10′′-(4-Methoxy­benzyl­idene)-5′′,4′-bis(4-methoxy­phen­yl)-1′-meth­yl-2,3,2′′,3′′,7′′,8′′,9′′,10′′-octa­hydro-1H,5′′H,6′′H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2′′-cyclo­hepteno[1,2-d]thia­zolo[3,2-a]pyrimidine-2,3′′-dione

The title compound, C₄₄H₄₂N₄O₅S, was synthesized by the inter­molecular [3+2] cyclo­addition of an azomethine ylide, derived from isatin and sarcosine by a deca­rboxylative route, and 5-(4-methoxyphen­yl-10-(4-methoxy)benzyl­idene-2-(4-methoxy)benzyl­idene-2,3,6,7,8,9-hexa­hydro-5H,10H-cyclohepta­[1,2-d]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 10-(aryl­methyl­ene)hexa­hydro­cyclo­hepta­[1,2-d]thia­zolo[3,2-a]pyrimidin-3-one ring. The packing of the mol­ecules in the crystal structure is mainly governed by N—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.055
• wR factor = 0.140
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A
PLAT770_ALERT_2_A Suspect C-H Bond in CIF:      C20    -H19D    ..       1.41 Ang.

Author Response: The cycloheptene ring was disorder and the ADDSYM result is an artefact of this disorder. ADDSYM reaches its conclusion having excluded all the atoms of the disordered cycloheptene ring. See Comment text.

PLAT770_ALERT_2_A Suspect C-H Bond in CIF:      C20'   -H19A    ..       1.45 Ang.

Author Response: The cycloheptene ring was disorder and the ADDSYM result is an artefact of this disorder. ADDSYM reaches its conclusion having excluded all the atoms of the disordered cycloheptene ring. See Comment text.

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.80 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.17 Ratio

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C21
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C41
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C20'
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT411_ALERT_2_C Short Inter H...H Contact  H7     ..  H7      ..       2.13 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.87(3), Rep   0.863(10) ......       3.00 su-Rat
              N4   -H4      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.87(3), Rep   0.863(10) ......       3.00 su-Rat
              N4   -H4      1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      37.50 Deg.
              C19  -C20  -H19D    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.80 Deg.
              C21  -C20  -H21C    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      37.00 Deg.
              C19  -C20' -H19A    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      41.30 Deg.
              C21  -C20' -H21B    1.555   1.555   1.555

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

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

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.

10''-(4-Methoxybenzylidene)-5''-(4-methoxyphenyl)-4'-(4-methoxyphenyl)-1'- methyl-2,3,2'',3'',7'',8'',9'',10''-octahydro-1H,5''H,6''H-indole-3-spiro-2'- pyrrolidine-3'-spiro-2''-cyclohepteno[1,2-d]thiazolo[3,2-a]pyrimidine-2,3''- dione

Crystal data

C44H42N4O5S	Z = 2
Mr = 738.88	F(000) = 780
Triclinic, P1	Dx = 1.320 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6294 (19) Å	Cell parameters from 2110 reflections
b = 13.299 (2) Å	θ = 2.3–23.1°
c = 13.702 (2) Å	µ = 0.14 mm^−1
α = 104.778 (3)°	T = 294 K
β = 95.840 (3)°	Block, colourless
γ = 91.828 (3)°	0.28 × 0.24 × 0.20 mm
V = 1859.8 (5) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	7546 independent reflections
Radiation source: fine-focus sealed tube	4011 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 26.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→11
Tmin = 0.958, Tmax = 0.972	k = −16→15
10666 measured reflections	l = −17→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.055	w = 1/[σ^2(Fo^2) + (0.0505P)^2 + 0.3384P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.140	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.29 e Å^−3
7546 reflections	Δρmin = −0.21 e Å^−3
505 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	0.50880 (7)	0.13525 (6)	0.21676 (6)	0.0377 (2)
N1	0.2737 (2)	0.08272 (17)	0.22611 (15)	0.0317 (5)
N2	0.3072 (2)	0.19743 (17)	0.12355 (16)	0.0334 (6)
N3	0.6341 (2)	−0.07797 (18)	0.33177 (17)	0.0398 (6)
N4	0.5676 (3)	−0.1296 (2)	0.0685 (2)	0.0526 (7)
H4	0.610 (3)	−0.146 (2)	0.0165 (16)	0.064 (11)*
O1	0.28269 (17)	−0.03197 (15)	0.32455 (14)	0.0408 (5)
O2	0.7154 (2)	−0.00034 (18)	0.15861 (18)	0.0617 (7)
O3	−0.0288 (2)	0.3004 (2)	0.59683 (18)	0.0799 (8)
O4	0.5063 (3)	0.48626 (19)	0.63707 (19)	0.0783 (8)
O5	0.1221 (3)	0.5675 (2)	−0.2782 (2)	0.0888 (9)
C1	0.4815 (2)	0.0374 (2)	0.28657 (19)	0.0325 (7)
C2	0.3368 (3)	0.0231 (2)	0.28135 (19)	0.0322 (7)
C3	0.3480 (3)	0.1438 (2)	0.18363 (19)	0.0306 (6)
C4	0.1733 (3)	0.1911 (2)	0.0943 (2)	0.0339 (7)
C5	0.0911 (3)	0.1426 (2)	0.1366 (2)	0.0404 (7)
C6	0.1348 (2)	0.0910 (2)	0.2200 (2)	0.0357 (7)
H6	0.0956	0.0200	0.2007	0.043*
C7	0.5394 (3)	0.0719 (2)	0.40060 (19)	0.0352 (7)
H7	0.4898	0.0323	0.4363	0.042*
C8	0.6669 (3)	0.0261 (2)	0.3971 (2)	0.0425 (8)
H8A	0.7249	0.0648	0.3677	0.051*
H8B	0.7040	0.0240	0.4641	0.051*
C9	0.5494 (3)	−0.0685 (2)	0.2431 (2)	0.0343 (7)
C10	0.6233 (3)	−0.0580 (3)	0.1527 (2)	0.0456 (8)
C11	0.4814 (3)	−0.1988 (2)	0.0927 (2)	0.0419 (7)
C12	0.4684 (3)	−0.1674 (2)	0.1958 (2)	0.0334 (7)
C13	0.4013 (3)	−0.2311 (2)	0.2391 (2)	0.0436 (8)
H13	0.3943	−0.2123	0.3085	0.052*
C14	0.3442 (3)	−0.3240 (3)	0.1776 (3)	0.0568 (9)
H14	0.2984	−0.3678	0.2061	0.068*
C15	0.3541 (3)	−0.3523 (3)	0.0753 (3)	0.0632 (10)
H15	0.3133	−0.4142	0.0353	0.076*
C16	0.4238 (3)	−0.2905 (3)	0.0308 (2)	0.0591 (10)
H16	0.4315	−0.3099	−0.0384	0.071*
C17	0.1394 (3)	0.2413 (2)	0.0101 (2)	0.0382 (7)
C18	0.0334 (3)	0.1876 (3)	−0.0688 (2)	0.0517 (9)
H18A	0.0388	0.2133	−0.1286	0.062*
H18B	0.0478	0.1139	−0.0880	0.062*
C19	−0.0993 (3)	0.1990 (3)	−0.0411 (3)	0.0712 (11)
H19A	−0.1509	0.1382	−0.0789	0.085*	0.526 (8)
H19B	−0.1326	0.2580	−0.0609	0.085*	0.526 (8)
H19C	−0.1580	0.1861	−0.1017	0.085*	0.474 (8)
H19D	−0.1084	0.2683	−0.0007	0.085*	0.474 (8)
C20	−0.1103 (6)	0.2123 (6)	0.0735 (5)	0.060 (3)	0.526 (8)
H20A	−0.0746	0.2811	0.1105	0.072*	0.526 (8)
H20B	−0.1995	0.2096	0.0827	0.072*	0.526 (8)
C20'	−0.1269 (6)	0.1190 (7)	0.0208 (5)	0.055 (3)	0.474 (8)
H20C	−0.2155	0.1201	0.0320	0.067*	0.474 (8)
H20D	−0.1128	0.0498	−0.0195	0.067*	0.474 (8)
C21	−0.0505 (3)	0.1380 (3)	0.1179 (3)	0.0755 (12)
H21A	−0.0823	0.1437	0.1821	0.091*	0.526 (8)
H21B	−0.0782	0.0702	0.0752	0.091*	0.526 (8)
H21C	−0.0760	0.2028	0.1580	0.091*	0.474 (8)
H21D	−0.0789	0.0850	0.1482	0.091*	0.474 (8)
C22	0.0939 (3)	0.1461 (2)	0.3227 (2)	0.0363 (7)
C23	0.1066 (3)	0.2535 (3)	0.3588 (3)	0.0537 (9)
H23	0.1430	0.2932	0.3210	0.064*
C24	0.0655 (3)	0.3022 (3)	0.4509 (3)	0.0634 (10)
H24	0.0752	0.3743	0.4748	0.076*
C25	0.0102 (3)	0.2444 (3)	0.5073 (2)	0.0537 (9)
C26	−0.0038 (3)	0.1383 (3)	0.4723 (2)	0.0506 (9)
H26	−0.0410	0.0986	0.5098	0.061*
C27	0.0383 (3)	0.0908 (3)	0.3799 (2)	0.0452 (8)
H27	0.0284	0.0186	0.3561	0.054*
C28	−0.0814 (4)	0.2430 (4)	0.6594 (3)	0.0872 (14)
H28A	−0.1557	0.2023	0.6229	0.131*
H28B	−0.1038	0.2904	0.7198	0.131*
H28C	−0.0202	0.1976	0.6778	0.131*
C29	0.5342 (3)	0.1858 (2)	0.4566 (2)	0.0377 (7)
C30	0.6377 (3)	0.2543 (2)	0.4795 (2)	0.0484 (8)
H30	0.7133	0.2328	0.4548	0.058*
C31	0.6330 (3)	0.3568 (3)	0.5397 (2)	0.0528 (9)
H31	0.7047	0.4023	0.5544	0.063*
C32	0.5218 (3)	0.3889 (2)	0.5762 (2)	0.0501 (8)
C33	0.4161 (3)	0.3213 (3)	0.5525 (2)	0.0556 (9)
H33	0.3400	0.3436	0.5760	0.067*
C34	0.4219 (3)	0.2215 (3)	0.4946 (2)	0.0497 (8)
H34	0.3497	0.1765	0.4803	0.060*
C35	0.6123 (4)	0.5585 (3)	0.6673 (3)	0.0910 (14)
H35A	0.6765	0.5314	0.7063	0.136*
H35B	0.5871	0.6232	0.7079	0.136*
H35C	0.6453	0.5701	0.6081	0.136*
C36	0.2102 (3)	0.3231 (2)	0.0020 (2)	0.0447 (8)
H36	0.2809	0.3444	0.0497	0.054*
C37	0.1887 (3)	0.3837 (2)	−0.0746 (2)	0.0429 (8)
C38	0.2867 (3)	0.4109 (2)	−0.1239 (2)	0.0483 (8)
H38	0.3670	0.3883	−0.1103	0.058*
C39	0.2688 (3)	0.4707 (2)	−0.1931 (2)	0.0515 (9)
H39	0.3357	0.4862	−0.2267	0.062*
C40	0.1516 (4)	0.5068 (3)	−0.2116 (3)	0.0592 (10)
C41	0.0529 (4)	0.4827 (3)	−0.1632 (3)	0.0778 (12)
H41	−0.0263	0.5077	−0.1752	0.093*
C42	0.0719 (3)	0.4209 (3)	−0.0962 (3)	0.0641 (10)
H42	0.0038	0.4038	−0.0647	0.077*
C43	0.2215 (5)	0.6079 (4)	−0.3182 (4)	0.1166 (19)
H43A	0.2803	0.6490	−0.2637	0.175*
H43B	0.1888	0.6508	−0.3604	0.175*
H43C	0.2639	0.5517	−0.3579	0.175*
C44	0.7399 (3)	−0.1444 (3)	0.3092 (3)	0.0591 (10)
H44A	0.7084	−0.2115	0.2669	0.089*
H44B	0.7833	−0.1525	0.3715	0.089*
H44C	0.7975	−0.1129	0.2745	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0319 (4)	0.0480 (5)	0.0391 (4)	−0.0023 (3)	0.0053 (3)	0.0221 (4)
N1	0.0307 (13)	0.0397 (14)	0.0281 (12)	−0.0001 (11)	0.0044 (10)	0.0150 (11)
N2	0.0351 (14)	0.0394 (14)	0.0286 (12)	−0.0003 (11)	0.0045 (11)	0.0142 (11)
N3	0.0393 (14)	0.0412 (15)	0.0355 (14)	0.0078 (12)	−0.0034 (11)	0.0061 (12)
N4	0.0572 (18)	0.069 (2)	0.0337 (16)	0.0104 (15)	0.0222 (14)	0.0107 (15)
O1	0.0397 (12)	0.0464 (13)	0.0454 (12)	0.0013 (9)	0.0127 (10)	0.0255 (10)
O2	0.0484 (14)	0.0693 (16)	0.0762 (16)	−0.0011 (12)	0.0310 (13)	0.0260 (13)
O3	0.0822 (19)	0.094 (2)	0.0563 (16)	0.0121 (15)	0.0264 (15)	−0.0023 (15)
O4	0.099 (2)	0.0437 (16)	0.0835 (19)	0.0048 (14)	0.0213 (16)	−0.0032 (14)
O5	0.097 (2)	0.095 (2)	0.102 (2)	0.0202 (17)	0.0217 (17)	0.0721 (18)
C1	0.0342 (16)	0.0390 (17)	0.0275 (15)	0.0002 (13)	0.0051 (12)	0.0138 (13)
C2	0.0370 (16)	0.0349 (17)	0.0243 (15)	0.0000 (13)	0.0050 (13)	0.0064 (13)
C3	0.0356 (16)	0.0352 (17)	0.0210 (14)	−0.0025 (13)	0.0073 (12)	0.0066 (13)
C4	0.0374 (17)	0.0369 (17)	0.0285 (15)	0.0002 (13)	0.0030 (13)	0.0110 (13)
C5	0.0375 (17)	0.054 (2)	0.0339 (16)	−0.0006 (14)	0.0015 (14)	0.0196 (15)
C6	0.0309 (16)	0.0441 (18)	0.0341 (16)	−0.0064 (13)	0.0038 (13)	0.0147 (14)
C7	0.0378 (17)	0.0427 (18)	0.0275 (15)	0.0026 (14)	0.0029 (13)	0.0138 (14)
C8	0.0388 (18)	0.051 (2)	0.0346 (17)	0.0007 (15)	−0.0048 (14)	0.0085 (15)
C9	0.0359 (16)	0.0370 (17)	0.0310 (16)	0.0041 (13)	0.0055 (13)	0.0096 (13)
C10	0.0406 (19)	0.055 (2)	0.048 (2)	0.0130 (17)	0.0172 (16)	0.0193 (18)
C11	0.0426 (18)	0.050 (2)	0.0330 (17)	0.0074 (15)	0.0057 (15)	0.0098 (15)
C12	0.0331 (16)	0.0367 (17)	0.0289 (15)	0.0059 (13)	0.0049 (13)	0.0048 (13)
C13	0.0439 (19)	0.043 (2)	0.0450 (18)	0.0013 (15)	0.0088 (15)	0.0117 (16)
C14	0.053 (2)	0.044 (2)	0.071 (3)	−0.0026 (17)	0.008 (2)	0.0120 (19)
C15	0.053 (2)	0.049 (2)	0.074 (3)	−0.0001 (18)	−0.002 (2)	−0.005 (2)
C16	0.063 (2)	0.063 (2)	0.0375 (19)	0.0111 (19)	−0.0006 (18)	−0.0102 (18)
C17	0.0431 (18)	0.0414 (18)	0.0318 (16)	0.0024 (14)	0.0018 (14)	0.0136 (14)
C18	0.054 (2)	0.059 (2)	0.0441 (19)	0.0033 (17)	−0.0063 (17)	0.0212 (17)
C19	0.054 (2)	0.107 (3)	0.066 (2)	0.005 (2)	−0.0063 (19)	0.051 (2)
C20	0.035 (4)	0.073 (6)	0.083 (6)	0.016 (4)	0.010 (4)	0.038 (5)
C20'	0.045 (4)	0.064 (6)	0.061 (5)	−0.001 (4)	0.004 (4)	0.024 (5)
C21	0.0333 (19)	0.136 (4)	0.073 (3)	−0.009 (2)	−0.0038 (19)	0.062 (3)
C22	0.0283 (15)	0.048 (2)	0.0357 (16)	0.0012 (13)	0.0043 (13)	0.0165 (15)
C23	0.055 (2)	0.052 (2)	0.058 (2)	−0.0041 (17)	0.0182 (18)	0.0178 (18)
C24	0.067 (2)	0.049 (2)	0.069 (3)	0.0024 (18)	0.020 (2)	0.003 (2)
C25	0.045 (2)	0.075 (3)	0.0387 (19)	0.0073 (18)	0.0063 (16)	0.0079 (19)
C26	0.051 (2)	0.067 (3)	0.0407 (19)	0.0037 (18)	0.0128 (16)	0.0237 (18)
C27	0.0444 (19)	0.055 (2)	0.0409 (18)	0.0012 (15)	0.0109 (15)	0.0187 (16)
C28	0.084 (3)	0.140 (4)	0.044 (2)	0.031 (3)	0.033 (2)	0.023 (2)
C29	0.0437 (18)	0.0446 (19)	0.0258 (15)	0.0020 (15)	0.0027 (14)	0.0115 (14)
C30	0.049 (2)	0.049 (2)	0.0469 (19)	0.0004 (16)	0.0119 (16)	0.0104 (17)
C31	0.058 (2)	0.048 (2)	0.050 (2)	−0.0088 (17)	0.0044 (18)	0.0098 (17)
C32	0.068 (2)	0.039 (2)	0.0427 (19)	0.0034 (18)	0.0067 (18)	0.0091 (16)
C33	0.060 (2)	0.049 (2)	0.057 (2)	0.0146 (18)	0.0185 (18)	0.0060 (18)
C34	0.049 (2)	0.051 (2)	0.047 (2)	0.0023 (16)	0.0065 (16)	0.0090 (17)
C35	0.120 (4)	0.046 (2)	0.095 (3)	−0.019 (2)	0.001 (3)	0.004 (2)
C36	0.052 (2)	0.048 (2)	0.0336 (17)	−0.0012 (16)	−0.0038 (15)	0.0139 (15)
C37	0.056 (2)	0.0379 (18)	0.0360 (17)	0.0020 (16)	0.0036 (16)	0.0120 (14)
C38	0.056 (2)	0.0430 (19)	0.0482 (19)	0.0057 (16)	0.0075 (17)	0.0147 (16)
C39	0.069 (2)	0.046 (2)	0.0453 (19)	0.0055 (18)	0.0179 (18)	0.0178 (16)
C40	0.075 (3)	0.057 (2)	0.058 (2)	0.013 (2)	0.010 (2)	0.0354 (19)
C41	0.068 (3)	0.088 (3)	0.103 (3)	0.023 (2)	0.021 (2)	0.064 (3)
C42	0.064 (2)	0.067 (2)	0.079 (3)	0.0117 (19)	0.023 (2)	0.045 (2)
C43	0.122 (4)	0.142 (4)	0.141 (4)	0.048 (3)	0.064 (4)	0.115 (4)
C44	0.052 (2)	0.059 (2)	0.063 (2)	0.0202 (18)	−0.0009 (18)	0.0104 (19)

Geometric parameters (Å, º)

S1—C3	1.739 (3)	C20—C21	1.422 (6)
S1—C1	1.833 (3)	C20—H19D	1.4058
N1—C2	1.374 (3)	C20—H20A	0.9700
N1—C3	1.384 (3)	C20—H20B	0.9700
N1—C6	1.480 (3)	C20—H21C	1.2182
N2—C3	1.273 (3)	C20'—C21	1.446 (6)
N2—C4	1.433 (3)	C20'—H19A	1.4509
N3—C8	1.453 (4)	C20'—H20C	0.9700
N3—C44	1.462 (4)	C20'—H20D	0.9700
N3—C9	1.472 (3)	C20'—H21B	1.1976
N4—C10	1.362 (4)	C21—H21A	0.9599
N4—C11	1.400 (4)	C21—H21B	0.9600
N4—H4	0.863 (10)	C21—H21C	0.9600
O1—C2	1.217 (3)	C21—H21D	0.9600
O2—C10	1.207 (4)	C22—C27	1.366 (4)
O3—C25	1.374 (4)	C22—C23	1.384 (4)
O3—C28	1.427 (4)	C23—C24	1.384 (4)
O4—C32	1.375 (4)	C23—H23	0.9300
O4—C35	1.413 (4)	C24—C25	1.379 (4)
O5—C40	1.385 (4)	C24—H24	0.9300
O5—C43	1.391 (5)	C25—C26	1.367 (5)
C1—C2	1.536 (4)	C26—C27	1.388 (4)
C1—C7	1.566 (4)	C26—H26	0.9300
C1—C9	1.607 (4)	C27—H27	0.9300
C4—C5	1.331 (4)	C28—H28A	0.9600
C4—C17	1.494 (4)	C28—H28B	0.9600
C5—C21	1.497 (4)	C28—H28C	0.9600
C5—C6	1.519 (4)	C29—C30	1.363 (4)
C6—C22	1.526 (4)	C29—C34	1.400 (4)
C6—H6	0.9800	C30—C31	1.406 (4)
C7—C8	1.503 (4)	C30—H30	0.9300
C7—C29	1.519 (4)	C31—C32	1.369 (4)
C7—H7	0.9800	C31—H31	0.9300
C8—H8A	0.9700	C32—C33	1.375 (4)
C8—H8B	0.9700	C33—C34	1.369 (4)
C9—C12	1.507 (4)	C33—H33	0.9300
C9—C10	1.564 (4)	C34—H34	0.9300
C11—C16	1.378 (4)	C35—H35A	0.9600
C11—C12	1.389 (4)	C35—H35B	0.9600
C12—C13	1.373 (4)	C35—H35C	0.9600
C13—C14	1.386 (4)	C36—C37	1.481 (4)
C13—H13	0.9300	C36—H36	0.9300
C14—C15	1.372 (5)	C37—C42	1.383 (4)
C14—H14	0.9300	C37—C38	1.385 (4)
C15—C16	1.380 (5)	C38—C39	1.387 (4)
C15—H15	0.9300	C38—H38	0.9300
C16—H16	0.9300	C39—C40	1.373 (5)
C17—C36	1.338 (4)	C39—H39	0.9300
C17—C18	1.502 (4)	C40—C41	1.367 (5)
C18—C19	1.500 (4)	C41—C42	1.385 (4)
C18—H18A	0.9700	C41—H41	0.9300
C18—H18B	0.9700	C42—H42	0.9300
C19—C20	1.552 (6)	C43—H43A	0.9600
C19—C20'	1.558 (6)	C43—H43B	0.9600
C19—H19A	0.9600	C43—H43C	0.9600
C19—H19B	0.9601	C44—H44A	0.9600
C19—H19C	0.9600	C44—H44B	0.9600
C19—H19D	0.9600	C44—H44C	0.9600
C3—S1—C1	93.26 (12)	H20A—C20—H21C	76.1
C2—N1—C3	116.5 (2)	H20B—C20—H21C	93.7
C2—N1—C6	122.7 (2)	C21—C20'—C19	114.3 (5)
C3—N1—C6	120.5 (2)	C21—C20'—H19A	149.9
C3—N2—C4	117.3 (2)	C19—C20'—H19A	37.0
C8—N3—C44	115.9 (2)	C21—C20'—H20C	108.7
C8—N3—C9	108.0 (2)	C19—C20'—H20C	108.7
C44—N3—C9	115.7 (2)	H19A—C20'—H20C	93.7
C10—N4—C11	111.9 (2)	C21—C20'—H20D	108.7
C10—N4—H4	118 (2)	C19—C20'—H20D	108.7
C11—N4—H4	123 (2)	H19A—C20'—H20D	82.1
C25—O3—C28	117.3 (3)	H20C—C20'—H20D	107.6
C32—O4—C35	118.7 (3)	C21—C20'—H21B	41.3
C40—O5—C43	117.8 (3)	C19—C20'—H21B	143.7
C2—C1—C7	109.1 (2)	H19A—C20'—H21B	150.2
C2—C1—C9	114.1 (2)	H20C—C20'—H21B	105.7
C7—C1—C9	102.9 (2)	H20D—C20'—H21B	70.7
C2—C1—S1	105.04 (17)	C20—C21—C20'	52.3 (4)
C7—C1—S1	113.46 (19)	C20—C21—C5	119.4 (4)
C9—C1—S1	112.51 (17)	C20'—C21—C5	127.0 (4)
O1—C2—N1	122.9 (3)	C20—C21—H21A	107.3
O1—C2—C1	124.0 (2)	C20'—C21—H21A	125.5
N1—C2—C1	113.0 (2)	C5—C21—H21A	107.3
N2—C3—N1	125.6 (2)	C20—C21—H21B	107.3
N2—C3—S1	122.2 (2)	C20'—C21—H21B	55.4
N1—C3—S1	112.09 (19)	C5—C21—H21B	107.8
C5—C4—N2	122.7 (2)	H21A—C21—H21B	107.2
C5—C4—C17	125.1 (3)	C20—C21—H21C	57.7
N2—C4—C17	112.2 (2)	C20'—C21—H21C	105.6
C4—C5—C21	127.3 (3)	C5—C21—H21C	106.0
C4—C5—C6	121.4 (3)	H21A—C21—H21C	57.9
C21—C5—C6	111.2 (2)	H21B—C21—H21C	145.9
N1—C6—C5	109.8 (2)	C20—C21—H21D	135.2
N1—C6—C22	111.4 (2)	C20'—C21—H21D	105.4
C5—C6—C22	112.8 (2)	C5—C21—H21D	105.1
N1—C6—H6	107.5	H21A—C21—H21D	49.5
C5—C6—H6	107.5	H21B—C21—H21D	60.8
C22—C6—H6	107.5	H21C—C21—H21D	106.3
C8—C7—C29	117.9 (2)	C27—C22—C23	118.0 (3)
C8—C7—C1	102.5 (2)	C27—C22—C6	120.6 (3)
C29—C7—C1	117.5 (2)	C23—C22—C6	121.4 (3)
C8—C7—H7	106.0	C24—C23—C22	120.4 (3)
C29—C7—H7	106.0	C24—C23—H23	119.8
C1—C7—H7	106.0	C22—C23—H23	119.8
N3—C8—C7	101.4 (2)	C25—C24—C23	120.4 (3)
N3—C8—H8A	111.5	C25—C24—H24	119.8
C7—C8—H8A	111.5	C23—C24—H24	119.8
N3—C8—H8B	111.5	C26—C25—O3	124.4 (3)
C7—C8—H8B	111.5	C26—C25—C24	119.8 (3)
H8A—C8—H8B	109.3	O3—C25—C24	115.7 (3)
N3—C9—C12	111.4 (2)	C25—C26—C27	119.0 (3)
N3—C9—C10	112.5 (2)	C25—C26—H26	120.5
C12—C9—C10	101.5 (2)	C27—C26—H26	120.5
N3—C9—C1	102.9 (2)	C22—C27—C26	122.4 (3)
C12—C9—C1	118.9 (2)	C22—C27—H27	118.8
C10—C9—C1	109.9 (2)	C26—C27—H27	118.8
O2—C10—N4	127.2 (3)	O3—C28—H28A	109.5
O2—C10—C9	125.9 (3)	O3—C28—H28B	109.5
N4—C10—C9	106.8 (3)	H28A—C28—H28B	109.5
C16—C11—C12	121.9 (3)	O3—C28—H28C	109.5
C16—C11—N4	128.2 (3)	H28A—C28—H28C	109.5
C12—C11—N4	109.6 (3)	H28B—C28—H28C	109.5
C13—C12—C11	119.7 (3)	C30—C29—C34	117.4 (3)
C13—C12—C9	130.9 (3)	C30—C29—C7	122.9 (3)
C11—C12—C9	109.0 (3)	C34—C29—C7	119.5 (3)
C12—C13—C14	118.7 (3)	C29—C30—C31	121.7 (3)
C12—C13—H13	120.6	C29—C30—H30	119.1
C14—C13—H13	120.6	C31—C30—H30	119.1
C15—C14—C13	121.0 (3)	C32—C31—C30	119.3 (3)
C15—C14—H14	119.5	C32—C31—H31	120.3
C13—C14—H14	119.5	C30—C31—H31	120.3
C14—C15—C16	121.1 (3)	C31—C32—C33	119.7 (3)
C14—C15—H15	119.5	C31—C32—O4	124.6 (3)
C16—C15—H15	119.5	C33—C32—O4	115.7 (3)
C11—C16—C15	117.6 (3)	C34—C33—C32	120.5 (3)
C11—C16—H16	121.2	C34—C33—H33	119.7
C15—C16—H16	121.2	C32—C33—H33	119.7
C36—C17—C4	120.1 (3)	C33—C34—C29	121.3 (3)
C36—C17—C18	123.2 (3)	C33—C34—H34	119.3
C4—C17—C18	116.3 (3)	C29—C34—H34	119.3
C19—C18—C17	117.6 (3)	O4—C35—H35A	109.5
C19—C18—H18A	107.9	O4—C35—H35B	109.5
C17—C18—H18A	107.9	H35A—C35—H35B	109.5
C19—C18—H18B	107.9	O4—C35—H35C	109.5
C17—C18—H18B	107.9	H35A—C35—H35C	109.5
H18A—C18—H18B	107.2	H35B—C35—H35C	109.5
C18—C19—C20	114.1 (3)	C17—C36—C37	127.3 (3)
C18—C19—C20'	108.2 (4)	C17—C36—H36	116.4
C20—C19—C20'	47.9 (3)	C37—C36—H36	116.4
C18—C19—H19A	108.9	C42—C37—C38	116.6 (3)
C20—C19—H19A	108.1	C42—C37—C36	121.9 (3)
C20'—C19—H19A	65.4	C38—C37—C36	121.4 (3)
C18—C19—H19B	108.7	C37—C38—C39	122.0 (3)
C20—C19—H19B	109.2	C37—C38—H38	119.0
C20'—C19—H19B	142.5	C39—C38—H38	119.0
H19A—C19—H19B	107.8	C40—C39—C38	119.4 (3)
C18—C19—H19C	109.8	C40—C39—H39	120.3
C20—C19—H19C	135.4	C38—C39—H39	120.3
C20'—C19—H19C	110.3	C41—C40—C39	120.2 (3)
H19A—C19—H19C	48.0	C41—C40—O5	115.0 (3)
H19B—C19—H19C	62.0	C39—C40—O5	124.8 (3)
C18—C19—H19D	110.4	C40—C41—C42	119.5 (3)
C20—C19—H19D	63.0	C40—C41—H41	120.2
C20'—C19—H19D	109.6	C42—C41—H41	120.2
H19A—C19—H19D	139.7	C37—C42—C41	122.2 (3)
H19B—C19—H19D	50.2	C37—C42—H42	118.9
H19C—C19—H19D	108.5	C41—C42—H42	118.9
C21—C20—C19	116.2 (5)	O5—C43—H43A	109.5
C21—C20—H19D	146.3	O5—C43—H43B	109.5
C19—C20—H19D	37.5	H43A—C43—H43B	109.5
C21—C20—H20A	108.2	O5—C43—H43C	109.5
C19—C20—H20A	108.2	H43A—C43—H43C	109.5
H19D—C20—H20A	75.4	H43B—C43—H43C	109.5
C21—C20—H20B	108.2	N3—C44—H44A	109.5
C19—C20—H20B	108.2	N3—C44—H44B	109.5
H19D—C20—H20B	102.0	H44A—C44—H44B	109.5
H20A—C20—H20B	107.4	N3—C44—H44C	109.5
C21—C20—H21C	41.8	H44A—C44—H44C	109.5
C19—C20—H21C	154.5	H44B—C44—H44C	109.5
H19D—C20—H21C	150.5
C3—S1—C1—C2	−2.84 (19)	C10—C9—C12—C11	−7.2 (3)
C3—S1—C1—C7	−121.90 (19)	C1—C9—C12—C11	113.4 (3)
C3—S1—C1—C9	121.79 (19)	C11—C12—C13—C14	−2.3 (4)
C3—N1—C2—O1	178.2 (2)	C9—C12—C13—C14	−173.7 (3)
C6—N1—C2—O1	4.3 (4)	C12—C13—C14—C15	0.1 (5)
C3—N1—C2—C1	0.8 (3)	C13—C14—C15—C16	1.5 (5)
C6—N1—C2—C1	−173.0 (2)	C12—C11—C16—C15	−1.5 (5)
C7—C1—C2—O1	−53.7 (3)	N4—C11—C16—C15	172.1 (3)
C9—C1—C2—O1	60.7 (3)	C14—C15—C16—C11	−0.8 (5)
S1—C1—C2—O1	−175.6 (2)	C5—C4—C17—C36	150.6 (3)
C7—C1—C2—N1	123.6 (2)	N2—C4—C17—C36	−31.5 (4)
C9—C1—C2—N1	−122.0 (2)	C5—C4—C17—C18	−36.2 (4)
S1—C1—C2—N1	1.7 (3)	N2—C4—C17—C18	141.8 (3)
C4—N2—C3—N1	−2.5 (4)	C36—C17—C18—C19	−110.9 (4)
C4—N2—C3—S1	174.39 (19)	C4—C17—C18—C19	76.0 (4)
C2—N1—C3—N2	174.0 (3)	C17—C18—C19—C20	−30.4 (5)
C6—N1—C3—N2	−12.0 (4)	C17—C18—C19—C20'	−81.7 (5)
C2—N1—C3—S1	−3.1 (3)	C18—C19—C20—C21	−50.5 (7)
C6—N1—C3—S1	170.84 (19)	C20'—C19—C20—C21	42.9 (5)
C1—S1—C3—N2	−173.7 (2)	C18—C19—C20'—C21	65.1 (6)
C1—S1—C3—N1	3.5 (2)	C20—C19—C20'—C21	−41.2 (5)
C3—N2—C4—C5	8.4 (4)	C19—C20—C21—C20'	−43.5 (5)
C3—N2—C4—C17	−169.6 (2)	C19—C20—C21—C5	72.4 (7)
N2—C4—C5—C21	175.0 (3)	C19—C20'—C21—C20	42.4 (5)
C17—C4—C5—C21	−7.3 (5)	C19—C20'—C21—C5	−58.7 (8)
N2—C4—C5—C6	0.4 (4)	C4—C5—C21—C20	−18.6 (6)
C17—C4—C5—C6	178.2 (3)	C6—C5—C21—C20	156.5 (4)
C2—N1—C6—C5	−167.9 (2)	C4—C5—C21—C20'	44.4 (7)
C3—N1—C6—C5	18.5 (3)	C6—C5—C21—C20'	−140.6 (5)
C2—N1—C6—C22	66.3 (3)	N1—C6—C22—C27	−104.0 (3)
C3—N1—C6—C22	−107.3 (3)	C5—C6—C22—C27	131.9 (3)
C4—C5—C6—N1	−13.0 (4)	N1—C6—C22—C23	78.8 (3)
C21—C5—C6—N1	171.6 (3)	C5—C6—C22—C23	−45.3 (4)
C4—C5—C6—C22	112.0 (3)	C27—C22—C23—C24	0.9 (5)
C21—C5—C6—C22	−63.4 (3)	C6—C22—C23—C24	178.1 (3)
C2—C1—C7—C8	149.5 (2)	C22—C23—C24—C25	−0.6 (5)
C9—C1—C7—C8	28.0 (3)	C28—O3—C25—C26	3.4 (5)
S1—C1—C7—C8	−93.8 (2)	C28—O3—C25—C24	−177.4 (3)
C2—C1—C7—C29	−79.6 (3)	C23—C24—C25—C26	0.1 (5)
C9—C1—C7—C29	158.9 (2)	C23—C24—C25—O3	−179.1 (3)
S1—C1—C7—C29	37.1 (3)	O3—C25—C26—C27	179.2 (3)
C44—N3—C8—C7	178.1 (2)	C24—C25—C26—C27	0.1 (5)
C9—N3—C8—C7	46.5 (3)	C23—C22—C27—C26	−0.7 (4)
C29—C7—C8—N3	−175.5 (2)	C6—C22—C27—C26	−178.0 (3)
C1—C7—C8—N3	−44.9 (3)	C25—C26—C27—C22	0.2 (5)
C8—N3—C9—C12	−156.0 (2)	C8—C7—C29—C30	18.0 (4)
C44—N3—C9—C12	72.3 (3)	C1—C7—C29—C30	−105.4 (3)
C8—N3—C9—C10	90.8 (3)	C8—C7—C29—C34	−156.3 (3)
C44—N3—C9—C10	−40.9 (3)	C1—C7—C29—C34	80.3 (3)
C8—N3—C9—C1	−27.4 (3)	C34—C29—C30—C31	0.5 (4)
C44—N3—C9—C1	−159.2 (2)	C7—C29—C30—C31	−173.9 (3)
C2—C1—C9—N3	−119.4 (2)	C29—C30—C31—C32	0.0 (5)
C7—C1—C9—N3	−1.4 (3)	C30—C31—C32—C33	−1.0 (5)
S1—C1—C9—N3	121.06 (19)	C30—C31—C32—O4	178.8 (3)
C2—C1—C9—C12	4.3 (3)	C35—O4—C32—C31	−1.9 (5)
C7—C1—C9—C12	122.3 (2)	C35—O4—C32—C33	177.9 (3)
S1—C1—C9—C12	−115.2 (2)	C31—C32—C33—C34	1.6 (5)
C2—C1—C9—C10	120.5 (2)	O4—C32—C33—C34	−178.3 (3)
C7—C1—C9—C10	−121.5 (2)	C32—C33—C34—C29	−1.1 (5)
S1—C1—C9—C10	1.0 (3)	C30—C29—C34—C33	0.1 (4)
C11—N4—C10—O2	166.5 (3)	C7—C29—C34—C33	174.7 (3)
C11—N4—C10—C9	−10.5 (3)	C4—C17—C36—C37	−178.2 (3)
N3—C9—C10—O2	−47.3 (4)	C18—C17—C36—C37	9.0 (5)
C12—C9—C10—O2	−166.5 (3)	C17—C36—C37—C42	49.0 (5)
C1—C9—C10—O2	66.7 (4)	C17—C36—C37—C38	−134.7 (3)
N3—C9—C10—N4	129.7 (2)	C42—C37—C38—C39	−1.2 (5)
C12—C9—C10—N4	10.5 (3)	C36—C37—C38—C39	−177.7 (3)
C1—C9—C10—N4	−116.3 (3)	C37—C38—C39—C40	1.9 (5)
C10—N4—C11—C16	−168.2 (3)	C38—C39—C40—C41	−0.9 (5)
C10—N4—C11—C12	6.0 (4)	C38—C39—C40—O5	179.6 (3)
C16—C11—C12—C13	3.1 (4)	C43—O5—C40—C41	170.5 (4)
N4—C11—C12—C13	−171.5 (3)	C43—O5—C40—C39	−9.9 (6)
C16—C11—C12—C9	176.2 (3)	C39—C40—C41—C42	−0.6 (6)
N4—C11—C12—C9	1.6 (3)	O5—C40—C41—C42	179.0 (3)
N3—C9—C12—C13	44.9 (4)	C38—C37—C42—C41	−0.4 (5)
C10—C9—C12—C13	164.9 (3)	C36—C37—C42—C41	176.1 (3)
C1—C9—C12—C13	−74.5 (4)	C40—C41—C42—C37	1.3 (6)
N3—C9—C12—C11	−127.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2^i	0.86 (1)	2.16 (1)	3.014 (3)	173 (3)

Symmetry code: (i) −x+1, −y, −z.