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In the title compound, C18H17ClN2O4, the dihedral angle between the benzofuran ring system [maximum deviation 0.014 (2) Å] and the oxopyradizine ring is 73.33 (8)°. The structure is characterized by disorder of the ethyl group, which is split into two parts, with a major component of 0.57 (3), and the acetate carbonyl O atom, which is statistically disordered. In the crystal, the molecules are linked by C—H...O inter­actions, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015006301/tk5363sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989015006301/tk5363Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015006301/tk5363Isup3.cml
Supplementary material

CCDC reference: 1056731

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.044
  • wR factor = 0.114
  • Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT213_ALERT_2_B Atom C17B has ADP max/min Ratio ..... 4.4 prolat
Alert level C PLAT213_ALERT_2_C Atom C18A has ADP max/min Ratio ..... 3.1 prolat PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) Range 5.5 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Uiso(max)/Uiso(min) ... 6.0 Ratio PLAT234_ALERT_4_C Large Hirshfeld Difference C17A -- C18A .. 0.17 Ang. PLAT242_ALERT_2_C Low Ueq as Compared to Neighbors for ..... O4 Check PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.1 Note
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF Please Do ! PLAT300_ALERT_4_G Atom Site Occupancy of *O3A is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of *O3B is Constrained at 0.500 Check PLAT300_ALERT_4_G Atom Site Occupancy of >C17A is Constrained at 0.570 Check PLAT300_ALERT_4_G Atom Site Occupancy of >C18A is Constrained at 0.570 Check PLAT300_ALERT_4_G Atom Site Occupancy of <C17B is Constrained at 0.430 Check PLAT300_ALERT_4_G Atom Site Occupancy of <C18B is Constrained at 0.430 Check PLAT301_ALERT_3_G Main Residue Disorder ............ Percentage = 12 Note PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety ..... C14 Check PLAT431_ALERT_2_G Short Inter HL..A Contact Cl1 .. O2 .. 3.08 Ang. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 55 Check O3A -C16 -O3B 1.555 1.555 1.555 24.80 Deg. PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF .... # 92 Check C17A -O4 -C17B 1.555 1.555 1.555 17.90 Deg. PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 1 Report PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by . 1 Units
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 15 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 11 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

During recent years, pyridazinones have been a subject of numerous recent studies (Boukharsa et al., 2014) owing to their wide spectrum of pharmacological activities such as antimicrobial (Nagle et al., 2014), anti-fungal (El-Hashash et al., 2014), analgesic & anti-inflammatory (Tiryaki et al., 2013), anticancer (Csókás et al., 2013), anti-tubercular (Asif et al., 2014) and anti-hypertensive activities (Garkani-Nejad & Poshteh-Shirani, 2013). It has also been reported that pyridazinone derivative have remarkable insecticidal (Cao et al., 2003) and herbicidal activities (Jamet & Piedallu, 1975). In continuation of this line of research (Taoufik et al., 1984; Benchat et al., 1998; Abourichaa et al., 2003), we have developed a new pyridazin-3(2H)-one derivative. It will be subjected to further pharmacological investigations, especially tests of anticancer activity. Compound (I) is stable at room temperature, and its structure has been determined by NMR (1H and 13 C). In this paper we wish to report the crystal structure determination of the title compound possessing the biologically active pyridazinone ring.

The molecule of the title compound is build up from 5-chlorobenzofuran-2-yl linked, via –CH2– group, to six-membered heterocyclic ring which is related to acetate group as shown in Fig. 1. The benzofuran system is virtually planar with the largest deviation from the mean plane being -0.014 (2) Å at C4, and makes dihedral angle of 73.33 (8)° with the mean plane through the oxopyridazin (C10–C13,N1,N2) ring. Non classical C—H···O hydrogen bonds link the molecules into a three-dimensional network.

Related literature top

For pharmacological activities, e.g. antimicrobial, of pyridazinones, see: Boukharsa et al. (2014); Nagle et al. (2014); El-Hashash et al. (2014); Tiryaki et al. (2013); Csókás et al. (2013); Asif et al. (2014); Garkani-Nejad & Poshteh-Shirani (2013). For activities of pyridazinone derivative, e.g. as insecticides and herbicides, see: Cao et al. (2003); Jamet & Piedallu (1975). For new pyridazin-3(2H)-one derivatives, see: Taoufik et al. (1984); Benchat et al. (1998); Abourichaa et al. (2003).

Experimental top

To a solution of 5-((5-chlorobenzofuran-2-yl)methyl)-6-methylpyridazin-3(2H)-one (0.5 g, 1.82 mmol) dissolved in tetrahydrofuran (15 ml) was added ethyl 2-bromoacetate (0.30 ml, 2.73 mmol), potassium carbonate (0.5 g, 3.64 mmol) and a catalytic amount of tetra-n-butylammonium bromide (0.05 g, 0.15 mmol). The mixture was stirred at room temperature for 6 h, and monitored by thin layer chromatography. The compound was removed by filtration and the filtrate concentrated under vacuum. The solid obtained was crystallized from ethanol to afford colourless crystals (Yield = 77%; M.pt = 136.9 °C).

Refinement top

The H atoms were located in a difference map and treated as riding with C—H = 0.93 Å (aromatic), C—H = 0.97 Å (methylene) and C—H = 0.96 Å (methyl), and with Uiso(H) = 1.2 Ueq (aromatic and methylene) and Uiso(H) = 1.5 Ueq for methyl. This structure is characterized by a partial disorder at the acetate group, with the ethyl group split into two parts. The major component had a site occupancy factor = 0.57 (3). The carbonyl-O3 was statistically disordered. Owing to poor agreement, the (0 0 2) reflection was omitted from the final cycles of refinement.

Structure description top

During recent years, pyridazinones have been a subject of numerous recent studies (Boukharsa et al., 2014) owing to their wide spectrum of pharmacological activities such as antimicrobial (Nagle et al., 2014), anti-fungal (El-Hashash et al., 2014), analgesic & anti-inflammatory (Tiryaki et al., 2013), anticancer (Csókás et al., 2013), anti-tubercular (Asif et al., 2014) and anti-hypertensive activities (Garkani-Nejad & Poshteh-Shirani, 2013). It has also been reported that pyridazinone derivative have remarkable insecticidal (Cao et al., 2003) and herbicidal activities (Jamet & Piedallu, 1975). In continuation of this line of research (Taoufik et al., 1984; Benchat et al., 1998; Abourichaa et al., 2003), we have developed a new pyridazin-3(2H)-one derivative. It will be subjected to further pharmacological investigations, especially tests of anticancer activity. Compound (I) is stable at room temperature, and its structure has been determined by NMR (1H and 13 C). In this paper we wish to report the crystal structure determination of the title compound possessing the biologically active pyridazinone ring.

The molecule of the title compound is build up from 5-chlorobenzofuran-2-yl linked, via –CH2– group, to six-membered heterocyclic ring which is related to acetate group as shown in Fig. 1. The benzofuran system is virtually planar with the largest deviation from the mean plane being -0.014 (2) Å at C4, and makes dihedral angle of 73.33 (8)° with the mean plane through the oxopyridazin (C10–C13,N1,N2) ring. Non classical C—H···O hydrogen bonds link the molecules into a three-dimensional network.

For pharmacological activities, e.g. antimicrobial, of pyridazinones, see: Boukharsa et al. (2014); Nagle et al. (2014); El-Hashash et al. (2014); Tiryaki et al. (2013); Csókás et al. (2013); Asif et al. (2014); Garkani-Nejad & Poshteh-Shirani (2013). For activities of pyridazinone derivative, e.g. as insecticides and herbicides, see: Cao et al. (2003); Jamet & Piedallu (1975). For new pyridazin-3(2H)-one derivatives, see: Taoufik et al. (1984); Benchat et al. (1998); Abourichaa et al. (2003).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.
[Figure 2] Fig. 2. Crystal packing in the structure of the title compound, showing molecules linked by C—H···O hydrogen bonds (dashed lines).
Ethyl 2-{4-[(5-chloro-1-benzofuran-2-yl)methyl]-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl}acetate top
Crystal data top
C18H17ClN2O4F(000) = 752
Mr = 360.79Dx = 1.362 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: p 2ac 2abCell parameters from 4925 reflections
a = 7.9792 (2) Åθ = 2.5–29.6°
b = 8.7460 (2) ŵ = 0.24 mm1
c = 25.2064 (6) ÅT = 296 K
V = 1759.06 (7) Å3Block, colourless
Z = 40.37 × 0.34 × 0.29 mm
Data collection top
Bruker APEXII CCD
diffractometer
4925 independent reflections
Radiation source: fine-focus sealed tube3350 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω and φ scansθmax = 29.6°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 116
Tmin = 0.589, Tmax = 0.746k = 1211
12689 measured reflectionsl = 3534
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0511P)2 + 0.0996P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.043
4925 reflectionsΔρmax = 0.25 e Å3
255 parametersΔρmin = 0.34 e Å3
0 restraintsAbsolute structure: Flack & Bernardinelli (2000), 2104 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (7)
Crystal data top
C18H17ClN2O4V = 1759.06 (7) Å3
Mr = 360.79Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.9792 (2) ŵ = 0.24 mm1
b = 8.7460 (2) ÅT = 296 K
c = 25.2064 (6) Å0.37 × 0.34 × 0.29 mm
Data collection top
Bruker APEXII CCD
diffractometer
4925 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3350 reflections with I > 2σ(I)
Tmin = 0.589, Tmax = 0.746Rint = 0.031
12689 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.114Δρmax = 0.25 e Å3
S = 1.02Δρmin = 0.34 e Å3
4925 reflectionsAbsolute structure: Flack & Bernardinelli (2000), 2104 Friedel pairs
255 parametersAbsolute structure parameter: 0.02 (7)
0 restraints
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.0331 (3)0.7077 (3)0.55647 (8)0.0497 (5)
C20.0495 (3)0.7389 (3)0.50905 (9)0.0551 (6)
H20.10060.83350.50420.066*
C30.0561 (3)0.6314 (3)0.46924 (8)0.0500 (5)
H30.11010.65070.43720.060*
C40.0215 (2)0.4935 (2)0.47935 (7)0.0408 (4)
C50.1023 (2)0.4581 (2)0.52669 (7)0.0401 (5)
C60.1087 (3)0.5691 (3)0.56674 (8)0.0493 (6)
H60.16180.55000.59890.059*
C70.1597 (3)0.3032 (3)0.52045 (8)0.0448 (5)
H70.21880.24600.54530.054*
C80.1118 (3)0.2568 (3)0.47190 (8)0.0431 (5)
C90.1316 (3)0.1120 (3)0.44154 (8)0.0472 (5)
H9A0.02200.07850.42970.057*
H9B0.17550.03420.46520.057*
C100.2463 (2)0.1236 (2)0.39358 (7)0.0368 (4)
C110.3432 (2)0.2461 (2)0.38377 (7)0.0414 (4)
H110.33830.32990.40640.050*
C120.4547 (3)0.2499 (2)0.33859 (8)0.0409 (4)
C130.2541 (2)0.0037 (3)0.35783 (7)0.0384 (4)
C140.1523 (3)0.1455 (3)0.36636 (9)0.0514 (5)
H14A0.17510.21730.33850.077*
H14B0.03530.11980.36620.077*
H14C0.18120.19020.39990.077*
C150.5492 (3)0.1158 (3)0.25914 (8)0.0460 (5)
H15A0.56110.21730.24410.055*
H15B0.49500.05130.23290.055*
C160.7196 (3)0.0523 (3)0.27179 (9)0.0570 (6)
C17A0.9885 (15)0.004 (2)0.2313 (4)0.090 (4)0.57 (3)
H17A1.04390.06920.25710.108*0.57 (3)
H17B0.99390.09980.24460.108*0.57 (3)
C18A1.0731 (14)0.0109 (18)0.1866 (4)0.115 (5)0.57 (3)
H18A1.18660.02090.19270.173*0.57 (3)
H18B1.07230.11400.17350.173*0.57 (3)
H18C1.02200.05550.16090.173*0.57 (3)
C17B0.967 (2)0.045 (3)0.2318 (8)0.136 (9)0.43 (3)
H17C1.04910.01110.25240.164*0.43 (3)
H17D0.94060.13780.25110.164*0.43 (3)
C18B1.027 (3)0.078 (5)0.1915 (11)0.201 (15)0.43 (3)
H18D1.12320.14190.19770.302*0.43 (3)
H18E1.06080.01240.17290.302*0.43 (3)
H18F0.94690.13340.17050.302*0.43 (3)
N10.3493 (2)0.0030 (2)0.31573 (6)0.0420 (4)
N20.4446 (2)0.12399 (19)0.30664 (6)0.0407 (4)
O10.02722 (17)0.37131 (17)0.44539 (5)0.0441 (3)
O20.5521 (2)0.35450 (19)0.32838 (6)0.0604 (4)
O3A0.776 (2)0.037 (5)0.3148 (7)0.069 (5)0.50 (10)
O3B0.756 (4)0.019 (7)0.3125 (11)0.088 (6)0.50 (10)
O40.8114 (2)0.0497 (3)0.22828 (6)0.0776 (7)
Cl10.04000 (9)0.85141 (8)0.60423 (3)0.0730 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0478 (12)0.0520 (13)0.0493 (11)0.0015 (11)0.0142 (10)0.0084 (11)
C20.0546 (14)0.0482 (12)0.0626 (13)0.0075 (12)0.0102 (11)0.0050 (12)
C30.0488 (12)0.0569 (13)0.0443 (10)0.0067 (11)0.0026 (9)0.0085 (11)
C40.0382 (10)0.0484 (11)0.0358 (9)0.0006 (9)0.0078 (8)0.0005 (9)
C50.0345 (10)0.0498 (12)0.0359 (9)0.0013 (8)0.0070 (8)0.0022 (10)
C60.0447 (12)0.0665 (15)0.0367 (10)0.0003 (10)0.0053 (9)0.0045 (11)
C70.0416 (11)0.0528 (13)0.0401 (10)0.0069 (9)0.0050 (9)0.0063 (10)
C80.0390 (11)0.0473 (12)0.0430 (10)0.0028 (9)0.0124 (9)0.0046 (10)
C90.0465 (12)0.0468 (12)0.0483 (11)0.0017 (10)0.0151 (9)0.0004 (11)
C100.0324 (9)0.0403 (11)0.0377 (9)0.0021 (8)0.0025 (7)0.0010 (9)
C110.0407 (11)0.0402 (11)0.0433 (10)0.0007 (9)0.0069 (8)0.0071 (9)
C120.0364 (10)0.0396 (10)0.0466 (10)0.0023 (9)0.0049 (8)0.0003 (9)
C130.0342 (9)0.0410 (11)0.0400 (9)0.0008 (8)0.0001 (8)0.0031 (9)
C140.0514 (13)0.0480 (13)0.0549 (12)0.0116 (11)0.0066 (10)0.0053 (12)
C150.0453 (11)0.0537 (13)0.0390 (10)0.0022 (11)0.0098 (9)0.0005 (10)
C160.0521 (13)0.0725 (18)0.0463 (12)0.0110 (12)0.0144 (11)0.0093 (13)
C17A0.061 (5)0.144 (10)0.064 (4)0.038 (5)0.005 (4)0.003 (6)
C18A0.061 (5)0.197 (12)0.088 (6)0.058 (6)0.045 (4)0.051 (8)
C17B0.068 (7)0.191 (18)0.150 (13)0.082 (9)0.079 (8)0.109 (12)
C18B0.098 (14)0.31 (4)0.195 (19)0.098 (18)0.032 (12)0.15 (2)
N10.0421 (9)0.0420 (10)0.0420 (9)0.0047 (7)0.0043 (7)0.0046 (8)
N20.0385 (9)0.0433 (9)0.0403 (8)0.0028 (8)0.0092 (7)0.0037 (8)
O10.0458 (8)0.0520 (9)0.0345 (6)0.0025 (7)0.0015 (6)0.0032 (7)
O20.0626 (10)0.0545 (10)0.0640 (9)0.0194 (9)0.0233 (8)0.0068 (9)
O3A0.063 (4)0.096 (10)0.047 (4)0.021 (5)0.006 (3)0.022 (5)
O3B0.086 (7)0.110 (15)0.069 (5)0.038 (8)0.029 (4)0.046 (7)
O40.0519 (10)0.1259 (19)0.0549 (9)0.0329 (11)0.0193 (8)0.0216 (11)
Cl10.0791 (5)0.0674 (4)0.0725 (4)0.0034 (4)0.0133 (3)0.0271 (3)
Geometric parameters (Å, º) top
C1—C61.378 (3)C13—C141.498 (3)
C1—C21.392 (3)C14—H14A0.9600
C1—Cl11.742 (2)C14—H14B0.9600
C2—C31.376 (3)C14—H14C0.9600
C2—H20.9300C15—N21.461 (2)
C3—C41.380 (3)C15—C161.504 (3)
C3—H30.9300C15—H15A0.9700
C4—O11.370 (2)C15—H15B0.9700
C4—C51.391 (3)C16—O3A1.182 (17)
C5—C61.401 (3)C16—O3B1.234 (17)
C5—C71.439 (3)C16—O41.319 (2)
C6—H60.9300C17A—C18A1.316 (15)
C7—C81.345 (3)C17A—O41.470 (12)
C7—H70.9300C17A—H17A0.9700
C8—O11.380 (3)C17A—H17B0.9700
C8—C91.488 (3)C18A—H18A0.9600
C9—C101.520 (3)C18A—H18B0.9600
C9—H9A0.9700C18A—H18C0.9600
C9—H9B0.9700C17B—C18B1.16 (3)
C10—C111.344 (3)C17B—O41.493 (18)
C10—C131.434 (3)C17B—H17C0.9700
C11—C121.446 (3)C17B—H17D0.9700
C11—H110.9300C18B—H18D0.9600
C12—O21.228 (2)C18B—H18E0.9600
C12—N21.367 (3)C18B—H18F0.9600
C13—N11.305 (2)N1—N21.365 (2)
C6—C1—C2122.8 (2)H14A—C14—H14C109.5
C6—C1—Cl1119.41 (17)H14B—C14—H14C109.5
C2—C1—Cl1117.82 (18)N2—C15—C16111.14 (17)
C3—C2—C1120.7 (2)N2—C15—H15A109.4
C3—C2—H2119.7C16—C15—H15A109.4
C1—C2—H2119.7N2—C15—H15B109.4
C2—C3—C4116.43 (19)C16—C15—H15B109.4
C2—C3—H3121.8H15A—C15—H15B108.0
C4—C3—H3121.8O3A—C16—O3B24.8 (15)
O1—C4—C3125.54 (18)O3A—C16—O4123.2 (9)
O1—C4—C5110.30 (18)O3B—C16—O4123.6 (10)
C3—C4—C5124.13 (19)O3A—C16—C15125.6 (9)
C4—C5—C6118.7 (2)O3B—C16—C15124.9 (11)
C4—C5—C7105.27 (18)O4—C16—C15109.41 (19)
C6—C5—C7136.0 (2)C18A—C17A—O4115.8 (9)
C1—C6—C5117.23 (19)C18A—C17A—H17A108.3
C1—C6—H6121.4O4—C17A—H17A108.3
C5—C6—H6121.4C18A—C17A—H17B108.3
C8—C7—C5107.06 (19)O4—C17A—H17B108.3
C8—C7—H7126.5H17A—C17A—H17B107.4
C5—C7—H7126.5C17A—C18A—H18A109.5
C7—C8—O1111.11 (19)C17A—C18A—H18B109.5
C7—C8—C9134.0 (2)H18A—C18A—H18B109.5
O1—C8—C9114.88 (17)C17A—C18A—H18C109.5
C8—C9—C10114.63 (18)H18A—C18A—H18C109.5
C8—C9—H9A108.6H18B—C18A—H18C109.5
C10—C9—H9A108.6C18B—C17B—O4115.6 (19)
C8—C9—H9B108.6C18B—C17B—H17C108.3
C10—C9—H9B108.6O4—C17B—H17C108.4
H9A—C9—H9B107.6C18B—C17B—H17D108.5
C11—C10—C13118.60 (17)O4—C17B—H17D108.4
C11—C10—C9123.06 (18)H17C—C17B—H17D107.4
C13—C10—C9118.33 (18)C17B—C18B—H18D109.4
C10—C11—C12121.13 (18)C17B—C18B—H18E109.6
C10—C11—H11119.4H18D—C18B—H18E109.5
C12—C11—H11119.4C17B—C18B—H18F109.4
O2—C12—N2120.95 (17)H18D—C18B—H18F109.5
O2—C12—C11124.88 (19)H18E—C18B—H18F109.5
N2—C12—C11114.17 (17)C13—N1—N2117.70 (16)
N1—C13—C10122.17 (19)N1—N2—C12126.10 (15)
N1—C13—C14115.89 (18)N1—N2—C15114.57 (16)
C10—C13—C14121.94 (17)C12—N2—C15119.25 (16)
C13—C14—H14A109.5C4—O1—C8106.25 (15)
C13—C14—H14B109.5C16—O4—C17A119.7 (5)
H14A—C14—H14B109.5C16—O4—C17B114.9 (7)
C13—C14—H14C109.5C17A—O4—C17B17.9 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O3Bi0.932.373.291 (19)170
C15—H15B···O2ii0.972.343.278 (3)161
C18A—H18A···O2iii0.962.413.310 (10)156
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+1, y1/2, z+1/2; (iii) x+2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O3Bi0.932.373.291 (19)170
C15—H15B···O2ii0.972.343.278 (3)161
C18A—H18A···O2iii0.962.413.310 (10)156
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+1, y1/2, z+1/2; (iii) x+2, y1/2, z+1/2.
 

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