Ethyl 5-(2,6-di­chloro­phenyl)-7-methyl-2-(1-naphthyl­methyl­ene)-3-oxo-2,3-di­hydro-5H-thia­zolo­[3,2-a]­pyrimidine-6-carboxyl­ate

The title compound, C₂₇H₂₀Cl₂N₂O₃S, was synthesized by the reaction of ethyl 2-mercapto-4-methyl-6-(2,6-di­chloro­phenyl)-1,6-di­hydro-pyrimidine-5-carboxyl­ate, ethyl chloro­acetate and aldehyde in acetic acid and acetic anhydride. In the mol­ecule, the thia­zolo­[3,2-a]­pyrimidine and naphthalene systems are essentially coplanar, with a dihedral angle between the combined plane and the mean plane of the benzene ring of the 2,6-di­chloro­phenyl substituent of 94.7 (4)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.040
• wR factor = 0.126
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.867     1.000
            Tmin' and Tmax expected:      0.930     0.939
            RR' =      0.875
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.94
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.50 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT410_ALERT_2_C Short Intra H...H Contact  H17    ..  H26     ..       1.96 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.939
            Tmax scaled      0.939 Tmin scaled      0.814

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Ethyl 5-(2,6-dichlorophenyl)-7-methyl-2-(1-naphthylmethylene)-3-oxo-2,3-dihydro- 5H-thiazolo[3,2-a]pyrimidine-6-carboxylate

Crystal data

C27H20Cl2N2O3S	Z = 2
Mr = 523.41	F(000) = 540
Triclinic, P1	Dx = 1.455 Mg m^−3
Hall symbol: -P 1	Melting point = 241–242 K
a = 8.974 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.126 (3) Å	Cell parameters from 826 reflections
c = 16.463 (6) Å	θ = 2.8–26.3°
α = 84.194 (6)°	µ = 0.39 mm^−1
β = 87.085 (6)°	T = 293 K
γ = 62.970 (5)°	Block, colorless
V = 1194.8 (8) Å^3	0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer	4182 independent reflections
Radiation source: fine-focus sealed tube	2795 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→9
Tmin = 0.867, Tmax = 1.000	k = −10→10
6116 measured reflections	l = −17→19

Refinement

Refinement on F^2	16 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.065P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.126	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.25 e Å^−3
4182 reflections	Δρmin = −0.23 e Å^−3
335 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.26886 (9)	0.96157 (9)	0.41771 (5)	0.0477 (2)
Cl1	0.89795 (12)	0.98332 (12)	0.20761 (6)	0.0766 (3)
Cl2	0.28046 (11)	1.03349 (12)	0.15243 (6)	0.0729 (3)
O1	0.7411 (3)	0.5357 (3)	0.11188 (15)	0.0802 (8)
O2	0.8756 (3)	0.6607 (3)	0.15878 (14)	0.0701 (7)
O3	0.5775 (3)	1.1281 (3)	0.34046 (13)	0.0580 (6)
N1	0.5020 (3)	0.9320 (3)	0.31175 (13)	0.0367 (5)
N2	0.3907 (3)	0.7412 (3)	0.30876 (15)	0.0474 (6)
C1	0.7140 (4)	1.0564 (4)	0.15223 (19)	0.0586 (9)
C2	0.6952 (6)	1.1690 (5)	0.0866 (3)	0.0814 (12)
H2	0.7785	1.2015	0.0736	0.098*
C3	0.5541 (7)	1.2328 (5)	0.0408 (3)	0.0944 (14)
H3	0.5424	1.3068	−0.0045	0.113*
C4	0.4284 (5)	1.1884 (4)	0.0611 (2)	0.0791 (11)
H4	0.3312	1.2330	0.0302	0.095*
C5	0.4484 (4)	1.0765 (4)	0.12802 (19)	0.0568 (8)
C6	0.5925 (4)	1.0034 (3)	0.17501 (17)	0.0458 (7)
C7	0.6236 (3)	0.8693 (3)	0.24490 (16)	0.0386 (6)
H7	0.7356	0.8346	0.2665	0.046*
C8	0.6178 (3)	0.7177 (3)	0.21689 (16)	0.0413 (6)
C9	0.7464 (4)	0.6275 (4)	0.15753 (18)	0.0493 (7)
C10	1.0362 (13)	0.5611 (13)	0.1179 (6)	0.069 (3)	0.61 (2)
H10A	1.0315	0.4718	0.0927	0.082*	0.61 (2)
H10B	1.1274	0.5146	0.1568	0.082*	0.61 (2)
C11	1.0597 (18)	0.6788 (11)	0.0547 (7)	0.082 (3)	0.61 (2)
H11A	1.1635	0.6218	0.0263	0.123*	0.61 (2)
H11B	1.0616	0.7675	0.0807	0.123*	0.61 (2)
H11C	0.9690	0.7226	0.0166	0.123*	0.61 (2)
C10'	0.988 (2)	0.589 (3)	0.0897 (12)	0.082 (6)	0.39 (2)
H10C	0.9270	0.6262	0.0387	0.099*	0.39 (2)
H10D	1.0398	0.4698	0.0968	0.099*	0.39 (2)
C11'	1.1185 (18)	0.651 (2)	0.0899 (14)	0.091 (5)	0.39 (2)
H11D	1.2014	0.6006	0.0489	0.136*	0.39 (2)
H11E	1.1707	0.6216	0.1425	0.136*	0.39 (2)
H11F	1.0662	0.7684	0.0785	0.136*	0.39 (2)
C12	0.5073 (3)	0.6646 (3)	0.24741 (17)	0.0437 (7)
C13	0.4940 (4)	0.5159 (4)	0.2230 (2)	0.0643 (9)
H13A	0.4055	0.5041	0.2535	0.096*	0.50
H13B	0.5978	0.4187	0.2342	0.096*	0.50
H13C	0.4704	0.5304	0.1657	0.096*	0.50
H13D	0.5769	0.4647	0.1821	0.096*	0.50
H13E	0.3846	0.5501	0.2014	0.096*	0.50
H13F	0.5120	0.4384	0.2699	0.096*	0.50
C14	0.3972 (3)	0.8632 (3)	0.33713 (16)	0.0396 (6)
C15	0.3570 (3)	1.0974 (3)	0.41762 (16)	0.0377 (6)
C16	0.4898 (3)	1.0595 (3)	0.35471 (16)	0.0395 (6)
C17	0.3212 (3)	1.2216 (3)	0.46485 (16)	0.0407 (6)
H17	0.3859	1.2771	0.4536	0.049*
C18	0.2005 (3)	1.2844 (3)	0.52992 (16)	0.0388 (6)
C19	0.0925 (4)	1.2189 (4)	0.55458 (17)	0.0511 (8)
H19	0.1016	1.1270	0.5307	0.061*
C20	−0.0297 (4)	1.2857 (4)	0.61408 (18)	0.0575 (8)
H20	−0.1014	1.2392	0.6289	0.069*
C21	−0.0444 (4)	1.4181 (4)	0.65039 (18)	0.0553 (8)
H21	−0.1269	1.4620	0.6899	0.066*
C22	0.0625 (3)	1.4910 (3)	0.62960 (16)	0.0442 (7)
C23	0.0468 (4)	1.6292 (4)	0.66767 (18)	0.0546 (8)
H23	−0.0355	1.6730	0.7072	0.066*
C24	0.1505 (4)	1.6994 (4)	0.6472 (2)	0.0620 (9)
H24	0.1394	1.7901	0.6729	0.074*
C25	0.2736 (4)	1.6347 (4)	0.5876 (2)	0.0568 (8)
H25	0.3439	1.6831	0.5736	0.068*
C26	0.2921 (4)	1.5019 (3)	0.54981 (18)	0.0494 (7)
H26	0.3755	1.4607	0.5105	0.059*
C27	0.1874 (3)	1.4245 (3)	0.56869 (16)	0.0386 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0499 (4)	0.0491 (4)	0.0584 (5)	−0.0336 (4)	0.0194 (3)	−0.0203 (4)
Cl1	0.0825 (6)	0.0978 (7)	0.0871 (7)	−0.0701 (6)	0.0355 (5)	−0.0435 (5)
Cl2	0.0597 (5)	0.0786 (6)	0.0743 (6)	−0.0276 (5)	−0.0072 (4)	0.0046 (5)
O1	0.0894 (18)	0.0921 (18)	0.0812 (17)	−0.0535 (15)	0.0279 (13)	−0.0555 (15)
O2	0.0658 (15)	0.0825 (16)	0.0832 (17)	−0.0473 (13)	0.0426 (12)	−0.0518 (14)
O3	0.0678 (14)	0.0641 (13)	0.0698 (14)	−0.0515 (12)	0.0312 (11)	−0.0341 (11)
N1	0.0388 (12)	0.0366 (12)	0.0415 (13)	−0.0221 (10)	0.0104 (10)	−0.0141 (10)
N2	0.0500 (14)	0.0431 (13)	0.0613 (16)	−0.0304 (12)	0.0123 (12)	−0.0176 (12)
C1	0.081 (2)	0.0528 (19)	0.0581 (19)	−0.0432 (18)	0.0309 (17)	−0.0253 (16)
C2	0.118 (4)	0.069 (2)	0.078 (3)	−0.061 (3)	0.041 (3)	−0.019 (2)
C3	0.141 (4)	0.066 (3)	0.070 (3)	−0.047 (3)	0.033 (3)	0.005 (2)
C4	0.100 (3)	0.059 (2)	0.060 (2)	−0.023 (2)	0.010 (2)	0.0009 (19)
C5	0.072 (2)	0.0448 (17)	0.0505 (19)	−0.0242 (16)	0.0133 (17)	−0.0071 (15)
C6	0.0600 (18)	0.0383 (15)	0.0455 (16)	−0.0270 (14)	0.0171 (14)	−0.0159 (13)
C7	0.0407 (15)	0.0362 (14)	0.0450 (16)	−0.0216 (12)	0.0098 (12)	−0.0138 (12)
C8	0.0448 (16)	0.0377 (15)	0.0456 (16)	−0.0208 (13)	0.0043 (13)	−0.0137 (13)
C9	0.0603 (19)	0.0464 (17)	0.0465 (17)	−0.0276 (15)	0.0095 (14)	−0.0147 (14)
C10	0.081 (6)	0.081 (6)	0.061 (5)	−0.047 (5)	0.027 (4)	−0.041 (5)
C11	0.093 (6)	0.085 (5)	0.074 (5)	−0.044 (5)	0.034 (5)	−0.032 (4)
C10'	0.057 (8)	0.125 (13)	0.073 (11)	−0.043 (9)	0.044 (8)	−0.060 (11)
C11'	0.061 (7)	0.110 (8)	0.090 (9)	−0.031 (6)	0.021 (6)	−0.011 (7)
C12	0.0485 (17)	0.0375 (15)	0.0508 (17)	−0.0228 (13)	0.0027 (13)	−0.0132 (13)
C13	0.077 (2)	0.058 (2)	0.079 (2)	−0.0454 (18)	0.0154 (18)	−0.0301 (18)
C14	0.0369 (15)	0.0391 (15)	0.0479 (16)	−0.0216 (13)	0.0037 (12)	−0.0060 (13)
C15	0.0372 (14)	0.0410 (15)	0.0416 (15)	−0.0231 (12)	0.0067 (12)	−0.0088 (12)
C16	0.0420 (15)	0.0382 (15)	0.0454 (16)	−0.0230 (13)	0.0066 (13)	−0.0135 (13)
C17	0.0393 (15)	0.0446 (16)	0.0470 (16)	−0.0258 (13)	0.0051 (12)	−0.0105 (13)
C18	0.0386 (15)	0.0456 (16)	0.0390 (15)	−0.0237 (13)	0.0045 (12)	−0.0123 (13)
C19	0.0570 (19)	0.0625 (19)	0.0517 (18)	−0.0406 (17)	0.0106 (15)	−0.0197 (15)
C20	0.0599 (19)	0.084 (2)	0.0507 (18)	−0.0509 (19)	0.0171 (15)	−0.0198 (17)
C21	0.0456 (17)	0.080 (2)	0.0435 (17)	−0.0295 (17)	0.0151 (14)	−0.0215 (16)
C22	0.0390 (15)	0.0515 (17)	0.0418 (16)	−0.0183 (14)	0.0010 (13)	−0.0140 (14)
C23	0.0527 (19)	0.0556 (19)	0.0487 (18)	−0.0160 (16)	0.0060 (15)	−0.0207 (15)
C24	0.072 (2)	0.0516 (19)	0.067 (2)	−0.0275 (18)	−0.0043 (18)	−0.0251 (17)
C25	0.062 (2)	0.0519 (18)	0.068 (2)	−0.0331 (16)	0.0059 (17)	−0.0200 (16)
C26	0.0498 (17)	0.0513 (18)	0.0546 (18)	−0.0274 (15)	0.0100 (14)	−0.0199 (15)
C27	0.0362 (15)	0.0417 (15)	0.0396 (15)	−0.0180 (13)	0.0003 (12)	−0.0097 (12)

Geometric parameters (Å, º)

S1—C14	1.743 (3)	C10'—H10C	0.9700
S1—C15	1.747 (3)	C10'—H10D	0.9700
Cl1—C1	1.741 (4)	C11'—H11D	0.9600
Cl2—C5	1.742 (4)	C11'—H11E	0.9600
O1—C9	1.198 (3)	C11'—H11F	0.9600
O2—C9	1.327 (3)	C12—C13	1.510 (4)
O2—C10'	1.474 (9)	C13—H13A	0.9600
O2—C10	1.480 (7)	C13—H13B	0.9600
O3—C16	1.211 (3)	C13—H13C	0.9600
N1—C14	1.377 (3)	C13—H13D	0.9600
N1—C16	1.381 (3)	C13—H13E	0.9600
N1—C7	1.472 (3)	C13—H13F	0.9600
N2—C14	1.276 (3)	C15—C17	1.347 (4)
N2—C12	1.405 (3)	C15—C16	1.478 (4)
C1—C2	1.374 (5)	C17—C18	1.446 (4)
C1—C6	1.402 (4)	C17—H17	0.9300
C2—C3	1.360 (6)	C18—C19	1.378 (4)
C2—H2	0.9300	C18—C27	1.441 (3)
C3—C4	1.378 (6)	C19—C20	1.392 (4)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.384 (5)	C20—C21	1.352 (4)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.388 (4)	C21—C22	1.407 (4)
C6—C7	1.529 (4)	C21—H21	0.9300
C7—C8	1.526 (3)	C22—C23	1.412 (4)
C7—H7	0.9800	C22—C27	1.421 (4)
C8—C12	1.344 (4)	C23—C24	1.363 (4)
C8—C9	1.466 (4)	C23—H23	0.9300
C10—C11	1.496 (8)	C24—C25	1.395 (4)
C10—H10A	0.9700	C24—H24	0.9300
C10—H10B	0.9700	C25—C26	1.358 (4)
C11—H11A	0.9600	C25—H25	0.9300
C11—H11B	0.9600	C26—C27	1.416 (4)
C11—H11C	0.9600	C26—H26	0.9300
C10'—C11'	1.507 (10)
C14—S1—C15	91.74 (12)	C12—C13—H13A	109.5
C9—O2—C10'	109.2 (6)	C12—C13—H13B	109.5
C9—O2—C10	122.0 (6)	H13A—C13—H13B	109.5
C14—N1—C16	115.8 (2)	C12—C13—H13C	109.5
C14—N1—C7	121.9 (2)	H13A—C13—H13C	109.5
C16—N1—C7	122.2 (2)	H13B—C13—H13C	109.5
C14—N2—C12	116.6 (2)	C12—C13—H13D	109.5
C2—C1—C6	122.7 (4)	H13A—C13—H13D	141.1
C2—C1—Cl1	116.3 (3)	H13B—C13—H13D	56.3
C6—C1—Cl1	121.0 (3)	H13C—C13—H13D	56.3
C3—C2—C1	119.6 (4)	C12—C13—H13E	109.5
C3—C2—H2	120.2	H13A—C13—H13E	56.3
C1—C2—H2	120.2	H13B—C13—H13E	141.1
C2—C3—C4	120.4 (4)	H13C—C13—H13E	56.3
C2—C3—H3	119.8	H13D—C13—H13E	109.5
C4—C3—H3	119.8	C12—C13—H13F	109.5
C3—C4—C5	119.1 (4)	H13A—C13—H13F	56.3
C3—C4—H4	120.4	H13B—C13—H13F	56.3
C5—C4—H4	120.4	H13C—C13—H13F	141.1
C4—C5—C6	122.7 (3)	H13D—C13—H13F	109.5
C4—C5—Cl2	116.5 (3)	H13E—C13—H13F	109.5
C6—C5—Cl2	120.8 (2)	N2—C14—N1	126.9 (3)
C5—C6—C1	115.3 (3)	N2—C14—S1	121.4 (2)
C5—C6—C7	123.7 (3)	N1—C14—S1	111.64 (18)
C1—C6—C7	121.0 (3)	C17—C15—C16	120.1 (2)
N1—C7—C8	108.9 (2)	C17—C15—S1	129.8 (2)
N1—C7—C6	111.4 (2)	C16—C15—S1	110.15 (18)
C8—C7—C6	112.4 (2)	O3—C16—N1	122.9 (2)
N1—C7—H7	108.0	O3—C16—C15	126.5 (2)
C8—C7—H7	108.0	N1—C16—C15	110.6 (2)
C6—C7—H7	108.0	C15—C17—C18	131.7 (3)
C12—C8—C9	121.7 (2)	C15—C17—H17	114.1
C12—C8—C7	122.4 (2)	C18—C17—H17	114.1
C9—C8—C7	115.8 (2)	C19—C18—C27	118.4 (2)
O1—C9—O2	122.0 (3)	C19—C18—C17	122.4 (2)
O1—C9—C8	126.8 (3)	C27—C18—C17	119.2 (2)
O2—C9—C8	111.3 (2)	C18—C19—C20	122.1 (3)
O2—C10—C11	105.3 (7)	C18—C19—H19	118.9
O2—C10—H10A	110.7	C20—C19—H19	118.9
C11—C10—H10A	110.7	C21—C20—C19	120.2 (3)
O2—C10—H10B	110.7	C21—C20—H20	119.9
C11—C10—H10B	110.7	C19—C20—H20	119.9
H10A—C10—H10B	108.8	C20—C21—C22	121.3 (3)
C10—C11—H11A	109.5	C20—C21—H21	119.3
C10—C11—H11B	109.5	C22—C21—H21	119.3
H11A—C11—H11B	109.5	C21—C22—C23	121.2 (3)
C10—C11—H11C	109.5	C21—C22—C27	119.2 (2)
H11A—C11—H11C	109.5	C23—C22—C27	119.7 (3)
H11B—C11—H11C	109.5	C24—C23—C22	120.9 (3)
O2—C10'—C11'	105.5 (10)	C24—C23—H23	119.5
O2—C10'—H10C	110.6	C22—C23—H23	119.5
C11'—C10'—H10C	110.6	C23—C24—C25	119.7 (3)
O2—C10'—H10D	110.6	C23—C24—H24	120.1
C11'—C10'—H10D	110.6	C25—C24—H24	120.1
H10C—C10'—H10D	108.8	C26—C25—C24	120.9 (3)
C10'—C11'—H11D	109.5	C26—C25—H25	119.6
C10'—C11'—H11E	109.5	C24—C25—H25	119.6
H11D—C11'—H11E	109.5	C25—C26—C27	121.7 (3)
C10'—C11'—H11F	109.5	C25—C26—H26	119.2
H11D—C11'—H11F	109.5	C27—C26—H26	119.2
H11E—C11'—H11F	109.5	C26—C27—C22	117.1 (2)
C8—C12—N2	123.0 (2)	C26—C27—C18	124.0 (2)
C8—C12—C13	125.5 (3)	C22—C27—C18	118.9 (2)
N2—C12—C13	111.4 (2)
C6—C1—C2—C3	−0.3 (5)	C12—N2—C14—N1	2.8 (4)
Cl1—C1—C2—C3	−179.4 (3)	C12—N2—C14—S1	−176.0 (2)
C1—C2—C3—C4	1.7 (6)	C16—N1—C14—N2	−177.3 (3)
C2—C3—C4—C5	−0.8 (6)	C7—N1—C14—N2	0.5 (4)
C3—C4—C5—C6	−1.6 (5)	C16—N1—C14—S1	1.6 (3)
C3—C4—C5—Cl2	177.3 (3)	C7—N1—C14—S1	179.41 (19)
C4—C5—C6—C1	2.8 (4)	C15—S1—C14—N2	178.9 (2)
Cl2—C5—C6—C1	−176.0 (2)	C15—S1—C14—N1	−0.1 (2)
C4—C5—C6—C7	−174.9 (3)	C14—S1—C15—C17	179.1 (3)
Cl2—C5—C6—C7	6.4 (4)	C14—S1—C15—C16	−1.3 (2)
C2—C1—C6—C5	−1.9 (4)	C14—N1—C16—O3	177.9 (3)
Cl1—C1—C6—C5	177.2 (2)	C7—N1—C16—O3	0.1 (4)
C2—C1—C6—C7	175.8 (3)	C14—N1—C16—C15	−2.5 (3)
Cl1—C1—C6—C7	−5.0 (4)	C7—N1—C16—C15	179.6 (2)
C14—N1—C7—C8	−3.8 (3)	C17—C15—C16—O3	1.5 (4)
C16—N1—C7—C8	173.9 (2)	S1—C15—C16—O3	−178.1 (2)
C14—N1—C7—C6	120.7 (3)	C17—C15—C16—N1	−178.0 (2)
C16—N1—C7—C6	−61.6 (3)	S1—C15—C16—N1	2.4 (3)
C5—C6—C7—N1	−64.2 (3)	C16—C15—C17—C18	−179.8 (3)
C1—C6—C7—N1	118.3 (3)	S1—C15—C17—C18	−0.3 (5)
C5—C6—C7—C8	58.3 (3)	C15—C17—C18—C19	−0.7 (5)
C1—C6—C7—C8	−119.2 (3)	C15—C17—C18—C27	−178.3 (3)
N1—C7—C8—C12	4.3 (4)	C27—C18—C19—C20	1.4 (4)
C6—C7—C8—C12	−119.7 (3)	C17—C18—C19—C20	−176.3 (3)
N1—C7—C8—C9	−172.6 (2)	C18—C19—C20—C21	−0.7 (5)
C6—C7—C8—C9	63.5 (3)	C19—C20—C21—C22	−0.3 (5)
C10'—O2—C9—O1	8.4 (14)	C20—C21—C22—C23	−180.0 (3)
C10—O2—C9—O1	−13.7 (7)	C20—C21—C22—C27	0.5 (5)
C10'—O2—C9—C8	−170.9 (13)	C21—C22—C23—C24	−179.9 (3)
C10—O2—C9—C8	167.0 (5)	C27—C22—C23—C24	−0.4 (4)
C12—C8—C9—O1	24.4 (5)	C22—C23—C24—C25	0.3 (5)
C7—C8—C9—O1	−158.8 (3)	C23—C24—C25—C26	−0.3 (5)
C12—C8—C9—O2	−156.3 (3)	C24—C25—C26—C27	0.4 (5)
C7—C8—C9—O2	20.5 (4)	C25—C26—C27—C22	−0.5 (4)
C9—O2—C10—C11	118.5 (11)	C25—C26—C27—C18	179.4 (3)
C10'—O2—C10—C11	56 (3)	C21—C22—C27—C26	180.0 (3)
C9—O2—C10'—C11'	173.3 (18)	C23—C22—C27—C26	0.5 (4)
C10—O2—C10'—C11'	−60 (2)	C21—C22—C27—C18	0.1 (4)
C9—C8—C12—N2	175.1 (3)	C23—C22—C27—C18	−179.4 (2)
C7—C8—C12—N2	−1.5 (4)	C19—C18—C27—C26	179.1 (3)
C9—C8—C12—C13	−3.3 (5)	C17—C18—C27—C26	−3.1 (4)
C7—C8—C12—C13	−179.9 (3)	C19—C18—C27—C22	−1.0 (4)
C14—N2—C12—C8	−2.3 (4)	C17—C18—C27—C22	176.7 (2)
C14—N2—C12—C13	176.3 (3)