organic compounds
4-(2,3-Dichlorophenyl)piperazin-1-ium picrate
aCentre for Research and Development, PRIST Deemed to be University, Thanjavur, 613 403, Tamil Nadu, India, bDepartment of Chemistry, Periyar Maniammai Institute of Science and Technology, Thanjavur 613 403, Tamil Nadu, India, cX-ray Crystallography Unit, School of Physics, University Sains Malaysia, 11800, USM, Penang, Malaysia, and dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800, USM, Penang, Malaysia
*Correspondence e-mail: nirmalramjs@gmail.com
The title compound, C6H2N3O7−·C10H13Cl2N2+, crystallizes with one 1-(2,3-dichloro-phenyl)piperazine (DP) cation and one picrate (PA) anion in the In the the DP cation and PA anion are interconnected via several N—H⋯O and C—H⋯O hydrogen bonds. The DP cation and PA anion are further connected through C—Cl⋯π [3.8201 (4), 3.7785 (4) Å] and N—O⋯π [3.7814 (4) Å] interactions. The DP cations are further interconnected via a weak intermolecular Cl⋯Cl [3.2613 (4) Å] halogen–halogen interaction. The combination of these supramolecular interactions leads to a herringbone like supramolecular architecture.
Keywords: 1-(2,3-dichlorophenyl)piperazinium picrate; crystal structure; supramolecular interaction.
CCDC reference: 2076126
Structure description
1-(2,3-Dichlorophenyl)piperazine (DP), a precursor in the synthesis of potent drugs such as aripiperazole (AP) (Oshiro et al., 1998), is used as an antipsychotic drug for the treatment of schizophrenia (Braun et al., 2009; Frank et al., 2007). A survey of the Cambridge Structural Database (CSD version 5.40, updates of May 2019; Groom et al., 2016) shows that there are no reports of salt and forms of this compound. We herein report the of a new solid form of DP, 1-(2,3-dichloro-phenyl)-piperazinium picrate (1).
The title salt, 1, crystallizes in the monoclinic P21/n The contains one (DP) cation and one picrate (PA) anion as shown in Fig. 1. In 1, the pyrazine ring of the cation molecule adopts a chair conformation with N—H and C—H bonds in axial–axial and equatorial–equatorial positions (Singh et al., 2015; Maia et al., 2012).
The protonated DP cation interacts with the neighbouring deprotonated PA anions via N1—H1A⋯O4i, N1—H1B⋯O2ii and N1—H1B⋯O7ii hydrogen bonds and C2—H2B⋯O3, C5—H5A⋯O7ii, C10—H10⋯O5iii and C17—H17⋯O1iv hydrogen bonds (Table 1). The crystal packing is shown in Fig. 2. Each DP cation is surrounded by four PA anions. The combination of N1—H1B⋯O7, N1—H1B⋯O2 and C5—H5A⋯O7 interactions between the ions leads to the formation of six-membered rings with graph-set notation R12(6) and R21(6) (Bernstein et al., 1995; Motherwell et al., 2000). Atom H1B of the amino group (N1) acts as a bifurcated donor to the O atoms of the deprotonated O1 carbonyl and O2 nitro groups of the PA anion. Inversion-related cation–anion pairs are also linked through N1—H1A⋯O4, N1—H1B⋯O2 and C17—H17⋯O1 hydrogen bonds, forming an R23(11) ring motif. Adjacent DP cations and PA anions are further connected through C8—Cl1⋯π (phenyl ring of PA anion), C9—H9⋯ π (phenyl ring of DP cation) and N5—O2⋯π (phenyl ring of DP cation) interactions [C—Cl⋯Cg1, C—Cl⋯Cg3v and N—O⋯Cg3; symmetry codes: (v) 1 − x, 2 − y, 1 − z] with C⋯π distances of 3.8201 (4) and 3.7785 (4) Å, and N⋯π = 3.782 (2) Å, with C—Cl⋯π angles of 74.15 (7) and 76.91 (7)° and an N—O⋯π angle of 68.80 (12)°. The combination of N—H⋯O and C—H⋯O hydrogen bonds and C—Cl⋯π and N—O⋯π interactions leads to the formation of a three-dimensional supramolecular herringbone architecture, which propagates along the a- and c-axis directions (Fig. 3). Additionally, the DP cations are also connected through weak intermolecular halogen–halogen Cl1⋯Cl1(7 − x, 2 − y, -z) interactions [3.2613 (4) Å] (Fig. 4).
Synthesis and crystallization
1-(2,3-Dichlorophenyl)piperazine (DP) (0.0577 mg, 0.25 mmol) and picric acid (PA) (0.05727 mg, 0.25 mmol) were dissolved independently in water and ethanol. The reactants were then mixed together in a 100 ml beaker and heated over a water bath at 90°C for 1 h (Fig. 5). The clear reaction mixture was then left aside for crystallization at room temperature. After a few days, yellow-coloured plate-like crystals formed were separated out form the mother solution.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
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Structural data
CCDC reference: 2076126
https://doi.org/10.1107/S2414314621003795/bv4037sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621003795/bv4037Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314621003795/bv4037Isup3.cml
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2020), Mercury (Macrae et al., 2020), POVRay (Cason, 2004); software used to prepare material for publication: PLATON (Spek, 2020) and publCIF (Westrip,2010).C10H13Cl2N2+·C6H2N3O7− | F(000) = 944 |
Mr = 460.23 | Dx = 1.602 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9855 (9) Å | Cell parameters from 5581 reflections |
b = 13.5742 (15) Å | θ = 1.9–30.0° |
c = 17.6103 (19) Å | µ = 0.39 mm−1 |
β = 91.463 (4)° | T = 293 K |
V = 1908.3 (4) Å3 | Plate, yellow |
Z = 4 | 0.40 × 0.35 × 0.20 mm |
Bruker APEXII CCD diffractometer | 3798 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.060 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | θmax = 30.0°, θmin = 1.9° |
h = −11→11 | |
72319 measured reflections | k = −19→19 |
5581 independent reflections | l = −24→24 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0739P)2 + 0.6029P] where P = (Fo2 + 2Fc2)/3 |
5581 reflections | (Δ/σ)max < 0.001 |
271 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.86754 (7) | 0.90877 (4) | 0.49364 (3) | 0.05570 (16) | |
Cl2 | 0.55596 (9) | 0.87130 (5) | 0.38716 (3) | 0.06593 (19) | |
O1 | 0.42341 (18) | 0.61036 (13) | 0.47240 (9) | 0.0596 (4) | |
O3 | 1.1299 (3) | 0.66281 (15) | 0.68775 (11) | 0.0815 (6) | |
O4 | 1.1043 (2) | 0.50943 (13) | 0.66777 (11) | 0.0737 (5) | |
O6 | 0.8856 (2) | 0.70824 (13) | 0.33400 (8) | 0.0620 (4) | |
O7 | 0.73482 (19) | 0.56905 (14) | 0.66344 (8) | 0.0607 (4) | |
N1 | 1.0258 (2) | 0.97533 (15) | 0.77447 (10) | 0.0557 (5) | |
H1A | 1.129102 | 0.979276 | 0.794458 | 0.067* | |
H1B | 0.958093 | 1.009367 | 0.804070 | 0.067* | |
N4 | 0.8056 (2) | 0.90163 (12) | 0.65808 (9) | 0.0448 (4) | |
N5 | 0.5018 (2) | 0.60547 (13) | 0.53316 (10) | 0.0464 (4) | |
N6 | 1.0712 (2) | 0.59397 (13) | 0.65270 (9) | 0.0449 (4) | |
N7 | 0.9808 (2) | 0.70084 (14) | 0.38929 (9) | 0.0491 (4) | |
C2 | 0.9720 (3) | 0.8704 (2) | 0.77267 (13) | 0.0631 (6) | |
H2A | 0.968767 | 0.844980 | 0.824094 | 0.076* | |
H2B | 1.052353 | 0.831680 | 0.744979 | 0.076* | |
C3 | 0.8019 (3) | 0.86087 (18) | 0.73514 (12) | 0.0565 (5) | |
H3A | 0.769483 | 0.792039 | 0.732931 | 0.068* | |
H3B | 0.719974 | 0.896037 | 0.764531 | 0.068* | |
C5 | 0.8499 (3) | 1.00694 (15) | 0.66127 (11) | 0.0462 (4) | |
H5A | 0.768611 | 1.042218 | 0.690919 | 0.055* | |
H5B | 0.847524 | 1.034217 | 0.610346 | 0.055* | |
C6 | 1.0229 (3) | 1.01986 (18) | 0.69695 (12) | 0.0534 (5) | |
H6A | 1.105461 | 0.987896 | 0.665858 | 0.064* | |
H6B | 1.050319 | 1.089372 | 0.700291 | 0.064* | |
C7 | 0.6619 (3) | 0.88178 (14) | 0.61170 (11) | 0.0428 (4) | |
C8 | 0.6754 (2) | 0.88572 (14) | 0.53246 (11) | 0.0421 (4) | |
C9 | 0.5373 (3) | 0.86809 (15) | 0.48480 (12) | 0.0482 (5) | |
C10 | 0.3843 (3) | 0.84451 (17) | 0.51519 (15) | 0.0582 (6) | |
H10 | 0.291238 | 0.833430 | 0.483512 | 0.070* | |
C11 | 0.3714 (3) | 0.83768 (19) | 0.59227 (16) | 0.0627 (6) | |
H11 | 0.269194 | 0.820331 | 0.612601 | 0.075* | |
C12 | 0.5069 (3) | 0.85596 (18) | 0.64071 (14) | 0.0574 (6) | |
H12 | 0.494641 | 0.851030 | 0.692952 | 0.069* | |
C13 | 0.7830 (2) | 0.59718 (14) | 0.59988 (11) | 0.0408 (4) | |
C14 | 0.6823 (2) | 0.61733 (14) | 0.53291 (11) | 0.0393 (4) | |
C15 | 0.7479 (2) | 0.64827 (14) | 0.46521 (11) | 0.0399 (4) | |
H15 | 0.677360 | 0.659033 | 0.423206 | 0.048* | |
C16 | 0.9173 (2) | 0.66320 (14) | 0.45975 (10) | 0.0406 (4) | |
C17 | 1.0258 (2) | 0.64607 (15) | 0.52161 (11) | 0.0425 (4) | |
H17 | 1.140531 | 0.656262 | 0.518004 | 0.051* | |
C18 | 0.9590 (2) | 0.61409 (14) | 0.58717 (11) | 0.0398 (4) | |
O2 | 0.43209 (19) | 0.59195 (15) | 0.59333 (10) | 0.0695 (5) | |
O5 | 1.1286 (2) | 0.72559 (16) | 0.38803 (9) | 0.0718 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0499 (3) | 0.0718 (4) | 0.0456 (3) | −0.0124 (2) | 0.0050 (2) | −0.0060 (2) |
Cl2 | 0.0769 (4) | 0.0705 (4) | 0.0493 (3) | −0.0001 (3) | −0.0201 (3) | −0.0011 (3) |
O1 | 0.0332 (7) | 0.0855 (12) | 0.0594 (9) | −0.0006 (7) | −0.0084 (7) | 0.0115 (8) |
O3 | 0.0942 (14) | 0.0746 (12) | 0.0738 (12) | −0.0009 (10) | −0.0364 (11) | −0.0154 (10) |
O4 | 0.0748 (12) | 0.0611 (11) | 0.0835 (12) | 0.0018 (9) | −0.0331 (10) | 0.0162 (9) |
O6 | 0.0556 (9) | 0.0880 (12) | 0.0424 (8) | 0.0026 (8) | −0.0011 (7) | 0.0138 (8) |
O7 | 0.0418 (8) | 0.0957 (12) | 0.0445 (8) | −0.0086 (8) | 0.0000 (6) | 0.0179 (8) |
N1 | 0.0409 (9) | 0.0817 (13) | 0.0441 (9) | 0.0083 (9) | −0.0063 (7) | −0.0172 (9) |
N4 | 0.0456 (9) | 0.0503 (9) | 0.0384 (8) | −0.0041 (7) | −0.0035 (7) | −0.0005 (7) |
N5 | 0.0334 (8) | 0.0518 (10) | 0.0538 (10) | 0.0049 (7) | 0.0004 (7) | 0.0101 (7) |
N6 | 0.0357 (8) | 0.0566 (11) | 0.0423 (8) | −0.0009 (7) | −0.0037 (6) | 0.0030 (7) |
N7 | 0.0441 (9) | 0.0610 (11) | 0.0424 (9) | −0.0009 (8) | 0.0037 (7) | 0.0038 (7) |
C2 | 0.0720 (16) | 0.0737 (16) | 0.0431 (11) | 0.0137 (12) | −0.0103 (10) | −0.0005 (10) |
C3 | 0.0684 (14) | 0.0595 (13) | 0.0415 (10) | −0.0043 (11) | −0.0035 (10) | 0.0036 (9) |
C5 | 0.0433 (10) | 0.0526 (11) | 0.0424 (10) | −0.0050 (8) | −0.0037 (8) | −0.0040 (8) |
C6 | 0.0433 (11) | 0.0678 (14) | 0.0492 (11) | −0.0053 (10) | −0.0006 (9) | −0.0087 (10) |
C7 | 0.0431 (10) | 0.0421 (10) | 0.0432 (10) | −0.0052 (8) | −0.0017 (8) | −0.0038 (8) |
C8 | 0.0396 (10) | 0.0408 (10) | 0.0458 (10) | −0.0052 (7) | −0.0017 (8) | −0.0028 (8) |
C9 | 0.0514 (12) | 0.0402 (10) | 0.0523 (11) | 0.0003 (8) | −0.0124 (9) | −0.0028 (8) |
C10 | 0.0422 (11) | 0.0549 (13) | 0.0769 (15) | −0.0048 (9) | −0.0135 (10) | −0.0065 (11) |
C11 | 0.0454 (12) | 0.0611 (14) | 0.0819 (17) | −0.0134 (10) | 0.0058 (11) | −0.0061 (12) |
C12 | 0.0545 (13) | 0.0630 (14) | 0.0551 (12) | −0.0126 (10) | 0.0082 (10) | −0.0050 (10) |
C13 | 0.0337 (9) | 0.0480 (10) | 0.0408 (9) | −0.0015 (7) | 0.0012 (7) | 0.0036 (8) |
C14 | 0.0278 (8) | 0.0473 (10) | 0.0428 (9) | 0.0024 (7) | −0.0005 (7) | 0.0038 (8) |
C15 | 0.0348 (9) | 0.0449 (10) | 0.0397 (9) | 0.0026 (7) | −0.0044 (7) | 0.0028 (7) |
C16 | 0.0356 (9) | 0.0483 (10) | 0.0380 (9) | −0.0005 (7) | 0.0019 (7) | 0.0035 (7) |
C17 | 0.0300 (9) | 0.0522 (11) | 0.0453 (10) | −0.0007 (7) | 0.0002 (7) | 0.0016 (8) |
C18 | 0.0311 (9) | 0.0497 (10) | 0.0383 (9) | 0.0009 (7) | −0.0052 (7) | 0.0021 (7) |
O2 | 0.0348 (7) | 0.1106 (15) | 0.0634 (10) | 0.0098 (8) | 0.0102 (7) | 0.0282 (9) |
O5 | 0.0486 (9) | 0.1141 (15) | 0.0533 (9) | −0.0199 (9) | 0.0101 (7) | 0.0089 (9) |
Cl1—C8 | 1.724 (2) | C3—H3B | 0.9700 |
Cl2—C9 | 1.730 (2) | C5—C6 | 1.513 (3) |
O1—N5 | 1.227 (2) | C5—H5A | 0.9700 |
O3—N6 | 1.208 (2) | C5—H5B | 0.9700 |
O4—N6 | 1.206 (2) | C6—H6A | 0.9700 |
O6—N7 | 1.224 (2) | C6—H6B | 0.9700 |
O7—C13 | 1.252 (2) | C7—C12 | 1.396 (3) |
N1—C2 | 1.488 (3) | C7—C8 | 1.403 (3) |
N1—C6 | 1.493 (3) | C8—C9 | 1.389 (3) |
N1—H1A | 0.8900 | C9—C10 | 1.384 (3) |
N1—H1B | 0.8900 | C10—C11 | 1.367 (4) |
N4—C7 | 1.417 (3) | C10—H10 | 0.9300 |
N4—C3 | 1.467 (3) | C11—C12 | 1.383 (3) |
N4—C5 | 1.474 (3) | C11—H11 | 0.9300 |
N5—O2 | 1.223 (2) | C12—H12 | 0.9300 |
N5—C14 | 1.451 (2) | C13—C14 | 1.436 (3) |
N6—C18 | 1.468 (2) | C13—C18 | 1.447 (3) |
N7—O5 | 1.228 (2) | C14—C15 | 1.380 (3) |
N7—C16 | 1.445 (2) | C15—C16 | 1.373 (3) |
C2—C3 | 1.501 (3) | C15—H15 | 0.9300 |
C2—H2A | 0.9700 | C16—C17 | 1.394 (3) |
C2—H2B | 0.9700 | C17—C18 | 1.356 (3) |
C3—H3A | 0.9700 | C17—H17 | 0.9300 |
C2—N1—C6 | 111.74 (17) | N1—C6—H6B | 109.9 |
C2—N1—H1A | 109.3 | C5—C6—H6B | 109.9 |
C6—N1—H1A | 109.3 | H6A—C6—H6B | 108.3 |
C2—N1—H1B | 109.3 | C12—C7—C8 | 117.72 (19) |
C6—N1—H1B | 109.3 | C12—C7—N4 | 123.32 (19) |
H1A—N1—H1B | 107.9 | C8—C7—N4 | 118.95 (17) |
C7—N4—C3 | 115.25 (17) | C9—C8—C7 | 120.93 (19) |
C7—N4—C5 | 113.38 (16) | C9—C8—Cl1 | 119.49 (16) |
C3—N4—C5 | 109.94 (16) | C7—C8—Cl1 | 119.54 (15) |
O2—N5—O1 | 122.01 (17) | C10—C9—C8 | 120.1 (2) |
O2—N5—C14 | 119.57 (17) | C10—C9—Cl2 | 119.29 (17) |
O1—N5—C14 | 118.42 (17) | C8—C9—Cl2 | 120.59 (17) |
O4—N6—O3 | 122.95 (19) | C11—C10—C9 | 119.3 (2) |
O4—N6—C18 | 118.42 (17) | C11—C10—H10 | 120.4 |
O3—N6—C18 | 118.60 (18) | C9—C10—H10 | 120.4 |
O6—N7—O5 | 122.73 (17) | C10—C11—C12 | 121.5 (2) |
O6—N7—C16 | 119.20 (17) | C10—C11—H11 | 119.2 |
O5—N7—C16 | 118.06 (17) | C12—C11—H11 | 119.2 |
N1—C2—C3 | 110.43 (19) | C11—C12—C7 | 120.4 (2) |
N1—C2—H2A | 109.6 | C11—C12—H12 | 119.8 |
C3—C2—H2A | 109.6 | C7—C12—H12 | 119.8 |
N1—C2—H2B | 109.6 | O7—C13—C14 | 127.87 (17) |
C3—C2—H2B | 109.6 | O7—C13—C18 | 120.54 (17) |
H2A—C2—H2B | 108.1 | C14—C13—C18 | 111.60 (16) |
N4—C3—C2 | 109.6 (2) | C15—C14—C13 | 123.41 (16) |
N4—C3—H3A | 109.7 | C15—C14—N5 | 115.83 (16) |
C2—C3—H3A | 109.7 | C13—C14—N5 | 120.76 (16) |
N4—C3—H3B | 109.7 | C16—C15—C14 | 120.11 (17) |
C2—C3—H3B | 109.7 | C16—C15—H15 | 119.9 |
H3A—C3—H3B | 108.2 | C14—C15—H15 | 119.9 |
N4—C5—C6 | 110.14 (17) | C15—C16—C17 | 120.96 (16) |
N4—C5—H5A | 109.6 | C15—C16—N7 | 118.66 (17) |
C6—C5—H5A | 109.6 | C17—C16—N7 | 120.34 (17) |
N4—C5—H5B | 109.6 | C18—C17—C16 | 117.94 (17) |
C6—C5—H5B | 109.6 | C18—C17—H17 | 121.0 |
H5A—C5—H5B | 108.1 | C16—C17—H17 | 121.0 |
N1—C6—C5 | 109.00 (18) | C17—C18—C13 | 125.98 (17) |
N1—C6—H6A | 109.9 | C17—C18—N6 | 118.89 (16) |
C5—C6—H6A | 109.9 | C13—C18—N6 | 115.13 (16) |
C6—N1—C2—C3 | −55.7 (2) | C18—C13—C14—C15 | 0.4 (3) |
C7—N4—C3—C2 | 169.33 (18) | O7—C13—C14—N5 | −0.3 (3) |
C5—N4—C3—C2 | −61.0 (2) | C18—C13—C14—N5 | −179.80 (17) |
N1—C2—C3—N4 | 57.7 (2) | O2—N5—C14—C15 | −169.69 (19) |
C7—N4—C5—C6 | −167.66 (17) | O1—N5—C14—C15 | 9.6 (3) |
C3—N4—C5—C6 | 61.7 (2) | O2—N5—C14—C13 | 10.5 (3) |
C2—N1—C6—C5 | 55.3 (2) | O1—N5—C14—C13 | −170.20 (18) |
N4—C5—C6—N1 | −57.9 (2) | C13—C14—C15—C16 | −1.3 (3) |
C3—N4—C7—C12 | 20.8 (3) | N5—C14—C15—C16 | 178.92 (18) |
C5—N4—C7—C12 | −107.2 (2) | C14—C15—C16—C17 | 1.0 (3) |
C3—N4—C7—C8 | −157.64 (19) | C14—C15—C16—N7 | −176.60 (18) |
C5—N4—C7—C8 | 74.4 (2) | O6—N7—C16—C15 | −7.9 (3) |
C12—C7—C8—C9 | 2.4 (3) | O5—N7—C16—C15 | 171.0 (2) |
N4—C7—C8—C9 | −179.13 (18) | O6—N7—C16—C17 | 174.48 (19) |
C12—C7—C8—Cl1 | −175.49 (17) | O5—N7—C16—C17 | −6.6 (3) |
N4—C7—C8—Cl1 | 3.0 (3) | C15—C16—C17—C18 | 0.1 (3) |
C7—C8—C9—C10 | −1.2 (3) | N7—C16—C17—C18 | 177.69 (19) |
Cl1—C8—C9—C10 | 176.69 (17) | C16—C17—C18—C13 | −1.1 (3) |
C7—C8—C9—Cl2 | −179.03 (15) | C16—C17—C18—N6 | 178.99 (17) |
Cl1—C8—C9—Cl2 | −1.2 (2) | O7—C13—C18—C17 | −178.8 (2) |
C8—C9—C10—C11 | −0.8 (3) | C14—C13—C18—C17 | 0.8 (3) |
Cl2—C9—C10—C11 | 177.11 (18) | O7—C13—C18—N6 | 1.2 (3) |
C9—C10—C11—C12 | 1.5 (4) | C14—C13—C18—N6 | −179.27 (16) |
C10—C11—C12—C7 | −0.2 (4) | O4—N6—C18—C17 | −103.0 (2) |
C8—C7—C12—C11 | −1.7 (3) | O3—N6—C18—C17 | 74.9 (3) |
N4—C7—C12—C11 | 179.9 (2) | O4—N6—C18—C13 | 77.0 (2) |
O7—C13—C14—C15 | 180.0 (2) | O3—N6—C18—C13 | −105.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O4i | 0.89 | 2.25 | 3.134 (2) | 171 |
N1—H1B···O2ii | 0.89 | 2.28 | 2.828 (3) | 119 |
N1—H1B···O7ii | 0.89 | 1.84 | 2.695 (2) | 159 |
C2—H2B···O3 | 0.97 | 2.59 | 3.444 (3) | 148 |
C5—H5A···O7ii | 0.97 | 2.59 | 3.287 (2) | 129 |
C10—H10···O5iii | 0.93 | 2.56 | 3.399 (3) | 151 |
C17—H17···O1iv | 0.93 | 2.50 | 3.348 (2) | 152 |
Symmetry codes: (i) −x+5/2, y+1/2, −z+3/2; (ii) −x+3/2, y+1/2, −z+3/2; (iii) x−1, y, z; (iv) x+1, y, z. |
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