Literature DB >> 24046627

1-(3-Acetyl-phen-yl)-2-(2-oxidonaph-thalen-1-yl)diazen-1-ium.

Hassiba Bougueria1, Ali Benosmane, Mohamed Amine Benaouida, Abd El Kader Bouchoul, Salah Eddine Bouaoud.   

Abstract

The title compound, C18H14N2O2, crystallized with two independent zwitterion mol-ecules (A and B) in the asymmetric unit. They are both close to planar, the dihedral angle between the benzene ring and naphthalene ring system being 4.30 (9)° in A and 4.69 (9)° in B. Each mol-ecule has an E conformation with respect to the azo double bond. In each of the independent mol-ecules, an intra-molecular N-H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming -A-A-A- and -B-B-B- chains parallel to one another and propagating along the a-axis direction. There are also π-π inter-actions between adjacent mol-ecules involving benzene and naphthalene rings [centroid-centroid distance of 3.626 (3) Å for adjacent A mol-ecules and 3.652 (3) Å for adjacent B mol-ecules].

Entities:  

Year:  2013        PMID： 24046627      PMCID： PMC3772484          DOI： 10.1107/S1600536813014918

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background to azo compounds and their use in dyes, pigments and advanced materials, see: Lee et al. (2004 ▶); Oueslati et al. (2004 ▶). Many azo compounds have been synthesized by diazo­tization and diazo coupling reactions, see: Wang et al. (2003 ▶). For a related structure, see: Rãdulescu et al. (2006 ▶).

Experimental

Crystal data

C18H14N2O2 M = 290.31 Orthorhombic, a = 15.965 (5) Å b = 5.807 (5) Å c = 30.185 (5) Å V = 2798 (3) Å3 Z = 8 Mo Kα radiation μ = 0.09 mm−1 T = 150 K 0.26 × 0.22 × 0.17 mm

Data collection

Bruker APEXII diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.830, T max = 0.985 13123 measured reflections 5097 independent reflections 4621 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.120 S = 1.03 5097 reflections 399 parameters 1 restraint H-atom parameters constrained Δρmax = 0.24 e Å−3 Δρmin = −0.22 e Å−3 Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813014918/su2604sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014918/su2604Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813014918/su2604Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H14N2O2F(000) = 1216
Mr = 290.31Dx = 1.378 Mg m−3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 8593 reflections
a = 15.965 (5) Åθ = 2.7–27.5°
b = 5.807 (5) ŵ = 0.09 mm−1
c = 30.185 (5) ÅT = 150 K
V = 2798 (3) Å3Prism, red
Z = 80.26 × 0.22 × 0.17 mm
Bruker APEXII diffractometer5097 independent reflections
Radiation source: fine-focus sealed tube4621 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
CCD rotation images, thin slices scansθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)h = −20→17
Tmin = 0.830, Tmax = 0.985k = −6→7
13123 measured reflectionsl = −39→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.076P)2 + 0.6139P] where P = (Fo2 + 2Fc2)/3
5097 reflections(Δ/σ)max < 0.001
399 parametersΔρmax = 0.24 e Å−3
1 restraintΔρmin = −0.22 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.
xyzUiso*/Ueq
O10.88455 (10)0.0348 (3)0.91871 (6)0.0302 (5)
O220.46944 (10)0.5866 (3)0.85810 (8)0.0412 (7)
N120.71060 (12)0.1448 (3)0.91349 (6)0.0196 (5)
N130.76073 (11)0.2825 (3)0.89137 (6)0.0205 (5)
C20.83087 (14)−0.0922 (4)0.93640 (8)0.0221 (6)
C30.85443 (15)−0.3073 (4)0.95777 (8)0.0257 (7)
C40.79693 (15)−0.4408 (4)0.97746 (9)0.0244 (7)
C50.70855 (14)−0.3830 (4)0.97893 (7)0.0214 (6)
C60.65146 (16)−0.5256 (4)1.00018 (8)0.0266 (7)
C70.56723 (16)−0.4703 (4)1.00171 (9)0.0296 (7)
C80.53960 (15)−0.2689 (4)0.98130 (9)0.0279 (7)
C90.59476 (15)−0.1250 (4)0.95991 (8)0.0237 (6)
C100.68068 (14)−0.1781 (4)0.95840 (7)0.0186 (6)
C110.74111 (14)−0.0333 (4)0.93559 (8)0.0199 (6)
C140.72637 (14)0.4698 (4)0.86804 (8)0.0183 (6)
C150.78104 (13)0.6187 (4)0.84599 (8)0.0214 (6)
C160.74934 (15)0.8061 (4)0.82347 (8)0.0228 (7)
C170.66327 (14)0.8496 (4)0.82345 (8)0.0224 (6)
C180.60908 (13)0.7014 (4)0.84491 (8)0.0191 (6)
C190.64032 (13)0.5082 (4)0.86734 (8)0.0195 (6)
C200.51564 (14)0.7373 (4)0.84465 (8)0.0251 (6)
C210.48199 (16)0.9589 (5)0.82685 (10)0.0382 (9)
O310.93956 (10)0.5296 (3)0.64568 (7)0.0307 (5)
O520.52562 (10)1.0856 (3)0.70523 (8)0.0406 (6)
N420.76561 (11)0.6405 (3)0.65143 (7)0.0201 (5)
N430.81623 (11)0.7766 (3)0.67337 (6)0.0214 (5)
C320.88584 (14)0.4026 (4)0.62827 (8)0.0229 (6)
C330.90840 (15)0.1882 (4)0.60672 (8)0.0254 (7)
C340.85114 (15)0.0550 (4)0.58701 (8)0.0258 (7)
C350.76317 (15)0.1131 (4)0.58568 (8)0.0213 (6)
C360.70485 (16)−0.0288 (4)0.56436 (9)0.0277 (7)
C370.62120 (17)0.0288 (5)0.56317 (9)0.0304 (8)
C380.59387 (15)0.2310 (4)0.58362 (9)0.0290 (7)
C390.64969 (14)0.3723 (4)0.60486 (8)0.0238 (7)
C400.73576 (14)0.3193 (4)0.60642 (8)0.0210 (6)
C410.79672 (14)0.4629 (4)0.62934 (8)0.0192 (6)
C440.78179 (14)0.9636 (4)0.69705 (7)0.0194 (6)
C450.83625 (14)1.1076 (4)0.72006 (8)0.0226 (6)
C460.80436 (15)1.2942 (4)0.74318 (8)0.0244 (7)
C470.71858 (15)1.3399 (4)0.74312 (8)0.0236 (7)
C480.66479 (14)1.1958 (4)0.71987 (7)0.0208 (6)
C490.69584 (13)1.0051 (4)0.69702 (8)0.0202 (6)
C500.57227 (15)1.2340 (4)0.71913 (9)0.0258 (7)
C510.53792 (18)1.4575 (5)0.73668 (11)0.0427 (9)
H30.91030−0.352900.957800.0310*
H40.81450−0.576800.990800.0290*
H60.67010−0.660301.013600.0320*
H70.52950−0.566401.016200.0360*
H80.48300−0.231200.982200.0330*
H90.575100.008400.946400.0280*
H130.813900.258500.891200.0250*
H150.838400.591600.846500.0260*
H160.785400.903900.808300.0270*
H170.642400.978700.808900.0270*
H190.604000.407100.881600.0230*
H21A0.422500.964300.831300.0570*
H21B0.494100.969300.795800.0570*
H21C0.507801.085600.842100.0570*
H330.964200.142200.606600.0300*
H340.86870−0.080900.573600.0310*
H360.72290−0.163900.550800.0330*
H370.58310−0.066600.548800.0370*
H380.537400.270100.582800.0350*
H390.630400.505700.618500.0290*
H430.869400.752500.673300.0260*
H450.893601.078900.719900.0270*
H460.840501.389800.758900.0290*
H470.697501.465900.758500.0280*
H490.659600.907000.682000.0240*
H51A0.478001.457100.734200.0640*
H51B0.560401.583300.719800.0640*
H51C0.553501.474700.767200.0640*
U11U22U33U12U13U23
O10.0210 (8)0.0295 (9)0.0401 (10)−0.0016 (7)−0.0002 (8)0.0022 (8)
O220.0175 (8)0.0353 (10)0.0707 (15)−0.0053 (7)−0.0001 (9)0.0051 (10)
N120.0225 (9)0.0152 (8)0.0211 (9)−0.0013 (7)−0.0015 (8)−0.0018 (7)
N130.0177 (9)0.0172 (8)0.0266 (10)−0.0001 (7)0.0003 (8)0.0001 (8)
C20.0202 (11)0.0211 (10)0.0250 (12)0.0014 (9)−0.0047 (9)−0.0037 (10)
C30.0225 (11)0.0243 (11)0.0304 (13)0.0067 (9)−0.0079 (10)−0.0060 (10)
C40.0276 (12)0.0204 (11)0.0252 (13)0.0072 (10)−0.0093 (10)−0.0006 (9)
C50.0285 (12)0.0176 (10)0.0181 (11)0.0010 (9)−0.0042 (9)−0.0027 (9)
C60.0331 (13)0.0217 (11)0.0251 (12)0.0008 (10)−0.0053 (10)0.0023 (10)
C70.0312 (13)0.0289 (12)0.0287 (13)−0.0090 (10)−0.0001 (10)0.0058 (11)
C80.0211 (10)0.0292 (11)0.0333 (13)−0.0021 (10)−0.0004 (10)0.0014 (10)
C90.0252 (11)0.0216 (10)0.0243 (11)0.0017 (9)−0.0004 (9)−0.0004 (10)
C100.0212 (11)0.0171 (10)0.0175 (10)0.0024 (9)−0.0032 (9)−0.0044 (9)
C110.0223 (10)0.0162 (10)0.0212 (11)0.0022 (8)−0.0025 (9)−0.0031 (9)
C140.0197 (11)0.0153 (9)0.0198 (11)0.0009 (8)−0.0024 (9)−0.0031 (9)
C150.0158 (10)0.0228 (10)0.0255 (11)−0.0005 (8)−0.0010 (9)−0.0045 (9)
C160.0229 (11)0.0212 (11)0.0243 (12)−0.0050 (9)0.0019 (10)0.0012 (10)
C170.0268 (11)0.0189 (10)0.0215 (11)−0.0013 (9)−0.0030 (10)−0.0001 (9)
C180.0140 (10)0.0217 (10)0.0216 (11)0.0012 (8)−0.0016 (9)−0.0024 (9)
C190.0172 (10)0.0172 (9)0.0241 (11)−0.0030 (8)0.0005 (9)−0.0024 (8)
C200.0178 (10)0.0304 (11)0.0272 (12)−0.0008 (9)−0.0006 (9)−0.0027 (11)
C210.0233 (12)0.0479 (16)0.0433 (17)0.0109 (12)0.0039 (11)0.0118 (13)
O310.0209 (8)0.0282 (8)0.0431 (11)0.0002 (7)0.0030 (8)−0.0024 (8)
O520.0210 (9)0.0365 (10)0.0644 (14)−0.0070 (8)0.0033 (9)−0.0079 (10)
N420.0232 (9)0.0151 (8)0.0221 (9)0.0016 (7)0.0019 (8)0.0022 (8)
N430.0192 (9)0.0184 (8)0.0266 (10)0.0016 (7)0.0022 (8)0.0012 (8)
C320.0222 (10)0.0210 (10)0.0254 (12)0.0023 (9)0.0037 (9)0.0052 (9)
C330.0216 (11)0.0241 (11)0.0305 (13)0.0067 (9)0.0057 (10)0.0021 (10)
C340.0317 (12)0.0191 (10)0.0265 (12)0.0074 (10)0.0090 (10)0.0012 (9)
C350.0244 (12)0.0182 (10)0.0212 (11)0.0021 (9)0.0062 (9)0.0021 (10)
C360.0375 (14)0.0197 (11)0.0258 (12)−0.0011 (10)0.0059 (10)−0.0031 (10)
C370.0320 (13)0.0283 (12)0.0310 (14)−0.0043 (11)0.0030 (11)−0.0041 (11)
C380.0251 (12)0.0312 (12)0.0308 (13)0.0004 (10)0.0019 (11)−0.0018 (11)
C390.0214 (11)0.0221 (11)0.0279 (12)0.0020 (9)0.0032 (10)−0.0042 (10)
C400.0257 (12)0.0167 (10)0.0207 (11)0.0021 (9)0.0045 (9)0.0019 (9)
C410.0195 (10)0.0167 (10)0.0213 (12)0.0024 (8)0.0041 (9)0.0040 (9)
C440.0219 (10)0.0169 (9)0.0194 (11)0.0009 (8)0.0040 (9)0.0023 (9)
C450.0174 (10)0.0245 (10)0.0260 (12)−0.0010 (9)−0.0006 (9)0.0005 (9)
C460.0226 (11)0.0239 (11)0.0266 (12)−0.0047 (9)−0.0029 (9)−0.0033 (10)
C470.0246 (12)0.0204 (10)0.0257 (12)0.0014 (9)0.0029 (10)−0.0033 (10)
C480.0216 (11)0.0207 (10)0.0200 (11)−0.0006 (9)0.0034 (9)0.0023 (9)
C490.0207 (11)0.0175 (9)0.0224 (12)−0.0025 (8)0.0019 (9)0.0001 (9)
C500.0204 (12)0.0296 (12)0.0274 (13)0.0010 (10)0.0045 (10)−0.0001 (11)
C510.0296 (13)0.0503 (16)0.0483 (19)0.0136 (13)−0.0070 (13)−0.0217 (14)
O1—C21.250 (3)C16—H160.9300
O22—C201.214 (3)C17—H170.9300
O31—C321.247 (3)C19—H190.9300
O52—C501.214 (3)C21—H21B0.9600
N12—C111.324 (3)C21—H21C0.9600
N12—N131.314 (3)C21—H21A0.9600
N13—C141.407 (3)C32—C331.450 (4)
N13—H130.8600C32—C411.466 (3)
N42—N431.310 (3)C33—C341.337 (4)
N42—C411.325 (3)C34—C351.445 (4)
N43—C441.412 (3)C35—C401.420 (4)
N43—H430.8600C35—C361.400 (4)
C2—C111.474 (3)C36—C371.377 (4)
C2—C31.455 (4)C37—C381.397 (4)
C3—C41.341 (4)C38—C391.371 (4)
C4—C51.451 (4)C39—C401.409 (3)
C5—C101.413 (3)C40—C411.456 (3)
C5—C61.389 (4)C44—C451.392 (3)
C6—C71.383 (4)C44—C491.393 (3)
C7—C81.394 (4)C45—C461.386 (4)
C8—C91.375 (4)C46—C471.395 (4)
C9—C101.407 (3)C47—C481.389 (3)
C10—C111.453 (3)C48—C501.494 (4)
C14—C191.392 (3)C48—C491.396 (3)
C14—C151.397 (3)C50—C511.505 (4)
C15—C161.379 (4)C33—H330.9300
C16—C171.397 (3)C34—H340.9300
C17—C181.382 (3)C36—H360.9300
C18—C191.402 (3)C37—H370.9300
C18—C201.506 (3)C38—H380.9300
C20—C211.494 (4)C39—H390.9300
C3—H30.9300C45—H450.9300
C4—H40.9300C46—H460.9300
C6—H60.9300C47—H470.9300
C7—H70.9300C49—H490.9300
C8—H80.9300C51—H51A0.9600
C9—H90.9300C51—H51B0.9600
C15—H150.9300C51—H51C0.9600
O1···N122.854 (4)C41···C46vii3.575 (5)
O1···N132.580 (3)C41···C44vii3.555 (4)
O1···C20i3.336 (4)C44···C40vi3.506 (4)
O1···O22i3.165 (4)C44···C41vi3.555 (4)
O1···C8ii3.398 (4)C44···C34vi3.541 (4)
O1···C21i3.180 (4)C44···C35vi3.485 (4)
O22···C15iii3.256 (4)C45···C32vi3.352 (4)
O22···O1iii3.165 (4)C45···C41vi3.486 (5)
O31···N422.856 (3)C45···O52iv3.256 (4)
O31···N432.575 (3)C46···C41vi3.575 (5)
O31···C50iv3.360 (4)C47···N42vi3.357 (4)
O31···C51iv3.165 (5)C49···C39vi3.582 (5)
O31···O52iv3.180 (4)C49···C35vi3.584 (5)
O31···C38i3.393 (4)C49···C40vi3.349 (4)
O52···C45v3.256 (4)C50···O31v3.360 (4)
O52···O31v3.180 (4)C51···O31v3.165 (5)
O1···H21Ai2.7100C2···H132.4700
O1···H8ii2.7300C4···H36viii2.7500
O1···H131.9100C5···H36viii2.7400
O22···H192.4900C7···H3xiii3.0100
O22···H15iii2.3600C8···H3xiii3.1000
O22···H13iii2.8200C15···H46vii3.0900
O31···H431.9000C15···H47vii3.0900
O31···H38i2.7200C16···H21Aiv3.0800
O31···H51Aiv2.7400C16···H47vii2.9000
O52···H45v2.3600C17···H21C2.8900
O52···H21B2.8600C17···H21B2.9100
O52···H492.4800C17···H47vii3.0200
O52···H43v2.8300C18···H51Cvii2.8300
N12···O12.854 (4)C20···H51Cvii2.8600
N12···C4vi3.379 (4)C21···H172.6200
N12···C5vi3.380 (4)C32···H432.4600
N12···C17vii3.301 (4)C34···H6xi2.7900
N12···C6vi3.377 (4)C35···H6xi2.7600
N12···C16vii3.411 (4)C37···H33x3.0000
N13···C4vi3.110 (4)C38···H33x3.0800
N13···C5vi3.384 (4)C45···H163.0300
N13···O12.580 (3)C46···H163.0200
N13···C16vii3.448 (4)C47···H51C2.8400
N42···C47vii3.357 (4)C47···H51B2.9800
N42···O312.856 (3)C48···H172.9900
N42···C36vi3.397 (4)C50···H21B3.0500
N42···C35vi3.387 (4)C51···H472.6300
N42···C34vi3.382 (4)H3···C7xiv3.0100
N43···C35vi3.397 (4)H3···C8xiv3.1000
N43···O312.575 (3)H4···H62.4500
N43···C34vi3.118 (4)H6···H42.4500
N12···H92.5100H6···C34ix2.7900
N12···H192.4800H6···C35ix2.7600
N42···H392.5000H8···O1x2.7300
N42···H492.4700H9···N122.5100
C2···C15vii3.301 (4)H13···C22.4700
C3···C15vii3.598 (5)H13···H152.3900
C4···N13vii3.110 (4)H13···O22i2.8200
C4···C14vii3.528 (5)H13···O11.9100
C4···N12vii3.379 (4)H15···H132.3900
C4···C36viii3.550 (5)H15···O22i2.3600
C5···N13vii3.384 (4)H16···C463.0200
C5···N12vii3.380 (4)H16···H21Aiv2.4200
C5···C36viii3.577 (5)H16···C453.0300
C5···C14vii3.466 (4)H17···C212.6200
C5···C19vii3.596 (4)H17···C482.9900
C6···C35ix3.595 (5)H17···H21B2.4000
C6···N12vii3.377 (4)H17···H21C2.4500
C6···C34ix3.578 (5)H19···O222.4900
C8···O1x3.398 (4)H19···N122.4800
C9···C19vii3.588 (5)H21A···O1iii2.7100
C10···C19vii3.360 (4)H21A···H16v2.4200
C10···C14vii3.486 (4)H21A···C16v3.0800
C11···C14vii3.541 (5)H21B···C172.9100
C11···C16vii3.513 (5)H21B···C503.0500
C11···C15vii3.436 (4)H21B···O522.8600
C14···C4vi3.528 (5)H21B···H172.4000
C14···C5vi3.466 (4)H21C···C172.8900
C14···C11vi3.541 (5)H21C···H172.4500
C14···C10vi3.486 (4)H33···C37ii3.0000
C15···C3vi3.598 (5)H33···C38ii3.0800
C15···O22i3.256 (4)H34···H362.4700
C15···C2vi3.301 (4)H36···H342.4700
C15···C11vi3.436 (4)H36···C4xii2.7500
C16···N13vi3.448 (4)H36···C5xii2.7400
C16···C11vi3.513 (5)H38···O31iii2.7200
C16···N12vi3.411 (4)H39···N422.5000
C17···N12vi3.301 (4)H43···O311.9000
C19···C5vi3.596 (4)H43···C322.4600
C19···C10vi3.360 (4)H43···H452.3900
C19···C9vi3.588 (5)H43···O52iv2.8300
C20···O1iii3.336 (4)H45···H432.3900
C21···O1iii3.180 (4)H45···O52iv2.3600
C32···C45vii3.352 (4)H46···C15vi3.0900
C34···N42vii3.382 (4)H46···H51Axv2.4800
C34···C6xi3.578 (5)H47···C15vi3.0900
C34···N43vii3.118 (4)H47···C16vi2.9000
C34···C44vii3.541 (4)H47···C17vi3.0200
C35···C44vii3.485 (4)H47···C512.6300
C35···C6xi3.595 (5)H47···H51B2.5700
C35···N43vii3.397 (4)H47···H51C2.3100
C35···N42vii3.387 (4)H49···O522.4800
C35···C49vii3.584 (5)H49···N422.4700
C36···N42vii3.397 (4)H51A···O31v2.7400
C36···C5xii3.577 (5)H51A···H46xvi2.4800
C36···C4xii3.550 (5)H51B···C472.9800
C38···O31iii3.393 (4)H51B···H472.5700
C39···C49vii3.582 (5)H51C···C18vi2.8300
C40···C49vii3.349 (4)H51C···C20vi2.8600
C40···C44vii3.506 (4)H51C···C472.8400
C41···C45vii3.486 (5)H51C···H472.3100
N13—N12—C11120.50 (19)H21A—C21—H21B110.00
N12—N13—C14119.17 (18)C20—C21—H21A109.00
N12—N13—H13120.00C20—C21—H21B109.00
C14—N13—H13120.00C20—C21—H21C109.00
N43—N42—C41119.53 (18)C33—C32—C41117.1 (2)
N42—N43—C44118.67 (17)O31—C32—C41121.1 (2)
N42—N43—H43121.00O31—C32—C33121.7 (2)
C44—N43—H43121.00C32—C33—C34121.8 (2)
O1—C2—C11121.5 (2)C33—C34—C35122.8 (2)
O1—C2—C3121.2 (2)C34—C35—C36121.5 (2)
C3—C2—C11117.3 (2)C34—C35—C40119.0 (2)
C2—C3—C4121.1 (2)C36—C35—C40119.6 (2)
C3—C4—C5123.1 (2)C35—C36—C37120.9 (2)
C4—C5—C6121.0 (2)C36—C37—C38119.7 (2)
C6—C5—C10119.9 (2)C37—C38—C39120.5 (2)
C4—C5—C10119.2 (2)C38—C39—C40121.3 (2)
C5—C6—C7121.0 (2)C35—C40—C39118.0 (2)
C6—C7—C8119.2 (2)C35—C40—C41119.1 (2)
C7—C8—C9121.0 (2)C39—C40—C41122.9 (2)
C8—C9—C10120.4 (2)N42—C41—C32124.1 (2)
C5—C10—C9118.5 (2)C32—C41—C40120.1 (2)
C5—C10—C11119.1 (2)N42—C41—C40115.7 (2)
C9—C10—C11122.4 (2)N43—C44—C49121.1 (2)
C2—C11—C10120.2 (2)C45—C44—C49120.8 (2)
N12—C11—C2123.2 (2)N43—C44—C45118.1 (2)
N12—C11—C10116.5 (2)C44—C45—C46119.4 (2)
C15—C14—C19120.7 (2)C45—C46—C47120.6 (2)
N13—C14—C19121.1 (2)C46—C47—C48119.5 (2)
N13—C14—C15118.24 (19)C49—C48—C50117.5 (2)
C14—C15—C16119.6 (2)C47—C48—C49120.5 (2)
C15—C16—C17120.3 (2)C47—C48—C50122.0 (2)
C16—C17—C18120.2 (2)C44—C49—C48119.1 (2)
C19—C18—C20117.8 (2)C48—C50—C51118.9 (2)
C17—C18—C20122.1 (2)O52—C50—C48120.4 (2)
C17—C18—C19120.1 (2)O52—C50—C51120.7 (2)
C14—C19—C18119.1 (2)C32—C33—H33119.00
C18—C20—C21118.5 (2)C34—C33—H33119.00
O22—C20—C18120.0 (2)C33—C34—H34119.00
O22—C20—C21121.5 (2)C35—C34—H34119.00
C4—C3—H3119.00C35—C36—H36119.00
C2—C3—H3120.00C37—C36—H36120.00
C3—C4—H4118.00C36—C37—H37120.00
C5—C4—H4118.00C38—C37—H37120.00
C5—C6—H6120.00C37—C38—H38120.00
C7—C6—H6119.00C39—C38—H38120.00
C6—C7—H7120.00C38—C39—H39119.00
C8—C7—H7120.00C40—C39—H39119.00
C9—C8—H8120.00C44—C45—H45120.00
C7—C8—H8119.00C46—C45—H45120.00
C8—C9—H9120.00C45—C46—H46120.00
C10—C9—H9120.00C47—C46—H46120.00
C16—C15—H15120.00C46—C47—H47120.00
C14—C15—H15120.00C48—C47—H47120.00
C17—C16—H16120.00C44—C49—H49120.00
C15—C16—H16120.00C48—C49—H49120.00
C18—C17—H17120.00C50—C51—H51A109.00
C16—C17—H17120.00C50—C51—H51B109.00
C14—C19—H19120.00C50—C51—H51C109.00
C18—C19—H19120.00H51A—C51—H51B109.00
H21A—C21—H21C109.00H51A—C51—H51C109.00
H21B—C21—H21C109.00H51B—C51—H51C109.00
C11—N12—N13—C14179.7 (2)C19—C18—C20—C21171.1 (2)
N13—N12—C11—C2−1.2 (3)C17—C18—C19—C140.7 (4)
N13—N12—C11—C10−178.94 (19)C20—C18—C19—C14179.8 (2)
N12—N13—C14—C15177.8 (2)C17—C18—C20—O22169.1 (2)
N12—N13—C14—C19−1.3 (3)C17—C18—C20—C21−9.9 (4)
C41—N42—N43—C44−179.4 (2)O31—C32—C33—C34−178.2 (2)
N43—N42—C41—C321.3 (3)C41—C32—C33—C342.7 (3)
N43—N42—C41—C40179.2 (2)O31—C32—C41—N42−6.0 (4)
N42—N43—C44—C45−179.7 (2)O31—C32—C41—C40176.2 (2)
N42—N43—C44—C49−0.5 (3)C33—C32—C41—N42173.1 (2)
C3—C2—C11—C104.6 (3)C33—C32—C41—C40−4.7 (3)
O1—C2—C11—N125.5 (4)C32—C33—C34—C35−0.1 (4)
O1—C2—C3—C4178.7 (2)C33—C34—C35—C36179.3 (2)
C11—C2—C3—C4−2.7 (4)C33—C34—C35—C40−0.5 (4)
O1—C2—C11—C10−176.8 (2)C34—C35—C36—C37−179.8 (2)
C3—C2—C11—N12−173.1 (2)C40—C35—C36—C370.1 (4)
C2—C3—C4—C50.1 (4)C34—C35—C40—C39−179.8 (2)
C3—C4—C5—C6−179.3 (2)C34—C35—C40—C41−1.5 (3)
C3—C4—C5—C100.7 (4)C36—C35—C40—C390.4 (3)
C4—C5—C10—C111.3 (3)C36—C35—C40—C41178.7 (2)
C4—C5—C6—C7179.8 (2)C35—C36—C37—C38−0.2 (4)
C6—C5—C10—C9−0.4 (3)C36—C37—C38—C390.0 (4)
C6—C5—C10—C11−178.8 (2)C37—C38—C39—C400.5 (4)
C10—C5—C6—C7−0.1 (3)C38—C39—C40—C35−0.7 (4)
C4—C5—C10—C9179.7 (2)C38—C39—C40—C41−178.9 (2)
C5—C6—C7—C80.4 (4)C35—C40—C41—N42−173.8 (2)
C6—C7—C8—C9−0.2 (4)C35—C40—C41—C324.2 (3)
C7—C8—C9—C10−0.3 (4)C39—C40—C41—N424.4 (3)
C8—C9—C10—C50.6 (3)C39—C40—C41—C32−177.7 (2)
C8—C9—C10—C11179.0 (2)N43—C44—C45—C46179.2 (2)
C5—C10—C11—C2−3.9 (3)C49—C44—C45—C460.0 (3)
C9—C10—C11—N12−4.5 (3)N43—C44—C49—C48−178.2 (2)
C5—C10—C11—N12173.9 (2)C45—C44—C49—C481.0 (3)
C9—C10—C11—C2177.7 (2)C44—C45—C46—C47−0.7 (4)
N13—C14—C15—C16−178.9 (2)C45—C46—C47—C480.4 (4)
C19—C14—C15—C160.3 (4)C46—C47—C48—C490.6 (3)
C15—C14—C19—C18−1.3 (4)C46—C47—C48—C50179.1 (2)
N13—C14—C19—C18177.9 (2)C47—C48—C49—C44−1.3 (3)
C14—C15—C16—C171.3 (4)C50—C48—C49—C44−179.9 (2)
C15—C16—C17—C18−1.9 (4)C47—C48—C50—O52−167.2 (3)
C16—C17—C18—C190.9 (4)C47—C48—C50—C5111.7 (4)
C16—C17—C18—C20−178.2 (2)C49—C48—C50—O5211.3 (4)
C19—C18—C20—O22−10.0 (4)C49—C48—C50—C51−169.8 (2)
D—H···AD—HH···AD···AD—H···A
N13—H13···O10.861.912.580 (3)134
N43—H43···O310.861.902.575 (3)134
C15—H15···O22i0.932.363.256 (4)162
C45—H45···O52iv0.932.363.256 (4)162
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N13—H13⋯O10.861.912.580 (3)134
N43—H43⋯O310.861.902.575 (3)134
C15—H15⋯O22i 0.932.363.256 (4)162
C45—H45⋯O52ii 0.932.363.256 (4)162

Symmetry codes: (i) ; (ii) .

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