4′-(4-Chloro­phenyl)-1′-methyl-4′′,5′′,6′′,7′′-tetra­hydro-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2′′-(thia­zolo­[3,2-a]­pyrimidine)-2(3H),3′′(2′′H)-dione

Li, X.-F.; Feng, Y.-Q.; Gao, B.; Li, N.

doi:10.1107/S1600536803020294

Buy article online - an online subscription or single-article purchase is required to access this article.

4′-(4-Chlorophenyl)-1′-methyl-4′′,5′′,6′′,7′′-tetrahydro-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2′′-(thiazolo[3,2-a]pyrimidine)-2(3H),3′′(2′′H)-dione

X.-F. Li, Y.-Q. Feng, B. Gao and N. Li

The title compound, C₂₃H₂₁ClN₄O₂S, was synthesized by the intermolecular [3 + 2]-cycloaddition of azomethine ylide, derived from isatin and sarcosine by a decarboxylative route, and 2-(4-chlorobenzylidene)-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidin-3-one. In the molecule, the two spiro junctions link a planar 2-oxindole ring, a pyrrolidine ring in an envelope conformation and a 6,7-dihydro-5H-thiazolo[3,2-a]pyrimidin-3-one ring. Two molecules are connected into a dimer by two N—H

N hydrogen bonds

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020294/cv6235sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020294/cv6235Isup2.hkl Contains datablock I

CCDC reference: 226943

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.061
wR factor = 0.170
Data-to-parameter ratio = 16.2

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:      0.769     0.942
            Tmin' and Tmax expected:      0.885     0.942
            RR' =      0.869
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87
PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms .....          2
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.64 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C20
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT751_ALERT_4_C Bond    Calc     1.51563, Rep    1.515(4) ......  Senseless su
              C7   -C17     1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     1.37079, Rep    1.371(4) ......  Senseless su
              C17  -C22     1.555   1.555
PLAT751_ALERT_4_C Bond    Calc     1.38750, Rep    1.387(5) ......  Senseless su
              C18  -C19     1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      117.94, Rep    117.9(2) ......  Senseless su
              C17  -C7   -C8      1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      115.66, Rep    115.7(2) ......  Senseless su
              C17  -C7   -C1      1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      118.56, Rep    118.6(2) ......  Senseless su
              C22  -C17  -C18     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      119.21, Rep    119.2(3) ......  Senseless su
              C22  -C17  -C7      1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      122.06, Rep  122.09(14) ......  Senseless su
              C18  -C17  -C7      1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      119.64, Rep    119.6(2) ......  Senseless su
              C19  -C18  -C17     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      120.38, Rep    120.4(5) ......  Senseless su
              C20  -C19  -C18     1.555   1.555   1.555
PLAT752_ALERT_4_C Angle   Calc      120.87, Rep    120.9(4) ......  Senseless su
              C17  -C22  -C21     1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc     -119.28, Rep   -119.3(3) ......  Senseless su
              C2  -C1  -C7  -C17    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      124.39, Rep    124.3(2) ......  Senseless su
              C9  -C1  -C7  -C17    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       -0.74, Rep     -0.8(3) ......  Senseless su
              S1  -C1  -C7  -C17    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc     -149.01, Rep   -149.0(2) ......  Senseless su
              C17 -C7  -C8  -N4     1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc     -137.49, Rep   -137.5(3) ......  Senseless su
              C8  -C7  -C17 -C22    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       99.52, Rep     99.5(3) ......  Senseless su
              C1  -C7  -C17 -C22    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       47.23, Rep     47.2(3) ......  Senseless su
              C8  -C7  -C17 -C18    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      -75.77, Rep    -75.7(2) ......  Senseless su
              C1  -C7  -C17 -C18    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc        0.21, Rep      0.2(3) ......  Senseless su
              C22 -C17 -C18 -C19    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc      175.53, Rep    175.5(3) ......  Senseless su
              C7  -C17 -C18 -C19    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc       -1.34, Rep     -1.3(5) ......  Senseless su
              C17 -C18 -C19 -C20    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc        2.28, Rep      2.2(7) ......  Senseless su
              C18 -C19 -C20 -C21    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc     -175.69, Rep   -175.7(3) ......  Senseless su
              C18 -C19 -C20 -CL1    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc     -175.45, Rep   -175.5(3) ......  Senseless su
              C7  -C17 -C22 -C21    1.555   1.555   1.555   1.555
PLAT753_ALERT_4_C Torsion Calc        0.91, Rep      0.9(6) ......  Senseless su
              C20 -C21 -C22 -C17    1.555   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  32 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
  26 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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.

4'-(4-Chlorophenyl)-1'-methyl-4'',5'',6'',7''-tetrahydro- 1H-indole-3-spiro-2'-pyrrolidine-3'-spiro-2''-(thiazolo[3,2-a]pyrimidine)- 2(3H),3''(2''H)-dione top

Crystal data top

C₂₃H₂₁ClN₄O₂S	F(000) = 1888
M_r = 452.95	D_x = 1.386 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1009 reflections
a = 22.308 (8) Å	θ = 3.0–26.2°
b = 13.224 (5) Å	µ = 0.30 mm⁻¹
c = 15.054 (6) Å	T = 293 K
β = 102.250 (8)°	Block, colorless
V = 4340 (3) Å³	0.40 × 0.22 × 0.20 mm
Z = 8

Data collection top

Bruker CCD area-detector diffractometer	4454 independent reflections
Radiation source: fine-focus sealed tube	2952 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
φ and ω scans	θ_max = 26.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −27→27
T_min = 0.769, T_max = 0.942	k = −15→16
17147 measured reflections	l = −18→18

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.061	w = 1/[σ²(F_o²) + (0.084P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.170	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.57 e Å⁻³
4454 reflections	Δρ_min = −0.57 e Å⁻³
275 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.92436 (3)	1.00085 (6)	0.11501 (5)	0.0414 (2)
N1	0.86884 (10)	0.86053 (19)	0.00837 (15)	0.0354 (6)
N2	0.97669 (11)	0.8677 (2)	0.02480 (16)	0.0402 (6)
N3	0.91916 (12)	0.8833 (2)	0.32828 (17)	0.0448 (6)
H3	0.9485	0.8876	0.3755	0.054*
N4	0.77441 (11)	0.9509 (2)	0.20924 (17)	0.0449 (7)
O1	0.76825 (9)	0.8898 (2)	0.00441 (15)	0.0530 (6)
O2	0.89043 (12)	1.04861 (18)	0.31823 (15)	0.0572 (6)
C1	0.84450 (12)	0.9771 (2)	0.11740 (18)	0.0364 (7)
C2	0.82171 (13)	0.9059 (2)	0.03716 (19)	0.0375 (7)
C3	0.92688 (12)	0.8976 (2)	0.04217 (18)	0.0330 (6)
C4	0.97239 (16)	0.7853 (3)	−0.0417 (2)	0.0524 (9)
H4A	1.0098	0.7457	−0.0280	0.063*
H4B	0.9688	0.8139	−0.1019	0.063*
C5	0.91828 (17)	0.7165 (3)	−0.0418 (2)	0.0550 (9)
H5A	0.9153	0.6673	−0.0903	0.066*
H5B	0.9247	0.6801	0.0154	0.066*
C6	0.85940 (15)	0.7752 (2)	−0.0547 (2)	0.0436 (8)
H6A	0.8478	0.7994	−0.1168	0.052*
H6B	0.8268	0.7322	−0.0428	0.052*
C9	0.83694 (13)	0.9223 (2)	0.20719 (19)	0.0374 (7)
C10	0.88566 (14)	0.9621 (3)	0.2909 (2)	0.0397 (7)
C11	0.90123 (14)	0.7934 (2)	0.2821 (2)	0.0408 (7)
C12	0.92650 (16)	0.6996 (3)	0.3000 (2)	0.0547 (9)
H12	0.9605	0.6894	0.3468	0.066*
C13	0.89966 (19)	0.6205 (3)	0.2460 (3)	0.0610 (10)
H13	0.9164	0.5560	0.2559	0.073*
C14	0.84856 (18)	0.6351 (3)	0.1778 (2)	0.0570 (9)
H14	0.8309	0.5805	0.1429	0.068*
C15	0.82349 (15)	0.7300 (3)	0.1610 (2)	0.0459 (8)
H15	0.7886	0.7395	0.1154	0.055*
C16	0.85038 (13)	0.8109 (2)	0.21217 (19)	0.0381 (7)
Cl1	0.93615 (9)	1.45584 (10)	0.06370 (14)	0.1360 (8)
C7	0.80147 (14)	1.0720 (3)	0.1092 (2)	0.0457 (8)
H7A	0.7705	1.0634	0.0528	0.055*
C8	0.76794 (10)	1.05771 (16)	0.18746 (14)	0.0517 (9)
H8A	0.7866	1.0986	0.2395	0.062*
H8B	0.7250	1.0761	0.1686	0.062*
C17	0.83205 (10)	1.17300 (16)	0.10139 (14)	0.0492 (8)
C18	0.86922 (10)	1.21977 (16)	0.17585 (14)	0.0672 (11)
H18A	0.8738	1.1916	0.2335	0.081*
C19	0.8995 (2)	1.3087 (3)	0.1637 (3)	0.0827 (14)
H19A	0.9237	1.3408	0.2136	0.099*
C20	0.8940 (3)	1.3489 (3)	0.0796 (4)	0.0810 (15)
C21	0.8574 (2)	1.3052 (4)	0.0067 (4)	0.0864 (16)
H21A	0.8529	1.3345	−0.0505	0.104*
C22	0.82659 (19)	1.2165 (4)	0.0174 (3)	0.0722 (12)
H22A	0.8019	1.1860	−0.0331	0.087*
C23	0.75339 (19)	0.9209 (3)	0.2909 (3)	0.0687 (11)
H23A	0.7617	0.8503	0.3025	0.103*
H23B	0.7101	0.9327	0.2821	0.103*
H23C	0.7746	0.9599	0.3417	0.103*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0349 (4)	0.0502 (5)	0.0403 (4)	−0.0035 (3)	0.0112 (3)	−0.0127 (4)
N1	0.0360 (12)	0.0459 (15)	0.0249 (12)	−0.0034 (11)	0.0078 (10)	−0.0048 (10)
N2	0.0369 (13)	0.0506 (16)	0.0330 (13)	0.0063 (12)	0.0074 (10)	−0.0012 (12)
N3	0.0423 (14)	0.0539 (17)	0.0331 (14)	0.0022 (13)	−0.0036 (11)	−0.0059 (13)
N4	0.0382 (13)	0.0630 (18)	0.0380 (14)	0.0065 (13)	0.0179 (11)	0.0028 (13)
O1	0.0342 (12)	0.0855 (18)	0.0369 (12)	−0.0029 (11)	0.0025 (9)	−0.0111 (12)
O2	0.0771 (17)	0.0472 (15)	0.0432 (13)	0.0027 (12)	0.0032 (12)	−0.0115 (12)
C1	0.0301 (14)	0.0528 (19)	0.0267 (14)	0.0016 (12)	0.0067 (11)	−0.0019 (13)
C2	0.0342 (15)	0.054 (2)	0.0244 (14)	0.0003 (13)	0.0074 (12)	−0.0001 (13)
C3	0.0342 (14)	0.0420 (17)	0.0228 (14)	0.0030 (12)	0.0059 (11)	0.0016 (12)
C4	0.0527 (19)	0.060 (2)	0.0448 (19)	0.0163 (17)	0.0116 (15)	−0.0104 (17)
C5	0.074 (2)	0.043 (2)	0.048 (2)	0.0038 (18)	0.0117 (17)	−0.0095 (16)
C6	0.0533 (19)	0.050 (2)	0.0282 (16)	−0.0083 (15)	0.0094 (13)	−0.0080 (14)
C9	0.0339 (15)	0.0511 (19)	0.0284 (15)	0.0017 (13)	0.0090 (11)	−0.0059 (13)
C10	0.0425 (16)	0.0478 (19)	0.0306 (15)	0.0003 (14)	0.0114 (12)	−0.0053 (14)
C11	0.0390 (16)	0.0490 (19)	0.0345 (16)	−0.0015 (14)	0.0083 (12)	−0.0055 (14)
C12	0.054 (2)	0.059 (2)	0.049 (2)	0.0090 (17)	0.0068 (16)	−0.0003 (18)
C13	0.080 (3)	0.047 (2)	0.059 (2)	0.0043 (19)	0.022 (2)	−0.0007 (18)
C14	0.074 (2)	0.051 (2)	0.050 (2)	−0.0181 (19)	0.0240 (19)	−0.0112 (17)
C15	0.0449 (17)	0.061 (2)	0.0331 (17)	−0.0154 (16)	0.0111 (13)	−0.0058 (15)
C16	0.0370 (15)	0.0499 (19)	0.0294 (15)	−0.0048 (13)	0.0119 (12)	−0.0019 (13)
Cl1	0.2024 (18)	0.0528 (7)	0.1972 (18)	0.0060 (9)	0.1421 (15)	0.0108 (9)
C7	0.0415 (17)	0.064 (2)	0.0315 (16)	0.0133 (15)	0.0075 (13)	−0.0003 (15)
C8	0.0455 (18)	0.067 (2)	0.0467 (19)	0.0159 (17)	0.0198 (15)	−0.0007 (17)
C17	0.0558 (19)	0.055 (2)	0.0427 (19)	0.0208 (17)	0.0240 (15)	0.0044 (16)
C18	0.106 (3)	0.053 (2)	0.051 (2)	0.002 (2)	0.035 (2)	−0.0022 (18)
C19	0.126 (4)	0.055 (3)	0.083 (3)	−0.003 (3)	0.056 (3)	−0.011 (2)
C20	0.109 (4)	0.046 (2)	0.109 (4)	0.025 (2)	0.071 (3)	0.011 (3)
C21	0.093 (3)	0.091 (4)	0.089 (4)	0.036 (3)	0.050 (3)	0.049 (3)
C22	0.069 (3)	0.096 (3)	0.055 (2)	0.026 (2)	0.021 (2)	0.022 (2)
C23	0.071 (2)	0.086 (3)	0.061 (2)	0.010 (2)	0.041 (2)	0.007 (2)

Geometric parameters (Å, º) top

S1—C3	1.760 (3)	C11—C16	1.393 (4)
S1—C1	1.817 (3)	C12—C13	1.381 (5)
N1—C2	1.359 (4)	C12—H12	0.9300
N1—C3	1.377 (4)	C13—C14	1.376 (5)
N1—C6	1.461 (4)	C13—H13	0.9300
N2—C3	1.258 (4)	C14—C15	1.375 (5)
N2—C4	1.470 (4)	C14—H14	0.9300
N3—C10	1.334 (4)	C15—C16	1.379 (4)
N3—C11	1.392 (4)	C15—H15	0.9300
N3—H3	0.8600	Cl1—C20	1.743 (5)
N4—C8	1.450 (4)	C7—C17	1.515 (4)
N4—C9	1.452 (4)	C7—C8	1.536 (4)
N4—C23	1.460 (4)	C7—H7A	0.9800
O1—C2	1.209 (3)	C8—H8A	0.9700
O2—C10	1.213 (4)	C8—H8B	0.9700
C1—C2	1.531 (4)	C17—C22	1.371 (4)
C1—C7	1.569 (4)	C17—C18	1.3900
C1—C9	1.574 (4)	C18—C19	1.387 (5)
C4—C5	1.511 (5)	C18—H18A	0.9300
C4—H4A	0.9700	C19—C20	1.355 (7)
C4—H4B	0.9700	C19—H19A	0.9300
C5—C6	1.502 (5)	C20—C21	1.351 (7)
C5—H5A	0.9700	C21—C22	1.386 (7)
C5—H5B	0.9700	C21—H21A	0.9300
C6—H6A	0.9700	C22—H22A	0.9300
C6—H6B	0.9700	C23—H23A	0.9600
C9—C16	1.503 (4)	C23—H23B	0.9600
C9—C10	1.570 (4)	C23—H23C	0.9600
C11—C12	1.365 (5)

C3—S1—C1	92.26 (13)	N3—C11—C16	109.7 (3)
C2—N1—C3	117.1 (2)	C11—C12—C13	117.6 (3)
C2—N1—C6	122.3 (2)	C11—C12—H12	121.2
C3—N1—C6	120.6 (2)	C13—C12—H12	121.2
C3—N2—C4	116.2 (3)	C14—C13—C12	121.3 (4)
C10—N3—C11	112.3 (2)	C14—C13—H13	119.4
C10—N3—H3	123.8	C12—C13—H13	119.4
C11—N3—H3	123.8	C15—C14—C13	120.4 (3)
C8—N4—C9	107.4 (2)	C15—C14—H14	119.8
C8—N4—C23	114.9 (3)	C13—C14—H14	119.8
C9—N4—C23	115.4 (3)	C14—C15—C16	119.5 (3)
C2—C1—C7	109.5 (2)	C14—C15—H15	120.2
C2—C1—C9	108.5 (2)	C16—C15—H15	120.2
C7—C1—C9	105.1 (2)	C15—C16—C11	118.8 (3)
C2—C1—S1	104.69 (18)	C15—C16—C9	132.4 (3)
C7—C1—S1	116.5 (2)	C11—C16—C9	108.8 (3)
C9—C1—S1	112.38 (19)	C17—C7—C8	117.9 (2)
O1—C2—N1	123.7 (3)	C17—C7—C1	115.7 (2)
O1—C2—C1	124.3 (3)	C8—C7—C1	103.3 (2)
N1—C2—C1	111.9 (2)	C17—C7—H7A	106.4
N2—C3—N1	127.9 (3)	C8—C7—H7A	106.4
N2—C3—S1	121.3 (2)	C1—C7—H7A	106.4
N1—C3—S1	110.8 (2)	N4—C8—C7	104.6 (2)
N2—C4—C5	112.6 (3)	N4—C8—H8A	110.8
N2—C4—H4A	109.1	C7—C8—H8A	110.8
C5—C4—H4A	109.1	N4—C8—H8B	110.8
N2—C4—H4B	109.1	C7—C8—H8B	110.8
C5—C4—H4B	109.1	H8A—C8—H8B	108.9
H4A—C4—H4B	107.8	C22—C17—C18	118.6 (2)
C6—C5—C4	111.5 (3)	C22—C17—C7	119.2 (3)
C6—C5—H5A	109.3	C18—C17—C7	122.09 (14)
C4—C5—H5A	109.3	C19—C18—C17	119.6 (2)
C6—C5—H5B	109.3	C19—C18—H18A	120.2
C4—C5—H5B	109.3	C17—C18—H18A	120.2
H5A—C5—H5B	108.0	C20—C19—C18	120.4 (5)
N1—C6—C5	108.3 (2)	C20—C19—H19A	119.8
N1—C6—H6A	110.0	C18—C19—H19A	119.8
C5—C6—H6A	110.0	C21—C20—C19	120.7 (5)
N1—C6—H6B	110.0	C21—C20—Cl1	119.1 (4)
C5—C6—H6B	110.0	C19—C20—Cl1	120.1 (5)
H6A—C6—H6B	108.4	C20—C21—C22	119.8 (4)
N4—C9—C16	115.9 (3)	C20—C21—H21A	120.1
N4—C9—C10	113.6 (2)	C22—C21—H21A	120.1
C16—C9—C10	101.0 (2)	C17—C22—C21	120.9 (4)
N4—C9—C1	100.2 (2)	C17—C22—H22A	119.6
C16—C9—C1	115.9 (2)	C21—C22—H22A	119.6
C10—C9—C1	110.7 (2)	N4—C23—H23A	109.5
O2—C10—N3	126.3 (3)	N4—C23—H23B	109.5
O2—C10—C9	125.7 (3)	H23A—C23—H23B	109.5
N3—C10—C9	107.9 (3)	N4—C23—H23C	109.5
C12—C11—N3	127.9 (3)	H23A—C23—H23C	109.5
C12—C11—C16	122.4 (3)	H23B—C23—H23C	109.5

C3—S1—C1—C2	−15.9 (2)	N4—C9—C10—N3	127.1 (3)
C3—S1—C1—C7	−137.0 (2)	C16—C9—C10—N3	2.3 (3)
C3—S1—C1—C9	101.6 (2)	C1—C9—C10—N3	−121.1 (3)
C3—N1—C2—O1	170.1 (3)	C10—N3—C11—C12	178.0 (3)
C6—N1—C2—O1	−10.6 (5)	C10—N3—C11—C16	−3.5 (4)
C3—N1—C2—C1	−11.5 (4)	N3—C11—C12—C13	178.2 (3)
C6—N1—C2—C1	167.7 (3)	C16—C11—C12—C13	−0.2 (5)
C7—C1—C2—O1	−37.9 (4)	C11—C12—C13—C14	−1.3 (5)
C9—C1—C2—O1	76.3 (4)	C12—C13—C14—C15	1.0 (6)
S1—C1—C2—O1	−163.5 (3)	C13—C14—C15—C16	0.9 (5)
C7—C1—C2—N1	143.7 (3)	C14—C15—C16—C11	−2.3 (4)
C9—C1—C2—N1	−102.0 (3)	C14—C15—C16—C9	175.7 (3)
S1—C1—C2—N1	18.1 (3)	C12—C11—C16—C15	2.0 (5)
C4—N2—C3—N1	2.0 (5)	N3—C11—C16—C15	−176.7 (3)
C4—N2—C3—S1	−176.0 (2)	C12—C11—C16—C9	−176.4 (3)
C2—N1—C3—N2	−179.7 (3)	N3—C11—C16—C9	4.9 (3)
C6—N1—C3—N2	1.1 (5)	N4—C9—C16—C15	54.4 (4)
C2—N1—C3—S1	−1.5 (3)	C10—C9—C16—C15	177.6 (3)
C6—N1—C3—S1	179.3 (2)	C1—C9—C16—C15	−62.7 (4)
C1—S1—C3—N2	−170.7 (3)	N4—C9—C16—C11	−127.5 (3)
C1—S1—C3—N1	10.9 (2)	C10—C9—C16—C11	−4.3 (3)
C3—N2—C4—C5	−29.5 (4)	C1—C9—C16—C11	115.4 (3)
N2—C4—C5—C6	53.9 (4)	C2—C1—C7—C17	−119.3 (3)
C2—N1—C6—C5	−156.1 (3)	C9—C1—C7—C17	124.3 (2)
C3—N1—C6—C5	23.1 (4)	S1—C1—C7—C17	−0.8 (3)
C4—C5—C6—N1	−48.6 (4)	C2—C1—C7—C8	110.3 (2)
C8—N4—C9—C16	−169.9 (2)	C9—C1—C7—C8	−6.0 (3)
C23—N4—C9—C16	60.6 (4)	S1—C1—C7—C8	−131.2 (2)
C8—N4—C9—C10	73.7 (3)	C9—N4—C8—C7	42.0 (3)
C23—N4—C9—C10	−55.8 (4)	C23—N4—C8—C7	171.8 (3)
C8—N4—C9—C1	−44.4 (3)	C17—C7—C8—N4	−149.0 (2)
C23—N4—C9—C1	−173.9 (3)	C1—C7—C8—N4	−20.0 (3)
C2—C1—C9—N4	−87.6 (3)	C8—C7—C17—C22	−137.5 (3)
C7—C1—C9—N4	29.5 (3)	C1—C7—C17—C22	99.5 (3)
S1—C1—C9—N4	157.2 (2)	C8—C7—C17—C18	47.2 (3)
C2—C1—C9—C16	37.9 (3)	C1—C7—C17—C18	−75.7 (2)
C7—C1—C9—C16	155.0 (2)	C22—C17—C18—C19	0.2 (3)
S1—C1—C9—C16	−77.3 (3)	C7—C17—C18—C19	175.5 (3)
C2—C1—C9—C10	152.2 (2)	C17—C18—C19—C20	−1.3 (5)
C7—C1—C9—C10	−90.7 (3)	C18—C19—C20—C21	2.2 (7)
S1—C1—C9—C10	37.0 (3)	C18—C19—C20—Cl1	−175.7 (3)
C11—N3—C10—O2	178.3 (3)	C19—C20—C21—C22	−2.0 (7)
C11—N3—C10—C9	0.5 (3)	Cl1—C20—C21—C22	175.9 (3)
N4—C9—C10—O2	−50.7 (4)	C18—C17—C22—C21	0.0 (4)
C16—C9—C10—O2	−175.5 (3)	C7—C17—C22—C21	−175.5 (3)
C1—C9—C10—O2	61.1 (4)	C20—C21—C22—C17	0.9 (6)

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page