A new two-dimensional ZnII coordination polymer based on 1,3-bis­(2-methyl-1H-imidazol-1-yl)benzene and 5-nitro­benzene-1,3-di­carb­oxy­lic acid: synthesis, crystal structure and physical properties

Chen, N.-N.; Ni, J.-N.; Wang, J.; Tao, J.-Q.

doi:10.1107/S2053229619000986

A new two-dimensional Zn^II coordination polymer based on 1,3-bis(2-methyl-1H-imidazol-1-yl)benzene and 5-nitrobenzene-1,3-dicarboxylic acid: synthesis, crystal structure and physical properties

N.-N. Chen, J.-N. Ni, J. Wang and J.-Q. Tao

A novel two-dimensional (2D) Zn^II coordination framework, poly[[μ-1,3-bis(2-methyl-1H-imidazol-1-yl)benzene](μ-5-nitrobenzene-1,3-dicarboxylato)zinc(II)], [Zn(C₈H₃NO₆)(C₁₄H₁₄N₄)]_n or [Zn(NO₂-BDC)(1,3-BMIB)]_n [1,3-BMIB is 1,3-bis(2-methyl-1H-imidazol-1-yl)benzene and NO₂-H₂BDC is 5-nitrobenzene-1,3-dicarboxylic acid], has been prepared and characterized by IR, elemental analysis, thermal analysis and single-crystal X-ray diffraction. Single-crystal X-ray diffraction analysis revealed that the compound is a new 2D polymer with a 6³ topology parallel to the (10 $\overline{2}$ ) crystal planes based on left-handed helices, right-handed helical NO₂-BDC–Zn chains and [Zn₂(1,3-BMIB)₂]_n clusters. In the crystal, adjacent layers are further connected by C—H

O hydrogen bonds, C—H

π interactions, C—O

π interactions and N—O

π interactions to form a three-dimensional structure in the solid state. In addition, the compound exhibits strong fluorescence emissions in the solid state at room temperature.

Keywords: two-dimensional coordination polymer; zinc(II); 1,3-bis(2-methyl-1H-imidazol-1-yl)benzene; 5-nitrobenzene-1,3-dicarboxylic acid; photoluminescence; crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619000986/qs3078sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229619000986/qs3078Isup2.hkl Contains datablock I

CCDC reference: 1892014

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: publCIF (Westrip, 2010).

Poly[[µ-1,3-bis(2-methyl-1H-imidazol-1-yl)benzene](µ-5-nitrobenzene-1,3-dicarboxylato)zinc(II)] top

Crystal data top

[Zn(C₈H₃NO₆)(C₁₄H₁₄N₄)]	F(000) = 1048
M_r = 512.80	D_x = 1.533 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.568 (6) Å	Cell parameters from 9121 reflections
b = 13.324 (7) Å	θ = 2.7–27.6°
c = 14.207 (7) Å	µ = 1.16 mm⁻¹
β = 110.912 (5)°	T = 296 K
V = 2222.3 (19) Å³	Block, colorless
Z = 4	0.21 × 0.19 × 0.17 mm

Data collection top

Bruker SMART CCD area detector diffractometer	4022 reflections with I > 2σ(I)
Radiation source: x-ray tube	R_int = 0.019
phi and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
T_min = 0.785, T_max = 0.822	k = −16→16
22595 measured reflections	l = −17→17
4359 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H-atom parameters constrained
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.0402P)² + 1.0538P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
4359 reflections	Δρ_max = 0.77 e Å⁻³
309 parameters	Δρ_min = −0.25 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
C22	1.13159 (19)	−0.11355 (16)	0.7143 (2)	0.0572 (6)
H22A	1.2090	−0.1085	0.7175	0.086*
H22B	1.1292	−0.1060	0.7807	0.086*
H22C	1.0868	−0.0617	0.6713	0.086*
C21	1.08495 (15)	−0.21308 (12)	0.67325 (14)	0.0346 (4)
N4	1.14047 (12)	−0.28589 (10)	0.64756 (12)	0.0354 (3)
C20	1.06470 (17)	−0.36404 (15)	0.6134 (2)	0.0540 (6)
H20	1.0811	−0.4254	0.5904	0.065*
C19	0.96355 (19)	−0.33822 (16)	0.6184 (2)	0.0613 (7)
H19	0.8979	−0.3772	0.5996	0.074*
N3	0.97671 (13)	−0.24200 (12)	0.65710 (14)	0.0404 (4)
C17	0.89046 (15)	−0.17656 (13)	0.66832 (15)	0.0383 (4)
C16	0.87098 (18)	−0.17327 (15)	0.75749 (16)	0.0466 (5)
H16	0.9100	−0.2160	0.8103	0.056*
C15	0.79188 (19)	−0.10500 (16)	0.76769 (16)	0.0495 (5)
H15	0.7768	−0.1033	0.8272	0.059*
Zn1	0.69472 (2)	0.27715 (2)	0.34318 (2)	0.02960 (8)
O1	0.63764 (11)	0.40797 (9)	0.36525 (10)	0.0387 (3)
O2	0.76641 (15)	0.39284 (13)	0.51902 (12)	0.0633 (5)
O3	0.39155 (12)	0.70809 (9)	0.28248 (9)	0.0397 (3)
O4	0.42046 (13)	0.83278 (9)	0.39240 (11)	0.0471 (3)
O6	0.74405 (17)	0.61513 (14)	0.78460 (11)	0.0703 (5)
O5	0.61084 (16)	0.72622 (13)	0.75137 (12)	0.0616 (4)
N1	0.67650 (12)	0.15549 (11)	0.42241 (11)	0.0334 (3)
N2	0.70400 (13)	0.02398 (11)	0.52039 (11)	0.0360 (3)
N5	0.66318 (15)	0.66121 (13)	0.72578 (12)	0.0442 (4)
C1	0.68582 (15)	0.43617 (13)	0.45671 (14)	0.0355 (4)
C18	0.83326 (16)	−0.11390 (14)	0.58925 (15)	0.0388 (4)
H18	0.8454	−0.1182	0.5285	0.047*
C2	0.43737 (14)	0.74757 (13)	0.36904 (12)	0.0297 (3)
C5	0.51988 (13)	0.67903 (12)	0.44649 (12)	0.0284 (3)
C3	0.63867 (14)	0.53008 (12)	0.48752 (13)	0.0299 (3)
C4	0.56069 (14)	0.59160 (12)	0.41710 (12)	0.0292 (3)
H4	0.5353	0.5742	0.3493	0.035*
C8	0.67298 (14)	0.55369 (13)	0.58900 (13)	0.0324 (3)
H8	0.7243	0.5129	0.6372	0.039*
C6	0.55464 (15)	0.70326 (12)	0.54799 (13)	0.0318 (3)
H6	0.5284	0.7612	0.5691	0.038*
C11	0.74495 (15)	0.11483 (13)	0.50702 (14)	0.0353 (4)
C13	0.75728 (15)	−0.04436 (13)	0.60172 (14)	0.0359 (4)
C9	0.58795 (15)	0.08804 (14)	0.38118 (14)	0.0378 (4)
H9	0.5269	0.0978	0.3212	0.045*
C10	0.60323 (16)	0.00658 (14)	0.44041 (14)	0.0396 (4)
H10	0.5563	−0.0494	0.4300	0.047*
C14	0.73531 (17)	−0.03944 (14)	0.68993 (15)	0.0426 (4)
H14	0.6835	0.0070	0.6973	0.051*
C7	0.62931 (14)	0.63912 (13)	0.61724 (12)	0.0325 (3)
C12	0.85115 (18)	0.16005 (16)	0.57886 (17)	0.0535 (5)
H12A	0.9161	0.1284	0.5709	0.080*
H12B	0.8537	0.1503	0.6466	0.080*
H12C	0.8522	0.2306	0.5655	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C22	0.0445 (11)	0.0418 (11)	0.0854 (17)	−0.0048 (9)	0.0233 (11)	−0.0264 (11)
C21	0.0314 (9)	0.0307 (8)	0.0412 (9)	0.0021 (7)	0.0124 (7)	−0.0016 (7)
N4	0.0298 (7)	0.0294 (7)	0.0467 (9)	0.0011 (6)	0.0133 (6)	−0.0050 (6)
C20	0.0398 (10)	0.0302 (9)	0.0921 (17)	−0.0024 (8)	0.0237 (11)	−0.0163 (10)
C19	0.0385 (11)	0.0332 (10)	0.114 (2)	−0.0060 (8)	0.0288 (12)	−0.0119 (11)
N3	0.0312 (8)	0.0298 (7)	0.0618 (10)	0.0046 (6)	0.0184 (7)	0.0020 (7)
C17	0.0311 (9)	0.0309 (9)	0.0559 (11)	0.0052 (7)	0.0191 (8)	0.0049 (8)
C16	0.0467 (11)	0.0423 (10)	0.0508 (11)	0.0085 (8)	0.0173 (9)	0.0137 (9)
C15	0.0589 (12)	0.0517 (12)	0.0466 (11)	0.0100 (10)	0.0296 (10)	0.0080 (9)
Zn1	0.02918 (12)	0.02538 (11)	0.03324 (12)	0.00164 (7)	0.00989 (8)	−0.00228 (7)
O1	0.0460 (7)	0.0300 (6)	0.0417 (7)	0.0074 (5)	0.0175 (6)	−0.0040 (5)
O2	0.0710 (10)	0.0612 (10)	0.0491 (8)	0.0392 (8)	0.0110 (8)	−0.0005 (7)
O3	0.0449 (7)	0.0341 (6)	0.0337 (7)	0.0067 (5)	0.0063 (6)	0.0020 (5)
O4	0.0597 (9)	0.0300 (6)	0.0475 (8)	0.0134 (6)	0.0143 (7)	−0.0002 (6)
O6	0.0894 (13)	0.0677 (11)	0.0355 (8)	0.0249 (10)	0.0000 (8)	−0.0005 (7)
O5	0.0766 (11)	0.0679 (11)	0.0426 (8)	0.0131 (8)	0.0240 (8)	−0.0136 (7)
N1	0.0344 (7)	0.0315 (7)	0.0337 (7)	0.0001 (6)	0.0113 (6)	0.0014 (6)
N2	0.0353 (8)	0.0308 (7)	0.0419 (8)	0.0045 (6)	0.0136 (6)	0.0030 (6)
N5	0.0541 (10)	0.0433 (9)	0.0332 (8)	0.0005 (8)	0.0132 (7)	−0.0043 (7)
C1	0.0395 (9)	0.0306 (8)	0.0409 (10)	0.0073 (7)	0.0196 (8)	0.0030 (7)
C18	0.0399 (9)	0.0354 (9)	0.0459 (10)	0.0055 (8)	0.0211 (8)	0.0037 (8)
C2	0.0289 (8)	0.0282 (8)	0.0336 (8)	0.0013 (6)	0.0130 (7)	0.0024 (7)
C5	0.0272 (8)	0.0255 (7)	0.0340 (8)	0.0004 (6)	0.0126 (7)	0.0005 (6)
C3	0.0296 (8)	0.0272 (8)	0.0351 (8)	0.0023 (6)	0.0141 (7)	0.0004 (6)
C4	0.0318 (8)	0.0278 (8)	0.0292 (8)	0.0010 (6)	0.0122 (6)	−0.0009 (6)
C8	0.0312 (8)	0.0315 (8)	0.0335 (9)	0.0045 (7)	0.0102 (7)	0.0035 (7)
C6	0.0341 (9)	0.0268 (8)	0.0364 (9)	0.0019 (7)	0.0147 (7)	−0.0035 (7)
C11	0.0341 (9)	0.0312 (8)	0.0395 (9)	0.0033 (7)	0.0120 (7)	0.0009 (7)
C13	0.0352 (9)	0.0299 (8)	0.0427 (10)	0.0051 (7)	0.0140 (7)	0.0046 (7)
C9	0.0355 (9)	0.0407 (10)	0.0345 (9)	−0.0032 (7)	0.0093 (7)	−0.0013 (7)
C10	0.0379 (9)	0.0355 (9)	0.0452 (10)	−0.0039 (7)	0.0146 (8)	−0.0028 (8)
C14	0.0429 (10)	0.0383 (10)	0.0519 (11)	0.0096 (8)	0.0235 (9)	0.0026 (8)
C7	0.0353 (9)	0.0331 (8)	0.0296 (8)	−0.0024 (7)	0.0121 (7)	−0.0031 (7)
C12	0.0476 (12)	0.0448 (11)	0.0528 (12)	−0.0063 (9)	−0.0007 (9)	0.0068 (9)

Geometric parameters (Å, º) top

C22—C21	1.483 (3)	O5—N5	1.219 (2)
C22—H22A	0.9600	N1—C11	1.319 (2)
C22—H22B	0.9600	N1—C9	1.387 (2)
C22—H22C	0.9600	N2—C11	1.355 (2)
C21—N4	1.320 (2)	N2—C10	1.386 (2)
C21—N3	1.352 (2)	N2—C13	1.435 (2)
N4—C20	1.377 (2)	N5—C7	1.476 (2)
N4—Zn1ⁱ	2.0315 (18)	C1—C3	1.514 (2)
C20—C19	1.343 (3)	C18—C13	1.387 (2)
C20—H20	0.9300	C18—H18	0.9300
C19—N3	1.381 (3)	C2—C5	1.518 (2)
C19—H19	0.9300	C5—C6	1.387 (2)
N3—C17	1.444 (2)	C5—C4	1.395 (2)
C17—C16	1.374 (3)	C3—C8	1.385 (2)
C17—C18	1.378 (3)	C3—C4	1.390 (2)
C16—C15	1.393 (3)	C4—H4	0.9300
C16—H16	0.9300	C8—C7	1.384 (2)
C15—C14	1.389 (3)	C8—H8	0.9300
C15—H15	0.9300	C6—C7	1.386 (2)
Zn1—O1	1.9524 (14)	C6—H6	0.9300
Zn1—O3ⁱⁱ	1.9563 (14)	C11—C12	1.488 (3)
Zn1—N4ⁱ	2.0315 (18)	C13—C14	1.378 (3)
Zn1—N1	2.0326 (16)	C9—C10	1.344 (3)
O1—C1	1.279 (2)	C9—H9	0.9300
O2—C1	1.226 (2)	C10—H10	0.9300
O3—C2	1.271 (2)	C14—H14	0.9300
O3—Zn1ⁱⁱⁱ	1.9563 (14)	C12—H12A	0.9600
O4—C2	1.223 (2)	C12—H12B	0.9600
O6—N5	1.226 (2)	C12—H12C	0.9600

C21—C22—H22A	109.5	O2—C1—C3	119.22 (17)
C21—C22—H22B	109.5	O1—C1—C3	116.38 (15)
H22A—C22—H22B	109.5	C17—C18—C13	118.91 (17)
C21—C22—H22C	109.5	C17—C18—H18	120.5
H22A—C22—H22C	109.5	C13—C18—H18	120.5
H22B—C22—H22C	109.5	O4—C2—O3	125.76 (16)
N4—C21—N3	110.04 (15)	O4—C2—C5	120.11 (15)
N4—C21—C22	126.32 (17)	O3—C2—C5	114.13 (15)
N3—C21—C22	123.65 (16)	C6—C5—C4	119.49 (15)
C21—N4—C20	106.60 (15)	C6—C5—C2	119.58 (14)
C21—N4—Zn1ⁱ	124.56 (12)	C4—C5—C2	120.94 (15)
C20—N4—Zn1ⁱ	128.83 (12)	C8—C3—C4	119.51 (15)
C19—C20—N4	109.65 (18)	C8—C3—C1	118.67 (15)
C19—C20—H20	125.2	C4—C3—C1	121.81 (15)
N4—C20—H20	125.2	C3—C4—C5	121.11 (15)
C20—C19—N3	106.12 (18)	C3—C4—H4	119.4
C20—C19—H19	126.9	C5—C4—H4	119.4
N3—C19—H19	126.9	C7—C8—C3	118.69 (15)
C21—N3—C19	107.59 (16)	C7—C8—H8	120.7
C21—N3—C17	123.96 (16)	C3—C8—H8	120.7
C19—N3—C17	128.06 (16)	C7—C6—C5	118.47 (15)
C16—C17—C18	121.29 (17)	C7—C6—H6	120.8
C16—C17—N3	120.60 (17)	C5—C6—H6	120.8
C18—C17—N3	118.01 (17)	N1—C11—N2	109.74 (16)
C17—C16—C15	119.04 (18)	N1—C11—C12	126.32 (17)
C17—C16—H16	120.5	N2—C11—C12	123.94 (16)
C15—C16—H16	120.5	C14—C13—C18	121.25 (17)
C14—C15—C16	120.66 (19)	C14—C13—N2	120.98 (16)
C14—C15—H15	119.7	C18—C13—N2	117.76 (16)
C16—C15—H15	119.7	C10—C9—N1	110.18 (16)
O1—Zn1—O3ⁱⁱ	116.79 (6)	C10—C9—H9	124.9
O1—Zn1—N4ⁱ	111.28 (6)	N1—C9—H9	124.9
O3ⁱⁱ—Zn1—N4ⁱ	107.83 (6)	C9—C10—N2	105.23 (16)
O1—Zn1—N1	120.17 (6)	C9—C10—H10	127.4
O3ⁱⁱ—Zn1—N1	89.71 (7)	N2—C10—H10	127.4
N4ⁱ—Zn1—N1	108.89 (6)	C13—C14—C15	118.80 (17)
C1—O1—Zn1	110.96 (11)	C13—C14—H14	120.6
C2—O3—Zn1ⁱⁱⁱ	126.90 (12)	C15—C14—H14	120.6
C11—N1—C9	106.42 (15)	C8—C7—C6	122.67 (15)
C11—N1—Zn1	131.79 (12)	C8—C7—N5	118.08 (15)
C9—N1—Zn1	120.99 (12)	C6—C7—N5	119.25 (15)
C11—N2—C10	108.43 (15)	C11—C12—H12A	109.5
C11—N2—C13	126.02 (15)	C11—C12—H12B	109.5
C10—N2—C13	125.52 (15)	H12A—C12—H12B	109.5
O5—N5—O6	123.86 (17)	C11—C12—H12C	109.5
O5—N5—C7	117.93 (16)	H12A—C12—H12C	109.5
O6—N5—C7	118.19 (16)	H12B—C12—H12C	109.5
O2—C1—O1	124.40 (16)

N3—C21—N4—C20	0.2 (2)	C6—C5—C4—C3	−2.2 (2)
C22—C21—N4—C20	180.0 (2)	C2—C5—C4—C3	178.21 (15)
N3—C21—N4—Zn1ⁱ	179.29 (13)	C4—C3—C8—C7	−0.8 (2)
C22—C21—N4—Zn1ⁱ	−0.9 (3)	C1—C3—C8—C7	−179.55 (15)
C21—N4—C20—C19	0.1 (3)	C4—C5—C6—C7	0.0 (2)
Zn1ⁱ—N4—C20—C19	−178.92 (17)	C2—C5—C6—C7	179.52 (15)
N4—C20—C19—N3	−0.4 (3)	C9—N1—C11—N2	0.68 (19)
N4—C21—N3—C19	−0.4 (2)	Zn1—N1—C11—N2	−168.85 (12)
C22—C21—N3—C19	179.8 (2)	C9—N1—C11—C12	−178.95 (19)
N4—C21—N3—C17	−173.85 (17)	Zn1—N1—C11—C12	11.5 (3)
C22—C21—N3—C17	6.4 (3)	C10—N2—C11—N1	−0.8 (2)
C20—C19—N3—C21	0.5 (3)	C13—N2—C11—N1	177.48 (16)
C20—C19—N3—C17	173.5 (2)	C10—N2—C11—C12	178.89 (19)
C21—N3—C17—C16	−94.0 (2)	C13—N2—C11—C12	−2.9 (3)
C19—N3—C17—C16	94.0 (3)	C17—C18—C13—C14	−2.3 (3)
C21—N3—C17—C18	82.5 (3)	C17—C18—C13—N2	176.34 (16)
C19—N3—C17—C18	−89.6 (3)	C11—N2—C13—C14	89.3 (2)
C18—C17—C16—C15	−0.1 (3)	C10—N2—C13—C14	−92.7 (2)
N3—C17—C16—C15	176.22 (19)	C11—N2—C13—C18	−89.3 (2)
C17—C16—C15—C14	−1.5 (3)	C10—N2—C13—C18	88.6 (2)
Zn1—O1—C1—O2	8.1 (2)	C11—N1—C9—C10	−0.4 (2)
Zn1—O1—C1—C3	−172.39 (11)	Zn1—N1—C9—C10	170.53 (12)
C16—C17—C18—C13	2.0 (3)	N1—C9—C10—N2	−0.1 (2)
N3—C17—C18—C13	−174.43 (17)	C11—N2—C10—C9	0.5 (2)
Zn1ⁱⁱⁱ—O3—C2—O4	12.5 (3)	C13—N2—C10—C9	−177.75 (16)
Zn1ⁱⁱⁱ—O3—C2—C5	−167.11 (11)	C18—C13—C14—C15	0.8 (3)
O4—C2—C5—C6	15.5 (2)	N2—C13—C14—C15	−177.86 (18)
O3—C2—C5—C6	−164.86 (15)	C16—C15—C14—C13	1.2 (3)
O4—C2—C5—C4	−164.98 (16)	C3—C8—C7—C6	−1.5 (3)
O3—C2—C5—C4	14.7 (2)	C3—C8—C7—N5	177.69 (16)
O2—C1—C3—C8	−12.1 (3)	C5—C6—C7—C8	1.9 (3)
O1—C1—C3—C8	168.31 (16)	C5—C6—C7—N5	−177.26 (15)
O2—C1—C3—C4	169.14 (18)	O5—N5—C7—C8	−168.03 (18)
O1—C1—C3—C4	−10.4 (2)	O6—N5—C7—C8	13.9 (3)
C8—C3—C4—C5	2.7 (2)	O5—N5—C7—C6	11.2 (3)
C1—C3—C4—C5	−178.62 (15)	O6—N5—C7—C6	−166.90 (19)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···O2	0.96	2.40	3.291 (3)	154
C9—H9···O3ⁱⁱ	0.93	2.54	2.908 (2)	104
C10—H10···O4^iv	0.93	2.24	3.160 (3)	171
C22—H22A···O3^v	0.96	2.52	3.308 (3)	139

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

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A new two-dimensional ZnII coordination polymer based on 1,3-bis­(2-methyl-1H-imidazol-1-yl)benzene and 5-nitro­benzene-1,3-di­carb­oxy­lic acid: synthesis, crystal structure and physical properties

Supporting information

A new two-dimensional Zn^II coordination polymer based on 1,3-bis(2-methyl-1H-imidazol-1-yl)benzene and 5-nitrobenzene-1,3-dicarboxylic acid: synthesis, crystal structure and physical properties