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The title compound, β-C16H12ClN3OS, crystallizes with two independent mol­ecules in the asymmetric unit, both of which show a similar twisted conformation. It is polymorphic with α-C16H12ClN3OS [Çaliskan, Daĝ, Yüksektepe, Cukurovali & Murat (2006). Acta Cryst. E62, o4889–o4890]; both forms crystallize in the same space group. The two independent mol­ecules in β-C16H12ClN3OS are linked into dimers by pairs of N—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045028/hb2155sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045028/hb2155Isup2.hkl
Contains datablock I

CCDC reference: 630543

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.123
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

4-Chloro-2-[(4-phenylthiazol-2-yl)hydrazonomethyl]phenol top
Crystal data top
C16H12ClN3OSF(000) = 1360
Mr = 329.80Dx = 1.427 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 35261 reflections
a = 10.8757 (4) Åθ = 1.2–25.1°
b = 8.2302 (5) ŵ = 0.39 mm1
c = 34.9645 (13) ÅT = 296 K
β = 101.144 (3)°Prism, pale yellow
V = 3070.6 (2) Å30.60 × 0.51 × 0.31 mm
Z = 8
Data collection top
Stoe IPDS-2
diffractometer
5398 independent reflections
Radiation source: fine-focus sealed tube3603 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
Detector resolution: 6.67 pixels mm-1θmax = 25.0°, θmin = 1.9°
ω scansh = 1212
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 99
Tmin = 0.765, Tmax = 0.904l = 4141
36136 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0772P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
5398 reflectionsΔρmax = 0.75 e Å3
398 parametersΔρmin = 0.70 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0204 (13)
Special details top

Experimental. Characteristic IR bands: 3280 cm-1 ν(O—H), 3120 cm-1 ν (N—H), 1614 cm-1 ν(C=N azomethine), 1604 cm-1 ν(C=N thiazole), 676 cm-1 ν(C—S—C thiazole). Characteristic 1H NMR shifts (CDCl3,δ, p.p.m.): 6.96 (s, 1H, thiazole), 7.20–7.89 (m, 8H, aromatics), 8.31 (s, 1H, azomethine), 10.40 (s,1H, –NH–), 12.20 (s, 1H, –OH)·Characteristic 13 C NMR shifts (CDCl3,δ, p.p.m.): 125.05 (C1),156.41 (C2), 119.74 (C3), 131.57 (C4), 123.93(C5), 130.39 (C6),139.38 (C7), 169.69 (C8), 105.31 (C9), 152.2 (C10), 136.22 (C11),126.69 (C12), 127.33 (C13), 129.37 (C14).

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*/Ueq
Cl10.48293 (8)0.31249 (13)0.25553 (2)0.1076 (3)
Cl21.02569 (7)0.03209 (12)0.237484 (19)0.1012 (3)
S10.40166 (6)0.19980 (13)0.008081 (19)0.0956 (3)
S21.09624 (5)0.23121 (10)0.003219 (19)0.0780 (2)
O10.27872 (14)0.2209 (2)0.11398 (5)0.0804 (5)
H10.33360.22710.09430.121*
O21.20688 (14)0.0333 (2)0.09098 (5)0.0789 (5)
H2B1.15050.05910.07290.118*
N10.62516 (16)0.2710 (3)0.02769 (5)0.0652 (5)
N20.59798 (18)0.2772 (3)0.04051 (5)0.0813 (7)
H2A0.67550.29670.04070.098*
N30.51048 (17)0.2654 (3)0.07403 (5)0.0701 (5)
N40.87225 (16)0.3234 (2)0.03283 (5)0.0598 (5)
N50.89425 (17)0.2068 (3)0.02955 (5)0.0696 (5)
H5A0.81600.21340.03050.084*
N60.98007 (16)0.1451 (2)0.05974 (5)0.0625 (5)
C10.6116 (2)0.2498 (3)0.09768 (6)0.0626 (6)
C20.5679 (2)0.1542 (3)0.12479 (7)0.0751 (7)
H20.50280.08150.11640.090*
C30.6190 (3)0.1650 (4)0.16386 (7)0.0856 (8)
H30.58840.09990.18160.103*
C40.7143 (3)0.2706 (4)0.17657 (8)0.0903 (9)
H40.74830.27870.20300.108*
C50.7603 (3)0.3658 (4)0.15005 (9)0.0901 (8)
H50.82610.43720.15870.108*
C60.7090 (2)0.3556 (3)0.11072 (8)0.0764 (7)
H60.74030.42030.09300.092*
C70.5539 (2)0.2376 (3)0.05605 (6)0.0652 (6)
C80.4336 (2)0.1974 (4)0.04172 (7)0.0864 (8)
H80.37530.17160.05700.104*
C90.5555 (2)0.2564 (3)0.00672 (7)0.0690 (6)
C100.5470 (2)0.2799 (3)0.10660 (6)0.0666 (6)
H100.63180.29420.10660.080*
C110.4586 (2)0.2743 (3)0.14335 (6)0.0610 (5)
C120.3300 (2)0.2452 (3)0.14614 (7)0.0635 (6)
C130.2512 (2)0.2399 (3)0.18198 (7)0.0730 (6)
H130.16600.22140.18340.088*
C140.2967 (2)0.2615 (3)0.21569 (7)0.0748 (7)
H140.24290.25750.23980.090*
C150.4236 (2)0.2894 (3)0.21321 (7)0.0716 (6)
C160.5031 (2)0.2968 (3)0.17782 (6)0.0663 (6)
H160.58780.31700.17670.080*
C170.8912 (2)0.4328 (3)0.09760 (6)0.0615 (5)
C180.7902 (2)0.5375 (3)0.10074 (7)0.0729 (6)
H180.75720.56200.07880.087*
C190.7379 (3)0.6058 (4)0.13615 (9)0.0892 (8)
H190.66960.67530.13800.107*
C200.7863 (3)0.5716 (4)0.16881 (9)0.0970 (9)
H200.75070.61750.19270.116*
C210.8868 (3)0.4701 (4)0.16594 (8)0.0936 (9)
H210.92000.44750.18800.112*
C220.9394 (3)0.4008 (3)0.13080 (7)0.0777 (7)
H221.00800.33190.12930.093*
C230.94659 (19)0.3567 (3)0.06019 (6)0.0592 (5)
C241.0675 (2)0.3143 (4)0.04898 (7)0.0770 (7)
H241.12810.32830.06420.092*
C250.93961 (19)0.2572 (3)0.00200 (6)0.0584 (5)
C260.94424 (19)0.1056 (3)0.09130 (6)0.0635 (6)
H260.85980.11230.09260.076*
C271.03403 (19)0.0506 (3)0.12507 (6)0.0588 (5)
C280.9942 (2)0.0333 (3)0.16048 (6)0.0660 (6)
H280.91080.05240.16170.079*
C291.0778 (2)0.0118 (3)0.19357 (6)0.0691 (6)
C301.2017 (2)0.0399 (3)0.19244 (7)0.0763 (7)
H301.25760.07050.21490.092*
C311.2419 (2)0.0225 (3)0.15797 (8)0.0749 (7)
H311.32590.03960.15730.090*
C321.1601 (2)0.0201 (3)0.12418 (7)0.0636 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1008 (5)0.1665 (8)0.0589 (4)0.0036 (5)0.0234 (4)0.0175 (4)
Cl20.0955 (5)0.1498 (7)0.0565 (4)0.0171 (5)0.0097 (3)0.0076 (4)
S10.0442 (3)0.1791 (8)0.0633 (4)0.0053 (4)0.0097 (3)0.0085 (4)
S20.0468 (3)0.1183 (6)0.0699 (4)0.0089 (3)0.0135 (3)0.0166 (4)
O10.0527 (9)0.1257 (15)0.0641 (10)0.0042 (9)0.0146 (7)0.0056 (9)
O20.0577 (9)0.1095 (14)0.0718 (10)0.0092 (9)0.0184 (8)0.0069 (9)
N10.0500 (10)0.0940 (14)0.0522 (10)0.0007 (9)0.0112 (8)0.0053 (9)
N20.0477 (10)0.142 (2)0.0530 (11)0.0086 (11)0.0076 (8)0.0105 (12)
N30.0500 (10)0.1067 (16)0.0523 (10)0.0003 (10)0.0063 (8)0.0065 (10)
N40.0490 (9)0.0764 (12)0.0545 (10)0.0013 (9)0.0114 (8)0.0043 (9)
N50.0467 (10)0.1040 (15)0.0584 (11)0.0050 (10)0.0105 (8)0.0151 (10)
N60.0485 (9)0.0810 (13)0.0560 (10)0.0019 (9)0.0049 (8)0.0067 (9)
C10.0562 (12)0.0764 (15)0.0578 (12)0.0085 (11)0.0173 (10)0.0024 (11)
C20.0749 (15)0.0945 (18)0.0597 (14)0.0037 (14)0.0228 (12)0.0029 (13)
C30.098 (2)0.106 (2)0.0576 (15)0.0049 (17)0.0258 (14)0.0006 (14)
C40.100 (2)0.110 (2)0.0581 (15)0.0161 (19)0.0106 (14)0.0133 (15)
C50.0869 (18)0.095 (2)0.083 (2)0.0042 (16)0.0045 (15)0.0233 (16)
C60.0763 (16)0.0806 (17)0.0738 (16)0.0033 (13)0.0183 (13)0.0010 (13)
C70.0500 (12)0.0915 (17)0.0562 (12)0.0034 (11)0.0158 (10)0.0028 (11)
C80.0508 (13)0.146 (3)0.0658 (15)0.0008 (14)0.0200 (11)0.0093 (16)
C90.0468 (11)0.1028 (19)0.0575 (13)0.0045 (12)0.0108 (10)0.0084 (13)
C100.0493 (12)0.0920 (17)0.0591 (13)0.0039 (11)0.0121 (10)0.0049 (12)
C110.0527 (12)0.0753 (15)0.0546 (12)0.0009 (11)0.0089 (9)0.0045 (10)
C120.0529 (12)0.0787 (15)0.0598 (13)0.0017 (11)0.0132 (10)0.0015 (11)
C130.0545 (13)0.0946 (18)0.0668 (15)0.0002 (12)0.0038 (11)0.0007 (13)
C140.0708 (15)0.0895 (18)0.0596 (14)0.0047 (13)0.0014 (11)0.0009 (12)
C150.0744 (15)0.0858 (17)0.0552 (13)0.0060 (13)0.0140 (11)0.0095 (12)
C160.0581 (13)0.0833 (16)0.0586 (13)0.0009 (12)0.0142 (10)0.0074 (11)
C170.0594 (12)0.0664 (14)0.0597 (13)0.0074 (11)0.0139 (10)0.0047 (11)
C180.0694 (14)0.0745 (16)0.0743 (15)0.0001 (12)0.0125 (12)0.0046 (12)
C190.0804 (17)0.0830 (18)0.097 (2)0.0015 (15)0.0010 (15)0.0217 (16)
C200.107 (2)0.101 (2)0.0775 (19)0.0149 (19)0.0022 (16)0.0299 (17)
C210.112 (2)0.106 (2)0.0653 (16)0.012 (2)0.0218 (15)0.0155 (15)
C220.0837 (16)0.0845 (17)0.0681 (15)0.0011 (14)0.0229 (12)0.0083 (13)
C230.0517 (12)0.0686 (14)0.0587 (13)0.0013 (10)0.0139 (9)0.0006 (10)
C240.0547 (13)0.108 (2)0.0728 (15)0.0022 (13)0.0227 (11)0.0146 (14)
C250.0456 (11)0.0741 (14)0.0553 (12)0.0003 (10)0.0096 (9)0.0015 (10)
C260.0486 (11)0.0836 (16)0.0578 (13)0.0002 (11)0.0090 (9)0.0053 (11)
C270.0533 (11)0.0661 (13)0.0562 (12)0.0024 (10)0.0082 (9)0.0020 (10)
C280.0572 (12)0.0793 (16)0.0611 (13)0.0010 (11)0.0106 (10)0.0039 (11)
C290.0710 (15)0.0798 (16)0.0536 (13)0.0084 (12)0.0047 (11)0.0031 (11)
C300.0687 (15)0.0857 (18)0.0671 (15)0.0026 (13)0.0052 (12)0.0096 (13)
C310.0554 (13)0.0857 (17)0.0799 (16)0.0058 (12)0.0041 (12)0.0095 (13)
C320.0549 (12)0.0704 (15)0.0658 (14)0.0007 (10)0.0123 (10)0.0029 (11)
Geometric parameters (Å, º) top
Cl1—C151.735 (2)C10—C111.449 (3)
Cl2—C291.744 (2)C10—H100.9300
S1—C81.709 (3)C11—C161.395 (3)
S1—C91.729 (2)C11—C121.403 (3)
S2—C241.712 (3)C12—C131.376 (3)
S2—C251.725 (2)C13—C141.375 (3)
O1—C121.363 (3)C13—H130.9300
O1—H10.8200C14—C151.386 (3)
O2—C321.359 (3)C14—H140.9300
O2—H2B0.8200C15—C161.367 (3)
N1—C91.298 (3)C16—H160.9300
N1—C71.398 (3)C17—C181.384 (3)
N2—C91.360 (3)C17—C221.388 (3)
N2—N31.363 (3)C17—C231.470 (3)
N2—H2A0.8600C18—C191.378 (4)
N3—C101.282 (3)C18—H180.9300
N4—C251.300 (3)C19—C201.376 (4)
N4—C231.394 (3)C19—H190.9300
N5—C251.358 (3)C20—C211.364 (4)
N5—N61.365 (2)C20—H200.9300
N5—H5A0.8600C21—C221.375 (4)
N6—C261.281 (3)C21—H210.9300
C1—C61.379 (4)C22—H220.9300
C1—C21.385 (3)C23—C241.344 (3)
C1—C71.473 (3)C24—H240.9300
C2—C31.374 (4)C26—C271.451 (3)
C2—H20.9300C26—H260.9300
C3—C41.360 (4)C27—C281.396 (3)
C3—H30.9300C27—C321.400 (3)
C4—C51.379 (4)C28—C291.377 (3)
C4—H40.9300C28—H280.9300
C5—C61.383 (4)C29—C301.376 (3)
C5—H50.9300C30—C311.366 (3)
C6—H60.9300C30—H300.9300
C7—C81.349 (3)C31—C321.380 (3)
C8—H80.9300C31—H310.9300
C8—S1—C988.29 (11)C15—C14—H14120.4
C24—S2—C2588.34 (11)C16—C15—C14120.8 (2)
C12—O1—H1109.5C16—C15—Cl1119.53 (19)
C32—O2—H2B109.5C14—C15—Cl1119.67 (19)
C9—N1—C7109.58 (18)C15—C16—C11120.8 (2)
C9—N2—N3116.11 (18)C15—C16—H16119.6
C9—N2—H2A121.9C11—C16—H16119.6
N3—N2—H2A121.9C18—C17—C22118.3 (2)
C10—N3—N2118.20 (19)C18—C17—C23121.2 (2)
C25—N4—C23110.05 (17)C22—C17—C23120.5 (2)
C25—N5—N6116.14 (17)C19—C18—C17120.6 (2)
C25—N5—H5A121.9C19—C18—H18119.7
N6—N5—H5A121.9C17—C18—H18119.7
C26—N6—N5118.96 (17)C20—C19—C18120.3 (3)
C6—C1—C2118.4 (2)C20—C19—H19119.8
C6—C1—C7121.5 (2)C18—C19—H19119.8
C2—C1—C7120.1 (2)C21—C20—C19119.6 (3)
C3—C2—C1121.1 (3)C21—C20—H20120.2
C3—C2—H2119.4C19—C20—H20120.2
C1—C2—H2119.4C20—C21—C22120.6 (3)
C4—C3—C2120.2 (3)C20—C21—H21119.7
C4—C3—H3119.9C22—C21—H21119.7
C2—C3—H3119.9C21—C22—C17120.6 (3)
C3—C4—C5119.7 (3)C21—C22—H22119.7
C3—C4—H4120.1C17—C22—H22119.7
C5—C4—H4120.1C24—C23—N4114.4 (2)
C4—C5—C6120.3 (3)C24—C23—C17125.4 (2)
C4—C5—H5119.8N4—C23—C17120.14 (18)
C6—C5—H5119.8C23—C24—S2111.56 (17)
C1—C6—C5120.2 (3)C23—C24—H24124.2
C1—C6—H6119.9S2—C24—H24124.2
C5—C6—H6119.9N4—C25—N5124.53 (19)
C8—C7—N1114.6 (2)N4—C25—S2115.62 (15)
C8—C7—C1125.5 (2)N5—C25—S2119.85 (16)
N1—C7—C1119.91 (19)N6—C26—C27120.72 (19)
C7—C8—S1111.53 (18)N6—C26—H26119.6
C7—C8—H8124.2C27—C26—H26119.6
S1—C8—H8124.2C28—C27—C32118.30 (19)
N1—C9—N2123.9 (2)C28—C27—C26118.57 (19)
N1—C9—S1116.04 (16)C32—C27—C26123.08 (19)
N2—C9—S1119.97 (17)C29—C28—C27120.4 (2)
N3—C10—C11121.2 (2)C29—C28—H28119.8
N3—C10—H10119.4C27—C28—H28119.8
C11—C10—H10119.4C30—C29—C28120.8 (2)
C16—C11—C12118.0 (2)C30—C29—Cl2119.73 (18)
C16—C11—C10118.7 (2)C28—C29—Cl2119.46 (18)
C12—C11—C10123.26 (19)C31—C30—C29119.3 (2)
O1—C12—C13117.7 (2)C31—C30—H30120.3
O1—C12—C11121.9 (2)C29—C30—H30120.3
C13—C12—C11120.4 (2)C30—C31—C32121.3 (2)
C14—C13—C12120.8 (2)C30—C31—H31119.4
C14—C13—H13119.6C32—C31—H31119.4
C12—C13—H13119.6O2—C32—C31117.8 (2)
C13—C14—C15119.2 (2)O2—C32—C27122.32 (19)
C13—C14—H14120.4C31—C32—C27119.9 (2)
C9—N2—N3—C10178.1 (2)C10—C11—C16—C15178.7 (2)
C25—N5—N6—C26175.4 (2)C22—C17—C18—C191.0 (4)
C6—C1—C2—C30.6 (4)C23—C17—C18—C19178.9 (2)
C7—C1—C2—C3179.1 (2)C17—C18—C19—C200.5 (4)
C1—C2—C3—C40.0 (4)C18—C19—C20—C210.3 (4)
C2—C3—C4—C50.7 (4)C19—C20—C21—C220.5 (5)
C3—C4—C5—C60.8 (4)C20—C21—C22—C170.1 (4)
C2—C1—C6—C50.5 (4)C18—C17—C22—C210.8 (4)
C7—C1—C6—C5179.2 (2)C23—C17—C22—C21179.1 (2)
C4—C5—C6—C10.2 (4)C25—N4—C23—C240.1 (3)
C9—N1—C7—C80.7 (3)C25—N4—C23—C17179.7 (2)
C9—N1—C7—C1178.6 (2)C18—C17—C23—C24149.7 (3)
C6—C1—C7—C8150.2 (3)C22—C17—C23—C2430.3 (4)
C2—C1—C7—C829.5 (4)C18—C17—C23—N430.0 (3)
C6—C1—C7—N129.0 (3)C22—C17—C23—N4149.9 (2)
C2—C1—C7—N1151.3 (2)N4—C23—C24—S20.5 (3)
N1—C7—C8—S10.3 (3)C17—C23—C24—S2179.29 (19)
C1—C7—C8—S1179.0 (2)C25—S2—C24—C230.6 (2)
C9—S1—C8—C70.1 (2)C23—N4—C25—N5178.4 (2)
C7—N1—C9—N2178.4 (2)C23—N4—C25—S20.4 (2)
C7—N1—C9—S10.8 (3)N6—N5—C25—N4177.9 (2)
N3—N2—C9—N1176.8 (2)N6—N5—C25—S23.4 (3)
N3—N2—C9—S15.7 (3)C24—S2—C25—N40.6 (2)
C8—S1—C9—N10.5 (2)C24—S2—C25—N5178.3 (2)
C8—S1—C9—N2178.2 (2)N5—N6—C26—C27175.5 (2)
N2—N3—C10—C11177.8 (2)N6—C26—C27—C28170.1 (2)
N3—C10—C11—C16177.6 (2)N6—C26—C27—C327.3 (4)
N3—C10—C11—C123.2 (4)C32—C27—C28—C290.4 (4)
C16—C11—C12—O1179.6 (2)C26—C27—C28—C29177.2 (2)
C10—C11—C12—O10.4 (4)C27—C28—C29—C300.3 (4)
C16—C11—C12—C130.2 (4)C27—C28—C29—Cl2179.86 (19)
C10—C11—C12—C13179.4 (2)C28—C29—C30—C310.1 (4)
O1—C12—C13—C14179.3 (2)Cl2—C29—C30—C31179.5 (2)
C11—C12—C13—C140.5 (4)C29—C30—C31—C321.1 (4)
C12—C13—C14—C150.2 (4)C30—C31—C32—O2179.3 (2)
C13—C14—C15—C160.5 (4)C30—C31—C32—C271.8 (4)
C13—C14—C15—Cl1178.6 (2)C28—C27—C32—O2179.8 (2)
C14—C15—C16—C110.8 (4)C26—C27—C32—O22.8 (4)
Cl1—C15—C16—C11178.25 (19)C28—C27—C32—C311.4 (3)
C12—C11—C16—C150.5 (4)C26—C27—C32—C31176.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N40.862.112.967 (3)171
N5—H5A···N10.862.112.962 (3)170
O1—H1···N30.821.942.661 (2)146
O2—H2B···N60.821.952.661 (2)144
 

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