Literature DB >> 24109318

(E)-6,8-Di-chloro-3-{[(naphthalen-1-ylmeth-yl)iminiumyl]meth-yl}-2H-chromen-4-olate.

Yoshinobu Ishikawa1, Yuya Motohashi.   

Abstract

In the title compound, C21H15Cl2NO2, the H atom of the -OH group is transferred to the N atom of the imine, forming a zwitterion. Thus, there is formation of a six-membered ring via an intra-molecular O⋯H-N, rather than O-H⋯N, hydrogen bond in the mol-ecule. The dihedral angle between the naphthalene ring system and the benzene ring of the 2H-chromen system is 87.41 (4)°. In the crystal, the mol-ecules are packed through N-H⋯O, π-π [centroid-centroid distances = 3.744 (3) and 3.780 (3) Å], C-Cl⋯π [Cl⋯centroid = 3.261 (3) Å], C-H⋯π and C-H⋯O inter-actions.

Entities:  

Year:  2013        PMID： 24109318      PMCID： PMC3793731          DOI： 10.1107/S1600536813018084

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


Related literature

For the biological propertries of similar structures, see: Khan et al. (2009 ▶); Tu et al. (2013 ▶). For related structures, see: Benaouida et al. (2013 ▶); Małecka & Budzisz (2006 ▶).

Experimental

Crystal data

C21H15Cl2NO2 M = 384.26 Monoclinic, a = 16.286 (7) Å b = 8.910 (6) Å c = 12.008 (9) Å β = 102.65 (4)° V = 1700.2 (19) Å3 Z = 4 Mo Kα radiation μ = 0.40 mm−1 T = 100 K 0.37 × 0.37 × 0.28 mm

Data collection

Rigaku AFC7R diffractometer 4657 measured reflections 3875 independent reflections 3367 reflections with F 2 > 2.0σ(F 2) R int = 0.083 3 standard reflections every 150 reflections intensity decay: −0.4%

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.083 S = 1.04 3875 reflections 235 parameters H-atom parameters constrained Δρmax = 0.49 e Å−3 Δρmin = −0.53 e Å−3 Data collection: WinAFC (Rigaku, 1999 ▶); cell refinement: WinAFC; data reduction: WinAFC; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: CrystalStructure. Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S1600536813018084/zp2006sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018084/zp2006Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H15Cl2NO2F(000) = 792.00
Mr = 384.26Dx = 1.501 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 16.286 (7) Åθ = 15.7–17.5°
b = 8.910 (6) ŵ = 0.40 mm−1
c = 12.008 (9) ÅT = 100 K
β = 102.65 (4)°Block, yellow
V = 1700.2 (19) Å30.37 × 0.37 × 0.28 mm
Z = 4
Rigaku AFC7R diffractometerθmax = 27.6°
ω–2θ scansh = −20→21
4657 measured reflectionsk = 0→11
3875 independent reflectionsl = −15→8
3367 reflections with F2 > 2.0σ(F2)3 standard reflections every 150 reflections
Rint = 0.083 intensity decay: −0.4%
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0433P)2 + 0.7479P] where P = (Fo2 + 2Fc2)/3
3875 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.49 e Å−3
0 restraintsΔρmin = −0.53 e Å−3
Primary atom site location: structure-invariant direct methods
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).
xyzUiso*/Ueq
Cl10.10099 (2)0.41074 (4)0.50407 (3)0.02134 (10)
Cl20.17147 (2)0.84582 (4)0.82092 (3)0.01871 (10)
O10.34501 (6)0.79385 (11)0.80754 (9)0.0176 (2)
O20.43015 (6)0.52671 (12)0.57813 (9)0.0194 (2)
N10.58885 (7)0.64807 (13)0.66903 (11)0.0178 (3)
C10.42933 (8)0.73258 (16)0.84317 (12)0.0173 (3)
C20.46328 (8)0.67928 (15)0.74377 (12)0.0163 (3)
C30.40821 (8)0.59345 (15)0.65803 (12)0.0153 (3)
C40.25901 (8)0.50521 (16)0.59487 (11)0.0149 (3)
C50.17435 (8)0.52122 (16)0.59411 (11)0.0156 (3)
C60.14631 (8)0.62656 (15)0.66285 (11)0.0152 (3)
C70.20515 (8)0.71380 (15)0.73498 (11)0.0141 (3)
C80.29135 (8)0.69931 (15)0.73910 (11)0.0142 (3)
C90.31801 (8)0.59510 (15)0.66686 (11)0.0148 (3)
C100.54680 (8)0.70260 (15)0.74329 (12)0.0166 (3)
C110.67892 (8)0.67249 (16)0.68340 (12)0.0174 (3)
C120.70249 (8)0.80052 (15)0.61334 (11)0.0140 (3)
C130.64295 (9)0.87459 (16)0.53406 (12)0.0176 (3)
C140.66574 (9)0.99175 (17)0.46685 (12)0.0208 (3)
C150.74839 (10)1.03185 (17)0.47995 (12)0.0210 (3)
C160.89800 (9)0.99932 (17)0.57563 (13)0.0212 (3)
C170.95874 (9)0.93028 (17)0.65587 (13)0.0219 (3)
C180.93670 (9)0.81701 (16)0.72581 (12)0.0193 (3)
C190.85400 (8)0.77372 (15)0.71310 (12)0.0157 (3)
C200.78937 (8)0.84224 (14)0.63022 (11)0.0133 (3)
C210.81193 (9)0.95853 (16)0.56097 (12)0.0170 (3)
H1B0.42830.64760.89600.0207*
H2A0.46720.81060.88500.0207*
H30.27690.43340.54660.0179*
H40.08790.63820.66030.0182*
H50.57770.76430.80240.0199*
H60.56170.59620.61000.0213*
H7A0.70480.57910.66260.0209*
H8B0.70330.69250.76510.0209*
H90.58550.84700.52400.0211*
H100.62361.04240.41270.0249*
H110.76331.10980.43410.0252*
H120.91351.07570.52900.0255*
H131.01600.95880.66450.0263*
H140.97910.77020.78200.0231*
H150.84000.69680.76050.0188*
U11U22U33U12U13U23
Cl10.01563 (16)0.0285 (2)0.01929 (17)−0.00243 (13)0.00266 (12)−0.00941 (13)
Cl20.01504 (16)0.01710 (17)0.02549 (18)−0.00033 (12)0.00772 (12)−0.00669 (13)
O10.0124 (5)0.0160 (5)0.0241 (5)0.0000 (4)0.0036 (4)−0.0044 (4)
O20.0161 (5)0.0212 (5)0.0225 (5)0.0025 (4)0.0078 (4)−0.0020 (4)
N10.0120 (6)0.0189 (6)0.0228 (6)−0.0021 (5)0.0046 (5)−0.0003 (5)
C10.0116 (6)0.0192 (7)0.0204 (7)0.0005 (5)0.0020 (5)−0.0002 (6)
C20.0139 (6)0.0148 (7)0.0210 (7)0.0018 (5)0.0053 (5)0.0031 (6)
C30.0138 (6)0.0135 (6)0.0197 (7)0.0027 (5)0.0061 (5)0.0043 (5)
C40.0160 (6)0.0162 (6)0.0134 (6)0.0024 (5)0.0048 (5)0.0004 (5)
C50.0155 (7)0.0170 (7)0.0141 (6)−0.0015 (5)0.0024 (5)0.0006 (5)
C60.0125 (6)0.0174 (7)0.0165 (6)0.0008 (5)0.0051 (5)0.0021 (5)
C70.0155 (6)0.0118 (6)0.0164 (6)0.0024 (5)0.0068 (5)0.0007 (5)
C80.0137 (6)0.0128 (6)0.0162 (6)−0.0001 (5)0.0039 (5)0.0022 (5)
C90.0138 (6)0.0150 (7)0.0165 (6)0.0018 (5)0.0053 (5)0.0033 (5)
C100.0146 (6)0.0142 (6)0.0206 (7)0.0000 (5)0.0032 (5)0.0037 (6)
C110.0110 (6)0.0173 (7)0.0245 (7)0.0012 (5)0.0050 (5)0.0044 (6)
C120.0140 (6)0.0132 (6)0.0155 (6)0.0001 (5)0.0051 (5)−0.0018 (5)
C130.0162 (7)0.0183 (7)0.0177 (7)0.0011 (5)0.0021 (5)−0.0014 (6)
C140.0244 (7)0.0205 (7)0.0157 (7)0.0033 (6)0.0003 (6)0.0017 (6)
C150.0282 (8)0.0187 (7)0.0172 (7)−0.0015 (6)0.0072 (6)0.0027 (6)
C160.0231 (8)0.0187 (7)0.0246 (7)−0.0042 (6)0.0110 (6)0.0001 (6)
C170.0153 (7)0.0224 (8)0.0298 (8)−0.0038 (6)0.0089 (6)−0.0056 (6)
C180.0150 (7)0.0206 (7)0.0219 (7)0.0030 (6)0.0035 (6)−0.0033 (6)
C190.0161 (6)0.0143 (6)0.0173 (7)0.0004 (5)0.0050 (5)−0.0017 (5)
C200.0144 (6)0.0127 (6)0.0137 (6)−0.0000 (5)0.0050 (5)−0.0029 (5)
C210.0199 (7)0.0157 (7)0.0169 (7)−0.0008 (6)0.0072 (5)−0.0021 (6)
Cl1—C51.7319 (15)C15—C211.415 (2)
Cl2—C71.7313 (17)C16—C171.367 (2)
O1—C11.4524 (17)C16—C211.421 (3)
O1—C81.3543 (17)C17—C181.409 (3)
O2—C31.246 (2)C18—C191.377 (2)
N1—C101.330 (3)C19—C201.4185 (19)
N1—C111.4554 (19)C20—C211.426 (3)
C1—C21.498 (3)N1—H60.880
C2—C31.430 (2)C1—H1B0.990
C2—C101.377 (2)C1—H2A0.990
C3—C91.496 (2)C4—H30.950
C4—C51.384 (2)C6—H40.950
C4—C91.3958 (19)C10—H50.950
C5—C61.391 (2)C11—H7A0.990
C6—C71.3817 (19)C11—H8B0.990
C7—C81.400 (2)C13—H90.950
C8—C91.403 (2)C14—H100.950
C11—C121.516 (3)C15—H110.950
C12—C131.3703 (19)C16—H120.950
C12—C201.434 (2)C17—H130.950
C13—C141.418 (3)C18—H140.950
C14—C151.368 (3)C19—H150.950
Cl2···O12.9030 (16)C2···H9iv3.5215
O1···C32.878 (3)C2···H10vi3.2427
O2···N12.7938 (19)C2···H10iv3.5375
O2···C42.844 (2)C3···H2Aii3.3458
O2···C102.889 (2)C3···H5ii2.9718
N1···C32.956 (2)C3···H10vi3.3648
N1···C132.846 (3)C4···H5ii3.4301
C1···C92.755 (3)C4···H7Aiii3.3561
C2···C82.794 (3)C4···H8Bii3.2427
C4···C72.775 (3)C4···H11vi3.4591
C5···C82.780 (3)C5···H11vi3.4793
C6···C92.800 (3)C5···H15ii3.4109
C10···C123.370 (3)C6···H11vi3.1293
C10···C133.583 (3)C6···H12vi3.5089
C11···C192.937 (3)C6···H14viii3.5789
C12···C152.810 (3)C7···H11vi2.7047
C13···C212.801 (3)C8···H7Av3.5798
C14···C202.819 (3)C8···H10vi3.4120
C16···C192.792 (3)C8···H11vi2.6837
C17···C202.819 (3)C9···H5ii3.3815
C18···C212.806 (3)C9···H10vi3.5560
Cl1···Cl2i3.4590 (17)C9···H11vi3.0717
Cl1···C18ii3.531 (3)C10···H9iv3.3197
Cl1···C18iii3.372 (3)C10···H10iv3.0585
Cl1···C19ii3.531 (3)C11···H3iii3.1482
Cl1···C19iii3.298 (3)C12···H3iii2.9038
Cl1···C20iii3.483 (2)C13···H1Bv2.8981
Cl2···Cl1iv3.4590 (17)C13···H1Bi3.5306
Cl2···C4iv3.544 (3)C13···H2Ai3.4463
Cl2···C5iv3.478 (3)C13···H3iii3.2759
O1···N1v3.327 (3)C13···H5i3.0174
O1···C11v3.401 (3)C14···H1Bv2.8448
O2···O2iii3.285 (3)C14···H5i3.1497
O2···N1iii3.306 (3)C14···H8Bi3.0966
O2···C1ii3.472 (3)C15···H8Bi3.2195
O2···C1i3.542 (3)C16···H4v3.3653
O2···C10ii3.567 (3)C16···H13ix3.4908
N1···O1ii3.327 (3)C16···H14x3.3549
N1···O2iii3.306 (3)C17···H4xi3.3395
C1···O2v3.472 (3)C17···H4v3.1019
C1···O2iv3.542 (3)C17···H12ix3.3585
C4···Cl2i3.544 (3)C17···H14x3.2288
C5···Cl2i3.478 (3)C18···H4xi3.1738
C5···C19ii3.302 (3)C18···H4v3.2351
C6···C16ii3.558 (3)C18···H13xii3.4745
C6···C17ii3.515 (3)C20···H3iii3.2717
C6···C18ii3.466 (3)H1B···C13ii2.8981
C6···C19ii3.479 (3)H1B···C13iv3.5306
C6···C20ii3.542 (3)H1B···C14ii2.8448
C6···C21ii3.566 (3)H1B···H9ii2.8715
C7···C21ii3.399 (3)H1B···H9iv2.6810
C8···C15vi3.511 (3)H1B···H10ii2.7785
C10···O2v3.567 (3)H1B···H10iv3.5696
C10···C13iv3.567 (3)H2A···O2v2.5248
C10···C14iv3.418 (3)H2A···O2iv2.9081
C11···O1ii3.401 (3)H2A···N1v3.1678
C13···C10i3.567 (3)H2A···N1iv3.5686
C14···C10i3.418 (3)H2A···C3v3.3458
C15···C8vi3.511 (3)H2A···C13iv3.4463
C16···C6v3.558 (3)H2A···H6v2.5906
C17···C6v3.515 (3)H2A···H6iv2.9221
C18···Cl1v3.531 (3)H2A···H9iv2.6567
C18···Cl1iii3.372 (3)H3···Cl2i3.4819
C18···C6v3.466 (3)H3···C11iii3.1482
C19···Cl1v3.531 (3)H3···C12iii2.9038
C19···Cl1iii3.298 (3)H3···C13iii3.2759
C19···C5v3.302 (3)H3···C20iii3.2717
C19···C6v3.479 (3)H3···H5ii3.0475
C20···Cl1iii3.483 (2)H3···H6iii3.5623
C20···C6v3.542 (3)H3···H7Aiii2.5963
C21···C6v3.566 (3)H3···H8Bii3.0827
C21···C7v3.399 (3)H3···H9iii3.5808
Cl1···H32.8044H4···Cl1vii3.3003
Cl1···H42.8011H4···C16ii3.3653
Cl2···H42.8007H4···C17viii3.3395
O2···H32.5793H4···C17ii3.1019
O2···H62.1816H4···C18viii3.1738
N1···H92.4771H4···C18ii3.2351
C1···H52.5838H4···H12vi3.4114
C2···H62.6121H4···H13viii3.0915
C3···H1B2.8456H4···H13ii3.3779
C3···H2A3.3086H4···H14viii2.7925
C3···H32.6730H4···H14ii3.5715
C3···H53.2932H5···O2v2.7607
C3···H62.6854H5···C3v2.9718
C4···H43.2775H5···C4v3.4301
C6···H33.2754H5···C9v3.3815
C8···H1B2.6266H5···C13iv3.0174
C8···H2A3.1711H5···C14iv3.1497
C8···H33.2817H5···H3v3.0475
C8···H43.2853H5···H9iv2.8161
C9···H1B2.9757H5···H10iv3.0576
C10···H1B2.9791H6···O1ii3.1444
C10···H2A2.5432H6···O2iii2.5402
C10···H7A3.1414H6···C1ii3.2859
C10···H8B2.5054H6···H2Aii2.5906
C10···H93.1166H6···H2Ai2.9221
C11···H52.5417H6···H3iii3.5623
C11···H92.6689H6···H6iii3.4103
C11···H152.5932H7A···Cl2ii2.8708
C12···H53.3778H7A···O1ii2.7154
C12···H62.9216H7A···O2iii3.3604
C12···H103.2782H7A···C4iii3.3561
C12···H152.6946H7A···C8ii3.5798
C13···H63.0440H7A···H3iii2.5963
C13···H7A3.1064H8B···C4v3.2427
C13···H8B3.1775H8B···C14iv3.0966
C13···H113.2717H8B···C15iv3.2195
C15···H93.2633H8B···H3v3.0827
C15···H122.6531H8B···H10iv3.1963
C16···H112.6523H8B···H11iv3.3862
C16···H143.2588H9···O2iii3.5379
C17···H153.2725H9···C1i3.0434
C18···H123.2633H9···C2i3.5215
C19···H7A2.9380H9···C10i3.3197
C19···H8B2.7588H9···H1Bv2.8715
C19···H133.2701H9···H1Bi2.6810
C20···H7A2.7891H9···H2Ai2.6567
C20···H8B2.7134H9···H3iii3.5808
C20···H93.2869H9···H5i2.8161
C20···H113.3119H10···O1vi3.1583
C20···H123.3119H10···N1i3.3222
C20···H143.2890H10···C2vi3.2427
C21···H103.2781H10···C2i3.5375
C21···H133.2836H10···C3vi3.3648
C21···H153.3029H10···C8vi3.4120
H1B···H53.0755H10···C9vi3.5560
H2A···H52.2747H10···C10i3.0585
H5···H62.7173H10···H1Bv2.7785
H5···H7A3.3695H10···H1Bi3.5696
H5···H8B2.2788H10···H5i3.0576
H5···H93.4527H10···H8Bi3.1963
H6···H7A2.2832H11···Cl2v3.5822
H6···H8B2.7639H11···Cl2vi3.4771
H6···H92.5271H11···O1vi3.1669
H7A···H93.2912H11···C4vi3.4591
H7A···H152.4895H11···C5vi3.4793
H8B···H93.3945H11···C6vi3.1293
H8B···H152.2403H11···C7vi2.7047
H9···H102.3596H11···C8vi2.6837
H10···H112.3125H11···C9vi3.0717
H11···H122.4808H11···H8Bi3.3862
H12···H132.3085H12···Cl2v3.4716
H13···H142.3547H12···C6vi3.5089
H14···H152.3174H12···C17ix3.3585
Cl1···H4vii3.3003H12···H4vi3.4114
Cl1···H14ii3.3665H12···H12ix3.3307
Cl1···H15ii3.3698H12···H13ix2.8245
Cl2···H3iv3.4819H12···H14x3.0781
Cl2···H7Av2.8708H13···Cl2xi2.9779
Cl2···H11ii3.5822H13···C16ix3.4908
Cl2···H11vi3.4771H13···C18x3.4745
Cl2···H12ii3.4716H13···H4xi3.0915
Cl2···H13viii2.9779H13···H4v3.3779
Cl2···H14viii3.1376H13···H12ix2.8245
Cl2···H15v3.2700H13···H14x2.8458
O1···H6v3.1444H13···H15x3.1438
O1···H7Av2.7154H14···Cl1v3.3665
O1···H10vi3.1583H14···Cl2xi3.1376
O1···H11vi3.1669H14···C6xi3.5789
O2···H2Aii2.5248H14···C16xii3.3549
O2···H2Ai2.9081H14···C17xii3.2288
O2···H5ii2.7607H14···H4xi2.7925
O2···H6iii2.5402H14···H4v3.5715
O2···H7Aiii3.3604H14···H12xii3.0781
O2···H9iii3.5379H14···H13xii2.8458
N1···H2Aii3.1678H15···Cl1v3.3698
N1···H2Ai3.5686H15···Cl2ii3.2700
N1···H10iv3.3222H15···C5v3.4109
C1···H6v3.2859H15···H13xii3.1438
C1···H9iv3.0434
C1—O1—C8112.82 (12)C19—C20—C21118.39 (13)
C10—N1—C11121.31 (12)C15—C21—C16121.33 (15)
O1—C1—C2112.00 (12)C15—C21—C20119.55 (14)
C1—C2—C3117.41 (13)C16—C21—C20119.12 (13)
C1—C2—C10119.51 (12)C10—N1—H6119.342
C3—C2—C10122.82 (14)C11—N1—H6119.346
O2—C3—C2124.70 (13)O1—C1—H1B109.210
O2—C3—C9120.73 (12)O1—C1—H2A109.215
C2—C3—C9114.49 (13)C2—C1—H1B109.214
C5—C4—C9119.64 (14)C2—C1—H2A109.212
Cl1—C5—C4119.70 (12)H1B—C1—H2A107.905
Cl1—C5—C6118.85 (11)C5—C4—H3120.177
C4—C5—C6121.43 (12)C9—C4—H3120.180
C5—C6—C7118.60 (13)C5—C6—H4120.699
Cl2—C7—C6119.28 (11)C7—C6—H4120.701
Cl2—C7—C8119.20 (10)N1—C10—H5116.499
C6—C7—C8121.52 (13)C2—C10—H5116.493
O1—C8—C7118.23 (13)N1—C11—H7A108.592
O1—C8—C9122.75 (13)N1—C11—H8B108.590
C7—C8—C9118.88 (12)C12—C11—H7A108.590
C3—C9—C4120.27 (13)C12—C11—H8B108.589
C3—C9—C8119.48 (12)H7A—C11—H8B107.556
C4—C9—C8119.90 (13)C12—C13—H9119.454
N1—C10—C2127.01 (13)C14—C13—H9119.453
N1—C11—C12114.70 (11)C13—C14—H10119.980
C11—C12—C13121.42 (13)C15—C14—H10119.986
C11—C12—C20118.60 (11)C14—C15—H11119.628
C13—C12—C20119.98 (14)C21—C15—H11119.617
C12—C13—C14121.09 (14)C17—C16—H12119.532
C13—C14—C15120.03 (13)C21—C16—H12119.524
C14—C15—C21120.75 (15)C16—C17—H13119.901
C17—C16—C21120.94 (15)C18—C17—H13119.892
C16—C17—C18120.21 (14)C17—C18—H14119.822
C17—C18—C19120.35 (13)C19—C18—H14119.826
C18—C19—C20120.98 (14)C18—C19—H15119.511
C12—C20—C19123.04 (13)C20—C19—H15119.512
C12—C20—C21118.57 (12)
C1—O1—C8—C7155.30 (11)O1—C8—C9—C4−177.29 (11)
C1—O1—C8—C9−29.15 (17)C7—C8—C9—C3171.33 (11)
C8—O1—C1—C252.17 (15)C7—C8—C9—C4−1.77 (19)
C8—O1—C1—H1B−68.9N1—C11—C12—C13−6.86 (19)
C8—O1—C1—H2A173.3N1—C11—C12—C20174.05 (11)
C10—N1—C11—C12−98.17 (16)H7A—C11—C12—C13114.8
C10—N1—C11—H7A140.2H7A—C11—C12—C20−64.3
C10—N1—C11—H8B23.5H8B—C11—C12—C13−128.5
C11—N1—C10—C2−175.34 (12)H8B—C11—C12—C2052.4
C11—N1—C10—H54.7C11—C12—C13—C14−178.41 (12)
H6—N1—C10—C24.7C11—C12—C13—H91.6
H6—N1—C10—H5−175.3C11—C12—C20—C19−2.90 (19)
H6—N1—C11—C1281.8C11—C12—C20—C21177.44 (11)
H6—N1—C11—H7A−39.8C13—C12—C20—C19178.00 (12)
H6—N1—C11—H8B−156.5C13—C12—C20—C21−1.66 (19)
O1—C1—C2—C3−44.51 (16)C20—C12—C13—C140.7 (2)
O1—C1—C2—C10141.16 (11)C20—C12—C13—H9−179.3
H1B—C1—C2—C376.6C12—C13—C14—C150.5 (3)
H1B—C1—C2—C10−97.7C12—C13—C14—H10−179.5
H2A—C1—C2—C3−165.6H9—C13—C14—C15−179.5
H2A—C1—C2—C1020.1H9—C13—C14—H100.5
C1—C2—C3—O2−171.00 (12)C13—C14—C15—C21−0.6 (3)
C1—C2—C3—C912.11 (17)C13—C14—C15—H11179.4
C1—C2—C10—N1171.75 (12)H10—C14—C15—C21179.4
C1—C2—C10—H5−8.3H10—C14—C15—H11−0.6
C3—C2—C10—N1−2.3 (3)C14—C15—C21—C16−179.85 (13)
C3—C2—C10—H5177.7C14—C15—C21—C20−0.4 (3)
C10—C2—C3—O23.1 (3)H11—C15—C21—C160.1
C10—C2—C3—C9−173.76 (12)H11—C15—C21—C20179.6
O2—C3—C9—C48.74 (19)C17—C16—C21—C15178.49 (13)
O2—C3—C9—C8−164.33 (12)C17—C16—C21—C20−0.9 (3)
C2—C3—C9—C4−174.23 (11)C21—C16—C17—C18−0.1 (3)
C2—C3—C9—C812.69 (17)C21—C16—C17—H13179.9
C5—C4—C9—C3−172.09 (11)H12—C16—C17—C18179.9
C5—C4—C9—C81.0 (2)H12—C16—C17—H13−0.1
C9—C4—C5—Cl1179.53 (11)H12—C16—C21—C15−1.5
C9—C4—C5—C60.7 (2)H12—C16—C21—C20179.1
H3—C4—C5—Cl1−0.5C16—C17—C18—C190.7 (3)
H3—C4—C5—C6−179.3C16—C17—C18—H14−179.3
H3—C4—C9—C37.9H13—C17—C18—C19−179.3
H3—C4—C9—C8−179.0H13—C17—C18—H140.7
Cl1—C5—C6—C7179.64 (9)C17—C18—C19—C20−0.3 (3)
Cl1—C5—C6—H4−0.4C17—C18—C19—H15179.7
C4—C5—C6—C7−1.6 (2)H14—C18—C19—C20179.7
C4—C5—C6—H4178.4H14—C18—C19—H15−0.3
C5—C6—C7—Cl2179.84 (11)C18—C19—C20—C12179.65 (12)
C5—C6—C7—C80.70 (19)C18—C19—C20—C21−0.7 (2)
H4—C6—C7—Cl2−0.2H15—C19—C20—C12−0.3
H4—C6—C7—C8−179.3H15—C19—C20—C21179.3
Cl2—C7—C8—O1−2.47 (17)C12—C20—C21—C151.54 (19)
Cl2—C7—C8—C9−178.20 (8)C12—C20—C21—C16−179.02 (11)
C6—C7—C8—O1176.67 (12)C19—C20—C21—C15−178.13 (12)
C6—C7—C8—C90.94 (19)C19—C20—C21—C161.30 (19)
O1—C8—C9—C3−4.19 (19)
D—H···AD—HH···AD···AD—H···A
N1—H6···O20.882.182.794 (2)126
N1—H6···O2iii0.882.543.306 (3)146
C1—H2A···O2v0.992.523.472 (3)160
C15—H11···Cg2vi0.952.773.682 (3)160
Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4–C9 ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H6⋯O20.882.182.794 (2)126
N1—H6⋯O2i 0.882.543.306 (3)146
C1—H2A⋯O2ii 0.992.523.472 (3)160
C15—H11⋯Cg2iii 0.952.773.682 (3)160

Symmetry codes: (i) ; (ii) ; (iii) .

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