organic compounds
2-Chloro-N-(2-chlorobenzoyl)-N-(2-ethyl-4-oxo-3,4-dihydroquinazolin-3-yl)benzamide
aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: rbutcher99@yahoo.com
In the title compound, C24H17Cl2N3O3, the quinazolinone ring system is close to planar (r.m.s. deviation = 0.0132 Å), with the imide unit almost perpendicular to it, subtending a dihedral angle of 89.1 (1)°. However, the imide unit itself is not planar, the dihedral angle between the two O=C—N components being 34.6 (1)°. The dihedral angle between the two chlorobenzene rings is 40.50 (7)°, while the angles between these rings and the imide moiety are 54.6 (1) and 58.2 (1)°, respectively. The dihedral angles between the 2-chlorophenyl rings and the quinazolinone ring system are 48.77 (5) and 32.92 (7)° for rings A and B, respectively. In the crystal, weak C—H⋯O interactions link the molecules into a three-dimensional array.
CCDC reference: 992424
Related literature
For the synthesis and biological evaluation of some imido-substituted 1,4-naphthoquinone derivatives, see: Bakare et al. (2003); Berhe et al. (2008); Brandy et al. (2013); Khraiwesh et al. (2012). For similar X-ray structures, see: Akinboye et al. (2009a,b); Brandy et al. (2012).
Experimental
Crystal data
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Data collection: CrysAlis CCD (Agilent, 2012); cell CrysAlis RED (Agilent, 2012); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 992424
10.1107/S1600536814006035/bt6969sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814006035/bt6969Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814006035/bt6969Isup3.cml
We have been involved in the synthesis and biological evaluation of some imido-substituted 1,4-naphthoquinone derivatives (Bakare et al., 2003; Berhe et al., 2008; Brandy et al., 2013). These compounds have been shown to exhibit some anti-cancer (Bakare et al., 2003; Berhe et al., 2008) and anti-trypanosomal (Khraiwesh et al., (2012) activities. In an attempt to study the effect of replacing the naphthoquinone scaffold with quinazolinone, on biological activities of this class of compounds, we have synthesized and structurally characterized some imido-substituted quinazolinone derivatives (Akinboye et al., 2009a, 2009b). We here report the
properties of 2-chloro-N-(2-chloro-benzoyl)-N-(2-ethyl-4-oxo-4H-quinazolin-3-yl)-benzamide. Weak C—H···O interactions link the molecules into a 3-D array.In the title compound, C24H17Cl2N3O3, the quinazolinone ring is planar with the imide moiety (O1A C1A N C1B O1B) almost perpendicular with a dihedral angle of 89.1 (1)°. However, the imide moiety itself is not strictly planar. The dihedral angle between the two components (O1A C1A N and O1B C1B N) is 34.6 (1)°. The dihedral angle between the two 2-chlorophenyl rings is 40.50 (7)° while the angles between these and the imide moiety are 54.6 (1)° and 58.2 (1)° for rings A and B respectively. The dihedral angles between the 2-chlorophenyl rings and the quinazolinone ring are 48.77 (5)° and 32.92 (7)° for A and B respectively. Weak C—H···O interactions link the molecules into a 3-D array.
For the synthesis and biological evaluation of some imido-substituted 1,4-naphthoquinone derivatives, see; Bakare et al. (2003); Berhe et al. (2008); Brandy et al. (2013); Khraiwesh et al. (2012). For similar x-ray structures see Akinboye et al. (2009a, 2009b); Brandy et al. (2012).
To a solution of 3-amino-2-ethyl-4(3H) quinazolinone (186 mg) in tetrahydrofuran (15 mL) was added NaH (70.7 mg) and the mixture stirred at room temperature for 15 min. 2-Chloro-benzoyl chloride (0.273 mL) was added drop wise and the resulting mixture stirred at room temperature for 20 hr. The reaction mixture was poured into a mixture of ice (10 g) and water (10 mL) and then extracted with dichloromethane (25 mL). The organic layer was washed with water (3X20 mL), saturated sodium chloride solution (20 mL), dried over anhydrous MgSO4 and the solvent removed in vacuo to give a white solid. The crude white solid was dissolved in hot ethanol:water mixture (2:3, 5 mL) from which the title compound crystallized at room temperature after 6 days.
Data collection: CrysAlis CCD (Agilent, 2012); cell
CrysAlis RED (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C24H17Cl2N3O3 | F(000) = 1920 |
Mr = 466.31 | Dx = 1.397 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 4113 reflections |
a = 17.2597 (6) Å | θ = 4.6–32.5° |
b = 13.5463 (4) Å | µ = 0.33 mm−1 |
c = 18.9683 (7) Å | T = 200 K |
V = 4434.9 (3) Å3 | Needle, colourless |
Z = 8 | 0.52 × 0.18 × 0.15 mm |
Oxford Diffraction Gemini diffractometer | 7466 independent reflections |
Radiation source: fine-focus sealed tube | 2351 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.123 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.6°, θmin = 4.6° |
ϕ and ω scans | h = −26→25 |
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012) | k = −19→20 |
Tmin = 0.935, Tmax = 1.000 | l = −25→28 |
32371 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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 0.77 | w = 1/[σ2(Fo2) + (0.0239P)2] where P = (Fo2 + 2Fc2)/3 |
7466 reflections | (Δ/σ)max = 0.001 |
290 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C24H17Cl2N3O3 | V = 4434.9 (3) Å3 |
Mr = 466.31 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 17.2597 (6) Å | µ = 0.33 mm−1 |
b = 13.5463 (4) Å | T = 200 K |
c = 18.9683 (7) Å | 0.52 × 0.18 × 0.15 mm |
Oxford Diffraction Gemini diffractometer | 7466 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012) | 2351 reflections with I > 2σ(I) |
Tmin = 0.935, Tmax = 1.000 | Rint = 0.123 |
32371 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 0.77 | Δρmax = 0.21 e Å−3 |
7466 reflections | Δρmin = −0.24 e Å−3 |
290 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
Cl1A | 0.17309 (3) | 0.55900 (4) | 0.16919 (3) | 0.04342 (14) | |
Cl1B | 0.46697 (3) | 0.43992 (4) | 0.37319 (3) | 0.05512 (17) | |
O | 0.18853 (8) | 0.70694 (9) | 0.40899 (7) | 0.0423 (4) | |
O1A | 0.12604 (7) | 0.51488 (9) | 0.32178 (7) | 0.0417 (4) | |
O1B | 0.33657 (7) | 0.55297 (10) | 0.46096 (7) | 0.0433 (3) | |
N | 0.23311 (8) | 0.52344 (9) | 0.39013 (7) | 0.0249 (4) | |
N1 | 0.18318 (8) | 0.54745 (10) | 0.44570 (7) | 0.0265 (3) | |
N2 | 0.10350 (9) | 0.49031 (11) | 0.53679 (8) | 0.0328 (4) | |
C1 | 0.15976 (11) | 0.64646 (14) | 0.44890 (10) | 0.0297 (5) | |
C2 | 0.10246 (10) | 0.66490 (14) | 0.50310 (10) | 0.0315 (5) | |
C3 | 0.07421 (12) | 0.76030 (15) | 0.51353 (11) | 0.0447 (6) | |
H3A | 0.0929 | 0.8133 | 0.4854 | 0.054* | |
C4 | 0.01927 (13) | 0.77749 (17) | 0.56451 (12) | 0.0550 (7) | |
H4A | 0.0000 | 0.8424 | 0.5719 | 0.066* | |
C5 | −0.00805 (12) | 0.69966 (18) | 0.60521 (12) | 0.0516 (6) | |
H5A | −0.0460 | 0.7118 | 0.6404 | 0.062* | |
C6 | 0.01906 (11) | 0.60552 (16) | 0.59530 (10) | 0.0415 (5) | |
H6A | −0.0004 | 0.5531 | 0.6234 | 0.050* | |
C7 | 0.07533 (10) | 0.58646 (14) | 0.54378 (10) | 0.0311 (5) | |
C8 | 0.15506 (10) | 0.47290 (12) | 0.48974 (10) | 0.0283 (5) | |
C9 | 0.18893 (12) | 0.37229 (12) | 0.47998 (10) | 0.0376 (5) | |
H9A | 0.2461 | 0.3775 | 0.4800 | 0.045* | |
H9B | 0.1729 | 0.3463 | 0.4334 | 0.045* | |
C10 | 0.16416 (13) | 0.29949 (14) | 0.53710 (10) | 0.0543 (6) | |
H10A | 0.1871 | 0.2347 | 0.5275 | 0.081* | |
H10B | 0.1076 | 0.2938 | 0.5374 | 0.081* | |
H10C | 0.1819 | 0.3232 | 0.5831 | 0.081* | |
C1A | 0.19483 (11) | 0.49986 (12) | 0.32637 (10) | 0.0269 (4) | |
C2A | 0.24009 (10) | 0.44610 (13) | 0.27213 (9) | 0.0248 (4) | |
C3A | 0.22865 (10) | 0.46128 (13) | 0.20026 (10) | 0.0295 (4) | |
C4A | 0.26354 (11) | 0.40133 (13) | 0.15073 (10) | 0.0359 (5) | |
H4AA | 0.2551 | 0.4123 | 0.1019 | 0.043* | |
C5A | 0.31076 (12) | 0.32527 (13) | 0.17292 (11) | 0.0401 (5) | |
H5AA | 0.3342 | 0.2831 | 0.1391 | 0.048* | |
C6A | 0.32422 (11) | 0.30990 (13) | 0.24376 (11) | 0.0372 (5) | |
H6AA | 0.3577 | 0.2583 | 0.2586 | 0.045* | |
C7A | 0.28880 (10) | 0.36974 (13) | 0.29274 (10) | 0.0304 (5) | |
H7AA | 0.2978 | 0.3586 | 0.3415 | 0.037* | |
C1B | 0.31255 (10) | 0.54950 (13) | 0.40145 (10) | 0.0292 (4) | |
C2B | 0.35792 (10) | 0.57646 (12) | 0.33781 (9) | 0.0258 (4) | |
C3B | 0.42944 (10) | 0.53492 (13) | 0.32191 (10) | 0.0334 (5) | |
C4B | 0.47126 (11) | 0.56635 (16) | 0.26462 (11) | 0.0447 (5) | |
H4BA | 0.5197 | 0.5365 | 0.2539 | 0.054* | |
C5B | 0.44293 (12) | 0.64119 (16) | 0.22275 (11) | 0.0481 (6) | |
H5BA | 0.4719 | 0.6628 | 0.1830 | 0.058* | |
C6B | 0.37257 (12) | 0.68506 (14) | 0.23818 (11) | 0.0412 (5) | |
H6BA | 0.3535 | 0.7375 | 0.2098 | 0.049* | |
C7B | 0.33058 (11) | 0.65183 (12) | 0.29506 (10) | 0.0329 (5) | |
H7BA | 0.2818 | 0.6811 | 0.3053 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.0517 (3) | 0.0467 (3) | 0.0319 (3) | 0.0063 (3) | −0.0019 (3) | 0.0055 (2) |
Cl1B | 0.0382 (3) | 0.0594 (4) | 0.0677 (4) | 0.0131 (3) | 0.0015 (3) | 0.0122 (3) |
O | 0.0556 (9) | 0.0345 (8) | 0.0369 (9) | 0.0039 (7) | 0.0148 (8) | 0.0053 (6) |
O1A | 0.0225 (7) | 0.0719 (10) | 0.0307 (9) | 0.0020 (7) | −0.0006 (7) | −0.0031 (7) |
O1B | 0.0359 (8) | 0.0682 (9) | 0.0259 (8) | −0.0045 (7) | −0.0048 (7) | −0.0015 (7) |
N | 0.0235 (8) | 0.0331 (9) | 0.0181 (9) | 0.0008 (7) | 0.0038 (8) | −0.0038 (6) |
N1 | 0.0281 (8) | 0.0300 (9) | 0.0212 (9) | 0.0017 (8) | 0.0064 (8) | −0.0011 (7) |
N2 | 0.0319 (9) | 0.0397 (11) | 0.0267 (10) | −0.0036 (8) | 0.0064 (9) | −0.0023 (7) |
C1 | 0.0317 (11) | 0.0318 (12) | 0.0256 (12) | 0.0047 (10) | 0.0003 (10) | −0.0012 (9) |
C2 | 0.0313 (11) | 0.0389 (12) | 0.0245 (12) | 0.0057 (10) | 0.0014 (10) | −0.0037 (9) |
C3 | 0.0487 (13) | 0.0504 (15) | 0.0348 (14) | 0.0140 (12) | 0.0050 (12) | 0.0018 (10) |
C4 | 0.0586 (16) | 0.0568 (16) | 0.0495 (17) | 0.0246 (13) | 0.0052 (14) | −0.0088 (12) |
C5 | 0.0374 (13) | 0.0756 (18) | 0.0417 (15) | 0.0153 (13) | 0.0119 (12) | −0.0125 (13) |
C6 | 0.0328 (12) | 0.0632 (15) | 0.0286 (13) | −0.0028 (11) | 0.0113 (11) | −0.0032 (10) |
C7 | 0.0254 (10) | 0.0432 (13) | 0.0247 (12) | −0.0008 (10) | −0.0017 (10) | −0.0032 (9) |
C8 | 0.0280 (11) | 0.0349 (12) | 0.0221 (11) | −0.0034 (9) | −0.0043 (10) | −0.0001 (8) |
C9 | 0.0480 (13) | 0.0309 (12) | 0.0339 (13) | 0.0026 (10) | 0.0028 (11) | −0.0007 (9) |
C10 | 0.0830 (17) | 0.0398 (13) | 0.0401 (14) | 0.0017 (13) | 0.0111 (14) | 0.0063 (10) |
C1A | 0.0277 (10) | 0.0312 (10) | 0.0219 (11) | −0.0047 (9) | −0.0003 (10) | 0.0020 (8) |
C2A | 0.0234 (9) | 0.0266 (10) | 0.0244 (11) | −0.0064 (9) | 0.0018 (9) | −0.0043 (8) |
C3A | 0.0286 (10) | 0.0283 (11) | 0.0315 (12) | −0.0050 (9) | 0.0016 (10) | −0.0017 (8) |
C4A | 0.0502 (13) | 0.0324 (12) | 0.0252 (12) | −0.0064 (11) | 0.0074 (11) | −0.0006 (9) |
C5A | 0.0513 (13) | 0.0322 (12) | 0.0368 (14) | −0.0057 (11) | 0.0184 (12) | −0.0101 (9) |
C6A | 0.0400 (12) | 0.0281 (11) | 0.0434 (14) | 0.0032 (10) | 0.0061 (12) | −0.0030 (10) |
C7A | 0.0319 (11) | 0.0320 (12) | 0.0273 (12) | −0.0056 (10) | 0.0032 (10) | −0.0012 (9) |
C1B | 0.0260 (10) | 0.0317 (11) | 0.0298 (12) | 0.0034 (9) | −0.0023 (10) | −0.0033 (9) |
C2B | 0.0219 (9) | 0.0336 (11) | 0.0219 (11) | −0.0045 (9) | 0.0013 (9) | −0.0040 (8) |
C3B | 0.0257 (10) | 0.0394 (12) | 0.0351 (13) | −0.0002 (9) | −0.0009 (10) | −0.0004 (9) |
C4B | 0.0265 (11) | 0.0655 (15) | 0.0421 (14) | 0.0007 (12) | 0.0049 (11) | −0.0075 (12) |
C5B | 0.0379 (13) | 0.0743 (17) | 0.0321 (14) | −0.0111 (13) | 0.0111 (12) | 0.0042 (12) |
C6B | 0.0411 (12) | 0.0477 (13) | 0.0346 (14) | −0.0070 (11) | 0.0010 (12) | 0.0054 (10) |
C7B | 0.0282 (10) | 0.0385 (12) | 0.0321 (12) | −0.0023 (10) | −0.0009 (10) | −0.0059 (9) |
Cl1A—C3A | 1.7376 (18) | C9—H9B | 0.9900 |
Cl1B—C3B | 1.7385 (19) | C10—H10A | 0.9800 |
O—C1 | 1.2211 (19) | C10—H10B | 0.9800 |
O1A—C1A | 1.208 (2) | C10—H10C | 0.9800 |
O1B—C1B | 1.2034 (19) | C1A—C2A | 1.483 (2) |
N—N1 | 1.3999 (17) | C2A—C7A | 1.389 (2) |
N—C1A | 1.415 (2) | C2A—C3A | 1.393 (2) |
N—C1B | 1.432 (2) | C3A—C4A | 1.380 (2) |
N1—C8 | 1.398 (2) | C4A—C5A | 1.379 (2) |
N1—C1 | 1.402 (2) | C4A—H4AA | 0.9500 |
N2—C8 | 1.282 (2) | C5A—C6A | 1.379 (3) |
N2—C7 | 1.397 (2) | C5A—H5AA | 0.9500 |
C1—C2 | 1.448 (2) | C6A—C7A | 1.376 (2) |
C2—C7 | 1.394 (2) | C6A—H6AA | 0.9500 |
C2—C3 | 1.395 (2) | C7A—H7AA | 0.9500 |
C3—C4 | 1.374 (3) | C1B—C2B | 1.485 (2) |
C3—H3A | 0.9500 | C2B—C7B | 1.387 (2) |
C4—C5 | 1.389 (3) | C2B—C3B | 1.390 (2) |
C4—H4A | 0.9500 | C3B—C4B | 1.372 (2) |
C5—C6 | 1.371 (3) | C4B—C5B | 1.378 (3) |
C5—H5A | 0.9500 | C4B—H4BA | 0.9500 |
C6—C7 | 1.402 (2) | C5B—C6B | 1.383 (3) |
C6—H6A | 0.9500 | C5B—H5BA | 0.9500 |
C8—C9 | 1.494 (2) | C6B—C7B | 1.376 (2) |
C9—C10 | 1.526 (2) | C6B—H6BA | 0.9500 |
C9—H9A | 0.9900 | C7B—H7BA | 0.9500 |
N1—N—C1A | 114.12 (13) | O1A—C1A—N | 118.87 (17) |
N1—N—C1B | 114.78 (13) | O1A—C1A—C2A | 123.41 (18) |
C1A—N—C1B | 129.13 (15) | N—C1A—C2A | 117.25 (15) |
C8—N1—N | 119.73 (14) | C7A—C2A—C3A | 118.12 (16) |
C8—N1—C1 | 124.42 (15) | C7A—C2A—C1A | 119.29 (16) |
N—N1—C1 | 115.61 (13) | C3A—C2A—C1A | 122.13 (17) |
C8—N2—C7 | 118.64 (16) | C4A—C3A—C2A | 121.17 (17) |
O—C1—N1 | 119.86 (17) | C4A—C3A—Cl1A | 117.27 (15) |
O—C1—C2 | 127.02 (17) | C2A—C3A—Cl1A | 121.51 (14) |
N1—C1—C2 | 113.11 (16) | C5A—C4A—C3A | 119.31 (18) |
C7—C2—C3 | 120.68 (18) | C5A—C4A—H4AA | 120.3 |
C7—C2—C1 | 119.39 (17) | C3A—C4A—H4AA | 120.3 |
C3—C2—C1 | 119.93 (18) | C6A—C5A—C4A | 120.63 (18) |
C4—C3—C2 | 119.8 (2) | C6A—C5A—H5AA | 119.7 |
C4—C3—H3A | 120.1 | C4A—C5A—H5AA | 119.7 |
C2—C3—H3A | 120.1 | C7A—C6A—C5A | 119.60 (18) |
C3—C4—C5 | 119.8 (2) | C7A—C6A—H6AA | 120.2 |
C3—C4—H4A | 120.1 | C5A—C6A—H6AA | 120.2 |
C5—C4—H4A | 120.1 | C6A—C7A—C2A | 121.16 (18) |
C6—C5—C4 | 120.9 (2) | C6A—C7A—H7AA | 119.4 |
C6—C5—H5A | 119.5 | C2A—C7A—H7AA | 119.4 |
C4—C5—H5A | 119.5 | O1B—C1B—N | 118.70 (17) |
C5—C6—C7 | 120.2 (2) | O1B—C1B—C2B | 124.85 (16) |
C5—C6—H6A | 119.9 | N—C1B—C2B | 116.34 (16) |
C7—C6—H6A | 119.9 | C7B—C2B—C3B | 118.26 (17) |
C2—C7—N2 | 122.77 (17) | C7B—C2B—C1B | 118.50 (16) |
C2—C7—C6 | 118.56 (18) | C3B—C2B—C1B | 123.05 (17) |
N2—C7—C6 | 118.64 (18) | C4B—C3B—C2B | 120.90 (18) |
N2—C8—N1 | 121.61 (16) | C4B—C3B—Cl1B | 118.48 (15) |
N2—C8—C9 | 121.70 (17) | C2B—C3B—Cl1B | 120.61 (15) |
N1—C8—C9 | 116.69 (16) | C3B—C4B—C5B | 119.87 (19) |
C8—C9—C10 | 113.07 (16) | C3B—C4B—H4BA | 120.1 |
C8—C9—H9A | 109.0 | C5B—C4B—H4BA | 120.1 |
C10—C9—H9A | 109.0 | C4B—C5B—C6B | 120.4 (2) |
C8—C9—H9B | 109.0 | C4B—C5B—H5BA | 119.8 |
C10—C9—H9B | 109.0 | C6B—C5B—H5BA | 119.8 |
H9A—C9—H9B | 107.8 | C7B—C6B—C5B | 119.20 (19) |
C9—C10—H10A | 109.5 | C7B—C6B—H6BA | 120.4 |
C9—C10—H10B | 109.5 | C5B—C6B—H6BA | 120.4 |
H10A—C10—H10B | 109.5 | C6B—C7B—C2B | 121.35 (18) |
C9—C10—H10C | 109.5 | C6B—C7B—H7BA | 119.3 |
H10A—C10—H10C | 109.5 | C2B—C7B—H7BA | 119.3 |
H10B—C10—H10C | 109.5 | ||
C1A—N—N1—C8 | 88.76 (18) | C1B—N—C1A—C2A | 34.5 (2) |
C1B—N—N1—C8 | −105.67 (17) | O1A—C1A—C2A—C7A | −130.35 (19) |
C1A—N—N1—C1 | −85.93 (17) | N—C1A—C2A—C7A | 41.7 (2) |
C1B—N—N1—C1 | 79.63 (18) | O1A—C1A—C2A—C3A | 41.7 (3) |
C8—N1—C1—O | 178.75 (16) | N—C1A—C2A—C3A | −146.27 (16) |
N—N1—C1—O | −6.8 (2) | C7A—C2A—C3A—C4A | 1.1 (2) |
C8—N1—C1—C2 | −0.1 (2) | C1A—C2A—C3A—C4A | −171.08 (16) |
N—N1—C1—C2 | 174.35 (14) | C7A—C2A—C3A—Cl1A | −176.41 (12) |
O—C1—C2—C7 | 179.50 (19) | C1A—C2A—C3A—Cl1A | 11.4 (2) |
N1—C1—C2—C7 | −1.8 (2) | C2A—C3A—C4A—C5A | −0.2 (3) |
O—C1—C2—C3 | 0.3 (3) | Cl1A—C3A—C4A—C5A | 177.38 (14) |
N1—C1—C2—C3 | 179.05 (17) | C3A—C4A—C5A—C6A | −1.1 (3) |
C7—C2—C3—C4 | 0.2 (3) | C4A—C5A—C6A—C7A | 1.4 (3) |
C1—C2—C3—C4 | 179.35 (18) | C5A—C6A—C7A—C2A | −0.5 (3) |
C2—C3—C4—C5 | −0.2 (3) | C3A—C2A—C7A—C6A | −0.7 (2) |
C3—C4—C5—C6 | 0.0 (3) | C1A—C2A—C7A—C6A | 171.68 (16) |
C4—C5—C6—C7 | 0.2 (3) | N1—N—C1B—O1B | 27.8 (2) |
C3—C2—C7—N2 | −177.99 (17) | C1A—N—C1B—O1B | −169.29 (16) |
C1—C2—C7—N2 | 2.9 (3) | N1—N—C1B—C2B | −148.52 (14) |
C3—C2—C7—C6 | 0.0 (3) | C1A—N—C1B—C2B | 14.4 (2) |
C1—C2—C7—C6 | −179.09 (16) | O1B—C1B—C2B—C7B | −120.3 (2) |
C8—N2—C7—C2 | −1.9 (3) | N—C1B—C2B—C7B | 55.7 (2) |
C8—N2—C7—C6 | −179.90 (16) | O1B—C1B—C2B—C3B | 54.6 (3) |
C5—C6—C7—C2 | −0.3 (3) | N—C1B—C2B—C3B | −129.34 (18) |
C5—C6—C7—N2 | 177.84 (18) | C7B—C2B—C3B—C4B | −1.2 (3) |
C7—N2—C8—N1 | −0.1 (2) | C1B—C2B—C3B—C4B | −176.20 (17) |
C7—N2—C8—C9 | 178.94 (16) | C7B—C2B—C3B—Cl1B | −179.81 (13) |
N—N1—C8—N2 | −173.11 (15) | C1B—C2B—C3B—Cl1B | 5.2 (2) |
C1—N1—C8—N2 | 1.1 (3) | C2B—C3B—C4B—C5B | 1.1 (3) |
N—N1—C8—C9 | 7.8 (2) | Cl1B—C3B—C4B—C5B | 179.71 (15) |
C1—N1—C8—C9 | −178.03 (16) | C3B—C4B—C5B—C6B | 0.1 (3) |
N2—C8—C9—C10 | −7.8 (3) | C4B—C5B—C6B—C7B | −1.2 (3) |
N1—C8—C9—C10 | 171.29 (16) | C5B—C6B—C7B—C2B | 1.0 (3) |
N1—N—C1A—O1A | 9.9 (2) | C3B—C2B—C7B—C6B | 0.1 (3) |
C1B—N—C1A—O1A | −153.11 (17) | C1B—C2B—C7B—C6B | 175.35 (16) |
N1—N—C1A—C2A | −162.47 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7A—H7AA···Oi | 0.95 | 2.43 | 3.143 (2) | 132 |
C4B—H4BA···O1Aii | 0.95 | 2.35 | 3.211 (2) | 151 |
C6—H6A···O1Aiii | 0.95 | 2.58 | 3.377 (2) | 142 |
Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) x+1/2, y, −z+1/2; (iii) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7A—H7AA···Oi | 0.95 | 2.43 | 3.143 (2) | 131.5 |
C4B—H4BA···O1Aii | 0.95 | 2.35 | 3.211 (2) | 150.7 |
C6—H6A···O1Aiii | 0.95 | 2.58 | 3.377 (2) | 142.3 |
Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) x+1/2, y, −z+1/2; (iii) −x, −y+1, −z+1. |
Acknowledgements
RJB wishes to acknowledge the National Science Foundation MRI program (CHE0619278) for funds to purchase the diffractometer and the Howard University Nanoscience Facility for access to liquid nitrogen. This work was supported in part by grant No. 5-U54—CA914–31 (Howard University/Johns Hopkins Cancer Center Partnership), in part by grant G12MD007597 from the National Institute On Minority Health and Health Disparities of the National Institutes of Health, and in part by MRI grant No. CHE-1126533 from the NSF. We also acknowledge the Howard Hughes Medical Research Scholars program (CT).
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