organic compounds
3-Bromo-6-nitro-1-(prop-2-en-1-yl)-1H-indazole
aLaboratoire de Chimie Organique Hétérocyclique, Centre de Recherche des Sciences des médicaments, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: jalilmostafa202@gmail.com
The 10H8BrN3O2, contains two independent molecules differing primarily in the orientations of the allyl substituents [N—C—C=C torsion angles = −125.4 (16) and 116.0 (16)°]. The crystal packing involves slipped π–π stacking of indazole units, together with weak C—H⋯O and C—H⋯Br hydrogen bonds. The crystal studied was refined as a two-component twin.
of the title compound, CKeywords: crystal structure; hydrogen bond; π-stacking; indazole.
CCDC reference: 1813234
Structure description
Studies of the structure and physicochemical properties of the indazole ring have been reviewed (Abbassi et al., 2014; Li et al., 2003). As a continuation of our studies of indazole derivatives (Mohamed Abdelahi et al., 2017), we now report the synthesis and structure of the title compound (Fig. 1).
The
consists of two independent molecules differing primarily in the orientations of the allyl group. Thus, the torsion angles N2—N1—C8—C9 and N5—N4—C18—C19 are, respectively, −77.9 (15) and −71.9 (15)° while the N1—C8—C9—C10 and N4—C18—C19—C20 torsion angles are, respectively, −125.4 (16) and 116.0 (16)°.In the crystal, offset π–π stacking interactions between the N1/N2/C1/C2/C7 ring and the N4/N5/C11/C12/C17 ring at −x + , y − , −z + form dimers with a dihedral angle between the ring planes of 3.9 (8)° and a centroid–centroid distance of 3.494 (8) Å. These dimers are arranged into two sets of oblique stacks, generally along the a-axis direction, by C4—H4⋯O1 and C18—H1B⋯O4 hydrogen bonds (Table 1 and Figs. 2–4). The normals to the stacks are inclined by +/-30.0 (8)° to [100] and by 44.7 (8)° to each other. Weak C—H⋯Br interactions are also observed (Table 1).
Synthesis and crystallization
Allyl bromide (0.8 g, 5 mmol), potassium carbonate (1.24 g, 9 mmol) and a catalytic quantity of tetra-n-butylammonium iodide were added to a solution of 3-bromo-6-nitro-1H-indazole (0.6 g, 3 mmol) in tetrahydrofuran (30 ml). The mixture was stirred at room temperature for 48 h. The solution was then filtered and the solvent removed under reduced pressure. The residue was recrystallized from ethanol solution to afford the title compound as pale-orange plates (yield: 67%).
Refinement
Crystal data, data collection and structure . The model was refined as a two-component twin. The largest residual peaks in the final difference map are not in chemically reasonable positions to represent additional atoms. Possible sources may be inadequacies in the absorption corrections due to the large and difficulties in accurately measuring the dimensions of the small crystal or a small amount of `whole molecule disorder' (ca 3%) with these peaks representing alternate locations of the bromine atoms but with peaks for the remainder of those molecules too small to be located confidently.
details are summarized in Table 2Structural data
CCDC reference: 1813234
https://doi.org/10.1107/S2414314617018375/hb4194sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617018375/hb4194Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617018375/hb4194Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2414314617018375/hb4194Isup4.cml
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C10H8BrN3O2 | F(000) = 1120 |
Mr = 282.10 | Dx = 1.742 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 7.5971 (4) Å | Cell parameters from 7120 reflections |
b = 9.9501 (5) Å | θ = 3.1–72.2° |
c = 28.5690 (13) Å | µ = 5.14 mm−1 |
β = 95.086 (2)° | T = 150 K |
V = 2151.08 (18) Å3 | Plate, pale orange |
Z = 8 | 0.25 × 0.09 × 0.04 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 7639 independent reflections |
Radiation source: INCOATEC IµS micro–focus source | 7050 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.050 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.3°, θmin = 3.1° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009) | k = −12→12 |
Tmin = 0.36, Tmax = 0.82 | l = −34→34 |
7880 measured reflections |
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)] = 0.079 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.217 | H-atom parameters constrained |
S = 1.19 | w = 1/[σ2(Fo2) + (0.0535P)2 + 28.3909P] where P = (Fo2 + 2Fc2)/3 |
7639 reflections | (Δ/σ)max < 0.001 |
290 parameters | Δρmax = 1.30 e Å−3 |
0 restraints | Δρmin = −1.22 e Å−3 |
Experimental. Analysis of 329 reflections having I/σ(I) > 12 and chosen from the full data set with CELL_NOW (Sheldrick, 2008) showed the crystal to belong to the monoclinic system and to be twinned by a 180° rotation about the c* axis. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW. |
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.5670 (2) | 0.14543 (15) | 0.47380 (4) | 0.0448 (5) | |
O1 | 0.4189 (17) | 0.4609 (11) | 0.2213 (3) | 0.052 (3) | |
O2 | 0.2730 (18) | 0.2752 (12) | 0.2166 (3) | 0.061 (3) | |
N1 | 0.6482 (14) | 0.4618 (10) | 0.3968 (3) | 0.029 (3) | |
N2 | 0.6614 (15) | 0.3910 (11) | 0.4374 (3) | 0.033 (3) | |
N3 | 0.3656 (16) | 0.3548 (12) | 0.2383 (3) | 0.034 (3) | |
C1 | 0.582 (2) | 0.2767 (12) | 0.4274 (4) | 0.031 (3) | |
C2 | 0.5133 (18) | 0.2658 (12) | 0.3802 (4) | 0.026 (3) | |
C3 | 0.4215 (18) | 0.1720 (13) | 0.3514 (4) | 0.028 (3) | |
H3 | 0.391544 | 0.087488 | 0.363954 | 0.033* | |
C4 | 0.3747 (17) | 0.1995 (12) | 0.3060 (4) | 0.025 (3) | |
H4 | 0.312848 | 0.134651 | 0.286457 | 0.030* | |
C5 | 0.4187 (16) | 0.3267 (13) | 0.2873 (4) | 0.024 (3) | |
C6 | 0.5098 (16) | 0.4257 (12) | 0.3134 (4) | 0.026 (3) | |
H6 | 0.540098 | 0.509440 | 0.300322 | 0.031* | |
C7 | 0.5544 (15) | 0.3920 (12) | 0.3613 (4) | 0.022 (3) | |
C8 | 0.703 (2) | 0.6038 (13) | 0.3969 (4) | 0.036 (3) | |
H8A | 0.816224 | 0.613203 | 0.416593 | 0.043* | |
H8B | 0.724045 | 0.630139 | 0.364414 | 0.043* | |
C9 | 0.5749 (19) | 0.6947 (12) | 0.4142 (4) | 0.030 (3) | |
H9 | 0.537239 | 0.676754 | 0.444368 | 0.036* | |
C10 | 0.508 (2) | 0.7977 (14) | 0.3921 (5) | 0.044 (4) | |
H10A | 0.541706 | 0.819364 | 0.361763 | 0.053* | |
H10B | 0.424128 | 0.852263 | 0.406066 | 0.053* | |
Br2 | 0.29479 (19) | 0.94236 (14) | 0.02996 (4) | 0.0338 (4) | |
O3 | 0.7297 (14) | 0.7347 (10) | 0.2791 (3) | 0.044 (3) | |
O4 | 0.6462 (16) | 0.9375 (10) | 0.2877 (3) | 0.047 (3) | |
N4 | 0.5227 (15) | 0.6482 (11) | 0.1051 (3) | 0.032 (3) | |
N5 | 0.4444 (16) | 0.7016 (11) | 0.0653 (3) | 0.032 (3) | |
N6 | 0.6590 (16) | 0.8373 (12) | 0.2639 (3) | 0.032 (3) | |
C11 | 0.3999 (17) | 0.8278 (14) | 0.0754 (4) | 0.028 (3) | |
C12 | 0.4494 (18) | 0.8587 (13) | 0.1237 (4) | 0.030 (3) | |
C13 | 0.4325 (18) | 0.9707 (13) | 0.1528 (4) | 0.029 (3) | |
H13 | 0.374507 | 1.050083 | 0.141120 | 0.035* | |
C14 | 0.5014 (17) | 0.9617 (13) | 0.1977 (4) | 0.030 (3) | |
H14 | 0.494502 | 1.036167 | 0.218244 | 0.036* | |
C15 | 0.5842 (18) | 0.8410 (14) | 0.2143 (4) | 0.031 (3) | |
C16 | 0.5987 (18) | 0.7294 (13) | 0.1879 (4) | 0.027 (3) | |
H16 | 0.652562 | 0.649426 | 0.200420 | 0.033* | |
C17 | 0.5295 (18) | 0.7390 (12) | 0.1410 (4) | 0.026 (3) | |
C18 | 0.598 (2) | 0.5136 (13) | 0.1044 (4) | 0.035 (3) | |
H18A | 0.673729 | 0.507640 | 0.078086 | 0.042* | |
H18B | 0.673545 | 0.499252 | 0.133934 | 0.042* | |
C19 | 0.468 (2) | 0.4073 (14) | 0.0994 (5) | 0.044 (4) | |
H19 | 0.392167 | 0.395215 | 0.123703 | 0.053* | |
C20 | 0.450 (2) | 0.3270 (16) | 0.0632 (5) | 0.051 (4) | |
H20A | 0.524262 | 0.336954 | 0.038349 | 0.061* | |
H20B | 0.362454 | 0.258601 | 0.061658 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0687 (11) | 0.0364 (8) | 0.0294 (6) | 0.0046 (9) | 0.0052 (8) | 0.0051 (5) |
O1 | 0.071 (8) | 0.051 (7) | 0.033 (4) | 0.008 (6) | 0.006 (5) | 0.007 (4) |
O2 | 0.076 (9) | 0.071 (8) | 0.032 (5) | −0.014 (8) | −0.017 (6) | −0.008 (5) |
N1 | 0.038 (7) | 0.027 (6) | 0.023 (4) | −0.007 (6) | 0.004 (4) | −0.006 (4) |
N2 | 0.034 (7) | 0.037 (7) | 0.029 (5) | 0.005 (6) | 0.005 (5) | −0.001 (4) |
N3 | 0.030 (6) | 0.038 (7) | 0.033 (5) | 0.006 (7) | 0.002 (5) | 0.004 (5) |
C1 | 0.042 (8) | 0.023 (7) | 0.027 (5) | 0.009 (7) | 0.003 (6) | 0.000 (5) |
C2 | 0.021 (6) | 0.025 (6) | 0.035 (6) | 0.003 (7) | 0.014 (5) | −0.004 (5) |
C3 | 0.028 (7) | 0.017 (6) | 0.038 (6) | 0.005 (6) | 0.002 (6) | −0.002 (5) |
C4 | 0.019 (6) | 0.023 (6) | 0.032 (5) | −0.007 (6) | 0.004 (5) | −0.008 (4) |
C5 | 0.020 (7) | 0.020 (6) | 0.033 (6) | 0.002 (6) | 0.005 (5) | −0.003 (5) |
C6 | 0.019 (7) | 0.021 (6) | 0.038 (6) | 0.008 (6) | 0.003 (5) | 0.000 (5) |
C7 | 0.010 (6) | 0.027 (6) | 0.030 (5) | 0.009 (6) | 0.004 (5) | −0.006 (4) |
C8 | 0.042 (9) | 0.029 (7) | 0.035 (6) | −0.012 (7) | 0.002 (6) | −0.008 (5) |
C9 | 0.037 (8) | 0.024 (6) | 0.030 (5) | 0.005 (7) | 0.004 (6) | −0.005 (5) |
C10 | 0.041 (9) | 0.039 (9) | 0.053 (8) | 0.000 (8) | 0.005 (8) | 0.009 (6) |
Br2 | 0.0371 (7) | 0.0342 (7) | 0.0288 (5) | −0.0009 (7) | −0.0042 (6) | 0.0048 (5) |
O3 | 0.058 (7) | 0.045 (6) | 0.028 (4) | 0.022 (6) | −0.005 (5) | 0.007 (4) |
O4 | 0.070 (7) | 0.041 (6) | 0.031 (4) | −0.005 (6) | −0.001 (5) | −0.012 (4) |
N4 | 0.037 (7) | 0.030 (6) | 0.028 (5) | −0.001 (6) | −0.003 (4) | −0.001 (4) |
N5 | 0.038 (7) | 0.039 (6) | 0.020 (4) | −0.001 (6) | −0.001 (5) | −0.002 (4) |
N6 | 0.032 (7) | 0.039 (7) | 0.025 (4) | −0.001 (6) | −0.006 (5) | 0.008 (5) |
C11 | 0.022 (6) | 0.036 (8) | 0.024 (5) | −0.014 (7) | −0.003 (5) | −0.001 (5) |
C12 | 0.028 (7) | 0.030 (7) | 0.030 (5) | −0.003 (7) | 0.000 (5) | 0.006 (5) |
C13 | 0.030 (7) | 0.024 (6) | 0.033 (6) | −0.002 (7) | 0.000 (5) | 0.003 (5) |
C14 | 0.024 (7) | 0.028 (7) | 0.037 (6) | −0.012 (7) | 0.004 (5) | 0.001 (5) |
C15 | 0.037 (8) | 0.039 (8) | 0.018 (5) | −0.005 (7) | 0.002 (5) | 0.004 (5) |
C16 | 0.029 (7) | 0.026 (6) | 0.025 (5) | −0.005 (7) | 0.001 (5) | 0.008 (5) |
C17 | 0.026 (7) | 0.021 (6) | 0.030 (5) | −0.010 (6) | 0.005 (5) | −0.007 (5) |
C18 | 0.044 (9) | 0.028 (7) | 0.033 (6) | −0.003 (7) | 0.004 (6) | −0.005 (5) |
C19 | 0.050 (10) | 0.034 (8) | 0.048 (7) | 0.002 (8) | 0.002 (7) | −0.006 (6) |
C20 | 0.053 (10) | 0.041 (8) | 0.055 (8) | 0.005 (10) | −0.018 (8) | −0.014 (7) |
Br1—C1 | 1.872 (12) | Br2—C11 | 1.854 (12) |
O1—N3 | 1.244 (15) | O3—N6 | 1.216 (14) |
O2—N3 | 1.195 (15) | O4—N6 | 1.217 (14) |
N1—N2 | 1.352 (13) | N4—N5 | 1.344 (14) |
N1—C7 | 1.376 (14) | N4—C17 | 1.364 (15) |
N1—C8 | 1.472 (16) | N4—C18 | 1.456 (17) |
N2—C1 | 1.307 (16) | N5—C11 | 1.339 (17) |
N3—C5 | 1.451 (15) | N6—C15 | 1.480 (13) |
C1—C2 | 1.406 (17) | C11—C12 | 1.432 (15) |
C2—C3 | 1.391 (18) | C12—C13 | 1.402 (17) |
C2—C7 | 1.413 (17) | C12—C17 | 1.407 (18) |
C3—C4 | 1.342 (16) | C13—C14 | 1.345 (16) |
C3—H3 | 0.9500 | C13—H13 | 0.9500 |
C4—C5 | 1.424 (17) | C14—C15 | 1.418 (19) |
C4—H4 | 0.9500 | C14—H14 | 0.9500 |
C5—C6 | 1.383 (17) | C15—C16 | 1.352 (18) |
C6—C7 | 1.420 (15) | C16—C17 | 1.399 (16) |
C6—H6 | 0.9500 | C16—H16 | 0.9500 |
C8—C9 | 1.448 (19) | C18—C19 | 1.44 (2) |
C8—H8A | 0.9900 | C18—H18A | 0.9900 |
C8—H8B | 0.9900 | C18—H18B | 0.9900 |
C9—C10 | 1.285 (18) | C19—C20 | 1.304 (19) |
C9—H9 | 0.9500 | C19—H19 | 0.9500 |
C10—H10A | 0.9500 | C20—H20A | 0.9500 |
C10—H10B | 0.9500 | C20—H20B | 0.9500 |
N2—N1—C7 | 111.3 (10) | N5—N4—C17 | 111.0 (10) |
N2—N1—C8 | 120.0 (9) | N5—N4—C18 | 119.7 (9) |
C7—N1—C8 | 127.8 (10) | C17—N4—C18 | 129.1 (10) |
C1—N2—N1 | 105.6 (9) | C11—N5—N4 | 106.8 (9) |
O2—N3—O1 | 123.9 (11) | O3—N6—O4 | 122.8 (10) |
O2—N3—C5 | 118.3 (11) | O3—N6—C15 | 119.0 (11) |
O1—N3—C5 | 117.9 (11) | O4—N6—C15 | 118.2 (11) |
N2—C1—C2 | 113.6 (11) | N5—C11—C12 | 111.1 (11) |
N2—C1—Br1 | 120.6 (9) | N5—C11—Br2 | 121.8 (8) |
C2—C1—Br1 | 125.8 (10) | C12—C11—Br2 | 127.1 (10) |
C3—C2—C1 | 138.1 (12) | C13—C12—C17 | 121.7 (10) |
C3—C2—C7 | 119.1 (11) | C13—C12—C11 | 135.4 (12) |
C1—C2—C7 | 102.9 (11) | C17—C12—C11 | 102.9 (11) |
C4—C3—C2 | 120.8 (12) | C14—C13—C12 | 117.6 (12) |
C4—C3—H3 | 119.6 | C14—C13—H13 | 121.2 |
C2—C3—H3 | 119.6 | C12—C13—H13 | 121.2 |
C3—C4—C5 | 119.5 (11) | C13—C14—C15 | 119.9 (12) |
C3—C4—H4 | 120.3 | C13—C14—H14 | 120.0 |
C5—C4—H4 | 120.3 | C15—C14—H14 | 120.0 |
C6—C5—C4 | 123.7 (11) | C16—C15—C14 | 124.4 (10) |
C6—C5—N3 | 117.8 (11) | C16—C15—N6 | 118.0 (12) |
C4—C5—N3 | 118.6 (11) | C14—C15—N6 | 117.6 (11) |
C5—C6—C7 | 114.6 (11) | C15—C16—C17 | 115.8 (12) |
C5—C6—H6 | 122.7 | C15—C16—H16 | 122.1 |
C7—C6—H6 | 122.7 | C17—C16—H16 | 122.1 |
N1—C7—C2 | 106.5 (10) | N4—C17—C16 | 131.4 (12) |
N1—C7—C6 | 131.0 (11) | N4—C17—C12 | 108.1 (10) |
C2—C7—C6 | 122.5 (11) | C16—C17—C12 | 120.5 (11) |
C9—C8—N1 | 113.6 (12) | C19—C18—N4 | 114.3 (12) |
C9—C8—H8A | 108.8 | C19—C18—H18A | 108.7 |
N1—C8—H8A | 108.8 | N4—C18—H18A | 108.7 |
C9—C8—H8B | 108.8 | C19—C18—H18B | 108.7 |
N1—C8—H8B | 108.8 | N4—C18—H18B | 108.7 |
H8A—C8—H8B | 107.7 | H18A—C18—H18B | 107.6 |
C10—C9—C8 | 125.5 (13) | C20—C19—C18 | 123.5 (16) |
C10—C9—H9 | 117.2 | C20—C19—H19 | 118.3 |
C8—C9—H9 | 117.2 | C18—C19—H19 | 118.3 |
C9—C10—H10A | 120.0 | C19—C20—H20A | 120.0 |
C9—C10—H10B | 120.0 | C19—C20—H20B | 120.0 |
H10A—C10—H10B | 120.0 | H20A—C20—H20B | 120.0 |
C7—N1—N2—C1 | 1.8 (14) | C17—N4—N5—C11 | −0.1 (15) |
C8—N1—N2—C1 | 171.7 (12) | C18—N4—N5—C11 | −175.7 (12) |
N1—N2—C1—C2 | 0.3 (15) | N4—N5—C11—C12 | −0.4 (15) |
N1—N2—C1—Br1 | −179.8 (9) | N4—N5—C11—Br2 | 177.7 (9) |
N2—C1—C2—C3 | 179.7 (15) | N5—C11—C12—C13 | −178.5 (15) |
Br1—C1—C2—C3 | 0 (3) | Br2—C11—C12—C13 | 3 (2) |
N2—C1—C2—C7 | −2.0 (16) | N5—C11—C12—C17 | 0.7 (15) |
Br1—C1—C2—C7 | 178.0 (10) | Br2—C11—C12—C17 | −177.3 (10) |
C1—C2—C3—C4 | 179.1 (16) | C17—C12—C13—C14 | 2 (2) |
C7—C2—C3—C4 | 1.1 (19) | C11—C12—C13—C14 | −178.6 (14) |
C2—C3—C4—C5 | 0 (2) | C12—C13—C14—C15 | −1 (2) |
C3—C4—C5—C6 | 1 (2) | C13—C14—C15—C16 | −1 (2) |
C3—C4—C5—N3 | −179.5 (12) | C13—C14—C15—N6 | 179.5 (12) |
O2—N3—C5—C6 | −173.3 (12) | O3—N6—C15—C16 | −0.3 (18) |
O1—N3—C5—C6 | 6.5 (17) | O4—N6—C15—C16 | −180.0 (13) |
O2—N3—C5—C4 | 6.8 (18) | O3—N6—C15—C14 | 179.4 (12) |
O1—N3—C5—C4 | −173.4 (12) | O4—N6—C15—C14 | −0.2 (18) |
C4—C5—C6—C7 | −1.2 (18) | C14—C15—C16—C17 | 2 (2) |
N3—C5—C6—C7 | 178.9 (10) | N6—C15—C16—C17 | −178.6 (11) |
N2—N1—C7—C2 | −3.0 (13) | N5—N4—C17—C16 | −179.5 (14) |
C8—N1—C7—C2 | −172.0 (12) | C18—N4—C17—C16 | −4 (2) |
N2—N1—C7—C6 | −179.2 (12) | N5—N4—C17—C12 | 0.6 (15) |
C8—N1—C7—C6 | 12 (2) | C18—N4—C17—C12 | 175.6 (13) |
C3—C2—C7—N1 | −178.4 (11) | C15—C16—C17—N4 | 179.5 (13) |
C1—C2—C7—N1 | 2.9 (13) | C15—C16—C17—C12 | −1 (2) |
C3—C2—C7—C6 | −1.8 (18) | C13—C12—C17—N4 | 178.6 (12) |
C1—C2—C7—C6 | 179.5 (12) | C11—C12—C17—N4 | −0.8 (14) |
C5—C6—C7—N1 | 177.5 (12) | C13—C12—C17—C16 | −1 (2) |
C5—C6—C7—C2 | 1.8 (17) | C11—C12—C17—C16 | 179.3 (13) |
N2—N1—C8—C9 | −77.9 (15) | N5—N4—C18—C19 | −71.9 (15) |
C7—N1—C8—C9 | 90.1 (14) | C17—N4—C18—C19 | 113.4 (15) |
N1—C8—C9—C10 | −125.4 (16) | N4—C18—C19—C20 | 116.0 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O1i | 0.95 | 2.46 | 3.304 (16) | 147 |
C18—H18B···O4ii | 0.99 | 2.59 | 3.578 (16) | 174 |
C9—H9···Br1iii | 0.95 | 3.09 | 3.814 (11) | 134 |
C18—H18A···Br1iv | 0.99 | 2.91 | 3.770 (14) | 146 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x+3/2, y+1/2, −z+1/2. |
Acknowledgements
The support of NSF-MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.
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