)	C6'—C5'	1.382 (3)
N2A—C2A	1.348 (3)	C2'—C1'	1.390 (3)
O2'—C6'	1.367 (3)	C2'—C3'	1.376 (3)
O4A—C7A	1.201 (2)	C9B—C10B	1.381 (3)
N2B—C1B	1.327 (3)	C3'—C4'	1.381 (3)
N2B—C2B	1.350 (3)	C5'—C4'	1.378 (3)
O1'—C2'	1.366 (3)	C6B—C5B	1.504 (3)
O2A—N3A	1.223 (3)	C5A—C6A	1.500 (3)
N3A—C3A	1.417 (3)	C13B—C12B	1.376 (3)
N3A—O1A	1.229 (3)	C13A—C12A	1.380 (4)
C8B—C7B	1.478 (3)	C10A—C11A	1.368 (4)
C8B—C9B	1.385 (3)	C10B—C11B	1.366 (3)
C8B—C13B	1.384 (3)	C11B—C12B	1.367 (4)
O2B—N3B	1.218 (3)	C11A—C12A	1.368 (4)

C7B—O3B—C6B	115.49 (14)	N2A—C1A—C4A	123.95 (18)
C7A—O3A—C6A	115.89 (15)	O3A—C7A—C8A	112.42 (15)
C3A—N1A—C5A	129.51 (17)	O4A—C7A—O3A	122.22 (19)
C1A—N1A—C3A	104.96 (15)	O4A—C7A—C8A	125.35 (19)
C1A—N1A—C5A	125.52 (18)	C10A—C9A—C8A	119.9 (2)
C1B—N1B—C3B	105.33 (15)	N1B—C3B—N3B	125.01 (19)
C1B—N1B—C5B	126.37 (17)	C2B—C3B—N1B	107.44 (18)
C3B—N1B—C5B	128.30 (17)	C2B—C3B—N3B	127.5 (2)
C1A—N2A—C2A	106.47 (16)	C3A—C2A—N2A	109.46 (18)
C1B—N2B—C2B	106.10 (16)	O2'—C6'—C1'	116.5 (2)
O2A—N3A—C3A	119.2 (2)	O2'—C6'—C5'	123.01 (18)
O2A—N3A—O1A	124.6 (2)	C1'—C6'—C5'	120.5 (2)
O1A—N3A—C3A	116.2 (2)	O1'—C2'—C1'	116.9 (2)
C9B—C8B—C7B	122.23 (17)	O1'—C2'—C3'	122.55 (19)
C13B—C8B—C7B	118.84 (17)	C3'—C2'—C1'	120.55 (19)
C13B—C8B—C9B	118.91 (19)	C10B—C9B—C8B	119.90 (19)
O2B—N3B—C3B	120.0 (2)	C6'—C1'—C2'	119.7 (2)
O1B—N3B—O2B	123.8 (2)	C3B—C2B—N2B	109.83 (19)
O1B—N3B—C3B	116.2 (2)	C2'—C3'—C4'	118.7 (2)
C9A—C8A—C7A	121.98 (17)	C4'—C5'—C6'	118.9 (2)
C9A—C8A—C13A	118.92 (19)	O3B—C6B—C5B	106.70 (17)
C13A—C8A—C7A	119.07 (18)	N1B—C5B—C6B	112.24 (17)
N1A—C3A—N3A	125.69 (18)	N1A—C5A—C6A	113.3 (2)
C2A—C3A—N1A	107.63 (17)	C12B—C13B—C8B	120.2 (2)
C2A—C3A—N3A	126.7 (2)	C12A—C13A—C8A	120.3 (2)
O3B—C7B—C8B	112.35 (15)	C11A—C10A—C9A	120.6 (2)
O4B—C7B—O3B	122.31 (18)	C5'—C4'—C3'	121.7 (2)
O4B—C7B—C8B	125.32 (18)	C11B—C10B—C9B	120.7 (2)
N1B—C1B—C4B	124.64 (18)	O3A—C6A—C5A	107.72 (18)
N2B—C1B—N1B	111.30 (17)	C10B—C11B—C12B	119.6 (2)
N2B—C1B—C4B	124.06 (18)	C10A—C11A—C12A	120.3 (2)
N1A—C1A—C4A	124.57 (18)	C11A—C12A—C13A	119.9 (2)
N2A—C1A—N1A	111.47 (17)	C11B—C12B—C13B	120.6 (2)

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–fumaric acid (2/1) (bzmdfma) top

Crystal data top

C₁₃H₁₃N₃O₄·0.5C₄H₄O₄	F(000) = 696
M_r = 333.30	D_x = 1.369 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.0358 (5) Å	Cell parameters from 9988 reflections
b = 26.6419 (14) Å	θ = 2.3–28.9°
c = 6.8796 (3) Å	µ = 0.11 mm⁻¹
β = 102.419 (2)°	T = 300 K
V = 1617.38 (14) Å³	Prism, clear light colourless
Z = 4	0.63 × 0.17 × 0.17 mm

Data collection top

Bruker APEXII CCD diffractometer	2625 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.066
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 27.5°, θ_min = 2.8°
T_min = 0.620, T_max = 0.746	h = −11→11
46849 measured reflections	k = −34→34
3705 independent reflections	l = −8→8

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0568P)² + 0.5999P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.151	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.39 e Å⁻³
3705 reflections	Δρ_min = −0.33 e Å⁻³
267 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.018 (3)
Primary atom site location: dual

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.8887 (3)	0.59652 (9)	0.3299 (4)	0.1261 (9)
O2	0.9417 (2)	0.62892 (9)	0.6242 (4)	0.1134 (8)
O3	0.55707 (16)	0.70919 (5)	0.7641 (2)	0.0614 (4)
O4	0.6408 (2)	0.78808 (6)	0.7663 (3)	0.0818 (5)
N1	0.64502 (18)	0.60717 (6)	0.6676 (2)	0.0535 (4)
N2	0.4807 (2)	0.56134 (6)	0.4570 (3)	0.0640 (5)
N3	0.8562 (3)	0.60697 (8)	0.4893 (4)	0.0820 (6)
C1	0.5053 (2)	0.58656 (7)	0.6269 (3)	0.0574 (5)
C2	0.6064 (3)	0.56549 (8)	0.3829 (4)	0.0649 (6)
H2	0.620 (3)	0.5508 (9)	0.262 (4)	0.078 (7)*
C3	0.7094 (2)	0.59375 (7)	0.5099 (3)	0.0575 (5)
C4	0.3945 (3)	0.59055 (10)	0.7556 (4)	0.0838 (7)
H4A	0.417788	0.566096	0.860183	0.126*
H4B	0.294408	0.584567	0.677807	0.126*
H4C	0.399275	0.623576	0.812368	0.126*
C5	0.7116 (3)	0.63718 (9)	0.8440 (3)	0.0633 (5)
H5A	0.650 (3)	0.6299 (9)	0.940 (4)	0.069 (6)*
H5B	0.815 (3)	0.6255 (9)	0.896 (3)	0.073 (7)*
C6	0.7118 (2)	0.69224 (9)	0.7997 (4)	0.0651 (6)
H6A	0.766 (3)	0.7091 (9)	0.907 (4)	0.073 (7)*
H6B	0.751 (3)	0.6996 (9)	0.672 (4)	0.075 (7)*
C7	0.5365 (2)	0.75911 (8)	0.7537 (3)	0.0564 (5)
C8	0.3754 (2)	0.77333 (7)	0.7313 (3)	0.0540 (5)
C9	0.2606 (3)	0.73811 (9)	0.7113 (3)	0.0605 (5)
H9	0.287 (3)	0.7036 (10)	0.710 (4)	0.082 (8)*
C10	0.1132 (3)	0.75312 (10)	0.6989 (4)	0.0725 (6)
H10	0.031 (3)	0.7287 (10)	0.685 (4)	0.092 (8)*
C11	0.0794 (3)	0.80314 (11)	0.7083 (4)	0.0807 (7)
H11	−0.026 (3)	0.8135 (10)	0.702 (4)	0.087 (8)*
C12	0.1916 (4)	0.83847 (11)	0.7265 (4)	0.0856 (8)
H12	0.163 (3)	0.8738 (12)	0.734 (4)	0.101 (9)*
C13	0.3391 (3)	0.82380 (9)	0.7366 (4)	0.0717 (6)
H13	0.421 (3)	0.8472 (11)	0.743 (4)	0.094 (9)*
O1'	0.21422 (19)	0.52552 (7)	0.2699 (3)	0.0859 (6)
H1'	0.317 (4)	0.5368 (13)	0.342 (5)	0.121 (11)*
O2'	0.32943 (17)	0.49184 (7)	0.0484 (3)	0.0836 (5)
C1'	0.2163 (2)	0.50351 (7)	0.1006 (3)	0.0578 (5)
C2'	0.0625 (2)	0.49372 (8)	−0.0245 (4)	0.0629 (5)
H2'	0.055 (3)	0.4785 (11)	−0.152 (5)	0.102 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1359 (19)	0.1154 (17)	0.157 (2)	−0.0397 (14)	0.0970 (17)	−0.0559 (15)
O2	0.0673 (12)	0.1338 (18)	0.1422 (19)	−0.0313 (12)	0.0291 (12)	−0.0469 (15)
O3	0.0542 (8)	0.0556 (8)	0.0704 (9)	−0.0035 (6)	0.0045 (6)	−0.0106 (6)
O4	0.0761 (11)	0.0657 (10)	0.1059 (13)	−0.0188 (8)	0.0246 (9)	−0.0086 (9)
N1	0.0530 (9)	0.0500 (9)	0.0554 (9)	−0.0022 (7)	0.0070 (7)	−0.0012 (7)
N2	0.0587 (11)	0.0481 (9)	0.0776 (12)	−0.0030 (7)	−0.0020 (9)	0.0004 (8)
N3	0.0767 (14)	0.0666 (12)	0.1122 (17)	−0.0152 (10)	0.0416 (13)	−0.0255 (11)
C1	0.0508 (11)	0.0476 (10)	0.0712 (13)	−0.0010 (8)	0.0070 (9)	0.0084 (9)
C2	0.0772 (15)	0.0472 (11)	0.0676 (13)	−0.0024 (10)	0.0094 (11)	−0.0061 (9)
C3	0.0590 (12)	0.0471 (10)	0.0667 (12)	−0.0040 (8)	0.0147 (9)	−0.0041 (9)
C4	0.0685 (15)	0.0803 (16)	0.109 (2)	−0.0047 (12)	0.0329 (14)	0.0080 (14)
C5	0.0616 (13)	0.0701 (14)	0.0529 (11)	0.0021 (10)	0.0008 (10)	−0.0056 (10)
C6	0.0532 (12)	0.0675 (13)	0.0686 (14)	−0.0051 (10)	0.0000 (10)	−0.0185 (11)
C7	0.0679 (13)	0.0558 (11)	0.0450 (10)	−0.0084 (9)	0.0112 (9)	−0.0079 (8)
C8	0.0648 (12)	0.0562 (11)	0.0385 (9)	−0.0020 (9)	0.0058 (8)	−0.0047 (8)
C9	0.0643 (13)	0.0598 (13)	0.0535 (11)	−0.0015 (10)	0.0042 (9)	−0.0051 (9)
C10	0.0626 (14)	0.0813 (16)	0.0685 (14)	−0.0029 (12)	0.0027 (11)	−0.0098 (12)
C11	0.0717 (17)	0.0923 (19)	0.0706 (15)	0.0176 (15)	−0.0017 (12)	−0.0112 (13)
C12	0.092 (2)	0.0672 (16)	0.0907 (18)	0.0186 (14)	0.0038 (14)	−0.0066 (13)
C13	0.0855 (17)	0.0556 (13)	0.0709 (14)	−0.0021 (12)	0.0099 (12)	−0.0047 (10)
O1'	0.0529 (10)	0.0983 (13)	0.1000 (13)	−0.0022 (8)	0.0019 (8)	−0.0331 (10)
O2'	0.0461 (9)	0.1114 (14)	0.0934 (12)	0.0015 (8)	0.0152 (8)	−0.0062 (10)
C1'	0.0497 (11)	0.0496 (11)	0.0720 (13)	−0.0020 (8)	0.0085 (9)	−0.0015 (9)
C2'	0.0479 (11)	0.0601 (12)	0.0785 (14)	−0.0023 (9)	0.0083 (10)	−0.0123 (10)

Geometric parameters (Å, º) top

O1—N3	1.227 (3)	C6—H6A	0.91 (3)
O2—N3	1.221 (3)	C6—H6B	1.03 (3)
O3—C6	1.439 (3)	C7—C8	1.480 (3)
O3—C7	1.343 (2)	C8—C9	1.383 (3)
O4—C7	1.206 (2)	C8—C13	1.386 (3)
N1—C1	1.350 (3)	C9—H9	0.95 (3)
N1—C3	1.384 (3)	C9—C10	1.375 (3)
N1—C5	1.469 (3)	C10—H10	0.98 (3)
N2—C1	1.325 (3)	C10—C11	1.372 (4)
N2—C2	1.346 (3)	C11—H11	0.98 (3)
N3—C3	1.408 (3)	C11—C12	1.369 (4)
C1—C4	1.475 (3)	C12—H12	0.98 (3)
C2—H2	0.95 (2)	C12—C13	1.376 (4)
C2—C3	1.359 (3)	C13—H13	0.96 (3)
C4—H4A	0.9600	O1'—H1'	1.00 (4)
C4—H4B	0.9600	O1'—C1'	1.308 (3)
C4—H4C	0.9600	O2'—C1'	1.195 (2)
C5—H5A	0.97 (2)	C1'—C2'	1.492 (3)
C5—H5B	0.98 (3)	C2'—C2'ⁱ	1.290 (4)
C5—C6	1.498 (3)	C2'—H2'	0.96 (3)

C7—O3—C6	115.97 (16)	C5—C6—H6A	110.0 (15)
C1—N1—C3	105.33 (17)	C5—C6—H6B	112.0 (13)
C1—N1—C5	126.25 (19)	H6A—C6—H6B	112 (2)
C3—N1—C5	128.42 (18)	O3—C7—C8	112.38 (17)
C1—N2—C2	107.32 (18)	O4—C7—O3	122.2 (2)
O1—N3—C3	116.4 (2)	O4—C7—C8	125.4 (2)
O2—N3—O1	123.6 (2)	C9—C8—C7	122.44 (19)
O2—N3—C3	119.9 (2)	C9—C8—C13	118.9 (2)
N1—C1—C4	124.8 (2)	C13—C8—C7	118.6 (2)
N2—C1—N1	111.17 (19)	C8—C9—H9	118.1 (16)
N2—C1—C4	124.0 (2)	C10—C9—C8	120.3 (2)
N2—C2—H2	125.0 (15)	C10—C9—H9	121.5 (16)
N2—C2—C3	108.6 (2)	C9—C10—H10	121.3 (16)
C3—C2—H2	126.4 (15)	C11—C10—C9	120.1 (3)
N1—C3—N3	125.29 (19)	C11—C10—H10	118.5 (16)
C2—C3—N1	107.59 (19)	C10—C11—H11	119.7 (16)
C2—C3—N3	127.1 (2)	C12—C11—C10	120.3 (3)
C1—C4—H4A	109.5	C12—C11—H11	120.0 (16)
C1—C4—H4B	109.5	C11—C12—H12	117.6 (17)
C1—C4—H4C	109.5	C11—C12—C13	120.0 (3)
H4A—C4—H4B	109.5	C13—C12—H12	122.4 (17)
H4A—C4—H4C	109.5	C8—C13—H13	116.6 (17)
H4B—C4—H4C	109.5	C12—C13—C8	120.4 (2)
N1—C5—H5A	105.1 (14)	C12—C13—H13	123.0 (17)
N1—C5—H5B	108.7 (14)	C1'—O1'—H1'	112.7 (19)
N1—C5—C6	112.52 (18)	O1'—C1'—C2'	113.71 (19)
H5A—C5—H5B	109.2 (19)	O2'—C1'—O1'	124.1 (2)
C6—C5—H5A	111.0 (14)	O2'—C1'—C2'	122.2 (2)
C6—C5—H5B	110.2 (14)	C1'—C2'—H2'	118.3 (17)
O3—C6—C5	107.36 (19)	C2'ⁱ—C2'—C1'	124.3 (3)
O3—C6—H6A	108.5 (15)	C2'ⁱ—C2'—H2'	117.3 (17)
O3—C6—H6B	107.2 (14)

Symmetry code: (i) −x, −y+1, −z.

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–malonic acid (2/1) (bzmdmln) top

Crystal data top

2C₁₃H₁₃N₃O₄·C₃H₂O₄	D_x = 1.367 Mg m⁻³
M_r = 652.57	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pbcn	Cell parameters from 9937 reflections
a = 26.1542 (4) Å	θ = 3.1–72.5°
b = 7.2708 (1) Å	µ = 0.92 mm⁻¹
c = 16.6719 (3) Å	T = 300 K
V = 3170.36 (9) Å³	Prism, clear light colourless
Z = 4	0.46 × 0.29 × 0.13 mm
F(000) = 1360

Data collection top

Bruker APEXII CCD diffractometer	2423 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.038
Absorption correction: numerical (SADABS; Bruker, 2016)	θ_max = 68.2°, θ_min = 5.6°
T_min = 0.736, T_max = 0.907	h = −31→31
54755 measured reflections	k = −8→8
2893 independent reflections	l = −20→20

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.078	w = 1/[σ²(F_o²) + (0.1596P)² + 0.3629P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.268	(Δ/σ)_max = 0.001
S = 1.13	Δρ_max = 0.33 e Å⁻³
2893 reflections	Δρ_min = −0.27 e Å⁻³
244 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
36 restraints	Extinction coefficient: 0.0039 (11)
Primary atom site location: dual

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O3	0.29519 (7)	0.6661 (3)	0.53894 (10)	0.1002 (6)
O4	0.21543 (9)	0.6847 (4)	0.58610 (14)	0.1407 (10)
N1	0.39769 (8)	0.5613 (3)	0.58207 (13)	0.0982 (6)
C7	0.24416 (10)	0.6583 (4)	0.53037 (16)	0.0976 (7)
N2	0.44070 (10)	0.3861 (5)	0.49826 (17)	0.1221 (9)
C13	0.26247 (11)	0.5592 (3)	0.39102 (16)	0.0990 (7)
H13	0.297280	0.557512	0.402389	0.119*
N3	0.39562 (11)	0.3512 (5)	0.7007 (2)	0.1341 (10)
C8	0.22811 (9)	0.6113 (3)	0.44877 (16)	0.0912 (7)
O1	0.36955 (13)	0.4498 (6)	0.73879 (15)	0.1791 (15)
C6	0.31291 (13)	0.6898 (5)	0.61932 (18)	0.1201 (10)
H6A	0.304906	0.581714	0.651065	0.144*
H6B	0.296435	0.795389	0.643718	0.144*
C5	0.36982 (14)	0.7184 (5)	0.6162 (2)	0.1214 (10)
H5A	0.377022	0.826914	0.584294	0.146*
H5B	0.382282	0.741023	0.670087	0.146*
C1	0.41726 (10)	0.5501 (5)	0.50779 (16)	0.1076 (9)
C2	0.43619 (11)	0.2967 (5)	0.5682 (2)	0.1165 (9)
H2	0.449468	0.180669	0.579041	0.140*
C12	0.24521 (15)	0.5095 (5)	0.31615 (19)	0.1220 (10)
H12	0.268778	0.474998	0.277171	0.146*
C9	0.17676 (12)	0.6158 (5)	0.4293 (2)	0.1239 (10)
H9	0.152766	0.653022	0.467173	0.149*
O2	0.41029 (16)	0.2059 (6)	0.7247 (3)	0.2129 (19)
C3	0.40976 (10)	0.3995 (4)	0.61981 (18)	0.1060 (8)
C10	0.16136 (17)	0.5646 (7)	0.3534 (3)	0.1490 (15)
H10	0.126798	0.568399	0.340365	0.179*
C11	0.1952 (2)	0.5094 (6)	0.2979 (2)	0.1391 (13)
H11	0.184141	0.471593	0.247515	0.167*
C4	0.41453 (17)	0.6957 (7)	0.4471 (3)	0.1555 (16)
H4A	0.380368	0.743804	0.445026	0.233*
H4B	0.423554	0.646143	0.395651	0.233*
H4C	0.437869	0.792578	0.460914	0.233*
O1'	0.4899 (3)	0.1937 (13)	0.3802 (4)	0.138 (3)	0.5
H1'	0.462376	0.171352	0.401729	0.207*	0.5
C1'	0.4823 (3)	0.2427 (12)	0.3078 (5)	0.106 (2)	0.5
O2'	0.4576 (4)	0.3627 (13)	0.2891 (5)	0.213 (4)	0.5
C2'	0.500000	0.1017 (7)	0.250000	0.1213 (13)
O2"	0.5116 (4)	0.1127 (9)	0.3942 (4)	0.152 (2)	0.5
C1"	0.4925 (3)	0.1738 (11)	0.3373 (6)	0.105 (2)	0.5
O1"	0.4611 (3)	0.3098 (12)	0.3421 (5)	0.185 (3)	0.5
H1"	0.450297	0.317907	0.388154	0.277*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0978 (12)	0.1145 (12)	0.0883 (11)	0.0141 (8)	0.0050 (8)	0.0030 (8)
O4	0.1174 (15)	0.190 (2)	0.1145 (16)	0.0319 (14)	0.0284 (12)	−0.0079 (15)
N1	0.0877 (12)	0.1129 (14)	0.0940 (13)	−0.0032 (10)	−0.0056 (9)	−0.0007 (10)
C7	0.0945 (15)	0.0968 (14)	0.1015 (16)	0.0193 (11)	0.0169 (12)	0.0104 (12)
N2	0.0934 (14)	0.160 (2)	0.1128 (17)	−0.0092 (14)	0.0132 (12)	−0.0241 (16)
C13	0.1102 (17)	0.0899 (14)	0.0968 (16)	−0.0003 (12)	0.0094 (12)	0.0096 (12)
N3	0.1095 (18)	0.169 (3)	0.124 (2)	0.0232 (17)	0.0120 (15)	0.0390 (19)
C8	0.0917 (14)	0.0806 (12)	0.1014 (15)	0.0051 (10)	0.0060 (11)	0.0209 (11)
O1	0.159 (2)	0.275 (4)	0.1037 (16)	0.063 (3)	0.0161 (15)	0.026 (2)
C6	0.120 (2)	0.150 (2)	0.0906 (16)	0.0267 (18)	−0.0044 (14)	−0.0155 (16)
C5	0.130 (2)	0.118 (2)	0.116 (2)	0.0064 (17)	−0.0114 (17)	−0.0212 (16)
C1	0.0871 (14)	0.141 (2)	0.0945 (16)	−0.0176 (14)	−0.0003 (11)	0.0035 (15)
C2	0.0947 (17)	0.124 (2)	0.131 (2)	−0.0053 (14)	0.0115 (16)	−0.0025 (17)
C12	0.151 (3)	0.1107 (19)	0.1046 (19)	−0.0162 (19)	0.0084 (19)	0.0106 (16)
C9	0.0969 (18)	0.140 (2)	0.135 (3)	0.0034 (16)	0.0031 (17)	0.025 (2)
O2	0.197 (3)	0.230 (4)	0.212 (4)	0.064 (3)	0.060 (3)	0.109 (3)
C3	0.0827 (14)	0.1249 (19)	0.1105 (18)	−0.0017 (13)	0.0031 (12)	0.0086 (15)
C10	0.126 (3)	0.165 (3)	0.157 (4)	−0.015 (2)	−0.040 (3)	0.038 (3)
C11	0.171 (3)	0.129 (2)	0.117 (2)	−0.039 (3)	−0.026 (2)	0.034 (2)
C4	0.131 (3)	0.207 (4)	0.128 (3)	−0.021 (3)	0.000 (2)	0.048 (3)
O1'	0.141 (5)	0.174 (6)	0.099 (4)	0.044 (4)	0.001 (3)	0.000 (4)
C1'	0.089 (4)	0.126 (6)	0.104 (4)	0.017 (4)	0.004 (3)	0.013 (4)
O2'	0.302 (10)	0.225 (7)	0.112 (4)	0.145 (7)	0.025 (5)	0.010 (5)
C2'	0.131 (3)	0.133 (3)	0.099 (3)	0.000	−0.001 (2)	0.000
O2"	0.210 (7)	0.134 (4)	0.111 (4)	0.034 (4)	−0.017 (4)	−0.010 (3)
C1"	0.079 (4)	0.099 (5)	0.135 (8)	0.003 (3)	0.015 (5)	0.010 (5)
O1"	0.203 (7)	0.218 (7)	0.134 (5)	0.106 (6)	0.029 (5)	0.018 (5)

Geometric parameters (Å, º) top

O3—C7	1.344 (3)	C8—C9	1.382 (4)
O3—C6	1.428 (4)	C6—C5	1.504 (5)
O4—C7	1.210 (3)	C1—C4	1.466 (5)
N1—C5	1.469 (4)	C2—C3	1.333 (4)
N1—C1	1.343 (4)	C12—C11	1.344 (5)
N1—C3	1.371 (4)	C9—C10	1.380 (6)
C7—C8	1.464 (4)	C10—C11	1.341 (6)
N2—C1	1.350 (4)	O1'—C1'	1.274 (9)
N2—C2	1.340 (4)	C1'—O2'	1.129 (9)
C13—C8	1.370 (4)	C1'—C2'	1.482 (9)
C13—C12	1.376 (4)	C2'—C1"	1.559 (10)
N3—O1	1.176 (4)	C2'—C1"ⁱ	1.559 (10)
N3—O2	1.193 (4)	O2"—C1"	1.161 (11)
N3—C3	1.441 (4)	C1"—O1"	1.288 (9)

C7—O3—C6	115.3 (2)	N2—C1—C4	125.4 (3)
C1—N1—C5	126.4 (3)	C3—C2—N2	109.6 (3)
C1—N1—C3	106.4 (2)	C11—C12—C13	121.7 (3)
C3—N1—C5	127.1 (3)	C10—C9—C8	119.5 (3)
O3—C7—C8	113.2 (2)	N1—C3—N3	125.4 (3)
O4—C7—O3	121.9 (3)	C2—C3—N1	107.7 (3)
O4—C7—C8	124.9 (3)	C2—C3—N3	126.9 (3)
C2—N2—C1	106.6 (3)	C11—C10—C9	121.4 (4)
C8—C13—C12	119.7 (3)	C10—C11—C12	119.1 (4)
O1—N3—O2	122.9 (4)	O1'—C1'—C2'	112.0 (7)
O1—N3—C3	120.4 (3)	O2'—C1'—O1'	124.5 (8)
O2—N3—C3	116.6 (4)	O2'—C1'—C2'	122.3 (7)
C13—C8—C7	122.0 (2)	C1'ⁱ—C2'—C1'	92.4 (7)
C13—C8—C9	118.6 (3)	C1'ⁱ—C2'—C1"ⁱ	28.4 (3)
C9—C8—C7	119.4 (3)	C1'—C2'—C1"ⁱ	114.4 (6)
O3—C6—C5	107.8 (3)	C1"ⁱ—C2'—C1"	140.7 (7)
N1—C5—C6	113.4 (3)	O2"—C1"—C2'	125.5 (7)
N1—C1—N2	109.6 (3)	O2"—C1"—O1"	121.1 (10)
N1—C1—C4	125.0 (3)	O1"—C1"—C2'	113.4 (8)

Symmetry code: (i) −x+1, y, −z+1/2.

1-[2-(Benzoyloxy)ethyl]-2-methyl-5-nitro-1H-imidazol-3-ium 2,6-dihydroxybenzoate (bzmd26dba) top

Crystal data top

C₁₃H₁₄N₃O₄⁺·C₇H₅O₄⁻	F(000) = 896
M_r = 429.38	D_x = 1.442 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.2443 (4) Å	Cell parameters from 9886 reflections
b = 15.9009 (7) Å	θ = 2.5–27.5°
c = 15.4526 (8) Å	µ = 0.11 mm⁻¹
β = 102.454 (2)°	T = 301 K
V = 1978.04 (17) Å³	Prism, clear light yellow
Z = 4	0.83 × 0.67 × 0.27 mm

Data collection top

Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer	3408 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.076
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 27.5°, θ_min = 2.8°
T_min = 0.490, T_max = 0.746	h = −10→10
27674 measured reflections	k = −20→20
4348 independent reflections	l = −20→19

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.069	All H-atom parameters refined
wR(F²) = 0.185	w = 1/[σ²(F_o²) + (0.0913P)² + 0.5735P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
4348 reflections	Δρ_max = 0.37 e Å⁻³
356 parameters	Δρ_min = −0.27 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O3	0.30908 (16)	0.45737 (9)	0.10470 (8)	0.0471 (3)
O1'	0.69550 (19)	0.38992 (10)	0.49968 (10)	0.0592 (4)
N1	0.25612 (18)	0.49805 (10)	0.28713 (10)	0.0407 (4)
O2	−0.08963 (19)	0.47761 (14)	0.24372 (12)	0.0777 (6)
O4'	1.0124 (2)	0.38277 (12)	0.56331 (14)	0.0725 (5)
O2'	0.5209 (2)	0.32169 (12)	0.56404 (14)	0.0728 (5)
N2	0.4226 (2)	0.44392 (10)	0.40318 (11)	0.0478 (4)
N3	−0.0133 (2)	0.44450 (12)	0.31200 (12)	0.0545 (5)
O1	−0.0783 (2)	0.40294 (14)	0.36109 (14)	0.0832 (6)
O4	0.1499 (2)	0.39405 (13)	−0.01207 (12)	0.0778 (6)
O3'	0.6249 (3)	0.22744 (13)	0.69473 (15)	0.0855 (6)
C1'	0.8096 (3)	0.30675 (11)	0.62457 (12)	0.0455 (4)
C1	0.4158 (2)	0.48952 (12)	0.33097 (13)	0.0441 (4)
C7'	0.6658 (3)	0.33991 (13)	0.55944 (13)	0.0485 (5)
C8	0.4427 (2)	0.37835 (12)	0.01068 (13)	0.0448 (4)
C6	0.1575 (2)	0.48994 (15)	0.12428 (14)	0.0494 (5)
C3	0.1624 (2)	0.45427 (12)	0.33634 (12)	0.0435 (4)
C2	0.2662 (3)	0.42133 (13)	0.40789 (13)	0.0487 (5)
C5	0.2007 (3)	0.54528 (13)	0.20416 (14)	0.0479 (5)
C2'	0.9742 (3)	0.32956 (13)	0.62356 (14)	0.0531 (5)
C7	0.2864 (2)	0.40967 (13)	0.03172 (13)	0.0484 (5)
C13	0.4327 (3)	0.33220 (15)	−0.06576 (17)	0.0618 (6)
C9	0.5971 (3)	0.39351 (15)	0.06467 (16)	0.0563 (5)
C3'	1.1037 (4)	0.29727 (17)	0.6877 (2)	0.0774 (8)
C4	0.5618 (3)	0.5256 (2)	0.3029 (2)	0.0649 (6)
C10	0.7374 (3)	0.36102 (18)	0.04179 (19)	0.0694 (7)
C12	0.5745 (4)	0.30044 (16)	−0.08794 (19)	0.0693 (7)
C6'	0.7806 (4)	0.25214 (13)	0.69090 (15)	0.0616 (6)
C11	0.7265 (3)	0.31502 (16)	−0.03340 (19)	0.0669 (6)
C4'	1.0704 (5)	0.24431 (17)	0.7517 (2)	0.0892 (11)
C5'	0.9118 (5)	0.22182 (16)	0.75427 (19)	0.0829 (9)
H5A	0.292 (3)	0.5844 (13)	0.2002 (14)	0.048 (5)*
H6A	0.086 (3)	0.4400 (15)	0.1351 (16)	0.058 (6)*
H2	0.238 (3)	0.3877 (14)	0.4495 (17)	0.058 (7)*
H5B	0.109 (3)	0.5774 (15)	0.2123 (15)	0.057 (6)*
H6B	0.099 (3)	0.5229 (15)	0.0737 (18)	0.065 (7)*
H12	0.564 (4)	0.2705 (17)	−0.142 (2)	0.081 (8)*
H9	0.599 (3)	0.4257 (16)	0.1141 (18)	0.063 (7)*
H3'	1.210 (4)	0.3103 (19)	0.676 (2)	0.088 (9)*
H11	0.823 (4)	0.2909 (16)	−0.0509 (18)	0.074 (8)*
H4'A	1.152 (4)	0.2196 (19)	0.798 (2)	0.095 (10)*
H4'	0.898 (5)	0.399 (2)	0.523 (2)	0.116 (12)*
H10	0.843 (4)	0.370 (2)	0.082 (2)	0.100 (10)*
H13	0.330 (4)	0.3231 (18)	−0.103 (2)	0.086 (9)*
H5'	0.879 (4)	0.187 (2)	0.801 (2)	0.102 (10)*
H2'	0.562 (5)	0.270 (3)	0.638 (3)	0.133 (14)*
H1'	0.548 (6)	0.415 (2)	0.454 (3)	0.132 (13)*
H4A	0.575 (5)	0.504 (2)	0.250 (3)	0.117 (13)*
H4B	0.554 (6)	0.585 (3)	0.303 (3)	0.133 (15)*
H4C	0.653 (6)	0.515 (3)	0.347 (3)	0.138 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0316 (7)	0.0630 (8)	0.0445 (7)	0.0046 (6)	0.0037 (5)	−0.0008 (6)
O1'	0.0422 (8)	0.0778 (10)	0.0546 (8)	0.0077 (7)	0.0037 (6)	0.0114 (7)
N1	0.0297 (8)	0.0472 (8)	0.0446 (8)	0.0045 (6)	0.0068 (6)	−0.0010 (6)
O2	0.0341 (8)	0.1341 (16)	0.0631 (10)	0.0079 (9)	0.0061 (7)	0.0170 (10)
O4'	0.0427 (9)	0.0877 (12)	0.0845 (12)	−0.0045 (8)	0.0080 (8)	0.0172 (9)
O2'	0.0443 (9)	0.0815 (11)	0.0917 (13)	−0.0026 (8)	0.0130 (8)	0.0032 (10)
N2	0.0387 (9)	0.0542 (9)	0.0468 (9)	0.0072 (7)	0.0006 (7)	−0.0072 (7)
N3	0.0333 (9)	0.0752 (12)	0.0560 (10)	0.0015 (8)	0.0114 (7)	0.0005 (8)
O1	0.0479 (10)	0.1147 (15)	0.0903 (13)	−0.0120 (10)	0.0222 (9)	0.0255 (11)
O4	0.0375 (9)	0.1101 (14)	0.0769 (11)	0.0044 (8)	−0.0073 (8)	−0.0305 (10)
O3'	0.0927 (16)	0.0810 (12)	0.0888 (14)	−0.0202 (11)	0.0326 (12)	0.0109 (11)
C1'	0.0491 (11)	0.0408 (9)	0.0442 (9)	0.0021 (8)	0.0048 (8)	−0.0074 (7)
C1	0.0318 (9)	0.0482 (10)	0.0511 (10)	0.0044 (7)	0.0061 (7)	−0.0099 (8)
C7'	0.0411 (11)	0.0518 (10)	0.0517 (11)	0.0025 (8)	0.0078 (8)	−0.0100 (8)
C8	0.0391 (10)	0.0469 (9)	0.0474 (10)	0.0003 (8)	0.0071 (8)	0.0036 (8)
C6	0.0315 (10)	0.0673 (13)	0.0481 (10)	0.0081 (9)	0.0057 (8)	0.0033 (9)
C3	0.0339 (10)	0.0502 (10)	0.0461 (9)	0.0032 (7)	0.0076 (7)	−0.0035 (8)
C2	0.0459 (11)	0.0546 (11)	0.0445 (10)	0.0032 (9)	0.0075 (8)	−0.0003 (8)
C5	0.0411 (11)	0.0499 (10)	0.0532 (11)	0.0095 (9)	0.0110 (8)	0.0076 (8)
C2'	0.0481 (12)	0.0484 (10)	0.0569 (11)	0.0023 (8)	−0.0017 (9)	−0.0042 (9)
C7	0.0371 (10)	0.0581 (11)	0.0472 (10)	0.0012 (8)	0.0026 (8)	0.0017 (8)
C13	0.0543 (14)	0.0662 (14)	0.0628 (13)	−0.0018 (11)	0.0084 (11)	−0.0111 (11)
C9	0.0408 (11)	0.0693 (13)	0.0559 (12)	0.0008 (9)	0.0040 (9)	−0.0047 (10)
C3'	0.0580 (16)	0.0624 (14)	0.0941 (19)	0.0003 (12)	−0.0227 (14)	−0.0016 (13)
C4	0.0343 (12)	0.0828 (18)	0.0783 (17)	−0.0058 (11)	0.0140 (11)	−0.0068 (14)
C10	0.0387 (13)	0.0857 (17)	0.0824 (17)	0.0056 (11)	0.0097 (11)	−0.0019 (14)
C12	0.0786 (18)	0.0628 (14)	0.0718 (15)	0.0038 (12)	0.0281 (13)	−0.0111 (12)
C6'	0.0806 (17)	0.0450 (10)	0.0571 (12)	−0.0043 (10)	0.0104 (11)	−0.0039 (9)
C11	0.0559 (15)	0.0649 (14)	0.0858 (17)	0.0122 (11)	0.0286 (13)	0.0062 (12)
C4'	0.106 (3)	0.0537 (14)	0.0816 (18)	0.0071 (14)	−0.0370 (17)	0.0058 (13)
C5'	0.117 (3)	0.0514 (13)	0.0667 (15)	−0.0072 (14)	−0.0101 (16)	0.0113 (12)

Geometric parameters (Å, º) top

O3—C6	1.444 (2)	C6—C5	1.495 (3)
O3—C7	1.338 (2)	C6—H6A	1.02 (2)
O1'—C7'	1.282 (3)	C6—H6B	0.98 (3)
O1'—H1'	1.32 (5)	C3—C2	1.350 (3)
N1—C1	1.351 (2)	C2—H2	0.90 (2)
N1—C3	1.383 (2)	C5—H5A	0.99 (2)
N1—C5	1.471 (2)	C5—H5B	0.95 (2)
O2—N3	1.225 (2)	C2'—C3'	1.389 (3)
O4'—C2'	1.345 (3)	C13—C12	1.383 (4)
O4'—H4'	1.05 (4)	C13—H13	0.93 (3)
O2'—C7'	1.246 (3)	C9—C10	1.381 (3)
O2'—H2'	1.38 (5)	C9—H9	0.92 (3)
N2—C1	1.322 (3)	C3'—C4'	1.371 (5)
N2—C2	1.355 (3)	C3'—H3'	0.96 (3)
N2—H1'	1.25 (5)	C4—H4A	0.92 (4)
N3—O1	1.214 (2)	C4—H4B	0.95 (4)
N3—C3	1.424 (3)	C4—H4C	0.92 (5)
O4—C7	1.207 (3)	C10—C11	1.359 (4)
O3'—C6'	1.356 (3)	C10—H10	0.97 (4)
O3'—H2'	1.15 (5)	C12—C11	1.370 (4)
C1'—C7'	1.477 (3)	C12—H12	0.94 (3)
C1'—C2'	1.408 (3)	C6'—C5'	1.380 (4)
C1'—C6'	1.402 (3)	C11—H11	0.97 (3)
C1—C4	1.480 (3)	C4'—C5'	1.365 (5)
C8—C7	1.481 (3)	C4'—H4'A	0.96 (4)
C8—C13	1.378 (3)	C5'—H5'	1.00 (3)
C8—C9	1.385 (3)

C7—O3—C6	114.21 (15)	C6—C5—H5B	111.8 (15)
C7'—O1'—H1'	105.9 (17)	H5A—C5—H5B	108.1 (19)
C1—N1—C3	105.86 (15)	O4'—C2'—C1'	122.70 (19)
C1—N1—C5	125.05 (17)	O4'—C2'—C3'	117.9 (2)
C3—N1—C5	129.09 (16)	C3'—C2'—C1'	119.4 (2)
C2'—O4'—H4'	104.8 (19)	O3—C7—C8	113.92 (17)
C7'—O2'—H2'	96.7 (17)	O4—C7—O3	122.18 (19)
C1—N2—C2	108.84 (17)	O4—C7—C8	123.90 (19)
C1—N2—H1'	127.8 (19)	C8—C13—C12	120.6 (2)
C2—N2—H1'	122.7 (18)	C8—C13—H13	119.3 (19)
O2—N3—C3	119.01 (18)	C12—C13—H13	120.0 (19)
O1—N3—O2	123.94 (19)	C8—C9—H9	116.6 (17)
O1—N3—C3	117.05 (18)	C10—C9—C8	119.5 (2)
C6'—O3'—H2'	94 (2)	C10—C9—H9	123.9 (17)
C2'—C1'—C7'	122.29 (19)	C2'—C3'—H3'	112 (2)
C6'—C1'—C7'	118.7 (2)	C4'—C3'—C2'	119.9 (3)
C6'—C1'—C2'	118.9 (2)	C4'—C3'—H3'	127.4 (19)
N1—C1—C4	125.5 (2)	C1—C4—H4A	112 (2)
N2—C1—N1	109.75 (17)	C1—C4—H4B	109 (3)
N2—C1—C4	124.8 (2)	C1—C4—H4C	107 (3)
O1'—C7'—C1'	117.54 (18)	H4A—C4—H4B	113 (4)
O2'—C7'—O1'	121.3 (2)	H4A—C4—H4C	111 (4)
O2'—C7'—C1'	121.1 (2)	H4B—C4—H4C	104 (4)
C13—C8—C7	118.26 (19)	C9—C10—H10	118 (2)
C13—C8—C9	119.1 (2)	C11—C10—C9	121.0 (2)
C9—C8—C7	122.66 (19)	C11—C10—H10	121 (2)
O3—C6—C5	108.75 (16)	C13—C12—H12	118.5 (19)
O3—C6—H6A	108.1 (13)	C11—C12—C13	119.7 (2)
O3—C6—H6B	108.8 (15)	C11—C12—H12	121.8 (19)
C5—C6—H6A	111.4 (13)	O3'—C6'—C1'	121.5 (2)
C5—C6—H6B	109.4 (14)	O3'—C6'—C5'	118.2 (3)
H6A—C6—H6B	110 (2)	C5'—C6'—C1'	120.3 (3)
N1—C3—N3	124.52 (17)	C10—C11—C12	120.0 (2)
C2—C3—N1	108.34 (17)	C10—C11—H11	122.8 (17)
C2—C3—N3	127.11 (19)	C12—C11—H11	117.2 (17)
N2—C2—H2	125.8 (17)	C3'—C4'—H4'A	126 (2)
C3—C2—N2	107.21 (19)	C5'—C4'—C3'	121.6 (3)
C3—C2—H2	126.8 (17)	C5'—C4'—H4'A	113 (2)
N1—C5—C6	113.14 (17)	C6'—C5'—H5'	115 (2)
N1—C5—H5A	106.2 (13)	C4'—C5'—C6'	119.8 (3)
N1—C5—H5B	105.5 (14)	C4'—C5'—H5'	126 (2)
C6—C5—H5A	111.6 (13)

2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–3,5-dihydroxybenzoic acid (3/1) (bzmd35dba) top

Crystal data top

3C₁₃H₁₃N₃O₄·C₇H₆O₄	F(000) = 2048
M_r = 979.91	D_x = 1.394 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 7.1481 (2) Å	Cell parameters from 9896 reflections
b = 36.7892 (8) Å	θ = 3.5–67.6°
c = 18.0584 (4) Å	µ = 0.91 mm⁻¹
β = 100.451 (1)°	T = 300 K
V = 4670.1 (2) Å³	Prism, clear light colourless
Z = 4	0.28 × 0.14 × 0.06 mm

Data collection top

Bruker APEXII CCD diffractometer	5499 reflections with I > 2σ(I)
Multilayer mirrors monochromator	R_int = 0.058
φ and ω scans	θ_max = 68.7°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −7→8
T_min = 0.835, T_max = 0.986	k = −44→44
56516 measured reflections	l = −21→21
8547 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.052	w = 1/[σ²(F_o²) + (0.0833P)² + 2.1514P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.176	(Δ/σ)_max = 0.002
S = 1.01	Δρ_max = 0.27 e Å⁻³
8547 reflections	Δρ_min = −0.21 e Å⁻³
844 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.00125 (13)
Primary atom site location: dual

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1C	0.8254 (4)	0.36199 (7)	−0.06761 (14)	0.0939 (7)
O2C	0.5826 (4)	0.32866 (7)	−0.11345 (12)	0.0874 (7)
O3C	0.3392 (3)	0.26359 (5)	0.03750 (10)	0.0688 (5)
O3A	0.7853 (3)	0.47087 (5)	0.86671 (10)	0.0634 (5)
N1A	0.9537 (3)	0.51097 (6)	0.74799 (11)	0.0540 (5)
O3B	0.7069 (3)	0.71873 (5)	0.49400 (11)	0.0704 (5)
O3'	0.5229 (3)	0.56376 (5)	0.34945 (12)	0.0766 (6)
O4'	0.8266 (3)	0.46389 (5)	0.49620 (11)	0.0721 (6)
O4C	0.2932 (4)	0.20905 (6)	−0.01637 (14)	0.0909 (7)
N1C	0.4294 (3)	0.33992 (6)	0.01710 (12)	0.0571 (5)
N2C	0.5611 (4)	0.37320 (7)	0.11443 (14)	0.0772 (7)
N3C	0.6713 (4)	0.34779 (7)	−0.06396 (14)	0.0668 (6)
C1C	0.4139 (5)	0.35240 (8)	0.08614 (16)	0.0697 (8)
C2C	0.6752 (5)	0.37470 (8)	0.06255 (18)	0.0705 (8)
H2C	0.785 (5)	0.3879 (9)	0.0685 (17)	0.074 (9)*
C3C	0.5974 (4)	0.35420 (7)	0.00232 (15)	0.0578 (6)
C4C	0.2524 (9)	0.34396 (14)	0.1246 (3)	0.1032 (14)
H4CA	0.207 (7)	0.3175 (15)	0.123 (3)	0.154 (19)*
H4CB	0.284 (7)	0.3513 (15)	0.170 (3)	0.15 (2)*
H4CC	0.140 (10)	0.3572 (18)	0.104 (3)	0.19 (3)*
C5C	0.2834 (4)	0.31870 (8)	−0.03207 (18)	0.0639 (7)
H5CA	0.260 (4)	0.3289 (8)	−0.0824 (17)	0.069 (8)*
H5CB	0.161 (5)	0.3213 (8)	−0.0124 (16)	0.075 (9)*
C6C	0.3292 (5)	0.27923 (8)	−0.03625 (16)	0.0651 (7)
H6CA	0.454 (5)	0.2757 (9)	−0.0532 (18)	0.085 (10)*
H6CB	0.231 (4)	0.2679 (8)	−0.0697 (16)	0.063 (8)*
C7C	0.3174 (4)	0.22757 (8)	0.03984 (18)	0.0659 (7)
C14C	0.332 (6)	0.2182 (8)	0.1204 (10)	0.068 (6)	0.5318
C15C	0.390 (4)	0.2413 (5)	0.1819 (15)	0.068 (3)	0.5318
H15C	0.419867	0.265318	0.173166	0.082*	0.5318
C16C	0.403 (2)	0.2292 (5)	0.2561 (9)	0.093 (4)	0.5318
H16C	0.434781	0.245824	0.295117	0.112*	0.5318
C17C	0.370 (2)	0.1927 (6)	0.2740 (8)	0.112 (5)	0.5318
H17C	0.385648	0.184515	0.323553	0.135*	0.5318
C18C	0.310 (2)	0.1691 (4)	0.2119 (7)	0.101 (6)	0.5318
H18C	0.277796	0.145168	0.220181	0.121*	0.5318
C19C	0.300 (3)	0.1817 (6)	0.1385 (13)	0.088 (4)	0.5318
H19C	0.270497	0.165123	0.099208	0.105*	0.5318
C8C	0.322 (6)	0.2090 (9)	0.1134 (10)	0.062 (6)	0.4682
C13C	0.364 (4)	0.2293 (6)	0.176 (2)	0.081 (6)	0.4682
H13C	0.392618	0.253879	0.173808	0.097*	0.4682
C12C	0.362 (3)	0.2123 (5)	0.2448 (12)	0.099 (6)	0.4682
H12C	0.390847	0.225357	0.289514	0.119*	0.4682
C11C	0.317 (3)	0.1770 (6)	0.2460 (7)	0.094 (5)	0.4682
H11C	0.317949	0.165177	0.291564	0.113*	0.4682
C10C	0.269 (3)	0.1580 (6)	0.1779 (9)	0.109 (6)	0.4682
H10C	0.238908	0.133490	0.179162	0.130*	0.4682
C9C	0.266 (4)	0.1735 (6)	0.1132 (13)	0.081 (5)	0.4682
H9C	0.226439	0.160916	0.068431	0.097*	0.4682
O1A	0.8622 (4)	0.60568 (6)	0.72428 (15)	0.1031 (8)
O2A	0.9845 (4)	0.57753 (6)	0.82685 (13)	0.0913 (7)
O4A	0.7325 (4)	0.47827 (10)	0.98395 (13)	0.1178 (10)
N2A	0.8422 (3)	0.50522 (6)	0.62493 (12)	0.0589 (5)
N3A	0.9160 (4)	0.57788 (7)	0.75940 (15)	0.0722 (7)
C1A	0.9167 (4)	0.48799 (7)	0.68826 (14)	0.0548 (6)
C2A	0.8300 (4)	0.54068 (8)	0.64394 (16)	0.0613 (7)
H2A	0.782 (4)	0.5591 (8)	0.6103 (18)	0.076 (9)*
C3A	0.8979 (4)	0.54472 (7)	0.71862 (15)	0.0574 (6)
C4A	0.9548 (6)	0.44854 (9)	0.6922 (2)	0.0726 (8)
H4AA	1.089 (6)	0.4430 (11)	0.708 (2)	0.112 (14)*
H4AB	0.892 (5)	0.4370 (10)	0.731 (2)	0.106 (12)*
H4AC	0.902 (6)	0.4365 (11)	0.648 (3)	0.122 (14)*
C5A	1.0501 (4)	0.50018 (10)	0.82398 (15)	0.0628 (7)
H5AA	1.146 (4)	0.5180 (8)	0.8411 (16)	0.073 (9)*
H5AB	1.104 (5)	0.4746 (10)	0.8180 (18)	0.085 (10)*
C6A	0.9251 (5)	0.49971 (10)	0.88285 (16)	0.0666 (7)
H6AA	1.011 (4)	0.4945 (8)	0.9322 (18)	0.078 (9)*
H6AB	0.859 (5)	0.5241 (10)	0.8861 (18)	0.091 (11)*
C7A	0.6892 (4)	0.46458 (9)	0.92272 (16)	0.0726 (8)
C8A	0.5226 (4)	0.44060 (9)	0.90204 (17)	0.0701 (8)
C9A	0.4877 (5)	0.42069 (9)	0.8363 (2)	0.0777 (9)
H9A	0.580 (4)	0.4208 (8)	0.8021 (17)	0.072 (9)*
C10A	0.3229 (6)	0.39958 (10)	0.8191 (3)	0.0967 (13)
H10A	0.307 (6)	0.3863 (11)	0.770 (2)	0.117 (14)*
C11A	0.1962 (6)	0.39897 (12)	0.8675 (3)	0.1073 (15)
H11A	0.073 (7)	0.3852 (12)	0.856 (3)	0.135 (16)*
C12A	0.2295 (6)	0.41829 (12)	0.9333 (3)	0.1003 (13)
H12A	0.134 (6)	0.4175 (11)	0.969 (2)	0.115 (13)*
C13A	0.3934 (5)	0.43885 (11)	0.9514 (2)	0.0867 (10)
H13A	0.422 (6)	0.4556 (11)	0.993 (2)	0.107 (14)*
O1B	0.2377 (4)	0.64048 (6)	0.62852 (13)	0.0840 (6)
O2B	0.4848 (4)	0.67270 (7)	0.67579 (13)	0.0956 (8)
O4B	0.6319 (4)	0.77703 (6)	0.50557 (12)	0.0850 (7)
N1B	0.6714 (3)	0.64843 (6)	0.56085 (12)	0.0595 (5)
N2B	0.5676 (4)	0.60475 (6)	0.47891 (13)	0.0670 (6)
N3B	0.4023 (4)	0.65101 (7)	0.62963 (14)	0.0713 (7)
C1B	0.7086 (4)	0.62802 (7)	0.50247 (16)	0.0645 (7)
C2B	0.4352 (5)	0.61020 (8)	0.52319 (17)	0.0656 (7)
H2B	0.320 (4)	0.5970 (8)	0.5189 (16)	0.066 (8)*
C3B	0.4962 (4)	0.63698 (7)	0.57283 (15)	0.0596 (7)
C4B	0.8810 (5)	0.63092 (11)	0.4683 (2)	0.0961 (11)
H4BA	0.890475	0.655102	0.449353	0.144*
H4BB	0.873150	0.613816	0.427700	0.144*
H4BC	0.991440	0.625719	0.505677	0.144*
C5B	0.7922 (5)	0.67798 (8)	0.5974 (2)	0.0694 (8)
H5BA	0.807 (5)	0.6749 (9)	0.652 (2)	0.087 (10)*
H5BB	0.912 (5)	0.6750 (8)	0.5815 (16)	0.072 (9)*
C6B	0.7111 (5)	0.71471 (8)	0.57400 (17)	0.0683 (8)
H6BA	0.786 (4)	0.7336 (8)	0.6008 (16)	0.063 (8)*
H6BB	0.574 (5)	0.7165 (8)	0.5825 (17)	0.078 (9)*
C7B	0.6616 (4)	0.75204 (8)	0.46585 (16)	0.0633 (7)
C8B	0.6546 (4)	0.75459 (8)	0.38362 (16)	0.0656 (7)
C9B	0.6406 (5)	0.72461 (11)	0.3370 (2)	0.0789 (9)
H9B	0.642 (4)	0.7020 (8)	0.3596 (16)	0.065 (9)*
C10B	0.6313 (6)	0.72971 (15)	0.2597 (2)	0.0979 (12)
H10B	0.631 (5)	0.7072 (11)	0.233 (2)	0.111 (13)*
C11B	0.6431 (6)	0.76410 (15)	0.2314 (2)	0.1012 (12)
H11B	0.643 (6)	0.7687 (12)	0.175 (3)	0.139 (16)*
C12B	0.6565 (6)	0.79407 (14)	0.2768 (2)	0.0951 (11)
H12B	0.670 (7)	0.8222 (16)	0.256 (3)	0.17 (2)*
C13B	0.6609 (5)	0.78897 (11)	0.3529 (2)	0.0802 (9)
H13B	0.664 (5)	0.8100 (9)	0.3852 (19)	0.082 (10)*
O1'	0.6210 (4)	0.41366 (6)	0.24229 (12)	0.0924 (8)
H1'	0.593 (6)	0.4002 (12)	0.194 (3)	0.130 (15)*
O2'	0.4848 (4)	0.45805 (6)	0.17062 (11)	0.0929 (8)
H3'	0.540 (5)	0.5769 (11)	0.397 (2)	0.111 (13)*
H4'	0.829 (6)	0.4799 (11)	0.538 (2)	0.118 (13)*
C1'	0.6075 (3)	0.47064 (6)	0.29968 (12)	0.0478 (5)
C2'	0.5473 (4)	0.50641 (7)	0.29381 (14)	0.0538 (6)
H2'	0.485 (4)	0.5175 (8)	0.2465 (16)	0.066 (8)*
C3'	0.5826 (4)	0.52839 (7)	0.35727 (14)	0.0547 (6)
C4'	0.6741 (4)	0.51454 (7)	0.42558 (14)	0.0547 (6)
H4'A	0.695 (4)	0.5297 (8)	0.4690 (16)	0.066 (8)*
C5'	0.7340 (4)	0.47867 (7)	0.43047 (13)	0.0538 (6)
C6'	0.7015 (4)	0.45642 (7)	0.36715 (14)	0.0525 (6)
H6'	0.745 (4)	0.4308 (7)	0.3716 (14)	0.056 (7)*
C7'	0.5633 (4)	0.44730 (7)	0.23118 (14)	0.0547 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1C	0.0824 (16)	0.1000 (17)	0.1057 (18)	−0.0177 (14)	0.0339 (14)	0.0013 (13)
O2C	0.0938 (16)	0.1079 (17)	0.0617 (12)	−0.0126 (14)	0.0174 (12)	−0.0190 (12)
O3C	0.0881 (14)	0.0579 (11)	0.0581 (11)	−0.0031 (10)	0.0070 (10)	−0.0047 (8)
O3A	0.0616 (11)	0.0758 (12)	0.0500 (10)	−0.0110 (9)	0.0026 (8)	0.0045 (8)
N1A	0.0514 (12)	0.0630 (12)	0.0460 (11)	−0.0034 (10)	0.0046 (9)	0.0001 (9)
O3B	0.0864 (14)	0.0615 (11)	0.0644 (12)	−0.0020 (10)	0.0164 (10)	−0.0104 (9)
O3'	0.1090 (17)	0.0550 (11)	0.0595 (12)	0.0166 (11)	−0.0012 (11)	−0.0068 (9)
O4'	0.0980 (16)	0.0601 (11)	0.0497 (11)	0.0065 (10)	−0.0089 (10)	−0.0005 (9)
O4C	0.116 (2)	0.0611 (12)	0.0930 (16)	−0.0062 (12)	0.0128 (14)	−0.0160 (11)
N1C	0.0628 (14)	0.0536 (12)	0.0546 (12)	0.0006 (10)	0.0095 (10)	−0.0075 (9)
N2C	0.104 (2)	0.0613 (14)	0.0633 (15)	0.0020 (14)	0.0076 (15)	−0.0174 (11)
N3C	0.0673 (16)	0.0680 (14)	0.0659 (15)	−0.0002 (12)	0.0147 (12)	0.0021 (12)
C1C	0.090 (2)	0.0590 (16)	0.0627 (17)	0.0081 (16)	0.0208 (16)	−0.0108 (13)
C2C	0.080 (2)	0.0572 (16)	0.0690 (19)	−0.0039 (16)	0.0005 (16)	−0.0073 (13)
C3C	0.0616 (16)	0.0537 (14)	0.0570 (15)	−0.0024 (12)	0.0075 (12)	−0.0062 (11)
C4C	0.121 (4)	0.102 (3)	0.103 (3)	0.003 (3)	0.062 (3)	−0.019 (3)
C5C	0.0621 (18)	0.0632 (16)	0.0633 (17)	−0.0010 (14)	0.0028 (14)	−0.0020 (13)
C6C	0.077 (2)	0.0599 (16)	0.0555 (16)	−0.0066 (15)	0.0039 (15)	−0.0061 (12)
C7C	0.0581 (17)	0.0605 (16)	0.0777 (19)	0.0021 (13)	0.0089 (14)	0.0006 (14)
C14C	0.056 (6)	0.054 (13)	0.098 (10)	0.007 (8)	0.024 (7)	0.010 (8)
C15C	0.065 (7)	0.081 (9)	0.059 (5)	−0.005 (7)	0.013 (5)	0.002 (7)
C16C	0.074 (6)	0.136 (13)	0.072 (8)	−0.007 (7)	0.021 (5)	0.011 (7)
C17C	0.083 (8)	0.183 (16)	0.073 (10)	0.020 (8)	0.019 (7)	0.038 (9)
C18C	0.126 (9)	0.123 (15)	0.063 (13)	0.014 (9)	0.043 (12)	0.038 (11)
C19C	0.084 (7)	0.068 (10)	0.114 (14)	0.003 (6)	0.027 (8)	0.007 (8)
C8C	0.066 (8)	0.054 (15)	0.067 (6)	0.011 (10)	0.017 (5)	0.005 (6)
C13C	0.070 (9)	0.087 (13)	0.086 (10)	−0.007 (9)	0.015 (8)	0.011 (13)
C12C	0.094 (12)	0.14 (2)	0.063 (8)	0.015 (11)	0.010 (7)	−0.002 (10)
C11C	0.093 (9)	0.155 (15)	0.036 (10)	0.032 (8)	0.021 (8)	0.029 (10)
C10C	0.150 (14)	0.101 (10)	0.088 (13)	0.036 (9)	0.056 (11)	0.020 (8)
C9C	0.100 (12)	0.058 (9)	0.095 (11)	0.005 (7)	0.044 (10)	0.007 (6)
O1A	0.137 (2)	0.0657 (14)	0.1079 (19)	0.0135 (14)	0.0244 (17)	−0.0030 (13)
O2A	0.1095 (19)	0.0871 (15)	0.0741 (15)	−0.0183 (13)	0.0079 (13)	−0.0214 (11)
O4A	0.1005 (19)	0.196 (3)	0.0587 (14)	−0.052 (2)	0.0189 (13)	−0.0193 (16)
N2A	0.0597 (13)	0.0659 (13)	0.0497 (12)	−0.0009 (11)	0.0058 (10)	0.0008 (10)
N3A	0.0755 (17)	0.0693 (16)	0.0738 (17)	−0.0062 (13)	0.0188 (14)	−0.0087 (13)
C1A	0.0532 (15)	0.0615 (15)	0.0478 (13)	−0.0055 (12)	0.0042 (11)	−0.0006 (11)
C2A	0.0597 (17)	0.0686 (17)	0.0553 (15)	0.0032 (14)	0.0094 (13)	0.0067 (13)
C3A	0.0550 (15)	0.0584 (15)	0.0587 (15)	−0.0015 (12)	0.0102 (12)	−0.0027 (12)
C4A	0.083 (2)	0.0656 (18)	0.0656 (19)	−0.0013 (17)	0.0029 (18)	−0.0013 (15)
C5A	0.0545 (16)	0.082 (2)	0.0474 (14)	−0.0103 (16)	−0.0024 (12)	0.0011 (13)
C6A	0.0629 (18)	0.084 (2)	0.0497 (15)	−0.0158 (16)	0.0029 (13)	−0.0046 (13)
C7A	0.0642 (18)	0.099 (2)	0.0526 (16)	−0.0075 (16)	0.0065 (14)	0.0075 (15)
C8A	0.0601 (17)	0.0775 (19)	0.0684 (18)	−0.0014 (15)	0.0002 (14)	0.0213 (15)
C9A	0.075 (2)	0.0714 (19)	0.080 (2)	−0.0069 (17)	−0.0042 (18)	0.0225 (16)
C10A	0.096 (3)	0.073 (2)	0.106 (3)	−0.017 (2)	−0.022 (2)	0.025 (2)
C11A	0.075 (3)	0.091 (3)	0.147 (4)	−0.015 (2)	−0.004 (3)	0.054 (3)
C12A	0.070 (2)	0.098 (3)	0.132 (4)	0.000 (2)	0.016 (3)	0.048 (3)
C13A	0.072 (2)	0.089 (2)	0.100 (3)	0.0007 (19)	0.018 (2)	0.030 (2)
O1B	0.0854 (16)	0.0831 (14)	0.0907 (16)	0.0068 (12)	0.0346 (13)	0.0075 (11)
O2B	0.119 (2)	0.0971 (17)	0.0754 (14)	−0.0060 (15)	0.0307 (14)	−0.0279 (13)
O4B	0.1183 (19)	0.0642 (12)	0.0757 (13)	0.0054 (12)	0.0259 (13)	−0.0099 (10)
N1B	0.0624 (14)	0.0547 (12)	0.0617 (13)	0.0001 (10)	0.0124 (11)	−0.0074 (10)
N2B	0.0788 (16)	0.0565 (13)	0.0677 (14)	0.0021 (12)	0.0185 (12)	−0.0091 (11)
N3B	0.0839 (19)	0.0675 (15)	0.0669 (15)	0.0051 (14)	0.0255 (13)	0.0013 (12)
C1B	0.0701 (18)	0.0575 (15)	0.0682 (17)	0.0022 (14)	0.0184 (14)	−0.0096 (13)
C2B	0.073 (2)	0.0566 (15)	0.0691 (18)	0.0000 (15)	0.0184 (15)	−0.0025 (13)
C3B	0.0700 (18)	0.0549 (14)	0.0556 (15)	0.0033 (13)	0.0160 (13)	−0.0023 (11)
C4B	0.082 (2)	0.108 (3)	0.107 (3)	−0.003 (2)	0.040 (2)	−0.027 (2)
C5B	0.071 (2)	0.0659 (17)	0.068 (2)	−0.0021 (15)	0.0047 (16)	−0.0121 (14)
C6B	0.082 (2)	0.0601 (16)	0.0617 (17)	−0.0084 (16)	0.0107 (15)	−0.0123 (13)
C7B	0.0599 (17)	0.0608 (16)	0.0692 (17)	−0.0066 (13)	0.0118 (14)	−0.0101 (13)
C8B	0.0540 (16)	0.0779 (19)	0.0640 (17)	−0.0071 (14)	0.0081 (13)	−0.0126 (14)
C9B	0.070 (2)	0.087 (2)	0.079 (2)	−0.0118 (18)	0.0120 (16)	−0.0207 (18)
C10B	0.083 (3)	0.130 (4)	0.079 (2)	−0.007 (2)	0.0084 (19)	−0.038 (3)
C11B	0.085 (3)	0.147 (4)	0.071 (2)	0.002 (3)	0.011 (2)	0.002 (3)
C12B	0.092 (3)	0.120 (3)	0.073 (2)	0.000 (2)	0.0145 (19)	0.010 (2)
C13B	0.079 (2)	0.085 (2)	0.076 (2)	−0.0051 (18)	0.0126 (17)	−0.0013 (18)
O1'	0.151 (2)	0.0591 (12)	0.0587 (12)	0.0135 (13)	−0.0021 (13)	−0.0159 (10)
O2'	0.130 (2)	0.0837 (15)	0.0529 (12)	0.0226 (14)	−0.0171 (12)	−0.0174 (10)
C1'	0.0488 (13)	0.0526 (13)	0.0419 (12)	−0.0064 (11)	0.0078 (10)	−0.0060 (10)
C2'	0.0589 (16)	0.0548 (14)	0.0457 (13)	−0.0004 (12)	0.0038 (11)	−0.0022 (11)
C3'	0.0602 (16)	0.0490 (13)	0.0540 (14)	0.0010 (12)	0.0083 (12)	−0.0047 (11)
C4'	0.0638 (16)	0.0545 (14)	0.0430 (13)	−0.0027 (12)	0.0020 (12)	−0.0084 (11)
C5'	0.0581 (15)	0.0565 (14)	0.0441 (13)	−0.0025 (12)	0.0023 (11)	−0.0014 (10)
C6'	0.0576 (15)	0.0489 (14)	0.0498 (13)	−0.0013 (12)	0.0067 (11)	−0.0038 (10)
C7'	0.0569 (15)	0.0583 (15)	0.0486 (14)	−0.0037 (12)	0.0084 (12)	−0.0073 (11)

Geometric parameters (Å, º) top

O1C—N3C	1.232 (3)	C4A—H4AA	0.97 (4)
O2C—N3C	1.221 (3)	C4A—H4AB	1.00 (4)
O3C—C6C	1.440 (3)	C4A—H4AC	0.94 (5)
O3C—C7C	1.336 (3)	C5A—H5AA	0.96 (3)
O3A—C6A	1.450 (3)	C5A—H5AB	1.03 (3)
O3A—C7A	1.342 (3)	C5A—C6A	1.508 (4)
N1A—C1A	1.358 (3)	C6A—H6AA	1.00 (3)
N1A—C3A	1.380 (3)	C6A—H6AB	1.02 (4)
N1A—C5A	1.474 (3)	C7A—C8A	1.475 (4)
O3B—C6B	1.447 (3)	C8A—C9A	1.379 (5)
O3B—C7B	1.344 (3)	C8A—C13A	1.396 (5)
O3'—H3'	0.97 (4)	C9A—H9A	0.98 (3)
O3'—C3'	1.369 (3)	C9A—C10A	1.398 (5)
O4'—H4'	0.96 (4)	C10A—H10A	0.99 (4)
O4'—C5'	1.363 (3)	C10A—C11A	1.368 (7)
O4C—C7C	1.209 (4)	C11A—H11A	1.00 (5)
N1C—C1C	1.352 (3)	C11A—C12A	1.368 (7)
N1C—C3C	1.381 (3)	C12A—H12A	1.03 (4)
N1C—C5C	1.466 (3)	C12A—C13A	1.382 (6)
N2C—C1C	1.326 (4)	C13A—H13A	0.96 (4)
N2C—C2C	1.350 (4)	O1B—N3B	1.235 (3)
N3C—C3C	1.413 (3)	O2B—N3B	1.225 (3)
C1C—C4C	1.484 (5)	O4B—C7B	1.208 (3)
C2C—H2C	0.92 (3)	N1B—C1B	1.359 (3)
C2C—C3C	1.357 (4)	N1B—C3B	1.375 (3)
C4C—H4CA	1.02 (5)	N1B—C5B	1.468 (4)
C4C—H4CB	0.85 (6)	N2B—C1B	1.332 (4)
C4C—H4CC	0.95 (7)	N2B—C2B	1.360 (4)
C5C—H5CA	0.97 (3)	N3B—C3B	1.421 (3)
C5C—H5CB	1.01 (3)	C1B—C4B	1.479 (4)
C5C—C6C	1.493 (4)	C2B—H2B	0.95 (3)
C6C—H6CA	1.00 (3)	C2B—C3B	1.350 (4)
C6C—H6CB	0.94 (3)	C4B—H4BA	0.9600
C7C—C14C	1.480 (13)	C4B—H4BB	0.9600
C7C—C8C	1.489 (12)	C4B—H4BC	0.9600
C14C—C15C	1.40 (3)	C5B—H5BA	0.98 (3)
C14C—C19C	1.41 (3)	C5B—H5BB	0.96 (3)
C15C—H15C	0.9300	C5B—C6B	1.500 (4)
C15C—C16C	1.40 (3)	C6B—H6BA	0.95 (3)
C16C—H16C	0.9300	C6B—H6BB	1.02 (3)
C16C—C17C	1.41 (3)	C7B—C8B	1.480 (4)
C17C—H17C	0.9300	C8B—C9B	1.380 (4)
C17C—C18C	1.42 (2)	C8B—C13B	1.386 (5)
C18C—H18C	0.9300	C9B—H9B	0.93 (3)
C18C—C19C	1.39 (3)	C9B—C10B	1.399 (5)
C19C—H19C	0.9300	C10B—H10B	0.96 (4)
C8C—C13C	1.35 (4)	C10B—C11B	1.372 (6)
C8C—C9C	1.37 (4)	C11B—H11B	1.04 (5)
C13C—H13C	0.9300	C11B—C12B	1.367 (6)
C13C—C12C	1.39 (4)	C12B—H12B	1.11 (6)
C12C—H12C	0.9300	C12B—C13B	1.381 (5)
C12C—C11C	1.34 (3)	C13B—H13B	0.97 (3)
C11C—H11C	0.9300	O1'—H1'	0.99 (5)
C11C—C10C	1.402 (19)	O1'—C7'	1.308 (3)
C10C—H10C	0.9300	O2'—C7'	1.202 (3)
C10C—C9C	1.29 (4)	C1'—C2'	1.383 (3)
C9C—H9C	0.9300	C1'—C6'	1.383 (3)
O1A—N3A	1.228 (3)	C1'—C7'	1.492 (3)
O2A—N3A	1.228 (3)	C2'—H2'	0.98 (3)
O4A—C7A	1.203 (4)	C2'—C3'	1.388 (3)
N2A—C1A	1.331 (3)	C3'—C4'	1.384 (3)
N2A—C2A	1.356 (4)	C4'—H4'A	0.95 (3)
N3A—C3A	1.419 (4)	C4'—C5'	1.385 (4)
C1A—C4A	1.476 (4)	C5'—C6'	1.391 (3)
C2A—H2A	0.93 (3)	C6'—H6'	0.99 (3)
C2A—C3A	1.356 (4)

C7C—O3C—C6C	116.0 (2)	C6A—C5A—H5AA	105.1 (18)
C7A—O3A—C6A	113.8 (2)	C6A—C5A—H5AB	110.2 (18)
C1A—N1A—C3A	104.7 (2)	O3A—C6A—C5A	110.0 (2)
C1A—N1A—C5A	124.2 (2)	O3A—C6A—H6AA	108.9 (17)
C3A—N1A—C5A	130.8 (2)	O3A—C6A—H6AB	110 (2)
C7B—O3B—C6B	115.5 (2)	C5A—C6A—H6AA	106.5 (18)
C3'—O3'—H3'	113 (2)	C5A—C6A—H6AB	111.7 (19)
C5'—O4'—H4'	112 (2)	H6AA—C6A—H6AB	109 (3)
C1C—N1C—C3C	105.6 (2)	O3A—C7A—C8A	114.4 (3)
C1C—N1C—C5C	124.8 (3)	O4A—C7A—O3A	122.6 (3)
C3C—N1C—C5C	129.3 (2)	O4A—C7A—C8A	123.0 (3)
C1C—N2C—C2C	107.1 (2)	C9A—C8A—C7A	123.2 (3)
O1C—N3C—C3C	116.7 (3)	C9A—C8A—C13A	119.2 (3)
O2C—N3C—O1C	123.8 (3)	C13A—C8A—C7A	117.6 (3)
O2C—N3C—C3C	119.5 (2)	C8A—C9A—H9A	120.2 (19)
N1C—C1C—C4C	124.1 (3)	C8A—C9A—C10A	119.9 (4)
N2C—C1C—N1C	111.1 (3)	C10A—C9A—H9A	119.9 (19)
N2C—C1C—C4C	124.8 (3)	C9A—C10A—H10A	115 (3)
N2C—C2C—H2C	124 (2)	C11A—C10A—C9A	119.8 (5)
N2C—C2C—C3C	108.8 (3)	C11A—C10A—H10A	125 (3)
C3C—C2C—H2C	128 (2)	C10A—C11A—H11A	122 (3)
N1C—C3C—N3C	124.9 (2)	C10A—C11A—C12A	121.0 (4)
C2C—C3C—N1C	107.5 (3)	C12A—C11A—H11A	117 (3)
C2C—C3C—N3C	127.6 (3)	C11A—C12A—H12A	120 (2)
C1C—C4C—H4CA	117 (3)	C11A—C12A—C13A	119.7 (5)
C1C—C4C—H4CB	107 (4)	C13A—C12A—H12A	120 (2)
C1C—C4C—H4CC	113 (4)	C8A—C13A—H13A	113 (3)
H4CA—C4C—H4CB	110 (5)	C12A—C13A—C8A	120.3 (5)
H4CA—C4C—H4CC	104 (5)	C12A—C13A—H13A	126 (3)
H4CB—C4C—H4CC	105 (5)	C1B—N1B—C3B	105.3 (2)
N1C—C5C—H5CA	110.2 (17)	C1B—N1B—C5B	125.1 (3)
N1C—C5C—H5CB	107.7 (17)	C3B—N1B—C5B	129.4 (2)
N1C—C5C—C6C	114.2 (3)	C1B—N2B—C2B	106.5 (2)
H5CA—C5C—H5CB	106 (2)	O1B—N3B—C3B	116.6 (3)
C6C—C5C—H5CA	109.3 (17)	O2B—N3B—O1B	123.7 (3)
C6C—C5C—H5CB	108.8 (17)	O2B—N3B—C3B	119.7 (3)
O3C—C6C—C5C	108.4 (2)	N1B—C1B—C4B	125.4 (3)
O3C—C6C—H6CA	109.5 (19)	N2B—C1B—N1B	111.1 (2)
O3C—C6C—H6CB	108.9 (17)	N2B—C1B—C4B	123.6 (3)
C5C—C6C—H6CA	110.9 (19)	N2B—C2B—H2B	124.3 (17)
C5C—C6C—H6CB	108.6 (17)	C3B—C2B—N2B	108.8 (3)
H6CA—C6C—H6CB	110 (2)	C3B—C2B—H2B	126.8 (17)
O3C—C7C—C14C	105.9 (12)	N1B—C3B—N3B	124.4 (2)
O3C—C7C—C8C	120.0 (13)	C2B—C3B—N1B	108.2 (2)
O4C—C7C—O3C	122.2 (3)	C2B—C3B—N3B	127.3 (3)
O4C—C7C—C14C	131.9 (12)	C1B—C4B—H4BA	109.5
O4C—C7C—C8C	117.9 (13)	C1B—C4B—H4BB	109.5
C15C—C14C—C7C	127 (2)	C1B—C4B—H4BC	109.5
C15C—C14C—C19C	115.6 (14)	H4BA—C4B—H4BB	109.5
C19C—C14C—C7C	118 (2)	H4BA—C4B—H4BC	109.5
C14C—C15C—H15C	119.2	H4BB—C4B—H4BC	109.5
C14C—C15C—C16C	121.7 (15)	N1B—C5B—H5BA	108 (2)
C16C—C15C—H15C	119.2	N1B—C5B—H5BB	105.4 (18)
C15C—C16C—H16C	118.7	N1B—C5B—C6B	112.0 (3)
C17C—C16C—C15C	122.5 (13)	H5BA—C5B—H5BB	111 (3)
C17C—C16C—H16C	118.7	C6B—C5B—H5BA	111 (2)
C16C—C17C—H17C	122.0	C6B—C5B—H5BB	109.9 (18)
C16C—C17C—C18C	115.9 (14)	O3B—C6B—C5B	108.0 (2)
C18C—C17C—H17C	122.0	O3B—C6B—H6BA	110.0 (17)
C17C—C18C—H18C	119.8	O3B—C6B—H6BB	107.2 (18)
C19C—C18C—C17C	120.4 (15)	C5B—C6B—H6BA	111.2 (17)
C19C—C18C—H18C	119.8	C5B—C6B—H6BB	110.5 (17)
C14C—C19C—H19C	118.2	H6BA—C6B—H6BB	110 (2)
C18C—C19C—C14C	123.6 (15)	O3B—C7B—C8B	113.5 (2)
C18C—C19C—H19C	118.2	O4B—C7B—O3B	121.7 (3)
C13C—C8C—C7C	118 (3)	O4B—C7B—C8B	124.7 (3)
C9C—C8C—C7C	119 (2)	C9B—C8B—C7B	123.1 (3)
C9C—C8C—C13C	123.6 (17)	C9B—C8B—C13B	119.3 (3)
C8C—C13C—H13C	121.2	C13B—C8B—C7B	117.6 (3)
C12C—C13C—C8C	117.7 (19)	C8B—C9B—H9B	117.2 (19)
C12C—C13C—H13C	121.2	C8B—C9B—C10B	119.1 (4)
C13C—C12C—H12C	120.3	C10B—C9B—H9B	123.6 (19)
C11C—C12C—C13C	119.5 (17)	C9B—C10B—H10B	112 (2)
C11C—C12C—H12C	120.3	C11B—C10B—C9B	120.0 (4)
C12C—C11C—H11C	120.3	C11B—C10B—H10B	127 (2)
C12C—C11C—C10C	119 (2)	C10B—C11B—H11B	122 (3)
C10C—C11C—H11C	120.3	C12B—C11B—C10B	121.5 (4)
C11C—C10C—H10C	118.8	C12B—C11B—H11B	117 (3)
C9C—C10C—C11C	122 (2)	C11B—C12B—H12B	124 (3)
C9C—C10C—H10C	118.8	C11B—C12B—C13B	118.2 (4)
C8C—C9C—H9C	121.3	C13B—C12B—H12B	118 (3)
C10C—C9C—C8C	117.4 (16)	C8B—C13B—H13B	119 (2)
C10C—C9C—H9C	121.3	C12B—C13B—C8B	121.8 (4)
C1A—N2A—C2A	105.9 (2)	C12B—C13B—H13B	119 (2)
O1A—N3A—C3A	117.2 (3)	C7'—O1'—H1'	109 (2)
O2A—N3A—O1A	123.5 (3)	C2'—C1'—C6'	121.5 (2)
O2A—N3A—C3A	119.2 (3)	C2'—C1'—C7'	117.9 (2)
N1A—C1A—C4A	124.5 (2)	C6'—C1'—C7'	120.6 (2)
N2A—C1A—N1A	112.1 (2)	C1'—C2'—H2'	123.3 (16)
N2A—C1A—C4A	123.5 (2)	C1'—C2'—C3'	118.9 (2)
N2A—C2A—H2A	124.5 (19)	C3'—C2'—H2'	117.7 (16)
N2A—C2A—C3A	109.2 (3)	O3'—C3'—C2'	117.5 (2)
C3A—C2A—H2A	126.3 (19)	O3'—C3'—C4'	122.0 (2)
N1A—C3A—N3A	125.6 (2)	C4'—C3'—C2'	120.5 (2)
C2A—C3A—N1A	108.0 (2)	C3'—C4'—H4'A	119.7 (17)
C2A—C3A—N3A	126.4 (3)	C3'—C4'—C5'	119.9 (2)
C1A—C4A—H4AA	113 (2)	C5'—C4'—H4'A	120.4 (17)
C1A—C4A—H4AB	110 (2)	O4'—C5'—C4'	122.1 (2)
C1A—C4A—H4AC	112 (3)	O4'—C5'—C6'	117.6 (2)
H4AA—C4A—H4AB	104 (3)	C4'—C5'—C6'	120.3 (2)
H4AA—C4A—H4AC	112 (3)	C1'—C6'—C5'	118.9 (2)
H4AB—C4A—H4AC	104 (3)	C1'—C6'—H6'	121.7 (15)
N1A—C5A—H5AA	107.6 (18)	C5'—C6'—H6'	119.3 (15)
N1A—C5A—H5AB	105.7 (18)	O1'—C7'—C1'	113.8 (2)
N1A—C5A—C6A	115.0 (3)	O2'—C7'—O1'	122.2 (2)
H5AA—C5A—H5AB	114 (3)	O2'—C7'—C1'	124.0 (2)

Selected dihedral angles (°) of the BZMD molecule in single and multicomponent solid forms. The θ column lists the angles between the planes defined by the imidazole (BZMD) and phenyl/carboxylic (coformer) groups top

		φ₁	φ₂	φ₃	φ₄	φ₅	θ
1	BZMD	104.1	-63.9	-94.9	178.6	-10.6	–
2	BZMDH	100.9	-66.4	-178.4	179.5	-6.3	–
3	SLC	111.0	-70.2	-170.8	177.4	7.3	3.8
4	3,5DBA	110.3	-67.7	-169.5	-168.7	-11.8	5.7
5	RES	106.6	-59.8	-174.0	-171.8	6.5	30.3
6	NAF	105.6	-68.8	170.5	178.3	9.0	6.9
7	3,5DBA	105.4	-63.4	-159.1	179.4	7.4/10.9	83.7
8	RES	105.1	-71.5	-169.1	175.6	3.7	31.6
9	3,5DBA	104.0	-63.6	-171.5	-178.6	17.8	89.9
10	ABN	103.6	-62.5	178.6	-179.1	-3.1	13.2
11	FMA	103.3	-70.5	-169.6	175.9	3.8	22.6
12	MLN	102.9	-61.5	-173.2	-172.9	7.5	22.8/29.3
13	2,6DBA	102.4	-73.5	-177.2	178.4	3.4	5.5
14	3,5DNZ	99.8	-65.5	-173.9	-178.0	20.2	75.4
15	IAC	99.8	-65.9	-168.4	177.1	4.4	20.4
16	MAC	94.5	-171.0	81.6	171.2	-10.4	5.1
17	BZC	-82.9	-63.0	159.2	-178.2	-11.0	17.5
18	MLC	-72.7	-66.7	98.1	170.2	-14.7	59.9

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