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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.

Supporting information

cif

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

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdbzcsup2.hkl
Contains datablock bzmdbzc

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdnafsup3.hkl
Contains datablock bzmdnaf

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdmacsup4.hkl
Contains datablock bzmdmac

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmd35dnzsup5.hkl
Contains datablock bzmd35dnz

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdabnsup6.hkl
Contains datablock bzmdabn

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdslcsup7.hkl
Contains datablock bzmdslc

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdmlcsup8.hkl
Contains datablock bzmdmlc

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdiacsup9.hkl
Contains datablock bzmdiac

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdressup10.hkl
Contains datablock bzmdres

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdfmasup11.hkl
Contains datablock bzmdfma

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdmlnsup12.hkl
Contains datablock bzmdmln

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmd26dbasup13.hkl
Contains datablock bzmd26dba

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdbzcsup14.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmd35dbasup14.hkl
Contains datablock bzmd35dba

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdnafsup15.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdmacsup16.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmd35dnzsup17.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdabnsup18.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdslcsup19.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdmlcsup20.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdiacsup21.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmd26dbasup22.cml
Supplementary material

pdf

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·C7H6O2F(000) = 832
Mr = 397.38Dx = 1.366 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 13.5997 (6) ÅCell parameters from 9997 reflections
b = 9.0354 (4) Åθ = 5.1–68.0°
c = 16.5974 (8) ŵ = 0.86 mm1
β = 108.646 (2)°T = 300 K
V = 1932.42 (15) Å3Prism, clear light colourless
Z = 40.8 × 0.2 × 0.2 mm
Data collection top
Bruker APEXII CCD
diffractometer
2669 reflections with I > 2σ(I)
φ and ω scansRint = 0.053
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 68.3°, θmin = 3.7°
Tmin = 0.675, Tmax = 0.753h = 1616
60527 measured reflectionsk = 1010
3542 independent reflectionsl = 1920
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.045 w = 1/[σ2(Fo2) + (0.0462P)2 + 0.7992P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.130(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.16 e Å3
3542 reflectionsΔρmin = 0.14 e Å3
339 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction 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
xyzUiso*/Ueq
O30.57161 (11)0.97707 (18)0.14818 (9)0.0723 (4)
O1'0.65654 (13)0.60123 (18)0.53629 (11)0.0806 (5)
N10.62802 (12)0.99073 (17)0.32969 (9)0.0568 (4)
O2'0.52139 (13)0.69513 (19)0.56528 (12)0.0887 (5)
N30.79953 (14)0.9851 (2)0.30460 (11)0.0681 (5)
O10.87927 (13)0.9118 (2)0.31765 (12)0.0933 (5)
N20.65260 (13)0.80491 (19)0.42084 (11)0.0655 (5)
O40.43536 (12)0.8503 (2)0.06689 (11)0.0930 (6)
O20.78341 (14)1.1005 (2)0.26413 (12)0.0933 (6)
C1'0.61614 (14)0.4999 (2)0.65137 (12)0.0543 (4)
C10.72512 (15)0.9308 (2)0.34107 (12)0.0584 (5)
C80.60097 (15)0.8057 (2)0.05160 (12)0.0605 (5)
C7'0.59173 (15)0.6076 (2)0.57987 (12)0.0587 (5)
C30.58695 (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)
C70.52666 (16)0.8765 (3)0.08774 (12)0.0642 (5)
C20.73912 (17)0.8177 (2)0.39708 (14)0.0660 (5)
C50.5730 (2)1.1090 (2)0.27249 (15)0.0692 (6)
C90.5671 (2)0.6840 (3)0.00055 (15)0.0765 (6)
C40.4827 (2)0.9323 (3)0.38706 (18)0.0732 (6)
C60.50507 (19)1.0484 (3)0.18877 (14)0.0755 (6)
C5'0.5698 (2)0.3854 (3)0.76467 (15)0.0746 (6)
C130.70145 (18)0.8566 (3)0.06717 (15)0.0725 (6)
C4'0.6644 (2)0.3150 (3)0.79135 (16)0.0786 (7)
C120.7663 (2)0.7852 (3)0.03012 (18)0.0836 (7)
C110.7312 (2)0.6645 (3)0.02131 (17)0.0872 (8)
C3'0.7339 (2)0.3331 (3)0.74715 (17)0.0807 (7)
C100.6321 (2)0.6133 (3)0.03665 (18)0.0900 (8)
H90.497 (2)0.656 (3)0.0102 (16)0.086 (7)*
H120.838 (2)0.821 (3)0.0425 (18)0.107 (9)*
H110.774 (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)*
H130.7269 (19)0.943 (3)0.1044 (16)0.087 (8)*
H20.8006 (19)0.756 (3)0.4194 (15)0.083 (7)*
H6A0.450 (2)0.972 (3)0.1934 (17)0.101 (9)*
H6B0.468 (2)1.128 (3)0.1501 (17)0.098 (8)*
H1'0.647 (2)0.681 (4)0.494 (2)0.138 (12)*
H5A0.6277 (18)1.174 (3)0.2639 (15)0.081 (7)*
H5B0.5303 (18)1.163 (3)0.3013 (15)0.079 (7)*
H4A0.474 (2)0.864 (3)0.4331 (19)0.110 (9)*
H4B0.428 (2)0.917 (3)0.336 (2)0.109 (10)*
H4C0.476 (2)1.031 (4)0.4081 (17)0.102 (9)*
H100.608 (2)0.526 (4)0.072 (2)0.123 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0652 (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)
N10.0661 (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)
N30.0712 (11)0.0709 (11)0.0642 (10)0.0079 (9)0.0246 (9)0.0045 (9)
O10.0775 (11)0.0989 (13)0.1149 (14)0.0056 (10)0.0466 (10)0.0036 (11)
N20.0694 (10)0.0638 (10)0.0634 (10)0.0010 (8)0.0213 (8)0.0078 (8)
O40.0621 (9)0.1282 (15)0.0868 (11)0.0115 (10)0.0211 (8)0.0059 (11)
O20.0977 (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)
C10.0622 (11)0.0585 (11)0.0560 (11)0.0049 (9)0.0211 (9)0.0028 (9)
C80.0641 (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)
C30.0682 (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)
C70.0631 (12)0.0762 (14)0.0506 (11)0.0043 (10)0.0144 (9)0.0122 (10)
C20.0655 (12)0.0642 (12)0.0668 (13)0.0012 (10)0.0192 (10)0.0044 (10)
C50.0848 (15)0.0568 (12)0.0707 (14)0.0127 (11)0.0315 (12)0.0103 (10)
C90.0744 (15)0.0848 (16)0.0674 (13)0.0092 (13)0.0188 (11)0.0021 (12)
C40.0734 (14)0.0808 (16)0.0712 (15)0.0014 (12)0.0311 (12)0.0003 (13)
C60.0740 (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)
C130.0696 (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)
C120.0728 (15)0.0937 (19)0.0905 (17)0.0004 (13)0.0351 (13)0.0171 (15)
C110.100 (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)
C100.100 (2)0.0892 (19)0.0812 (17)0.0005 (16)0.0299 (15)0.0058 (14)
Geometric parameters (Å, º) top
O3—C71.347 (3)C1'—C2'1.384 (3)
O3—C61.441 (3)C1—C21.353 (3)
O1'—C7'1.308 (2)C8—C71.476 (3)
N1—C11.383 (2)C8—C91.384 (3)
N1—C31.355 (2)C8—C131.386 (3)
N1—C51.466 (3)C3—C41.477 (3)
O2'—C7'1.205 (2)C6'—C5'1.383 (3)
N3—O11.230 (2)C2'—C3'1.382 (3)
N3—O21.221 (2)C5—C61.504 (3)
N3—C11.422 (3)C9—C101.374 (4)
N2—C31.327 (3)C5'—C4'1.376 (3)
N2—C21.360 (3)C13—C121.385 (4)
O4—C71.201 (2)C4'—C3'1.379 (4)
C1'—C7'1.488 (3)C12—C111.373 (4)
C1'—C6'1.387 (3)C11—C101.370 (4)
C7—O3—C6116.51 (17)N1—C3—C4124.6 (2)
C1—N1—C5129.89 (17)N2—C3—N1111.14 (17)
C3—N1—C1105.40 (16)N2—C3—C4124.22 (19)
C3—N1—C5124.57 (18)C5'—C6'—C1'120.1 (2)
O1—N3—C1116.53 (19)C3'—C2'—C1'119.9 (2)
O2—N3—O1123.4 (2)O3—C7—C8112.86 (17)
O2—N3—C1120.10 (19)O4—C7—O3121.9 (2)
C3—N2—C2106.95 (17)O4—C7—C8125.2 (2)
C6'—C1'—C7'119.43 (18)C1—C2—N2108.58 (19)
C2'—C1'—C7'120.86 (18)N1—C5—C6111.62 (19)
C2'—C1'—C6'119.65 (19)C10—C9—C8120.7 (2)
N1—C1—N3125.81 (18)O3—C6—C5107.62 (19)
C2—C1—N1107.93 (18)C4'—C5'—C6'119.9 (2)
C2—C1—N3126.15 (19)C12—C13—C8119.5 (3)
C9—C8—C7117.7 (2)C5'—C4'—C3'120.2 (2)
C9—C8—C13119.5 (2)C11—C12—C13120.1 (3)
C13—C8—C7122.9 (2)C10—C11—C12120.6 (3)
O1'—C7'—C1'113.23 (17)C4'—C3'—C2'120.2 (2)
O2'—C7'—O1'123.35 (19)C11—C10—C9119.6 (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·C10H8OF(000) = 880
Mr = 419.43Dx = 1.311 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 8.5105 (8) ÅCell parameters from 9803 reflections
b = 22.387 (2) Åθ = 4.4–69.6°
c = 11.7752 (11) ŵ = 0.78 mm1
β = 108.664 (4)°T = 300 K
V = 2125.4 (3) Å3Prism, clear light yellow
Z = 40.42 × 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 scansRint = 0.084
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 68.3°, θmin = 4.0°
Tmin = 0.678, Tmax = 1.000h = 1010
39131 measured reflectionsk = 2626
3884 independent reflectionsl = 1413
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.058 w = 1/[σ2(Fo2) + (0.1113P)2 + 0.4215P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.193(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.30 e Å3
3884 reflectionsΔρmin = 0.23 e Å3
365 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0041 (7)
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 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
xyzUiso*/Ueq
O30.36072 (19)0.49428 (7)0.19944 (13)0.0624 (4)
O20.2808 (2)0.51266 (9)0.57654 (16)0.0842 (6)
N10.2220 (2)0.58230 (8)0.39335 (15)0.0563 (4)
O10.0234 (3)0.52273 (9)0.68439 (16)0.0850 (6)
O1'0.2411 (3)0.70227 (10)0.35022 (19)0.0908 (6)
N30.1417 (3)0.53251 (9)0.59314 (17)0.0652 (5)
O40.3769 (3)0.39564 (9)0.21856 (18)0.0892 (6)
N20.0181 (2)0.62642 (9)0.40900 (18)0.0681 (5)
C10.1092 (3)0.56838 (9)0.50416 (18)0.0562 (5)
C30.1374 (3)0.61722 (10)0.3393 (2)0.0634 (6)
C80.2958 (3)0.43345 (12)0.05661 (19)0.0658 (6)
C20.0348 (3)0.59617 (11)0.5115 (2)0.0649 (6)
C70.3486 (3)0.43791 (11)0.1652 (2)0.0633 (6)
C10'0.4667 (3)0.67583 (11)0.5266 (2)0.0675 (6)
C50.3963 (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)
C60.4166 (3)0.50046 (11)0.3028 (2)0.0623 (6)
C90.2418 (3)0.48176 (15)0.0078 (2)0.0772 (7)
C4'0.7415 (3)0.71446 (11)0.5461 (3)0.0799 (8)
C40.2096 (5)0.64272 (17)0.2172 (3)0.0859 (8)
C130.2986 (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)
C120.2455 (5)0.37083 (19)0.0939 (3)0.0984 (10)
C110.1911 (4)0.4196 (2)0.1412 (3)0.0977 (10)
C5'0.9152 (4)0.71857 (15)0.6162 (5)0.1008 (12)
C100.1889 (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)
H5A0.448 (4)0.5694 (12)0.403 (3)0.082 (8)*
H10'0.394 (3)0.6541 (11)0.559 (2)0.070 (7)*
H6A0.540 (4)0.4903 (11)0.280 (2)0.076 (7)*
H5B0.448 (3)0.5927 (11)0.277 (2)0.071 (7)*
H6B0.355 (3)0.4734 (12)0.365 (2)0.071 (7)*
H8'0.629 (5)0.6273 (16)0.736 (3)0.125 (12)*
H100.146 (4)0.5098 (15)0.128 (3)0.112 (11)*
H130.341 (4)0.3442 (15)0.041 (3)0.096 (10)*
H90.246 (4)0.5203 (15)0.043 (3)0.095 (10)*
H1'0.180 (4)0.6777 (16)0.382 (3)0.107 (11)*
H20.134 (4)0.5959 (12)0.575 (3)0.083 (8)*
H4A0.132 (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)*
H120.249 (5)0.3291 (18)0.124 (3)0.124 (12)*
H4B0.267 (5)0.6107 (19)0.157 (4)0.138 (14)*
H110.150 (4)0.4097 (16)0.213 (3)0.120 (11)*
H2'0.458 (4)0.7552 (16)0.306 (3)0.102 (11)*
H4C0.304 (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
U11U22U33U12U13U23
O30.0638 (9)0.0724 (10)0.0572 (8)0.0028 (7)0.0280 (7)0.0008 (7)
O20.0876 (13)0.1041 (14)0.0733 (11)0.0111 (10)0.0431 (10)0.0035 (9)
N10.0562 (9)0.0573 (10)0.0581 (10)0.0053 (8)0.0221 (8)0.0002 (8)
O10.0934 (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)
N30.0746 (13)0.0691 (12)0.0586 (11)0.0051 (10)0.0308 (10)0.0026 (9)
O40.1245 (16)0.0762 (11)0.0852 (12)0.0154 (10)0.0589 (11)0.0029 (9)
N20.0683 (12)0.0661 (12)0.0741 (12)0.0026 (9)0.0287 (10)0.0014 (9)
C10.0613 (12)0.0563 (11)0.0538 (11)0.0060 (9)0.0226 (9)0.0004 (9)
C30.0694 (14)0.0577 (12)0.0677 (13)0.0034 (10)0.0286 (11)0.0043 (10)
C80.0571 (12)0.0904 (17)0.0500 (11)0.0015 (11)0.0173 (9)0.0006 (10)
C20.0649 (14)0.0645 (13)0.0660 (14)0.0048 (11)0.0219 (11)0.0037 (11)
C70.0619 (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)
C50.0541 (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)
C60.0593 (13)0.0755 (15)0.0585 (13)0.0031 (11)0.0278 (10)0.0014 (11)
C90.0732 (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)
C40.094 (2)0.088 (2)0.0754 (17)0.0009 (18)0.0263 (16)0.0244 (15)
C130.0924 (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)
C120.103 (2)0.123 (3)0.0663 (16)0.030 (2)0.0229 (16)0.0136 (17)
C110.0785 (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)
C100.0742 (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—C71.339 (3)C1'—C2'1.417 (4)
O3—C61.448 (3)C6—H6A1.02 (3)
O2—N31.221 (3)C6—H6B0.96 (3)
N1—C11.385 (3)C9—C101.395 (4)
N1—C31.352 (3)C9—H90.96 (3)
N1—C51.468 (3)C4'—C3'1.393 (5)
O1—N31.234 (3)C4'—C5'1.447 (5)
O1'—C1'1.356 (3)C4—H4A0.88 (4)
O1'—H1'0.91 (4)C4—H4B1.02 (5)
N3—C11.416 (3)C4—H4C1.00 (5)
O4—C71.202 (3)C13—C121.395 (4)
N2—C31.332 (3)C13—H130.98 (3)
N2—C21.351 (3)C8'—C7'1.364 (4)
C1—C21.352 (3)C8'—H8'1.02 (4)
C3—C41.484 (4)C2'—C3'1.348 (5)
C8—C71.488 (3)C2'—H2'0.87 (3)
C8—C91.371 (4)C3'—H3'0.95 (4)
C8—C131.386 (4)C12—C111.372 (5)
C2—H20.93 (3)C12—H121.00 (4)
C10'—C9'1.419 (4)C11—C101.362 (5)
C10'—C1'1.361 (4)C11—H111.04 (4)
C10'—H10'0.95 (3)C5'—C6'1.356 (6)
C5—C61.492 (3)C5'—H5'0.96 (3)
C5—H5A0.95 (3)C10—H101.01 (4)
C5—H5B0.99 (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—C6114.89 (17)H6A—C6—H6B109 (2)
C1—N1—C5128.84 (19)C8—C9—C10120.4 (3)
C3—N1—C1105.12 (18)C8—C9—H9117.6 (19)
C3—N1—C5126.04 (19)C10—C9—H9122 (2)
C1'—O1'—H1'112 (2)C9'—C4'—C5'117.7 (3)
O2—N3—O1123.6 (2)C3'—C4'—C9'118.7 (3)
O2—N3—C1119.8 (2)C3'—C4'—C5'123.5 (3)
O1—N3—C1116.5 (2)C3—C4—H4A109 (3)
C3—N2—C2105.8 (2)C3—C4—H4B111 (2)
N1—C1—N3125.74 (19)C3—C4—H4C112 (3)
C2—C1—N1107.28 (19)H4A—C4—H4B116 (3)
C2—C1—N3127.0 (2)H4A—C4—H4C107 (4)
N1—C3—C4124.1 (2)H4B—C4—H4C101 (4)
N2—C3—N1111.9 (2)C8—C13—C12119.5 (3)
N2—C3—C4124.0 (2)C8—C13—H13117.7 (19)
C9—C8—C7122.8 (2)C12—C13—H13122.7 (19)
C9—C8—C13119.7 (2)C9'—C8'—H8'116 (2)
C13—C8—C7117.5 (2)C7'—C8'—C9'121.7 (3)
N2—C2—C1109.9 (2)C7'—C8'—H8'122 (2)
N2—C2—H2121.8 (18)C1'—C2'—H2'113 (2)
C1—C2—H2128.3 (18)C3'—C2'—C1'120.5 (3)
O3—C7—C8113.3 (2)C3'—C2'—H2'126 (2)
O4—C7—O3122.5 (2)C4'—C3'—H3'113 (2)
O4—C7—C8124.2 (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—H12115 (2)
C1'—C10'—H10'119.1 (15)C11—C12—C13120.0 (3)
N1—C5—C6113.15 (19)C11—C12—H12125 (2)
N1—C5—H5A107.8 (17)C12—C11—H11114 (2)
N1—C5—H5B106.3 (14)C10—C11—C12120.6 (3)
C6—C5—H5A108.5 (17)C10—C11—H11125 (2)
C6—C5—H5B113.1 (14)C4'—C5'—H5'110 (2)
H5A—C5—H5B108 (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—H10121 (2)
C8'—C9'—C10'122.2 (2)C11—C10—C9119.8 (3)
O1'—C1'—C10'124.8 (2)C11—C10—H10119 (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—C5108.53 (19)C7'—C6'—H6'119 (2)
O3—C6—H6A110.0 (15)C8'—C7'—C6'119.9 (4)
O3—C6—H6B109.4 (15)C8'—C7'—H7'126 (3)
C5—C6—H6A107.5 (14)C6'—C7'—H7'114 (3)
C5—C6—H6B112.5 (15)
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–4-methoxybenzoic acid (1/1) (bzmdmac) top
Crystal data top
C13H13N3O4·C8H8O3Z = 2
Mr = 427.41F(000) = 448
Triclinic, P1Dx = 1.416 Mg m3
a = 9.1309 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.1274 (4) ÅCell parameters from 9919 reflections
c = 11.8538 (5) Åθ = 2.5–27.5°
α = 107.365 (1)°µ = 0.11 mm1
β = 103.270 (1)°T = 300 K
γ = 110.091 (1)°Plate, clear light colourless
V = 1002.73 (7) Å30.73 × 0.49 × 0.21 mm
Data collection top
Bruker APEX3 microsource
diffractometer
3795 reflections with I > 2σ(I)
φ and ω scansRint = 0.063
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 27.5°, θmin = 3.6°
Tmin = 0.587, Tmax = 0.746h = 1111
32021 measured reflectionsk = 1414
4583 independent reflectionsl = 1515
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059All H-atom parameters refined
wR(F2) = 0.165 w = 1/[σ2(Fo2) + (0.0785P)2 + 0.4129P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4583 reflectionsΔρmax = 0.76 e Å3
364 parametersΔρmin = 0.24 e Å3
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 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
xyzUiso*/Ueq
O30.25372 (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)
O40.3621 (2)0.82888 (18)0.41261 (14)0.0592 (4)
O20.2647 (2)0.86239 (18)0.88018 (15)0.0624 (4)
O10.4097 (2)0.84360 (19)1.03975 (14)0.0675 (5)
N10.43006 (18)0.75915 (15)0.73271 (14)0.0395 (3)
N30.3715 (2)0.83160 (16)0.92979 (14)0.0442 (4)
N20.63325 (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)
C80.1692 (2)0.91266 (18)0.33808 (16)0.0395 (4)
C50.3002 (2)0.76950 (19)0.64032 (17)0.0423 (4)
C3'1.2086 (2)0.39608 (19)0.68643 (17)0.0420 (4)
C30.4572 (2)0.77942 (18)0.85787 (16)0.0391 (4)
C4'1.2720 (2)0.40079 (19)0.80701 (17)0.0418 (4)
C70.2705 (2)0.88207 (19)0.43220 (17)0.0420 (4)
C10.5419 (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)
C20.5799 (2)0.7421 (2)0.89668 (18)0.0460 (4)
C60.3670 (3)0.9180 (2)0.64893 (18)0.0482 (4)
C40.5590 (3)0.6836 (3)0.5775 (2)0.0540 (5)
C5'1.2197 (3)0.4587 (2)0.90209 (18)0.0474 (4)
C90.1616 (3)0.8622 (2)0.21389 (18)0.0508 (5)
C8'1.4517 (4)0.2998 (3)0.7517 (3)0.0650 (6)
C130.0911 (3)0.9973 (3)0.3722 (2)0.0545 (5)
C110.0037 (3)0.9767 (3)0.1587 (2)0.0651 (6)
C100.0749 (3)0.8943 (3)0.1246 (2)0.0639 (6)
C120.0049 (3)1.0293 (3)0.2823 (3)0.0670 (6)
H5A0.269 (3)0.702 (2)0.552 (2)0.046 (5)*
H5B0.194 (3)0.744 (2)0.6573 (19)0.041 (5)*
H6A0.480 (3)0.942 (2)0.640 (2)0.055 (6)*
H6B0.373 (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)*
H4A0.645 (3)0.659 (2)0.577 (2)0.056 (6)*
H20.624 (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'A1.509 (4)0.375 (3)0.726 (3)0.081 (8)*
H90.219 (3)0.804 (3)0.190 (2)0.069 (7)*
H130.095 (3)1.031 (3)0.451 (3)0.066 (7)*
H4B0.458 (4)0.606 (3)0.509 (3)0.090 (9)*
H1'0.798 (4)0.636 (3)0.811 (3)0.086 (9)*
H4C0.579 (4)0.759 (3)0.556 (3)0.084 (9)*
H8'B1.362 (4)0.219 (3)0.681 (3)0.088 (9)*
H8'C1.527 (4)0.271 (3)0.796 (3)0.079 (8)*
H100.069 (4)0.855 (3)0.037 (3)0.096 (9)*
H120.045 (4)1.088 (3)0.313 (3)0.095 (10)*
H110.073 (4)0.990 (3)0.088 (3)0.082 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0631 (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)
O40.0709 (9)0.0877 (10)0.0554 (8)0.0566 (9)0.0350 (7)0.0419 (8)
O20.0763 (10)0.0866 (11)0.0602 (9)0.0601 (9)0.0375 (8)0.0386 (8)
O10.0819 (11)0.0950 (12)0.0368 (7)0.0490 (10)0.0272 (7)0.0260 (8)
N10.0455 (7)0.0473 (8)0.0370 (7)0.0274 (6)0.0182 (6)0.0213 (6)
N30.0501 (8)0.0473 (8)0.0407 (8)0.0245 (7)0.0208 (7)0.0187 (6)
N20.0451 (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)
C80.0384 (8)0.0490 (9)0.0381 (8)0.0209 (7)0.0165 (7)0.0235 (7)
C50.0425 (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)
C30.0433 (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)
C70.0463 (9)0.0523 (9)0.0405 (9)0.0277 (8)0.0205 (7)0.0256 (8)
C10.0431 (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)
C20.0468 (9)0.0588 (11)0.0402 (9)0.0285 (8)0.0152 (7)0.0249 (8)
C60.0546 (11)0.0501 (10)0.0388 (9)0.0232 (8)0.0120 (8)0.0209 (8)
C40.0650 (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)
C90.0606 (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)
C130.0622 (12)0.0804 (14)0.0480 (11)0.0464 (11)0.0302 (9)0.0363 (10)
C110.0629 (13)0.0952 (17)0.0603 (13)0.0452 (13)0.0218 (11)0.0504 (13)
C100.0773 (15)0.0840 (15)0.0384 (10)0.0415 (13)0.0187 (10)0.0308 (10)
C120.0744 (15)0.0998 (18)0.0706 (15)0.0638 (14)0.0384 (12)0.0524 (14)
Geometric parameters (Å, º) top
O3—C71.355 (2)C3'—C4'1.391 (2)
O3—C61.446 (2)C3'—H3'0.96 (3)
O1'—C7'1.320 (2)C3—C21.355 (2)
O1'—H1'0.84 (3)C4'—C5'1.392 (3)
O3'—C4'1.359 (2)C1—C41.482 (3)
O3'—C8'1.421 (3)C6'—C5'1.369 (3)
O2'—C7'1.217 (2)C6'—H6'0.94 (3)
O4—C71.204 (2)C2—H20.97 (3)
O2—N31.225 (2)C6—H6A1.01 (2)
O1—N31.222 (2)C6—H6B1.04 (2)
N1—C51.480 (2)C4—H4A0.92 (3)
N1—C31.381 (2)C4—H4B0.97 (3)
N1—C11.350 (2)C4—H4C0.92 (3)
N3—C31.414 (2)C5'—H5'0.94 (3)
N2—C11.331 (2)C9—C101.382 (3)
N2—C21.361 (2)C9—H90.98 (3)
C2'—C1'1.391 (2)C8'—H8'A1.00 (3)
C2'—C3'1.384 (2)C8'—H8'B0.95 (3)
C2'—H2'0.97 (2)C8'—H8'C0.98 (3)
C1'—C7'1.481 (2)C13—C121.384 (3)
C1'—C6'1.397 (2)C13—H130.88 (3)
C8—C71.478 (2)C11—C101.372 (4)
C8—C91.386 (3)C11—C121.379 (4)
C8—C131.388 (3)C11—H111.01 (3)
C5—C61.513 (3)C10—H100.98 (3)
C5—H5A1.00 (2)C12—H120.95 (3)
C5—H5B1.00 (2)
C7—O3—C6115.93 (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—C5130.29 (14)N2—C2—H2122.3 (16)
C1—N1—C5123.92 (15)C3—C2—N2109.30 (16)
C1—N1—C3105.61 (14)C3—C2—H2128.3 (16)
O2—N3—C3119.27 (15)O3—C6—C5109.66 (15)
O1—N3—O2123.58 (16)O3—C6—H6A109.6 (13)
O1—N3—C3117.15 (16)O3—C6—H6B107.7 (12)
C1—N2—C2106.00 (15)C5—C6—H6A107.2 (12)
C1'—C2'—H2'121.8 (13)C5—C6—H6B109.6 (12)
C3'—C2'—C1'121.08 (16)H6A—C6—H6B113.0 (18)
C3'—C2'—H2'117.1 (13)C1—C4—H4A110.3 (15)
C2'—C1'—C7'119.62 (15)C1—C4—H4B112.5 (18)
C2'—C1'—C6'118.55 (16)C1—C4—H4C111.9 (19)
C6'—C1'—C7'121.83 (16)H4A—C4—H4B107 (2)
C9—C8—C7118.52 (16)H4A—C4—H4C109 (2)
C9—C8—C13119.36 (17)H4B—C4—H4C106 (3)
C13—C8—C7121.99 (16)C4'—C5'—H5'119.7 (16)
N1—C5—C6108.80 (15)C6'—C5'—C4'120.21 (17)
N1—C5—H5A111.9 (12)C6'—C5'—H5'120.1 (16)
N1—C5—H5B111.0 (11)C8—C9—H9119.7 (15)
C6—C5—H5A109.4 (12)C10—C9—C8120.3 (2)
C6—C5—H5B110.5 (11)C10—C9—H9120.1 (15)
H5A—C5—H5B105.3 (16)O3'—C8'—H8'A108.8 (17)
C2'—C3'—C4'119.46 (16)O3'—C8'—H8'B108.8 (19)
C2'—C3'—H3'119.6 (15)O3'—C8'—H8'C104.0 (17)
C4'—C3'—H3'120.9 (15)H8'A—C8'—H8'B111 (3)
N1—C3—N3124.90 (15)H8'A—C8'—H8'C114 (2)
C2—C3—N1107.41 (15)H8'B—C8'—H8'C109 (2)
C2—C3—N3127.68 (16)C8—C13—H13120.7 (17)
O3'—C4'—C3'124.69 (17)C12—C13—C8120.1 (2)
O3'—C4'—C5'115.47 (16)C12—C13—H13119.3 (17)
C3'—C4'—C5'119.83 (16)C10—C11—C12120.4 (2)
O3—C7—C8112.45 (14)C10—C11—H11116.3 (16)
O4—C7—O3122.94 (16)C12—C11—H11123.2 (17)
O4—C7—C8124.57 (16)C9—C10—H10118.5 (19)
N1—C1—C4123.52 (16)C11—C10—C9120.0 (2)
N2—C1—N1111.65 (15)C11—C10—H10121.4 (19)
N2—C1—C4124.83 (16)C13—C12—H12115 (2)
O1'—C7'—C1'113.17 (15)C11—C12—C13119.9 (2)
O2'—C7'—O1'123.39 (17)C11—C12—H12125 (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·C7H4N2O6F(000) = 1008
Mr = 487.39Dx = 1.533 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 21.0988 (13) ÅCell parameters from 9941 reflections
b = 8.4322 (5) Åθ = 2.6–27.3°
c = 12.0341 (8) ŵ = 0.13 mm1
β = 99.505 (2)°T = 300 K
V = 2111.6 (2) Å3Plate, clear light colourless
Z = 40.46 × 0.40 × 0.06 mm
Data collection top
Bruker APEXII CCD
diffractometer
3321 reflections with I > 2σ(I)
φ and ω scansRint = 0.108
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 27.5°, θmin = 2.6°
Tmin = 0.587, Tmax = 0.746h = 2727
71598 measured reflectionsk = 1010
4820 independent reflectionsl = 1515
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.065 w = 1/[σ2(Fo2) + (0.0808P)2 + 2.0317P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.213(Δ/σ)max < 0.001
S = 1.14Δρmax = 0.40 e Å3
4820 reflectionsΔρmin = 0.35 e Å3
385 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.026 (4)
Primary atom site location: dual
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 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
xyzUiso*/Ueq
O30.88887 (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)
N10.84690 (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)
N20.74971 (11)0.4037 (3)0.9065 (2)0.0485 (6)
N1'0.38764 (11)0.3936 (3)0.8979 (2)0.0500 (6)
O20.95921 (11)0.3723 (4)1.0441 (2)0.0787 (9)
O40.97119 (11)0.5544 (4)0.6211 (3)0.0766 (8)
N30.90992 (12)0.4399 (4)1.0593 (2)0.0521 (7)
O10.90695 (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)
C10.78368 (13)0.3235 (4)0.8418 (3)0.0434 (7)
C3'0.42799 (13)0.5640 (3)0.6359 (3)0.0436 (7)
C30.85199 (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)
C70.91451 (14)0.5258 (4)0.6079 (3)0.0493 (7)
C80.86719 (15)0.5910 (4)0.5147 (3)0.0482 (7)
C50.89796 (15)0.2510 (4)0.8332 (3)0.0493 (7)
C60.93347 (15)0.3681 (5)0.7725 (3)0.0523 (8)
C20.79212 (14)0.4589 (4)0.9961 (3)0.0480 (7)
C110.7809 (2)0.7221 (5)0.3390 (4)0.0706 (11)
C40.75565 (19)0.2433 (6)0.7357 (4)0.0639 (10)
C100.75929 (19)0.6644 (5)0.4327 (4)0.0685 (10)
C90.80146 (16)0.5962 (4)0.5207 (3)0.0569 (8)
C130.8889 (2)0.6517 (4)0.4218 (3)0.0613 (9)
C120.8460 (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)*
H5A0.8774 (17)0.173 (4)0.780 (3)0.057 (10)*
H6'0.5098 (15)0.409 (4)0.912 (3)0.044 (8)*
H5B0.9296 (17)0.201 (4)0.897 (3)0.059 (10)*
H20.7782 (19)0.516 (5)1.051 (3)0.066 (11)*
H6A0.9522 (16)0.454 (4)0.825 (3)0.049 (9)*
H90.7866 (16)0.548 (4)0.590 (3)0.047 (9)*
H1'0.671 (2)0.429 (5)0.882 (3)0.073 (12)*
H6B0.9718 (18)0.319 (4)0.747 (3)0.060 (10)*
H130.935 (2)0.639 (6)0.419 (4)0.089 (14)*
H100.714 (2)0.669 (5)0.439 (4)0.084 (13)*
H120.866 (2)0.751 (6)0.265 (5)0.110 (17)*
H110.7488 (19)0.769 (5)0.276 (3)0.067 (11)*
H4A0.759 (2)0.131 (7)0.751 (4)0.104 (17)*
H4B0.773 (2)0.282 (5)0.668 (4)0.072 (12)*
H4C0.711 (3)0.267 (6)0.716 (4)0.099 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0329 (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)
N10.0306 (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)
N20.0296 (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)
O20.0378 (12)0.124 (2)0.0699 (17)0.0138 (14)0.0042 (11)0.0054 (16)
O40.0367 (12)0.104 (2)0.089 (2)0.0152 (13)0.0115 (12)0.0193 (16)
N30.0404 (13)0.0696 (18)0.0443 (15)0.0002 (12)0.0013 (11)0.0053 (13)
O10.0725 (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)
C10.0313 (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)
C30.0347 (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)
C70.0379 (14)0.0588 (18)0.0526 (18)0.0064 (13)0.0118 (13)0.0055 (14)
C80.0451 (15)0.0503 (17)0.0493 (17)0.0048 (13)0.0079 (13)0.0066 (13)
C50.0384 (15)0.0557 (18)0.0552 (18)0.0062 (13)0.0119 (13)0.0000 (15)
C60.0348 (14)0.072 (2)0.0505 (18)0.0036 (14)0.0081 (13)0.0011 (16)
C20.0408 (15)0.0587 (18)0.0456 (17)0.0085 (13)0.0100 (13)0.0043 (14)
C110.081 (3)0.055 (2)0.067 (2)0.0016 (19)0.013 (2)0.0025 (18)
C40.050 (2)0.077 (3)0.061 (2)0.0153 (18)0.0006 (16)0.0085 (19)
C100.052 (2)0.063 (2)0.085 (3)0.0061 (17)0.0068 (19)0.006 (2)
C90.0441 (17)0.0586 (19)0.066 (2)0.0098 (14)0.0048 (15)0.0023 (17)
C130.065 (2)0.059 (2)0.063 (2)0.0035 (17)0.0208 (18)0.0003 (17)
C120.103 (3)0.058 (2)0.055 (2)0.007 (2)0.016 (2)0.0025 (17)
Geometric parameters (Å, º) top
O3—C71.347 (4)C6'—H6'0.97 (3)
O3—C61.446 (4)C1—C41.478 (5)
O1'—C7'1.308 (4)C3'—C2'1.374 (4)
O1'—H1'0.99 (4)C3—C21.356 (4)
O6'—N1'1.227 (4)C2'—H2'0.98 (3)
O2'—C7'1.208 (4)C7—C81.479 (5)
N1—C11.350 (3)C8—C91.401 (4)
N1—C31.382 (4)C8—C131.375 (5)
N1—C51.469 (4)C5—C61.501 (5)
O3'—N2'1.225 (4)C5—H5A0.97 (4)
O5'—N1'1.223 (3)C5—H5B1.02 (4)
O4'—N2'1.225 (3)C6—H6A1.00 (4)
N2—C11.328 (4)C6—H6B1.00 (4)
N2—C21.364 (4)C2—H20.91 (4)
N1'—C1'1.467 (4)C11—C101.373 (6)
O2—N31.226 (4)C11—C121.387 (6)
O4—C71.204 (4)C11—H111.01 (4)
N3—O11.221 (4)C4—H4A0.97 (6)
N3—C31.419 (4)C4—H4B1.01 (4)
N2'—C3'1.469 (4)C4—H4C0.95 (5)
C5'—C4'1.379 (4)C10—C91.390 (5)
C5'—C6'1.391 (4)C10—H100.97 (5)
C5'—C7'1.499 (4)C9—H91.02 (3)
C1'—C6'1.393 (4)C13—C121.384 (6)
C1'—C2'1.375 (4)C13—H130.98 (4)
C4'—C3'1.390 (4)C12—H121.04 (5)
C4'—H4'1.05 (3)
C7—O3—C6115.6 (2)O3—C7—C8114.1 (2)
C7'—O1'—H1'113 (2)O4—C7—O3122.1 (3)
C1—N1—C3105.5 (2)O4—C7—C8123.8 (3)
C1—N1—C5125.4 (3)C9—C8—C7121.5 (3)
C3—N1—C5129.1 (2)C13—C8—C7118.8 (3)
C1—N2—C2106.9 (2)C13—C8—C9119.7 (3)
O6'—N1'—C1'118.2 (2)N1—C5—C6113.0 (3)
O5'—N1'—O6'123.9 (3)N1—C5—H5A107 (2)
O5'—N1'—C1'117.9 (3)N1—C5—H5B107 (2)
O2—N3—C3119.2 (3)C6—C5—H5A109 (2)
O1—N3—O2123.7 (3)C6—C5—H5B108 (2)
O1—N3—C3117.0 (3)H5A—C5—H5B113 (3)
O3'—N2'—C3'118.5 (3)O3—C6—C5107.8 (3)
O4'—N2'—O3'123.6 (3)O3—C6—H6A112.3 (19)
O4'—N2'—C3'117.9 (3)O3—C6—H6B111 (2)
C4'—C5'—C6'120.5 (3)C5—C6—H6A110.1 (19)
C4'—C5'—C7'118.5 (3)C5—C6—H6B112 (2)
C6'—C5'—C7'120.9 (3)H6A—C6—H6B104 (3)
C6'—C1'—N1'118.4 (3)N2—C2—H2121 (2)
C2'—C1'—N1'118.8 (2)C3—C2—N2108.2 (3)
C2'—C1'—C6'122.8 (3)C3—C2—H2131 (3)
C5'—C4'—C3'118.8 (3)C10—C11—C12119.3 (4)
C5'—C4'—H4'125.4 (18)C10—C11—H11119 (2)
C3'—C4'—H4'115.8 (18)C12—C11—H11122 (2)
C5'—C6'—C1'118.2 (3)C1—C4—H4A106 (3)
C5'—C6'—H6'125.2 (18)C1—C4—H4B114 (2)
C1'—C6'—H6'116.6 (19)C1—C4—H4C111 (3)
N1—C1—C4124.5 (3)H4A—C4—H4B116 (4)
N2—C1—N1111.3 (3)H4A—C4—H4C107 (4)
N2—C1—C4124.2 (3)H4B—C4—H4C102 (4)
C4'—C3'—N2'118.8 (3)C11—C10—C9121.0 (4)
C2'—C3'—N2'118.5 (3)C11—C10—H10121 (3)
C2'—C3'—C4'122.7 (3)C9—C10—H10118 (3)
N1—C3—N3125.1 (3)C8—C9—H9117.9 (19)
C2—C3—N1108.0 (3)C10—C9—C8119.2 (4)
C2—C3—N3126.7 (3)C10—C9—H9122.9 (19)
O1'—C7'—C5'113.6 (3)C8—C13—C12120.3 (4)
O2'—C7'—O1'124.5 (3)C8—C13—H13117 (3)
O2'—C7'—C5'122.0 (3)C12—C13—H13123 (3)
C1'—C2'—H2'122.6 (18)C11—C12—H12124 (3)
C3'—C2'—C1'117.0 (3)C13—C12—C11120.5 (4)
C3'—C2'—H2'120.4 (18)C13—C12—H12115 (3)
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–3-aminobenzoic acid (1/1) (bzmdabn) top
Crystal data top
C13H13N3O4·C7H7NO2Z = 2
Mr = 412.40F(000) = 432
Triclinic, P1Dx = 1.254 Mg m3
a = 7.9316 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.9585 (12) ÅCell parameters from 6174 reflections
c = 12.1978 (12) Åθ = 2.7–29.7°
α = 76.362 (3)°µ = 0.09 mm1
β = 78.927 (3)°T = 300 K
γ = 79.583 (3)°Plate, clear light colourless
V = 1092.21 (18) Å30.91 × 0.09 × 0.05 mm
Data collection top
Bruker APEXII CCD
diffractometer
2711 reflections with I > 2σ(I)
φ and ω scansRint = 0.090
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 27.5°, θmin = 2.6°
Tmin = 0.587, Tmax = 0.746h = 1010
38219 measured reflectionsk = 1515
5008 independent reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.054H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.168 w = 1/[σ2(Fo2) + (0.0722P)2 + 0.2049P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
5008 reflectionsΔρmax = 0.25 e Å3
340 parametersΔρmin = 0.19 e Å3
0 restraints
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 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
xyzUiso*/Ueq
O10.4965 (2)0.14226 (17)0.07569 (17)0.0875 (6)
O20.2393 (2)0.07338 (15)0.03516 (16)0.0810 (5)
O30.13769 (18)0.29191 (12)0.00673 (13)0.0578 (4)
O40.1642 (3)0.33490 (16)0.18307 (15)0.0845 (6)
N10.2025 (2)0.08578 (15)0.17918 (14)0.0541 (4)
N20.3948 (3)0.0924 (2)0.28556 (17)0.0710 (6)
N30.3595 (3)0.07569 (17)0.08576 (17)0.0646 (5)
C10.3443 (3)0.00215 (19)0.15970 (18)0.0558 (5)
C20.4600 (3)0.0087 (3)0.2261 (2)0.0691 (7)
H20.569 (4)0.039 (2)0.230 (2)0.083 (8)*
C30.2405 (3)0.1382 (2)0.25590 (18)0.0612 (6)
C40.1251 (4)0.2346 (3)0.3018 (2)0.0881 (8)
H4A0.1037830.2993890.2401580.132*
H4B0.1799960.2578550.3548420.132*
H4C0.0170950.2088280.3401570.132*
C50.0448 (3)0.1185 (2)0.1250 (2)0.0619 (6)
H5A0.003 (3)0.051 (2)0.1289 (18)0.063 (6)*
H5B0.040 (3)0.1650 (19)0.1716 (19)0.062 (6)*
C60.0791 (3)0.1848 (2)0.0046 (2)0.0604 (6)
H6A0.170 (3)0.141 (2)0.0427 (19)0.065 (7)*
H6B0.029 (3)0.204 (2)0.027 (2)0.070 (7)*
C70.1776 (3)0.3604 (2)0.0960 (2)0.0584 (5)
C80.2397 (3)0.46813 (19)0.0895 (2)0.0578 (5)
C90.2958 (4)0.5415 (2)0.1918 (3)0.0776 (7)
H90.294 (3)0.518 (2)0.264 (2)0.080 (8)*
C100.3595 (4)0.6420 (3)0.1898 (4)0.0939 (10)
H100.397 (5)0.693 (3)0.261 (3)0.130 (12)*
C110.3661 (4)0.6693 (3)0.0888 (4)0.0907 (9)
H110.415 (4)0.744 (3)0.091 (2)0.104 (9)*
C120.3096 (3)0.5983 (3)0.0117 (3)0.0803 (8)
H120.316 (4)0.613 (2)0.085 (3)0.098 (9)*
C130.2470 (3)0.4974 (2)0.0121 (2)0.0657 (6)
H130.210 (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'A1.138 (4)0.198 (3)0.722 (3)0.110 (11)*
H1'B1.168 (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
U11U22U33U12U13U23
O10.0721 (11)0.0846 (13)0.0996 (14)0.0064 (10)0.0086 (10)0.0243 (11)
O20.0819 (12)0.0795 (12)0.0981 (13)0.0162 (9)0.0341 (10)0.0308 (10)
O30.0616 (9)0.0565 (9)0.0611 (9)0.0122 (7)0.0197 (7)0.0130 (7)
O40.1176 (15)0.0857 (13)0.0643 (11)0.0287 (11)0.0359 (10)0.0148 (9)
N10.0496 (10)0.0614 (11)0.0536 (10)0.0155 (8)0.0120 (8)0.0075 (8)
N20.0744 (13)0.0885 (15)0.0583 (12)0.0274 (11)0.0234 (10)0.0090 (11)
N30.0614 (12)0.0627 (12)0.0695 (12)0.0124 (10)0.0100 (10)0.0106 (10)
C10.0496 (12)0.0627 (13)0.0567 (12)0.0138 (10)0.0131 (9)0.0073 (10)
C20.0572 (14)0.0846 (18)0.0661 (15)0.0151 (13)0.0201 (12)0.0047 (13)
C30.0686 (14)0.0683 (15)0.0503 (12)0.0228 (12)0.0090 (11)0.0098 (11)
C40.105 (2)0.093 (2)0.0704 (17)0.0207 (17)0.0032 (15)0.0293 (15)
C50.0464 (12)0.0662 (15)0.0762 (16)0.0133 (11)0.0165 (11)0.0113 (13)
C60.0582 (13)0.0589 (14)0.0733 (15)0.0104 (11)0.0284 (12)0.0154 (12)
C70.0557 (12)0.0619 (14)0.0627 (14)0.0050 (10)0.0226 (10)0.0149 (11)
C80.0489 (11)0.0547 (13)0.0701 (15)0.0012 (9)0.0143 (10)0.0142 (11)
C90.0828 (18)0.0676 (17)0.0798 (18)0.0069 (13)0.0178 (14)0.0089 (14)
C100.092 (2)0.0645 (18)0.115 (3)0.0164 (15)0.0123 (19)0.0019 (19)
C110.0734 (18)0.0643 (18)0.137 (3)0.0069 (14)0.0119 (18)0.032 (2)
C120.0664 (16)0.0819 (19)0.106 (2)0.0073 (14)0.0108 (15)0.0497 (18)
C130.0560 (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—N31.229 (3)C9—C101.393 (4)
O2—N31.224 (2)C10—H100.96 (4)
O3—C61.446 (3)C10—C111.360 (5)
O3—C71.341 (3)C11—H111.02 (3)
O4—C71.201 (3)C11—C121.364 (5)
N1—C11.387 (3)C12—H120.96 (3)
N1—C31.346 (3)C12—C131.385 (4)
N1—C51.474 (3)C13—H130.94 (3)
N2—C21.344 (3)O1'—H1'1.00 (4)
N2—C31.328 (3)O1'—C7'1.312 (3)
N3—C11.417 (3)O2'—C7'1.202 (3)
C1—C21.358 (3)N1'—H1'A0.90 (3)
C2—H20.95 (3)N1'—H1'B0.89 (3)
C3—C41.485 (4)N1'—C5'1.383 (3)
C4—H4A0.9600C7'—C1'1.490 (3)
C4—H4B0.9600C1'—C2'1.384 (4)
C4—H4C0.9600C1'—C6'1.388 (3)
C5—H5A0.95 (2)C2'—H2'1.08 (3)
C5—H5B0.98 (2)C2'—C3'1.384 (4)
C5—C61.495 (3)C3'—H3'1.05 (3)
C6—H6A0.99 (2)C3'—C4'1.374 (4)
C6—H6B0.97 (2)C4'—H4'1.02 (3)
C7—C81.484 (3)C4'—C5'1.381 (4)
C8—C91.391 (4)C5'—C6'1.391 (3)
C8—C131.379 (3)C6'—H6'1.01 (2)
C9—H90.98 (3)
C7—O3—C6115.09 (17)C8—C9—H9118.2 (15)
C1—N1—C5129.03 (19)C8—C9—C10119.7 (3)
C3—N1—C1105.68 (18)C10—C9—H9122.1 (15)
C3—N1—C5125.2 (2)C9—C10—H10119 (2)
C3—N2—C2106.95 (19)C11—C10—C9120.5 (3)
O1—N3—C1116.9 (2)C11—C10—H10121 (2)
O2—N3—O1123.5 (2)C10—C11—H11117.9 (17)
O2—N3—C1119.6 (2)C10—C11—C12120.1 (3)
N1—C1—N3125.25 (18)C12—C11—H11122.0 (17)
C2—C1—N1106.9 (2)C11—C12—H12122.7 (18)
C2—C1—N3127.8 (2)C11—C12—C13120.6 (3)
N2—C2—C1109.2 (2)C13—C12—H12116.7 (18)
N2—C2—H2125.6 (16)C8—C13—C12120.2 (3)
C1—C2—H2125.2 (16)C8—C13—H13119.1 (15)
N1—C3—C4124.6 (2)C12—C13—H13120.7 (16)
N2—C3—N1111.2 (2)C7'—O1'—H1'108.1 (19)
N2—C3—C4124.2 (2)H1'A—N1'—H1'B120 (3)
C3—C4—H4A109.5C5'—N1'—H1'A114 (2)
C3—C4—H4B109.5C5'—N1'—H1'B115.7 (19)
C3—C4—H4C109.5O1'—C7'—C1'113.7 (2)
H4A—C4—H4B109.5O2'—C7'—O1'122.9 (2)
H4A—C4—H4C109.5O2'—C7'—C1'123.3 (2)
H4B—C4—H4C109.5C2'—C1'—C7'121.1 (2)
N1—C5—H5A108.9 (13)C2'—C1'—C6'120.4 (2)
N1—C5—H5B107.3 (13)C6'—C1'—C7'118.5 (2)
N1—C5—C6112.39 (18)C1'—C2'—H2'120.0 (16)
H5A—C5—H5B106.2 (19)C1'—C2'—C3'118.3 (3)
C6—C5—H5A111.2 (13)C3'—C2'—H2'121.6 (16)
C6—C5—H5B110.6 (13)C2'—C3'—H3'117.9 (19)
O3—C6—C5107.92 (19)C4'—C3'—C2'121.2 (3)
O3—C6—H6A108.7 (13)C4'—C3'—H3'120.7 (19)
O3—C6—H6B108.6 (14)C3'—C4'—H4'122.7 (15)
C5—C6—H6A111.5 (13)C3'—C4'—C5'121.1 (3)
C5—C6—H6B108.9 (13)C5'—C4'—H4'116.1 (15)
H6A—C6—H6B111.2 (19)N1'—C5'—C6'121.5 (2)
O3—C7—C8113.10 (19)C4'—C5'—N1'120.5 (2)
O4—C7—O3122.3 (2)C4'—C5'—C6'118.0 (2)
O4—C7—C8124.6 (2)C1'—C6'—C5'121.0 (2)
C9—C8—C7117.7 (2)C1'—C6'—H6'121.5 (13)
C13—C8—C7123.3 (2)C5'—C6'—H6'117.4 (13)
C13—C8—C9119.0 (2)
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–salicylic acid (1/1) (bzmdslc) top
Crystal data top
C13H13N3O4·C7H6O3F(000) = 864
Mr = 413.38Dx = 1.382 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.5055 (6) ÅCell parameters from 9833 reflections
b = 31.2239 (19) Åθ = 2.6–27.4°
c = 6.8578 (4) ŵ = 0.11 mm1
β = 102.628 (2)°T = 301 K
V = 1986.2 (2) Å3Prismatic, colourless
Z = 40.68 × 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 monochromatorRint = 0.035
φ and ω scansθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1212
Tmin = 0.706, Tmax = 0.746k = 4040
69959 measured reflectionsl = 88
4553 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042All H-atom parameters refined
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0521P)2 + 0.3493P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
4553 reflectionsΔρmax = 0.17 e Å3
347 parametersΔρmin = 0.20 e Å3
100 restraints
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 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
xyzUiso*/Ueq
O10.87803 (16)0.63094 (4)0.3909 (2)0.0887 (4)
O20.92555 (13)0.66308 (4)0.67677 (19)0.0803 (3)
O30.56700 (10)0.71973 (3)0.84768 (15)0.0583 (2)
O40.64060 (13)0.78754 (3)0.84757 (19)0.0771 (3)
N10.66295 (11)0.63293 (3)0.75126 (15)0.0468 (2)
N20.52072 (13)0.58617 (4)0.56128 (18)0.0598 (3)
N30.84921 (13)0.64050 (4)0.55066 (19)0.0603 (3)
C10.54094 (14)0.60942 (4)0.7272 (2)0.0536 (3)
C20.63221 (16)0.59466 (4)0.4743 (2)0.0564 (3)
H20.6423 (17)0.5809 (6)0.355 (3)0.073 (5)*
C30.71994 (14)0.62349 (4)0.58763 (18)0.0480 (3)
C40.4412 (2)0.60928 (8)0.8662 (4)0.0823 (5)
H4A0.478 (3)0.5934 (11)0.988 (5)0.159 (11)*
H4B0.427 (3)0.6365 (9)0.916 (4)0.135 (10)*
H4C0.360 (4)0.5953 (10)0.805 (5)0.156 (11)*
C50.72381 (16)0.65981 (5)0.92458 (19)0.0558 (3)
H5A0.8236 (17)0.6512 (5)0.969 (2)0.058 (4)*
H5B0.6706 (17)0.6528 (5)1.028 (2)0.064 (4)*
C60.71571 (16)0.70700 (5)0.8807 (2)0.0588 (3)
H6A0.7540 (17)0.7136 (5)0.761 (3)0.068 (4)*
C70.54390 (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'A0.0427 (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)*
C90.28162 (16)0.74263 (5)0.7797 (2)0.0616 (3)
C100.1392 (2)0.75472 (7)0.7613 (3)0.0787 (5)
C110.1046 (2)0.79697 (7)0.7762 (3)0.0899 (6)
C120.2100 (3)0.82743 (7)0.8071 (3)0.0932 (6)
C130.3531 (2)0.81613 (5)0.8229 (2)0.0733 (4)
C80.38974 (16)0.77321 (4)0.81035 (17)0.0544 (3)
H6B0.7712 (18)0.7223 (5)0.994 (3)0.069 (4)*
H130.4267 (19)0.8361 (6)0.839 (3)0.072 (5)*
H90.3077 (18)0.7123 (5)0.771 (2)0.070 (5)*
H120.190 (3)0.8559 (8)0.811 (4)0.123 (8)*
H100.062 (3)0.7333 (8)0.741 (3)0.112 (7)*
H110.000 (3)0.8054 (7)0.766 (3)0.116 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1115 (10)0.0842 (8)0.0896 (8)0.0158 (7)0.0642 (8)0.0120 (6)
O20.0697 (7)0.0785 (7)0.0976 (8)0.0226 (6)0.0291 (6)0.0181 (6)
O30.0585 (5)0.0463 (5)0.0674 (6)0.0003 (4)0.0077 (4)0.0079 (4)
O40.0822 (7)0.0528 (6)0.0979 (8)0.0125 (5)0.0230 (6)0.0080 (5)
N10.0541 (6)0.0414 (5)0.0460 (5)0.0006 (4)0.0134 (4)0.0012 (4)
N20.0613 (7)0.0471 (6)0.0695 (7)0.0066 (5)0.0107 (5)0.0016 (5)
N30.0680 (7)0.0500 (6)0.0698 (7)0.0058 (5)0.0300 (6)0.0020 (5)
C10.0541 (7)0.0466 (6)0.0614 (7)0.0008 (5)0.0157 (6)0.0071 (5)
C20.0697 (8)0.0442 (6)0.0557 (7)0.0018 (6)0.0148 (6)0.0039 (5)
C30.0566 (7)0.0405 (6)0.0496 (6)0.0001 (5)0.0174 (5)0.0016 (5)
C40.0773 (12)0.0870 (13)0.0938 (13)0.0075 (10)0.0428 (10)0.0071 (11)
C50.0621 (8)0.0579 (8)0.0451 (6)0.0046 (6)0.0070 (6)0.0045 (5)
C60.0568 (7)0.0531 (7)0.0638 (8)0.0014 (6)0.0072 (6)0.0134 (6)
C70.0714 (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)
C90.0675 (8)0.0617 (8)0.0529 (7)0.0029 (7)0.0076 (6)0.0094 (6)
C100.0697 (10)0.0947 (13)0.0667 (9)0.0059 (9)0.0041 (8)0.0144 (8)
C110.0814 (12)0.1051 (15)0.0744 (11)0.0296 (11)0.0021 (9)0.0137 (10)
C120.1147 (16)0.0723 (11)0.0852 (12)0.0411 (11)0.0056 (11)0.0024 (9)
C130.0964 (12)0.0533 (8)0.0661 (9)0.0106 (8)0.0089 (8)0.0010 (7)
C80.0739 (8)0.0508 (7)0.0363 (6)0.0074 (6)0.0077 (5)0.0034 (5)
Geometric parameters (Å, º) top
O1—N31.2229 (16)O2'—C7'1.2196 (17)
O2—N31.2236 (16)O3'—H3'0.92 (2)
O3—C61.4378 (17)O3'—C2'1.3507 (17)
O3—C71.3441 (15)C7'—C1'1.4704 (19)
O4—C71.2015 (17)C1'—C2'1.3950 (19)
N1—C11.3518 (16)C1'—C6'1.3953 (19)
N1—C31.3803 (15)C2'—C3'1.391 (2)
N1—C51.4667 (16)C3'—H3'A0.951 (18)
N2—C11.3281 (18)C3'—C4'1.368 (2)
N2—C21.3509 (19)C4'—H4'1.001 (19)
N3—C31.4116 (17)C4'—C5'1.386 (2)
C1—C41.484 (2)C5'—H5'0.95 (2)
C2—H20.948 (17)C5'—C6'1.374 (2)
C2—C31.3514 (18)C6'—H6'1.019 (17)
C4—H4A0.97 (3)C9—C101.384 (2)
C4—H4B0.94 (3)C9—C81.385 (2)
C4—H4C0.91 (3)C9—H90.984 (17)
C5—H5A0.969 (16)C10—C111.369 (3)
C5—H5B0.980 (16)C10—H100.98 (2)
C5—C61.503 (2)C11—C121.364 (3)
C6—H6A0.988 (17)C11—H111.02 (2)
C6—H6B0.965 (17)C12—C131.386 (3)
C7—C81.478 (2)C12—H120.91 (2)
O1'—H1'0.91 (2)C13—C81.392 (2)
O1'—C7'1.3111 (18)C13—H130.925 (18)
C7—O3—C6115.08 (11)O1'—C7'—C1'114.06 (12)
C1—N1—C3105.29 (10)O2'—C7'—O1'122.59 (14)
C1—N1—C5125.82 (11)O2'—C7'—C1'123.34 (14)
C3—N1—C5128.73 (11)C2'—C1'—C7'120.02 (12)
C1—N2—C2106.89 (11)C2'—C1'—C6'119.06 (12)
O1—N3—O2124.02 (13)C6'—C1'—C7'120.90 (13)
O1—N3—C3116.32 (12)O3'—C2'—C1'122.74 (13)
O2—N3—C3119.66 (12)O3'—C2'—C3'117.89 (14)
N1—C1—C4125.10 (15)C3'—C2'—C1'119.37 (13)
N2—C1—N1111.15 (11)C2'—C3'—H3'A118.1 (11)
N2—C1—C4123.75 (15)C4'—C3'—C2'120.49 (15)
N2—C2—H2122.0 (10)C4'—C3'—H3'A121.4 (11)
N2—C2—C3108.78 (12)C3'—C4'—H4'118.4 (11)
C3—C2—H2129.2 (10)C3'—C4'—C5'120.82 (14)
N1—C3—N3125.27 (11)C5'—C4'—H4'120.7 (11)
C2—C3—N1107.88 (11)C4'—C5'—H5'120.2 (12)
C2—C3—N3126.83 (12)C6'—C5'—C4'119.11 (15)
C1—C4—H4A113.1 (19)C6'—C5'—H5'120.7 (12)
C1—C4—H4B113.2 (17)C1'—C6'—H6'118.1 (9)
C1—C4—H4C107.7 (19)C5'—C6'—C1'121.13 (14)
H4A—C4—H4B102 (2)C5'—C6'—H6'120.8 (9)
H4A—C4—H4C105 (2)C10—C9—C8120.28 (15)
H4B—C4—H4C116 (3)C10—C9—H9120.7 (10)
N1—C5—H5A106.3 (9)C8—C9—H9119.0 (10)
N1—C5—H5B106.4 (9)C9—C10—H10121.0 (14)
N1—C5—C6113.88 (11)C11—C10—C9120.15 (19)
H5A—C5—H5B109.7 (13)C11—C10—H10118.8 (14)
C6—C5—H5A109.7 (9)C10—C11—H11119.4 (13)
C6—C5—H5B110.6 (9)C12—C11—C10120.21 (19)
O3—C6—C5107.94 (12)C12—C11—H11120.3 (13)
O3—C6—H6A109.8 (10)C11—C12—C13120.64 (18)
O3—C6—H6B109.6 (10)C11—C12—H12122.2 (17)
C5—C6—H6A111.0 (9)C13—C12—H12117.1 (17)
C5—C6—H6B109.3 (10)C12—C13—C8119.65 (19)
H6A—C6—H6B109.1 (13)C12—C13—H13122.8 (11)
O3—C7—C8112.36 (11)C8—C13—H13117.5 (11)
O4—C7—O3122.24 (13)C9—C8—C7122.78 (12)
O4—C7—C8125.38 (12)C9—C8—C13119.05 (15)
C7'—O1'—H1'111.8 (14)C13—C8—C7118.15 (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+·C4H3O4F(000) = 1632
Mr = 391.33Dx = 1.447 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 43.130 (3) ÅCell parameters from 6422 reflections
b = 5.7944 (4) Åθ = 2.7–26.1°
c = 15.2645 (11) ŵ = 0.12 mm1
β = 109.600 (3)°T = 302 K
V = 3593.7 (5) Å3Prism, clear light colourless
Z = 80.57 × 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 monochromatorRint = 0.089
φ and ω scansθmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 5649
Tmin = 0.261, Tmax = 0.746k = 77
20803 measured reflectionsl = 1919
4130 independent reflections
Refinement top
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.056 w = 1/[σ2(Fo2) + (0.0536P)2 + 0.8177P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.147(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.18 e Å3
4130 reflectionsΔρmin = 0.21 e Å3
322 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0015 (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.

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
xyzUiso*/Ueq
O30.68004 (4)0.6877 (3)0.23662 (13)0.0507 (5)
O1'0.55288 (4)0.0276 (3)0.21210 (14)0.0618 (6)
O40.66174 (4)0.3229 (3)0.22612 (14)0.0603 (5)
N10.61358 (4)0.6620 (3)0.25880 (13)0.0390 (5)
N20.58882 (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)
O20.65266 (6)0.9311 (4)0.41184 (14)0.0826 (7)
N30.64430 (5)0.7380 (4)0.42711 (17)0.0569 (6)
O10.65247 (6)0.6494 (4)0.50428 (14)0.0831 (7)
C30.62288 (6)0.6050 (4)0.35213 (17)0.0421 (6)
C10.59273 (6)0.4969 (4)0.21254 (17)0.0424 (6)
C80.71780 (6)0.4014 (4)0.31383 (17)0.0434 (6)
C70.68393 (6)0.4588 (4)0.25489 (18)0.0444 (6)
C50.62531 (7)0.8476 (4)0.2115 (2)0.0442 (6)
C20.60735 (6)0.4094 (4)0.3611 (2)0.0491 (7)
C60.64965 (7)0.7620 (5)0.1677 (2)0.0495 (7)
C130.74353 (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)
C90.72408 (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)
C120.77498 (7)0.4969 (5)0.3810 (2)0.0568 (7)
C110.78124 (8)0.2810 (5)0.4226 (2)0.0587 (8)
C100.75578 (8)0.1264 (5)0.4091 (2)0.0585 (8)
C40.57704 (9)0.4779 (6)0.1113 (2)0.0587 (8)
H5A0.6059 (6)0.907 (4)0.1597 (16)0.045 (7)*
H130.7388 (6)0.707 (4)0.2973 (16)0.052 (7)*
H5B0.6357 (5)0.968 (4)0.2571 (16)0.043 (7)*
H6A0.6413 (6)0.631 (5)0.1212 (18)0.063 (8)*
H2'0.5118 (6)0.330 (4)0.1577 (16)0.055 (7)*
H2A0.6072 (6)0.328 (4)0.4128 (17)0.048 (7)*
H120.7929 (7)0.609 (5)0.3919 (18)0.070 (9)*
H6B0.6568 (6)0.893 (5)0.1377 (19)0.067 (8)*
H100.7590 (6)0.031 (5)0.4418 (19)0.073 (9)*
H4A0.5560 (9)0.388 (6)0.096 (2)0.107 (12)*
H4B0.5743 (8)0.625 (6)0.082 (2)0.093 (11)*
H90.7040 (7)0.076 (5)0.3437 (19)0.077 (9)*
H3'A0.4572 (7)0.335 (5)0.0881 (19)0.073 (9)*
H20.5745 (8)0.206 (5)0.255 (2)0.089 (10)*
H110.8042 (7)0.243 (5)0.4636 (19)0.074 (9)*
H4C0.5910 (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
U11U22U33U12U13U23
O30.0424 (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)
O40.0523 (11)0.0405 (10)0.0828 (14)0.0081 (9)0.0158 (10)0.0015 (9)
N10.0381 (11)0.0325 (10)0.0461 (12)0.0026 (9)0.0136 (10)0.0003 (9)
N20.0472 (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)
O20.0995 (17)0.0666 (14)0.0724 (15)0.0391 (13)0.0165 (13)0.0087 (11)
N30.0533 (14)0.0563 (14)0.0560 (16)0.0119 (12)0.0115 (12)0.0057 (12)
O10.0933 (17)0.0892 (16)0.0482 (13)0.0182 (13)0.0010 (12)0.0089 (12)
C30.0391 (14)0.0414 (13)0.0442 (15)0.0025 (11)0.0120 (12)0.0001 (11)
C10.0382 (13)0.0389 (13)0.0495 (16)0.0009 (11)0.0139 (12)0.0009 (12)
C80.0455 (15)0.0389 (13)0.0502 (15)0.0023 (11)0.0217 (13)0.0074 (11)
C70.0493 (16)0.0345 (13)0.0566 (16)0.0036 (12)0.0273 (13)0.0049 (12)
C50.0449 (15)0.0337 (13)0.0541 (17)0.0012 (12)0.0169 (14)0.0069 (13)
C20.0500 (16)0.0452 (15)0.0514 (18)0.0066 (12)0.0163 (14)0.0037 (14)
C60.0489 (16)0.0453 (15)0.0570 (17)0.0004 (13)0.0215 (14)0.0077 (14)
C130.0472 (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)
C90.0582 (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)
C120.0500 (17)0.0546 (17)0.068 (2)0.0046 (15)0.0224 (15)0.0073 (15)
C110.0530 (18)0.0646 (19)0.0543 (18)0.0110 (16)0.0122 (15)0.0082 (15)
C100.071 (2)0.0482 (16)0.0541 (18)0.0090 (16)0.0189 (16)0.0020 (14)
C40.062 (2)0.0612 (19)0.0483 (18)0.0114 (17)0.0126 (16)0.0067 (16)
Geometric parameters (Å, º) top
O3—C71.354 (3)C5—C61.505 (4)
O3—C61.444 (3)C5—H5A1.00 (2)
O1'—C1'1.246 (3)C5—H5B0.98 (2)
O4—C71.202 (3)C2—H2A0.92 (2)
N1—C31.384 (3)C6—H6A1.02 (3)
N1—C11.340 (3)C6—H6B0.99 (3)
N1—C51.476 (3)C13—C121.372 (4)
N2—C11.336 (3)C13—H130.97 (2)
N2—C21.351 (3)C1'—C2'1.488 (3)
N2—H21.00 (3)C2'—C3'1.330 (4)
O3'—C4'1.297 (3)C2'—H2'0.98 (2)
O3'—H3'1.10 (4)C9—C101.379 (4)
O2'—C1'1.259 (3)C9—H91.03 (3)
O2'—H3'1.35 (4)C4'—C3'1.485 (4)
O4'—C4'1.214 (3)C3'—H3'A0.97 (3)
O2—N31.222 (3)C12—C111.388 (4)
N3—O11.223 (3)C12—H120.98 (3)
N3—C31.431 (3)C11—C101.378 (4)
C3—C21.347 (3)C11—H111.00 (3)
C1—C41.469 (4)C10—H101.02 (3)
C8—C71.474 (3)C4—H4A1.00 (4)
C8—C131.390 (3)C4—H4B0.95 (3)
C8—C91.399 (3)C4—H4C0.96 (3)
C7—O3—C6117.5 (2)C5—C6—H6A114.8 (15)
C3—N1—C5130.4 (2)C5—C6—H6B109.1 (15)
C1—N1—C3106.48 (19)H6A—C6—H6B110 (2)
C1—N1—C5122.8 (2)C8—C13—H13118.5 (14)
C1—N2—C2109.8 (2)C12—C13—C8120.4 (3)
C1—N2—H2122.4 (17)C12—C13—H13121.0 (15)
C2—N2—H2127.8 (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—O1124.0 (2)C1'—C2'—H2'111.7 (14)
O2—N3—C3119.5 (2)C3'—C2'—C1'130.4 (3)
O1—N3—C3116.4 (2)C3'—C2'—H2'117.9 (14)
N1—C3—N3125.5 (2)C8—C9—H9116.3 (15)
C2—C3—N1108.8 (2)C10—C9—C8119.2 (3)
C2—C3—N3125.6 (2)C10—C9—H9124.5 (15)
N1—C1—C4126.8 (2)O3'—C4'—C3'119.8 (2)
N2—C1—N1108.6 (2)O4'—C4'—O3'120.3 (3)
N2—C1—C4124.6 (2)O4'—C4'—C3'119.8 (3)
C13—C8—C7121.6 (2)C2'—C3'—C4'130.8 (3)
C13—C8—C9119.6 (3)C2'—C3'—H3'A117.3 (17)
C9—C8—C7118.8 (2)C4'—C3'—H3'A111.9 (17)
O3—C7—C8112.0 (2)C13—C12—C11120.1 (3)
O4—C7—O3122.5 (2)C13—C12—H12119.9 (16)
O4—C7—C8125.4 (2)C11—C12—H12119.9 (16)
N1—C5—C6112.4 (2)C12—C11—H11119.0 (16)
N1—C5—H5A107.7 (13)C10—C11—C12119.6 (3)
N1—C5—H5B108.7 (13)C10—C11—H11121.3 (16)
C6—C5—H5A106.7 (13)C9—C10—H10116.6 (16)
C6—C5—H5B109.2 (13)C11—C10—C9121.0 (3)
H5A—C5—H5B112.1 (18)C11—C10—H10122.3 (15)
N2—C2—H2A121.9 (15)C1—C4—H4A110.6 (19)
C3—C2—N2106.3 (2)C1—C4—H4B111.2 (19)
C3—C2—H2A131.7 (15)C1—C4—H4C110 (2)
O3—C6—C5111.9 (2)H4A—C4—H4B113 (3)
O3—C6—H6A107.9 (15)H4A—C4—H4C106 (3)
O3—C6—H6B102.6 (15)H4B—C4—H4C106 (3)
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–isophthalic acid (1/1) (bzmdiac) top
Crystal data top
C13H13N3O4·C8H6O4F(000) = 920
Mr = 441.39Dx = 1.414 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.8300 (3) ÅCell parameters from 9928 reflections
b = 33.7182 (10) Åθ = 2.4–30.4°
c = 7.3199 (2) ŵ = 0.11 mm1
β = 107.878 (1)°T = 304 K
V = 2074.13 (11) Å3Prism, clear light colourless
Z = 40.95 × 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 monochromatorRint = 0.037
φ and ω scansθmax = 30.5°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 1212
Tmin = 0.649, Tmax = 0.746k = 4848
38842 measured reflectionsl = 1010
6344 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050All H-atom parameters refined
wR(F2) = 0.145 w = 1/[σ2(Fo2) + (0.0601P)2 + 0.4881P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
6344 reflectionsΔρmax = 0.20 e Å3
365 parametersΔρmin = 0.21 e Å3
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 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
xyzUiso*/Ueq
O30.36882 (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)
N10.28442 (13)0.36122 (3)0.03743 (16)0.0452 (3)
O10.12528 (17)0.37021 (4)0.3517 (2)0.0760 (4)
N20.48973 (15)0.39681 (4)0.13450 (19)0.0537 (3)
N30.12377 (16)0.36110 (4)0.1893 (2)0.0550 (3)
O20.01225 (15)0.34423 (5)0.0737 (2)0.0833 (4)
O40.30372 (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)
C30.26003 (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)
C80.56805 (17)0.23453 (4)0.1057 (2)0.0491 (3)
C10.42668 (17)0.37765 (4)0.0295 (2)0.0507 (3)
C20.38648 (18)0.39278 (4)0.2375 (2)0.0509 (3)
C70.40177 (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)
C50.18737 (19)0.33572 (5)0.1921 (2)0.0544 (3)
C2'0.97138 (19)0.44485 (5)0.8302 (2)0.0552 (3)
C60.20736 (17)0.29250 (5)0.1403 (3)0.0539 (4)
C90.67651 (18)0.26461 (5)0.0982 (3)0.0578 (4)
C3'1.1133 (2)0.45954 (5)0.9526 (2)0.0585 (4)
C100.8293 (2)0.25530 (6)0.0977 (3)0.0664 (4)
C110.8741 (2)0.21669 (6)0.1068 (3)0.0664 (4)
C130.6152 (2)0.19536 (5)0.1115 (3)0.0669 (4)
C120.7681 (2)0.18670 (6)0.1130 (3)0.0739 (5)
C40.4995 (3)0.37538 (8)0.1860 (4)0.0781 (6)
H6'1.0525 (19)0.4509 (5)0.425 (2)0.049 (4)*
H5A0.219 (2)0.3419 (5)0.307 (3)0.059 (5)*
H5B0.077 (2)0.3443 (5)0.217 (3)0.060 (5)*
H6A0.138 (2)0.2775 (5)0.242 (3)0.062 (5)*
H20.405 (2)0.4048 (6)0.365 (3)0.066 (5)*
H4'1.335 (2)0.4810 (5)0.964 (3)0.059 (5)*
H6B0.187 (2)0.2868 (5)0.018 (3)0.060 (5)*
H3'A1.128 (2)0.4626 (6)1.089 (3)0.072 (5)*
H90.645 (2)0.2931 (6)0.091 (3)0.076 (6)*
H130.538 (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)*
H110.983 (3)0.2095 (6)0.109 (3)0.084 (6)*
H100.906 (3)0.2768 (6)0.092 (3)0.080 (6)*
H120.796 (3)0.1580 (7)0.126 (3)0.091 (7)*
H4A0.493 (4)0.3484 (12)0.248 (5)0.150 (12)*
H4B0.598 (5)0.3788 (12)0.136 (5)0.154 (14)*
H3'1.543 (4)0.5032 (9)0.655 (4)0.125 (9)*
H4C0.469 (5)0.3945 (12)0.266 (6)0.163 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0382 (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)
N10.0418 (5)0.0493 (6)0.0435 (6)0.0070 (5)0.0115 (4)0.0015 (5)
O10.0815 (9)0.0851 (9)0.0766 (8)0.0039 (7)0.0465 (7)0.0137 (7)
N20.0459 (6)0.0519 (7)0.0593 (7)0.0118 (5)0.0102 (5)0.0050 (5)
N30.0505 (7)0.0522 (7)0.0681 (8)0.0035 (5)0.0269 (6)0.0042 (6)
O20.0555 (7)0.1038 (10)0.0973 (10)0.0306 (7)0.0334 (7)0.0289 (8)
O40.0567 (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)
C30.0405 (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)
C80.0444 (7)0.0548 (8)0.0476 (7)0.0079 (6)0.0135 (6)0.0088 (6)
C10.0459 (7)0.0529 (8)0.0538 (8)0.0077 (6)0.0162 (6)0.0088 (6)
C20.0500 (7)0.0476 (7)0.0517 (8)0.0063 (6)0.0104 (6)0.0012 (6)
C70.0454 (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)
C50.0444 (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)
C60.0353 (6)0.0627 (9)0.0614 (9)0.0116 (6)0.0115 (6)0.0147 (7)
C90.0441 (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)
C100.0454 (8)0.0737 (11)0.0820 (12)0.0092 (8)0.0224 (8)0.0097 (9)
C110.0487 (8)0.0821 (12)0.0681 (10)0.0060 (8)0.0177 (8)0.0065 (9)
C130.0632 (10)0.0555 (9)0.0840 (12)0.0094 (8)0.0254 (9)0.0075 (8)
C120.0688 (11)0.0645 (11)0.0887 (13)0.0105 (9)0.0250 (10)0.0045 (9)
C40.0825 (15)0.0893 (15)0.0776 (13)0.0158 (12)0.0468 (12)0.0077 (12)
Geometric parameters (Å, º) top
O3—C71.3435 (19)C8—C91.384 (2)
O3—C61.4388 (17)C8—C131.389 (2)
O4'—C8'1.2338 (18)C1—C41.478 (3)
O1'—C7'1.3101 (19)C2—H20.983 (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—C61.502 (2)
N1—C31.3829 (18)C5—H5A0.989 (18)
N1—C11.3578 (17)C5—H5B0.976 (18)
N1—C51.4694 (18)C2'—C3'1.389 (2)
O1—N31.2243 (18)C2'—H2'1.03 (2)
N2—C11.326 (2)C6—H6A0.952 (19)
N2—C21.357 (2)C6—H6B0.988 (18)
N3—O21.2236 (18)C9—C101.384 (2)
N3—C31.4171 (18)C9—H91.01 (2)
O4—C71.2019 (18)C3'—H3'A0.97 (2)
O2'—C7'1.1986 (19)C10—C111.368 (3)
C6'—C5'1.3953 (18)C10—H100.98 (2)
C6'—C1'1.3821 (19)C11—C121.369 (3)
C6'—H6'0.968 (16)C11—H111.00 (2)
C5'—C8'1.479 (2)C13—C121.385 (3)
C5'—C4'1.386 (2)C13—H130.94 (2)
C3—C21.3564 (19)C12—H121.01 (2)
C1'—C7'1.4955 (19)C4—H4A1.01 (4)
C1'—C2'1.389 (2)C4—H4B0.84 (4)
C8—C71.481 (2)C4—H4C0.86 (4)
C7—O3—C6116.03 (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—C6112.20 (13)
C3—N1—C5128.58 (12)N1—C5—H5A106.5 (10)
C1—N1—C3105.42 (11)N1—C5—H5B106.3 (10)
C1—N1—C5125.80 (13)C6—C5—H5A112.2 (10)
C1—N2—C2106.69 (12)C6—C5—H5B111.5 (10)
O1—N3—C3117.19 (13)H5A—C5—H5B107.7 (15)
O2—N3—O1123.67 (14)C1'—C2'—H2'120.0 (11)
O2—N3—C3119.14 (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—C5107.41 (12)
C1'—C6'—H6'118.5 (10)O3—C6—H6A108.6 (11)
C6'—C5'—C8'118.94 (12)O3—C6—H6B109.3 (11)
C4'—C5'—C6'120.14 (13)C5—C6—H6A108.8 (11)
C4'—C5'—C8'120.90 (12)C5—C6—H6B112.1 (10)
N1—C3—N3125.76 (12)H6A—C6—H6B110.6 (15)
C2—C3—N1107.51 (12)C8—C9—H9120.0 (12)
C2—C3—N3126.67 (13)C10—C9—C8119.72 (16)
O4'—C8'—O3'122.69 (14)C10—C9—H9120.3 (12)
O4'—C8'—C5'121.51 (12)C4'—C3'—C2'119.96 (15)
O3'—C8'—C5'115.80 (13)C4'—C3'—H3'A119.1 (12)
C6'—C1'—C7'121.54 (13)C2'—C3'—H3'A120.9 (12)
C6'—C1'—C2'120.17 (13)C9—C10—H10119.3 (13)
C2'—C1'—C7'118.26 (13)C11—C10—C9120.78 (17)
C9—C8—C7121.91 (14)C11—C10—H10119.9 (13)
C9—C8—C13119.19 (15)C10—C11—C12119.97 (17)
C13—C8—C7118.88 (14)C10—C11—H11121.8 (12)
N1—C1—C4124.24 (16)C12—C11—H11118.2 (12)
N2—C1—N1111.31 (13)C8—C13—H13116.8 (13)
N2—C1—C4124.42 (16)C12—C13—C8120.17 (17)
N2—C2—C3109.07 (13)C12—C13—H13123.1 (13)
N2—C2—H2122.9 (11)C11—C12—C13120.15 (18)
C3—C2—H2128.1 (11)C11—C12—H12121.6 (13)
O3—C7—C8112.45 (12)C13—C12—H12118.2 (13)
O4—C7—O3122.45 (14)C1—C4—H4A114.7 (19)
O4—C7—C8125.08 (15)C1—C4—H4B107 (2)
C5'—C4'—H4'118.9 (10)C1—C4—H4C112 (3)
C3'—C4'—C5'120.08 (14)H4A—C4—H4B103 (3)
C3'—C4'—H4'121.1 (10)H4A—C4—H4C114 (3)
O1'—C7'—C1'114.20 (12)H4B—C4—H4C105 (3)
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–resorcinol (2/1) (bzmdres) top
Crystal data top
2C13H13N3O4·C6H6O2Dx = 1.376 Mg m3
Mr = 660.63Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, PbcaCell parameters from 9896 reflections
a = 26.3241 (4) Åθ = 3.1–68.2°
b = 7.1612 (1) ŵ = 0.88 mm1
c = 33.8433 (5) ÅT = 300 K
V = 6379.87 (16) Å3Plate, clear light colourless
Z = 80.25 × 0.12 × 0.11 mm
F(000) = 2768
Data collection top
Bruker APEXII CCD
diffractometer
4816 reflections with I > 2σ(I)
φ and ω scansRint = 0.066
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 68.3°, θmin = 2.6°
Tmin = 0.623, Tmax = 0.753h = 3131
121051 measured reflectionsk = 88
5865 independent reflectionsl = 4040
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.048 w = 1/[σ2(Fo2) + (0.0733P)2 + 1.6636P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.147(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.30 e Å3
5865 reflectionsΔρmin = 0.31 e Å3
540 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.00043 (6)
Primary atom site location: dual
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 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
xyzUiso*/Ueq
O3B0.29177 (5)0.7763 (2)0.21878 (3)0.0676 (3)
O3A0.70575 (5)0.1189 (2)0.52879 (4)0.0691 (3)
N1A0.60485 (5)0.0111 (2)0.55009 (4)0.0594 (4)
N1B0.39439 (5)0.6490 (2)0.19753 (4)0.0606 (4)
O4B0.21161 (6)0.7410 (3)0.19886 (5)0.0946 (5)
N2A0.55969 (6)0.1485 (2)0.50650 (5)0.0698 (4)
O2'0.52718 (8)0.3814 (3)0.44659 (5)0.0978 (5)
O4A0.78574 (6)0.1384 (3)0.55011 (5)0.1011 (6)
N2B0.44240 (6)0.5183 (3)0.24363 (5)0.0721 (4)
O1'0.48855 (7)0.5514 (3)0.31647 (5)0.1049 (6)
O2A0.63071 (7)0.1226 (3)0.62598 (5)0.1110 (6)
N3A0.61124 (7)0.2312 (3)0.60258 (6)0.0859 (5)
C8B0.22773 (7)0.8238 (2)0.26590 (5)0.0603 (4)
O2B0.36980 (8)0.4818 (4)0.12448 (6)0.1210 (7)
N3B0.39162 (7)0.3882 (3)0.14929 (7)0.0919 (6)
C8A0.77042 (7)0.0609 (2)0.48271 (5)0.0616 (4)
C3A0.59504 (6)0.1642 (3)0.56527 (5)0.0629 (4)
O1A0.60434 (8)0.3983 (3)0.60894 (7)0.1274 (8)
C7B0.24133 (7)0.7746 (3)0.22482 (5)0.0637 (4)
C1B0.41703 (7)0.6707 (3)0.23323 (5)0.0633 (4)
C1A0.58274 (7)0.0115 (3)0.51389 (5)0.0647 (4)
C7A0.75635 (7)0.1104 (3)0.52361 (5)0.0660 (5)
C9A0.73439 (8)0.0105 (3)0.45482 (5)0.0644 (4)
C3B0.40651 (6)0.4703 (3)0.18565 (6)0.0661 (5)
C2A0.56744 (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)
C9B0.26411 (8)0.8558 (3)0.29468 (6)0.0689 (5)
C1'0.50863 (8)0.4587 (3)0.38117 (6)0.0741 (5)
C2B0.43581 (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)
C6B0.30779 (8)0.7433 (4)0.17856 (6)0.0731 (5)
C5B0.36357 (8)0.7879 (3)0.17681 (7)0.0741 (5)
C5A0.63229 (9)0.1684 (3)0.56795 (7)0.0777 (6)
C13B0.17693 (8)0.8428 (4)0.27569 (7)0.0797 (6)
C13A0.82152 (8)0.0597 (3)0.47209 (8)0.0801 (6)
C10A0.74957 (10)0.0442 (3)0.41755 (6)0.0790 (6)
C4'0.48680 (8)0.0933 (3)0.36331 (7)0.0780 (5)
C10B0.24940 (10)0.9079 (3)0.33226 (6)0.0824 (6)
C6A0.68875 (9)0.1410 (5)0.56883 (6)0.0838 (7)
C11B0.19922 (10)0.9302 (4)0.34139 (7)0.0853 (6)
O1B0.40194 (8)0.2250 (4)0.14505 (9)0.1469 (10)
C11A0.79998 (11)0.0491 (3)0.40780 (8)0.0891 (7)
C12A0.83596 (10)0.0054 (4)0.43460 (8)0.0919 (7)
C4B0.41432 (9)0.8429 (4)0.25758 (8)0.0914 (7)
H4BA0.4368620.9353050.2468680.137*
H4BB0.4241520.8146140.2842280.137*
H4BC0.3801820.8900620.2573750.137*
C4A0.58372 (10)0.1713 (4)0.48615 (8)0.0960 (7)
H4AA0.6177880.2180470.4840270.144*
H4AB0.5721690.1310420.4606250.144*
H4AC0.5618380.2683380.4957970.144*
C12B0.16312 (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)*
H6BA0.2885 (8)0.827 (3)0.1608 (7)0.077 (6)*
H2A0.5542 (9)0.370 (4)0.5409 (7)0.081 (7)*
H9A0.6979 (8)0.011 (3)0.4627 (6)0.075 (6)*
H1'A0.5167 (8)0.593 (3)0.3891 (7)0.081 (6)*
H13A0.8432 (9)0.106 (3)0.4913 (7)0.082 (7)*
H4'0.4801 (9)0.041 (4)0.3582 (7)0.090 (7)*
H5AA0.6207 (10)0.178 (4)0.5943 (9)0.100 (8)*
H2B0.4502 (9)0.278 (4)0.2145 (7)0.093 (7)*
H9B0.3015 (9)0.846 (3)0.2874 (7)0.090 (7)*
H6BB0.2999 (9)0.602 (4)0.1714 (7)0.092 (7)*
H6AA0.7045 (10)0.250 (4)0.5801 (8)0.103 (8)*
H5BA0.3718 (9)0.909 (3)0.1898 (7)0.084 (7)*
H11B0.1864 (9)0.985 (4)0.3692 (8)0.098 (7)*
H6AB0.6966 (11)0.033 (4)0.5822 (9)0.103 (9)*
H13B0.1530 (10)0.809 (4)0.2561 (8)0.105 (8)*
H5BB0.3746 (9)0.788 (3)0.1508 (8)0.093 (7)*
H5AB0.6241 (9)0.280 (4)0.5517 (7)0.086 (7)*
H11A0.8124 (10)0.095 (4)0.3826 (9)0.110 (9)*
H10A0.7236 (10)0.082 (4)0.3987 (8)0.103 (8)*
H10B0.2797 (12)0.934 (4)0.3530 (9)0.127 (10)*
H12B0.1301 (11)0.918 (4)0.3203 (8)0.109 (9)*
H12A0.8730 (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
U11U22U33U12U13U23
O3B0.0638 (7)0.0860 (9)0.0530 (6)0.0111 (6)0.0044 (5)0.0048 (6)
O3A0.0637 (7)0.0888 (9)0.0549 (7)0.0131 (6)0.0043 (5)0.0036 (6)
N1A0.0560 (7)0.0656 (8)0.0567 (8)0.0012 (6)0.0005 (6)0.0059 (7)
N1B0.0565 (8)0.0702 (9)0.0550 (8)0.0013 (7)0.0003 (6)0.0026 (7)
O4B0.0744 (9)0.1351 (14)0.0744 (9)0.0050 (9)0.0176 (7)0.0187 (9)
N2A0.0701 (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)
O4A0.0755 (9)0.1502 (16)0.0777 (10)0.0214 (10)0.0196 (8)0.0123 (10)
N2B0.0614 (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)
O2A0.0989 (12)0.1692 (19)0.0649 (9)0.0149 (12)0.0146 (8)0.0071 (11)
N3A0.0617 (9)0.1170 (16)0.0789 (11)0.0060 (10)0.0095 (8)0.0261 (12)
C8B0.0630 (9)0.0559 (9)0.0620 (9)0.0073 (7)0.0047 (7)0.0082 (8)
O2B0.1083 (13)0.177 (2)0.0778 (10)0.0200 (14)0.0198 (10)0.0295 (12)
N3B0.0644 (10)0.1138 (16)0.0974 (14)0.0070 (10)0.0029 (10)0.0408 (13)
C8A0.0653 (10)0.0546 (9)0.0650 (10)0.0009 (7)0.0032 (8)0.0134 (8)
C3A0.0531 (9)0.0731 (11)0.0626 (10)0.0047 (8)0.0008 (7)0.0051 (8)
O1A0.1041 (13)0.1358 (17)0.1422 (18)0.0224 (12)0.0328 (12)0.0735 (15)
C7B0.0642 (10)0.0633 (10)0.0637 (10)0.0086 (8)0.0112 (8)0.0031 (8)
C1B0.0574 (9)0.0748 (11)0.0578 (9)0.0063 (8)0.0001 (7)0.0008 (8)
C1A0.0600 (9)0.0712 (11)0.0631 (10)0.0022 (8)0.0023 (8)0.0012 (9)
C7A0.0638 (10)0.0679 (11)0.0663 (10)0.0121 (8)0.0102 (8)0.0054 (9)
C9A0.0735 (11)0.0595 (10)0.0603 (10)0.0014 (9)0.0032 (8)0.0057 (8)
C3B0.0542 (9)0.0754 (12)0.0686 (11)0.0017 (8)0.0020 (8)0.0090 (9)
C2A0.0649 (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)
C9B0.0677 (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)
C2B0.0590 (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)
C6B0.0735 (11)0.0950 (15)0.0507 (9)0.0169 (11)0.0042 (8)0.0097 (10)
C5B0.0786 (12)0.0832 (14)0.0604 (11)0.0058 (10)0.0039 (9)0.0183 (10)
C5A0.0805 (13)0.0806 (14)0.0720 (13)0.0147 (11)0.0060 (10)0.0226 (11)
C13B0.0654 (11)0.0961 (15)0.0777 (13)0.0082 (11)0.0049 (10)0.0039 (11)
C13A0.0679 (11)0.0853 (14)0.0870 (15)0.0032 (10)0.0037 (11)0.0200 (12)
C10A0.1019 (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)
C10B0.0908 (14)0.0944 (15)0.0621 (11)0.0141 (12)0.0076 (11)0.0014 (10)
C6A0.0753 (13)0.118 (2)0.0580 (11)0.0275 (13)0.0007 (9)0.0181 (13)
C11B0.0988 (16)0.0913 (15)0.0657 (12)0.0218 (12)0.0088 (11)0.0113 (11)
O1B0.1119 (15)0.1435 (19)0.185 (2)0.0282 (14)0.0336 (15)0.0900 (18)
C11A0.1141 (19)0.0790 (14)0.0743 (14)0.0256 (13)0.0189 (14)0.0207 (11)
C12A0.0846 (15)0.0949 (16)0.0961 (17)0.0210 (13)0.0233 (14)0.0306 (14)
C4B0.0849 (14)0.0990 (16)0.0902 (15)0.0038 (12)0.0086 (12)0.0245 (13)
C4A0.0959 (16)0.0983 (17)0.0939 (16)0.0162 (13)0.0162 (13)0.0305 (14)
C12B0.0744 (13)0.1126 (19)0.0853 (15)0.0143 (13)0.0163 (12)0.0081 (13)
Geometric parameters (Å, º) top
O3B—C7B1.344 (2)N3B—C3B1.419 (3)
O3B—C6B1.444 (2)N3B—O1B1.208 (3)
O3A—C7A1.345 (2)C8A—C7A1.476 (3)
O3A—C6A1.436 (2)C8A—C9A1.386 (3)
N1A—C3A1.381 (2)C8A—C13A1.392 (3)
N1A—C1A1.356 (2)C3A—C2A1.344 (3)
N1A—C5A1.468 (2)C1B—C4B1.485 (3)
N1B—C1B1.356 (2)C1A—C4A1.480 (3)
N1B—C3B1.379 (3)C9A—C10A1.380 (3)
N1B—C5B1.462 (3)C3B—C2B1.344 (3)
O4B—C7B1.201 (2)C6'—C1'1.378 (3)
N2A—C1A1.321 (3)C6'—C5'1.382 (3)
N2A—C2A1.348 (3)C2'—C1'1.390 (3)
O2'—C6'1.367 (3)C2'—C3'1.376 (3)
O4A—C7A1.201 (2)C9B—C10B1.381 (3)
N2B—C1B1.327 (3)C3'—C4'1.381 (3)
N2B—C2B1.350 (3)C5'—C4'1.378 (3)
O1'—C2'1.366 (3)C6B—C5B1.504 (3)
O2A—N3A1.223 (3)C5A—C6A1.500 (3)
N3A—C3A1.417 (3)C13B—C12B1.376 (3)
N3A—O1A1.229 (3)C13A—C12A1.380 (4)
C8B—C7B1.478 (3)C10A—C11A1.368 (4)
C8B—C9B1.385 (3)C10B—C11B1.366 (3)
C8B—C13B1.384 (3)C11B—C12B1.367 (4)
O2B—N3B1.218 (3)C11A—C12A1.368 (4)
C7B—O3B—C6B115.49 (14)N2A—C1A—C4A123.95 (18)
C7A—O3A—C6A115.89 (15)O3A—C7A—C8A112.42 (15)
C3A—N1A—C5A129.51 (17)O4A—C7A—O3A122.22 (19)
C1A—N1A—C3A104.96 (15)O4A—C7A—C8A125.35 (19)
C1A—N1A—C5A125.52 (18)C10A—C9A—C8A119.9 (2)
C1B—N1B—C3B105.33 (15)N1B—C3B—N3B125.01 (19)
C1B—N1B—C5B126.37 (17)C2B—C3B—N1B107.44 (18)
C3B—N1B—C5B128.30 (17)C2B—C3B—N3B127.5 (2)
C1A—N2A—C2A106.47 (16)C3A—C2A—N2A109.46 (18)
C1B—N2B—C2B106.10 (16)O2'—C6'—C1'116.5 (2)
O2A—N3A—C3A119.2 (2)O2'—C6'—C5'123.01 (18)
O2A—N3A—O1A124.6 (2)C1'—C6'—C5'120.5 (2)
O1A—N3A—C3A116.2 (2)O1'—C2'—C1'116.9 (2)
C9B—C8B—C7B122.23 (17)O1'—C2'—C3'122.55 (19)
C13B—C8B—C7B118.84 (17)C3'—C2'—C1'120.55 (19)
C13B—C8B—C9B118.91 (19)C10B—C9B—C8B119.90 (19)
O2B—N3B—C3B120.0 (2)C6'—C1'—C2'119.7 (2)
O1B—N3B—O2B123.8 (2)C3B—C2B—N2B109.83 (19)
O1B—N3B—C3B116.2 (2)C2'—C3'—C4'118.7 (2)
C9A—C8A—C7A121.98 (17)C4'—C5'—C6'118.9 (2)
C9A—C8A—C13A118.92 (19)O3B—C6B—C5B106.70 (17)
C13A—C8A—C7A119.07 (18)N1B—C5B—C6B112.24 (17)
N1A—C3A—N3A125.69 (18)N1A—C5A—C6A113.3 (2)
C2A—C3A—N1A107.63 (17)C12B—C13B—C8B120.2 (2)
C2A—C3A—N3A126.7 (2)C12A—C13A—C8A120.3 (2)
O3B—C7B—C8B112.35 (15)C11A—C10A—C9A120.6 (2)
O4B—C7B—O3B122.31 (18)C5'—C4'—C3'121.7 (2)
O4B—C7B—C8B125.32 (18)C11B—C10B—C9B120.7 (2)
N1B—C1B—C4B124.64 (18)O3A—C6A—C5A107.72 (18)
N2B—C1B—N1B111.30 (17)C10B—C11B—C12B119.6 (2)
N2B—C1B—C4B124.06 (18)C10A—C11A—C12A120.3 (2)
N1A—C1A—C4A124.57 (18)C11A—C12A—C13A119.9 (2)
N2A—C1A—N1A111.47 (17)C11B—C12B—C13B120.6 (2)
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–fumaric acid (2/1) (bzmdfma) top
Crystal data top
C13H13N3O4·0.5C4H4O4F(000) = 696
Mr = 333.30Dx = 1.369 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.0358 (5) ÅCell parameters from 9988 reflections
b = 26.6419 (14) Åθ = 2.3–28.9°
c = 6.8796 (3) ŵ = 0.11 mm1
β = 102.419 (2)°T = 300 K
V = 1617.38 (14) Å3Prism, clear light colourless
Z = 40.63 × 0.17 × 0.17 mm
Data collection top
Bruker APEXII CCD
diffractometer
2625 reflections with I > 2σ(I)
φ and ω scansRint = 0.066
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 27.5°, θmin = 2.8°
Tmin = 0.620, Tmax = 0.746h = 1111
46849 measured reflectionsk = 3434
3705 independent reflectionsl = 88
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.051 w = 1/[σ2(Fo2) + (0.0568P)2 + 0.5999P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.151(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.39 e Å3
3705 reflectionsΔρmin = 0.33 e Å3
267 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.018 (3)
Primary atom site location: dual
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 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
xyzUiso*/Ueq
O10.8887 (3)0.59652 (9)0.3299 (4)0.1261 (9)
O20.9417 (2)0.62892 (9)0.6242 (4)0.1134 (8)
O30.55707 (16)0.70919 (5)0.7641 (2)0.0614 (4)
O40.6408 (2)0.78808 (6)0.7663 (3)0.0818 (5)
N10.64502 (18)0.60717 (6)0.6676 (2)0.0535 (4)
N20.4807 (2)0.56134 (6)0.4570 (3)0.0640 (5)
N30.8562 (3)0.60697 (8)0.4893 (4)0.0820 (6)
C10.5053 (2)0.58656 (7)0.6269 (3)0.0574 (5)
C20.6064 (3)0.56549 (8)0.3829 (4)0.0649 (6)
H20.620 (3)0.5508 (9)0.262 (4)0.078 (7)*
C30.7094 (2)0.59375 (7)0.5099 (3)0.0575 (5)
C40.3945 (3)0.59055 (10)0.7556 (4)0.0838 (7)
H4A0.4177880.5660960.8601830.126*
H4B0.2944080.5845670.6778070.126*
H4C0.3992750.6235760.8123680.126*
C50.7116 (3)0.63718 (9)0.8440 (3)0.0633 (5)
H5A0.650 (3)0.6299 (9)0.940 (4)0.069 (6)*
H5B0.815 (3)0.6255 (9)0.896 (3)0.073 (7)*
C60.7118 (2)0.69224 (9)0.7997 (4)0.0651 (6)
H6A0.766 (3)0.7091 (9)0.907 (4)0.073 (7)*
H6B0.751 (3)0.6996 (9)0.672 (4)0.075 (7)*
C70.5365 (2)0.75911 (8)0.7537 (3)0.0564 (5)
C80.3754 (2)0.77333 (7)0.7313 (3)0.0540 (5)
C90.2606 (3)0.73811 (9)0.7113 (3)0.0605 (5)
H90.287 (3)0.7036 (10)0.710 (4)0.082 (8)*
C100.1132 (3)0.75312 (10)0.6989 (4)0.0725 (6)
H100.031 (3)0.7287 (10)0.685 (4)0.092 (8)*
C110.0794 (3)0.80314 (11)0.7083 (4)0.0807 (7)
H110.026 (3)0.8135 (10)0.702 (4)0.087 (8)*
C120.1916 (4)0.83847 (11)0.7265 (4)0.0856 (8)
H120.163 (3)0.8738 (12)0.734 (4)0.101 (9)*
C130.3391 (3)0.82380 (9)0.7366 (4)0.0717 (6)
H130.421 (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
U11U22U33U12U13U23
O10.1359 (19)0.1154 (17)0.157 (2)0.0397 (14)0.0970 (17)0.0559 (15)
O20.0673 (12)0.1338 (18)0.1422 (19)0.0313 (12)0.0291 (12)0.0469 (15)
O30.0542 (8)0.0556 (8)0.0704 (9)0.0035 (6)0.0045 (6)0.0106 (6)
O40.0761 (11)0.0657 (10)0.1059 (13)0.0188 (8)0.0246 (9)0.0086 (9)
N10.0530 (9)0.0500 (9)0.0554 (9)0.0022 (7)0.0070 (7)0.0012 (7)
N20.0587 (11)0.0481 (9)0.0776 (12)0.0030 (7)0.0020 (9)0.0004 (8)
N30.0767 (14)0.0666 (12)0.1122 (17)0.0152 (10)0.0416 (13)0.0255 (11)
C10.0508 (11)0.0476 (10)0.0712 (13)0.0010 (8)0.0070 (9)0.0084 (9)
C20.0772 (15)0.0472 (11)0.0676 (13)0.0024 (10)0.0094 (11)0.0061 (9)
C30.0590 (12)0.0471 (10)0.0667 (12)0.0040 (8)0.0147 (9)0.0041 (9)
C40.0685 (15)0.0803 (16)0.109 (2)0.0047 (12)0.0329 (14)0.0080 (14)
C50.0616 (13)0.0701 (14)0.0529 (11)0.0021 (10)0.0008 (10)0.0056 (10)
C60.0532 (12)0.0675 (13)0.0686 (14)0.0051 (10)0.0000 (10)0.0185 (11)
C70.0679 (13)0.0558 (11)0.0450 (10)0.0084 (9)0.0112 (9)0.0079 (8)
C80.0648 (12)0.0562 (11)0.0385 (9)0.0020 (9)0.0058 (8)0.0047 (8)
C90.0643 (13)0.0598 (13)0.0535 (11)0.0015 (10)0.0042 (9)0.0051 (9)
C100.0626 (14)0.0813 (16)0.0685 (14)0.0029 (12)0.0027 (11)0.0098 (12)
C110.0717 (17)0.0923 (19)0.0706 (15)0.0176 (15)0.0017 (12)0.0112 (13)
C120.092 (2)0.0672 (16)0.0907 (18)0.0186 (14)0.0038 (14)0.0066 (13)
C130.0855 (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—N31.227 (3)C6—H6A0.91 (3)
O2—N31.221 (3)C6—H6B1.03 (3)
O3—C61.439 (3)C7—C81.480 (3)
O3—C71.343 (2)C8—C91.383 (3)
O4—C71.206 (2)C8—C131.386 (3)
N1—C11.350 (3)C9—H90.95 (3)
N1—C31.384 (3)C9—C101.375 (3)
N1—C51.469 (3)C10—H100.98 (3)
N2—C11.325 (3)C10—C111.372 (4)
N2—C21.346 (3)C11—H110.98 (3)
N3—C31.408 (3)C11—C121.369 (4)
C1—C41.475 (3)C12—H120.98 (3)
C2—H20.95 (2)C12—C131.376 (4)
C2—C31.359 (3)C13—H130.96 (3)
C4—H4A0.9600O1'—H1'1.00 (4)
C4—H4B0.9600O1'—C1'1.308 (3)
C4—H4C0.9600O2'—C1'1.195 (2)
C5—H5A0.97 (2)C1'—C2'1.492 (3)
C5—H5B0.98 (3)C2'—C2'i1.290 (4)
C5—C61.498 (3)C2'—H2'0.96 (3)
C7—O3—C6115.97 (16)C5—C6—H6A110.0 (15)
C1—N1—C3105.33 (17)C5—C6—H6B112.0 (13)
C1—N1—C5126.25 (19)H6A—C6—H6B112 (2)
C3—N1—C5128.42 (18)O3—C7—C8112.38 (17)
C1—N2—C2107.32 (18)O4—C7—O3122.2 (2)
O1—N3—C3116.4 (2)O4—C7—C8125.4 (2)
O2—N3—O1123.6 (2)C9—C8—C7122.44 (19)
O2—N3—C3119.9 (2)C9—C8—C13118.9 (2)
N1—C1—C4124.8 (2)C13—C8—C7118.6 (2)
N2—C1—N1111.17 (19)C8—C9—H9118.1 (16)
N2—C1—C4124.0 (2)C10—C9—C8120.3 (2)
N2—C2—H2125.0 (15)C10—C9—H9121.5 (16)
N2—C2—C3108.6 (2)C9—C10—H10121.3 (16)
C3—C2—H2126.4 (15)C11—C10—C9120.1 (3)
N1—C3—N3125.29 (19)C11—C10—H10118.5 (16)
C2—C3—N1107.59 (19)C10—C11—H11119.7 (16)
C2—C3—N3127.1 (2)C12—C11—C10120.3 (3)
C1—C4—H4A109.5C12—C11—H11120.0 (16)
C1—C4—H4B109.5C11—C12—H12117.6 (17)
C1—C4—H4C109.5C11—C12—C13120.0 (3)
H4A—C4—H4B109.5C13—C12—H12122.4 (17)
H4A—C4—H4C109.5C8—C13—H13116.6 (17)
H4B—C4—H4C109.5C12—C13—C8120.4 (2)
N1—C5—H5A105.1 (14)C12—C13—H13123.0 (17)
N1—C5—H5B108.7 (14)C1'—O1'—H1'112.7 (19)
N1—C5—C6112.52 (18)O1'—C1'—C2'113.71 (19)
H5A—C5—H5B109.2 (19)O2'—C1'—O1'124.1 (2)
C6—C5—H5A111.0 (14)O2'—C1'—C2'122.2 (2)
C6—C5—H5B110.2 (14)C1'—C2'—H2'118.3 (17)
O3—C6—C5107.36 (19)C2'i—C2'—C1'124.3 (3)
O3—C6—H6A108.5 (15)C2'i—C2'—H2'117.3 (17)
O3—C6—H6B107.2 (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·C3H2O4Dx = 1.367 Mg m3
Mr = 652.57Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, PbcnCell parameters from 9937 reflections
a = 26.1542 (4) Åθ = 3.1–72.5°
b = 7.2708 (1) ŵ = 0.92 mm1
c = 16.6719 (3) ÅT = 300 K
V = 3170.36 (9) Å3Prism, clear light colourless
Z = 40.46 × 0.29 × 0.13 mm
F(000) = 1360
Data collection top
Bruker APEXII CCD
diffractometer
2423 reflections with I > 2σ(I)
φ and ω scansRint = 0.038
Absorption correction: numerical
(SADABS; Bruker, 2016)
θmax = 68.2°, θmin = 5.6°
Tmin = 0.736, Tmax = 0.907h = 3131
54755 measured reflectionsk = 88
2893 independent reflectionsl = 2020
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.078 w = 1/[σ2(Fo2) + (0.1596P)2 + 0.3629P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.268(Δ/σ)max = 0.001
S = 1.13Δρmax = 0.33 e Å3
2893 reflectionsΔρmin = 0.27 e Å3
244 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
36 restraintsExtinction coefficient: 0.0039 (11)
Primary atom site location: dual
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 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
xyzUiso*/UeqOcc. (<1)
O30.29519 (7)0.6661 (3)0.53894 (10)0.1002 (6)
O40.21543 (9)0.6847 (4)0.58610 (14)0.1407 (10)
N10.39769 (8)0.5613 (3)0.58207 (13)0.0982 (6)
C70.24416 (10)0.6583 (4)0.53037 (16)0.0976 (7)
N20.44070 (10)0.3861 (5)0.49826 (17)0.1221 (9)
C130.26247 (11)0.5592 (3)0.39102 (16)0.0990 (7)
H130.2972800.5575120.4023890.119*
N30.39562 (11)0.3512 (5)0.7007 (2)0.1341 (10)
C80.22811 (9)0.6113 (3)0.44877 (16)0.0912 (7)
O10.36955 (13)0.4498 (6)0.73879 (15)0.1791 (15)
C60.31291 (13)0.6898 (5)0.61932 (18)0.1201 (10)
H6A0.3049060.5817140.6510650.144*
H6B0.2964350.7953890.6437180.144*
C50.36982 (14)0.7184 (5)0.6162 (2)0.1214 (10)
H5A0.3770220.8269140.5842940.146*
H5B0.3822820.7410230.6700870.146*
C10.41726 (10)0.5501 (5)0.50779 (16)0.1076 (9)
C20.43619 (11)0.2967 (5)0.5682 (2)0.1165 (9)
H20.4494680.1806690.5790410.140*
C120.24521 (15)0.5095 (5)0.31615 (19)0.1220 (10)
H120.2687780.4749980.2771710.146*
C90.17676 (12)0.6158 (5)0.4293 (2)0.1239 (10)
H90.1527660.6530220.4671730.149*
O20.41029 (16)0.2059 (6)0.7247 (3)0.2129 (19)
C30.40976 (10)0.3995 (4)0.61981 (18)0.1060 (8)
C100.16136 (17)0.5646 (7)0.3534 (3)0.1490 (15)
H100.1267980.5683990.3403650.179*
C110.1952 (2)0.5094 (6)0.2979 (2)0.1391 (13)
H110.1841410.4715930.2475150.167*
C40.41453 (17)0.6957 (7)0.4471 (3)0.1555 (16)
H4A0.3803680.7438040.4450260.233*
H4B0.4235540.6461430.3956510.233*
H4C0.4378690.7925780.4609140.233*
O1'0.4899 (3)0.1937 (13)0.3802 (4)0.138 (3)0.5
H1'0.4623760.1713520.4017290.207*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
C2'0.5000000.1017 (7)0.2500000.1213 (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"0.4502970.3179070.3881540.277*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0978 (12)0.1145 (12)0.0883 (11)0.0141 (8)0.0050 (8)0.0030 (8)
O40.1174 (15)0.190 (2)0.1145 (16)0.0319 (14)0.0284 (12)0.0079 (15)
N10.0877 (12)0.1129 (14)0.0940 (13)0.0032 (10)0.0056 (9)0.0007 (10)
C70.0945 (15)0.0968 (14)0.1015 (16)0.0193 (11)0.0169 (12)0.0104 (12)
N20.0934 (14)0.160 (2)0.1128 (17)0.0092 (14)0.0132 (12)0.0241 (16)
C130.1102 (17)0.0899 (14)0.0968 (16)0.0003 (12)0.0094 (12)0.0096 (12)
N30.1095 (18)0.169 (3)0.124 (2)0.0232 (17)0.0120 (15)0.0390 (19)
C80.0917 (14)0.0806 (12)0.1014 (15)0.0051 (10)0.0060 (11)0.0209 (11)
O10.159 (2)0.275 (4)0.1037 (16)0.063 (3)0.0161 (15)0.026 (2)
C60.120 (2)0.150 (2)0.0906 (16)0.0267 (18)0.0044 (14)0.0155 (16)
C50.130 (2)0.118 (2)0.116 (2)0.0064 (17)0.0114 (17)0.0212 (16)
C10.0871 (14)0.141 (2)0.0945 (16)0.0176 (14)0.0003 (11)0.0035 (15)
C20.0947 (17)0.124 (2)0.131 (2)0.0053 (14)0.0115 (16)0.0025 (17)
C120.151 (3)0.1107 (19)0.1046 (19)0.0162 (19)0.0084 (19)0.0106 (16)
C90.0969 (18)0.140 (2)0.135 (3)0.0034 (16)0.0031 (17)0.025 (2)
O20.197 (3)0.230 (4)0.212 (4)0.064 (3)0.060 (3)0.109 (3)
C30.0827 (14)0.1249 (19)0.1105 (18)0.0017 (13)0.0031 (12)0.0086 (15)
C100.126 (3)0.165 (3)0.157 (4)0.015 (2)0.040 (3)0.038 (3)
C110.171 (3)0.129 (2)0.117 (2)0.039 (3)0.026 (2)0.034 (2)
C40.131 (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)0.0000.001 (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—C71.344 (3)C8—C91.382 (4)
O3—C61.428 (4)C6—C51.504 (5)
O4—C71.210 (3)C1—C41.466 (5)
N1—C51.469 (4)C2—C31.333 (4)
N1—C11.343 (4)C12—C111.344 (5)
N1—C31.371 (4)C9—C101.380 (6)
C7—C81.464 (4)C10—C111.341 (6)
N2—C11.350 (4)O1'—C1'1.274 (9)
N2—C21.340 (4)C1'—O2'1.129 (9)
C13—C81.370 (4)C1'—C2'1.482 (9)
C13—C121.376 (4)C2'—C1"1.559 (10)
N3—O11.176 (4)C2'—C1"i1.559 (10)
N3—O21.193 (4)O2"—C1"1.161 (11)
N3—C31.441 (4)C1"—O1"1.288 (9)
C7—O3—C6115.3 (2)N2—C1—C4125.4 (3)
C1—N1—C5126.4 (3)C3—C2—N2109.6 (3)
C1—N1—C3106.4 (2)C11—C12—C13121.7 (3)
C3—N1—C5127.1 (3)C10—C9—C8119.5 (3)
O3—C7—C8113.2 (2)N1—C3—N3125.4 (3)
O4—C7—O3121.9 (3)C2—C3—N1107.7 (3)
O4—C7—C8124.9 (3)C2—C3—N3126.9 (3)
C2—N2—C1106.6 (3)C11—C10—C9121.4 (4)
C8—C13—C12119.7 (3)C10—C11—C12119.1 (4)
O1—N3—O2122.9 (4)O1'—C1'—C2'112.0 (7)
O1—N3—C3120.4 (3)O2'—C1'—O1'124.5 (8)
O2—N3—C3116.6 (4)O2'—C1'—C2'122.3 (7)
C13—C8—C7122.0 (2)C1'i—C2'—C1'92.4 (7)
C13—C8—C9118.6 (3)C1'i—C2'—C1"i28.4 (3)
C9—C8—C7119.4 (3)C1'—C2'—C1"i114.4 (6)
O3—C6—C5107.8 (3)C1"i—C2'—C1"140.7 (7)
N1—C5—C6113.4 (3)O2"—C1"—C2'125.5 (7)
N1—C1—N2109.6 (3)O2"—C1"—O1"121.1 (10)
N1—C1—C4125.0 (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+·C7H5O4F(000) = 896
Mr = 429.38Dx = 1.442 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.2443 (4) ÅCell parameters from 9886 reflections
b = 15.9009 (7) Åθ = 2.5–27.5°
c = 15.4526 (8) ŵ = 0.11 mm1
β = 102.454 (2)°T = 301 K
V = 1978.04 (17) Å3Prism, clear light yellow
Z = 40.83 × 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 scansRint = 0.076
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
θmax = 27.5°, θmin = 2.8°
Tmin = 0.490, Tmax = 0.746h = 1010
27674 measured reflectionsk = 2020
4348 independent reflectionsl = 2019
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069All H-atom parameters refined
wR(F2) = 0.185 w = 1/[σ2(Fo2) + (0.0913P)2 + 0.5735P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
4348 reflectionsΔρmax = 0.37 e Å3
356 parametersΔρmin = 0.27 e Å3
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 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
xyzUiso*/Ueq
O30.30908 (16)0.45737 (9)0.10470 (8)0.0471 (3)
O1'0.69550 (19)0.38992 (10)0.49968 (10)0.0592 (4)
N10.25612 (18)0.49805 (10)0.28713 (10)0.0407 (4)
O20.08963 (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)
N20.4226 (2)0.44392 (10)0.40318 (11)0.0478 (4)
N30.0133 (2)0.44450 (12)0.31200 (12)0.0545 (5)
O10.0783 (2)0.40294 (14)0.36109 (14)0.0832 (6)
O40.1499 (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)
C10.4158 (2)0.48952 (12)0.33097 (13)0.0441 (4)
C7'0.6658 (3)0.33991 (13)0.55944 (13)0.0485 (5)
C80.4427 (2)0.37835 (12)0.01068 (13)0.0448 (4)
C60.1575 (2)0.48994 (15)0.12428 (14)0.0494 (5)
C30.1624 (2)0.45427 (12)0.33634 (12)0.0435 (4)
C20.2662 (3)0.42133 (13)0.40789 (13)0.0487 (5)
C50.2007 (3)0.54528 (13)0.20416 (14)0.0479 (5)
C2'0.9742 (3)0.32956 (13)0.62356 (14)0.0531 (5)
C70.2864 (2)0.40967 (13)0.03172 (13)0.0484 (5)
C130.4327 (3)0.33220 (15)0.06576 (17)0.0618 (6)
C90.5971 (3)0.39351 (15)0.06467 (16)0.0563 (5)
C3'1.1037 (4)0.29727 (17)0.6877 (2)0.0774 (8)
C40.5618 (3)0.5256 (2)0.3029 (2)0.0649 (6)
C100.7374 (3)0.36102 (18)0.04179 (19)0.0694 (7)
C120.5745 (4)0.30044 (16)0.08794 (19)0.0693 (7)
C6'0.7806 (4)0.25214 (13)0.69090 (15)0.0616 (6)
C110.7265 (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)
H5A0.292 (3)0.5844 (13)0.2002 (14)0.048 (5)*
H6A0.086 (3)0.4400 (15)0.1351 (16)0.058 (6)*
H20.238 (3)0.3877 (14)0.4495 (17)0.058 (7)*
H5B0.109 (3)0.5774 (15)0.2123 (15)0.057 (6)*
H6B0.099 (3)0.5229 (15)0.0737 (18)0.065 (7)*
H120.564 (4)0.2705 (17)0.142 (2)0.081 (8)*
H90.599 (3)0.4257 (16)0.1141 (18)0.063 (7)*
H3'1.210 (4)0.3103 (19)0.676 (2)0.088 (9)*
H110.823 (4)0.2909 (16)0.0509 (18)0.074 (8)*
H4'A1.152 (4)0.2196 (19)0.798 (2)0.095 (10)*
H4'0.898 (5)0.399 (2)0.523 (2)0.116 (12)*
H100.843 (4)0.370 (2)0.082 (2)0.100 (10)*
H130.330 (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)*
H4A0.575 (5)0.504 (2)0.250 (3)0.117 (13)*
H4B0.554 (6)0.585 (3)0.303 (3)0.133 (15)*
H4C0.653 (6)0.515 (3)0.347 (3)0.138 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0316 (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)
N10.0297 (8)0.0472 (8)0.0446 (8)0.0045 (6)0.0068 (6)0.0010 (6)
O20.0341 (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)
N20.0387 (9)0.0542 (9)0.0468 (9)0.0072 (7)0.0006 (7)0.0072 (7)
N30.0333 (9)0.0752 (12)0.0560 (10)0.0015 (8)0.0114 (7)0.0005 (8)
O10.0479 (10)0.1147 (15)0.0903 (13)0.0120 (10)0.0222 (9)0.0255 (11)
O40.0375 (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)
C10.0318 (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)
C80.0391 (10)0.0469 (9)0.0474 (10)0.0003 (8)0.0071 (8)0.0036 (8)
C60.0315 (10)0.0673 (13)0.0481 (10)0.0081 (9)0.0057 (8)0.0033 (9)
C30.0339 (10)0.0502 (10)0.0461 (9)0.0032 (7)0.0076 (7)0.0035 (8)
C20.0459 (11)0.0546 (11)0.0445 (10)0.0032 (9)0.0075 (8)0.0003 (8)
C50.0411 (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)
C70.0371 (10)0.0581 (11)0.0472 (10)0.0012 (8)0.0026 (8)0.0017 (8)
C130.0543 (14)0.0662 (14)0.0628 (13)0.0018 (11)0.0084 (11)0.0111 (11)
C90.0408 (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)
C40.0343 (12)0.0828 (18)0.0783 (17)0.0058 (11)0.0140 (11)0.0068 (14)
C100.0387 (13)0.0857 (17)0.0824 (17)0.0056 (11)0.0097 (11)0.0019 (14)
C120.0786 (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)
C110.0559 (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—C61.444 (2)C6—C51.495 (3)
O3—C71.338 (2)C6—H6A1.02 (2)
O1'—C7'1.282 (3)C6—H6B0.98 (3)
O1'—H1'1.32 (5)C3—C21.350 (3)
N1—C11.351 (2)C2—H20.90 (2)
N1—C31.383 (2)C5—H5A0.99 (2)
N1—C51.471 (2)C5—H5B0.95 (2)
O2—N31.225 (2)C2'—C3'1.389 (3)
O4'—C2'1.345 (3)C13—C121.383 (4)
O4'—H4'1.05 (4)C13—H130.93 (3)
O2'—C7'1.246 (3)C9—C101.381 (3)
O2'—H2'1.38 (5)C9—H90.92 (3)
N2—C11.322 (3)C3'—C4'1.371 (5)
N2—C21.355 (3)C3'—H3'0.96 (3)
N2—H1'1.25 (5)C4—H4A0.92 (4)
N3—O11.214 (2)C4—H4B0.95 (4)
N3—C31.424 (3)C4—H4C0.92 (5)
O4—C71.207 (3)C10—C111.359 (4)
O3'—C6'1.356 (3)C10—H100.97 (4)
O3'—H2'1.15 (5)C12—C111.370 (4)
C1'—C7'1.477 (3)C12—H120.94 (3)
C1'—C2'1.408 (3)C6'—C5'1.380 (4)
C1'—C6'1.402 (3)C11—H110.97 (3)
C1—C41.480 (3)C4'—C5'1.365 (5)
C8—C71.481 (3)C4'—H4'A0.96 (4)
C8—C131.378 (3)C5'—H5'1.00 (3)
C8—C91.385 (3)
C7—O3—C6114.21 (15)C6—C5—H5B111.8 (15)
C7'—O1'—H1'105.9 (17)H5A—C5—H5B108.1 (19)
C1—N1—C3105.86 (15)O4'—C2'—C1'122.70 (19)
C1—N1—C5125.05 (17)O4'—C2'—C3'117.9 (2)
C3—N1—C5129.09 (16)C3'—C2'—C1'119.4 (2)
C2'—O4'—H4'104.8 (19)O3—C7—C8113.92 (17)
C7'—O2'—H2'96.7 (17)O4—C7—O3122.18 (19)
C1—N2—C2108.84 (17)O4—C7—C8123.90 (19)
C1—N2—H1'127.8 (19)C8—C13—C12120.6 (2)
C2—N2—H1'122.7 (18)C8—C13—H13119.3 (19)
O2—N3—C3119.01 (18)C12—C13—H13120.0 (19)
O1—N3—O2123.94 (19)C8—C9—H9116.6 (17)
O1—N3—C3117.05 (18)C10—C9—C8119.5 (2)
C6'—O3'—H2'94 (2)C10—C9—H9123.9 (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—C4125.5 (2)C1—C4—H4A112 (2)
N2—C1—N1109.75 (17)C1—C4—H4B109 (3)
N2—C1—C4124.8 (2)C1—C4—H4C107 (3)
O1'—C7'—C1'117.54 (18)H4A—C4—H4B113 (4)
O2'—C7'—O1'121.3 (2)H4A—C4—H4C111 (4)
O2'—C7'—C1'121.1 (2)H4B—C4—H4C104 (4)
C13—C8—C7118.26 (19)C9—C10—H10118 (2)
C13—C8—C9119.1 (2)C11—C10—C9121.0 (2)
C9—C8—C7122.66 (19)C11—C10—H10121 (2)
O3—C6—C5108.75 (16)C13—C12—H12118.5 (19)
O3—C6—H6A108.1 (13)C11—C12—C13119.7 (2)
O3—C6—H6B108.8 (15)C11—C12—H12121.8 (19)
C5—C6—H6A111.4 (13)O3'—C6'—C1'121.5 (2)
C5—C6—H6B109.4 (14)O3'—C6'—C5'118.2 (3)
H6A—C6—H6B110 (2)C5'—C6'—C1'120.3 (3)
N1—C3—N3124.52 (17)C10—C11—C12120.0 (2)
C2—C3—N1108.34 (17)C10—C11—H11122.8 (17)
C2—C3—N3127.11 (19)C12—C11—H11117.2 (17)
N2—C2—H2125.8 (17)C3'—C4'—H4'A126 (2)
C3—C2—N2107.21 (19)C5'—C4'—C3'121.6 (3)
C3—C2—H2126.8 (17)C5'—C4'—H4'A113 (2)
N1—C5—C6113.14 (17)C6'—C5'—H5'115 (2)
N1—C5—H5A106.2 (13)C4'—C5'—C6'119.8 (3)
N1—C5—H5B105.5 (14)C4'—C5'—H5'126 (2)
C6—C5—H5A111.6 (13)
2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl benzoate–3,5-dihydroxybenzoic acid (3/1) (bzmd35dba) top
Crystal data top
3C13H13N3O4·C7H6O4F(000) = 2048
Mr = 979.91Dx = 1.394 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 7.1481 (2) ÅCell parameters from 9896 reflections
b = 36.7892 (8) Åθ = 3.5–67.6°
c = 18.0584 (4) ŵ = 0.91 mm1
β = 100.451 (1)°T = 300 K
V = 4670.1 (2) Å3Prism, clear light colourless
Z = 40.28 × 0.14 × 0.06 mm
Data collection top
Bruker APEXII CCD
diffractometer
5499 reflections with I > 2σ(I)
Multilayer mirrors monochromatorRint = 0.058
φ and ω scansθmax = 68.7°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
h = 78
Tmin = 0.835, Tmax = 0.986k = 4444
56516 measured reflectionsl = 2121
8547 independent reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.052 w = 1/[σ2(Fo2) + (0.0833P)2 + 2.1514P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.176(Δ/σ)max = 0.002
S = 1.01Δρmax = 0.27 e Å3
8547 reflectionsΔρmin = 0.21 e Å3
844 parametersExtinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.00125 (13)
Primary atom site location: dual
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 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
xyzUiso*/UeqOcc. (<1)
O1C0.8254 (4)0.36199 (7)0.06761 (14)0.0939 (7)
O2C0.5826 (4)0.32866 (7)0.11345 (12)0.0874 (7)
O3C0.3392 (3)0.26359 (5)0.03750 (10)0.0688 (5)
O3A0.7853 (3)0.47087 (5)0.86671 (10)0.0634 (5)
N1A0.9537 (3)0.51097 (6)0.74799 (11)0.0540 (5)
O3B0.7069 (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)
O4C0.2932 (4)0.20905 (6)0.01637 (14)0.0909 (7)
N1C0.4294 (3)0.33992 (6)0.01710 (12)0.0571 (5)
N2C0.5611 (4)0.37320 (7)0.11443 (14)0.0772 (7)
N3C0.6713 (4)0.34779 (7)0.06396 (14)0.0668 (6)
C1C0.4139 (5)0.35240 (8)0.08614 (16)0.0697 (8)
C2C0.6752 (5)0.37470 (8)0.06255 (18)0.0705 (8)
H2C0.785 (5)0.3879 (9)0.0685 (17)0.074 (9)*
C3C0.5974 (4)0.35420 (7)0.00232 (15)0.0578 (6)
C4C0.2524 (9)0.34396 (14)0.1246 (3)0.1032 (14)
H4CA0.207 (7)0.3175 (15)0.123 (3)0.154 (19)*
H4CB0.284 (7)0.3513 (15)0.170 (3)0.15 (2)*
H4CC0.140 (10)0.3572 (18)0.104 (3)0.19 (3)*
C5C0.2834 (4)0.31870 (8)0.03207 (18)0.0639 (7)
H5CA0.260 (4)0.3289 (8)0.0824 (17)0.069 (8)*
H5CB0.161 (5)0.3213 (8)0.0124 (16)0.075 (9)*
C6C0.3292 (5)0.27923 (8)0.03625 (16)0.0651 (7)
H6CA0.454 (5)0.2757 (9)0.0532 (18)0.085 (10)*
H6CB0.231 (4)0.2679 (8)0.0697 (16)0.063 (8)*
C7C0.3174 (4)0.22757 (8)0.03984 (18)0.0659 (7)
C14C0.332 (6)0.2182 (8)0.1204 (10)0.068 (6)0.5318
C15C0.390 (4)0.2413 (5)0.1819 (15)0.068 (3)0.5318
H15C0.4198670.2653180.1731660.082*0.5318
C16C0.403 (2)0.2292 (5)0.2561 (9)0.093 (4)0.5318
H16C0.4347810.2458240.2951170.112*0.5318
C17C0.370 (2)0.1927 (6)0.2740 (8)0.112 (5)0.5318
H17C0.3856480.1845150.3235530.135*0.5318
C18C0.310 (2)0.1691 (4)0.2119 (7)0.101 (6)0.5318
H18C0.2777960.1451680.2201810.121*0.5318
C19C0.300 (3)0.1817 (6)0.1385 (13)0.088 (4)0.5318
H19C0.2704970.1651230.0992080.105*0.5318
C8C0.322 (6)0.2090 (9)0.1134 (10)0.062 (6)0.4682
C13C0.364 (4)0.2293 (6)0.176 (2)0.081 (6)0.4682
H13C0.3926180.2538790.1738080.097*0.4682
C12C0.362 (3)0.2123 (5)0.2448 (12)0.099 (6)0.4682
H12C0.3908470.2253570.2895140.119*0.4682
C11C0.317 (3)0.1770 (6)0.2460 (7)0.094 (5)0.4682
H11C0.3179490.1651770.2915640.113*0.4682
C10C0.269 (3)0.1580 (6)0.1779 (9)0.109 (6)0.4682
H10C0.2389080.1334900.1791620.130*0.4682
C9C0.266 (4)0.1735 (6)0.1132 (13)0.081 (5)0.4682
H9C0.2264390.1609160.0684310.097*0.4682
O1A0.8622 (4)0.60568 (6)0.72428 (15)0.1031 (8)
O2A0.9845 (4)0.57753 (6)0.82685 (13)0.0913 (7)
O4A0.7325 (4)0.47827 (10)0.98395 (13)0.1178 (10)
N2A0.8422 (3)0.50522 (6)0.62493 (12)0.0589 (5)
N3A0.9160 (4)0.57788 (7)0.75940 (15)0.0722 (7)
C1A0.9167 (4)0.48799 (7)0.68826 (14)0.0548 (6)
C2A0.8300 (4)0.54068 (8)0.64394 (16)0.0613 (7)
H2A0.782 (4)0.5591 (8)0.6103 (18)0.076 (9)*
C3A0.8979 (4)0.54472 (7)0.71862 (15)0.0574 (6)
C4A0.9548 (6)0.44854 (9)0.6922 (2)0.0726 (8)
H4AA1.089 (6)0.4430 (11)0.708 (2)0.112 (14)*
H4AB0.892 (5)0.4370 (10)0.731 (2)0.106 (12)*
H4AC0.902 (6)0.4365 (11)0.648 (3)0.122 (14)*
C5A1.0501 (4)0.50018 (10)0.82398 (15)0.0628 (7)
H5AA1.146 (4)0.5180 (8)0.8411 (16)0.073 (9)*
H5AB1.104 (5)0.4746 (10)0.8180 (18)0.085 (10)*
C6A0.9251 (5)0.49971 (10)0.88285 (16)0.0666 (7)
H6AA1.011 (4)0.4945 (8)0.9322 (18)0.078 (9)*
H6AB0.859 (5)0.5241 (10)0.8861 (18)0.091 (11)*
C7A0.6892 (4)0.46458 (9)0.92272 (16)0.0726 (8)
C8A0.5226 (4)0.44060 (9)0.90204 (17)0.0701 (8)
C9A0.4877 (5)0.42069 (9)0.8363 (2)0.0777 (9)
H9A0.580 (4)0.4208 (8)0.8021 (17)0.072 (9)*
C10A0.3229 (6)0.39958 (10)0.8191 (3)0.0967 (13)
H10A0.307 (6)0.3863 (11)0.770 (2)0.117 (14)*
C11A0.1962 (6)0.39897 (12)0.8675 (3)0.1073 (15)
H11A0.073 (7)0.3852 (12)0.856 (3)0.135 (16)*
C12A0.2295 (6)0.41829 (12)0.9333 (3)0.1003 (13)
H12A0.134 (6)0.4175 (11)0.969 (2)0.115 (13)*
C13A0.3934 (5)0.43885 (11)0.9514 (2)0.0867 (10)
H13A0.422 (6)0.4556 (11)0.993 (2)0.107 (14)*
O1B0.2377 (4)0.64048 (6)0.62852 (13)0.0840 (6)
O2B0.4848 (4)0.67270 (7)0.67579 (13)0.0956 (8)
O4B0.6319 (4)0.77703 (6)0.50557 (12)0.0850 (7)
N1B0.6714 (3)0.64843 (6)0.56085 (12)0.0595 (5)
N2B0.5676 (4)0.60475 (6)0.47891 (13)0.0670 (6)
N3B0.4023 (4)0.65101 (7)0.62963 (14)0.0713 (7)
C1B0.7086 (4)0.62802 (7)0.50247 (16)0.0645 (7)
C2B0.4352 (5)0.61020 (8)0.52319 (17)0.0656 (7)
H2B0.320 (4)0.5970 (8)0.5189 (16)0.066 (8)*
C3B0.4962 (4)0.63698 (7)0.57283 (15)0.0596 (7)
C4B0.8810 (5)0.63092 (11)0.4683 (2)0.0961 (11)
H4BA0.8904750.6551020.4493530.144*
H4BB0.8731500.6138160.4277000.144*
H4BC0.9914400.6257190.5056770.144*
C5B0.7922 (5)0.67798 (8)0.5974 (2)0.0694 (8)
H5BA0.807 (5)0.6749 (9)0.652 (2)0.087 (10)*
H5BB0.912 (5)0.6750 (8)0.5815 (16)0.072 (9)*
C6B0.7111 (5)0.71471 (8)0.57400 (17)0.0683 (8)
H6BA0.786 (4)0.7336 (8)0.6008 (16)0.063 (8)*
H6BB0.574 (5)0.7165 (8)0.5825 (17)0.078 (9)*
C7B0.6616 (4)0.75204 (8)0.46585 (16)0.0633 (7)
C8B0.6546 (4)0.75459 (8)0.38362 (16)0.0656 (7)
C9B0.6406 (5)0.72461 (11)0.3370 (2)0.0789 (9)
H9B0.642 (4)0.7020 (8)0.3596 (16)0.065 (9)*
C10B0.6313 (6)0.72971 (15)0.2597 (2)0.0979 (12)
H10B0.631 (5)0.7072 (11)0.233 (2)0.111 (13)*
C11B0.6431 (6)0.76410 (15)0.2314 (2)0.1012 (12)
H11B0.643 (6)0.7687 (12)0.175 (3)0.139 (16)*
C12B0.6565 (6)0.79407 (14)0.2768 (2)0.0951 (11)
H12B0.670 (7)0.8222 (16)0.256 (3)0.17 (2)*
C13B0.6609 (5)0.78897 (11)0.3529 (2)0.0802 (9)
H13B0.664 (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'A0.695 (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
U11U22U33U12U13U23
O1C0.0824 (16)0.1000 (17)0.1057 (18)0.0177 (14)0.0339 (14)0.0013 (13)
O2C0.0938 (16)0.1079 (17)0.0617 (12)0.0126 (14)0.0174 (12)0.0190 (12)
O3C0.0881 (14)0.0579 (11)0.0581 (11)0.0031 (10)0.0070 (10)0.0047 (8)
O3A0.0616 (11)0.0758 (12)0.0500 (10)0.0110 (9)0.0026 (8)0.0045 (8)
N1A0.0514 (12)0.0630 (12)0.0460 (11)0.0034 (10)0.0046 (9)0.0001 (9)
O3B0.0864 (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)
O4C0.116 (2)0.0611 (12)0.0930 (16)0.0062 (12)0.0128 (14)0.0160 (11)
N1C0.0628 (14)0.0536 (12)0.0546 (12)0.0006 (10)0.0095 (10)0.0075 (9)
N2C0.104 (2)0.0613 (14)0.0633 (15)0.0020 (14)0.0076 (15)0.0174 (11)
N3C0.0673 (16)0.0680 (14)0.0659 (15)0.0002 (12)0.0147 (12)0.0021 (12)
C1C0.090 (2)0.0590 (16)0.0627 (17)0.0081 (16)0.0208 (16)0.0108 (13)
C2C0.080 (2)0.0572 (16)0.0690 (19)0.0039 (16)0.0005 (16)0.0073 (13)
C3C0.0616 (16)0.0537 (14)0.0570 (15)0.0024 (12)0.0075 (12)0.0062 (11)
C4C0.121 (4)0.102 (3)0.103 (3)0.003 (3)0.062 (3)0.019 (3)
C5C0.0621 (18)0.0632 (16)0.0633 (17)0.0010 (14)0.0028 (14)0.0020 (13)
C6C0.077 (2)0.0599 (16)0.0555 (16)0.0066 (15)0.0039 (15)0.0061 (12)
C7C0.0581 (17)0.0605 (16)0.0777 (19)0.0021 (13)0.0089 (14)0.0006 (14)
C14C0.056 (6)0.054 (13)0.098 (10)0.007 (8)0.024 (7)0.010 (8)
C15C0.065 (7)0.081 (9)0.059 (5)0.005 (7)0.013 (5)0.002 (7)
C16C0.074 (6)0.136 (13)0.072 (8)0.007 (7)0.021 (5)0.011 (7)
C17C0.083 (8)0.183 (16)0.073 (10)0.020 (8)0.019 (7)0.038 (9)
C18C0.126 (9)0.123 (15)0.063 (13)0.014 (9)0.043 (12)0.038 (11)
C19C0.084 (7)0.068 (10)0.114 (14)0.003 (6)0.027 (8)0.007 (8)
C8C0.066 (8)0.054 (15)0.067 (6)0.011 (10)0.017 (5)0.005 (6)
C13C0.070 (9)0.087 (13)0.086 (10)0.007 (9)0.015 (8)0.011 (13)
C12C0.094 (12)0.14 (2)0.063 (8)0.015 (11)0.010 (7)0.002 (10)
C11C0.093 (9)0.155 (15)0.036 (10)0.032 (8)0.021 (8)0.029 (10)
C10C0.150 (14)0.101 (10)0.088 (13)0.036 (9)0.056 (11)0.020 (8)
C9C0.100 (12)0.058 (9)0.095 (11)0.005 (7)0.044 (10)0.007 (6)
O1A0.137 (2)0.0657 (14)0.1079 (19)0.0135 (14)0.0244 (17)0.0030 (13)
O2A0.1095 (19)0.0871 (15)0.0741 (15)0.0183 (13)0.0079 (13)0.0214 (11)
O4A0.1005 (19)0.196 (3)0.0587 (14)0.052 (2)0.0189 (13)0.0193 (16)
N2A0.0597 (13)0.0659 (13)0.0497 (12)0.0009 (11)0.0058 (10)0.0008 (10)
N3A0.0755 (17)0.0693 (16)0.0738 (17)0.0062 (13)0.0188 (14)0.0087 (13)
C1A0.0532 (15)0.0615 (15)0.0478 (13)0.0055 (12)0.0042 (11)0.0006 (11)
C2A0.0597 (17)0.0686 (17)0.0553 (15)0.0032 (14)0.0094 (13)0.0067 (13)
C3A0.0550 (15)0.0584 (15)0.0587 (15)0.0015 (12)0.0102 (12)0.0027 (12)
C4A0.083 (2)0.0656 (18)0.0656 (19)0.0013 (17)0.0029 (18)0.0013 (15)
C5A0.0545 (16)0.082 (2)0.0474 (14)0.0103 (16)0.0024 (12)0.0011 (13)
C6A0.0629 (18)0.084 (2)0.0497 (15)0.0158 (16)0.0029 (13)0.0046 (13)
C7A0.0642 (18)0.099 (2)0.0526 (16)0.0075 (16)0.0065 (14)0.0075 (15)
C8A0.0601 (17)0.0775 (19)0.0684 (18)0.0014 (15)0.0002 (14)0.0213 (15)
C9A0.075 (2)0.0714 (19)0.080 (2)0.0069 (17)0.0042 (18)0.0225 (16)
C10A0.096 (3)0.073 (2)0.106 (3)0.017 (2)0.022 (2)0.025 (2)
C11A0.075 (3)0.091 (3)0.147 (4)0.015 (2)0.004 (3)0.054 (3)
C12A0.070 (2)0.098 (3)0.132 (4)0.000 (2)0.016 (3)0.048 (3)
C13A0.072 (2)0.089 (2)0.100 (3)0.0007 (19)0.018 (2)0.030 (2)
O1B0.0854 (16)0.0831 (14)0.0907 (16)0.0068 (12)0.0346 (13)0.0075 (11)
O2B0.119 (2)0.0971 (17)0.0754 (14)0.0060 (15)0.0307 (14)0.0279 (13)
O4B0.1183 (19)0.0642 (12)0.0757 (13)0.0054 (12)0.0259 (13)0.0099 (10)
N1B0.0624 (14)0.0547 (12)0.0617 (13)0.0001 (10)0.0124 (11)0.0074 (10)
N2B0.0788 (16)0.0565 (13)0.0677 (14)0.0021 (12)0.0185 (12)0.0091 (11)
N3B0.0839 (19)0.0675 (15)0.0669 (15)0.0051 (14)0.0255 (13)0.0013 (12)
C1B0.0701 (18)0.0575 (15)0.0682 (17)0.0022 (14)0.0184 (14)0.0096 (13)
C2B0.073 (2)0.0566 (15)0.0691 (18)0.0000 (15)0.0184 (15)0.0025 (13)
C3B0.0700 (18)0.0549 (14)0.0556 (15)0.0033 (13)0.0160 (13)0.0023 (11)
C4B0.082 (2)0.108 (3)0.107 (3)0.003 (2)0.040 (2)0.027 (2)
C5B0.071 (2)0.0659 (17)0.068 (2)0.0021 (15)0.0047 (16)0.0121 (14)
C6B0.082 (2)0.0601 (16)0.0617 (17)0.0084 (16)0.0107 (15)0.0123 (13)
C7B0.0599 (17)0.0608 (16)0.0692 (17)0.0066 (13)0.0118 (14)0.0101 (13)
C8B0.0540 (16)0.0779 (19)0.0640 (17)0.0071 (14)0.0081 (13)0.0126 (14)
C9B0.070 (2)0.087 (2)0.079 (2)0.0118 (18)0.0120 (16)0.0207 (18)
C10B0.083 (3)0.130 (4)0.079 (2)0.007 (2)0.0084 (19)0.038 (3)
C11B0.085 (3)0.147 (4)0.071 (2)0.002 (3)0.011 (2)0.002 (3)
C12B0.092 (3)0.120 (3)0.073 (2)0.000 (2)0.0145 (19)0.010 (2)
C13B0.079 (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—N3C1.232 (3)C4A—H4AA0.97 (4)
O2C—N3C1.221 (3)C4A—H4AB1.00 (4)
O3C—C6C1.440 (3)C4A—H4AC0.94 (5)
O3C—C7C1.336 (3)C5A—H5AA0.96 (3)
O3A—C6A1.450 (3)C5A—H5AB1.03 (3)
O3A—C7A1.342 (3)C5A—C6A1.508 (4)
N1A—C1A1.358 (3)C6A—H6AA1.00 (3)
N1A—C3A1.380 (3)C6A—H6AB1.02 (4)
N1A—C5A1.474 (3)C7A—C8A1.475 (4)
O3B—C6B1.447 (3)C8A—C9A1.379 (5)
O3B—C7B1.344 (3)C8A—C13A1.396 (5)
O3'—H3'0.97 (4)C9A—H9A0.98 (3)
O3'—C3'1.369 (3)C9A—C10A1.398 (5)
O4'—H4'0.96 (4)C10A—H10A0.99 (4)
O4'—C5'1.363 (3)C10A—C11A1.368 (7)
O4C—C7C1.209 (4)C11A—H11A1.00 (5)
N1C—C1C1.352 (3)C11A—C12A1.368 (7)
N1C—C3C1.381 (3)C12A—H12A1.03 (4)
N1C—C5C1.466 (3)C12A—C13A1.382 (6)
N2C—C1C1.326 (4)C13A—H13A0.96 (4)
N2C—C2C1.350 (4)O1B—N3B1.235 (3)
N3C—C3C1.413 (3)O2B—N3B1.225 (3)
C1C—C4C1.484 (5)O4B—C7B1.208 (3)
C2C—H2C0.92 (3)N1B—C1B1.359 (3)
C2C—C3C1.357 (4)N1B—C3B1.375 (3)
C4C—H4CA1.02 (5)N1B—C5B1.468 (4)
C4C—H4CB0.85 (6)N2B—C1B1.332 (4)
C4C—H4CC0.95 (7)N2B—C2B1.360 (4)
C5C—H5CA0.97 (3)N3B—C3B1.421 (3)
C5C—H5CB1.01 (3)C1B—C4B1.479 (4)
C5C—C6C1.493 (4)C2B—H2B0.95 (3)
C6C—H6CA1.00 (3)C2B—C3B1.350 (4)
C6C—H6CB0.94 (3)C4B—H4BA0.9600
C7C—C14C1.480 (13)C4B—H4BB0.9600
C7C—C8C1.489 (12)C4B—H4BC0.9600
C14C—C15C1.40 (3)C5B—H5BA0.98 (3)
C14C—C19C1.41 (3)C5B—H5BB0.96 (3)
C15C—H15C0.9300C5B—C6B1.500 (4)
C15C—C16C1.40 (3)C6B—H6BA0.95 (3)
C16C—H16C0.9300C6B—H6BB1.02 (3)
C16C—C17C1.41 (3)C7B—C8B1.480 (4)
C17C—H17C0.9300C8B—C9B1.380 (4)
C17C—C18C1.42 (2)C8B—C13B1.386 (5)
C18C—H18C0.9300C9B—H9B0.93 (3)
C18C—C19C1.39 (3)C9B—C10B1.399 (5)
C19C—H19C0.9300C10B—H10B0.96 (4)
C8C—C13C1.35 (4)C10B—C11B1.372 (6)
C8C—C9C1.37 (4)C11B—H11B1.04 (5)
C13C—H13C0.9300C11B—C12B1.367 (6)
C13C—C12C1.39 (4)C12B—H12B1.11 (6)
C12C—H12C0.9300C12B—C13B1.381 (5)
C12C—C11C1.34 (3)C13B—H13B0.97 (3)
C11C—H11C0.9300O1'—H1'0.99 (5)
C11C—C10C1.402 (19)O1'—C7'1.308 (3)
C10C—H10C0.9300O2'—C7'1.202 (3)
C10C—C9C1.29 (4)C1'—C2'1.383 (3)
C9C—H9C0.9300C1'—C6'1.383 (3)
O1A—N3A1.228 (3)C1'—C7'1.492 (3)
O2A—N3A1.228 (3)C2'—H2'0.98 (3)
O4A—C7A1.203 (4)C2'—C3'1.388 (3)
N2A—C1A1.331 (3)C3'—C4'1.384 (3)
N2A—C2A1.356 (4)C4'—H4'A0.95 (3)
N3A—C3A1.419 (4)C4'—C5'1.385 (4)
C1A—C4A1.476 (4)C5'—C6'1.391 (3)
C2A—H2A0.93 (3)C6'—H6'0.99 (3)
C2A—C3A1.356 (4)
C7C—O3C—C6C116.0 (2)C6A—C5A—H5AA105.1 (18)
C7A—O3A—C6A113.8 (2)C6A—C5A—H5AB110.2 (18)
C1A—N1A—C3A104.7 (2)O3A—C6A—C5A110.0 (2)
C1A—N1A—C5A124.2 (2)O3A—C6A—H6AA108.9 (17)
C3A—N1A—C5A130.8 (2)O3A—C6A—H6AB110 (2)
C7B—O3B—C6B115.5 (2)C5A—C6A—H6AA106.5 (18)
C3'—O3'—H3'113 (2)C5A—C6A—H6AB111.7 (19)
C5'—O4'—H4'112 (2)H6AA—C6A—H6AB109 (3)
C1C—N1C—C3C105.6 (2)O3A—C7A—C8A114.4 (3)
C1C—N1C—C5C124.8 (3)O4A—C7A—O3A122.6 (3)
C3C—N1C—C5C129.3 (2)O4A—C7A—C8A123.0 (3)
C1C—N2C—C2C107.1 (2)C9A—C8A—C7A123.2 (3)
O1C—N3C—C3C116.7 (3)C9A—C8A—C13A119.2 (3)
O2C—N3C—O1C123.8 (3)C13A—C8A—C7A117.6 (3)
O2C—N3C—C3C119.5 (2)C8A—C9A—H9A120.2 (19)
N1C—C1C—C4C124.1 (3)C8A—C9A—C10A119.9 (4)
N2C—C1C—N1C111.1 (3)C10A—C9A—H9A119.9 (19)
N2C—C1C—C4C124.8 (3)C9A—C10A—H10A115 (3)
N2C—C2C—H2C124 (2)C11A—C10A—C9A119.8 (5)
N2C—C2C—C3C108.8 (3)C11A—C10A—H10A125 (3)
C3C—C2C—H2C128 (2)C10A—C11A—H11A122 (3)
N1C—C3C—N3C124.9 (2)C10A—C11A—C12A121.0 (4)
C2C—C3C—N1C107.5 (3)C12A—C11A—H11A117 (3)
C2C—C3C—N3C127.6 (3)C11A—C12A—H12A120 (2)
C1C—C4C—H4CA117 (3)C11A—C12A—C13A119.7 (5)
C1C—C4C—H4CB107 (4)C13A—C12A—H12A120 (2)
C1C—C4C—H4CC113 (4)C8A—C13A—H13A113 (3)
H4CA—C4C—H4CB110 (5)C12A—C13A—C8A120.3 (5)
H4CA—C4C—H4CC104 (5)C12A—C13A—H13A126 (3)
H4CB—C4C—H4CC105 (5)C1B—N1B—C3B105.3 (2)
N1C—C5C—H5CA110.2 (17)C1B—N1B—C5B125.1 (3)
N1C—C5C—H5CB107.7 (17)C3B—N1B—C5B129.4 (2)
N1C—C5C—C6C114.2 (3)C1B—N2B—C2B106.5 (2)
H5CA—C5C—H5CB106 (2)O1B—N3B—C3B116.6 (3)
C6C—C5C—H5CA109.3 (17)O2B—N3B—O1B123.7 (3)
C6C—C5C—H5CB108.8 (17)O2B—N3B—C3B119.7 (3)
O3C—C6C—C5C108.4 (2)N1B—C1B—C4B125.4 (3)
O3C—C6C—H6CA109.5 (19)N2B—C1B—N1B111.1 (2)
O3C—C6C—H6CB108.9 (17)N2B—C1B—C4B123.6 (3)
C5C—C6C—H6CA110.9 (19)N2B—C2B—H2B124.3 (17)
C5C—C6C—H6CB108.6 (17)C3B—C2B—N2B108.8 (3)
H6CA—C6C—H6CB110 (2)C3B—C2B—H2B126.8 (17)
O3C—C7C—C14C105.9 (12)N1B—C3B—N3B124.4 (2)
O3C—C7C—C8C120.0 (13)C2B—C3B—N1B108.2 (2)
O4C—C7C—O3C122.2 (3)C2B—C3B—N3B127.3 (3)
O4C—C7C—C14C131.9 (12)C1B—C4B—H4BA109.5
O4C—C7C—C8C117.9 (13)C1B—C4B—H4BB109.5
C15C—C14C—C7C127 (2)C1B—C4B—H4BC109.5
C15C—C14C—C19C115.6 (14)H4BA—C4B—H4BB109.5
C19C—C14C—C7C118 (2)H4BA—C4B—H4BC109.5
C14C—C15C—H15C119.2H4BB—C4B—H4BC109.5
C14C—C15C—C16C121.7 (15)N1B—C5B—H5BA108 (2)
C16C—C15C—H15C119.2N1B—C5B—H5BB105.4 (18)
C15C—C16C—H16C118.7N1B—C5B—C6B112.0 (3)
C17C—C16C—C15C122.5 (13)H5BA—C5B—H5BB111 (3)
C17C—C16C—H16C118.7C6B—C5B—H5BA111 (2)
C16C—C17C—H17C122.0C6B—C5B—H5BB109.9 (18)
C16C—C17C—C18C115.9 (14)O3B—C6B—C5B108.0 (2)
C18C—C17C—H17C122.0O3B—C6B—H6BA110.0 (17)
C17C—C18C—H18C119.8O3B—C6B—H6BB107.2 (18)
C19C—C18C—C17C120.4 (15)C5B—C6B—H6BA111.2 (17)
C19C—C18C—H18C119.8C5B—C6B—H6BB110.5 (17)
C14C—C19C—H19C118.2H6BA—C6B—H6BB110 (2)
C18C—C19C—C14C123.6 (15)O3B—C7B—C8B113.5 (2)
C18C—C19C—H19C118.2O4B—C7B—O3B121.7 (3)
C13C—C8C—C7C118 (3)O4B—C7B—C8B124.7 (3)
C9C—C8C—C7C119 (2)C9B—C8B—C7B123.1 (3)
C9C—C8C—C13C123.6 (17)C9B—C8B—C13B119.3 (3)
C8C—C13C—H13C121.2C13B—C8B—C7B117.6 (3)
C12C—C13C—C8C117.7 (19)C8B—C9B—H9B117.2 (19)
C12C—C13C—H13C121.2C8B—C9B—C10B119.1 (4)
C13C—C12C—H12C120.3C10B—C9B—H9B123.6 (19)
C11C—C12C—C13C119.5 (17)C9B—C10B—H10B112 (2)
C11C—C12C—H12C120.3C11B—C10B—C9B120.0 (4)
C12C—C11C—H11C120.3C11B—C10B—H10B127 (2)
C12C—C11C—C10C119 (2)C10B—C11B—H11B122 (3)
C10C—C11C—H11C120.3C12B—C11B—C10B121.5 (4)
C11C—C10C—H10C118.8C12B—C11B—H11B117 (3)
C9C—C10C—C11C122 (2)C11B—C12B—H12B124 (3)
C9C—C10C—H10C118.8C11B—C12B—C13B118.2 (4)
C8C—C9C—H9C121.3C13B—C12B—H12B118 (3)
C10C—C9C—C8C117.4 (16)C8B—C13B—H13B119 (2)
C10C—C9C—H9C121.3C12B—C13B—C8B121.8 (4)
C1A—N2A—C2A105.9 (2)C12B—C13B—H13B119 (2)
O1A—N3A—C3A117.2 (3)C7'—O1'—H1'109 (2)
O2A—N3A—O1A123.5 (3)C2'—C1'—C6'121.5 (2)
O2A—N3A—C3A119.2 (3)C2'—C1'—C7'117.9 (2)
N1A—C1A—C4A124.5 (2)C6'—C1'—C7'120.6 (2)
N2A—C1A—N1A112.1 (2)C1'—C2'—H2'123.3 (16)
N2A—C1A—C4A123.5 (2)C1'—C2'—C3'118.9 (2)
N2A—C2A—H2A124.5 (19)C3'—C2'—H2'117.7 (16)
N2A—C2A—C3A109.2 (3)O3'—C3'—C2'117.5 (2)
C3A—C2A—H2A126.3 (19)O3'—C3'—C4'122.0 (2)
N1A—C3A—N3A125.6 (2)C4'—C3'—C2'120.5 (2)
C2A—C3A—N1A108.0 (2)C3'—C4'—H4'A119.7 (17)
C2A—C3A—N3A126.4 (3)C3'—C4'—C5'119.9 (2)
C1A—C4A—H4AA113 (2)C5'—C4'—H4'A120.4 (17)
C1A—C4A—H4AB110 (2)O4'—C5'—C4'122.1 (2)
C1A—C4A—H4AC112 (3)O4'—C5'—C6'117.6 (2)
H4AA—C4A—H4AB104 (3)C4'—C5'—C6'120.3 (2)
H4AA—C4A—H4AC112 (3)C1'—C6'—C5'118.9 (2)
H4AB—C4A—H4AC104 (3)C1'—C6'—H6'121.7 (15)
N1A—C5A—H5AA107.6 (18)C5'—C6'—H6'119.3 (15)
N1A—C5A—H5AB105.7 (18)O1'—C7'—C1'113.8 (2)
N1A—C5A—C6A115.0 (3)O2'—C7'—O1'122.2 (2)
H5AA—C5A—H5AB114 (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
φ1φ2φ3φ4φ5θ
1BZMD104.1-63.9-94.9178.6-10.6
2BZMDH100.9-66.4-178.4179.5-6.3
3SLC111.0-70.2-170.8177.47.33.8
43,5DBA110.3-67.7-169.5-168.7-11.85.7
5RES106.6-59.8-174.0-171.86.530.3
6NAF105.6-68.8170.5178.39.06.9
73,5DBA105.4-63.4-159.1179.47.4/10.983.7
8RES105.1-71.5-169.1175.63.731.6
93,5DBA104.0-63.6-171.5-178.617.889.9
10ABN103.6-62.5178.6-179.1-3.113.2
11FMA103.3-70.5-169.6175.93.822.6
12MLN102.9-61.5-173.2-172.97.522.8/29.3
132,6DBA102.4-73.5-177.2178.43.45.5
143,5DNZ99.8-65.5-173.9-178.020.275.4
15IAC99.8-65.9-168.4177.14.420.4
16MAC94.5-171.081.6171.2-10.45.1
17BZC-82.9-63.0159.2-178.2-11.017.5
18MLC-72.7-66.798.1170.2-14.759.9
 

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