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
| Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619003838/jx3032sup1.cif Contains datablocks bzmdbzc, bzmdnaf, bzmdmac, bzmd35dnz, bzmdabn, bzmdslc, bzmdmlc, bzmdiac, bzmdres, bzmdfma, bzmdmln, bzmd26dba, bzmd35dba, global |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdbzcsup2.hkl Contains datablock bzmdbzc |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdnafsup3.hkl Contains datablock bzmdnaf |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdmacsup4.hkl Contains datablock bzmdmac |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmd35dnzsup5.hkl Contains datablock bzmd35dnz |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdabnsup6.hkl Contains datablock bzmdabn |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdslcsup7.hkl Contains datablock bzmdslc |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdmlcsup8.hkl Contains datablock bzmdmlc |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdiacsup9.hkl Contains datablock bzmdiac |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdressup10.hkl Contains datablock bzmdres |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdfmasup11.hkl Contains datablock bzmdfma |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmdmlnsup12.hkl Contains datablock bzmdmln |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmd26dbasup13.hkl Contains datablock bzmd26dba |
| Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdbzcsup14.cml Supplementary material |
| Structure factor file (CIF format) https://doi.org/10.1107/S2053229619003838/jx3032bzmd35dbasup14.hkl Contains datablock bzmd35dba |
| Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdnafsup15.cml Supplementary material |
| Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdmacsup16.cml Supplementary material |
| Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmd35dnzsup17.cml Supplementary material |
| Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdabnsup18.cml Supplementary material |
| Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdslcsup19.cml Supplementary material |
| Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdmlcsup20.cml Supplementary material |
| Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmdiacsup21.cml Supplementary material |
| Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619003838/jx3032bzmd26dbasup22.cml Supplementary material |
| Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619003838/jx3032sup23.pdf Hydrogen-bonding details, list of coformers and stoichiometry, and displacement ellipsoid plots |
CCDC references: 1890422; 1890421; 1890430; 1890426; 1890432; 1890427; 1890429; 1890433; 1890424; 1890423; 1890428; 1890431; 1890425
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-1
H-imidazol-1-yl)ethyl benzoate–benzoic acid (1/1) (bzmdbzc)
top
Crystal data top
C13H13N3O4·C7H6O2 | F(000) = 832 |
Mr = 397.38 | Dx = 1.366 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 13.5997 (6) Å | Cell parameters from 9997 reflections |
b = 9.0354 (4) Å | θ = 5.1–68.0° |
c = 16.5974 (8) Å | µ = 0.86 mm−1 |
β = 108.646 (2)° | T = 300 K |
V = 1932.42 (15) Å3 | Prism, clear light colourless |
Z = 4 | 0.8 × 0.2 × 0.2 mm |
Data collection top
Bruker APEXII CCD diffractometer | 2669 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.053 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 68.3°, θmin = 3.7° |
Tmin = 0.675, Tmax = 0.753 | h = −16→16 |
60527 measured reflections | k = −10→10 |
3542 independent reflections | l = −19→20 |
Refinement top
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.0462P)2 + 0.7992P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.130 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.16 e Å−3 |
3542 reflections | Δρmin = −0.14 e Å−3 |
339 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0027 (4) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Single-crystal X-ray diffraction data collection (ϕ scans
and ω scans with κ and θ offsets) were performed at room temperature on a
Bruker D8 VENTURE equipped with a Kappa goniometer, PHOTON II CPAD
detector, a Mo Kα INCOATEC IµS 3.0 microfocus source (λ =
0.71073 Å). The crystal centring, unit-cell determination, refinement of the
unit-cell parameters and data collection was controlled through the program
APEX3 (Bruker, 2012). The frame integration was performed using
SAINT (Bruker, 2016) and the intensities were scaled and absorption
corrected using SADABS (Bruker, 2001). Using OLEX2 (Dolomanov
et al., 2009), the structure was solved by intrinsic phasing using
SHELXT (Sheldrick, 2015) and refined by full-matrix least-squares
calculation based on F2 for all reflection using SHELXL
(Sheldrick, 2007). All non-H atoms were refined anisotropically. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.57161 (11) | 0.97707 (18) | 0.14818 (9) | 0.0723 (4) | |
O1' | 0.65654 (13) | 0.60123 (18) | 0.53629 (11) | 0.0806 (5) | |
N1 | 0.62802 (12) | 0.99073 (17) | 0.32969 (9) | 0.0568 (4) | |
O2' | 0.52139 (13) | 0.69513 (19) | 0.56528 (12) | 0.0887 (5) | |
N3 | 0.79953 (14) | 0.9851 (2) | 0.30460 (11) | 0.0681 (5) | |
O1 | 0.87927 (13) | 0.9118 (2) | 0.31765 (12) | 0.0933 (5) | |
N2 | 0.65260 (13) | 0.80491 (19) | 0.42084 (11) | 0.0655 (5) | |
O4 | 0.43536 (12) | 0.8503 (2) | 0.06689 (11) | 0.0930 (6) | |
O2 | 0.78341 (14) | 1.1005 (2) | 0.26413 (12) | 0.0933 (6) | |
C1' | 0.61614 (14) | 0.4999 (2) | 0.65137 (12) | 0.0543 (4) | |
C1 | 0.72512 (15) | 0.9308 (2) | 0.34107 (12) | 0.0584 (5) | |
C8 | 0.60097 (15) | 0.8057 (2) | 0.05160 (12) | 0.0605 (5) | |
C7' | 0.59173 (15) | 0.6076 (2) | 0.57987 (12) | 0.0587 (5) | |
C3 | 0.58695 (16) | 0.9091 (2) | 0.37957 (12) | 0.0587 (5) | |
C6' | 0.54581 (18) | 0.4792 (2) | 0.69523 (14) | 0.0660 (5) | |
C2' | 0.70976 (16) | 0.4248 (2) | 0.67683 (15) | 0.0670 (5) | |
C7 | 0.52666 (16) | 0.8765 (3) | 0.08774 (12) | 0.0642 (5) | |
C2 | 0.73912 (17) | 0.8177 (2) | 0.39708 (14) | 0.0660 (5) | |
C5 | 0.5730 (2) | 1.1090 (2) | 0.27249 (15) | 0.0692 (6) | |
C9 | 0.5671 (2) | 0.6840 (3) | −0.00055 (15) | 0.0765 (6) | |
C4 | 0.4827 (2) | 0.9323 (3) | 0.38706 (18) | 0.0732 (6) | |
C6 | 0.50507 (19) | 1.0484 (3) | 0.18877 (14) | 0.0755 (6) | |
C5' | 0.5698 (2) | 0.3854 (3) | 0.76467 (15) | 0.0746 (6) | |
C13 | 0.70145 (18) | 0.8566 (3) | 0.06717 (15) | 0.0725 (6) | |
C4' | 0.6644 (2) | 0.3150 (3) | 0.79135 (16) | 0.0786 (7) | |
C12 | 0.7663 (2) | 0.7852 (3) | 0.03012 (18) | 0.0836 (7) | |
C11 | 0.7312 (2) | 0.6645 (3) | −0.02131 (17) | 0.0872 (8) | |
C3' | 0.7339 (2) | 0.3331 (3) | 0.74715 (17) | 0.0807 (7) | |
C10 | 0.6321 (2) | 0.6133 (3) | −0.03665 (18) | 0.0900 (8) | |
H9 | 0.497 (2) | 0.656 (3) | −0.0102 (16) | 0.086 (7)* | |
H12 | 0.838 (2) | 0.821 (3) | 0.0425 (18) | 0.107 (9)* | |
H11 | 0.774 (2) | 0.614 (3) | −0.0500 (16) | 0.095 (8)* | |
H2' | 0.7584 (18) | 0.435 (3) | 0.6439 (14) | 0.080 (7)* | |
H4' | 0.679 (2) | 0.249 (3) | 0.8403 (18) | 0.105 (9)* | |
H6' | 0.477 (2) | 0.532 (3) | 0.6729 (15) | 0.092 (8)* | |
H5' | 0.520 (2) | 0.375 (3) | 0.7942 (16) | 0.094 (8)* | |
H3' | 0.801 (2) | 0.276 (3) | 0.7636 (18) | 0.111 (9)* | |
H13 | 0.7269 (19) | 0.943 (3) | 0.1044 (16) | 0.087 (8)* | |
H2 | 0.8006 (19) | 0.756 (3) | 0.4194 (15) | 0.083 (7)* | |
H6A | 0.450 (2) | 0.972 (3) | 0.1934 (17) | 0.101 (9)* | |
H6B | 0.468 (2) | 1.128 (3) | 0.1501 (17) | 0.098 (8)* | |
H1' | 0.647 (2) | 0.681 (4) | 0.494 (2) | 0.138 (12)* | |
H5A | 0.6277 (18) | 1.174 (3) | 0.2639 (15) | 0.081 (7)* | |
H5B | 0.5303 (18) | 1.163 (3) | 0.3013 (15) | 0.079 (7)* | |
H4A | 0.474 (2) | 0.864 (3) | 0.4331 (19) | 0.110 (9)* | |
H4B | 0.428 (2) | 0.917 (3) | 0.336 (2) | 0.109 (10)* | |
H4C | 0.476 (2) | 1.031 (4) | 0.4081 (17) | 0.102 (9)* | |
H10 | 0.608 (2) | 0.526 (4) | −0.072 (2) | 0.123 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0652 (9) | 0.0906 (11) | 0.0624 (8) | −0.0003 (8) | 0.0223 (7) | −0.0020 (8) |
O1' | 0.0944 (11) | 0.0741 (10) | 0.0880 (11) | 0.0183 (8) | 0.0497 (9) | 0.0230 (9) |
N1 | 0.0661 (10) | 0.0539 (9) | 0.0508 (8) | 0.0004 (7) | 0.0194 (7) | 0.0009 (7) |
O2' | 0.0776 (10) | 0.0867 (12) | 0.1086 (13) | 0.0266 (9) | 0.0395 (9) | 0.0356 (10) |
N3 | 0.0712 (11) | 0.0709 (11) | 0.0642 (10) | −0.0079 (9) | 0.0246 (9) | −0.0045 (9) |
O1 | 0.0775 (11) | 0.0989 (13) | 0.1149 (14) | 0.0056 (10) | 0.0466 (10) | 0.0036 (11) |
N2 | 0.0694 (10) | 0.0638 (10) | 0.0634 (10) | −0.0010 (8) | 0.0213 (8) | 0.0078 (8) |
O4 | 0.0621 (9) | 0.1282 (15) | 0.0868 (11) | −0.0115 (10) | 0.0211 (8) | −0.0059 (11) |
O2 | 0.0977 (12) | 0.0898 (12) | 0.0998 (13) | −0.0056 (10) | 0.0421 (10) | 0.0267 (10) |
C1' | 0.0576 (10) | 0.0471 (10) | 0.0568 (10) | −0.0020 (8) | 0.0164 (8) | −0.0019 (8) |
C1 | 0.0622 (11) | 0.0585 (11) | 0.0560 (11) | −0.0049 (9) | 0.0211 (9) | −0.0028 (9) |
C8 | 0.0641 (11) | 0.0678 (12) | 0.0490 (10) | −0.0042 (9) | 0.0171 (9) | 0.0126 (9) |
C7' | 0.0580 (11) | 0.0538 (11) | 0.0630 (12) | −0.0023 (9) | 0.0173 (9) | 0.0011 (9) |
C3 | 0.0682 (12) | 0.0574 (11) | 0.0519 (10) | −0.0038 (9) | 0.0211 (9) | −0.0028 (9) |
C6' | 0.0706 (13) | 0.0630 (12) | 0.0693 (13) | 0.0057 (10) | 0.0293 (11) | 0.0018 (10) |
C2' | 0.0599 (12) | 0.0633 (12) | 0.0773 (14) | 0.0022 (10) | 0.0211 (10) | 0.0091 (10) |
C7 | 0.0631 (12) | 0.0762 (14) | 0.0506 (11) | −0.0043 (10) | 0.0144 (9) | 0.0122 (10) |
C2 | 0.0655 (12) | 0.0642 (12) | 0.0668 (13) | 0.0012 (10) | 0.0192 (10) | 0.0044 (10) |
C5 | 0.0848 (15) | 0.0568 (12) | 0.0707 (14) | 0.0127 (11) | 0.0315 (12) | 0.0103 (10) |
C9 | 0.0744 (15) | 0.0848 (16) | 0.0674 (13) | −0.0092 (13) | 0.0188 (11) | 0.0021 (12) |
C4 | 0.0734 (14) | 0.0808 (16) | 0.0712 (15) | 0.0014 (12) | 0.0311 (12) | 0.0003 (13) |
C6 | 0.0740 (14) | 0.0941 (17) | 0.0592 (12) | 0.0181 (13) | 0.0223 (11) | 0.0103 (12) |
C5' | 0.0915 (16) | 0.0737 (14) | 0.0683 (13) | 0.0026 (12) | 0.0394 (13) | 0.0054 (11) |
C13 | 0.0696 (13) | 0.0772 (15) | 0.0733 (14) | −0.0081 (12) | 0.0263 (11) | 0.0079 (12) |
C4' | 0.0926 (17) | 0.0731 (15) | 0.0672 (14) | 0.0018 (13) | 0.0215 (12) | 0.0134 (12) |
C12 | 0.0728 (15) | 0.0937 (19) | 0.0905 (17) | −0.0004 (13) | 0.0351 (13) | 0.0171 (15) |
C11 | 0.100 (2) | 0.0925 (19) | 0.0790 (16) | 0.0190 (16) | 0.0419 (15) | 0.0129 (14) |
C3' | 0.0693 (14) | 0.0779 (15) | 0.0886 (16) | 0.0102 (12) | 0.0165 (12) | 0.0210 (13) |
C10 | 0.100 (2) | 0.0892 (19) | 0.0812 (17) | 0.0005 (16) | 0.0299 (15) | −0.0058 (14) |
Geometric parameters (Å, º) top
O3—C7 | 1.347 (3) | C1'—C2' | 1.384 (3) |
O3—C6 | 1.441 (3) | C1—C2 | 1.353 (3) |
O1'—C7' | 1.308 (2) | C8—C7 | 1.476 (3) |
N1—C1 | 1.383 (2) | C8—C9 | 1.384 (3) |
N1—C3 | 1.355 (2) | C8—C13 | 1.386 (3) |
N1—C5 | 1.466 (3) | C3—C4 | 1.477 (3) |
O2'—C7' | 1.205 (2) | C6'—C5' | 1.383 (3) |
N3—O1 | 1.230 (2) | C2'—C3' | 1.382 (3) |
N3—O2 | 1.221 (2) | C5—C6 | 1.504 (3) |
N3—C1 | 1.422 (3) | C9—C10 | 1.374 (4) |
N2—C3 | 1.327 (3) | C5'—C4' | 1.376 (3) |
N2—C2 | 1.360 (3) | C13—C12 | 1.385 (4) |
O4—C7 | 1.201 (2) | C4'—C3' | 1.379 (4) |
C1'—C7' | 1.488 (3) | C12—C11 | 1.373 (4) |
C1'—C6' | 1.387 (3) | C11—C10 | 1.370 (4) |
| | | |
C7—O3—C6 | 116.51 (17) | N1—C3—C4 | 124.6 (2) |
C1—N1—C5 | 129.89 (17) | N2—C3—N1 | 111.14 (17) |
C3—N1—C1 | 105.40 (16) | N2—C3—C4 | 124.22 (19) |
C3—N1—C5 | 124.57 (18) | C5'—C6'—C1' | 120.1 (2) |
O1—N3—C1 | 116.53 (19) | C3'—C2'—C1' | 119.9 (2) |
O2—N3—O1 | 123.4 (2) | O3—C7—C8 | 112.86 (17) |
O2—N3—C1 | 120.10 (19) | O4—C7—O3 | 121.9 (2) |
C3—N2—C2 | 106.95 (17) | O4—C7—C8 | 125.2 (2) |
C6'—C1'—C7' | 119.43 (18) | C1—C2—N2 | 108.58 (19) |
C2'—C1'—C7' | 120.86 (18) | N1—C5—C6 | 111.62 (19) |
C2'—C1'—C6' | 119.65 (19) | C10—C9—C8 | 120.7 (2) |
N1—C1—N3 | 125.81 (18) | O3—C6—C5 | 107.62 (19) |
C2—C1—N1 | 107.93 (18) | C4'—C5'—C6' | 119.9 (2) |
C2—C1—N3 | 126.15 (19) | C12—C13—C8 | 119.5 (3) |
C9—C8—C7 | 117.7 (2) | C5'—C4'—C3' | 120.2 (2) |
C9—C8—C13 | 119.5 (2) | C11—C12—C13 | 120.1 (3) |
C13—C8—C7 | 122.9 (2) | C10—C11—C12 | 120.6 (3) |
O1'—C7'—C1' | 113.23 (17) | C4'—C3'—C2' | 120.2 (2) |
O2'—C7'—O1' | 123.35 (19) | C11—C10—C9 | 119.6 (3) |
O2'—C7'—C1' | 123.38 (19) | | |
2-(2-Methyl-5-nitro-1
H-imidazol-1-yl)ethyl benzoate–
β-naphthol (1/1) (bzmdnaf)
top
Crystal data top
C13H13N3O4·C10H8O | F(000) = 880 |
Mr = 419.43 | Dx = 1.311 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 8.5105 (8) Å | Cell parameters from 9803 reflections |
b = 22.387 (2) Å | θ = 4.4–69.6° |
c = 11.7752 (11) Å | µ = 0.78 mm−1 |
β = 108.664 (4)° | T = 300 K |
V = 2125.4 (3) Å3 | Prism, clear light yellow |
Z = 4 | 0.42 × 0.09 × 0.07 mm |
Data collection top
Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer | 2810 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.084 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 68.3°, θmin = 4.0° |
Tmin = 0.678, Tmax = 1.000 | h = −10→10 |
39131 measured reflections | k = −26→26 |
3884 independent reflections | l = −14→13 |
Refinement top
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.058 | w = 1/[σ2(Fo2) + (0.1113P)2 + 0.4215P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.193 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.30 e Å−3 |
3884 reflections | Δρmin = −0.23 e Å−3 |
365 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0041 (7) |
Special details top
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 | x | y | z | Uiso*/Ueq | |
O3 | −0.36072 (19) | 0.49428 (7) | 0.19944 (13) | 0.0624 (4) | |
O2 | −0.2808 (2) | 0.51266 (9) | 0.57654 (16) | 0.0842 (6) | |
N1 | −0.2220 (2) | 0.58230 (8) | 0.39335 (15) | 0.0563 (4) | |
O1 | −0.0234 (3) | 0.52273 (9) | 0.68439 (16) | 0.0850 (6) | |
O1' | 0.2411 (3) | 0.70227 (10) | 0.35022 (19) | 0.0908 (6) | |
N3 | −0.1417 (3) | 0.53251 (9) | 0.59314 (17) | 0.0652 (5) | |
O4 | −0.3769 (3) | 0.39564 (9) | 0.21856 (18) | 0.0892 (6) | |
N2 | 0.0181 (2) | 0.62642 (9) | 0.40900 (18) | 0.0681 (5) | |
C1 | −0.1092 (3) | 0.56838 (9) | 0.50416 (18) | 0.0562 (5) | |
C3 | −0.1374 (3) | 0.61722 (10) | 0.3393 (2) | 0.0634 (6) | |
C8 | −0.2958 (3) | 0.43345 (12) | 0.05661 (19) | 0.0658 (6) | |
C2 | 0.0348 (3) | 0.59617 (11) | 0.5115 (2) | 0.0649 (6) | |
C7 | −0.3486 (3) | 0.43791 (11) | 0.1652 (2) | 0.0633 (6) | |
C10' | 0.4667 (3) | 0.67583 (11) | 0.5266 (2) | 0.0675 (6) | |
C5 | −0.3963 (3) | 0.56412 (11) | 0.3424 (2) | 0.0645 (6) | |
C9' | 0.6381 (3) | 0.67996 (10) | 0.5925 (2) | 0.0688 (6) | |
C1' | 0.4025 (3) | 0.70428 (11) | 0.4195 (2) | 0.0727 (7) | |
C6 | −0.4166 (3) | 0.50046 (11) | 0.3028 (2) | 0.0623 (6) | |
C9 | −0.2418 (3) | 0.48176 (15) | 0.0078 (2) | 0.0772 (7) | |
C4' | 0.7415 (3) | 0.71446 (11) | 0.5461 (3) | 0.0799 (8) | |
C4 | −0.2096 (5) | 0.64272 (17) | 0.2172 (3) | 0.0859 (8) | |
C13 | −0.2986 (4) | 0.37744 (15) | 0.0059 (2) | 0.0836 (8) | |
C8' | 0.7088 (4) | 0.65030 (14) | 0.7035 (3) | 0.0846 (8) | |
C2' | 0.5090 (5) | 0.73895 (14) | 0.3747 (4) | 0.0921 (9) | |
C3' | 0.6720 (4) | 0.74335 (14) | 0.4367 (4) | 0.0989 (11) | |
C12 | −0.2455 (5) | 0.37083 (19) | −0.0939 (3) | 0.0984 (10) | |
C11 | −0.1911 (4) | 0.4196 (2) | −0.1412 (3) | 0.0977 (10) | |
C5' | 0.9152 (4) | 0.71857 (15) | 0.6162 (5) | 0.1008 (12) | |
C10 | −0.1889 (4) | 0.47476 (19) | −0.0920 (3) | 0.0913 (9) | |
C6' | 0.9762 (5) | 0.68936 (17) | 0.7222 (4) | 0.1071 (12) | |
C7' | 0.8736 (4) | 0.65473 (17) | 0.7664 (3) | 0.0969 (10) | |
H5A | −0.448 (4) | 0.5694 (12) | 0.403 (3) | 0.082 (8)* | |
H10' | 0.394 (3) | 0.6541 (11) | 0.559 (2) | 0.070 (7)* | |
H6A | −0.540 (4) | 0.4903 (11) | 0.280 (2) | 0.076 (7)* | |
H5B | −0.448 (3) | 0.5927 (11) | 0.277 (2) | 0.071 (7)* | |
H6B | −0.355 (3) | 0.4734 (12) | 0.365 (2) | 0.071 (7)* | |
H8' | 0.629 (5) | 0.6273 (16) | 0.736 (3) | 0.125 (12)* | |
H10 | −0.146 (4) | 0.5098 (15) | −0.128 (3) | 0.112 (11)* | |
H13 | −0.341 (4) | 0.3442 (15) | 0.041 (3) | 0.096 (10)* | |
H9 | −0.246 (4) | 0.5203 (15) | 0.043 (3) | 0.095 (10)* | |
H1' | 0.180 (4) | 0.6777 (16) | 0.382 (3) | 0.107 (11)* | |
H2 | 0.134 (4) | 0.5959 (12) | 0.575 (3) | 0.083 (8)* | |
H4A | −0.132 (5) | 0.6636 (18) | 0.200 (3) | 0.122 (13)* | |
H3' | 0.751 (4) | 0.7664 (16) | 0.413 (3) | 0.113 (10)* | |
H6' | 1.104 (5) | 0.6919 (18) | 0.771 (3) | 0.133 (13)* | |
H12 | −0.249 (5) | 0.3291 (18) | −0.124 (3) | 0.124 (12)* | |
H4B | −0.267 (5) | 0.6107 (19) | 0.157 (4) | 0.138 (14)* | |
H11 | −0.150 (4) | 0.4097 (16) | −0.213 (3) | 0.120 (11)* | |
H2' | 0.458 (4) | 0.7552 (16) | 0.306 (3) | 0.102 (11)* | |
H4C | −0.304 (6) | 0.670 (2) | 0.212 (4) | 0.148 (15)* | |
H5' | 0.974 (4) | 0.7413 (15) | 0.573 (3) | 0.104 (10)* | |
H7' | 0.937 (6) | 0.634 (2) | 0.855 (5) | 0.170 (18)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0638 (9) | 0.0724 (10) | 0.0572 (8) | −0.0028 (7) | 0.0280 (7) | 0.0008 (7) |
O2 | 0.0876 (13) | 0.1041 (14) | 0.0733 (11) | −0.0111 (10) | 0.0431 (10) | 0.0035 (9) |
N1 | 0.0562 (9) | 0.0573 (10) | 0.0581 (10) | 0.0053 (8) | 0.0221 (8) | 0.0002 (8) |
O1 | 0.0934 (13) | 0.0978 (14) | 0.0590 (10) | 0.0078 (10) | 0.0177 (9) | 0.0115 (9) |
O1' | 0.0843 (13) | 0.0958 (14) | 0.0938 (13) | 0.0026 (10) | 0.0305 (11) | 0.0253 (11) |
N3 | 0.0746 (13) | 0.0691 (12) | 0.0586 (11) | 0.0051 (10) | 0.0308 (10) | −0.0026 (9) |
O4 | 0.1245 (16) | 0.0762 (11) | 0.0852 (12) | −0.0154 (10) | 0.0589 (11) | −0.0029 (9) |
N2 | 0.0683 (12) | 0.0661 (12) | 0.0741 (12) | −0.0026 (9) | 0.0287 (10) | 0.0014 (9) |
C1 | 0.0613 (12) | 0.0563 (11) | 0.0538 (11) | 0.0060 (9) | 0.0226 (9) | 0.0004 (9) |
C3 | 0.0694 (14) | 0.0577 (12) | 0.0677 (13) | 0.0034 (10) | 0.0286 (11) | 0.0043 (10) |
C8 | 0.0571 (12) | 0.0904 (17) | 0.0500 (11) | 0.0015 (11) | 0.0173 (9) | −0.0006 (10) |
C2 | 0.0649 (14) | 0.0645 (13) | 0.0660 (14) | 0.0048 (11) | 0.0219 (11) | −0.0037 (11) |
C7 | 0.0619 (13) | 0.0732 (15) | 0.0581 (12) | −0.0052 (11) | 0.0239 (10) | −0.0017 (10) |
C10' | 0.0707 (14) | 0.0613 (13) | 0.0796 (15) | −0.0055 (11) | 0.0368 (12) | −0.0040 (11) |
C5 | 0.0541 (12) | 0.0740 (15) | 0.0679 (14) | 0.0079 (11) | 0.0230 (11) | 0.0019 (11) |
C9' | 0.0758 (15) | 0.0580 (13) | 0.0816 (16) | −0.0034 (11) | 0.0381 (12) | −0.0181 (11) |
C1' | 0.0757 (16) | 0.0597 (13) | 0.0914 (17) | 0.0017 (11) | 0.0390 (14) | 0.0034 (12) |
C6 | 0.0593 (13) | 0.0755 (15) | 0.0585 (13) | −0.0031 (11) | 0.0278 (10) | −0.0014 (11) |
C9 | 0.0732 (15) | 0.103 (2) | 0.0595 (14) | −0.0112 (14) | 0.0272 (12) | −0.0008 (13) |
C4' | 0.0784 (17) | 0.0543 (13) | 0.121 (2) | −0.0065 (12) | 0.0508 (16) | −0.0169 (14) |
C4 | 0.094 (2) | 0.088 (2) | 0.0754 (17) | −0.0009 (18) | 0.0263 (16) | 0.0244 (15) |
C13 | 0.0924 (19) | 0.094 (2) | 0.0640 (15) | 0.0123 (16) | 0.0245 (14) | −0.0047 (14) |
C8' | 0.0856 (18) | 0.0873 (19) | 0.0835 (18) | −0.0045 (15) | 0.0306 (15) | −0.0211 (15) |
C2' | 0.106 (2) | 0.0732 (17) | 0.113 (2) | 0.0034 (16) | 0.057 (2) | 0.0197 (17) |
C3' | 0.096 (2) | 0.0680 (17) | 0.157 (3) | −0.0086 (15) | 0.075 (2) | 0.0096 (18) |
C12 | 0.103 (2) | 0.123 (3) | 0.0663 (16) | 0.030 (2) | 0.0229 (16) | −0.0136 (17) |
C11 | 0.0785 (18) | 0.157 (3) | 0.0607 (16) | 0.0163 (19) | 0.0268 (13) | 0.0002 (19) |
C5' | 0.083 (2) | 0.0666 (17) | 0.168 (4) | −0.0161 (15) | 0.062 (2) | −0.032 (2) |
C10 | 0.0742 (17) | 0.140 (3) | 0.0655 (16) | −0.0110 (17) | 0.0302 (13) | 0.0037 (18) |
C6' | 0.085 (2) | 0.088 (2) | 0.138 (3) | −0.0008 (18) | 0.021 (2) | −0.042 (2) |
C7' | 0.0807 (19) | 0.100 (2) | 0.104 (2) | −0.0034 (17) | 0.0213 (17) | −0.0365 (19) |
Geometric parameters (Å, º) top
O3—C7 | 1.339 (3) | C1'—C2' | 1.417 (4) |
O3—C6 | 1.448 (3) | C6—H6A | 1.02 (3) |
O2—N3 | 1.221 (3) | C6—H6B | 0.96 (3) |
N1—C1 | 1.385 (3) | C9—C10 | 1.395 (4) |
N1—C3 | 1.352 (3) | C9—H9 | 0.96 (3) |
N1—C5 | 1.468 (3) | C4'—C3' | 1.393 (5) |
O1—N3 | 1.234 (3) | C4'—C5' | 1.447 (5) |
O1'—C1' | 1.356 (3) | C4—H4A | 0.88 (4) |
O1'—H1' | 0.91 (4) | C4—H4B | 1.02 (5) |
N3—C1 | 1.416 (3) | C4—H4C | 1.00 (5) |
O4—C7 | 1.202 (3) | C13—C12 | 1.395 (4) |
N2—C3 | 1.332 (3) | C13—H13 | 0.98 (3) |
N2—C2 | 1.351 (3) | C8'—C7' | 1.364 (4) |
C1—C2 | 1.352 (3) | C8'—H8' | 1.02 (4) |
C3—C4 | 1.484 (4) | C2'—C3' | 1.348 (5) |
C8—C7 | 1.488 (3) | C2'—H2' | 0.87 (3) |
C8—C9 | 1.371 (4) | C3'—H3' | 0.95 (4) |
C8—C13 | 1.386 (4) | C12—C11 | 1.372 (5) |
C2—H2 | 0.93 (3) | C12—H12 | 1.00 (4) |
C10'—C9' | 1.419 (4) | C11—C10 | 1.362 (5) |
C10'—C1' | 1.361 (4) | C11—H11 | 1.04 (4) |
C10'—H10' | 0.95 (3) | C5'—C6' | 1.356 (6) |
C5—C6 | 1.492 (3) | C5'—H5' | 0.96 (3) |
C5—H5A | 0.95 (3) | C10—H10 | 1.01 (4) |
C5—H5B | 0.99 (3) | C6'—C7' | 1.388 (6) |
C9'—C4' | 1.406 (4) | C6'—H6' | 1.05 (4) |
C9'—C8' | 1.418 (4) | C7'—H7' | 1.11 (5) |
| | | |
C7—O3—C6 | 114.89 (17) | H6A—C6—H6B | 109 (2) |
C1—N1—C5 | 128.84 (19) | C8—C9—C10 | 120.4 (3) |
C3—N1—C1 | 105.12 (18) | C8—C9—H9 | 117.6 (19) |
C3—N1—C5 | 126.04 (19) | C10—C9—H9 | 122 (2) |
C1'—O1'—H1' | 112 (2) | C9'—C4'—C5' | 117.7 (3) |
O2—N3—O1 | 123.6 (2) | C3'—C4'—C9' | 118.7 (3) |
O2—N3—C1 | 119.8 (2) | C3'—C4'—C5' | 123.5 (3) |
O1—N3—C1 | 116.5 (2) | C3—C4—H4A | 109 (3) |
C3—N2—C2 | 105.8 (2) | C3—C4—H4B | 111 (2) |
N1—C1—N3 | 125.74 (19) | C3—C4—H4C | 112 (3) |
C2—C1—N1 | 107.28 (19) | H4A—C4—H4B | 116 (3) |
C2—C1—N3 | 127.0 (2) | H4A—C4—H4C | 107 (4) |
N1—C3—C4 | 124.1 (2) | H4B—C4—H4C | 101 (4) |
N2—C3—N1 | 111.9 (2) | C8—C13—C12 | 119.5 (3) |
N2—C3—C4 | 124.0 (2) | C8—C13—H13 | 117.7 (19) |
C9—C8—C7 | 122.8 (2) | C12—C13—H13 | 122.7 (19) |
C9—C8—C13 | 119.7 (2) | C9'—C8'—H8' | 116 (2) |
C13—C8—C7 | 117.5 (2) | C7'—C8'—C9' | 121.7 (3) |
N2—C2—C1 | 109.9 (2) | C7'—C8'—H8' | 122 (2) |
N2—C2—H2 | 121.8 (18) | C1'—C2'—H2' | 113 (2) |
C1—C2—H2 | 128.3 (18) | C3'—C2'—C1' | 120.5 (3) |
O3—C7—C8 | 113.3 (2) | C3'—C2'—H2' | 126 (2) |
O4—C7—O3 | 122.5 (2) | C4'—C3'—H3' | 113 (2) |
O4—C7—C8 | 124.2 (2) | C2'—C3'—C4' | 121.7 (3) |
C9'—C10'—H10' | 119.9 (15) | C2'—C3'—H3' | 125 (2) |
C1'—C10'—C9' | 120.9 (2) | C13—C12—H12 | 115 (2) |
C1'—C10'—H10' | 119.1 (15) | C11—C12—C13 | 120.0 (3) |
N1—C5—C6 | 113.15 (19) | C11—C12—H12 | 125 (2) |
N1—C5—H5A | 107.8 (17) | C12—C11—H11 | 114 (2) |
N1—C5—H5B | 106.3 (14) | C10—C11—C12 | 120.6 (3) |
C6—C5—H5A | 108.5 (17) | C10—C11—H11 | 125 (2) |
C6—C5—H5B | 113.1 (14) | C4'—C5'—H5' | 110 (2) |
H5A—C5—H5B | 108 (2) | C6'—C5'—C4' | 121.0 (3) |
C4'—C9'—C10' | 119.0 (3) | C6'—C5'—H5' | 129 (2) |
C4'—C9'—C8' | 118.8 (3) | C9—C10—H10 | 121 (2) |
C8'—C9'—C10' | 122.2 (2) | C11—C10—C9 | 119.8 (3) |
O1'—C1'—C10' | 124.8 (2) | C11—C10—H10 | 119 (2) |
O1'—C1'—C2' | 116.1 (3) | C5'—C6'—C7' | 120.9 (4) |
C10'—C1'—C2' | 119.1 (3) | C5'—C6'—H6' | 120 (2) |
O3—C6—C5 | 108.53 (19) | C7'—C6'—H6' | 119 (2) |
O3—C6—H6A | 110.0 (15) | C8'—C7'—C6' | 119.9 (4) |
O3—C6—H6B | 109.4 (15) | C8'—C7'—H7' | 126 (3) |
C5—C6—H6A | 107.5 (14) | C6'—C7'—H7' | 114 (3) |
C5—C6—H6B | 112.5 (15) | | |
2-(2-Methyl-5-nitro-1
H-imidazol-1-yl)ethyl benzoate–4-methoxybenzoic
acid (1/1) (bzmdmac)
top
Crystal data top
C13H13N3O4·C8H8O3 | Z = 2 |
Mr = 427.41 | F(000) = 448 |
Triclinic, P1 | Dx = 1.416 Mg m−3 |
a = 9.1309 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1274 (4) Å | Cell parameters from 9919 reflections |
c = 11.8538 (5) Å | θ = 2.5–27.5° |
α = 107.365 (1)° | µ = 0.11 mm−1 |
β = 103.270 (1)° | T = 300 K |
γ = 110.091 (1)° | Plate, clear light colourless |
V = 1002.73 (7) Å3 | 0.73 × 0.49 × 0.21 mm |
Data collection top
Bruker APEX3 microsource diffractometer | 3795 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.063 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 27.5°, θmin = 3.6° |
Tmin = 0.587, Tmax = 0.746 | h = −11→11 |
32021 measured reflections | k = −14→14 |
4583 independent reflections | l = −15→15 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | All H-atom parameters refined |
wR(F2) = 0.165 | w = 1/[σ2(Fo2) + (0.0785P)2 + 0.4129P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
4583 reflections | Δρmax = 0.76 e Å−3 |
364 parameters | Δρmin = −0.24 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Single-crystal X-ray diffraction data collection (ϕ scans
and ω scans with κ and θ offsets) were performed at room temperature on a
Bruker AXS D8 VENTURE equipped with a Kappa goniometer, PHOTON II CPAD
detector, a Mo Kα INCOATEC IµS 3.0 microfocus source (λ =
0.71073 Å). The crystal centring, unit-cell determination, refinement of the
unit-cell parameters and data collection was controlled through the program
APEX3 (Bruker, 2012). The frame integration was performed using
SAINT (Bruker, 2016) and the intensities were scaled and absorption
corrected using SADABS (Bruker, 2001). Using OLEX2 (Dolomanov
et al., 2009), the structure was solved by intrinsic phasing using
SHELXT (Sheldrick, 2015) and refined by full-matrix least-squares
calculation based on F2 for all reflection using SHELXL
(Sheldrick, 2007). All non-H atoms were refined anisotropically. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.25372 (18) | 0.92488 (15) | 0.54618 (12) | 0.0501 (3) | |
O1' | 0.8663 (2) | 0.60162 (19) | 0.82192 (14) | 0.0593 (4) | |
O3' | 1.3864 (2) | 0.35358 (17) | 0.84208 (14) | 0.0603 (4) | |
O2' | 0.8625 (2) | 0.56494 (18) | 0.62520 (14) | 0.0617 (4) | |
O4 | 0.3621 (2) | 0.82888 (18) | 0.41261 (14) | 0.0592 (4) | |
O2 | 0.2647 (2) | 0.86239 (18) | 0.88018 (15) | 0.0624 (4) | |
O1 | 0.4097 (2) | 0.84360 (19) | 1.03975 (14) | 0.0675 (5) | |
N1 | 0.43006 (18) | 0.75915 (15) | 0.73271 (14) | 0.0395 (3) | |
N3 | 0.3715 (2) | 0.83160 (16) | 0.92979 (14) | 0.0442 (4) | |
N2 | 0.63325 (19) | 0.70185 (17) | 0.79998 (15) | 0.0463 (4) | |
C2' | 1.0933 (2) | 0.44853 (18) | 0.66222 (16) | 0.0404 (4) | |
C1' | 1.0392 (2) | 0.50531 (17) | 0.75630 (15) | 0.0372 (4) | |
C8 | 0.1692 (2) | 0.91266 (18) | 0.33808 (16) | 0.0395 (4) | |
C5 | 0.3002 (2) | 0.76950 (19) | 0.64032 (17) | 0.0423 (4) | |
C3' | 1.2086 (2) | 0.39608 (19) | 0.68643 (17) | 0.0420 (4) | |
C3 | 0.4572 (2) | 0.77942 (18) | 0.85787 (16) | 0.0391 (4) | |
C4' | 1.2720 (2) | 0.40079 (19) | 0.80701 (17) | 0.0418 (4) | |
C7 | 0.2705 (2) | 0.88207 (19) | 0.43220 (17) | 0.0420 (4) | |
C1 | 0.5419 (2) | 0.71451 (18) | 0.70306 (17) | 0.0403 (4) | |
C7' | 0.9147 (2) | 0.55954 (19) | 0.72677 (17) | 0.0422 (4) | |
C6' | 1.1052 (2) | 0.5099 (2) | 0.87698 (17) | 0.0434 (4) | |
C2 | 0.5799 (2) | 0.7421 (2) | 0.89668 (18) | 0.0460 (4) | |
C6 | 0.3670 (3) | 0.9180 (2) | 0.64893 (18) | 0.0482 (4) | |
C4 | 0.5590 (3) | 0.6836 (3) | 0.5775 (2) | 0.0540 (5) | |
C5' | 1.2197 (3) | 0.4587 (2) | 0.90209 (18) | 0.0474 (4) | |
C9 | 0.1616 (3) | 0.8622 (2) | 0.21389 (18) | 0.0508 (5) | |
C8' | 1.4517 (4) | 0.2998 (3) | 0.7517 (3) | 0.0650 (6) | |
C13 | 0.0911 (3) | 0.9973 (3) | 0.3722 (2) | 0.0545 (5) | |
C11 | −0.0037 (3) | 0.9767 (3) | 0.1587 (2) | 0.0651 (6) | |
C10 | 0.0749 (3) | 0.8943 (3) | 0.1246 (2) | 0.0639 (6) | |
C12 | 0.0049 (3) | 1.0293 (3) | 0.2823 (3) | 0.0670 (6) | |
H5A | 0.269 (3) | 0.702 (2) | 0.552 (2) | 0.046 (5)* | |
H5B | 0.194 (3) | 0.744 (2) | 0.6573 (19) | 0.041 (5)* | |
H6A | 0.480 (3) | 0.942 (2) | 0.640 (2) | 0.055 (6)* | |
H6B | 0.373 (3) | 0.985 (2) | 0.734 (2) | 0.054 (6)* | |
H6' | 1.069 (3) | 0.549 (2) | 0.941 (2) | 0.062 (6)* | |
H2' | 1.055 (3) | 0.446 (2) | 0.578 (2) | 0.051 (6)* | |
H4A | 0.645 (3) | 0.659 (2) | 0.577 (2) | 0.056 (6)* | |
H2 | 0.624 (3) | 0.739 (3) | 0.977 (3) | 0.070 (7)* | |
H3' | 1.243 (3) | 0.357 (2) | 0.620 (2) | 0.062 (7)* | |
H5' | 1.261 (3) | 0.460 (3) | 0.983 (3) | 0.071 (7)* | |
H8'A | 1.509 (4) | 0.375 (3) | 0.726 (3) | 0.081 (8)* | |
H9 | 0.219 (3) | 0.804 (3) | 0.190 (2) | 0.069 (7)* | |
H13 | 0.095 (3) | 1.031 (3) | 0.451 (3) | 0.066 (7)* | |
H4B | 0.458 (4) | 0.606 (3) | 0.509 (3) | 0.090 (9)* | |
H1' | 0.798 (4) | 0.636 (3) | 0.811 (3) | 0.086 (9)* | |
H4C | 0.579 (4) | 0.759 (3) | 0.556 (3) | 0.084 (9)* | |
H8'B | 1.362 (4) | 0.219 (3) | 0.681 (3) | 0.088 (9)* | |
H8'C | 1.527 (4) | 0.271 (3) | 0.796 (3) | 0.079 (8)* | |
H10 | 0.069 (4) | 0.855 (3) | 0.037 (3) | 0.096 (9)* | |
H12 | −0.045 (4) | 1.088 (3) | 0.313 (3) | 0.095 (10)* | |
H11 | −0.073 (4) | 0.990 (3) | 0.088 (3) | 0.082 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0631 (8) | 0.0679 (8) | 0.0405 (7) | 0.0422 (7) | 0.0235 (6) | 0.0306 (6) |
O1' | 0.0634 (9) | 0.0923 (11) | 0.0499 (8) | 0.0555 (9) | 0.0293 (7) | 0.0337 (8) |
O3' | 0.0698 (9) | 0.0814 (10) | 0.0511 (8) | 0.0548 (8) | 0.0214 (7) | 0.0307 (7) |
O2' | 0.0699 (9) | 0.0916 (11) | 0.0458 (8) | 0.0558 (9) | 0.0213 (7) | 0.0333 (8) |
O4 | 0.0709 (9) | 0.0877 (10) | 0.0554 (8) | 0.0566 (9) | 0.0350 (7) | 0.0419 (8) |
O2 | 0.0763 (10) | 0.0866 (11) | 0.0602 (9) | 0.0601 (9) | 0.0375 (8) | 0.0386 (8) |
O1 | 0.0819 (11) | 0.0950 (12) | 0.0368 (7) | 0.0490 (10) | 0.0272 (7) | 0.0260 (8) |
N1 | 0.0455 (7) | 0.0473 (8) | 0.0370 (7) | 0.0274 (6) | 0.0182 (6) | 0.0213 (6) |
N3 | 0.0501 (8) | 0.0473 (8) | 0.0407 (8) | 0.0245 (7) | 0.0208 (7) | 0.0187 (6) |
N2 | 0.0451 (8) | 0.0586 (9) | 0.0472 (8) | 0.0310 (7) | 0.0185 (7) | 0.0265 (7) |
C2' | 0.0439 (9) | 0.0471 (9) | 0.0325 (8) | 0.0221 (7) | 0.0136 (7) | 0.0177 (7) |
C1' | 0.0361 (8) | 0.0417 (8) | 0.0364 (8) | 0.0177 (6) | 0.0144 (6) | 0.0178 (7) |
C8 | 0.0384 (8) | 0.0490 (9) | 0.0381 (8) | 0.0209 (7) | 0.0165 (7) | 0.0235 (7) |
C5 | 0.0425 (9) | 0.0461 (9) | 0.0400 (9) | 0.0214 (7) | 0.0145 (7) | 0.0187 (7) |
C3' | 0.0480 (9) | 0.0476 (9) | 0.0355 (8) | 0.0257 (8) | 0.0183 (7) | 0.0162 (7) |
C3 | 0.0433 (8) | 0.0438 (8) | 0.0353 (8) | 0.0216 (7) | 0.0163 (7) | 0.0186 (7) |
C4' | 0.0427 (9) | 0.0462 (9) | 0.0405 (9) | 0.0240 (7) | 0.0133 (7) | 0.0194 (7) |
C7 | 0.0463 (9) | 0.0523 (9) | 0.0405 (9) | 0.0277 (8) | 0.0205 (7) | 0.0256 (8) |
C1 | 0.0431 (9) | 0.0440 (9) | 0.0417 (9) | 0.0237 (7) | 0.0192 (7) | 0.0201 (7) |
C7' | 0.0397 (8) | 0.0483 (9) | 0.0399 (9) | 0.0215 (7) | 0.0150 (7) | 0.0174 (7) |
C6' | 0.0461 (9) | 0.0562 (10) | 0.0371 (9) | 0.0265 (8) | 0.0211 (7) | 0.0226 (8) |
C2 | 0.0468 (9) | 0.0588 (11) | 0.0402 (9) | 0.0285 (8) | 0.0152 (7) | 0.0249 (8) |
C6 | 0.0546 (11) | 0.0501 (10) | 0.0388 (9) | 0.0232 (8) | 0.0120 (8) | 0.0209 (8) |
C4 | 0.0650 (13) | 0.0688 (13) | 0.0497 (11) | 0.0431 (11) | 0.0311 (10) | 0.0287 (10) |
C5' | 0.0550 (10) | 0.0630 (11) | 0.0346 (9) | 0.0320 (9) | 0.0178 (8) | 0.0254 (8) |
C9 | 0.0606 (11) | 0.0591 (11) | 0.0383 (9) | 0.0316 (10) | 0.0186 (8) | 0.0209 (8) |
C8' | 0.0742 (15) | 0.0746 (15) | 0.0626 (14) | 0.0540 (14) | 0.0248 (12) | 0.0250 (12) |
C13 | 0.0622 (12) | 0.0804 (14) | 0.0480 (11) | 0.0464 (11) | 0.0302 (9) | 0.0363 (10) |
C11 | 0.0629 (13) | 0.0952 (17) | 0.0603 (13) | 0.0452 (13) | 0.0218 (11) | 0.0504 (13) |
C10 | 0.0773 (15) | 0.0840 (15) | 0.0384 (10) | 0.0415 (13) | 0.0187 (10) | 0.0308 (10) |
C12 | 0.0744 (15) | 0.0998 (18) | 0.0706 (15) | 0.0638 (14) | 0.0384 (12) | 0.0524 (14) |
Geometric parameters (Å, º) top
O3—C7 | 1.355 (2) | C3'—C4' | 1.391 (2) |
O3—C6 | 1.446 (2) | C3'—H3' | 0.96 (3) |
O1'—C7' | 1.320 (2) | C3—C2 | 1.355 (2) |
O1'—H1' | 0.84 (3) | C4'—C5' | 1.392 (3) |
O3'—C4' | 1.359 (2) | C1—C4 | 1.482 (3) |
O3'—C8' | 1.421 (3) | C6'—C5' | 1.369 (3) |
O2'—C7' | 1.217 (2) | C6'—H6' | 0.94 (3) |
O4—C7 | 1.204 (2) | C2—H2 | 0.97 (3) |
O2—N3 | 1.225 (2) | C6—H6A | 1.01 (2) |
O1—N3 | 1.222 (2) | C6—H6B | 1.04 (2) |
N1—C5 | 1.480 (2) | C4—H4A | 0.92 (3) |
N1—C3 | 1.381 (2) | C4—H4B | 0.97 (3) |
N1—C1 | 1.350 (2) | C4—H4C | 0.92 (3) |
N3—C3 | 1.414 (2) | C5'—H5' | 0.94 (3) |
N2—C1 | 1.331 (2) | C9—C10 | 1.382 (3) |
N2—C2 | 1.361 (2) | C9—H9 | 0.98 (3) |
C2'—C1' | 1.391 (2) | C8'—H8'A | 1.00 (3) |
C2'—C3' | 1.384 (2) | C8'—H8'B | 0.95 (3) |
C2'—H2' | 0.97 (2) | C8'—H8'C | 0.98 (3) |
C1'—C7' | 1.481 (2) | C13—C12 | 1.384 (3) |
C1'—C6' | 1.397 (2) | C13—H13 | 0.88 (3) |
C8—C7 | 1.478 (2) | C11—C10 | 1.372 (4) |
C8—C9 | 1.386 (3) | C11—C12 | 1.379 (4) |
C8—C13 | 1.388 (3) | C11—H11 | 1.01 (3) |
C5—C6 | 1.513 (3) | C10—H10 | 0.98 (3) |
C5—H5A | 1.00 (2) | C12—H12 | 0.95 (3) |
C5—H5B | 1.00 (2) | | |
| | | |
C7—O3—C6 | 115.93 (14) | C1'—C6'—H6' | 118.4 (15) |
C7'—O1'—H1' | 117 (2) | C5'—C6'—C1' | 120.87 (17) |
C4'—O3'—C8' | 118.47 (17) | C5'—C6'—H6' | 120.7 (15) |
C3—N1—C5 | 130.29 (14) | N2—C2—H2 | 122.3 (16) |
C1—N1—C5 | 123.92 (15) | C3—C2—N2 | 109.30 (16) |
C1—N1—C3 | 105.61 (14) | C3—C2—H2 | 128.3 (16) |
O2—N3—C3 | 119.27 (15) | O3—C6—C5 | 109.66 (15) |
O1—N3—O2 | 123.58 (16) | O3—C6—H6A | 109.6 (13) |
O1—N3—C3 | 117.15 (16) | O3—C6—H6B | 107.7 (12) |
C1—N2—C2 | 106.00 (15) | C5—C6—H6A | 107.2 (12) |
C1'—C2'—H2' | 121.8 (13) | C5—C6—H6B | 109.6 (12) |
C3'—C2'—C1' | 121.08 (16) | H6A—C6—H6B | 113.0 (18) |
C3'—C2'—H2' | 117.1 (13) | C1—C4—H4A | 110.3 (15) |
C2'—C1'—C7' | 119.62 (15) | C1—C4—H4B | 112.5 (18) |
C2'—C1'—C6' | 118.55 (16) | C1—C4—H4C | 111.9 (19) |
C6'—C1'—C7' | 121.83 (16) | H4A—C4—H4B | 107 (2) |
C9—C8—C7 | 118.52 (16) | H4A—C4—H4C | 109 (2) |
C9—C8—C13 | 119.36 (17) | H4B—C4—H4C | 106 (3) |
C13—C8—C7 | 121.99 (16) | C4'—C5'—H5' | 119.7 (16) |
N1—C5—C6 | 108.80 (15) | C6'—C5'—C4' | 120.21 (17) |
N1—C5—H5A | 111.9 (12) | C6'—C5'—H5' | 120.1 (16) |
N1—C5—H5B | 111.0 (11) | C8—C9—H9 | 119.7 (15) |
C6—C5—H5A | 109.4 (12) | C10—C9—C8 | 120.3 (2) |
C6—C5—H5B | 110.5 (11) | C10—C9—H9 | 120.1 (15) |
H5A—C5—H5B | 105.3 (16) | O3'—C8'—H8'A | 108.8 (17) |
C2'—C3'—C4' | 119.46 (16) | O3'—C8'—H8'B | 108.8 (19) |
C2'—C3'—H3' | 119.6 (15) | O3'—C8'—H8'C | 104.0 (17) |
C4'—C3'—H3' | 120.9 (15) | H8'A—C8'—H8'B | 111 (3) |
N1—C3—N3 | 124.90 (15) | H8'A—C8'—H8'C | 114 (2) |
C2—C3—N1 | 107.41 (15) | H8'B—C8'—H8'C | 109 (2) |
C2—C3—N3 | 127.68 (16) | C8—C13—H13 | 120.7 (17) |
O3'—C4'—C3' | 124.69 (17) | C12—C13—C8 | 120.1 (2) |
O3'—C4'—C5' | 115.47 (16) | C12—C13—H13 | 119.3 (17) |
C3'—C4'—C5' | 119.83 (16) | C10—C11—C12 | 120.4 (2) |
O3—C7—C8 | 112.45 (14) | C10—C11—H11 | 116.3 (16) |
O4—C7—O3 | 122.94 (16) | C12—C11—H11 | 123.2 (17) |
O4—C7—C8 | 124.57 (16) | C9—C10—H10 | 118.5 (19) |
N1—C1—C4 | 123.52 (16) | C11—C10—C9 | 120.0 (2) |
N2—C1—N1 | 111.65 (15) | C11—C10—H10 | 121.4 (19) |
N2—C1—C4 | 124.83 (16) | C13—C12—H12 | 115 (2) |
O1'—C7'—C1' | 113.17 (15) | C11—C12—C13 | 119.9 (2) |
O2'—C7'—O1' | 123.39 (17) | C11—C12—H12 | 125 (2) |
O2'—C7'—C1' | 123.44 (16) | | |
2-(2-Methyl-5-nitro-1
H-imidazol-1-yl)ethyl benzoate–3,5-dinitrobenzoic
acid (1/1) (bzmd35dnz)
top
Crystal data top
C13H13N3O4·C7H4N2O6 | F(000) = 1008 |
Mr = 487.39 | Dx = 1.533 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 21.0988 (13) Å | Cell parameters from 9941 reflections |
b = 8.4322 (5) Å | θ = 2.6–27.3° |
c = 12.0341 (8) Å | µ = 0.13 mm−1 |
β = 99.505 (2)° | T = 300 K |
V = 2111.6 (2) Å3 | Plate, clear light colourless |
Z = 4 | 0.46 × 0.40 × 0.06 mm |
Data collection top
Bruker APEXII CCD diffractometer | 3321 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.108 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 27.5°, θmin = 2.6° |
Tmin = 0.587, Tmax = 0.746 | h = −27→27 |
71598 measured reflections | k = −10→10 |
4820 independent reflections | l = −15→15 |
Refinement top
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.065 | w = 1/[σ2(Fo2) + (0.0808P)2 + 2.0317P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.213 | (Δ/σ)max < 0.001 |
S = 1.14 | Δρmax = 0.40 e Å−3 |
4820 reflections | Δρmin = −0.35 e Å−3 |
385 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.026 (4) |
Primary atom site location: dual | |
Special details top
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 | x | y | z | Uiso*/Ueq | |
O3 | 0.88887 (9) | 0.4296 (3) | 0.67819 (18) | 0.0501 (5) | |
O1' | 0.62334 (9) | 0.4206 (3) | 0.8640 (2) | 0.0519 (6) | |
O6' | 0.41665 (11) | 0.3221 (3) | 0.9795 (2) | 0.0617 (7) | |
O2' | 0.62851 (10) | 0.6000 (3) | 0.7300 (2) | 0.0691 (8) | |
N1 | 0.84690 (10) | 0.3243 (3) | 0.8853 (2) | 0.0403 (5) | |
O3' | 0.42660 (12) | 0.6852 (3) | 0.4624 (2) | 0.0659 (7) | |
O5' | 0.32969 (10) | 0.4181 (4) | 0.8826 (2) | 0.0672 (7) | |
O4' | 0.33601 (11) | 0.6115 (4) | 0.5067 (2) | 0.0731 (8) | |
N2 | 0.74971 (11) | 0.4037 (3) | 0.9065 (2) | 0.0485 (6) | |
N1' | 0.38764 (11) | 0.3936 (3) | 0.8979 (2) | 0.0500 (6) | |
O2 | 0.95921 (11) | 0.3723 (4) | 1.0441 (2) | 0.0787 (9) | |
O4 | 0.97119 (11) | 0.5544 (4) | 0.6211 (3) | 0.0766 (8) | |
N3 | 0.90992 (12) | 0.4399 (4) | 1.0593 (2) | 0.0521 (7) | |
O1 | 0.90695 (14) | 0.5286 (4) | 1.1385 (2) | 0.0810 (9) | |
N2' | 0.39462 (13) | 0.6237 (3) | 0.5270 (2) | 0.0533 (7) | |
C5' | 0.52600 (12) | 0.5108 (3) | 0.7595 (3) | 0.0419 (6) | |
C1' | 0.42448 (12) | 0.4538 (3) | 0.8136 (3) | 0.0419 (6) | |
C4' | 0.49473 (13) | 0.5679 (3) | 0.6577 (3) | 0.0437 (7) | |
C6' | 0.49130 (13) | 0.4515 (4) | 0.8391 (3) | 0.0427 (7) | |
C1 | 0.78368 (13) | 0.3235 (4) | 0.8418 (3) | 0.0434 (7) | |
C3' | 0.42799 (13) | 0.5640 (3) | 0.6359 (3) | 0.0436 (7) | |
C3 | 0.85199 (13) | 0.4118 (4) | 0.9835 (2) | 0.0424 (6) | |
C7' | 0.59800 (13) | 0.5155 (4) | 0.7827 (3) | 0.0461 (7) | |
C2' | 0.39175 (13) | 0.5094 (4) | 0.7128 (3) | 0.0454 (7) | |
C7 | 0.91451 (14) | 0.5258 (4) | 0.6079 (3) | 0.0493 (7) | |
C8 | 0.86719 (15) | 0.5910 (4) | 0.5147 (3) | 0.0482 (7) | |
C5 | 0.89796 (15) | 0.2510 (4) | 0.8332 (3) | 0.0493 (7) | |
C6 | 0.93347 (15) | 0.3681 (5) | 0.7725 (3) | 0.0523 (8) | |
C2 | 0.79212 (14) | 0.4589 (4) | 0.9961 (3) | 0.0480 (7) | |
C11 | 0.7809 (2) | 0.7221 (5) | 0.3390 (4) | 0.0706 (11) | |
C4 | 0.75565 (19) | 0.2433 (6) | 0.7357 (4) | 0.0639 (10) | |
C10 | 0.75929 (19) | 0.6644 (5) | 0.4327 (4) | 0.0685 (10) | |
C9 | 0.80146 (16) | 0.5962 (4) | 0.5207 (3) | 0.0569 (8) | |
C13 | 0.8889 (2) | 0.6517 (4) | 0.4218 (3) | 0.0613 (9) | |
C12 | 0.8460 (2) | 0.7149 (5) | 0.3335 (3) | 0.0718 (11) | |
H4' | 0.5171 (15) | 0.612 (4) | 0.593 (3) | 0.046 (8)* | |
H2' | 0.3449 (16) | 0.512 (4) | 0.695 (3) | 0.041 (8)* | |
H5A | 0.8774 (17) | 0.173 (4) | 0.780 (3) | 0.057 (10)* | |
H6' | 0.5098 (15) | 0.409 (4) | 0.912 (3) | 0.044 (8)* | |
H5B | 0.9296 (17) | 0.201 (4) | 0.897 (3) | 0.059 (10)* | |
H2 | 0.7782 (19) | 0.516 (5) | 1.051 (3) | 0.066 (11)* | |
H6A | 0.9522 (16) | 0.454 (4) | 0.825 (3) | 0.049 (9)* | |
H9 | 0.7866 (16) | 0.548 (4) | 0.590 (3) | 0.047 (9)* | |
H1' | 0.671 (2) | 0.429 (5) | 0.882 (3) | 0.073 (12)* | |
H6B | 0.9718 (18) | 0.319 (4) | 0.747 (3) | 0.060 (10)* | |
H13 | 0.935 (2) | 0.639 (6) | 0.419 (4) | 0.089 (14)* | |
H10 | 0.714 (2) | 0.669 (5) | 0.439 (4) | 0.084 (13)* | |
H12 | 0.866 (2) | 0.751 (6) | 0.265 (5) | 0.110 (17)* | |
H11 | 0.7488 (19) | 0.769 (5) | 0.276 (3) | 0.067 (11)* | |
H4A | 0.759 (2) | 0.131 (7) | 0.751 (4) | 0.104 (17)* | |
H4B | 0.773 (2) | 0.282 (5) | 0.668 (4) | 0.072 (12)* | |
H4C | 0.711 (3) | 0.267 (6) | 0.716 (4) | 0.099 (16)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0329 (10) | 0.0680 (14) | 0.0492 (12) | −0.0043 (9) | 0.0063 (8) | 0.0048 (10) |
O1' | 0.0273 (9) | 0.0594 (13) | 0.0677 (14) | 0.0030 (9) | 0.0035 (9) | 0.0137 (11) |
O6' | 0.0479 (12) | 0.0870 (18) | 0.0510 (13) | 0.0040 (12) | 0.0107 (10) | −0.0001 (12) |
O2' | 0.0353 (11) | 0.0812 (17) | 0.0884 (19) | −0.0069 (11) | 0.0032 (11) | 0.0323 (15) |
N1 | 0.0306 (11) | 0.0462 (13) | 0.0442 (13) | 0.0038 (9) | 0.0064 (9) | 0.0033 (10) |
O3' | 0.0580 (14) | 0.0854 (18) | 0.0528 (14) | 0.0023 (13) | 0.0047 (11) | 0.0062 (13) |
O5' | 0.0304 (11) | 0.099 (2) | 0.0742 (17) | 0.0064 (11) | 0.0144 (10) | −0.0028 (14) |
O4' | 0.0410 (12) | 0.095 (2) | 0.0752 (18) | −0.0037 (12) | −0.0136 (12) | 0.0065 (15) |
N2 | 0.0296 (11) | 0.0577 (15) | 0.0581 (16) | 0.0034 (10) | 0.0075 (11) | 0.0069 (12) |
N1' | 0.0341 (12) | 0.0632 (16) | 0.0539 (16) | 0.0018 (11) | 0.0107 (11) | −0.0132 (13) |
O2 | 0.0378 (12) | 0.124 (2) | 0.0699 (17) | 0.0138 (14) | −0.0042 (11) | −0.0054 (16) |
O4 | 0.0367 (12) | 0.104 (2) | 0.089 (2) | −0.0152 (13) | 0.0115 (12) | 0.0193 (16) |
N3 | 0.0404 (13) | 0.0696 (18) | 0.0443 (15) | −0.0002 (12) | 0.0013 (11) | 0.0053 (13) |
O1 | 0.0725 (18) | 0.109 (2) | 0.0557 (16) | 0.0028 (16) | −0.0065 (13) | −0.0216 (16) |
N2' | 0.0437 (14) | 0.0577 (16) | 0.0536 (16) | 0.0041 (12) | −0.0061 (12) | −0.0073 (13) |
C5' | 0.0296 (12) | 0.0395 (14) | 0.0551 (17) | 0.0026 (10) | 0.0029 (11) | −0.0038 (13) |
C1' | 0.0292 (12) | 0.0481 (15) | 0.0481 (16) | 0.0014 (11) | 0.0054 (11) | −0.0098 (12) |
C4' | 0.0327 (13) | 0.0443 (15) | 0.0529 (17) | 0.0021 (11) | 0.0033 (12) | −0.0045 (13) |
C6' | 0.0321 (13) | 0.0448 (15) | 0.0498 (17) | 0.0014 (11) | 0.0024 (12) | −0.0065 (13) |
C1 | 0.0313 (13) | 0.0468 (15) | 0.0514 (16) | −0.0034 (11) | 0.0048 (11) | 0.0044 (13) |
C3' | 0.0355 (14) | 0.0448 (15) | 0.0480 (16) | 0.0046 (11) | 0.0001 (12) | −0.0053 (12) |
C3 | 0.0347 (13) | 0.0499 (16) | 0.0420 (15) | 0.0029 (11) | 0.0042 (11) | 0.0082 (12) |
C7' | 0.0333 (13) | 0.0466 (16) | 0.0569 (18) | −0.0009 (12) | 0.0029 (12) | 0.0028 (14) |
C2' | 0.0305 (13) | 0.0500 (16) | 0.0542 (17) | 0.0036 (11) | 0.0027 (12) | −0.0101 (14) |
C7 | 0.0379 (14) | 0.0588 (18) | 0.0526 (18) | −0.0064 (13) | 0.0118 (13) | −0.0055 (14) |
C8 | 0.0451 (15) | 0.0503 (17) | 0.0493 (17) | −0.0048 (13) | 0.0079 (13) | −0.0066 (13) |
C5 | 0.0384 (15) | 0.0557 (18) | 0.0552 (18) | 0.0062 (13) | 0.0119 (13) | 0.0000 (15) |
C6 | 0.0348 (14) | 0.072 (2) | 0.0505 (18) | 0.0036 (14) | 0.0081 (13) | 0.0011 (16) |
C2 | 0.0408 (15) | 0.0587 (18) | 0.0456 (17) | 0.0085 (13) | 0.0100 (13) | 0.0043 (14) |
C11 | 0.081 (3) | 0.055 (2) | 0.067 (2) | 0.0016 (19) | −0.013 (2) | −0.0025 (18) |
C4 | 0.050 (2) | 0.077 (3) | 0.061 (2) | −0.0153 (18) | 0.0006 (16) | −0.0085 (19) |
C10 | 0.052 (2) | 0.063 (2) | 0.085 (3) | −0.0061 (17) | −0.0068 (19) | −0.006 (2) |
C9 | 0.0441 (17) | 0.0586 (19) | 0.066 (2) | −0.0098 (14) | 0.0048 (15) | −0.0023 (17) |
C13 | 0.065 (2) | 0.059 (2) | 0.063 (2) | 0.0035 (17) | 0.0208 (18) | 0.0003 (17) |
C12 | 0.103 (3) | 0.058 (2) | 0.055 (2) | 0.007 (2) | 0.016 (2) | 0.0025 (17) |
Geometric parameters (Å, º) top
O3—C7 | 1.347 (4) | C6'—H6' | 0.97 (3) |
O3—C6 | 1.446 (4) | C1—C4 | 1.478 (5) |
O1'—C7' | 1.308 (4) | C3'—C2' | 1.374 (4) |
O1'—H1' | 0.99 (4) | C3—C2 | 1.356 (4) |
O6'—N1' | 1.227 (4) | C2'—H2' | 0.98 (3) |
O2'—C7' | 1.208 (4) | C7—C8 | 1.479 (5) |
N1—C1 | 1.350 (3) | C8—C9 | 1.401 (4) |
N1—C3 | 1.382 (4) | C8—C13 | 1.375 (5) |
N1—C5 | 1.469 (4) | C5—C6 | 1.501 (5) |
O3'—N2' | 1.225 (4) | C5—H5A | 0.97 (4) |
O5'—N1' | 1.223 (3) | C5—H5B | 1.02 (4) |
O4'—N2' | 1.225 (3) | C6—H6A | 1.00 (4) |
N2—C1 | 1.328 (4) | C6—H6B | 1.00 (4) |
N2—C2 | 1.364 (4) | C2—H2 | 0.91 (4) |
N1'—C1' | 1.467 (4) | C11—C10 | 1.373 (6) |
O2—N3 | 1.226 (4) | C11—C12 | 1.387 (6) |
O4—C7 | 1.204 (4) | C11—H11 | 1.01 (4) |
N3—O1 | 1.221 (4) | C4—H4A | 0.97 (6) |
N3—C3 | 1.419 (4) | C4—H4B | 1.01 (4) |
N2'—C3' | 1.469 (4) | C4—H4C | 0.95 (5) |
C5'—C4' | 1.379 (4) | C10—C9 | 1.390 (5) |
C5'—C6' | 1.391 (4) | C10—H10 | 0.97 (5) |
C5'—C7' | 1.499 (4) | C9—H9 | 1.02 (3) |
C1'—C6' | 1.393 (4) | C13—C12 | 1.384 (6) |
C1'—C2' | 1.375 (4) | C13—H13 | 0.98 (4) |
C4'—C3' | 1.390 (4) | C12—H12 | 1.04 (5) |
C4'—H4' | 1.05 (3) | | |
| | | |
C7—O3—C6 | 115.6 (2) | O3—C7—C8 | 114.1 (2) |
C7'—O1'—H1' | 113 (2) | O4—C7—O3 | 122.1 (3) |
C1—N1—C3 | 105.5 (2) | O4—C7—C8 | 123.8 (3) |
C1—N1—C5 | 125.4 (3) | C9—C8—C7 | 121.5 (3) |
C3—N1—C5 | 129.1 (2) | C13—C8—C7 | 118.8 (3) |
C1—N2—C2 | 106.9 (2) | C13—C8—C9 | 119.7 (3) |
O6'—N1'—C1' | 118.2 (2) | N1—C5—C6 | 113.0 (3) |
O5'—N1'—O6' | 123.9 (3) | N1—C5—H5A | 107 (2) |
O5'—N1'—C1' | 117.9 (3) | N1—C5—H5B | 107 (2) |
O2—N3—C3 | 119.2 (3) | C6—C5—H5A | 109 (2) |
O1—N3—O2 | 123.7 (3) | C6—C5—H5B | 108 (2) |
O1—N3—C3 | 117.0 (3) | H5A—C5—H5B | 113 (3) |
O3'—N2'—C3' | 118.5 (3) | O3—C6—C5 | 107.8 (3) |
O4'—N2'—O3' | 123.6 (3) | O3—C6—H6A | 112.3 (19) |
O4'—N2'—C3' | 117.9 (3) | O3—C6—H6B | 111 (2) |
C4'—C5'—C6' | 120.5 (3) | C5—C6—H6A | 110.1 (19) |
C4'—C5'—C7' | 118.5 (3) | C5—C6—H6B | 112 (2) |
C6'—C5'—C7' | 120.9 (3) | H6A—C6—H6B | 104 (3) |
C6'—C1'—N1' | 118.4 (3) | N2—C2—H2 | 121 (2) |
C2'—C1'—N1' | 118.8 (2) | C3—C2—N2 | 108.2 (3) |
C2'—C1'—C6' | 122.8 (3) | C3—C2—H2 | 131 (3) |
C5'—C4'—C3' | 118.8 (3) | C10—C11—C12 | 119.3 (4) |
C5'—C4'—H4' | 125.4 (18) | C10—C11—H11 | 119 (2) |
C3'—C4'—H4' | 115.8 (18) | C12—C11—H11 | 122 (2) |
C5'—C6'—C1' | 118.2 (3) | C1—C4—H4A | 106 (3) |
C5'—C6'—H6' | 125.2 (18) | C1—C4—H4B | 114 (2) |
C1'—C6'—H6' | 116.6 (19) | C1—C4—H4C | 111 (3) |
N1—C1—C4 | 124.5 (3) | H4A—C4—H4B | 116 (4) |
N2—C1—N1 | 111.3 (3) | H4A—C4—H4C | 107 (4) |
N2—C1—C4 | 124.2 (3) | H4B—C4—H4C | 102 (4) |
C4'—C3'—N2' | 118.8 (3) | C11—C10—C9 | 121.0 (4) |
C2'—C3'—N2' | 118.5 (3) | C11—C10—H10 | 121 (3) |
C2'—C3'—C4' | 122.7 (3) | C9—C10—H10 | 118 (3) |
N1—C3—N3 | 125.1 (3) | C8—C9—H9 | 117.9 (19) |
C2—C3—N1 | 108.0 (3) | C10—C9—C8 | 119.2 (4) |
C2—C3—N3 | 126.7 (3) | C10—C9—H9 | 122.9 (19) |
O1'—C7'—C5' | 113.6 (3) | C8—C13—C12 | 120.3 (4) |
O2'—C7'—O1' | 124.5 (3) | C8—C13—H13 | 117 (3) |
O2'—C7'—C5' | 122.0 (3) | C12—C13—H13 | 123 (3) |
C1'—C2'—H2' | 122.6 (18) | C11—C12—H12 | 124 (3) |
C3'—C2'—C1' | 117.0 (3) | C13—C12—C11 | 120.5 (4) |
C3'—C2'—H2' | 120.4 (18) | C13—C12—H12 | 115 (3) |
2-(2-Methyl-5-nitro-1
H-imidazol-1-yl)ethyl benzoate–3-aminobenzoic
acid (1/1) (bzmdabn)
top
Crystal data top
C13H13N3O4·C7H7NO2 | Z = 2 |
Mr = 412.40 | F(000) = 432 |
Triclinic, P1 | Dx = 1.254 Mg m−3 |
a = 7.9316 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.9585 (12) Å | Cell parameters from 6174 reflections |
c = 12.1978 (12) Å | θ = 2.7–29.7° |
α = 76.362 (3)° | µ = 0.09 mm−1 |
β = 78.927 (3)° | T = 300 K |
γ = 79.583 (3)° | Plate, clear light colourless |
V = 1092.21 (18) Å3 | 0.91 × 0.09 × 0.05 mm |
Data collection top
Bruker APEXII CCD diffractometer | 2711 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.090 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 27.5°, θmin = 2.6° |
Tmin = 0.587, Tmax = 0.746 | h = −10→10 |
38219 measured reflections | k = −15→15 |
5008 independent reflections | l = −15→15 |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.168 | w = 1/[σ2(Fo2) + (0.0722P)2 + 0.2049P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
5008 reflections | Δρmax = 0.25 e Å−3 |
340 parameters | Δρmin = −0.19 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.4965 (2) | −0.14226 (17) | 0.07569 (17) | 0.0875 (6) | |
O2 | 0.2393 (2) | −0.07338 (15) | 0.03516 (16) | 0.0810 (5) | |
O3 | 0.13769 (18) | 0.29191 (12) | 0.00673 (13) | 0.0578 (4) | |
O4 | 0.1642 (3) | 0.33490 (16) | −0.18307 (15) | 0.0845 (6) | |
N1 | 0.2025 (2) | 0.08578 (15) | 0.17918 (14) | 0.0541 (4) | |
N2 | 0.3948 (3) | 0.0924 (2) | 0.28556 (17) | 0.0710 (6) | |
N3 | 0.3595 (3) | −0.07569 (17) | 0.08576 (17) | 0.0646 (5) | |
C1 | 0.3443 (3) | 0.00215 (19) | 0.15970 (18) | 0.0558 (5) | |
C2 | 0.4600 (3) | 0.0087 (3) | 0.2261 (2) | 0.0691 (7) | |
H2 | 0.569 (4) | −0.039 (2) | 0.230 (2) | 0.083 (8)* | |
C3 | 0.2405 (3) | 0.1382 (2) | 0.25590 (18) | 0.0612 (6) | |
C4 | 0.1251 (4) | 0.2346 (3) | 0.3018 (2) | 0.0881 (8) | |
H4A | 0.103783 | 0.299389 | 0.240158 | 0.132* | |
H4B | 0.179996 | 0.257855 | 0.354842 | 0.132* | |
H4C | 0.017095 | 0.208828 | 0.340157 | 0.132* | |
C5 | 0.0448 (3) | 0.1185 (2) | 0.1250 (2) | 0.0619 (6) | |
H5A | −0.003 (3) | 0.051 (2) | 0.1289 (18) | 0.063 (6)* | |
H5B | −0.040 (3) | 0.1650 (19) | 0.1716 (19) | 0.062 (6)* | |
C6 | 0.0791 (3) | 0.1848 (2) | 0.0046 (2) | 0.0604 (6) | |
H6A | 0.170 (3) | 0.141 (2) | −0.0427 (19) | 0.065 (7)* | |
H6B | −0.029 (3) | 0.204 (2) | −0.027 (2) | 0.070 (7)* | |
C7 | 0.1776 (3) | 0.3604 (2) | −0.0960 (2) | 0.0584 (5) | |
C8 | 0.2397 (3) | 0.46813 (19) | −0.0895 (2) | 0.0578 (5) | |
C9 | 0.2958 (4) | 0.5415 (2) | −0.1918 (3) | 0.0776 (7) | |
H9 | 0.294 (3) | 0.518 (2) | −0.264 (2) | 0.080 (8)* | |
C10 | 0.3595 (4) | 0.6420 (3) | −0.1898 (4) | 0.0939 (10) | |
H10 | 0.397 (5) | 0.693 (3) | −0.261 (3) | 0.130 (12)* | |
C11 | 0.3661 (4) | 0.6693 (3) | −0.0888 (4) | 0.0907 (9) | |
H11 | 0.415 (4) | 0.744 (3) | −0.091 (2) | 0.104 (9)* | |
C12 | 0.3096 (3) | 0.5983 (3) | 0.0117 (3) | 0.0803 (8) | |
H12 | 0.316 (4) | 0.613 (2) | 0.085 (3) | 0.098 (9)* | |
C13 | 0.2470 (3) | 0.4974 (2) | 0.0121 (2) | 0.0657 (6) | |
H13 | 0.210 (3) | 0.448 (2) | 0.081 (2) | 0.075 (8)* | |
O1' | 0.4959 (2) | 0.15720 (18) | 0.45717 (16) | 0.0845 (6) | |
H1' | 0.474 (4) | 0.122 (3) | 0.396 (3) | 0.122 (11)* | |
O2' | 0.7592 (3) | 0.06517 (18) | 0.41258 (17) | 0.0914 (6) | |
N1' | 1.0963 (3) | 0.1476 (3) | 0.6945 (2) | 0.0842 (7) | |
H1'A | 1.138 (4) | 0.198 (3) | 0.722 (3) | 0.110 (11)* | |
H1'B | 1.168 (4) | 0.102 (3) | 0.652 (3) | 0.095 (10)* | |
C7' | 0.6603 (3) | 0.1271 (2) | 0.4682 (2) | 0.0643 (6) | |
C1' | 0.7135 (3) | 0.1792 (2) | 0.55349 (18) | 0.0617 (6) | |
C2' | 0.6028 (4) | 0.2643 (3) | 0.6018 (2) | 0.0823 (8) | |
H2' | 0.478 (4) | 0.298 (2) | 0.574 (2) | 0.103 (9)* | |
C3' | 0.6603 (4) | 0.3099 (3) | 0.6800 (3) | 0.0954 (10) | |
H3' | 0.580 (4) | 0.379 (3) | 0.712 (3) | 0.127 (11)* | |
C4' | 0.8236 (4) | 0.2728 (3) | 0.7085 (3) | 0.0847 (8) | |
H4' | 0.872 (3) | 0.309 (2) | 0.762 (2) | 0.093 (8)* | |
C5' | 0.9352 (3) | 0.1877 (2) | 0.66121 (19) | 0.0648 (6) | |
C6' | 0.8774 (3) | 0.1406 (2) | 0.58364 (18) | 0.0582 (5) | |
H6' | 0.955 (3) | 0.073 (2) | 0.5552 (19) | 0.068 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0721 (11) | 0.0846 (13) | 0.0996 (14) | 0.0064 (10) | −0.0086 (10) | −0.0243 (11) |
O2 | 0.0819 (12) | 0.0795 (12) | 0.0981 (13) | −0.0162 (9) | −0.0341 (10) | −0.0308 (10) |
O3 | 0.0616 (9) | 0.0565 (9) | 0.0611 (9) | −0.0122 (7) | −0.0197 (7) | −0.0130 (7) |
O4 | 0.1176 (15) | 0.0857 (13) | 0.0643 (11) | −0.0287 (11) | −0.0359 (10) | −0.0148 (9) |
N1 | 0.0496 (10) | 0.0614 (11) | 0.0536 (10) | −0.0155 (8) | −0.0120 (8) | −0.0075 (8) |
N2 | 0.0744 (13) | 0.0885 (15) | 0.0583 (12) | −0.0274 (11) | −0.0234 (10) | −0.0090 (11) |
N3 | 0.0614 (12) | 0.0627 (12) | 0.0695 (12) | −0.0124 (10) | −0.0100 (10) | −0.0106 (10) |
C1 | 0.0496 (12) | 0.0627 (13) | 0.0567 (12) | −0.0138 (10) | −0.0131 (9) | −0.0073 (10) |
C2 | 0.0572 (14) | 0.0846 (18) | 0.0661 (15) | −0.0151 (13) | −0.0201 (12) | −0.0047 (13) |
C3 | 0.0686 (14) | 0.0683 (15) | 0.0503 (12) | −0.0228 (12) | −0.0090 (11) | −0.0098 (11) |
C4 | 0.105 (2) | 0.093 (2) | 0.0704 (17) | −0.0207 (17) | −0.0032 (15) | −0.0293 (15) |
C5 | 0.0464 (12) | 0.0662 (15) | 0.0762 (16) | −0.0133 (11) | −0.0165 (11) | −0.0113 (13) |
C6 | 0.0582 (13) | 0.0589 (14) | 0.0733 (15) | −0.0104 (11) | −0.0284 (12) | −0.0154 (12) |
C7 | 0.0557 (12) | 0.0619 (14) | 0.0627 (14) | −0.0050 (10) | −0.0226 (10) | −0.0149 (11) |
C8 | 0.0489 (11) | 0.0547 (13) | 0.0701 (15) | −0.0012 (9) | −0.0143 (10) | −0.0142 (11) |
C9 | 0.0828 (18) | 0.0676 (17) | 0.0798 (18) | −0.0069 (13) | −0.0178 (14) | −0.0089 (14) |
C10 | 0.092 (2) | 0.0645 (18) | 0.115 (3) | −0.0164 (15) | −0.0123 (19) | 0.0019 (19) |
C11 | 0.0734 (18) | 0.0643 (18) | 0.137 (3) | −0.0069 (14) | −0.0119 (18) | −0.032 (2) |
C12 | 0.0664 (16) | 0.0819 (19) | 0.106 (2) | −0.0073 (14) | −0.0108 (15) | −0.0497 (18) |
C13 | 0.0560 (13) | 0.0693 (16) | 0.0783 (17) | −0.0086 (11) | −0.0107 (12) | −0.0282 (14) |
O1' | 0.0754 (12) | 0.1161 (15) | 0.0759 (12) | −0.0193 (10) | −0.0249 (9) | −0.0324 (11) |
O2' | 0.0919 (13) | 0.1102 (15) | 0.0926 (13) | −0.0068 (11) | −0.0299 (11) | −0.0545 (12) |
N1' | 0.0798 (16) | 0.0992 (18) | 0.0921 (17) | −0.0008 (14) | −0.0358 (13) | −0.0468 (15) |
C7' | 0.0691 (15) | 0.0757 (16) | 0.0531 (13) | −0.0201 (12) | −0.0146 (11) | −0.0113 (12) |
C1' | 0.0692 (14) | 0.0726 (15) | 0.0482 (12) | −0.0178 (12) | −0.0107 (10) | −0.0153 (11) |
C2' | 0.0738 (17) | 0.097 (2) | 0.0850 (18) | 0.0000 (15) | −0.0232 (14) | −0.0374 (16) |
C3' | 0.087 (2) | 0.115 (2) | 0.100 (2) | 0.0085 (18) | −0.0258 (17) | −0.061 (2) |
C4' | 0.0858 (19) | 0.100 (2) | 0.0841 (19) | −0.0021 (16) | −0.0251 (15) | −0.0491 (17) |
C5' | 0.0704 (15) | 0.0771 (16) | 0.0535 (12) | −0.0120 (12) | −0.0150 (11) | −0.0209 (11) |
C6' | 0.0675 (14) | 0.0623 (14) | 0.0478 (12) | −0.0125 (11) | −0.0107 (10) | −0.0132 (10) |
Geometric parameters (Å, º) top
O1—N3 | 1.229 (3) | C9—C10 | 1.393 (4) |
O2—N3 | 1.224 (2) | C10—H10 | 0.96 (4) |
O3—C6 | 1.446 (3) | C10—C11 | 1.360 (5) |
O3—C7 | 1.341 (3) | C11—H11 | 1.02 (3) |
O4—C7 | 1.201 (3) | C11—C12 | 1.364 (5) |
N1—C1 | 1.387 (3) | C12—H12 | 0.96 (3) |
N1—C3 | 1.346 (3) | C12—C13 | 1.385 (4) |
N1—C5 | 1.474 (3) | C13—H13 | 0.94 (3) |
N2—C2 | 1.344 (3) | O1'—H1' | 1.00 (4) |
N2—C3 | 1.328 (3) | O1'—C7' | 1.312 (3) |
N3—C1 | 1.417 (3) | O2'—C7' | 1.202 (3) |
C1—C2 | 1.358 (3) | N1'—H1'A | 0.90 (3) |
C2—H2 | 0.95 (3) | N1'—H1'B | 0.89 (3) |
C3—C4 | 1.485 (4) | N1'—C5' | 1.383 (3) |
C4—H4A | 0.9600 | C7'—C1' | 1.490 (3) |
C4—H4B | 0.9600 | C1'—C2' | 1.384 (4) |
C4—H4C | 0.9600 | C1'—C6' | 1.388 (3) |
C5—H5A | 0.95 (2) | C2'—H2' | 1.08 (3) |
C5—H5B | 0.98 (2) | C2'—C3' | 1.384 (4) |
C5—C6 | 1.495 (3) | C3'—H3' | 1.05 (3) |
C6—H6A | 0.99 (2) | C3'—C4' | 1.374 (4) |
C6—H6B | 0.97 (2) | C4'—H4' | 1.02 (3) |
C7—C8 | 1.484 (3) | C4'—C5' | 1.381 (4) |
C8—C9 | 1.391 (4) | C5'—C6' | 1.391 (3) |
C8—C13 | 1.379 (3) | C6'—H6' | 1.01 (2) |
C9—H9 | 0.98 (3) | | |
| | | |
C7—O3—C6 | 115.09 (17) | C8—C9—H9 | 118.2 (15) |
C1—N1—C5 | 129.03 (19) | C8—C9—C10 | 119.7 (3) |
C3—N1—C1 | 105.68 (18) | C10—C9—H9 | 122.1 (15) |
C3—N1—C5 | 125.2 (2) | C9—C10—H10 | 119 (2) |
C3—N2—C2 | 106.95 (19) | C11—C10—C9 | 120.5 (3) |
O1—N3—C1 | 116.9 (2) | C11—C10—H10 | 121 (2) |
O2—N3—O1 | 123.5 (2) | C10—C11—H11 | 117.9 (17) |
O2—N3—C1 | 119.6 (2) | C10—C11—C12 | 120.1 (3) |
N1—C1—N3 | 125.25 (18) | C12—C11—H11 | 122.0 (17) |
C2—C1—N1 | 106.9 (2) | C11—C12—H12 | 122.7 (18) |
C2—C1—N3 | 127.8 (2) | C11—C12—C13 | 120.6 (3) |
N2—C2—C1 | 109.2 (2) | C13—C12—H12 | 116.7 (18) |
N2—C2—H2 | 125.6 (16) | C8—C13—C12 | 120.2 (3) |
C1—C2—H2 | 125.2 (16) | C8—C13—H13 | 119.1 (15) |
N1—C3—C4 | 124.6 (2) | C12—C13—H13 | 120.7 (16) |
N2—C3—N1 | 111.2 (2) | C7'—O1'—H1' | 108.1 (19) |
N2—C3—C4 | 124.2 (2) | H1'A—N1'—H1'B | 120 (3) |
C3—C4—H4A | 109.5 | C5'—N1'—H1'A | 114 (2) |
C3—C4—H4B | 109.5 | C5'—N1'—H1'B | 115.7 (19) |
C3—C4—H4C | 109.5 | O1'—C7'—C1' | 113.7 (2) |
H4A—C4—H4B | 109.5 | O2'—C7'—O1' | 122.9 (2) |
H4A—C4—H4C | 109.5 | O2'—C7'—C1' | 123.3 (2) |
H4B—C4—H4C | 109.5 | C2'—C1'—C7' | 121.1 (2) |
N1—C5—H5A | 108.9 (13) | C2'—C1'—C6' | 120.4 (2) |
N1—C5—H5B | 107.3 (13) | C6'—C1'—C7' | 118.5 (2) |
N1—C5—C6 | 112.39 (18) | C1'—C2'—H2' | 120.0 (16) |
H5A—C5—H5B | 106.2 (19) | C1'—C2'—C3' | 118.3 (3) |
C6—C5—H5A | 111.2 (13) | C3'—C2'—H2' | 121.6 (16) |
C6—C5—H5B | 110.6 (13) | C2'—C3'—H3' | 117.9 (19) |
O3—C6—C5 | 107.92 (19) | C4'—C3'—C2' | 121.2 (3) |
O3—C6—H6A | 108.7 (13) | C4'—C3'—H3' | 120.7 (19) |
O3—C6—H6B | 108.6 (14) | C3'—C4'—H4' | 122.7 (15) |
C5—C6—H6A | 111.5 (13) | C3'—C4'—C5' | 121.1 (3) |
C5—C6—H6B | 108.9 (13) | C5'—C4'—H4' | 116.1 (15) |
H6A—C6—H6B | 111.2 (19) | N1'—C5'—C6' | 121.5 (2) |
O3—C7—C8 | 113.10 (19) | C4'—C5'—N1' | 120.5 (2) |
O4—C7—O3 | 122.3 (2) | C4'—C5'—C6' | 118.0 (2) |
O4—C7—C8 | 124.6 (2) | C1'—C6'—C5' | 121.0 (2) |
C9—C8—C7 | 117.7 (2) | C1'—C6'—H6' | 121.5 (13) |
C13—C8—C7 | 123.3 (2) | C5'—C6'—H6' | 117.4 (13) |
C13—C8—C9 | 119.0 (2) | | |
2-(2-Methyl-5-nitro-1
H-imidazol-1-yl)ethyl benzoate–salicylic
acid (1/1) (bzmdslc)
top
Crystal data top
C13H13N3O4·C7H6O3 | F(000) = 864 |
Mr = 413.38 | Dx = 1.382 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5055 (6) Å | Cell parameters from 9833 reflections |
b = 31.2239 (19) Å | θ = 2.6–27.4° |
c = 6.8578 (4) Å | µ = 0.11 mm−1 |
β = 102.628 (2)° | T = 301 K |
V = 1986.2 (2) Å3 | Prismatic, colourless |
Z = 4 | 0.68 × 0.24 × 0.16 mm |
Data collection top
Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer | 3883 reflections with I > 2σ(I) |
Multilayer mirrors monochromator | Rint = 0.035 |
φ and ω scans | θmax = 27.5°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −12→12 |
Tmin = 0.706, Tmax = 0.746 | k = −40→40 |
69959 measured reflections | l = −8→8 |
4553 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | All H-atom parameters refined |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0521P)2 + 0.3493P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
4553 reflections | Δρmax = 0.17 e Å−3 |
347 parameters | Δρmin = −0.20 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.87803 (16) | 0.63094 (4) | 0.3909 (2) | 0.0887 (4) | |
O2 | 0.92555 (13) | 0.66308 (4) | 0.67677 (19) | 0.0803 (3) | |
O3 | 0.56700 (10) | 0.71973 (3) | 0.84768 (15) | 0.0583 (2) | |
O4 | 0.64060 (13) | 0.78754 (3) | 0.84757 (19) | 0.0771 (3) | |
N1 | 0.66295 (11) | 0.63293 (3) | 0.75126 (15) | 0.0468 (2) | |
N2 | 0.52072 (13) | 0.58617 (4) | 0.56128 (18) | 0.0598 (3) | |
N3 | 0.84921 (13) | 0.64050 (4) | 0.55066 (19) | 0.0603 (3) | |
C1 | 0.54094 (14) | 0.60942 (4) | 0.7272 (2) | 0.0536 (3) | |
C2 | 0.63221 (16) | 0.59466 (4) | 0.4743 (2) | 0.0564 (3) | |
H2 | 0.6423 (17) | 0.5809 (6) | 0.355 (3) | 0.073 (5)* | |
C3 | 0.71994 (14) | 0.62349 (4) | 0.58763 (18) | 0.0480 (3) | |
C4 | 0.4412 (2) | 0.60928 (8) | 0.8662 (4) | 0.0823 (5) | |
H4A | 0.478 (3) | 0.5934 (11) | 0.988 (5) | 0.159 (11)* | |
H4B | 0.427 (3) | 0.6365 (9) | 0.916 (4) | 0.135 (10)* | |
H4C | 0.360 (4) | 0.5953 (10) | 0.805 (5) | 0.156 (11)* | |
C5 | 0.72381 (16) | 0.65981 (5) | 0.92458 (19) | 0.0558 (3) | |
H5A | 0.8236 (17) | 0.6512 (5) | 0.969 (2) | 0.058 (4)* | |
H5B | 0.6706 (17) | 0.6528 (5) | 1.028 (2) | 0.064 (4)* | |
C6 | 0.71571 (16) | 0.70700 (5) | 0.8807 (2) | 0.0588 (3) | |
H6A | 0.7540 (17) | 0.7136 (5) | 0.761 (3) | 0.068 (4)* | |
C7 | 0.54390 (15) | 0.76221 (4) | 0.83503 (18) | 0.0529 (3) | |
O1' | 0.30972 (14) | 0.53009 (4) | 0.43561 (19) | 0.0822 (4) | |
H1' | 0.387 (2) | 0.5478 (7) | 0.473 (3) | 0.102 (7)* | |
O2' | 0.39947 (13) | 0.51848 (4) | 0.16738 (19) | 0.0785 (3) | |
O3' | 0.26597 (14) | 0.46438 (4) | −0.10302 (19) | 0.0787 (3) | |
H3' | 0.333 (3) | 0.4843 (7) | −0.043 (3) | 0.105 (7)* | |
C7' | 0.30950 (15) | 0.51100 (4) | 0.2653 (2) | 0.0590 (3) | |
C1' | 0.18997 (14) | 0.48065 (4) | 0.2017 (2) | 0.0519 (3) | |
C2' | 0.17227 (15) | 0.45986 (4) | 0.0179 (2) | 0.0565 (3) | |
C3' | 0.05451 (17) | 0.43294 (5) | −0.0447 (3) | 0.0659 (4) | |
H3'A | 0.0427 (19) | 0.4198 (6) | −0.172 (3) | 0.080 (5)* | |
C4' | −0.04243 (17) | 0.42646 (5) | 0.0733 (3) | 0.0686 (4) | |
H4' | −0.127 (2) | 0.4075 (6) | 0.022 (3) | 0.085 (5)* | |
C5' | −0.02454 (16) | 0.44612 (5) | 0.2583 (3) | 0.0668 (4) | |
H5' | −0.091 (2) | 0.4411 (6) | 0.340 (3) | 0.088 (6)* | |
C6' | 0.09104 (15) | 0.47294 (5) | 0.3210 (2) | 0.0597 (3) | |
H6' | 0.1065 (17) | 0.4880 (5) | 0.456 (3) | 0.073 (5)* | |
C9 | 0.28162 (16) | 0.74263 (5) | 0.7797 (2) | 0.0616 (3) | |
C10 | 0.1392 (2) | 0.75472 (7) | 0.7613 (3) | 0.0787 (5) | |
C11 | 0.1046 (2) | 0.79697 (7) | 0.7762 (3) | 0.0899 (6) | |
C12 | 0.2100 (3) | 0.82743 (7) | 0.8071 (3) | 0.0932 (6) | |
C13 | 0.3531 (2) | 0.81613 (5) | 0.8229 (2) | 0.0733 (4) | |
C8 | 0.38974 (16) | 0.77321 (4) | 0.81035 (17) | 0.0544 (3) | |
H6B | 0.7712 (18) | 0.7223 (5) | 0.994 (3) | 0.069 (4)* | |
H13 | 0.4267 (19) | 0.8361 (6) | 0.839 (3) | 0.072 (5)* | |
H9 | 0.3077 (18) | 0.7123 (5) | 0.771 (2) | 0.070 (5)* | |
H12 | 0.190 (3) | 0.8559 (8) | 0.811 (4) | 0.123 (8)* | |
H10 | 0.062 (3) | 0.7333 (8) | 0.741 (3) | 0.112 (7)* | |
H11 | 0.000 (3) | 0.8054 (7) | 0.766 (3) | 0.116 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.1115 (10) | 0.0842 (8) | 0.0896 (8) | −0.0158 (7) | 0.0642 (8) | −0.0120 (6) |
O2 | 0.0697 (7) | 0.0785 (7) | 0.0976 (8) | −0.0226 (6) | 0.0291 (6) | −0.0181 (6) |
O3 | 0.0585 (5) | 0.0463 (5) | 0.0674 (6) | −0.0003 (4) | 0.0077 (4) | −0.0079 (4) |
O4 | 0.0822 (7) | 0.0528 (6) | 0.0979 (8) | −0.0125 (5) | 0.0230 (6) | −0.0080 (5) |
N1 | 0.0541 (6) | 0.0414 (5) | 0.0460 (5) | 0.0006 (4) | 0.0134 (4) | 0.0012 (4) |
N2 | 0.0613 (7) | 0.0471 (6) | 0.0695 (7) | −0.0066 (5) | 0.0107 (5) | −0.0016 (5) |
N3 | 0.0680 (7) | 0.0500 (6) | 0.0698 (7) | −0.0058 (5) | 0.0300 (6) | −0.0020 (5) |
C1 | 0.0541 (7) | 0.0466 (6) | 0.0614 (7) | −0.0008 (5) | 0.0157 (6) | 0.0071 (5) |
C2 | 0.0697 (8) | 0.0442 (6) | 0.0557 (7) | −0.0018 (6) | 0.0148 (6) | −0.0039 (5) |
C3 | 0.0566 (7) | 0.0405 (6) | 0.0496 (6) | 0.0001 (5) | 0.0174 (5) | 0.0016 (5) |
C4 | 0.0773 (12) | 0.0870 (13) | 0.0938 (13) | −0.0075 (10) | 0.0428 (10) | 0.0071 (11) |
C5 | 0.0621 (8) | 0.0579 (8) | 0.0451 (6) | 0.0046 (6) | 0.0070 (6) | −0.0045 (5) |
C6 | 0.0568 (7) | 0.0531 (7) | 0.0638 (8) | −0.0014 (6) | 0.0072 (6) | −0.0134 (6) |
C7 | 0.0714 (8) | 0.0457 (6) | 0.0413 (6) | −0.0026 (6) | 0.0116 (5) | −0.0068 (5) |
O1' | 0.0769 (7) | 0.0870 (8) | 0.0883 (8) | −0.0321 (6) | 0.0302 (6) | −0.0276 (6) |
O2' | 0.0726 (7) | 0.0773 (7) | 0.0948 (8) | −0.0190 (6) | 0.0387 (6) | −0.0027 (6) |
O3' | 0.0817 (8) | 0.0850 (8) | 0.0804 (7) | −0.0055 (6) | 0.0414 (6) | −0.0145 (6) |
C7' | 0.0577 (7) | 0.0500 (7) | 0.0723 (9) | −0.0018 (6) | 0.0211 (6) | 0.0011 (6) |
C1' | 0.0501 (6) | 0.0414 (6) | 0.0664 (8) | 0.0038 (5) | 0.0177 (6) | 0.0003 (5) |
C2' | 0.0573 (7) | 0.0489 (7) | 0.0672 (8) | 0.0090 (5) | 0.0224 (6) | −0.0005 (6) |
C3' | 0.0641 (8) | 0.0579 (8) | 0.0750 (10) | 0.0052 (6) | 0.0136 (7) | −0.0139 (7) |
C4' | 0.0542 (8) | 0.0570 (8) | 0.0942 (11) | −0.0026 (6) | 0.0150 (7) | −0.0108 (8) |
C5' | 0.0552 (8) | 0.0628 (9) | 0.0882 (11) | −0.0045 (6) | 0.0284 (7) | −0.0056 (7) |
C6' | 0.0575 (7) | 0.0537 (7) | 0.0728 (9) | −0.0007 (6) | 0.0250 (6) | −0.0065 (6) |
C9 | 0.0675 (8) | 0.0617 (8) | 0.0529 (7) | 0.0029 (7) | 0.0076 (6) | −0.0094 (6) |
C10 | 0.0697 (10) | 0.0947 (13) | 0.0667 (9) | 0.0059 (9) | 0.0041 (8) | −0.0144 (8) |
C11 | 0.0814 (12) | 0.1051 (15) | 0.0744 (11) | 0.0296 (11) | −0.0021 (9) | −0.0137 (10) |
C12 | 0.1147 (16) | 0.0723 (11) | 0.0852 (12) | 0.0411 (11) | 0.0056 (11) | −0.0024 (9) |
C13 | 0.0964 (12) | 0.0533 (8) | 0.0661 (9) | 0.0106 (8) | 0.0089 (8) | −0.0010 (7) |
C8 | 0.0739 (8) | 0.0508 (7) | 0.0363 (6) | 0.0074 (6) | 0.0077 (5) | −0.0034 (5) |
Geometric parameters (Å, º) top
O1—N3 | 1.2229 (16) | O2'—C7' | 1.2196 (17) |
O2—N3 | 1.2236 (16) | O3'—H3' | 0.92 (2) |
O3—C6 | 1.4378 (17) | O3'—C2' | 1.3507 (17) |
O3—C7 | 1.3441 (15) | C7'—C1' | 1.4704 (19) |
O4—C7 | 1.2015 (17) | C1'—C2' | 1.3950 (19) |
N1—C1 | 1.3518 (16) | C1'—C6' | 1.3953 (19) |
N1—C3 | 1.3803 (15) | C2'—C3' | 1.391 (2) |
N1—C5 | 1.4667 (16) | C3'—H3'A | 0.951 (18) |
N2—C1 | 1.3281 (18) | C3'—C4' | 1.368 (2) |
N2—C2 | 1.3509 (19) | C4'—H4' | 1.001 (19) |
N3—C3 | 1.4116 (17) | C4'—C5' | 1.386 (2) |
C1—C4 | 1.484 (2) | C5'—H5' | 0.95 (2) |
C2—H2 | 0.948 (17) | C5'—C6' | 1.374 (2) |
C2—C3 | 1.3514 (18) | C6'—H6' | 1.019 (17) |
C4—H4A | 0.97 (3) | C9—C10 | 1.384 (2) |
C4—H4B | 0.94 (3) | C9—C8 | 1.385 (2) |
C4—H4C | 0.91 (3) | C9—H9 | 0.984 (17) |
C5—H5A | 0.969 (16) | C10—C11 | 1.369 (3) |
C5—H5B | 0.980 (16) | C10—H10 | 0.98 (2) |
C5—C6 | 1.503 (2) | C11—C12 | 1.364 (3) |
C6—H6A | 0.988 (17) | C11—H11 | 1.02 (2) |
C6—H6B | 0.965 (17) | C12—C13 | 1.386 (3) |
C7—C8 | 1.478 (2) | C12—H12 | 0.91 (2) |
O1'—H1' | 0.91 (2) | C13—C8 | 1.392 (2) |
O1'—C7' | 1.3111 (18) | C13—H13 | 0.925 (18) |
| | | |
C7—O3—C6 | 115.08 (11) | O1'—C7'—C1' | 114.06 (12) |
C1—N1—C3 | 105.29 (10) | O2'—C7'—O1' | 122.59 (14) |
C1—N1—C5 | 125.82 (11) | O2'—C7'—C1' | 123.34 (14) |
C3—N1—C5 | 128.73 (11) | C2'—C1'—C7' | 120.02 (12) |
C1—N2—C2 | 106.89 (11) | C2'—C1'—C6' | 119.06 (12) |
O1—N3—O2 | 124.02 (13) | C6'—C1'—C7' | 120.90 (13) |
O1—N3—C3 | 116.32 (12) | O3'—C2'—C1' | 122.74 (13) |
O2—N3—C3 | 119.66 (12) | O3'—C2'—C3' | 117.89 (14) |
N1—C1—C4 | 125.10 (15) | C3'—C2'—C1' | 119.37 (13) |
N2—C1—N1 | 111.15 (11) | C2'—C3'—H3'A | 118.1 (11) |
N2—C1—C4 | 123.75 (15) | C4'—C3'—C2' | 120.49 (15) |
N2—C2—H2 | 122.0 (10) | C4'—C3'—H3'A | 121.4 (11) |
N2—C2—C3 | 108.78 (12) | C3'—C4'—H4' | 118.4 (11) |
C3—C2—H2 | 129.2 (10) | C3'—C4'—C5' | 120.82 (14) |
N1—C3—N3 | 125.27 (11) | C5'—C4'—H4' | 120.7 (11) |
C2—C3—N1 | 107.88 (11) | C4'—C5'—H5' | 120.2 (12) |
C2—C3—N3 | 126.83 (12) | C6'—C5'—C4' | 119.11 (15) |
C1—C4—H4A | 113.1 (19) | C6'—C5'—H5' | 120.7 (12) |
C1—C4—H4B | 113.2 (17) | C1'—C6'—H6' | 118.1 (9) |
C1—C4—H4C | 107.7 (19) | C5'—C6'—C1' | 121.13 (14) |
H4A—C4—H4B | 102 (2) | C5'—C6'—H6' | 120.8 (9) |
H4A—C4—H4C | 105 (2) | C10—C9—C8 | 120.28 (15) |
H4B—C4—H4C | 116 (3) | C10—C9—H9 | 120.7 (10) |
N1—C5—H5A | 106.3 (9) | C8—C9—H9 | 119.0 (10) |
N1—C5—H5B | 106.4 (9) | C9—C10—H10 | 121.0 (14) |
N1—C5—C6 | 113.88 (11) | C11—C10—C9 | 120.15 (19) |
H5A—C5—H5B | 109.7 (13) | C11—C10—H10 | 118.8 (14) |
C6—C5—H5A | 109.7 (9) | C10—C11—H11 | 119.4 (13) |
C6—C5—H5B | 110.6 (9) | C12—C11—C10 | 120.21 (19) |
O3—C6—C5 | 107.94 (12) | C12—C11—H11 | 120.3 (13) |
O3—C6—H6A | 109.8 (10) | C11—C12—C13 | 120.64 (18) |
O3—C6—H6B | 109.6 (10) | C11—C12—H12 | 122.2 (17) |
C5—C6—H6A | 111.0 (9) | C13—C12—H12 | 117.1 (17) |
C5—C6—H6B | 109.3 (10) | C12—C13—C8 | 119.65 (19) |
H6A—C6—H6B | 109.1 (13) | C12—C13—H13 | 122.8 (11) |
O3—C7—C8 | 112.36 (11) | C8—C13—H13 | 117.5 (11) |
O4—C7—O3 | 122.24 (13) | C9—C8—C7 | 122.78 (12) |
O4—C7—C8 | 125.38 (12) | C9—C8—C13 | 119.05 (15) |
C7'—O1'—H1' | 111.8 (14) | C13—C8—C7 | 118.15 (14) |
C2'—O3'—H3' | 106.2 (14) | | |
1-[2-(Benzoyloxy)ethyl]-2-methyl-5-nitro-1
H-imidazol-3-ium
3-carboxyprop-2-enoate (bzmdmlc)
top
Crystal data top
C13H14N3O4+·C4H3O4− | F(000) = 1632 |
Mr = 391.33 | Dx = 1.447 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 43.130 (3) Å | Cell parameters from 6422 reflections |
b = 5.7944 (4) Å | θ = 2.7–26.1° |
c = 15.2645 (11) Å | µ = 0.12 mm−1 |
β = 109.600 (3)° | T = 302 K |
V = 3593.7 (5) Å3 | Prism, clear light colourless |
Z = 8 | 0.57 × 0.23 × 0.05 mm |
Data collection top
Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer | 2159 reflections with I > 2σ(I) |
Multilayer mirrors monochromator | Rint = 0.089 |
φ and ω scans | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −56→49 |
Tmin = 0.261, Tmax = 0.746 | k = −7→7 |
20803 measured reflections | l = −19→19 |
4130 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.056 | w = 1/[σ2(Fo2) + (0.0536P)2 + 0.8177P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.147 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.18 e Å−3 |
4130 reflections | Δρmin = −0.21 e Å−3 |
322 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0015 (3) |
Special details top
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 | x | y | z | Uiso*/Ueq | |
O3 | 0.68004 (4) | 0.6877 (3) | 0.23662 (13) | 0.0507 (5) | |
O1' | 0.55288 (4) | −0.0276 (3) | 0.21210 (14) | 0.0618 (6) | |
O4 | 0.66174 (4) | 0.3229 (3) | 0.22612 (14) | 0.0603 (5) | |
N1 | 0.61358 (4) | 0.6620 (3) | 0.25880 (13) | 0.0390 (5) | |
N2 | 0.58882 (5) | 0.3456 (4) | 0.27408 (15) | 0.0478 (5) | |
O3' | 0.45356 (6) | 0.2178 (3) | 0.08155 (16) | 0.0761 (6) | |
O2' | 0.51306 (5) | 0.2206 (3) | 0.15210 (17) | 0.0820 (7) | |
O4' | 0.41448 (5) | −0.0382 (4) | 0.03379 (16) | 0.0823 (7) | |
O2 | 0.65266 (6) | 0.9311 (4) | 0.41184 (14) | 0.0826 (7) | |
N3 | 0.64430 (5) | 0.7380 (4) | 0.42711 (17) | 0.0569 (6) | |
O1 | 0.65247 (6) | 0.6494 (4) | 0.50428 (14) | 0.0831 (7) | |
C3 | 0.62288 (6) | 0.6050 (4) | 0.35213 (17) | 0.0421 (6) | |
C1 | 0.59273 (6) | 0.4969 (4) | 0.21254 (17) | 0.0424 (6) | |
C8 | 0.71780 (6) | 0.4014 (4) | 0.31383 (17) | 0.0434 (6) | |
C7 | 0.68393 (6) | 0.4588 (4) | 0.25489 (18) | 0.0444 (6) | |
C5 | 0.62531 (7) | 0.8476 (4) | 0.2115 (2) | 0.0442 (6) | |
C2 | 0.60735 (6) | 0.4094 (4) | 0.3611 (2) | 0.0491 (7) | |
C6 | 0.64965 (7) | 0.7620 (5) | 0.1677 (2) | 0.0495 (7) | |
C13 | 0.74353 (7) | 0.5571 (5) | 0.3278 (2) | 0.0499 (7) | |
C1' | 0.52336 (7) | 0.0167 (4) | 0.1699 (2) | 0.0511 (7) | |
C2' | 0.50025 (7) | −0.1817 (4) | 0.1411 (2) | 0.0532 (7) | |
C9 | 0.72408 (7) | 0.1829 (4) | 0.35499 (19) | 0.0507 (7) | |
C4' | 0.44353 (7) | 0.0053 (5) | 0.07005 (19) | 0.0556 (7) | |
C3' | 0.46770 (7) | −0.1857 (5) | 0.1014 (2) | 0.0543 (7) | |
C12 | 0.77498 (7) | 0.4969 (5) | 0.3810 (2) | 0.0568 (7) | |
C11 | 0.78124 (8) | 0.2810 (5) | 0.4226 (2) | 0.0587 (8) | |
C10 | 0.75578 (8) | 0.1264 (5) | 0.4091 (2) | 0.0585 (8) | |
C4 | 0.57704 (9) | 0.4779 (6) | 0.1113 (2) | 0.0587 (8) | |
H5A | 0.6059 (6) | 0.907 (4) | 0.1597 (16) | 0.045 (7)* | |
H13 | 0.7388 (6) | 0.707 (4) | 0.2973 (16) | 0.052 (7)* | |
H5B | 0.6357 (5) | 0.968 (4) | 0.2571 (16) | 0.043 (7)* | |
H6A | 0.6413 (6) | 0.631 (5) | 0.1212 (18) | 0.063 (8)* | |
H2' | 0.5118 (6) | −0.330 (4) | 0.1577 (16) | 0.055 (7)* | |
H2A | 0.6072 (6) | 0.328 (4) | 0.4128 (17) | 0.048 (7)* | |
H12 | 0.7929 (7) | 0.609 (5) | 0.3919 (18) | 0.070 (9)* | |
H6B | 0.6568 (6) | 0.893 (5) | 0.1377 (19) | 0.067 (8)* | |
H10 | 0.7590 (6) | −0.031 (5) | 0.4418 (19) | 0.073 (9)* | |
H4A | 0.5560 (9) | 0.388 (6) | 0.096 (2) | 0.107 (12)* | |
H4B | 0.5743 (8) | 0.625 (6) | 0.082 (2) | 0.093 (11)* | |
H9 | 0.7040 (7) | 0.076 (5) | 0.3437 (19) | 0.077 (9)* | |
H3'A | 0.4572 (7) | −0.335 (5) | 0.0881 (19) | 0.073 (9)* | |
H2 | 0.5745 (8) | 0.206 (5) | 0.255 (2) | 0.089 (10)* | |
H11 | 0.8042 (7) | 0.243 (5) | 0.4636 (19) | 0.074 (9)* | |
H4C | 0.5910 (8) | 0.392 (6) | 0.085 (2) | 0.107 (13)* | |
H3' | 0.4806 (11) | 0.222 (6) | 0.104 (3) | 0.125 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0424 (10) | 0.0375 (9) | 0.0727 (12) | −0.0004 (8) | 0.0200 (9) | 0.0034 (8) |
O1' | 0.0417 (11) | 0.0478 (11) | 0.0899 (15) | −0.0047 (9) | 0.0142 (10) | −0.0070 (10) |
O4 | 0.0523 (11) | 0.0405 (10) | 0.0828 (14) | −0.0081 (9) | 0.0158 (10) | −0.0015 (9) |
N1 | 0.0381 (11) | 0.0325 (10) | 0.0461 (12) | −0.0026 (9) | 0.0136 (10) | −0.0003 (9) |
N2 | 0.0472 (13) | 0.0411 (12) | 0.0550 (14) | −0.0090 (10) | 0.0171 (11) | −0.0029 (11) |
O3' | 0.0631 (14) | 0.0454 (12) | 0.1100 (18) | 0.0084 (10) | 0.0160 (13) | 0.0107 (11) |
O2' | 0.0565 (13) | 0.0390 (11) | 0.140 (2) | −0.0027 (10) | 0.0187 (14) | 0.0045 (12) |
O4' | 0.0483 (13) | 0.0800 (15) | 0.1015 (17) | 0.0036 (11) | 0.0027 (12) | −0.0202 (13) |
O2 | 0.0995 (17) | 0.0666 (14) | 0.0724 (15) | −0.0391 (13) | 0.0165 (13) | −0.0087 (11) |
N3 | 0.0533 (14) | 0.0563 (14) | 0.0560 (16) | −0.0119 (12) | 0.0115 (12) | −0.0057 (12) |
O1 | 0.0933 (17) | 0.0892 (16) | 0.0482 (13) | −0.0182 (13) | −0.0010 (12) | 0.0089 (12) |
C3 | 0.0391 (14) | 0.0414 (13) | 0.0442 (15) | −0.0025 (11) | 0.0120 (12) | −0.0001 (11) |
C1 | 0.0382 (13) | 0.0389 (13) | 0.0495 (16) | −0.0009 (11) | 0.0139 (12) | −0.0009 (12) |
C8 | 0.0455 (15) | 0.0389 (13) | 0.0502 (15) | −0.0023 (11) | 0.0217 (13) | −0.0074 (11) |
C7 | 0.0493 (16) | 0.0345 (13) | 0.0566 (16) | −0.0036 (12) | 0.0273 (13) | −0.0049 (12) |
C5 | 0.0449 (15) | 0.0337 (13) | 0.0541 (17) | −0.0012 (12) | 0.0169 (14) | 0.0069 (13) |
C2 | 0.0500 (16) | 0.0452 (15) | 0.0514 (18) | −0.0066 (12) | 0.0163 (14) | 0.0037 (14) |
C6 | 0.0489 (16) | 0.0453 (15) | 0.0570 (17) | −0.0004 (13) | 0.0215 (14) | 0.0077 (14) |
C13 | 0.0472 (16) | 0.0434 (15) | 0.0611 (18) | −0.0022 (13) | 0.0208 (14) | −0.0014 (13) |
C1' | 0.0471 (16) | 0.0410 (15) | 0.0672 (19) | −0.0036 (13) | 0.0221 (14) | −0.0058 (13) |
C2' | 0.0520 (17) | 0.0337 (13) | 0.0702 (19) | −0.0014 (13) | 0.0157 (15) | −0.0083 (13) |
C9 | 0.0582 (18) | 0.0403 (14) | 0.0547 (17) | −0.0007 (14) | 0.0205 (15) | −0.0046 (12) |
C4' | 0.0481 (17) | 0.0578 (17) | 0.0555 (18) | 0.0052 (14) | 0.0101 (14) | −0.0062 (14) |
C3' | 0.0491 (17) | 0.0397 (15) | 0.0679 (19) | −0.0043 (13) | 0.0113 (14) | −0.0115 (13) |
C12 | 0.0500 (17) | 0.0546 (17) | 0.068 (2) | −0.0046 (15) | 0.0224 (15) | −0.0073 (15) |
C11 | 0.0530 (18) | 0.0646 (19) | 0.0543 (18) | 0.0110 (16) | 0.0122 (15) | −0.0082 (15) |
C10 | 0.071 (2) | 0.0482 (16) | 0.0541 (18) | 0.0090 (16) | 0.0189 (16) | −0.0020 (14) |
C4 | 0.062 (2) | 0.0612 (19) | 0.0483 (18) | −0.0114 (17) | 0.0126 (16) | −0.0067 (16) |
Geometric parameters (Å, º) top
O3—C7 | 1.354 (3) | C5—C6 | 1.505 (4) |
O3—C6 | 1.444 (3) | C5—H5A | 1.00 (2) |
O1'—C1' | 1.246 (3) | C5—H5B | 0.98 (2) |
O4—C7 | 1.202 (3) | C2—H2A | 0.92 (2) |
N1—C3 | 1.384 (3) | C6—H6A | 1.02 (3) |
N1—C1 | 1.340 (3) | C6—H6B | 0.99 (3) |
N1—C5 | 1.476 (3) | C13—C12 | 1.372 (4) |
N2—C1 | 1.336 (3) | C13—H13 | 0.97 (2) |
N2—C2 | 1.351 (3) | C1'—C2' | 1.488 (3) |
N2—H2 | 1.00 (3) | C2'—C3' | 1.330 (4) |
O3'—C4' | 1.297 (3) | C2'—H2' | 0.98 (2) |
O3'—H3' | 1.10 (4) | C9—C10 | 1.379 (4) |
O2'—C1' | 1.259 (3) | C9—H9 | 1.03 (3) |
O2'—H3' | 1.35 (4) | C4'—C3' | 1.485 (4) |
O4'—C4' | 1.214 (3) | C3'—H3'A | 0.97 (3) |
O2—N3 | 1.222 (3) | C12—C11 | 1.388 (4) |
N3—O1 | 1.223 (3) | C12—H12 | 0.98 (3) |
N3—C3 | 1.431 (3) | C11—C10 | 1.378 (4) |
C3—C2 | 1.347 (3) | C11—H11 | 1.00 (3) |
C1—C4 | 1.469 (4) | C10—H10 | 1.02 (3) |
C8—C7 | 1.474 (3) | C4—H4A | 1.00 (4) |
C8—C13 | 1.390 (3) | C4—H4B | 0.95 (3) |
C8—C9 | 1.399 (3) | C4—H4C | 0.96 (3) |
| | | |
C7—O3—C6 | 117.5 (2) | C5—C6—H6A | 114.8 (15) |
C3—N1—C5 | 130.4 (2) | C5—C6—H6B | 109.1 (15) |
C1—N1—C3 | 106.48 (19) | H6A—C6—H6B | 110 (2) |
C1—N1—C5 | 122.8 (2) | C8—C13—H13 | 118.5 (14) |
C1—N2—C2 | 109.8 (2) | C12—C13—C8 | 120.4 (3) |
C1—N2—H2 | 122.4 (17) | C12—C13—H13 | 121.0 (15) |
C2—N2—H2 | 127.8 (17) | O1'—C1'—O2' | 122.0 (2) |
C4'—O3'—H3' | 109.5 (19) | O1'—C1'—C2' | 117.4 (2) |
C1'—O2'—H3' | 110.5 (16) | O2'—C1'—C2' | 120.6 (2) |
O2—N3—O1 | 124.0 (2) | C1'—C2'—H2' | 111.7 (14) |
O2—N3—C3 | 119.5 (2) | C3'—C2'—C1' | 130.4 (3) |
O1—N3—C3 | 116.4 (2) | C3'—C2'—H2' | 117.9 (14) |
N1—C3—N3 | 125.5 (2) | C8—C9—H9 | 116.3 (15) |
C2—C3—N1 | 108.8 (2) | C10—C9—C8 | 119.2 (3) |
C2—C3—N3 | 125.6 (2) | C10—C9—H9 | 124.5 (15) |
N1—C1—C4 | 126.8 (2) | O3'—C4'—C3' | 119.8 (2) |
N2—C1—N1 | 108.6 (2) | O4'—C4'—O3' | 120.3 (3) |
N2—C1—C4 | 124.6 (2) | O4'—C4'—C3' | 119.8 (3) |
C13—C8—C7 | 121.6 (2) | C2'—C3'—C4' | 130.8 (3) |
C13—C8—C9 | 119.6 (3) | C2'—C3'—H3'A | 117.3 (17) |
C9—C8—C7 | 118.8 (2) | C4'—C3'—H3'A | 111.9 (17) |
O3—C7—C8 | 112.0 (2) | C13—C12—C11 | 120.1 (3) |
O4—C7—O3 | 122.5 (2) | C13—C12—H12 | 119.9 (16) |
O4—C7—C8 | 125.4 (2) | C11—C12—H12 | 119.9 (16) |
N1—C5—C6 | 112.4 (2) | C12—C11—H11 | 119.0 (16) |
N1—C5—H5A | 107.7 (13) | C10—C11—C12 | 119.6 (3) |
N1—C5—H5B | 108.7 (13) | C10—C11—H11 | 121.3 (16) |
C6—C5—H5A | 106.7 (13) | C9—C10—H10 | 116.6 (16) |
C6—C5—H5B | 109.2 (13) | C11—C10—C9 | 121.0 (3) |
H5A—C5—H5B | 112.1 (18) | C11—C10—H10 | 122.3 (15) |
N2—C2—H2A | 121.9 (15) | C1—C4—H4A | 110.6 (19) |
C3—C2—N2 | 106.3 (2) | C1—C4—H4B | 111.2 (19) |
C3—C2—H2A | 131.7 (15) | C1—C4—H4C | 110 (2) |
O3—C6—C5 | 111.9 (2) | H4A—C4—H4B | 113 (3) |
O3—C6—H6A | 107.9 (15) | H4A—C4—H4C | 106 (3) |
O3—C6—H6B | 102.6 (15) | H4B—C4—H4C | 106 (3) |
2-(2-Methyl-5-nitro-1
H-imidazol-1-yl)ethyl benzoate–isophthalic
acid (1/1) (bzmdiac)
top
Crystal data top
C13H13N3O4·C8H6O4 | F(000) = 920 |
Mr = 441.39 | Dx = 1.414 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8300 (3) Å | Cell parameters from 9928 reflections |
b = 33.7182 (10) Å | θ = 2.4–30.4° |
c = 7.3199 (2) Å | µ = 0.11 mm−1 |
β = 107.878 (1)° | T = 304 K |
V = 2074.13 (11) Å3 | Prism, clear light colourless |
Z = 4 | 0.95 × 0.3 × 0.11 mm |
Data collection top
Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer | 4809 reflections with I > 2σ(I) |
Multilayer mirrors monochromator | Rint = 0.037 |
φ and ω scans | θmax = 30.5°, θmin = 3.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −12→12 |
Tmin = 0.649, Tmax = 0.746 | k = −48→48 |
38842 measured reflections | l = −10→10 |
6344 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | All H-atom parameters refined |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0601P)2 + 0.4881P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
6344 reflections | Δρmax = 0.20 e Å−3 |
365 parameters | Δρmin = −0.21 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Single-crystal X-ray diffraction data collection (ϕ scans
and ω scans with κ and θ offsets) were performed at room temperature on a
Bruker AXS D8 VENTURE equipped with a Kappa goniometer, PHOTON II CPAD
detector, a Mo Kα INCOATEC IµS 3.0 microfocus source (λ =
0.71073 Å). The crystal centring, unit-cell determination, refinement of the
unit-cell parameters and data collection was controlled through the program
APEX3 (Bruker, 2012). The frame integration was performed using
SAINT (Bruker, 2016) and the intensities were scaled and absorption
corrected using SADABS (Bruker, 2001). Using OLEX2 (Dolomanov
et al., 2009), the structure was solved by intrinsic phasing using
SHELXT (Sheldrick, 2015) and refined by full-matrix least-squares
calculation based on F2 for all reflection using SHELXL
(Sheldrick, 2007). All non-H atoms were refined anisotropically. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.36882 (11) | 0.28188 (3) | −0.12385 (16) | 0.0549 (3) | |
O4' | 1.31886 (13) | 0.48005 (4) | 0.42956 (16) | 0.0617 (3) | |
O1' | 0.78049 (13) | 0.42754 (4) | 0.32394 (16) | 0.0610 (3) | |
O3' | 1.47167 (13) | 0.49211 (4) | 0.72771 (17) | 0.0697 (4) | |
N1 | 0.28442 (13) | 0.36122 (3) | −0.03743 (16) | 0.0452 (3) | |
O1 | 0.12528 (17) | 0.37021 (4) | 0.3517 (2) | 0.0760 (4) | |
N2 | 0.48973 (15) | 0.39681 (4) | 0.13450 (19) | 0.0537 (3) | |
N3 | 0.12377 (16) | 0.36110 (4) | 0.1893 (2) | 0.0550 (3) | |
O2 | 0.01225 (15) | 0.34423 (5) | 0.0737 (2) | 0.0833 (4) | |
O4 | 0.30372 (15) | 0.21816 (4) | −0.1125 (3) | 0.0846 (4) | |
O2' | 0.68960 (17) | 0.41614 (6) | 0.5685 (2) | 0.0982 (6) | |
C6' | 1.07098 (15) | 0.45287 (4) | 0.5617 (2) | 0.0431 (3) | |
C5' | 1.21363 (15) | 0.46743 (4) | 0.68527 (19) | 0.0438 (3) | |
C3 | 0.26003 (16) | 0.37089 (4) | 0.1350 (2) | 0.0440 (3) | |
C8' | 1.33969 (15) | 0.48031 (4) | 0.6041 (2) | 0.0476 (3) | |
C1' | 0.95064 (16) | 0.44156 (4) | 0.6348 (2) | 0.0455 (3) | |
C8 | 0.56805 (17) | 0.23453 (4) | −0.1057 (2) | 0.0491 (3) | |
C1 | 0.42668 (17) | 0.37765 (4) | −0.0295 (2) | 0.0507 (3) | |
C2 | 0.38648 (18) | 0.39278 (4) | 0.2375 (2) | 0.0509 (3) | |
C7 | 0.40177 (17) | 0.24289 (5) | −0.1124 (2) | 0.0526 (3) | |
C4' | 1.23414 (18) | 0.47070 (5) | 0.8801 (2) | 0.0522 (3) | |
C7' | 0.79402 (18) | 0.42688 (5) | 0.5072 (2) | 0.0539 (3) | |
C5 | 0.18737 (19) | 0.33572 (5) | −0.1921 (2) | 0.0544 (3) | |
C2' | 0.97138 (19) | 0.44485 (5) | 0.8302 (2) | 0.0552 (3) | |
C6 | 0.20736 (17) | 0.29250 (5) | −0.1403 (3) | 0.0539 (4) | |
C9 | 0.67651 (18) | 0.26461 (5) | −0.0982 (3) | 0.0578 (4) | |
C3' | 1.1133 (2) | 0.45954 (5) | 0.9526 (2) | 0.0585 (4) | |
C10 | 0.8293 (2) | 0.25530 (6) | −0.0977 (3) | 0.0664 (4) | |
C11 | 0.8741 (2) | 0.21669 (6) | −0.1068 (3) | 0.0664 (4) | |
C13 | 0.6152 (2) | 0.19536 (5) | −0.1115 (3) | 0.0669 (4) | |
C12 | 0.7681 (2) | 0.18670 (6) | −0.1130 (3) | 0.0739 (5) | |
C4 | 0.4995 (3) | 0.37538 (8) | −0.1860 (4) | 0.0781 (6) | |
H6' | 1.0525 (19) | 0.4509 (5) | 0.425 (2) | 0.049 (4)* | |
H5A | 0.219 (2) | 0.3419 (5) | −0.307 (3) | 0.059 (5)* | |
H5B | 0.077 (2) | 0.3443 (5) | −0.217 (3) | 0.060 (5)* | |
H6A | 0.138 (2) | 0.2775 (5) | −0.242 (3) | 0.062 (5)* | |
H2 | 0.405 (2) | 0.4048 (6) | 0.365 (3) | 0.066 (5)* | |
H4' | 1.335 (2) | 0.4810 (5) | 0.964 (3) | 0.059 (5)* | |
H6B | 0.187 (2) | 0.2868 (5) | −0.018 (3) | 0.060 (5)* | |
H3'A | 1.128 (2) | 0.4626 (6) | 1.089 (3) | 0.072 (5)* | |
H9 | 0.645 (2) | 0.2931 (6) | −0.091 (3) | 0.076 (6)* | |
H13 | 0.538 (3) | 0.1757 (7) | −0.116 (3) | 0.083 (6)* | |
H2' | 0.881 (2) | 0.4366 (6) | 0.884 (3) | 0.074 (6)* | |
H1' | 0.683 (3) | 0.4171 (7) | 0.249 (3) | 0.099 (7)* | |
H11 | 0.983 (3) | 0.2095 (6) | −0.109 (3) | 0.084 (6)* | |
H10 | 0.906 (3) | 0.2768 (6) | −0.092 (3) | 0.080 (6)* | |
H12 | 0.796 (3) | 0.1580 (7) | −0.126 (3) | 0.091 (7)* | |
H4A | 0.493 (4) | 0.3484 (12) | −0.248 (5) | 0.150 (12)* | |
H4B | 0.598 (5) | 0.3788 (12) | −0.136 (5) | 0.154 (14)* | |
H3' | 1.543 (4) | 0.5032 (9) | 0.655 (4) | 0.125 (9)* | |
H4C | 0.469 (5) | 0.3945 (12) | −0.266 (6) | 0.163 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0382 (5) | 0.0566 (6) | 0.0703 (7) | −0.0101 (4) | 0.0171 (5) | −0.0127 (5) |
O4' | 0.0450 (5) | 0.0863 (8) | 0.0503 (6) | −0.0193 (5) | 0.0093 (5) | −0.0118 (5) |
O1' | 0.0457 (5) | 0.0788 (8) | 0.0533 (6) | −0.0230 (5) | 0.0073 (5) | −0.0005 (5) |
O3' | 0.0412 (5) | 0.1084 (10) | 0.0535 (6) | −0.0234 (6) | 0.0055 (5) | −0.0159 (6) |
N1 | 0.0418 (5) | 0.0493 (6) | 0.0435 (6) | −0.0070 (5) | 0.0115 (4) | 0.0015 (5) |
O1 | 0.0815 (9) | 0.0851 (9) | 0.0766 (8) | −0.0039 (7) | 0.0465 (7) | −0.0137 (7) |
N2 | 0.0459 (6) | 0.0519 (7) | 0.0593 (7) | −0.0118 (5) | 0.0102 (5) | 0.0050 (5) |
N3 | 0.0505 (7) | 0.0522 (7) | 0.0681 (8) | −0.0035 (5) | 0.0269 (6) | −0.0042 (6) |
O2 | 0.0555 (7) | 0.1038 (10) | 0.0973 (10) | −0.0306 (7) | 0.0334 (7) | −0.0289 (8) |
O4 | 0.0567 (7) | 0.0643 (8) | 0.1410 (13) | −0.0193 (6) | 0.0427 (8) | −0.0104 (8) |
O2' | 0.0695 (8) | 0.1590 (15) | 0.0670 (8) | −0.0616 (9) | 0.0225 (7) | −0.0070 (9) |
C6' | 0.0385 (6) | 0.0428 (6) | 0.0438 (7) | −0.0046 (5) | 0.0067 (5) | −0.0041 (5) |
C5' | 0.0375 (6) | 0.0416 (6) | 0.0479 (7) | −0.0009 (5) | 0.0067 (5) | −0.0034 (5) |
C3 | 0.0405 (6) | 0.0434 (6) | 0.0481 (7) | −0.0028 (5) | 0.0134 (5) | 0.0009 (5) |
C8' | 0.0353 (6) | 0.0517 (7) | 0.0497 (7) | −0.0039 (5) | 0.0041 (5) | −0.0087 (6) |
C1' | 0.0413 (6) | 0.0425 (6) | 0.0497 (7) | −0.0051 (5) | 0.0092 (5) | −0.0002 (5) |
C8 | 0.0444 (7) | 0.0548 (8) | 0.0476 (7) | −0.0079 (6) | 0.0135 (6) | −0.0088 (6) |
C1 | 0.0459 (7) | 0.0529 (8) | 0.0538 (8) | −0.0077 (6) | 0.0162 (6) | 0.0088 (6) |
C2 | 0.0500 (7) | 0.0476 (7) | 0.0517 (8) | −0.0063 (6) | 0.0104 (6) | −0.0012 (6) |
C7 | 0.0454 (7) | 0.0569 (8) | 0.0566 (8) | −0.0129 (6) | 0.0170 (6) | −0.0117 (6) |
C4' | 0.0453 (7) | 0.0558 (8) | 0.0486 (7) | −0.0023 (6) | 0.0040 (6) | −0.0054 (6) |
C7' | 0.0463 (7) | 0.0564 (8) | 0.0570 (8) | −0.0159 (6) | 0.0128 (6) | 0.0003 (6) |
C5 | 0.0444 (7) | 0.0689 (9) | 0.0445 (7) | −0.0055 (7) | 0.0054 (6) | −0.0050 (6) |
C2' | 0.0510 (8) | 0.0609 (9) | 0.0536 (8) | −0.0032 (7) | 0.0158 (7) | 0.0033 (7) |
C6 | 0.0353 (6) | 0.0627 (9) | 0.0614 (9) | −0.0116 (6) | 0.0115 (6) | −0.0147 (7) |
C9 | 0.0441 (7) | 0.0587 (9) | 0.0722 (10) | −0.0089 (6) | 0.0201 (7) | −0.0106 (7) |
C3' | 0.0577 (9) | 0.0701 (10) | 0.0446 (7) | −0.0016 (7) | 0.0111 (6) | −0.0018 (7) |
C10 | 0.0454 (8) | 0.0737 (11) | 0.0820 (12) | −0.0092 (8) | 0.0224 (8) | −0.0097 (9) |
C11 | 0.0487 (8) | 0.0821 (12) | 0.0681 (10) | 0.0060 (8) | 0.0177 (8) | −0.0065 (9) |
C13 | 0.0632 (10) | 0.0555 (9) | 0.0840 (12) | −0.0094 (8) | 0.0254 (9) | −0.0075 (8) |
C12 | 0.0688 (11) | 0.0645 (11) | 0.0887 (13) | 0.0105 (9) | 0.0250 (10) | −0.0045 (9) |
C4 | 0.0825 (15) | 0.0893 (15) | 0.0776 (13) | −0.0158 (12) | 0.0468 (12) | 0.0077 (12) |
Geometric parameters (Å, º) top
O3—C7 | 1.3435 (19) | C8—C9 | 1.384 (2) |
O3—C6 | 1.4388 (17) | C8—C13 | 1.389 (2) |
O4'—C8' | 1.2338 (18) | C1—C4 | 1.478 (3) |
O1'—C7' | 1.3101 (19) | C2—H2 | 0.983 (19) |
O1'—H1' | 0.93 (3) | C4'—C3' | 1.382 (2) |
O3'—C8' | 1.2991 (16) | C4'—H4' | 0.973 (19) |
O3'—H3' | 1.02 (3) | C5—C6 | 1.502 (2) |
N1—C3 | 1.3829 (18) | C5—H5A | 0.989 (18) |
N1—C1 | 1.3578 (17) | C5—H5B | 0.976 (18) |
N1—C5 | 1.4694 (18) | C2'—C3' | 1.389 (2) |
O1—N3 | 1.2243 (18) | C2'—H2' | 1.03 (2) |
N2—C1 | 1.326 (2) | C6—H6A | 0.952 (19) |
N2—C2 | 1.357 (2) | C6—H6B | 0.988 (18) |
N3—O2 | 1.2236 (18) | C9—C10 | 1.384 (2) |
N3—C3 | 1.4171 (18) | C9—H9 | 1.01 (2) |
O4—C7 | 1.2019 (18) | C3'—H3'A | 0.97 (2) |
O2'—C7' | 1.1986 (19) | C10—C11 | 1.368 (3) |
C6'—C5' | 1.3953 (18) | C10—H10 | 0.98 (2) |
C6'—C1' | 1.3821 (19) | C11—C12 | 1.369 (3) |
C6'—H6' | 0.968 (16) | C11—H11 | 1.00 (2) |
C5'—C8' | 1.479 (2) | C13—C12 | 1.385 (3) |
C5'—C4' | 1.386 (2) | C13—H13 | 0.94 (2) |
C3—C2 | 1.3564 (19) | C12—H12 | 1.01 (2) |
C1'—C7' | 1.4955 (19) | C4—H4A | 1.01 (4) |
C1'—C2' | 1.389 (2) | C4—H4B | 0.84 (4) |
C8—C7 | 1.481 (2) | C4—H4C | 0.86 (4) |
| | | |
C7—O3—C6 | 116.03 (11) | O2'—C7'—O1' | 123.34 (14) |
C7'—O1'—H1' | 111.7 (15) | O2'—C7'—C1' | 122.45 (15) |
C8'—O3'—H3' | 108.4 (16) | N1—C5—C6 | 112.20 (13) |
C3—N1—C5 | 128.58 (12) | N1—C5—H5A | 106.5 (10) |
C1—N1—C3 | 105.42 (11) | N1—C5—H5B | 106.3 (10) |
C1—N1—C5 | 125.80 (13) | C6—C5—H5A | 112.2 (10) |
C1—N2—C2 | 106.69 (12) | C6—C5—H5B | 111.5 (10) |
O1—N3—C3 | 117.19 (13) | H5A—C5—H5B | 107.7 (15) |
O2—N3—O1 | 123.67 (14) | C1'—C2'—H2' | 120.0 (11) |
O2—N3—C3 | 119.14 (13) | C3'—C2'—C1' | 120.03 (15) |
C5'—C6'—H6' | 121.9 (10) | C3'—C2'—H2' | 119.9 (11) |
C1'—C6'—C5' | 119.62 (13) | O3—C6—C5 | 107.41 (12) |
C1'—C6'—H6' | 118.5 (10) | O3—C6—H6A | 108.6 (11) |
C6'—C5'—C8' | 118.94 (12) | O3—C6—H6B | 109.3 (11) |
C4'—C5'—C6' | 120.14 (13) | C5—C6—H6A | 108.8 (11) |
C4'—C5'—C8' | 120.90 (12) | C5—C6—H6B | 112.1 (10) |
N1—C3—N3 | 125.76 (12) | H6A—C6—H6B | 110.6 (15) |
C2—C3—N1 | 107.51 (12) | C8—C9—H9 | 120.0 (12) |
C2—C3—N3 | 126.67 (13) | C10—C9—C8 | 119.72 (16) |
O4'—C8'—O3' | 122.69 (14) | C10—C9—H9 | 120.3 (12) |
O4'—C8'—C5' | 121.51 (12) | C4'—C3'—C2' | 119.96 (15) |
O3'—C8'—C5' | 115.80 (13) | C4'—C3'—H3'A | 119.1 (12) |
C6'—C1'—C7' | 121.54 (13) | C2'—C3'—H3'A | 120.9 (12) |
C6'—C1'—C2' | 120.17 (13) | C9—C10—H10 | 119.3 (13) |
C2'—C1'—C7' | 118.26 (13) | C11—C10—C9 | 120.78 (17) |
C9—C8—C7 | 121.91 (14) | C11—C10—H10 | 119.9 (13) |
C9—C8—C13 | 119.19 (15) | C10—C11—C12 | 119.97 (17) |
C13—C8—C7 | 118.88 (14) | C10—C11—H11 | 121.8 (12) |
N1—C1—C4 | 124.24 (16) | C12—C11—H11 | 118.2 (12) |
N2—C1—N1 | 111.31 (13) | C8—C13—H13 | 116.8 (13) |
N2—C1—C4 | 124.42 (16) | C12—C13—C8 | 120.17 (17) |
N2—C2—C3 | 109.07 (13) | C12—C13—H13 | 123.1 (13) |
N2—C2—H2 | 122.9 (11) | C11—C12—C13 | 120.15 (18) |
C3—C2—H2 | 128.1 (11) | C11—C12—H12 | 121.6 (13) |
O3—C7—C8 | 112.45 (12) | C13—C12—H12 | 118.2 (13) |
O4—C7—O3 | 122.45 (14) | C1—C4—H4A | 114.7 (19) |
O4—C7—C8 | 125.08 (15) | C1—C4—H4B | 107 (2) |
C5'—C4'—H4' | 118.9 (10) | C1—C4—H4C | 112 (3) |
C3'—C4'—C5' | 120.08 (14) | H4A—C4—H4B | 103 (3) |
C3'—C4'—H4' | 121.1 (10) | H4A—C4—H4C | 114 (3) |
O1'—C7'—C1' | 114.20 (12) | H4B—C4—H4C | 105 (3) |
2-(2-Methyl-5-nitro-1
H-imidazol-1-yl)ethyl benzoate–resorcinol (2/1) (bzmdres)
top
Crystal data top
2C13H13N3O4·C6H6O2 | Dx = 1.376 Mg m−3 |
Mr = 660.63 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, Pbca | Cell parameters from 9896 reflections |
a = 26.3241 (4) Å | θ = 3.1–68.2° |
b = 7.1612 (1) Å | µ = 0.88 mm−1 |
c = 33.8433 (5) Å | T = 300 K |
V = 6379.87 (16) Å3 | Plate, clear light colourless |
Z = 8 | 0.25 × 0.12 × 0.11 mm |
F(000) = 2768 | |
Data collection top
Bruker APEXII CCD diffractometer | 4816 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.066 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 68.3°, θmin = 2.6° |
Tmin = 0.623, Tmax = 0.753 | h = −31→31 |
121051 measured reflections | k = −8→8 |
5865 independent reflections | l = −40→40 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.048 | w = 1/[σ2(Fo2) + (0.0733P)2 + 1.6636P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.147 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.30 e Å−3 |
5865 reflections | Δρmin = −0.31 e Å−3 |
540 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.00043 (6) |
Primary atom site location: dual | |
Special details top
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 | x | y | z | Uiso*/Ueq | |
O3B | 0.29177 (5) | 0.7763 (2) | 0.21878 (3) | 0.0676 (3) | |
O3A | 0.70575 (5) | −0.1189 (2) | 0.52879 (4) | 0.0691 (3) | |
N1A | 0.60485 (5) | −0.0111 (2) | 0.55009 (4) | 0.0594 (4) | |
N1B | 0.39439 (5) | 0.6490 (2) | 0.19753 (4) | 0.0606 (4) | |
O4B | 0.21161 (6) | 0.7410 (3) | 0.19886 (5) | 0.0946 (5) | |
N2A | 0.55969 (6) | 0.1485 (2) | 0.50650 (5) | 0.0698 (4) | |
O2' | 0.52718 (8) | 0.3814 (3) | 0.44659 (5) | 0.0978 (5) | |
O4A | 0.78574 (6) | −0.1384 (3) | 0.55011 (5) | 0.1011 (6) | |
N2B | 0.44240 (6) | 0.5183 (3) | 0.24363 (5) | 0.0721 (4) | |
O1' | 0.48855 (7) | 0.5514 (3) | 0.31647 (5) | 0.1049 (6) | |
O2A | 0.63071 (7) | 0.1226 (3) | 0.62598 (5) | 0.1110 (6) | |
N3A | 0.61124 (7) | 0.2312 (3) | 0.60258 (6) | 0.0859 (5) | |
C8B | 0.22773 (7) | 0.8238 (2) | 0.26590 (5) | 0.0603 (4) | |
O2B | 0.36980 (8) | 0.4818 (4) | 0.12448 (6) | 0.1210 (7) | |
N3B | 0.39162 (7) | 0.3882 (3) | 0.14929 (7) | 0.0919 (6) | |
C8A | 0.77042 (7) | −0.0609 (2) | 0.48271 (5) | 0.0616 (4) | |
C3A | 0.59504 (6) | 0.1642 (3) | 0.56527 (5) | 0.0629 (4) | |
O1A | 0.60434 (8) | 0.3983 (3) | 0.60894 (7) | 0.1274 (8) | |
C7B | 0.24133 (7) | 0.7746 (3) | 0.22482 (5) | 0.0637 (4) | |
C1B | 0.41703 (7) | 0.6707 (3) | 0.23323 (5) | 0.0633 (4) | |
C1A | 0.58274 (7) | −0.0115 (3) | 0.51389 (5) | 0.0647 (4) | |
C7A | 0.75635 (7) | −0.1104 (3) | 0.52361 (5) | 0.0660 (5) | |
C9A | 0.73439 (8) | −0.0105 (3) | 0.45482 (5) | 0.0644 (4) | |
C3B | 0.40651 (6) | 0.4703 (3) | 0.18565 (6) | 0.0661 (5) | |
C2A | 0.56744 (7) | 0.2580 (3) | 0.53836 (6) | 0.0678 (5) | |
C6' | 0.51323 (7) | 0.3226 (3) | 0.40973 (6) | 0.0687 (5) | |
C2' | 0.49229 (7) | 0.4103 (3) | 0.34347 (6) | 0.0721 (5) | |
C9B | 0.26411 (8) | 0.8558 (3) | 0.29468 (6) | 0.0689 (5) | |
C1' | 0.50863 (8) | 0.4587 (3) | 0.38117 (6) | 0.0741 (5) | |
C2B | 0.43581 (7) | 0.3946 (3) | 0.21394 (7) | 0.0730 (5) | |
C3' | 0.48105 (7) | 0.2277 (3) | 0.33438 (6) | 0.0734 (5) | |
C5' | 0.50283 (8) | 0.1381 (3) | 0.40091 (7) | 0.0735 (5) | |
C6B | 0.30779 (8) | 0.7433 (4) | 0.17856 (6) | 0.0731 (5) | |
C5B | 0.36357 (8) | 0.7879 (3) | 0.17681 (7) | 0.0741 (5) | |
C5A | 0.63229 (9) | −0.1684 (3) | 0.56795 (7) | 0.0777 (6) | |
C13B | 0.17693 (8) | 0.8428 (4) | 0.27569 (7) | 0.0797 (6) | |
C13A | 0.82152 (8) | −0.0597 (3) | 0.47209 (8) | 0.0801 (6) | |
C10A | 0.74957 (10) | 0.0442 (3) | 0.41755 (6) | 0.0790 (6) | |
C4' | 0.48680 (8) | 0.0933 (3) | 0.36331 (7) | 0.0780 (5) | |
C10B | 0.24940 (10) | 0.9079 (3) | 0.33226 (6) | 0.0824 (6) | |
C6A | 0.68875 (9) | −0.1410 (5) | 0.56883 (6) | 0.0838 (7) | |
C11B | 0.19922 (10) | 0.9302 (4) | 0.34139 (7) | 0.0853 (6) | |
O1B | 0.40194 (8) | 0.2250 (4) | 0.14505 (9) | 0.1469 (10) | |
C11A | 0.79998 (11) | 0.0491 (3) | 0.40780 (8) | 0.0891 (7) | |
C12A | 0.83596 (10) | −0.0054 (4) | 0.43460 (8) | 0.0919 (7) | |
C4B | 0.41432 (9) | 0.8429 (4) | 0.25758 (8) | 0.0914 (7) | |
H4BA | 0.436862 | 0.935305 | 0.246868 | 0.137* | |
H4BB | 0.424152 | 0.814614 | 0.284228 | 0.137* | |
H4BC | 0.380182 | 0.890062 | 0.257375 | 0.137* | |
C4A | 0.58372 (10) | −0.1713 (4) | 0.48615 (8) | 0.0960 (7) | |
H4AA | 0.617788 | −0.218047 | 0.484027 | 0.144* | |
H4AB | 0.572169 | −0.131042 | 0.460625 | 0.144* | |
H4AC | 0.561838 | −0.268338 | 0.495797 | 0.144* | |
C12B | 0.16312 (10) | 0.8963 (4) | 0.31324 (8) | 0.0908 (7) | |
H3' | 0.4671 (5) | 0.1999 (19) | 0.3050 (4) | 0.036 (3)* | |
H5' | 0.5072 (7) | 0.034 (3) | 0.4230 (5) | 0.058 (5)* | |
H6BA | 0.2885 (8) | 0.827 (3) | 0.1608 (7) | 0.077 (6)* | |
H2A | 0.5542 (9) | 0.370 (4) | 0.5409 (7) | 0.081 (7)* | |
H9A | 0.6979 (8) | −0.011 (3) | 0.4627 (6) | 0.075 (6)* | |
H1'A | 0.5167 (8) | 0.593 (3) | 0.3891 (7) | 0.081 (6)* | |
H13A | 0.8432 (9) | −0.106 (3) | 0.4913 (7) | 0.082 (7)* | |
H4' | 0.4801 (9) | −0.041 (4) | 0.3582 (7) | 0.090 (7)* | |
H5AA | 0.6207 (10) | −0.178 (4) | 0.5943 (9) | 0.100 (8)* | |
H2B | 0.4502 (9) | 0.278 (4) | 0.2145 (7) | 0.093 (7)* | |
H9B | 0.3015 (9) | 0.846 (3) | 0.2874 (7) | 0.090 (7)* | |
H6BB | 0.2999 (9) | 0.602 (4) | 0.1714 (7) | 0.092 (7)* | |
H6AA | 0.7045 (10) | −0.250 (4) | 0.5801 (8) | 0.103 (8)* | |
H5BA | 0.3718 (9) | 0.909 (3) | 0.1898 (7) | 0.084 (7)* | |
H11B | 0.1864 (9) | 0.985 (4) | 0.3692 (8) | 0.098 (7)* | |
H6AB | 0.6966 (11) | −0.033 (4) | 0.5822 (9) | 0.103 (9)* | |
H13B | 0.1530 (10) | 0.809 (4) | 0.2561 (8) | 0.105 (8)* | |
H5BB | 0.3746 (9) | 0.788 (3) | 0.1508 (8) | 0.093 (7)* | |
H5AB | 0.6241 (9) | −0.280 (4) | 0.5517 (7) | 0.086 (7)* | |
H11A | 0.8124 (10) | 0.095 (4) | 0.3826 (9) | 0.110 (9)* | |
H10A | 0.7236 (10) | 0.082 (4) | 0.3987 (8) | 0.103 (8)* | |
H10B | 0.2797 (12) | 0.934 (4) | 0.3530 (9) | 0.127 (10)* | |
H12B | 0.1301 (11) | 0.918 (4) | 0.3203 (8) | 0.109 (9)* | |
H12A | 0.8730 (12) | −0.002 (4) | 0.4288 (9) | 0.124 (10)* | |
H1' | 0.4698 (13) | 0.507 (5) | 0.2907 (11) | 0.145 (12)* | |
H2' | 0.5357 (15) | 0.266 (6) | 0.4639 (12) | 0.174 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3B | 0.0638 (7) | 0.0860 (9) | 0.0530 (6) | 0.0111 (6) | −0.0044 (5) | 0.0048 (6) |
O3A | 0.0637 (7) | 0.0888 (9) | 0.0549 (7) | 0.0131 (6) | −0.0043 (5) | 0.0036 (6) |
N1A | 0.0560 (7) | 0.0656 (8) | 0.0567 (8) | 0.0012 (6) | 0.0005 (6) | 0.0059 (7) |
N1B | 0.0565 (8) | 0.0702 (9) | 0.0550 (8) | −0.0013 (7) | 0.0003 (6) | 0.0026 (7) |
O4B | 0.0744 (9) | 0.1351 (14) | 0.0744 (9) | 0.0050 (9) | −0.0176 (7) | −0.0187 (9) |
N2A | 0.0701 (9) | 0.0748 (10) | 0.0646 (9) | 0.0050 (8) | −0.0072 (7) | 0.0050 (8) |
O2' | 0.1317 (14) | 0.0893 (11) | 0.0724 (9) | 0.0065 (10) | −0.0237 (9) | 0.0092 (8) |
O4A | 0.0755 (9) | 0.1502 (16) | 0.0777 (10) | 0.0214 (10) | −0.0196 (8) | 0.0123 (10) |
N2B | 0.0614 (8) | 0.0855 (11) | 0.0694 (9) | −0.0011 (8) | −0.0056 (7) | 0.0111 (8) |
O1' | 0.1253 (14) | 0.1048 (12) | 0.0845 (10) | −0.0311 (10) | −0.0359 (10) | 0.0347 (9) |
O2A | 0.0989 (12) | 0.1692 (19) | 0.0649 (9) | 0.0149 (12) | −0.0146 (8) | −0.0071 (11) |
N3A | 0.0617 (9) | 0.1170 (16) | 0.0789 (11) | 0.0060 (10) | −0.0095 (8) | −0.0261 (12) |
C8B | 0.0630 (9) | 0.0559 (9) | 0.0620 (9) | 0.0073 (7) | −0.0047 (7) | 0.0082 (8) |
O2B | 0.1083 (13) | 0.177 (2) | 0.0778 (10) | 0.0200 (14) | −0.0198 (10) | −0.0295 (12) |
N3B | 0.0644 (10) | 0.1138 (16) | 0.0974 (14) | 0.0070 (10) | −0.0029 (10) | −0.0408 (13) |
C8A | 0.0653 (10) | 0.0546 (9) | 0.0650 (10) | 0.0009 (7) | −0.0032 (8) | −0.0134 (8) |
C3A | 0.0531 (9) | 0.0731 (11) | 0.0626 (10) | −0.0047 (8) | 0.0008 (7) | −0.0051 (8) |
O1A | 0.1041 (13) | 0.1358 (17) | 0.1422 (18) | 0.0224 (12) | −0.0328 (12) | −0.0735 (15) |
C7B | 0.0642 (10) | 0.0633 (10) | 0.0637 (10) | 0.0086 (8) | −0.0112 (8) | 0.0031 (8) |
C1B | 0.0574 (9) | 0.0748 (11) | 0.0578 (9) | −0.0063 (8) | 0.0001 (7) | 0.0008 (8) |
C1A | 0.0600 (9) | 0.0712 (11) | 0.0631 (10) | 0.0022 (8) | −0.0023 (8) | −0.0012 (9) |
C7A | 0.0638 (10) | 0.0679 (11) | 0.0663 (10) | 0.0121 (8) | −0.0102 (8) | −0.0054 (9) |
C9A | 0.0735 (11) | 0.0595 (10) | 0.0603 (10) | 0.0014 (9) | −0.0032 (8) | −0.0057 (8) |
C3B | 0.0542 (9) | 0.0754 (12) | 0.0686 (11) | −0.0017 (8) | 0.0020 (8) | −0.0090 (9) |
C2A | 0.0649 (10) | 0.0597 (11) | 0.0789 (12) | 0.0006 (9) | −0.0028 (9) | 0.0007 (9) |
C6' | 0.0618 (10) | 0.0817 (13) | 0.0626 (10) | 0.0057 (9) | −0.0018 (8) | 0.0095 (9) |
C2' | 0.0595 (10) | 0.0903 (14) | 0.0665 (11) | −0.0062 (9) | −0.0054 (8) | 0.0188 (10) |
C9B | 0.0677 (11) | 0.0771 (12) | 0.0620 (10) | 0.0084 (9) | −0.0060 (8) | 0.0044 (9) |
C1' | 0.0758 (12) | 0.0728 (12) | 0.0737 (12) | −0.0028 (10) | −0.0119 (9) | 0.0096 (10) |
C2B | 0.0590 (10) | 0.0697 (12) | 0.0901 (14) | 0.0022 (9) | 0.0012 (9) | 0.0022 (11) |
C3' | 0.0629 (10) | 0.0871 (14) | 0.0702 (12) | −0.0060 (10) | 0.0006 (9) | 0.0015 (10) |
C5' | 0.0661 (11) | 0.0772 (13) | 0.0771 (12) | 0.0032 (9) | 0.0049 (9) | 0.0168 (10) |
C6B | 0.0735 (11) | 0.0950 (15) | 0.0507 (9) | 0.0169 (11) | −0.0042 (8) | 0.0097 (10) |
C5B | 0.0786 (12) | 0.0832 (14) | 0.0604 (11) | 0.0058 (10) | 0.0039 (9) | 0.0183 (10) |
C5A | 0.0805 (13) | 0.0806 (14) | 0.0720 (13) | 0.0147 (11) | 0.0060 (10) | 0.0226 (11) |
C13B | 0.0654 (11) | 0.0961 (15) | 0.0777 (13) | 0.0082 (11) | −0.0049 (10) | 0.0039 (11) |
C13A | 0.0679 (11) | 0.0853 (14) | 0.0870 (15) | −0.0032 (10) | −0.0037 (11) | −0.0200 (12) |
C10A | 0.1019 (15) | 0.0701 (12) | 0.0649 (11) | −0.0068 (11) | −0.0003 (12) | −0.0053 (9) |
C4' | 0.0696 (12) | 0.0771 (13) | 0.0872 (14) | −0.0044 (10) | 0.0064 (10) | 0.0008 (11) |
C10B | 0.0908 (14) | 0.0944 (15) | 0.0621 (11) | 0.0141 (12) | −0.0076 (11) | 0.0014 (10) |
C6A | 0.0753 (13) | 0.118 (2) | 0.0580 (11) | 0.0275 (13) | 0.0007 (9) | 0.0181 (13) |
C11B | 0.0988 (16) | 0.0913 (15) | 0.0657 (12) | 0.0218 (12) | 0.0088 (11) | 0.0113 (11) |
O1B | 0.1119 (15) | 0.1435 (19) | 0.185 (2) | 0.0282 (14) | −0.0336 (15) | −0.0900 (18) |
C11A | 0.1141 (19) | 0.0790 (14) | 0.0743 (14) | −0.0256 (13) | 0.0189 (14) | −0.0207 (11) |
C12A | 0.0846 (15) | 0.0949 (16) | 0.0961 (17) | −0.0210 (13) | 0.0233 (14) | −0.0306 (14) |
C4B | 0.0849 (14) | 0.0990 (16) | 0.0902 (15) | −0.0038 (12) | −0.0086 (12) | −0.0245 (13) |
C4A | 0.0959 (16) | 0.0983 (17) | 0.0939 (16) | 0.0162 (13) | −0.0162 (13) | −0.0305 (14) |
C12B | 0.0744 (13) | 0.1126 (19) | 0.0853 (15) | 0.0143 (13) | 0.0163 (12) | 0.0081 (13) |
Geometric parameters (Å, º) top
O3B—C7B | 1.344 (2) | N3B—C3B | 1.419 (3) |
O3B—C6B | 1.444 (2) | N3B—O1B | 1.208 (3) |
O3A—C7A | 1.345 (2) | C8A—C7A | 1.476 (3) |
O3A—C6A | 1.436 (2) | C8A—C9A | 1.386 (3) |
N1A—C3A | 1.381 (2) | C8A—C13A | 1.392 (3) |
N1A—C1A | 1.356 (2) | C3A—C2A | 1.344 (3) |
N1A—C5A | 1.468 (2) | C1B—C4B | 1.485 (3) |
N1B—C1B | 1.356 (2) | C1A—C4A | 1.480 (3) |
N1B—C3B | 1.379 (3) | C9A—C10A | 1.380 (3) |
N1B—C5B | 1.462 (3) | C3B—C2B | 1.344 (3) |
O4B—C7B | 1.201 (2) | C6'—C1' | 1.378 (3) |
N2A—C1A | 1.321 (3) | C6'—C5' | 1.382 (3) |
N2A—C2A | 1.348 (3) | C2'—C1' | 1.390 (3) |
O2'—C6' | 1.367 (3) | C2'—C3' | 1.376 (3) |
O4A—C7A | 1.201 (2) | C9B—C10B | 1.381 (3) |
N2B—C1B | 1.327 (3) | C3'—C4' | 1.381 (3) |
N2B—C2B | 1.350 (3) | C5'—C4' | 1.378 (3) |
O1'—C2' | 1.366 (3) | C6B—C5B | 1.504 (3) |
O2A—N3A | 1.223 (3) | C5A—C6A | 1.500 (3) |
N3A—C3A | 1.417 (3) | C13B—C12B | 1.376 (3) |
N3A—O1A | 1.229 (3) | C13A—C12A | 1.380 (4) |
C8B—C7B | 1.478 (3) | C10A—C11A | 1.368 (4) |
C8B—C9B | 1.385 (3) | C10B—C11B | 1.366 (3) |
C8B—C13B | 1.384 (3) | C11B—C12B | 1.367 (4) |
O2B—N3B | 1.218 (3) | C11A—C12A | 1.368 (4) |
| | | |
C7B—O3B—C6B | 115.49 (14) | N2A—C1A—C4A | 123.95 (18) |
C7A—O3A—C6A | 115.89 (15) | O3A—C7A—C8A | 112.42 (15) |
C3A—N1A—C5A | 129.51 (17) | O4A—C7A—O3A | 122.22 (19) |
C1A—N1A—C3A | 104.96 (15) | O4A—C7A—C8A | 125.35 (19) |
C1A—N1A—C5A | 125.52 (18) | C10A—C9A—C8A | 119.9 (2) |
C1B—N1B—C3B | 105.33 (15) | N1B—C3B—N3B | 125.01 (19) |
C1B—N1B—C5B | 126.37 (17) | C2B—C3B—N1B | 107.44 (18) |
C3B—N1B—C5B | 128.30 (17) | C2B—C3B—N3B | 127.5 (2) |
C1A—N2A—C2A | 106.47 (16) | C3A—C2A—N2A | 109.46 (18) |
C1B—N2B—C2B | 106.10 (16) | O2'—C6'—C1' | 116.5 (2) |
O2A—N3A—C3A | 119.2 (2) | O2'—C6'—C5' | 123.01 (18) |
O2A—N3A—O1A | 124.6 (2) | C1'—C6'—C5' | 120.5 (2) |
O1A—N3A—C3A | 116.2 (2) | O1'—C2'—C1' | 116.9 (2) |
C9B—C8B—C7B | 122.23 (17) | O1'—C2'—C3' | 122.55 (19) |
C13B—C8B—C7B | 118.84 (17) | C3'—C2'—C1' | 120.55 (19) |
C13B—C8B—C9B | 118.91 (19) | C10B—C9B—C8B | 119.90 (19) |
O2B—N3B—C3B | 120.0 (2) | C6'—C1'—C2' | 119.7 (2) |
O1B—N3B—O2B | 123.8 (2) | C3B—C2B—N2B | 109.83 (19) |
O1B—N3B—C3B | 116.2 (2) | C2'—C3'—C4' | 118.7 (2) |
C9A—C8A—C7A | 121.98 (17) | C4'—C5'—C6' | 118.9 (2) |
C9A—C8A—C13A | 118.92 (19) | O3B—C6B—C5B | 106.70 (17) |
C13A—C8A—C7A | 119.07 (18) | N1B—C5B—C6B | 112.24 (17) |
N1A—C3A—N3A | 125.69 (18) | N1A—C5A—C6A | 113.3 (2) |
C2A—C3A—N1A | 107.63 (17) | C12B—C13B—C8B | 120.2 (2) |
C2A—C3A—N3A | 126.7 (2) | C12A—C13A—C8A | 120.3 (2) |
O3B—C7B—C8B | 112.35 (15) | C11A—C10A—C9A | 120.6 (2) |
O4B—C7B—O3B | 122.31 (18) | C5'—C4'—C3' | 121.7 (2) |
O4B—C7B—C8B | 125.32 (18) | C11B—C10B—C9B | 120.7 (2) |
N1B—C1B—C4B | 124.64 (18) | O3A—C6A—C5A | 107.72 (18) |
N2B—C1B—N1B | 111.30 (17) | C10B—C11B—C12B | 119.6 (2) |
N2B—C1B—C4B | 124.06 (18) | C10A—C11A—C12A | 120.3 (2) |
N1A—C1A—C4A | 124.57 (18) | C11A—C12A—C13A | 119.9 (2) |
N2A—C1A—N1A | 111.47 (17) | C11B—C12B—C13B | 120.6 (2) |
2-(2-Methyl-5-nitro-1
H-imidazol-1-yl)ethyl benzoate–fumaric acid (2/1) (bzmdfma)
top
Crystal data top
C13H13N3O4·0.5C4H4O4 | F(000) = 696 |
Mr = 333.30 | Dx = 1.369 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0358 (5) Å | Cell parameters from 9988 reflections |
b = 26.6419 (14) Å | θ = 2.3–28.9° |
c = 6.8796 (3) Å | µ = 0.11 mm−1 |
β = 102.419 (2)° | T = 300 K |
V = 1617.38 (14) Å3 | Prism, clear light colourless |
Z = 4 | 0.63 × 0.17 × 0.17 mm |
Data collection top
Bruker APEXII CCD diffractometer | 2625 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.066 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 27.5°, θmin = 2.8° |
Tmin = 0.620, Tmax = 0.746 | h = −11→11 |
46849 measured reflections | k = −34→34 |
3705 independent reflections | l = −8→8 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.051 | w = 1/[σ2(Fo2) + (0.0568P)2 + 0.5999P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.151 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.39 e Å−3 |
3705 reflections | Δρmin = −0.33 e Å−3 |
267 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.018 (3) |
Primary atom site location: dual | |
Special details top
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 | x | y | z | Uiso*/Ueq | |
O1 | 0.8887 (3) | 0.59652 (9) | 0.3299 (4) | 0.1261 (9) | |
O2 | 0.9417 (2) | 0.62892 (9) | 0.6242 (4) | 0.1134 (8) | |
O3 | 0.55707 (16) | 0.70919 (5) | 0.7641 (2) | 0.0614 (4) | |
O4 | 0.6408 (2) | 0.78808 (6) | 0.7663 (3) | 0.0818 (5) | |
N1 | 0.64502 (18) | 0.60717 (6) | 0.6676 (2) | 0.0535 (4) | |
N2 | 0.4807 (2) | 0.56134 (6) | 0.4570 (3) | 0.0640 (5) | |
N3 | 0.8562 (3) | 0.60697 (8) | 0.4893 (4) | 0.0820 (6) | |
C1 | 0.5053 (2) | 0.58656 (7) | 0.6269 (3) | 0.0574 (5) | |
C2 | 0.6064 (3) | 0.56549 (8) | 0.3829 (4) | 0.0649 (6) | |
H2 | 0.620 (3) | 0.5508 (9) | 0.262 (4) | 0.078 (7)* | |
C3 | 0.7094 (2) | 0.59375 (7) | 0.5099 (3) | 0.0575 (5) | |
C4 | 0.3945 (3) | 0.59055 (10) | 0.7556 (4) | 0.0838 (7) | |
H4A | 0.417788 | 0.566096 | 0.860183 | 0.126* | |
H4B | 0.294408 | 0.584567 | 0.677807 | 0.126* | |
H4C | 0.399275 | 0.623576 | 0.812368 | 0.126* | |
C5 | 0.7116 (3) | 0.63718 (9) | 0.8440 (3) | 0.0633 (5) | |
H5A | 0.650 (3) | 0.6299 (9) | 0.940 (4) | 0.069 (6)* | |
H5B | 0.815 (3) | 0.6255 (9) | 0.896 (3) | 0.073 (7)* | |
C6 | 0.7118 (2) | 0.69224 (9) | 0.7997 (4) | 0.0651 (6) | |
H6A | 0.766 (3) | 0.7091 (9) | 0.907 (4) | 0.073 (7)* | |
H6B | 0.751 (3) | 0.6996 (9) | 0.672 (4) | 0.075 (7)* | |
C7 | 0.5365 (2) | 0.75911 (8) | 0.7537 (3) | 0.0564 (5) | |
C8 | 0.3754 (2) | 0.77333 (7) | 0.7313 (3) | 0.0540 (5) | |
C9 | 0.2606 (3) | 0.73811 (9) | 0.7113 (3) | 0.0605 (5) | |
H9 | 0.287 (3) | 0.7036 (10) | 0.710 (4) | 0.082 (8)* | |
C10 | 0.1132 (3) | 0.75312 (10) | 0.6989 (4) | 0.0725 (6) | |
H10 | 0.031 (3) | 0.7287 (10) | 0.685 (4) | 0.092 (8)* | |
C11 | 0.0794 (3) | 0.80314 (11) | 0.7083 (4) | 0.0807 (7) | |
H11 | −0.026 (3) | 0.8135 (10) | 0.702 (4) | 0.087 (8)* | |
C12 | 0.1916 (4) | 0.83847 (11) | 0.7265 (4) | 0.0856 (8) | |
H12 | 0.163 (3) | 0.8738 (12) | 0.734 (4) | 0.101 (9)* | |
C13 | 0.3391 (3) | 0.82380 (9) | 0.7366 (4) | 0.0717 (6) | |
H13 | 0.421 (3) | 0.8472 (11) | 0.743 (4) | 0.094 (9)* | |
O1' | 0.21422 (19) | 0.52552 (7) | 0.2699 (3) | 0.0859 (6) | |
H1' | 0.317 (4) | 0.5368 (13) | 0.342 (5) | 0.121 (11)* | |
O2' | 0.32943 (17) | 0.49184 (7) | 0.0484 (3) | 0.0836 (5) | |
C1' | 0.2163 (2) | 0.50351 (7) | 0.1006 (3) | 0.0578 (5) | |
C2' | 0.0625 (2) | 0.49372 (8) | −0.0245 (4) | 0.0629 (5) | |
H2' | 0.055 (3) | 0.4785 (11) | −0.152 (5) | 0.102 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.1359 (19) | 0.1154 (17) | 0.157 (2) | −0.0397 (14) | 0.0970 (17) | −0.0559 (15) |
O2 | 0.0673 (12) | 0.1338 (18) | 0.1422 (19) | −0.0313 (12) | 0.0291 (12) | −0.0469 (15) |
O3 | 0.0542 (8) | 0.0556 (8) | 0.0704 (9) | −0.0035 (6) | 0.0045 (6) | −0.0106 (6) |
O4 | 0.0761 (11) | 0.0657 (10) | 0.1059 (13) | −0.0188 (8) | 0.0246 (9) | −0.0086 (9) |
N1 | 0.0530 (9) | 0.0500 (9) | 0.0554 (9) | −0.0022 (7) | 0.0070 (7) | −0.0012 (7) |
N2 | 0.0587 (11) | 0.0481 (9) | 0.0776 (12) | −0.0030 (7) | −0.0020 (9) | 0.0004 (8) |
N3 | 0.0767 (14) | 0.0666 (12) | 0.1122 (17) | −0.0152 (10) | 0.0416 (13) | −0.0255 (11) |
C1 | 0.0508 (11) | 0.0476 (10) | 0.0712 (13) | −0.0010 (8) | 0.0070 (9) | 0.0084 (9) |
C2 | 0.0772 (15) | 0.0472 (11) | 0.0676 (13) | −0.0024 (10) | 0.0094 (11) | −0.0061 (9) |
C3 | 0.0590 (12) | 0.0471 (10) | 0.0667 (12) | −0.0040 (8) | 0.0147 (9) | −0.0041 (9) |
C4 | 0.0685 (15) | 0.0803 (16) | 0.109 (2) | −0.0047 (12) | 0.0329 (14) | 0.0080 (14) |
C5 | 0.0616 (13) | 0.0701 (14) | 0.0529 (11) | 0.0021 (10) | 0.0008 (10) | −0.0056 (10) |
C6 | 0.0532 (12) | 0.0675 (13) | 0.0686 (14) | −0.0051 (10) | 0.0000 (10) | −0.0185 (11) |
C7 | 0.0679 (13) | 0.0558 (11) | 0.0450 (10) | −0.0084 (9) | 0.0112 (9) | −0.0079 (8) |
C8 | 0.0648 (12) | 0.0562 (11) | 0.0385 (9) | −0.0020 (9) | 0.0058 (8) | −0.0047 (8) |
C9 | 0.0643 (13) | 0.0598 (13) | 0.0535 (11) | −0.0015 (10) | 0.0042 (9) | −0.0051 (9) |
C10 | 0.0626 (14) | 0.0813 (16) | 0.0685 (14) | −0.0029 (12) | 0.0027 (11) | −0.0098 (12) |
C11 | 0.0717 (17) | 0.0923 (19) | 0.0706 (15) | 0.0176 (15) | −0.0017 (12) | −0.0112 (13) |
C12 | 0.092 (2) | 0.0672 (16) | 0.0907 (18) | 0.0186 (14) | 0.0038 (14) | −0.0066 (13) |
C13 | 0.0855 (17) | 0.0556 (13) | 0.0709 (14) | −0.0021 (12) | 0.0099 (12) | −0.0047 (10) |
O1' | 0.0529 (10) | 0.0983 (13) | 0.1000 (13) | −0.0022 (8) | 0.0019 (8) | −0.0331 (10) |
O2' | 0.0461 (9) | 0.1114 (14) | 0.0934 (12) | 0.0015 (8) | 0.0152 (8) | −0.0062 (10) |
C1' | 0.0497 (11) | 0.0496 (11) | 0.0720 (13) | −0.0020 (8) | 0.0085 (9) | −0.0015 (9) |
C2' | 0.0479 (11) | 0.0601 (12) | 0.0785 (14) | −0.0023 (9) | 0.0083 (10) | −0.0123 (10) |
Geometric parameters (Å, º) top
O1—N3 | 1.227 (3) | C6—H6A | 0.91 (3) |
O2—N3 | 1.221 (3) | C6—H6B | 1.03 (3) |
O3—C6 | 1.439 (3) | C7—C8 | 1.480 (3) |
O3—C7 | 1.343 (2) | C8—C9 | 1.383 (3) |
O4—C7 | 1.206 (2) | C8—C13 | 1.386 (3) |
N1—C1 | 1.350 (3) | C9—H9 | 0.95 (3) |
N1—C3 | 1.384 (3) | C9—C10 | 1.375 (3) |
N1—C5 | 1.469 (3) | C10—H10 | 0.98 (3) |
N2—C1 | 1.325 (3) | C10—C11 | 1.372 (4) |
N2—C2 | 1.346 (3) | C11—H11 | 0.98 (3) |
N3—C3 | 1.408 (3) | C11—C12 | 1.369 (4) |
C1—C4 | 1.475 (3) | C12—H12 | 0.98 (3) |
C2—H2 | 0.95 (2) | C12—C13 | 1.376 (4) |
C2—C3 | 1.359 (3) | C13—H13 | 0.96 (3) |
C4—H4A | 0.9600 | O1'—H1' | 1.00 (4) |
C4—H4B | 0.9600 | O1'—C1' | 1.308 (3) |
C4—H4C | 0.9600 | O2'—C1' | 1.195 (2) |
C5—H5A | 0.97 (2) | C1'—C2' | 1.492 (3) |
C5—H5B | 0.98 (3) | C2'—C2'i | 1.290 (4) |
C5—C6 | 1.498 (3) | C2'—H2' | 0.96 (3) |
| | | |
C7—O3—C6 | 115.97 (16) | C5—C6—H6A | 110.0 (15) |
C1—N1—C3 | 105.33 (17) | C5—C6—H6B | 112.0 (13) |
C1—N1—C5 | 126.25 (19) | H6A—C6—H6B | 112 (2) |
C3—N1—C5 | 128.42 (18) | O3—C7—C8 | 112.38 (17) |
C1—N2—C2 | 107.32 (18) | O4—C7—O3 | 122.2 (2) |
O1—N3—C3 | 116.4 (2) | O4—C7—C8 | 125.4 (2) |
O2—N3—O1 | 123.6 (2) | C9—C8—C7 | 122.44 (19) |
O2—N3—C3 | 119.9 (2) | C9—C8—C13 | 118.9 (2) |
N1—C1—C4 | 124.8 (2) | C13—C8—C7 | 118.6 (2) |
N2—C1—N1 | 111.17 (19) | C8—C9—H9 | 118.1 (16) |
N2—C1—C4 | 124.0 (2) | C10—C9—C8 | 120.3 (2) |
N2—C2—H2 | 125.0 (15) | C10—C9—H9 | 121.5 (16) |
N2—C2—C3 | 108.6 (2) | C9—C10—H10 | 121.3 (16) |
C3—C2—H2 | 126.4 (15) | C11—C10—C9 | 120.1 (3) |
N1—C3—N3 | 125.29 (19) | C11—C10—H10 | 118.5 (16) |
C2—C3—N1 | 107.59 (19) | C10—C11—H11 | 119.7 (16) |
C2—C3—N3 | 127.1 (2) | C12—C11—C10 | 120.3 (3) |
C1—C4—H4A | 109.5 | C12—C11—H11 | 120.0 (16) |
C1—C4—H4B | 109.5 | C11—C12—H12 | 117.6 (17) |
C1—C4—H4C | 109.5 | C11—C12—C13 | 120.0 (3) |
H4A—C4—H4B | 109.5 | C13—C12—H12 | 122.4 (17) |
H4A—C4—H4C | 109.5 | C8—C13—H13 | 116.6 (17) |
H4B—C4—H4C | 109.5 | C12—C13—C8 | 120.4 (2) |
N1—C5—H5A | 105.1 (14) | C12—C13—H13 | 123.0 (17) |
N1—C5—H5B | 108.7 (14) | C1'—O1'—H1' | 112.7 (19) |
N1—C5—C6 | 112.52 (18) | O1'—C1'—C2' | 113.71 (19) |
H5A—C5—H5B | 109.2 (19) | O2'—C1'—O1' | 124.1 (2) |
C6—C5—H5A | 111.0 (14) | O2'—C1'—C2' | 122.2 (2) |
C6—C5—H5B | 110.2 (14) | C1'—C2'—H2' | 118.3 (17) |
O3—C6—C5 | 107.36 (19) | C2'i—C2'—C1' | 124.3 (3) |
O3—C6—H6A | 108.5 (15) | C2'i—C2'—H2' | 117.3 (17) |
O3—C6—H6B | 107.2 (14) | | |
Symmetry code: (i) −x, −y+1, −z. |
2-(2-Methyl-5-nitro-1
H-imidazol-1-yl)ethyl benzoate–malonic acid (2/1) (bzmdmln)
top
Crystal data top
2C13H13N3O4·C3H2O4 | Dx = 1.367 Mg m−3 |
Mr = 652.57 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, Pbcn | Cell parameters from 9937 reflections |
a = 26.1542 (4) Å | θ = 3.1–72.5° |
b = 7.2708 (1) Å | µ = 0.92 mm−1 |
c = 16.6719 (3) Å | T = 300 K |
V = 3170.36 (9) Å3 | Prism, clear light colourless |
Z = 4 | 0.46 × 0.29 × 0.13 mm |
F(000) = 1360 | |
Data collection top
Bruker APEXII CCD diffractometer | 2423 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.038 |
Absorption correction: numerical (SADABS; Bruker, 2016) | θmax = 68.2°, θmin = 5.6° |
Tmin = 0.736, Tmax = 0.907 | h = −31→31 |
54755 measured reflections | k = −8→8 |
2893 independent reflections | l = −20→20 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.078 | w = 1/[σ2(Fo2) + (0.1596P)2 + 0.3629P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.268 | (Δ/σ)max = 0.001 |
S = 1.13 | Δρmax = 0.33 e Å−3 |
2893 reflections | Δρmin = −0.27 e Å−3 |
244 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
36 restraints | Extinction coefficient: 0.0039 (11) |
Primary atom site location: dual | |
Special details top
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O3 | 0.29519 (7) | 0.6661 (3) | 0.53894 (10) | 0.1002 (6) | |
O4 | 0.21543 (9) | 0.6847 (4) | 0.58610 (14) | 0.1407 (10) | |
N1 | 0.39769 (8) | 0.5613 (3) | 0.58207 (13) | 0.0982 (6) | |
C7 | 0.24416 (10) | 0.6583 (4) | 0.53037 (16) | 0.0976 (7) | |
N2 | 0.44070 (10) | 0.3861 (5) | 0.49826 (17) | 0.1221 (9) | |
C13 | 0.26247 (11) | 0.5592 (3) | 0.39102 (16) | 0.0990 (7) | |
H13 | 0.297280 | 0.557512 | 0.402389 | 0.119* | |
N3 | 0.39562 (11) | 0.3512 (5) | 0.7007 (2) | 0.1341 (10) | |
C8 | 0.22811 (9) | 0.6113 (3) | 0.44877 (16) | 0.0912 (7) | |
O1 | 0.36955 (13) | 0.4498 (6) | 0.73879 (15) | 0.1791 (15) | |
C6 | 0.31291 (13) | 0.6898 (5) | 0.61932 (18) | 0.1201 (10) | |
H6A | 0.304906 | 0.581714 | 0.651065 | 0.144* | |
H6B | 0.296435 | 0.795389 | 0.643718 | 0.144* | |
C5 | 0.36982 (14) | 0.7184 (5) | 0.6162 (2) | 0.1214 (10) | |
H5A | 0.377022 | 0.826914 | 0.584294 | 0.146* | |
H5B | 0.382282 | 0.741023 | 0.670087 | 0.146* | |
C1 | 0.41726 (10) | 0.5501 (5) | 0.50779 (16) | 0.1076 (9) | |
C2 | 0.43619 (11) | 0.2967 (5) | 0.5682 (2) | 0.1165 (9) | |
H2 | 0.449468 | 0.180669 | 0.579041 | 0.140* | |
C12 | 0.24521 (15) | 0.5095 (5) | 0.31615 (19) | 0.1220 (10) | |
H12 | 0.268778 | 0.474998 | 0.277171 | 0.146* | |
C9 | 0.17676 (12) | 0.6158 (5) | 0.4293 (2) | 0.1239 (10) | |
H9 | 0.152766 | 0.653022 | 0.467173 | 0.149* | |
O2 | 0.41029 (16) | 0.2059 (6) | 0.7247 (3) | 0.2129 (19) | |
C3 | 0.40976 (10) | 0.3995 (4) | 0.61981 (18) | 0.1060 (8) | |
C10 | 0.16136 (17) | 0.5646 (7) | 0.3534 (3) | 0.1490 (15) | |
H10 | 0.126798 | 0.568399 | 0.340365 | 0.179* | |
C11 | 0.1952 (2) | 0.5094 (6) | 0.2979 (2) | 0.1391 (13) | |
H11 | 0.184141 | 0.471593 | 0.247515 | 0.167* | |
C4 | 0.41453 (17) | 0.6957 (7) | 0.4471 (3) | 0.1555 (16) | |
H4A | 0.380368 | 0.743804 | 0.445026 | 0.233* | |
H4B | 0.423554 | 0.646143 | 0.395651 | 0.233* | |
H4C | 0.437869 | 0.792578 | 0.460914 | 0.233* | |
O1' | 0.4899 (3) | 0.1937 (13) | 0.3802 (4) | 0.138 (3) | 0.5 |
H1' | 0.462376 | 0.171352 | 0.401729 | 0.207* | 0.5 |
C1' | 0.4823 (3) | 0.2427 (12) | 0.3078 (5) | 0.106 (2) | 0.5 |
O2' | 0.4576 (4) | 0.3627 (13) | 0.2891 (5) | 0.213 (4) | 0.5 |
C2' | 0.500000 | 0.1017 (7) | 0.250000 | 0.1213 (13) | |
O2" | 0.5116 (4) | 0.1127 (9) | 0.3942 (4) | 0.152 (2) | 0.5 |
C1" | 0.4925 (3) | 0.1738 (11) | 0.3373 (6) | 0.105 (2) | 0.5 |
O1" | 0.4611 (3) | 0.3098 (12) | 0.3421 (5) | 0.185 (3) | 0.5 |
H1" | 0.450297 | 0.317907 | 0.388154 | 0.277* | 0.5 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0978 (12) | 0.1145 (12) | 0.0883 (11) | 0.0141 (8) | 0.0050 (8) | 0.0030 (8) |
O4 | 0.1174 (15) | 0.190 (2) | 0.1145 (16) | 0.0319 (14) | 0.0284 (12) | −0.0079 (15) |
N1 | 0.0877 (12) | 0.1129 (14) | 0.0940 (13) | −0.0032 (10) | −0.0056 (9) | −0.0007 (10) |
C7 | 0.0945 (15) | 0.0968 (14) | 0.1015 (16) | 0.0193 (11) | 0.0169 (12) | 0.0104 (12) |
N2 | 0.0934 (14) | 0.160 (2) | 0.1128 (17) | −0.0092 (14) | 0.0132 (12) | −0.0241 (16) |
C13 | 0.1102 (17) | 0.0899 (14) | 0.0968 (16) | −0.0003 (12) | 0.0094 (12) | 0.0096 (12) |
N3 | 0.1095 (18) | 0.169 (3) | 0.124 (2) | 0.0232 (17) | 0.0120 (15) | 0.0390 (19) |
C8 | 0.0917 (14) | 0.0806 (12) | 0.1014 (15) | 0.0051 (10) | 0.0060 (11) | 0.0209 (11) |
O1 | 0.159 (2) | 0.275 (4) | 0.1037 (16) | 0.063 (3) | 0.0161 (15) | 0.026 (2) |
C6 | 0.120 (2) | 0.150 (2) | 0.0906 (16) | 0.0267 (18) | −0.0044 (14) | −0.0155 (16) |
C5 | 0.130 (2) | 0.118 (2) | 0.116 (2) | 0.0064 (17) | −0.0114 (17) | −0.0212 (16) |
C1 | 0.0871 (14) | 0.141 (2) | 0.0945 (16) | −0.0176 (14) | −0.0003 (11) | 0.0035 (15) |
C2 | 0.0947 (17) | 0.124 (2) | 0.131 (2) | −0.0053 (14) | 0.0115 (16) | −0.0025 (17) |
C12 | 0.151 (3) | 0.1107 (19) | 0.1046 (19) | −0.0162 (19) | 0.0084 (19) | 0.0106 (16) |
C9 | 0.0969 (18) | 0.140 (2) | 0.135 (3) | 0.0034 (16) | 0.0031 (17) | 0.025 (2) |
O2 | 0.197 (3) | 0.230 (4) | 0.212 (4) | 0.064 (3) | 0.060 (3) | 0.109 (3) |
C3 | 0.0827 (14) | 0.1249 (19) | 0.1105 (18) | −0.0017 (13) | 0.0031 (12) | 0.0086 (15) |
C10 | 0.126 (3) | 0.165 (3) | 0.157 (4) | −0.015 (2) | −0.040 (3) | 0.038 (3) |
C11 | 0.171 (3) | 0.129 (2) | 0.117 (2) | −0.039 (3) | −0.026 (2) | 0.034 (2) |
C4 | 0.131 (3) | 0.207 (4) | 0.128 (3) | −0.021 (3) | 0.000 (2) | 0.048 (3) |
O1' | 0.141 (5) | 0.174 (6) | 0.099 (4) | 0.044 (4) | 0.001 (3) | 0.000 (4) |
C1' | 0.089 (4) | 0.126 (6) | 0.104 (4) | 0.017 (4) | 0.004 (3) | 0.013 (4) |
O2' | 0.302 (10) | 0.225 (7) | 0.112 (4) | 0.145 (7) | 0.025 (5) | 0.010 (5) |
C2' | 0.131 (3) | 0.133 (3) | 0.099 (3) | 0.000 | −0.001 (2) | 0.000 |
O2" | 0.210 (7) | 0.134 (4) | 0.111 (4) | 0.034 (4) | −0.017 (4) | −0.010 (3) |
C1" | 0.079 (4) | 0.099 (5) | 0.135 (8) | 0.003 (3) | 0.015 (5) | 0.010 (5) |
O1" | 0.203 (7) | 0.218 (7) | 0.134 (5) | 0.106 (6) | 0.029 (5) | 0.018 (5) |
Geometric parameters (Å, º) top
O3—C7 | 1.344 (3) | C8—C9 | 1.382 (4) |
O3—C6 | 1.428 (4) | C6—C5 | 1.504 (5) |
O4—C7 | 1.210 (3) | C1—C4 | 1.466 (5) |
N1—C5 | 1.469 (4) | C2—C3 | 1.333 (4) |
N1—C1 | 1.343 (4) | C12—C11 | 1.344 (5) |
N1—C3 | 1.371 (4) | C9—C10 | 1.380 (6) |
C7—C8 | 1.464 (4) | C10—C11 | 1.341 (6) |
N2—C1 | 1.350 (4) | O1'—C1' | 1.274 (9) |
N2—C2 | 1.340 (4) | C1'—O2' | 1.129 (9) |
C13—C8 | 1.370 (4) | C1'—C2' | 1.482 (9) |
C13—C12 | 1.376 (4) | C2'—C1" | 1.559 (10) |
N3—O1 | 1.176 (4) | C2'—C1"i | 1.559 (10) |
N3—O2 | 1.193 (4) | O2"—C1" | 1.161 (11) |
N3—C3 | 1.441 (4) | C1"—O1" | 1.288 (9) |
| | | |
C7—O3—C6 | 115.3 (2) | N2—C1—C4 | 125.4 (3) |
C1—N1—C5 | 126.4 (3) | C3—C2—N2 | 109.6 (3) |
C1—N1—C3 | 106.4 (2) | C11—C12—C13 | 121.7 (3) |
C3—N1—C5 | 127.1 (3) | C10—C9—C8 | 119.5 (3) |
O3—C7—C8 | 113.2 (2) | N1—C3—N3 | 125.4 (3) |
O4—C7—O3 | 121.9 (3) | C2—C3—N1 | 107.7 (3) |
O4—C7—C8 | 124.9 (3) | C2—C3—N3 | 126.9 (3) |
C2—N2—C1 | 106.6 (3) | C11—C10—C9 | 121.4 (4) |
C8—C13—C12 | 119.7 (3) | C10—C11—C12 | 119.1 (4) |
O1—N3—O2 | 122.9 (4) | O1'—C1'—C2' | 112.0 (7) |
O1—N3—C3 | 120.4 (3) | O2'—C1'—O1' | 124.5 (8) |
O2—N3—C3 | 116.6 (4) | O2'—C1'—C2' | 122.3 (7) |
C13—C8—C7 | 122.0 (2) | C1'i—C2'—C1' | 92.4 (7) |
C13—C8—C9 | 118.6 (3) | C1'i—C2'—C1"i | 28.4 (3) |
C9—C8—C7 | 119.4 (3) | C1'—C2'—C1"i | 114.4 (6) |
O3—C6—C5 | 107.8 (3) | C1"i—C2'—C1" | 140.7 (7) |
N1—C5—C6 | 113.4 (3) | O2"—C1"—C2' | 125.5 (7) |
N1—C1—N2 | 109.6 (3) | O2"—C1"—O1" | 121.1 (10) |
N1—C1—C4 | 125.0 (3) | O1"—C1"—C2' | 113.4 (8) |
Symmetry code: (i) −x+1, y, −z+1/2. |
1-[2-(Benzoyloxy)ethyl]-2-methyl-5-nitro-1
H-imidazol-3-ium
2,6-dihydroxybenzoate (bzmd26dba)
top
Crystal data top
C13H14N3O4+·C7H5O4− | F(000) = 896 |
Mr = 429.38 | Dx = 1.442 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2443 (4) Å | Cell parameters from 9886 reflections |
b = 15.9009 (7) Å | θ = 2.5–27.5° |
c = 15.4526 (8) Å | µ = 0.11 mm−1 |
β = 102.454 (2)° | T = 301 K |
V = 1978.04 (17) Å3 | Prism, clear light yellow |
Z = 4 | 0.83 × 0.67 × 0.27 mm |
Data collection top
Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer | 3408 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.076 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 27.5°, θmin = 2.8° |
Tmin = 0.490, Tmax = 0.746 | h = −10→10 |
27674 measured reflections | k = −20→20 |
4348 independent reflections | l = −20→19 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.069 | All H-atom parameters refined |
wR(F2) = 0.185 | w = 1/[σ2(Fo2) + (0.0913P)2 + 0.5735P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
4348 reflections | Δρmax = 0.37 e Å−3 |
356 parameters | Δρmin = −0.27 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Single-crystal X-ray diffraction data collection (ϕ scans
and ω scans with κ and θ offsets) were performed at room temperature on a
Bruker AXS D8 VENTURE equipped with a Kappa goniometer, PHOTON II CPAD
detector, a Mo Kα INCOATEC IµS 3.0 microfocus source (λ =
0.71073 Å). The crystal centring, unit-cell determination, refinement of the
unit-cell parameters and data collection was controlled through the program
APEX3 (Bruker, 2012). The frame integration was performed using
SAINT (Bruker, 2016) and the intensities were scaled and absorption
corrected using SADABS (Bruker, 2001). Using OLEX2 (Dolomanov
et al., 2009), the structure was solved by intrinsic phasing using
SHELXT (Sheldrick, 2015) and refined by full-matrix least-squares
calculation based on F2 for all reflection using SHELXL
(Sheldrick, 2007). All non-H atoms were refined anisotropically. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.30908 (16) | 0.45737 (9) | 0.10470 (8) | 0.0471 (3) | |
O1' | 0.69550 (19) | 0.38992 (10) | 0.49968 (10) | 0.0592 (4) | |
N1 | 0.25612 (18) | 0.49805 (10) | 0.28713 (10) | 0.0407 (4) | |
O2 | −0.08963 (19) | 0.47761 (14) | 0.24372 (12) | 0.0777 (6) | |
O4' | 1.0124 (2) | 0.38277 (12) | 0.56331 (14) | 0.0725 (5) | |
O2' | 0.5209 (2) | 0.32169 (12) | 0.56404 (14) | 0.0728 (5) | |
N2 | 0.4226 (2) | 0.44392 (10) | 0.40318 (11) | 0.0478 (4) | |
N3 | −0.0133 (2) | 0.44450 (12) | 0.31200 (12) | 0.0545 (5) | |
O1 | −0.0783 (2) | 0.40294 (14) | 0.36109 (14) | 0.0832 (6) | |
O4 | 0.1499 (2) | 0.39405 (13) | −0.01207 (12) | 0.0778 (6) | |
O3' | 0.6249 (3) | 0.22744 (13) | 0.69473 (15) | 0.0855 (6) | |
C1' | 0.8096 (3) | 0.30675 (11) | 0.62457 (12) | 0.0455 (4) | |
C1 | 0.4158 (2) | 0.48952 (12) | 0.33097 (13) | 0.0441 (4) | |
C7' | 0.6658 (3) | 0.33991 (13) | 0.55944 (13) | 0.0485 (5) | |
C8 | 0.4427 (2) | 0.37835 (12) | 0.01068 (13) | 0.0448 (4) | |
C6 | 0.1575 (2) | 0.48994 (15) | 0.12428 (14) | 0.0494 (5) | |
C3 | 0.1624 (2) | 0.45427 (12) | 0.33634 (12) | 0.0435 (4) | |
C2 | 0.2662 (3) | 0.42133 (13) | 0.40789 (13) | 0.0487 (5) | |
C5 | 0.2007 (3) | 0.54528 (13) | 0.20416 (14) | 0.0479 (5) | |
C2' | 0.9742 (3) | 0.32956 (13) | 0.62356 (14) | 0.0531 (5) | |
C7 | 0.2864 (2) | 0.40967 (13) | 0.03172 (13) | 0.0484 (5) | |
C13 | 0.4327 (3) | 0.33220 (15) | −0.06576 (17) | 0.0618 (6) | |
C9 | 0.5971 (3) | 0.39351 (15) | 0.06467 (16) | 0.0563 (5) | |
C3' | 1.1037 (4) | 0.29727 (17) | 0.6877 (2) | 0.0774 (8) | |
C4 | 0.5618 (3) | 0.5256 (2) | 0.3029 (2) | 0.0649 (6) | |
C10 | 0.7374 (3) | 0.36102 (18) | 0.04179 (19) | 0.0694 (7) | |
C12 | 0.5745 (4) | 0.30044 (16) | −0.08794 (19) | 0.0693 (7) | |
C6' | 0.7806 (4) | 0.25214 (13) | 0.69090 (15) | 0.0616 (6) | |
C11 | 0.7265 (3) | 0.31502 (16) | −0.03340 (19) | 0.0669 (6) | |
C4' | 1.0704 (5) | 0.24431 (17) | 0.7517 (2) | 0.0892 (11) | |
C5' | 0.9118 (5) | 0.22182 (16) | 0.75427 (19) | 0.0829 (9) | |
H5A | 0.292 (3) | 0.5844 (13) | 0.2002 (14) | 0.048 (5)* | |
H6A | 0.086 (3) | 0.4400 (15) | 0.1351 (16) | 0.058 (6)* | |
H2 | 0.238 (3) | 0.3877 (14) | 0.4495 (17) | 0.058 (7)* | |
H5B | 0.109 (3) | 0.5774 (15) | 0.2123 (15) | 0.057 (6)* | |
H6B | 0.099 (3) | 0.5229 (15) | 0.0737 (18) | 0.065 (7)* | |
H12 | 0.564 (4) | 0.2705 (17) | −0.142 (2) | 0.081 (8)* | |
H9 | 0.599 (3) | 0.4257 (16) | 0.1141 (18) | 0.063 (7)* | |
H3' | 1.210 (4) | 0.3103 (19) | 0.676 (2) | 0.088 (9)* | |
H11 | 0.823 (4) | 0.2909 (16) | −0.0509 (18) | 0.074 (8)* | |
H4'A | 1.152 (4) | 0.2196 (19) | 0.798 (2) | 0.095 (10)* | |
H4' | 0.898 (5) | 0.399 (2) | 0.523 (2) | 0.116 (12)* | |
H10 | 0.843 (4) | 0.370 (2) | 0.082 (2) | 0.100 (10)* | |
H13 | 0.330 (4) | 0.3231 (18) | −0.103 (2) | 0.086 (9)* | |
H5' | 0.879 (4) | 0.187 (2) | 0.801 (2) | 0.102 (10)* | |
H2' | 0.562 (5) | 0.270 (3) | 0.638 (3) | 0.133 (14)* | |
H1' | 0.548 (6) | 0.415 (2) | 0.454 (3) | 0.132 (13)* | |
H4A | 0.575 (5) | 0.504 (2) | 0.250 (3) | 0.117 (13)* | |
H4B | 0.554 (6) | 0.585 (3) | 0.303 (3) | 0.133 (15)* | |
H4C | 0.653 (6) | 0.515 (3) | 0.347 (3) | 0.138 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0316 (7) | 0.0630 (8) | 0.0445 (7) | 0.0046 (6) | 0.0037 (5) | −0.0008 (6) |
O1' | 0.0422 (8) | 0.0778 (10) | 0.0546 (8) | 0.0077 (7) | 0.0037 (6) | 0.0114 (7) |
N1 | 0.0297 (8) | 0.0472 (8) | 0.0446 (8) | 0.0045 (6) | 0.0068 (6) | −0.0010 (6) |
O2 | 0.0341 (8) | 0.1341 (16) | 0.0631 (10) | 0.0079 (9) | 0.0061 (7) | 0.0170 (10) |
O4' | 0.0427 (9) | 0.0877 (12) | 0.0845 (12) | −0.0045 (8) | 0.0080 (8) | 0.0172 (9) |
O2' | 0.0443 (9) | 0.0815 (11) | 0.0917 (13) | −0.0026 (8) | 0.0130 (8) | 0.0032 (10) |
N2 | 0.0387 (9) | 0.0542 (9) | 0.0468 (9) | 0.0072 (7) | 0.0006 (7) | −0.0072 (7) |
N3 | 0.0333 (9) | 0.0752 (12) | 0.0560 (10) | 0.0015 (8) | 0.0114 (7) | 0.0005 (8) |
O1 | 0.0479 (10) | 0.1147 (15) | 0.0903 (13) | −0.0120 (10) | 0.0222 (9) | 0.0255 (11) |
O4 | 0.0375 (9) | 0.1101 (14) | 0.0769 (11) | 0.0044 (8) | −0.0073 (8) | −0.0305 (10) |
O3' | 0.0927 (16) | 0.0810 (12) | 0.0888 (14) | −0.0202 (11) | 0.0326 (12) | 0.0109 (11) |
C1' | 0.0491 (11) | 0.0408 (9) | 0.0442 (9) | 0.0021 (8) | 0.0048 (8) | −0.0074 (7) |
C1 | 0.0318 (9) | 0.0482 (10) | 0.0511 (10) | 0.0044 (7) | 0.0061 (7) | −0.0099 (8) |
C7' | 0.0411 (11) | 0.0518 (10) | 0.0517 (11) | 0.0025 (8) | 0.0078 (8) | −0.0100 (8) |
C8 | 0.0391 (10) | 0.0469 (9) | 0.0474 (10) | 0.0003 (8) | 0.0071 (8) | 0.0036 (8) |
C6 | 0.0315 (10) | 0.0673 (13) | 0.0481 (10) | 0.0081 (9) | 0.0057 (8) | 0.0033 (9) |
C3 | 0.0339 (10) | 0.0502 (10) | 0.0461 (9) | 0.0032 (7) | 0.0076 (7) | −0.0035 (8) |
C2 | 0.0459 (11) | 0.0546 (11) | 0.0445 (10) | 0.0032 (9) | 0.0075 (8) | −0.0003 (8) |
C5 | 0.0411 (11) | 0.0499 (10) | 0.0532 (11) | 0.0095 (9) | 0.0110 (8) | 0.0076 (8) |
C2' | 0.0481 (12) | 0.0484 (10) | 0.0569 (11) | 0.0023 (8) | −0.0017 (9) | −0.0042 (9) |
C7 | 0.0371 (10) | 0.0581 (11) | 0.0472 (10) | 0.0012 (8) | 0.0026 (8) | 0.0017 (8) |
C13 | 0.0543 (14) | 0.0662 (14) | 0.0628 (13) | −0.0018 (11) | 0.0084 (11) | −0.0111 (11) |
C9 | 0.0408 (11) | 0.0693 (13) | 0.0559 (12) | 0.0008 (9) | 0.0040 (9) | −0.0047 (10) |
C3' | 0.0580 (16) | 0.0624 (14) | 0.0941 (19) | 0.0003 (12) | −0.0227 (14) | −0.0016 (13) |
C4 | 0.0343 (12) | 0.0828 (18) | 0.0783 (17) | −0.0058 (11) | 0.0140 (11) | −0.0068 (14) |
C10 | 0.0387 (13) | 0.0857 (17) | 0.0824 (17) | 0.0056 (11) | 0.0097 (11) | −0.0019 (14) |
C12 | 0.0786 (18) | 0.0628 (14) | 0.0718 (15) | 0.0038 (12) | 0.0281 (13) | −0.0111 (12) |
C6' | 0.0806 (17) | 0.0450 (10) | 0.0571 (12) | −0.0043 (10) | 0.0104 (11) | −0.0039 (9) |
C11 | 0.0559 (15) | 0.0649 (14) | 0.0858 (17) | 0.0122 (11) | 0.0286 (13) | 0.0062 (12) |
C4' | 0.106 (3) | 0.0537 (14) | 0.0816 (18) | 0.0071 (14) | −0.0370 (17) | 0.0058 (13) |
C5' | 0.117 (3) | 0.0514 (13) | 0.0667 (15) | −0.0072 (14) | −0.0101 (16) | 0.0113 (12) |
Geometric parameters (Å, º) top
O3—C6 | 1.444 (2) | C6—C5 | 1.495 (3) |
O3—C7 | 1.338 (2) | C6—H6A | 1.02 (2) |
O1'—C7' | 1.282 (3) | C6—H6B | 0.98 (3) |
O1'—H1' | 1.32 (5) | C3—C2 | 1.350 (3) |
N1—C1 | 1.351 (2) | C2—H2 | 0.90 (2) |
N1—C3 | 1.383 (2) | C5—H5A | 0.99 (2) |
N1—C5 | 1.471 (2) | C5—H5B | 0.95 (2) |
O2—N3 | 1.225 (2) | C2'—C3' | 1.389 (3) |
O4'—C2' | 1.345 (3) | C13—C12 | 1.383 (4) |
O4'—H4' | 1.05 (4) | C13—H13 | 0.93 (3) |
O2'—C7' | 1.246 (3) | C9—C10 | 1.381 (3) |
O2'—H2' | 1.38 (5) | C9—H9 | 0.92 (3) |
N2—C1 | 1.322 (3) | C3'—C4' | 1.371 (5) |
N2—C2 | 1.355 (3) | C3'—H3' | 0.96 (3) |
N2—H1' | 1.25 (5) | C4—H4A | 0.92 (4) |
N3—O1 | 1.214 (2) | C4—H4B | 0.95 (4) |
N3—C3 | 1.424 (3) | C4—H4C | 0.92 (5) |
O4—C7 | 1.207 (3) | C10—C11 | 1.359 (4) |
O3'—C6' | 1.356 (3) | C10—H10 | 0.97 (4) |
O3'—H2' | 1.15 (5) | C12—C11 | 1.370 (4) |
C1'—C7' | 1.477 (3) | C12—H12 | 0.94 (3) |
C1'—C2' | 1.408 (3) | C6'—C5' | 1.380 (4) |
C1'—C6' | 1.402 (3) | C11—H11 | 0.97 (3) |
C1—C4 | 1.480 (3) | C4'—C5' | 1.365 (5) |
C8—C7 | 1.481 (3) | C4'—H4'A | 0.96 (4) |
C8—C13 | 1.378 (3) | C5'—H5' | 1.00 (3) |
C8—C9 | 1.385 (3) | | |
| | | |
C7—O3—C6 | 114.21 (15) | C6—C5—H5B | 111.8 (15) |
C7'—O1'—H1' | 105.9 (17) | H5A—C5—H5B | 108.1 (19) |
C1—N1—C3 | 105.86 (15) | O4'—C2'—C1' | 122.70 (19) |
C1—N1—C5 | 125.05 (17) | O4'—C2'—C3' | 117.9 (2) |
C3—N1—C5 | 129.09 (16) | C3'—C2'—C1' | 119.4 (2) |
C2'—O4'—H4' | 104.8 (19) | O3—C7—C8 | 113.92 (17) |
C7'—O2'—H2' | 96.7 (17) | O4—C7—O3 | 122.18 (19) |
C1—N2—C2 | 108.84 (17) | O4—C7—C8 | 123.90 (19) |
C1—N2—H1' | 127.8 (19) | C8—C13—C12 | 120.6 (2) |
C2—N2—H1' | 122.7 (18) | C8—C13—H13 | 119.3 (19) |
O2—N3—C3 | 119.01 (18) | C12—C13—H13 | 120.0 (19) |
O1—N3—O2 | 123.94 (19) | C8—C9—H9 | 116.6 (17) |
O1—N3—C3 | 117.05 (18) | C10—C9—C8 | 119.5 (2) |
C6'—O3'—H2' | 94 (2) | C10—C9—H9 | 123.9 (17) |
C2'—C1'—C7' | 122.29 (19) | C2'—C3'—H3' | 112 (2) |
C6'—C1'—C7' | 118.7 (2) | C4'—C3'—C2' | 119.9 (3) |
C6'—C1'—C2' | 118.9 (2) | C4'—C3'—H3' | 127.4 (19) |
N1—C1—C4 | 125.5 (2) | C1—C4—H4A | 112 (2) |
N2—C1—N1 | 109.75 (17) | C1—C4—H4B | 109 (3) |
N2—C1—C4 | 124.8 (2) | C1—C4—H4C | 107 (3) |
O1'—C7'—C1' | 117.54 (18) | H4A—C4—H4B | 113 (4) |
O2'—C7'—O1' | 121.3 (2) | H4A—C4—H4C | 111 (4) |
O2'—C7'—C1' | 121.1 (2) | H4B—C4—H4C | 104 (4) |
C13—C8—C7 | 118.26 (19) | C9—C10—H10 | 118 (2) |
C13—C8—C9 | 119.1 (2) | C11—C10—C9 | 121.0 (2) |
C9—C8—C7 | 122.66 (19) | C11—C10—H10 | 121 (2) |
O3—C6—C5 | 108.75 (16) | C13—C12—H12 | 118.5 (19) |
O3—C6—H6A | 108.1 (13) | C11—C12—C13 | 119.7 (2) |
O3—C6—H6B | 108.8 (15) | C11—C12—H12 | 121.8 (19) |
C5—C6—H6A | 111.4 (13) | O3'—C6'—C1' | 121.5 (2) |
C5—C6—H6B | 109.4 (14) | O3'—C6'—C5' | 118.2 (3) |
H6A—C6—H6B | 110 (2) | C5'—C6'—C1' | 120.3 (3) |
N1—C3—N3 | 124.52 (17) | C10—C11—C12 | 120.0 (2) |
C2—C3—N1 | 108.34 (17) | C10—C11—H11 | 122.8 (17) |
C2—C3—N3 | 127.11 (19) | C12—C11—H11 | 117.2 (17) |
N2—C2—H2 | 125.8 (17) | C3'—C4'—H4'A | 126 (2) |
C3—C2—N2 | 107.21 (19) | C5'—C4'—C3' | 121.6 (3) |
C3—C2—H2 | 126.8 (17) | C5'—C4'—H4'A | 113 (2) |
N1—C5—C6 | 113.14 (17) | C6'—C5'—H5' | 115 (2) |
N1—C5—H5A | 106.2 (13) | C4'—C5'—C6' | 119.8 (3) |
N1—C5—H5B | 105.5 (14) | C4'—C5'—H5' | 126 (2) |
C6—C5—H5A | 111.6 (13) | | |
2-(2-Methyl-5-nitro-1
H-imidazol-1-yl)ethyl benzoate–3,5-dihydroxybenzoic acid (3/1) (bzmd35dba)
top
Crystal data top
3C13H13N3O4·C7H6O4 | F(000) = 2048 |
Mr = 979.91 | Dx = 1.394 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 7.1481 (2) Å | Cell parameters from 9896 reflections |
b = 36.7892 (8) Å | θ = 3.5–67.6° |
c = 18.0584 (4) Å | µ = 0.91 mm−1 |
β = 100.451 (1)° | T = 300 K |
V = 4670.1 (2) Å3 | Prism, clear light colourless |
Z = 4 | 0.28 × 0.14 × 0.06 mm |
Data collection top
Bruker APEXII CCD diffractometer | 5499 reflections with I > 2σ(I) |
Multilayer mirrors monochromator | Rint = 0.058 |
φ and ω scans | θmax = 68.7°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −7→8 |
Tmin = 0.835, Tmax = 0.986 | k = −44→44 |
56516 measured reflections | l = −21→21 |
8547 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.052 | w = 1/[σ2(Fo2) + (0.0833P)2 + 2.1514P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.176 | (Δ/σ)max = 0.002 |
S = 1.01 | Δρmax = 0.27 e Å−3 |
8547 reflections | Δρmin = −0.21 e Å−3 |
844 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.00125 (13) |
Primary atom site location: dual | |
Special details top
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1C | 0.8254 (4) | 0.36199 (7) | −0.06761 (14) | 0.0939 (7) | |
O2C | 0.5826 (4) | 0.32866 (7) | −0.11345 (12) | 0.0874 (7) | |
O3C | 0.3392 (3) | 0.26359 (5) | 0.03750 (10) | 0.0688 (5) | |
O3A | 0.7853 (3) | 0.47087 (5) | 0.86671 (10) | 0.0634 (5) | |
N1A | 0.9537 (3) | 0.51097 (6) | 0.74799 (11) | 0.0540 (5) | |
O3B | 0.7069 (3) | 0.71873 (5) | 0.49400 (11) | 0.0704 (5) | |
O3' | 0.5229 (3) | 0.56376 (5) | 0.34945 (12) | 0.0766 (6) | |
O4' | 0.8266 (3) | 0.46389 (5) | 0.49620 (11) | 0.0721 (6) | |
O4C | 0.2932 (4) | 0.20905 (6) | −0.01637 (14) | 0.0909 (7) | |
N1C | 0.4294 (3) | 0.33992 (6) | 0.01710 (12) | 0.0571 (5) | |
N2C | 0.5611 (4) | 0.37320 (7) | 0.11443 (14) | 0.0772 (7) | |
N3C | 0.6713 (4) | 0.34779 (7) | −0.06396 (14) | 0.0668 (6) | |
C1C | 0.4139 (5) | 0.35240 (8) | 0.08614 (16) | 0.0697 (8) | |
C2C | 0.6752 (5) | 0.37470 (8) | 0.06255 (18) | 0.0705 (8) | |
H2C | 0.785 (5) | 0.3879 (9) | 0.0685 (17) | 0.074 (9)* | |
C3C | 0.5974 (4) | 0.35420 (7) | 0.00232 (15) | 0.0578 (6) | |
C4C | 0.2524 (9) | 0.34396 (14) | 0.1246 (3) | 0.1032 (14) | |
H4CA | 0.207 (7) | 0.3175 (15) | 0.123 (3) | 0.154 (19)* | |
H4CB | 0.284 (7) | 0.3513 (15) | 0.170 (3) | 0.15 (2)* | |
H4CC | 0.140 (10) | 0.3572 (18) | 0.104 (3) | 0.19 (3)* | |
C5C | 0.2834 (4) | 0.31870 (8) | −0.03207 (18) | 0.0639 (7) | |
H5CA | 0.260 (4) | 0.3289 (8) | −0.0824 (17) | 0.069 (8)* | |
H5CB | 0.161 (5) | 0.3213 (8) | −0.0124 (16) | 0.075 (9)* | |
C6C | 0.3292 (5) | 0.27923 (8) | −0.03625 (16) | 0.0651 (7) | |
H6CA | 0.454 (5) | 0.2757 (9) | −0.0532 (18) | 0.085 (10)* | |
H6CB | 0.231 (4) | 0.2679 (8) | −0.0697 (16) | 0.063 (8)* | |
C7C | 0.3174 (4) | 0.22757 (8) | 0.03984 (18) | 0.0659 (7) | |
C14C | 0.332 (6) | 0.2182 (8) | 0.1204 (10) | 0.068 (6) | 0.5318 |
C15C | 0.390 (4) | 0.2413 (5) | 0.1819 (15) | 0.068 (3) | 0.5318 |
H15C | 0.419867 | 0.265318 | 0.173166 | 0.082* | 0.5318 |
C16C | 0.403 (2) | 0.2292 (5) | 0.2561 (9) | 0.093 (4) | 0.5318 |
H16C | 0.434781 | 0.245824 | 0.295117 | 0.112* | 0.5318 |
C17C | 0.370 (2) | 0.1927 (6) | 0.2740 (8) | 0.112 (5) | 0.5318 |
H17C | 0.385648 | 0.184515 | 0.323553 | 0.135* | 0.5318 |
C18C | 0.310 (2) | 0.1691 (4) | 0.2119 (7) | 0.101 (6) | 0.5318 |
H18C | 0.277796 | 0.145168 | 0.220181 | 0.121* | 0.5318 |
C19C | 0.300 (3) | 0.1817 (6) | 0.1385 (13) | 0.088 (4) | 0.5318 |
H19C | 0.270497 | 0.165123 | 0.099208 | 0.105* | 0.5318 |
C8C | 0.322 (6) | 0.2090 (9) | 0.1134 (10) | 0.062 (6) | 0.4682 |
C13C | 0.364 (4) | 0.2293 (6) | 0.176 (2) | 0.081 (6) | 0.4682 |
H13C | 0.392618 | 0.253879 | 0.173808 | 0.097* | 0.4682 |
C12C | 0.362 (3) | 0.2123 (5) | 0.2448 (12) | 0.099 (6) | 0.4682 |
H12C | 0.390847 | 0.225357 | 0.289514 | 0.119* | 0.4682 |
C11C | 0.317 (3) | 0.1770 (6) | 0.2460 (7) | 0.094 (5) | 0.4682 |
H11C | 0.317949 | 0.165177 | 0.291564 | 0.113* | 0.4682 |
C10C | 0.269 (3) | 0.1580 (6) | 0.1779 (9) | 0.109 (6) | 0.4682 |
H10C | 0.238908 | 0.133490 | 0.179162 | 0.130* | 0.4682 |
C9C | 0.266 (4) | 0.1735 (6) | 0.1132 (13) | 0.081 (5) | 0.4682 |
H9C | 0.226439 | 0.160916 | 0.068431 | 0.097* | 0.4682 |
O1A | 0.8622 (4) | 0.60568 (6) | 0.72428 (15) | 0.1031 (8) | |
O2A | 0.9845 (4) | 0.57753 (6) | 0.82685 (13) | 0.0913 (7) | |
O4A | 0.7325 (4) | 0.47827 (10) | 0.98395 (13) | 0.1178 (10) | |
N2A | 0.8422 (3) | 0.50522 (6) | 0.62493 (12) | 0.0589 (5) | |
N3A | 0.9160 (4) | 0.57788 (7) | 0.75940 (15) | 0.0722 (7) | |
C1A | 0.9167 (4) | 0.48799 (7) | 0.68826 (14) | 0.0548 (6) | |
C2A | 0.8300 (4) | 0.54068 (8) | 0.64394 (16) | 0.0613 (7) | |
H2A | 0.782 (4) | 0.5591 (8) | 0.6103 (18) | 0.076 (9)* | |
C3A | 0.8979 (4) | 0.54472 (7) | 0.71862 (15) | 0.0574 (6) | |
C4A | 0.9548 (6) | 0.44854 (9) | 0.6922 (2) | 0.0726 (8) | |
H4AA | 1.089 (6) | 0.4430 (11) | 0.708 (2) | 0.112 (14)* | |
H4AB | 0.892 (5) | 0.4370 (10) | 0.731 (2) | 0.106 (12)* | |
H4AC | 0.902 (6) | 0.4365 (11) | 0.648 (3) | 0.122 (14)* | |
C5A | 1.0501 (4) | 0.50018 (10) | 0.82398 (15) | 0.0628 (7) | |
H5AA | 1.146 (4) | 0.5180 (8) | 0.8411 (16) | 0.073 (9)* | |
H5AB | 1.104 (5) | 0.4746 (10) | 0.8180 (18) | 0.085 (10)* | |
C6A | 0.9251 (5) | 0.49971 (10) | 0.88285 (16) | 0.0666 (7) | |
H6AA | 1.011 (4) | 0.4945 (8) | 0.9322 (18) | 0.078 (9)* | |
H6AB | 0.859 (5) | 0.5241 (10) | 0.8861 (18) | 0.091 (11)* | |
C7A | 0.6892 (4) | 0.46458 (9) | 0.92272 (16) | 0.0726 (8) | |
C8A | 0.5226 (4) | 0.44060 (9) | 0.90204 (17) | 0.0701 (8) | |
C9A | 0.4877 (5) | 0.42069 (9) | 0.8363 (2) | 0.0777 (9) | |
H9A | 0.580 (4) | 0.4208 (8) | 0.8021 (17) | 0.072 (9)* | |
C10A | 0.3229 (6) | 0.39958 (10) | 0.8191 (3) | 0.0967 (13) | |
H10A | 0.307 (6) | 0.3863 (11) | 0.770 (2) | 0.117 (14)* | |
C11A | 0.1962 (6) | 0.39897 (12) | 0.8675 (3) | 0.1073 (15) | |
H11A | 0.073 (7) | 0.3852 (12) | 0.856 (3) | 0.135 (16)* | |
C12A | 0.2295 (6) | 0.41829 (12) | 0.9333 (3) | 0.1003 (13) | |
H12A | 0.134 (6) | 0.4175 (11) | 0.969 (2) | 0.115 (13)* | |
C13A | 0.3934 (5) | 0.43885 (11) | 0.9514 (2) | 0.0867 (10) | |
H13A | 0.422 (6) | 0.4556 (11) | 0.993 (2) | 0.107 (14)* | |
O1B | 0.2377 (4) | 0.64048 (6) | 0.62852 (13) | 0.0840 (6) | |
O2B | 0.4848 (4) | 0.67270 (7) | 0.67579 (13) | 0.0956 (8) | |
O4B | 0.6319 (4) | 0.77703 (6) | 0.50557 (12) | 0.0850 (7) | |
N1B | 0.6714 (3) | 0.64843 (6) | 0.56085 (12) | 0.0595 (5) | |
N2B | 0.5676 (4) | 0.60475 (6) | 0.47891 (13) | 0.0670 (6) | |
N3B | 0.4023 (4) | 0.65101 (7) | 0.62963 (14) | 0.0713 (7) | |
C1B | 0.7086 (4) | 0.62802 (7) | 0.50247 (16) | 0.0645 (7) | |
C2B | 0.4352 (5) | 0.61020 (8) | 0.52319 (17) | 0.0656 (7) | |
H2B | 0.320 (4) | 0.5970 (8) | 0.5189 (16) | 0.066 (8)* | |
C3B | 0.4962 (4) | 0.63698 (7) | 0.57283 (15) | 0.0596 (7) | |
C4B | 0.8810 (5) | 0.63092 (11) | 0.4683 (2) | 0.0961 (11) | |
H4BA | 0.890475 | 0.655102 | 0.449353 | 0.144* | |
H4BB | 0.873150 | 0.613816 | 0.427700 | 0.144* | |
H4BC | 0.991440 | 0.625719 | 0.505677 | 0.144* | |
C5B | 0.7922 (5) | 0.67798 (8) | 0.5974 (2) | 0.0694 (8) | |
H5BA | 0.807 (5) | 0.6749 (9) | 0.652 (2) | 0.087 (10)* | |
H5BB | 0.912 (5) | 0.6750 (8) | 0.5815 (16) | 0.072 (9)* | |
C6B | 0.7111 (5) | 0.71471 (8) | 0.57400 (17) | 0.0683 (8) | |
H6BA | 0.786 (4) | 0.7336 (8) | 0.6008 (16) | 0.063 (8)* | |
H6BB | 0.574 (5) | 0.7165 (8) | 0.5825 (17) | 0.078 (9)* | |
C7B | 0.6616 (4) | 0.75204 (8) | 0.46585 (16) | 0.0633 (7) | |
C8B | 0.6546 (4) | 0.75459 (8) | 0.38362 (16) | 0.0656 (7) | |
C9B | 0.6406 (5) | 0.72461 (11) | 0.3370 (2) | 0.0789 (9) | |
H9B | 0.642 (4) | 0.7020 (8) | 0.3596 (16) | 0.065 (9)* | |
C10B | 0.6313 (6) | 0.72971 (15) | 0.2597 (2) | 0.0979 (12) | |
H10B | 0.631 (5) | 0.7072 (11) | 0.233 (2) | 0.111 (13)* | |
C11B | 0.6431 (6) | 0.76410 (15) | 0.2314 (2) | 0.1012 (12) | |
H11B | 0.643 (6) | 0.7687 (12) | 0.175 (3) | 0.139 (16)* | |
C12B | 0.6565 (6) | 0.79407 (14) | 0.2768 (2) | 0.0951 (11) | |
H12B | 0.670 (7) | 0.8222 (16) | 0.256 (3) | 0.17 (2)* | |
C13B | 0.6609 (5) | 0.78897 (11) | 0.3529 (2) | 0.0802 (9) | |
H13B | 0.664 (5) | 0.8100 (9) | 0.3852 (19) | 0.082 (10)* | |
O1' | 0.6210 (4) | 0.41366 (6) | 0.24229 (12) | 0.0924 (8) | |
H1' | 0.593 (6) | 0.4002 (12) | 0.194 (3) | 0.130 (15)* | |
O2' | 0.4848 (4) | 0.45805 (6) | 0.17062 (11) | 0.0929 (8) | |
H3' | 0.540 (5) | 0.5769 (11) | 0.397 (2) | 0.111 (13)* | |
H4' | 0.829 (6) | 0.4799 (11) | 0.538 (2) | 0.118 (13)* | |
C1' | 0.6075 (3) | 0.47064 (6) | 0.29968 (12) | 0.0478 (5) | |
C2' | 0.5473 (4) | 0.50641 (7) | 0.29381 (14) | 0.0538 (6) | |
H2' | 0.485 (4) | 0.5175 (8) | 0.2465 (16) | 0.066 (8)* | |
C3' | 0.5826 (4) | 0.52839 (7) | 0.35727 (14) | 0.0547 (6) | |
C4' | 0.6741 (4) | 0.51454 (7) | 0.42558 (14) | 0.0547 (6) | |
H4'A | 0.695 (4) | 0.5297 (8) | 0.4690 (16) | 0.066 (8)* | |
C5' | 0.7340 (4) | 0.47867 (7) | 0.43047 (13) | 0.0538 (6) | |
C6' | 0.7015 (4) | 0.45642 (7) | 0.36715 (14) | 0.0525 (6) | |
H6' | 0.745 (4) | 0.4308 (7) | 0.3716 (14) | 0.056 (7)* | |
C7' | 0.5633 (4) | 0.44730 (7) | 0.23118 (14) | 0.0547 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1C | 0.0824 (16) | 0.1000 (17) | 0.1057 (18) | −0.0177 (14) | 0.0339 (14) | 0.0013 (13) |
O2C | 0.0938 (16) | 0.1079 (17) | 0.0617 (12) | −0.0126 (14) | 0.0174 (12) | −0.0190 (12) |
O3C | 0.0881 (14) | 0.0579 (11) | 0.0581 (11) | −0.0031 (10) | 0.0070 (10) | −0.0047 (8) |
O3A | 0.0616 (11) | 0.0758 (12) | 0.0500 (10) | −0.0110 (9) | 0.0026 (8) | 0.0045 (8) |
N1A | 0.0514 (12) | 0.0630 (12) | 0.0460 (11) | −0.0034 (10) | 0.0046 (9) | 0.0001 (9) |
O3B | 0.0864 (14) | 0.0615 (11) | 0.0644 (12) | −0.0020 (10) | 0.0164 (10) | −0.0104 (9) |
O3' | 0.1090 (17) | 0.0550 (11) | 0.0595 (12) | 0.0166 (11) | −0.0012 (11) | −0.0068 (9) |
O4' | 0.0980 (16) | 0.0601 (11) | 0.0497 (11) | 0.0065 (10) | −0.0089 (10) | −0.0005 (9) |
O4C | 0.116 (2) | 0.0611 (12) | 0.0930 (16) | −0.0062 (12) | 0.0128 (14) | −0.0160 (11) |
N1C | 0.0628 (14) | 0.0536 (12) | 0.0546 (12) | 0.0006 (10) | 0.0095 (10) | −0.0075 (9) |
N2C | 0.104 (2) | 0.0613 (14) | 0.0633 (15) | 0.0020 (14) | 0.0076 (15) | −0.0174 (11) |
N3C | 0.0673 (16) | 0.0680 (14) | 0.0659 (15) | −0.0002 (12) | 0.0147 (12) | 0.0021 (12) |
C1C | 0.090 (2) | 0.0590 (16) | 0.0627 (17) | 0.0081 (16) | 0.0208 (16) | −0.0108 (13) |
C2C | 0.080 (2) | 0.0572 (16) | 0.0690 (19) | −0.0039 (16) | 0.0005 (16) | −0.0073 (13) |
C3C | 0.0616 (16) | 0.0537 (14) | 0.0570 (15) | −0.0024 (12) | 0.0075 (12) | −0.0062 (11) |
C4C | 0.121 (4) | 0.102 (3) | 0.103 (3) | 0.003 (3) | 0.062 (3) | −0.019 (3) |
C5C | 0.0621 (18) | 0.0632 (16) | 0.0633 (17) | −0.0010 (14) | 0.0028 (14) | −0.0020 (13) |
C6C | 0.077 (2) | 0.0599 (16) | 0.0555 (16) | −0.0066 (15) | 0.0039 (15) | −0.0061 (12) |
C7C | 0.0581 (17) | 0.0605 (16) | 0.0777 (19) | 0.0021 (13) | 0.0089 (14) | 0.0006 (14) |
C14C | 0.056 (6) | 0.054 (13) | 0.098 (10) | 0.007 (8) | 0.024 (7) | 0.010 (8) |
C15C | 0.065 (7) | 0.081 (9) | 0.059 (5) | −0.005 (7) | 0.013 (5) | 0.002 (7) |
C16C | 0.074 (6) | 0.136 (13) | 0.072 (8) | −0.007 (7) | 0.021 (5) | 0.011 (7) |
C17C | 0.083 (8) | 0.183 (16) | 0.073 (10) | 0.020 (8) | 0.019 (7) | 0.038 (9) |
C18C | 0.126 (9) | 0.123 (15) | 0.063 (13) | 0.014 (9) | 0.043 (12) | 0.038 (11) |
C19C | 0.084 (7) | 0.068 (10) | 0.114 (14) | 0.003 (6) | 0.027 (8) | 0.007 (8) |
C8C | 0.066 (8) | 0.054 (15) | 0.067 (6) | 0.011 (10) | 0.017 (5) | 0.005 (6) |
C13C | 0.070 (9) | 0.087 (13) | 0.086 (10) | −0.007 (9) | 0.015 (8) | 0.011 (13) |
C12C | 0.094 (12) | 0.14 (2) | 0.063 (8) | 0.015 (11) | 0.010 (7) | −0.002 (10) |
C11C | 0.093 (9) | 0.155 (15) | 0.036 (10) | 0.032 (8) | 0.021 (8) | 0.029 (10) |
C10C | 0.150 (14) | 0.101 (10) | 0.088 (13) | 0.036 (9) | 0.056 (11) | 0.020 (8) |
C9C | 0.100 (12) | 0.058 (9) | 0.095 (11) | 0.005 (7) | 0.044 (10) | 0.007 (6) |
O1A | 0.137 (2) | 0.0657 (14) | 0.1079 (19) | 0.0135 (14) | 0.0244 (17) | −0.0030 (13) |
O2A | 0.1095 (19) | 0.0871 (15) | 0.0741 (15) | −0.0183 (13) | 0.0079 (13) | −0.0214 (11) |
O4A | 0.1005 (19) | 0.196 (3) | 0.0587 (14) | −0.052 (2) | 0.0189 (13) | −0.0193 (16) |
N2A | 0.0597 (13) | 0.0659 (13) | 0.0497 (12) | −0.0009 (11) | 0.0058 (10) | 0.0008 (10) |
N3A | 0.0755 (17) | 0.0693 (16) | 0.0738 (17) | −0.0062 (13) | 0.0188 (14) | −0.0087 (13) |
C1A | 0.0532 (15) | 0.0615 (15) | 0.0478 (13) | −0.0055 (12) | 0.0042 (11) | −0.0006 (11) |
C2A | 0.0597 (17) | 0.0686 (17) | 0.0553 (15) | 0.0032 (14) | 0.0094 (13) | 0.0067 (13) |
C3A | 0.0550 (15) | 0.0584 (15) | 0.0587 (15) | −0.0015 (12) | 0.0102 (12) | −0.0027 (12) |
C4A | 0.083 (2) | 0.0656 (18) | 0.0656 (19) | −0.0013 (17) | 0.0029 (18) | −0.0013 (15) |
C5A | 0.0545 (16) | 0.082 (2) | 0.0474 (14) | −0.0103 (16) | −0.0024 (12) | 0.0011 (13) |
C6A | 0.0629 (18) | 0.084 (2) | 0.0497 (15) | −0.0158 (16) | 0.0029 (13) | −0.0046 (13) |
C7A | 0.0642 (18) | 0.099 (2) | 0.0526 (16) | −0.0075 (16) | 0.0065 (14) | 0.0075 (15) |
C8A | 0.0601 (17) | 0.0775 (19) | 0.0684 (18) | −0.0014 (15) | 0.0002 (14) | 0.0213 (15) |
C9A | 0.075 (2) | 0.0714 (19) | 0.080 (2) | −0.0069 (17) | −0.0042 (18) | 0.0225 (16) |
C10A | 0.096 (3) | 0.073 (2) | 0.106 (3) | −0.017 (2) | −0.022 (2) | 0.025 (2) |
C11A | 0.075 (3) | 0.091 (3) | 0.147 (4) | −0.015 (2) | −0.004 (3) | 0.054 (3) |
C12A | 0.070 (2) | 0.098 (3) | 0.132 (4) | 0.000 (2) | 0.016 (3) | 0.048 (3) |
C13A | 0.072 (2) | 0.089 (2) | 0.100 (3) | 0.0007 (19) | 0.018 (2) | 0.030 (2) |
O1B | 0.0854 (16) | 0.0831 (14) | 0.0907 (16) | 0.0068 (12) | 0.0346 (13) | 0.0075 (11) |
O2B | 0.119 (2) | 0.0971 (17) | 0.0754 (14) | −0.0060 (15) | 0.0307 (14) | −0.0279 (13) |
O4B | 0.1183 (19) | 0.0642 (12) | 0.0757 (13) | 0.0054 (12) | 0.0259 (13) | −0.0099 (10) |
N1B | 0.0624 (14) | 0.0547 (12) | 0.0617 (13) | 0.0001 (10) | 0.0124 (11) | −0.0074 (10) |
N2B | 0.0788 (16) | 0.0565 (13) | 0.0677 (14) | 0.0021 (12) | 0.0185 (12) | −0.0091 (11) |
N3B | 0.0839 (19) | 0.0675 (15) | 0.0669 (15) | 0.0051 (14) | 0.0255 (13) | 0.0013 (12) |
C1B | 0.0701 (18) | 0.0575 (15) | 0.0682 (17) | 0.0022 (14) | 0.0184 (14) | −0.0096 (13) |
C2B | 0.073 (2) | 0.0566 (15) | 0.0691 (18) | 0.0000 (15) | 0.0184 (15) | −0.0025 (13) |
C3B | 0.0700 (18) | 0.0549 (14) | 0.0556 (15) | 0.0033 (13) | 0.0160 (13) | −0.0023 (11) |
C4B | 0.082 (2) | 0.108 (3) | 0.107 (3) | −0.003 (2) | 0.040 (2) | −0.027 (2) |
C5B | 0.071 (2) | 0.0659 (17) | 0.068 (2) | −0.0021 (15) | 0.0047 (16) | −0.0121 (14) |
C6B | 0.082 (2) | 0.0601 (16) | 0.0617 (17) | −0.0084 (16) | 0.0107 (15) | −0.0123 (13) |
C7B | 0.0599 (17) | 0.0608 (16) | 0.0692 (17) | −0.0066 (13) | 0.0118 (14) | −0.0101 (13) |
C8B | 0.0540 (16) | 0.0779 (19) | 0.0640 (17) | −0.0071 (14) | 0.0081 (13) | −0.0126 (14) |
C9B | 0.070 (2) | 0.087 (2) | 0.079 (2) | −0.0118 (18) | 0.0120 (16) | −0.0207 (18) |
C10B | 0.083 (3) | 0.130 (4) | 0.079 (2) | −0.007 (2) | 0.0084 (19) | −0.038 (3) |
C11B | 0.085 (3) | 0.147 (4) | 0.071 (2) | 0.002 (3) | 0.011 (2) | 0.002 (3) |
C12B | 0.092 (3) | 0.120 (3) | 0.073 (2) | 0.000 (2) | 0.0145 (19) | 0.010 (2) |
C13B | 0.079 (2) | 0.085 (2) | 0.076 (2) | −0.0051 (18) | 0.0126 (17) | −0.0013 (18) |
O1' | 0.151 (2) | 0.0591 (12) | 0.0587 (12) | 0.0135 (13) | −0.0021 (13) | −0.0159 (10) |
O2' | 0.130 (2) | 0.0837 (15) | 0.0529 (12) | 0.0226 (14) | −0.0171 (12) | −0.0174 (10) |
C1' | 0.0488 (13) | 0.0526 (13) | 0.0419 (12) | −0.0064 (11) | 0.0078 (10) | −0.0060 (10) |
C2' | 0.0589 (16) | 0.0548 (14) | 0.0457 (13) | −0.0004 (12) | 0.0038 (11) | −0.0022 (11) |
C3' | 0.0602 (16) | 0.0490 (13) | 0.0540 (14) | 0.0010 (12) | 0.0083 (12) | −0.0047 (11) |
C4' | 0.0638 (16) | 0.0545 (14) | 0.0430 (13) | −0.0027 (12) | 0.0020 (12) | −0.0084 (11) |
C5' | 0.0581 (15) | 0.0565 (14) | 0.0441 (13) | −0.0025 (12) | 0.0023 (11) | −0.0014 (10) |
C6' | 0.0576 (15) | 0.0489 (14) | 0.0498 (13) | −0.0013 (12) | 0.0067 (11) | −0.0038 (10) |
C7' | 0.0569 (15) | 0.0583 (15) | 0.0486 (14) | −0.0037 (12) | 0.0084 (12) | −0.0073 (11) |
Geometric parameters (Å, º) top
O1C—N3C | 1.232 (3) | C4A—H4AA | 0.97 (4) |
O2C—N3C | 1.221 (3) | C4A—H4AB | 1.00 (4) |
O3C—C6C | 1.440 (3) | C4A—H4AC | 0.94 (5) |
O3C—C7C | 1.336 (3) | C5A—H5AA | 0.96 (3) |
O3A—C6A | 1.450 (3) | C5A—H5AB | 1.03 (3) |
O3A—C7A | 1.342 (3) | C5A—C6A | 1.508 (4) |
N1A—C1A | 1.358 (3) | C6A—H6AA | 1.00 (3) |
N1A—C3A | 1.380 (3) | C6A—H6AB | 1.02 (4) |
N1A—C5A | 1.474 (3) | C7A—C8A | 1.475 (4) |
O3B—C6B | 1.447 (3) | C8A—C9A | 1.379 (5) |
O3B—C7B | 1.344 (3) | C8A—C13A | 1.396 (5) |
O3'—H3' | 0.97 (4) | C9A—H9A | 0.98 (3) |
O3'—C3' | 1.369 (3) | C9A—C10A | 1.398 (5) |
O4'—H4' | 0.96 (4) | C10A—H10A | 0.99 (4) |
O4'—C5' | 1.363 (3) | C10A—C11A | 1.368 (7) |
O4C—C7C | 1.209 (4) | C11A—H11A | 1.00 (5) |
N1C—C1C | 1.352 (3) | C11A—C12A | 1.368 (7) |
N1C—C3C | 1.381 (3) | C12A—H12A | 1.03 (4) |
N1C—C5C | 1.466 (3) | C12A—C13A | 1.382 (6) |
N2C—C1C | 1.326 (4) | C13A—H13A | 0.96 (4) |
N2C—C2C | 1.350 (4) | O1B—N3B | 1.235 (3) |
N3C—C3C | 1.413 (3) | O2B—N3B | 1.225 (3) |
C1C—C4C | 1.484 (5) | O4B—C7B | 1.208 (3) |
C2C—H2C | 0.92 (3) | N1B—C1B | 1.359 (3) |
C2C—C3C | 1.357 (4) | N1B—C3B | 1.375 (3) |
C4C—H4CA | 1.02 (5) | N1B—C5B | 1.468 (4) |
C4C—H4CB | 0.85 (6) | N2B—C1B | 1.332 (4) |
C4C—H4CC | 0.95 (7) | N2B—C2B | 1.360 (4) |
C5C—H5CA | 0.97 (3) | N3B—C3B | 1.421 (3) |
C5C—H5CB | 1.01 (3) | C1B—C4B | 1.479 (4) |
C5C—C6C | 1.493 (4) | C2B—H2B | 0.95 (3) |
C6C—H6CA | 1.00 (3) | C2B—C3B | 1.350 (4) |
C6C—H6CB | 0.94 (3) | C4B—H4BA | 0.9600 |
C7C—C14C | 1.480 (13) | C4B—H4BB | 0.9600 |
C7C—C8C | 1.489 (12) | C4B—H4BC | 0.9600 |
C14C—C15C | 1.40 (3) | C5B—H5BA | 0.98 (3) |
C14C—C19C | 1.41 (3) | C5B—H5BB | 0.96 (3) |
C15C—H15C | 0.9300 | C5B—C6B | 1.500 (4) |
C15C—C16C | 1.40 (3) | C6B—H6BA | 0.95 (3) |
C16C—H16C | 0.9300 | C6B—H6BB | 1.02 (3) |
C16C—C17C | 1.41 (3) | C7B—C8B | 1.480 (4) |
C17C—H17C | 0.9300 | C8B—C9B | 1.380 (4) |
C17C—C18C | 1.42 (2) | C8B—C13B | 1.386 (5) |
C18C—H18C | 0.9300 | C9B—H9B | 0.93 (3) |
C18C—C19C | 1.39 (3) | C9B—C10B | 1.399 (5) |
C19C—H19C | 0.9300 | C10B—H10B | 0.96 (4) |
C8C—C13C | 1.35 (4) | C10B—C11B | 1.372 (6) |
C8C—C9C | 1.37 (4) | C11B—H11B | 1.04 (5) |
C13C—H13C | 0.9300 | C11B—C12B | 1.367 (6) |
C13C—C12C | 1.39 (4) | C12B—H12B | 1.11 (6) |
C12C—H12C | 0.9300 | C12B—C13B | 1.381 (5) |
C12C—C11C | 1.34 (3) | C13B—H13B | 0.97 (3) |
C11C—H11C | 0.9300 | O1'—H1' | 0.99 (5) |
C11C—C10C | 1.402 (19) | O1'—C7' | 1.308 (3) |
C10C—H10C | 0.9300 | O2'—C7' | 1.202 (3) |
C10C—C9C | 1.29 (4) | C1'—C2' | 1.383 (3) |
C9C—H9C | 0.9300 | C1'—C6' | 1.383 (3) |
O1A—N3A | 1.228 (3) | C1'—C7' | 1.492 (3) |
O2A—N3A | 1.228 (3) | C2'—H2' | 0.98 (3) |
O4A—C7A | 1.203 (4) | C2'—C3' | 1.388 (3) |
N2A—C1A | 1.331 (3) | C3'—C4' | 1.384 (3) |
N2A—C2A | 1.356 (4) | C4'—H4'A | 0.95 (3) |
N3A—C3A | 1.419 (4) | C4'—C5' | 1.385 (4) |
C1A—C4A | 1.476 (4) | C5'—C6' | 1.391 (3) |
C2A—H2A | 0.93 (3) | C6'—H6' | 0.99 (3) |
C2A—C3A | 1.356 (4) | | |
| | | |
C7C—O3C—C6C | 116.0 (2) | C6A—C5A—H5AA | 105.1 (18) |
C7A—O3A—C6A | 113.8 (2) | C6A—C5A—H5AB | 110.2 (18) |
C1A—N1A—C3A | 104.7 (2) | O3A—C6A—C5A | 110.0 (2) |
C1A—N1A—C5A | 124.2 (2) | O3A—C6A—H6AA | 108.9 (17) |
C3A—N1A—C5A | 130.8 (2) | O3A—C6A—H6AB | 110 (2) |
C7B—O3B—C6B | 115.5 (2) | C5A—C6A—H6AA | 106.5 (18) |
C3'—O3'—H3' | 113 (2) | C5A—C6A—H6AB | 111.7 (19) |
C5'—O4'—H4' | 112 (2) | H6AA—C6A—H6AB | 109 (3) |
C1C—N1C—C3C | 105.6 (2) | O3A—C7A—C8A | 114.4 (3) |
C1C—N1C—C5C | 124.8 (3) | O4A—C7A—O3A | 122.6 (3) |
C3C—N1C—C5C | 129.3 (2) | O4A—C7A—C8A | 123.0 (3) |
C1C—N2C—C2C | 107.1 (2) | C9A—C8A—C7A | 123.2 (3) |
O1C—N3C—C3C | 116.7 (3) | C9A—C8A—C13A | 119.2 (3) |
O2C—N3C—O1C | 123.8 (3) | C13A—C8A—C7A | 117.6 (3) |
O2C—N3C—C3C | 119.5 (2) | C8A—C9A—H9A | 120.2 (19) |
N1C—C1C—C4C | 124.1 (3) | C8A—C9A—C10A | 119.9 (4) |
N2C—C1C—N1C | 111.1 (3) | C10A—C9A—H9A | 119.9 (19) |
N2C—C1C—C4C | 124.8 (3) | C9A—C10A—H10A | 115 (3) |
N2C—C2C—H2C | 124 (2) | C11A—C10A—C9A | 119.8 (5) |
N2C—C2C—C3C | 108.8 (3) | C11A—C10A—H10A | 125 (3) |
C3C—C2C—H2C | 128 (2) | C10A—C11A—H11A | 122 (3) |
N1C—C3C—N3C | 124.9 (2) | C10A—C11A—C12A | 121.0 (4) |
C2C—C3C—N1C | 107.5 (3) | C12A—C11A—H11A | 117 (3) |
C2C—C3C—N3C | 127.6 (3) | C11A—C12A—H12A | 120 (2) |
C1C—C4C—H4CA | 117 (3) | C11A—C12A—C13A | 119.7 (5) |
C1C—C4C—H4CB | 107 (4) | C13A—C12A—H12A | 120 (2) |
C1C—C4C—H4CC | 113 (4) | C8A—C13A—H13A | 113 (3) |
H4CA—C4C—H4CB | 110 (5) | C12A—C13A—C8A | 120.3 (5) |
H4CA—C4C—H4CC | 104 (5) | C12A—C13A—H13A | 126 (3) |
H4CB—C4C—H4CC | 105 (5) | C1B—N1B—C3B | 105.3 (2) |
N1C—C5C—H5CA | 110.2 (17) | C1B—N1B—C5B | 125.1 (3) |
N1C—C5C—H5CB | 107.7 (17) | C3B—N1B—C5B | 129.4 (2) |
N1C—C5C—C6C | 114.2 (3) | C1B—N2B—C2B | 106.5 (2) |
H5CA—C5C—H5CB | 106 (2) | O1B—N3B—C3B | 116.6 (3) |
C6C—C5C—H5CA | 109.3 (17) | O2B—N3B—O1B | 123.7 (3) |
C6C—C5C—H5CB | 108.8 (17) | O2B—N3B—C3B | 119.7 (3) |
O3C—C6C—C5C | 108.4 (2) | N1B—C1B—C4B | 125.4 (3) |
O3C—C6C—H6CA | 109.5 (19) | N2B—C1B—N1B | 111.1 (2) |
O3C—C6C—H6CB | 108.9 (17) | N2B—C1B—C4B | 123.6 (3) |
C5C—C6C—H6CA | 110.9 (19) | N2B—C2B—H2B | 124.3 (17) |
C5C—C6C—H6CB | 108.6 (17) | C3B—C2B—N2B | 108.8 (3) |
H6CA—C6C—H6CB | 110 (2) | C3B—C2B—H2B | 126.8 (17) |
O3C—C7C—C14C | 105.9 (12) | N1B—C3B—N3B | 124.4 (2) |
O3C—C7C—C8C | 120.0 (13) | C2B—C3B—N1B | 108.2 (2) |
O4C—C7C—O3C | 122.2 (3) | C2B—C3B—N3B | 127.3 (3) |
O4C—C7C—C14C | 131.9 (12) | C1B—C4B—H4BA | 109.5 |
O4C—C7C—C8C | 117.9 (13) | C1B—C4B—H4BB | 109.5 |
C15C—C14C—C7C | 127 (2) | C1B—C4B—H4BC | 109.5 |
C15C—C14C—C19C | 115.6 (14) | H4BA—C4B—H4BB | 109.5 |
C19C—C14C—C7C | 118 (2) | H4BA—C4B—H4BC | 109.5 |
C14C—C15C—H15C | 119.2 | H4BB—C4B—H4BC | 109.5 |
C14C—C15C—C16C | 121.7 (15) | N1B—C5B—H5BA | 108 (2) |
C16C—C15C—H15C | 119.2 | N1B—C5B—H5BB | 105.4 (18) |
C15C—C16C—H16C | 118.7 | N1B—C5B—C6B | 112.0 (3) |
C17C—C16C—C15C | 122.5 (13) | H5BA—C5B—H5BB | 111 (3) |
C17C—C16C—H16C | 118.7 | C6B—C5B—H5BA | 111 (2) |
C16C—C17C—H17C | 122.0 | C6B—C5B—H5BB | 109.9 (18) |
C16C—C17C—C18C | 115.9 (14) | O3B—C6B—C5B | 108.0 (2) |
C18C—C17C—H17C | 122.0 | O3B—C6B—H6BA | 110.0 (17) |
C17C—C18C—H18C | 119.8 | O3B—C6B—H6BB | 107.2 (18) |
C19C—C18C—C17C | 120.4 (15) | C5B—C6B—H6BA | 111.2 (17) |
C19C—C18C—H18C | 119.8 | C5B—C6B—H6BB | 110.5 (17) |
C14C—C19C—H19C | 118.2 | H6BA—C6B—H6BB | 110 (2) |
C18C—C19C—C14C | 123.6 (15) | O3B—C7B—C8B | 113.5 (2) |
C18C—C19C—H19C | 118.2 | O4B—C7B—O3B | 121.7 (3) |
C13C—C8C—C7C | 118 (3) | O4B—C7B—C8B | 124.7 (3) |
C9C—C8C—C7C | 119 (2) | C9B—C8B—C7B | 123.1 (3) |
C9C—C8C—C13C | 123.6 (17) | C9B—C8B—C13B | 119.3 (3) |
C8C—C13C—H13C | 121.2 | C13B—C8B—C7B | 117.6 (3) |
C12C—C13C—C8C | 117.7 (19) | C8B—C9B—H9B | 117.2 (19) |
C12C—C13C—H13C | 121.2 | C8B—C9B—C10B | 119.1 (4) |
C13C—C12C—H12C | 120.3 | C10B—C9B—H9B | 123.6 (19) |
C11C—C12C—C13C | 119.5 (17) | C9B—C10B—H10B | 112 (2) |
C11C—C12C—H12C | 120.3 | C11B—C10B—C9B | 120.0 (4) |
C12C—C11C—H11C | 120.3 | C11B—C10B—H10B | 127 (2) |
C12C—C11C—C10C | 119 (2) | C10B—C11B—H11B | 122 (3) |
C10C—C11C—H11C | 120.3 | C12B—C11B—C10B | 121.5 (4) |
C11C—C10C—H10C | 118.8 | C12B—C11B—H11B | 117 (3) |
C9C—C10C—C11C | 122 (2) | C11B—C12B—H12B | 124 (3) |
C9C—C10C—H10C | 118.8 | C11B—C12B—C13B | 118.2 (4) |
C8C—C9C—H9C | 121.3 | C13B—C12B—H12B | 118 (3) |
C10C—C9C—C8C | 117.4 (16) | C8B—C13B—H13B | 119 (2) |
C10C—C9C—H9C | 121.3 | C12B—C13B—C8B | 121.8 (4) |
C1A—N2A—C2A | 105.9 (2) | C12B—C13B—H13B | 119 (2) |
O1A—N3A—C3A | 117.2 (3) | C7'—O1'—H1' | 109 (2) |
O2A—N3A—O1A | 123.5 (3) | C2'—C1'—C6' | 121.5 (2) |
O2A—N3A—C3A | 119.2 (3) | C2'—C1'—C7' | 117.9 (2) |
N1A—C1A—C4A | 124.5 (2) | C6'—C1'—C7' | 120.6 (2) |
N2A—C1A—N1A | 112.1 (2) | C1'—C2'—H2' | 123.3 (16) |
N2A—C1A—C4A | 123.5 (2) | C1'—C2'—C3' | 118.9 (2) |
N2A—C2A—H2A | 124.5 (19) | C3'—C2'—H2' | 117.7 (16) |
N2A—C2A—C3A | 109.2 (3) | O3'—C3'—C2' | 117.5 (2) |
C3A—C2A—H2A | 126.3 (19) | O3'—C3'—C4' | 122.0 (2) |
N1A—C3A—N3A | 125.6 (2) | C4'—C3'—C2' | 120.5 (2) |
C2A—C3A—N1A | 108.0 (2) | C3'—C4'—H4'A | 119.7 (17) |
C2A—C3A—N3A | 126.4 (3) | C3'—C4'—C5' | 119.9 (2) |
C1A—C4A—H4AA | 113 (2) | C5'—C4'—H4'A | 120.4 (17) |
C1A—C4A—H4AB | 110 (2) | O4'—C5'—C4' | 122.1 (2) |
C1A—C4A—H4AC | 112 (3) | O4'—C5'—C6' | 117.6 (2) |
H4AA—C4A—H4AB | 104 (3) | C4'—C5'—C6' | 120.3 (2) |
H4AA—C4A—H4AC | 112 (3) | C1'—C6'—C5' | 118.9 (2) |
H4AB—C4A—H4AC | 104 (3) | C1'—C6'—H6' | 121.7 (15) |
N1A—C5A—H5AA | 107.6 (18) | C5'—C6'—H6' | 119.3 (15) |
N1A—C5A—H5AB | 105.7 (18) | O1'—C7'—C1' | 113.8 (2) |
N1A—C5A—C6A | 115.0 (3) | O2'—C7'—O1' | 122.2 (2) |
H5AA—C5A—H5AB | 114 (3) | O2'—C7'—C1' | 124.0 (2) |
Selected dihedral angles (°) of the BZMD molecule in single and multicomponent
solid forms. The θ column lists the angles between the planes defined by the
imidazole (BZMD) and phenyl/carboxylic (coformer) groups top | | φ1 | φ2 | φ3 | φ4 | φ5 | θ |
1 | BZMD | 104.1 | -63.9 | -94.9 | 178.6 | -10.6 | – |
2 | BZMDH | 100.9 | -66.4 | -178.4 | 179.5 | -6.3 | – |
3 | SLC | 111.0 | -70.2 | -170.8 | 177.4 | 7.3 | 3.8 |
4 | 3,5DBA | 110.3 | -67.7 | -169.5 | -168.7 | -11.8 | 5.7 |
5 | RES | 106.6 | -59.8 | -174.0 | -171.8 | 6.5 | 30.3 |
6 | NAF | 105.6 | -68.8 | 170.5 | 178.3 | 9.0 | 6.9 |
7 | 3,5DBA | 105.4 | -63.4 | -159.1 | 179.4 | 7.4/10.9 | 83.7 |
8 | RES | 105.1 | -71.5 | -169.1 | 175.6 | 3.7 | 31.6 |
9 | 3,5DBA | 104.0 | -63.6 | -171.5 | -178.6 | 17.8 | 89.9 |
10 | ABN | 103.6 | -62.5 | 178.6 | -179.1 | -3.1 | 13.2 |
11 | FMA | 103.3 | -70.5 | -169.6 | 175.9 | 3.8 | 22.6 |
12 | MLN | 102.9 | -61.5 | -173.2 | -172.9 | 7.5 | 22.8/29.3 |
13 | 2,6DBA | 102.4 | -73.5 | -177.2 | 178.4 | 3.4 | 5.5 |
14 | 3,5DNZ | 99.8 | -65.5 | -173.9 | -178.0 | 20.2 | 75.4 |
15 | IAC | 99.8 | -65.9 | -168.4 | 177.1 | 4.4 | 20.4 |
16 | MAC | 94.5 | -171.0 | 81.6 | 171.2 | -10.4 | 5.1 |
17 | BZC | -82.9 | -63.0 | 159.2 | -178.2 | -11.0 | 17.5 |
18 | MLC | -72.7 | -66.7 | 98.1 | 170.2 | -14.7 | 59.9 |