2′-Benzo­yl-1′-(4-chloro­phen­yl)-5′,6′,7′,7a′-tetra­hydro­spiro­[indan-2,3′(2′H)-1H-pyrrolizine]-1,3-dione

The title compound, C₂₈H₂₂ClNO₃, has two crystallographically independent mol­ecules in the asymmetric unit. The pyrrolidine ring (A) of the pyrrolizine system adopts an envelope conformation in both mol­ecules, whereas the other five-membered ring (B) adopts an envelope conformation in one mol­ecule and a twist conformation in the other. The mol­ecular packing is stabilized by inter­molecular C—H...O, C—H...π and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.046
• wR factor = 0.143
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C17A
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3A    ..  C27B    ..       2.96 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C28 H22 Cl N O3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

2'-Benzoyl-1'-(4-chlorophenyl)-5',6',7',7a'-tetrahydrospiro[indan- 2,3'(2'H)-1H-pyrrolizidine]-1,3-dione

Crystal data

C28H22ClNO3	Z = 4
Mr = 455.92	F(000) = 952
Triclinic, P1	Dx = 1.306 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2023 (5) Å	Cell parameters from 9937 reflections
b = 11.7111 (7) Å	θ = 2.5–28.0°
c = 25.4650 (15) Å	µ = 0.20 mm^−1
α = 102.102 (1)°	T = 273 K
β = 90.014 (1)°	Block, yellow
γ = 103.949 (1)°	0.22 × 0.20 × 0.18 mm
V = 2317.9 (2) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	8360 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.016
Graphite monochromator	θmax = 28.0°, θmin = 0.8°
ω scans	h = −10→10
20028 measured reflections	k = −15→15
10374 independent reflections	l = −32→32

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.143	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0907P)^2 + 0.2136P] where P = (Fo^2 + 2Fc^2)/3
10374 reflections	(Δ/σ)max < 0.001
595 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

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
Cl1A	0.66669 (7)	0.43046 (4)	0.43611 (2)	0.08070 (17)
N1A	−0.22692 (14)	−0.07446 (11)	0.35716 (4)	0.0424 (3)
C1A	−0.11714 (18)	0.04847 (13)	0.37343 (5)	0.0429 (3)
H1A	−0.0734	0.0783	0.3417	0.051*
C2A	0.02802 (17)	0.03523 (12)	0.40857 (5)	0.0382 (3)
H2A	−0.0127	0.0289	0.4443	0.046*
C3A	0.05763 (16)	−0.08732 (11)	0.38027 (5)	0.0368 (3)
H3A	0.1436	−0.0718	0.3542	0.044*
C4A	−0.11178 (16)	−0.15574 (12)	0.34771 (5)	0.0375 (3)
C5A	−0.3448 (2)	−0.08664 (17)	0.40117 (7)	0.0583 (4)
H5A1	−0.2911	−0.1011	0.4323	0.070*
H5A2	−0.4446	−0.1514	0.3893	0.070*
C6A	−0.3869 (3)	0.03500 (19)	0.41351 (9)	0.0736 (5)
H6A1	−0.4820	0.0342	0.3907	0.088*
H6A2	−0.4145	0.0554	0.4508	0.088*
C7A	−0.2314 (2)	0.12476 (16)	0.40254 (7)	0.0602 (4)
H7A1	−0.1762	0.1759	0.4359	0.072*
H7A2	−0.2603	0.1752	0.3801	0.072*
C8A	0.18468 (17)	0.13768 (12)	0.41529 (5)	0.0398 (3)
C9A	0.2482 (2)	0.20282 (13)	0.46615 (6)	0.0493 (3)
H9A	0.1910	0.1855	0.4962	0.059*
C10A	0.3957 (2)	0.29324 (14)	0.47293 (6)	0.0573 (4)
H10A	0.4378	0.3360	0.5072	0.069*
C11A	0.4786 (2)	0.31892 (13)	0.42851 (7)	0.0521 (4)
C12A	0.4171 (2)	0.25819 (13)	0.37732 (6)	0.0500 (3)
H12A	0.4734	0.2777	0.3475	0.060*
C13A	0.27036 (19)	0.16780 (13)	0.37106 (6)	0.0455 (3)
H13A	0.2281	0.1264	0.3366	0.055*
C14A	0.12133 (19)	−0.15415 (13)	0.41782 (6)	0.0447 (3)
C15A	0.1677 (2)	−0.26919 (14)	0.39358 (6)	0.0507 (3)
C16A	0.1744 (3)	−0.34880 (19)	0.42659 (9)	0.0787 (6)
H16A	0.1551	−0.3287	0.4630	0.094*
C17A	0.2105 (4)	−0.4592 (2)	0.40478 (12)	0.1021 (8)
H17A	0.2140	−0.5130	0.4267	0.123*
C18A	0.2405 (4)	−0.4884 (2)	0.35163 (12)	0.0934 (7)
H18A	0.2632	−0.5625	0.3374	0.112*
C19A	0.2377 (3)	−0.41002 (19)	0.31909 (10)	0.0804 (6)
H19A	0.2606	−0.4300	0.2830	0.096*
C20A	0.2003 (2)	−0.29994 (15)	0.33995 (7)	0.0584 (4)
H20A	0.1973	−0.2469	0.3176	0.070*
C21A	−0.20066 (18)	−0.28112 (13)	0.35670 (6)	0.0429 (3)
C22A	−0.25469 (18)	−0.36123 (13)	0.30301 (6)	0.0445 (3)
C23A	−0.3498 (2)	−0.47967 (15)	0.29097 (7)	0.0577 (4)
H23A	−0.3900	−0.5197	0.3181	0.069*
C24A	−0.3825 (2)	−0.53601 (16)	0.23745 (8)	0.0657 (5)
H24A	−0.4467	−0.6152	0.2283	0.079*
C25A	−0.3217 (2)	−0.47691 (17)	0.19692 (7)	0.0639 (5)
H25A	−0.3459	−0.5175	0.1612	0.077*
C26A	−0.2260 (2)	−0.35944 (16)	0.20832 (6)	0.0537 (4)
H26A	−0.1843	−0.3203	0.1811	0.064*
C27A	−0.19455 (17)	−0.30195 (13)	0.26254 (5)	0.0426 (3)
C28A	−0.09329 (17)	−0.17922 (12)	0.28631 (5)	0.0399 (3)
O1A	0.13416 (18)	−0.11540 (11)	0.46612 (4)	0.0664 (3)
O2A	−0.22201 (16)	−0.30803 (11)	0.39972 (4)	0.0604 (3)
O3A	−0.01014 (14)	−0.10757 (10)	0.26281 (4)	0.0538 (3)
Cl1B	0.20786 (9)	0.50129 (5)	−0.05544 (2)	0.08673 (18)
N1B	−0.00470 (15)	0.12032 (11)	0.17556 (5)	0.0450 (3)
C1B	0.0118 (2)	0.23394 (13)	0.15727 (6)	0.0480 (3)
H1B	−0.0771	0.2226	0.1296	0.058*
C2B	0.18360 (18)	0.25917 (12)	0.13228 (5)	0.0420 (3)
H2B	0.2673	0.3108	0.1601	0.050*
C3B	0.21935 (16)	0.13341 (12)	0.11821 (5)	0.0384 (3)
H3B	0.1528	0.0874	0.0853	0.046*
C4B	0.14604 (17)	0.07689 (12)	0.16636 (5)	0.0395 (3)
C5B	−0.0752 (2)	0.13122 (18)	0.22895 (7)	0.0637 (4)
H5B1	0.0106	0.1387	0.2566	0.076*
H5B2	−0.1664	0.0615	0.2300	0.076*
C6B	−0.1391 (3)	0.24459 (19)	0.23692 (9)	0.0780 (6)
H6B1	−0.1358	0.2825	0.2748	0.094*
H6B2	−0.2532	0.2272	0.2218	0.094*
C7B	−0.0171 (3)	0.32356 (17)	0.20681 (9)	0.0774 (6)
H7B1	0.0870	0.3629	0.2281	0.093*
H7B2	−0.0658	0.3843	0.1970	0.093*
C8B	0.18914 (18)	0.31931 (13)	0.08523 (5)	0.0421 (3)
C9B	0.2934 (2)	0.43220 (15)	0.08745 (7)	0.0570 (4)
H9B	0.3607	0.4711	0.1185	0.068*
C10B	0.3005 (3)	0.48912 (16)	0.04465 (8)	0.0667 (5)
H10B	0.3721	0.5650	0.0468	0.080*
C11B	0.2004 (2)	0.43195 (15)	−0.00091 (6)	0.0547 (4)
C12B	0.0939 (2)	0.32002 (15)	−0.00455 (6)	0.0556 (4)
H12B	0.0262	0.2820	−0.0356	0.067*
C13B	0.0886 (2)	0.26480 (14)	0.03840 (6)	0.0516 (3)
H13B	0.0160	0.1892	0.0360	0.062*
C14B	0.40336 (17)	0.13316 (13)	0.10992 (5)	0.0426 (3)
C15B	0.44321 (17)	0.01847 (13)	0.08143 (5)	0.0419 (3)
C16B	0.5949 (2)	−0.00456 (16)	0.09513 (7)	0.0553 (4)
H16B	0.6683	0.0504	0.1217	0.066*
C17B	0.6363 (2)	−0.10932 (18)	0.06917 (8)	0.0661 (5)
H17B	0.7364	−0.1254	0.0789	0.079*
C18B	0.5300 (2)	−0.18964 (16)	0.02906 (8)	0.0622 (4)
H18B	0.5592	−0.2593	0.0114	0.075*
C19B	0.3811 (2)	−0.16728 (15)	0.01509 (7)	0.0571 (4)
H19B	0.3096	−0.2215	−0.0122	0.068*
C20B	0.33742 (18)	−0.06405 (14)	0.04162 (6)	0.0470 (3)
H20B	0.2352	−0.0501	0.0325	0.056*
C21B	0.27955 (18)	0.11051 (13)	0.21376 (5)	0.0431 (3)
C22B	0.33667 (17)	0.00143 (14)	0.21657 (6)	0.0440 (3)
C23B	0.4621 (2)	−0.01075 (18)	0.25026 (7)	0.0594 (4)
H23B	0.5242	0.0552	0.2753	0.071*
C24B	0.4912 (3)	−0.1223 (2)	0.24556 (9)	0.0763 (6)
H24B	0.5738	−0.1324	0.2679	0.092*
C25B	0.4003 (3)	−0.2204 (2)	0.20812 (9)	0.0766 (6)
H25B	0.4248	−0.2949	0.2054	0.092*
C26B	0.2734 (2)	−0.21084 (16)	0.17445 (7)	0.0594 (4)
H26B	0.2118	−0.2771	0.1495	0.071*
C27B	0.24299 (17)	−0.09749 (13)	0.17992 (6)	0.0430 (3)
C28B	0.11310 (17)	−0.06177 (12)	0.15110 (5)	0.0409 (3)
O1B	0.51398 (14)	0.22168 (11)	0.12824 (5)	0.0636 (3)
O2B	0.32653 (16)	0.20914 (10)	0.24315 (4)	0.0605 (3)
O3B	0.00150 (14)	−0.12837 (10)	0.12091 (5)	0.0575 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1A	0.0813 (3)	0.0490 (2)	0.0950 (4)	−0.0108 (2)	−0.0012 (3)	0.0095 (2)
N1A	0.0411 (6)	0.0490 (6)	0.0400 (6)	0.0166 (5)	0.0010 (5)	0.0100 (5)
C1A	0.0478 (7)	0.0460 (7)	0.0396 (7)	0.0195 (6)	0.0001 (6)	0.0104 (6)
C2A	0.0446 (7)	0.0396 (7)	0.0326 (6)	0.0154 (5)	0.0013 (5)	0.0067 (5)
C3A	0.0394 (6)	0.0376 (6)	0.0346 (6)	0.0125 (5)	0.0014 (5)	0.0069 (5)
C4A	0.0409 (6)	0.0401 (7)	0.0328 (6)	0.0119 (5)	0.0015 (5)	0.0086 (5)
C5A	0.0472 (8)	0.0724 (11)	0.0616 (9)	0.0226 (8)	0.0128 (7)	0.0194 (8)
C6A	0.0668 (11)	0.0875 (13)	0.0807 (13)	0.0440 (10)	0.0200 (10)	0.0206 (10)
C7A	0.0679 (10)	0.0624 (10)	0.0596 (9)	0.0383 (9)	0.0004 (8)	0.0076 (8)
C8A	0.0475 (7)	0.0366 (6)	0.0377 (6)	0.0165 (5)	−0.0002 (5)	0.0063 (5)
C9A	0.0617 (9)	0.0467 (8)	0.0376 (7)	0.0127 (7)	0.0019 (6)	0.0055 (6)
C10A	0.0715 (10)	0.0454 (8)	0.0465 (8)	0.0086 (7)	−0.0074 (7)	−0.0018 (6)
C11A	0.0574 (9)	0.0329 (7)	0.0636 (9)	0.0085 (6)	−0.0020 (7)	0.0078 (6)
C12A	0.0601 (9)	0.0429 (7)	0.0505 (8)	0.0137 (7)	0.0064 (7)	0.0165 (6)
C13A	0.0546 (8)	0.0445 (7)	0.0384 (7)	0.0143 (6)	−0.0003 (6)	0.0086 (6)
C14A	0.0486 (8)	0.0468 (7)	0.0421 (7)	0.0174 (6)	−0.0024 (6)	0.0106 (6)
C15A	0.0528 (8)	0.0491 (8)	0.0557 (8)	0.0229 (7)	−0.0044 (7)	0.0112 (7)
C16A	0.1105 (17)	0.0715 (12)	0.0718 (12)	0.0479 (12)	0.0008 (11)	0.0251 (10)
C17A	0.147 (2)	0.0766 (14)	0.111 (2)	0.0649 (16)	0.0076 (17)	0.0391 (14)
C18A	0.1164 (19)	0.0627 (12)	0.1136 (19)	0.0535 (13)	0.0008 (15)	0.0104 (12)
C19A	0.0969 (15)	0.0673 (12)	0.0834 (14)	0.0443 (11)	0.0094 (11)	0.0029 (10)
C20A	0.0634 (10)	0.0553 (9)	0.0619 (10)	0.0282 (8)	0.0029 (8)	0.0085 (7)
C21A	0.0441 (7)	0.0445 (7)	0.0416 (7)	0.0108 (6)	0.0037 (6)	0.0128 (6)
C22A	0.0431 (7)	0.0438 (7)	0.0459 (7)	0.0112 (6)	0.0001 (6)	0.0079 (6)
C23A	0.0559 (9)	0.0462 (8)	0.0673 (10)	0.0056 (7)	0.0023 (8)	0.0123 (7)
C24A	0.0593 (10)	0.0470 (9)	0.0779 (12)	0.0055 (7)	−0.0084 (9)	−0.0056 (8)
C25A	0.0642 (10)	0.0634 (10)	0.0540 (9)	0.0171 (8)	−0.0105 (8)	−0.0113 (8)
C26A	0.0549 (9)	0.0626 (9)	0.0414 (7)	0.0177 (7)	−0.0014 (6)	0.0026 (7)
C27A	0.0421 (7)	0.0460 (7)	0.0398 (7)	0.0145 (6)	−0.0004 (5)	0.0051 (6)
C28A	0.0425 (7)	0.0447 (7)	0.0350 (6)	0.0148 (6)	0.0025 (5)	0.0097 (5)
O1A	0.0973 (9)	0.0702 (8)	0.0405 (6)	0.0401 (7)	−0.0097 (6)	0.0085 (5)
O2A	0.0776 (8)	0.0582 (7)	0.0454 (6)	0.0069 (6)	0.0084 (5)	0.0225 (5)
O3A	0.0645 (7)	0.0540 (6)	0.0421 (5)	0.0076 (5)	0.0102 (5)	0.0170 (5)
Cl1B	0.1270 (5)	0.0907 (4)	0.0622 (3)	0.0421 (3)	0.0217 (3)	0.0424 (3)
N1B	0.0445 (6)	0.0468 (6)	0.0490 (6)	0.0170 (5)	0.0070 (5)	0.0156 (5)
C1B	0.0518 (8)	0.0482 (8)	0.0513 (8)	0.0209 (6)	0.0082 (6)	0.0168 (6)
C2B	0.0460 (7)	0.0412 (7)	0.0388 (6)	0.0118 (6)	−0.0008 (5)	0.0076 (5)
C3B	0.0390 (6)	0.0408 (7)	0.0354 (6)	0.0113 (5)	−0.0019 (5)	0.0067 (5)
C4B	0.0400 (7)	0.0404 (7)	0.0383 (6)	0.0111 (5)	−0.0019 (5)	0.0080 (5)
C5B	0.0654 (10)	0.0771 (12)	0.0622 (10)	0.0308 (9)	0.0244 (8)	0.0301 (9)
C6B	0.0954 (15)	0.0777 (13)	0.0722 (12)	0.0397 (11)	0.0351 (11)	0.0198 (10)
C7B	0.0975 (15)	0.0556 (10)	0.0844 (13)	0.0332 (10)	0.0374 (12)	0.0104 (9)
C8B	0.0441 (7)	0.0426 (7)	0.0416 (7)	0.0138 (6)	0.0018 (5)	0.0096 (6)
C9B	0.0634 (10)	0.0497 (8)	0.0533 (9)	0.0036 (7)	−0.0086 (7)	0.0128 (7)
C10B	0.0764 (12)	0.0514 (9)	0.0700 (11)	0.0026 (8)	0.0021 (9)	0.0235 (8)
C11B	0.0682 (10)	0.0594 (9)	0.0475 (8)	0.0279 (8)	0.0139 (7)	0.0214 (7)
C12B	0.0673 (10)	0.0587 (9)	0.0428 (8)	0.0214 (8)	−0.0044 (7)	0.0084 (7)
C13B	0.0561 (9)	0.0444 (8)	0.0520 (8)	0.0078 (7)	−0.0063 (7)	0.0108 (6)
C14B	0.0398 (7)	0.0497 (8)	0.0370 (6)	0.0094 (6)	−0.0008 (5)	0.0083 (6)
C15B	0.0383 (7)	0.0490 (7)	0.0407 (7)	0.0118 (6)	0.0056 (5)	0.0137 (6)
C16B	0.0422 (8)	0.0684 (10)	0.0572 (9)	0.0148 (7)	−0.0022 (7)	0.0163 (8)
C17B	0.0496 (9)	0.0792 (12)	0.0830 (12)	0.0318 (9)	0.0066 (8)	0.0288 (10)
C18B	0.0600 (10)	0.0529 (9)	0.0805 (12)	0.0245 (8)	0.0193 (9)	0.0172 (8)
C19B	0.0519 (9)	0.0518 (9)	0.0624 (10)	0.0115 (7)	0.0071 (7)	0.0026 (7)
C20B	0.0388 (7)	0.0533 (8)	0.0494 (8)	0.0144 (6)	0.0028 (6)	0.0084 (6)
C21B	0.0437 (7)	0.0486 (8)	0.0348 (6)	0.0056 (6)	−0.0006 (5)	0.0112 (6)
C22B	0.0369 (6)	0.0578 (8)	0.0397 (7)	0.0105 (6)	0.0024 (5)	0.0171 (6)
C23B	0.0454 (8)	0.0849 (12)	0.0520 (9)	0.0168 (8)	−0.0038 (7)	0.0230 (8)
C24B	0.0619 (11)	0.1069 (16)	0.0781 (12)	0.0400 (11)	−0.0069 (9)	0.0371 (12)
C25B	0.0779 (13)	0.0787 (13)	0.0933 (14)	0.0455 (11)	0.0014 (11)	0.0327 (11)
C26B	0.0626 (10)	0.0548 (9)	0.0682 (10)	0.0246 (8)	0.0022 (8)	0.0182 (8)
C27B	0.0400 (7)	0.0485 (7)	0.0452 (7)	0.0140 (6)	0.0034 (6)	0.0167 (6)
C28B	0.0393 (7)	0.0424 (7)	0.0414 (7)	0.0109 (5)	0.0008 (5)	0.0091 (5)
O1B	0.0466 (6)	0.0573 (7)	0.0730 (8)	0.0023 (5)	−0.0023 (5)	−0.0046 (6)
O2B	0.0746 (8)	0.0527 (6)	0.0443 (6)	0.0035 (6)	−0.0115 (5)	0.0026 (5)
O3B	0.0528 (6)	0.0487 (6)	0.0643 (7)	0.0096 (5)	−0.0176 (5)	0.0012 (5)

Geometric parameters (Å, º)

Cl1A—C11A	1.7452 (16)	Cl1B—C11B	1.7435 (16)
N1A—C1A	1.4764 (19)	N1B—C4B	1.4477 (18)
N1A—C4A	1.4810 (17)	N1B—C5B	1.470 (2)
N1A—C5A	1.4874 (19)	N1B—C1B	1.4762 (18)
C1A—C7A	1.534 (2)	C1B—C7B	1.521 (2)
C1A—C2A	1.5457 (18)	C1B—C2B	1.535 (2)
C1A—H1A	0.9800	C1B—H1B	0.9800
C2A—C8A	1.5134 (19)	C2B—C8B	1.5075 (19)
C2A—C3A	1.5404 (17)	C2B—C3B	1.5396 (18)
C2A—H2A	0.9800	C2B—H2B	0.9800
C3A—C14A	1.5202 (18)	C3B—C14B	1.5247 (19)
C3A—C4A	1.5635 (18)	C3B—C4B	1.5658 (18)
C3A—H3A	0.9800	C3B—H3B	0.9800
C4A—C21A	1.5378 (19)	C4B—C28B	1.5443 (19)
C4A—C28A	1.5438 (17)	C4B—C21B	1.5502 (18)
C5A—C6A	1.515 (3)	C5B—C6B	1.517 (3)
C5A—H5A1	0.9700	C5B—H5B1	0.9700
C5A—H5A2	0.9700	C5B—H5B2	0.9700
C6A—C7A	1.512 (3)	C6B—C7B	1.515 (3)
C6A—H6A1	0.9700	C6B—H6B1	0.9700
C6A—H6A2	0.9700	C6B—H6B2	0.9700
C7A—H7A1	0.9700	C7B—H7B1	0.9700
C7A—H7A2	0.9700	C7B—H7B2	0.9700
C8A—C9A	1.3874 (19)	C8B—C9B	1.381 (2)
C8A—C13A	1.391 (2)	C8B—C13B	1.392 (2)
C9A—C10A	1.385 (2)	C9B—C10B	1.386 (2)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.370 (2)	C10B—C11B	1.370 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.377 (2)	C11B—C12B	1.374 (2)
C12A—C13A	1.382 (2)	C12B—C13B	1.378 (2)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—O1A	1.2135 (17)	C14B—O1B	1.2080 (17)
C14A—C15A	1.496 (2)	C14B—C15B	1.497 (2)
C15A—C20A	1.381 (2)	C15B—C20B	1.378 (2)
C15A—C16A	1.390 (2)	C15B—C16B	1.394 (2)
C16A—C17A	1.397 (3)	C16B—C17B	1.385 (3)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.362 (4)	C17B—C18B	1.374 (3)
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—C19A	1.363 (3)	C18B—C19B	1.371 (3)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—C20A	1.393 (2)	C19B—C20B	1.383 (2)
C19A—H19A	0.9300	C19B—H19B	0.9300
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—O2A	1.2034 (17)	C21B—O2B	1.2106 (18)
C21A—C22A	1.486 (2)	C21B—C22B	1.478 (2)
C22A—C27A	1.386 (2)	C22B—C27B	1.386 (2)
C22A—C23A	1.388 (2)	C22B—C23B	1.391 (2)
C23A—C24A	1.379 (3)	C23B—C24B	1.364 (3)
C23A—H23A	0.9300	C23B—H23B	0.9300
C24A—C25A	1.388 (3)	C24B—C25B	1.383 (3)
C24A—H24A	0.9300	C24B—H24B	0.9300
C25A—C26A	1.380 (3)	C25B—C26B	1.389 (3)
C25A—H25A	0.9300	C25B—H25B	0.9300
C26A—C27A	1.3973 (19)	C26B—C27B	1.388 (2)
C26A—H26A	0.9300	C26B—H26B	0.9300
C27A—C28A	1.477 (2)	C27B—C28B	1.4804 (19)
C28A—O3A	1.2091 (17)	C28B—O3B	1.2006 (17)
C1A—N1A—C4A	105.53 (10)	C4B—N1B—C5B	119.76 (12)
C1A—N1A—C5A	105.07 (11)	C4B—N1B—C1B	110.97 (11)
C4A—N1A—C5A	117.59 (11)	C5B—N1B—C1B	109.57 (12)
N1A—C1A—C7A	104.82 (12)	N1B—C1B—C7B	104.68 (13)
N1A—C1A—C2A	104.81 (10)	N1B—C1B—C2B	106.00 (11)
C7A—C1A—C2A	115.65 (12)	C7B—C1B—C2B	118.23 (15)
N1A—C1A—H1A	110.4	N1B—C1B—H1B	109.2
C7A—C1A—H1A	110.4	C7B—C1B—H1B	109.2
C2A—C1A—H1A	110.4	C2B—C1B—H1B	109.2
C8A—C2A—C3A	113.40 (11)	C8B—C2B—C1B	114.52 (12)
C8A—C2A—C1A	114.79 (11)	C8B—C2B—C3B	114.04 (11)
C3A—C2A—C1A	102.95 (10)	C1B—C2B—C3B	102.50 (11)
C8A—C2A—H2A	108.5	C8B—C2B—H2B	108.5
C3A—C2A—H2A	108.5	C1B—C2B—H2B	108.5
C1A—C2A—H2A	108.5	C3B—C2B—H2B	108.5
C14A—C3A—C2A	114.12 (11)	C14B—C3B—C2B	115.03 (11)
C14A—C3A—C4A	115.63 (11)	C14B—C3B—C4B	113.53 (11)
C2A—C3A—C4A	104.56 (10)	C2B—C3B—C4B	102.49 (10)
C14A—C3A—H3A	107.4	C14B—C3B—H3B	108.5
C2A—C3A—H3A	107.4	C2B—C3B—H3B	108.5
C4A—C3A—H3A	107.4	C4B—C3B—H3B	108.5
N1A—C4A—C21A	110.37 (11)	N1B—C4B—C28B	114.09 (11)
N1A—C4A—C28A	104.00 (10)	N1B—C4B—C21B	117.49 (11)
C21A—C4A—C28A	102.85 (10)	C28B—C4B—C21B	102.22 (11)
N1A—C4A—C3A	107.40 (10)	N1B—C4B—C3B	102.03 (10)
C21A—C4A—C3A	118.58 (11)	C28B—C4B—C3B	110.47 (11)
C28A—C4A—C3A	112.72 (11)	C21B—C4B—C3B	110.72 (11)
N1A—C5A—C6A	102.24 (14)	N1B—C5B—C6B	104.70 (14)
N1A—C5A—H5A1	111.3	N1B—C5B—H5B1	110.8
C6A—C5A—H5A1	111.3	C6B—C5B—H5B1	110.8
N1A—C5A—H5A2	111.3	N1B—C5B—H5B2	110.8
C6A—C5A—H5A2	111.3	C6B—C5B—H5B2	110.8
H5A1—C5A—H5A2	109.2	H5B1—C5B—H5B2	108.9
C7A—C6A—C5A	106.04 (14)	C5B—C6B—C7B	103.05 (15)
C7A—C6A—H6A1	110.5	C5B—C6B—H6B1	111.2
C5A—C6A—H6A1	110.5	C7B—C6B—H6B1	111.2
C7A—C6A—H6A2	110.5	C5B—C6B—H6B2	111.2
C5A—C6A—H6A2	110.5	C7B—C6B—H6B2	111.2
H6A1—C6A—H6A2	108.7	H6B1—C6B—H6B2	109.1
C6A—C7A—C1A	105.29 (14)	C6B—C7B—C1B	102.79 (15)
C6A—C7A—H7A1	110.7	C6B—C7B—H7B1	111.2
C1A—C7A—H7A1	110.7	C1B—C7B—H7B1	111.2
C6A—C7A—H7A2	110.7	C6B—C7B—H7B2	111.2
C1A—C7A—H7A2	110.7	C1B—C7B—H7B2	111.2
H7A1—C7A—H7A2	108.8	H7B1—C7B—H7B2	109.1
C9A—C8A—C13A	118.22 (13)	C9B—C8B—C13B	117.40 (14)
C9A—C8A—C2A	120.51 (13)	C9B—C8B—C2B	120.82 (13)
C13A—C8A—C2A	121.26 (12)	C13B—C8B—C2B	121.77 (13)
C10A—C9A—C8A	121.03 (14)	C8B—C9B—C10B	121.77 (15)
C10A—C9A—H9A	119.5	C8B—C9B—H9B	119.1
C8A—C9A—H9A	119.5	C10B—C9B—H9B	119.1
C11A—C10A—C9A	119.17 (14)	C11B—C10B—C9B	119.00 (16)
C11A—C10A—H10A	120.4	C11B—C10B—H10B	120.5
C9A—C10A—H10A	120.4	C9B—C10B—H10B	120.5
C10A—C11A—C12A	121.43 (15)	C10B—C11B—C12B	121.02 (15)
C10A—C11A—Cl1A	119.99 (13)	C10B—C11B—Cl1B	119.87 (14)
C12A—C11A—Cl1A	118.58 (13)	C12B—C11B—Cl1B	119.10 (13)
C11A—C12A—C13A	118.88 (14)	C11B—C12B—C13B	119.16 (15)
C11A—C12A—H12A	120.6	C11B—C12B—H12B	120.4
C13A—C12A—H12A	120.6	C13B—C12B—H12B	120.4
C12A—C13A—C8A	121.23 (13)	C12B—C13B—C8B	121.64 (15)
C12A—C13A—H13A	119.4	C12B—C13B—H13B	119.2
C8A—C13A—H13A	119.4	C8B—C13B—H13B	119.2
O1A—C14A—C15A	120.90 (13)	O1B—C14B—C15B	121.06 (13)
O1A—C14A—C3A	120.97 (13)	O1B—C14B—C3B	120.60 (13)
C15A—C14A—C3A	118.14 (12)	C15B—C14B—C3B	118.24 (11)
C20A—C15A—C16A	119.18 (16)	C20B—C15B—C16B	118.80 (14)
C20A—C15A—C14A	122.76 (14)	C20B—C15B—C14B	122.64 (12)
C16A—C15A—C14A	118.05 (15)	C16B—C15B—C14B	118.55 (13)
C15A—C16A—C17A	119.6 (2)	C17B—C16B—C15B	120.00 (15)
C15A—C16A—H16A	120.2	C17B—C16B—H16B	120.0
C17A—C16A—H16A	120.2	C15B—C16B—H16B	120.0
C18A—C17A—C16A	120.3 (2)	C18B—C17B—C16B	120.26 (15)
C18A—C17A—H17A	119.8	C18B—C17B—H17B	119.9
C16A—C17A—H17A	119.8	C16B—C17B—H17B	119.9
C19A—C18A—C17A	120.63 (19)	C19B—C18B—C17B	120.10 (16)
C19A—C18A—H18A	119.7	C19B—C18B—H18B	120.0
C17A—C18A—H18A	119.7	C17B—C18B—H18B	120.0
C18A—C19A—C20A	119.9 (2)	C18B—C19B—C20B	119.92 (16)
C18A—C19A—H19A	120.1	C18B—C19B—H19B	120.0
C20A—C19A—H19A	120.1	C20B—C19B—H19B	120.0
C15A—C20A—C19A	120.37 (18)	C15B—C20B—C19B	120.90 (14)
C15A—C20A—H20A	119.8	C15B—C20B—H20B	119.5
C19A—C20A—H20A	119.8	C19B—C20B—H20B	119.5
O2A—C21A—C22A	126.87 (13)	O2B—C21B—C22B	126.75 (13)
O2A—C21A—C4A	125.56 (13)	O2B—C21B—C4B	125.29 (14)
C22A—C21A—C4A	107.57 (11)	C22B—C21B—C4B	107.96 (11)
C27A—C22A—C23A	121.02 (14)	C27B—C22B—C23B	120.69 (15)
C27A—C22A—C21A	110.50 (12)	C27B—C22B—C21B	110.43 (12)
C23A—C22A—C21A	128.48 (14)	C23B—C22B—C21B	128.87 (15)
C24A—C23A—C22A	117.69 (16)	C24B—C23B—C22B	118.05 (17)
C24A—C23A—H23A	121.2	C24B—C23B—H23B	121.0
C22A—C23A—H23A	121.2	C22B—C23B—H23B	121.0
C23A—C24A—C25A	121.32 (16)	C23B—C24B—C25B	121.23 (16)
C23A—C24A—H24A	119.3	C23B—C24B—H24B	119.4
C25A—C24A—H24A	119.3	C25B—C24B—H24B	119.4
C26A—C25A—C24A	121.60 (15)	C24B—C25B—C26B	121.80 (18)
C26A—C25A—H25A	119.2	C24B—C25B—H25B	119.1
C24A—C25A—H25A	119.2	C26B—C25B—H25B	119.1
C25A—C26A—C27A	117.04 (16)	C27B—C26B—C25B	116.64 (17)
C25A—C26A—H26A	121.5	C27B—C26B—H26B	121.7
C27A—C26A—H26A	121.5	C25B—C26B—H26B	121.7
C22A—C27A—C26A	121.32 (14)	C22B—C27B—C26B	121.56 (14)
C22A—C27A—C28A	109.88 (12)	C22B—C27B—C28B	110.01 (12)
C26A—C27A—C28A	128.74 (14)	C26B—C27B—C28B	128.42 (14)
O3A—C28A—C27A	127.20 (12)	O3B—C28B—C27B	126.30 (13)
O3A—C28A—C4A	124.74 (12)	O3B—C28B—C4B	125.55 (12)
C27A—C28A—C4A	108.06 (11)	C27B—C28B—C4B	108.14 (11)
C4A—N1A—C1A—C7A	−159.68 (11)	C4B—N1B—C1B—C7B	−122.84 (15)
C5A—N1A—C1A—C7A	−34.74 (14)	C5B—N1B—C1B—C7B	11.63 (19)
C4A—N1A—C1A—C2A	−37.46 (13)	C4B—N1B—C1B—C2B	2.89 (16)
C5A—N1A—C1A—C2A	87.48 (12)	C5B—N1B—C1B—C2B	137.35 (13)
N1A—C1A—C2A—C8A	160.90 (10)	N1B—C1B—C2B—C8B	145.96 (12)
C7A—C1A—C2A—C8A	−84.23 (16)	C7B—C1B—C2B—C8B	−97.10 (18)
N1A—C1A—C2A—C3A	37.19 (13)	N1B—C1B—C2B—C3B	21.92 (14)
C7A—C1A—C2A—C3A	152.06 (13)	C7B—C1B—C2B—C3B	138.87 (15)
C8A—C2A—C3A—C14A	85.61 (14)	C8B—C2B—C3B—C14B	75.06 (15)
C1A—C2A—C3A—C14A	−149.76 (12)	C1B—C2B—C3B—C14B	−160.58 (11)
C8A—C2A—C3A—C4A	−147.10 (10)	C8B—C2B—C3B—C4B	−161.25 (11)
C1A—C2A—C3A—C4A	−22.47 (13)	C1B—C2B—C3B—C4B	−36.89 (12)
C1A—N1A—C4A—C21A	153.39 (10)	C5B—N1B—C4B—C28B	85.67 (16)
C5A—N1A—C4A—C21A	36.67 (16)	C1B—N1B—C4B—C28B	−145.11 (12)
C1A—N1A—C4A—C28A	−96.92 (11)	C5B—N1B—C4B—C21B	−33.94 (19)
C5A—N1A—C4A—C28A	146.36 (12)	C1B—N1B—C4B—C21B	95.29 (14)
C1A—N1A—C4A—C3A	22.77 (13)	C5B—N1B—C4B—C3B	−155.18 (13)
C5A—N1A—C4A—C3A	−93.96 (14)	C1B—N1B—C4B—C3B	−25.95 (14)
C14A—C3A—C4A—N1A	127.03 (12)	C14B—C3B—C4B—N1B	163.41 (11)
C2A—C3A—C4A—N1A	0.66 (13)	C2B—C3B—C4B—N1B	38.72 (12)
C14A—C3A—C4A—C21A	1.15 (17)	C14B—C3B—C4B—C28B	−74.91 (14)
C2A—C3A—C4A—C21A	−125.21 (12)	C2B—C3B—C4B—C28B	160.40 (11)
C14A—C3A—C4A—C28A	−119.02 (12)	C14B—C3B—C4B—C21B	37.59 (15)
C2A—C3A—C4A—C28A	114.61 (11)	C2B—C3B—C4B—C21B	−87.10 (13)
C1A—N1A—C5A—C6A	41.32 (15)	C4B—N1B—C5B—C6B	142.72 (16)
C4A—N1A—C5A—C6A	158.30 (13)	C1B—N1B—C5B—C6B	12.9 (2)
N1A—C5A—C6A—C7A	−31.82 (19)	N1B—C5B—C6B—C7B	−32.2 (2)
C5A—C6A—C7A—C1A	11.07 (19)	C5B—C6B—C7B—C1B	39.1 (2)
N1A—C1A—C7A—C6A	14.15 (16)	N1B—C1B—C7B—C6B	−31.3 (2)
C2A—C1A—C7A—C6A	−100.71 (16)	C2B—C1B—C7B—C6B	−149.00 (16)
C3A—C2A—C8A—C9A	−119.43 (14)	C1B—C2B—C8B—C9B	117.79 (16)
C1A—C2A—C8A—C9A	122.61 (14)	C3B—C2B—C8B—C9B	−124.58 (15)
C3A—C2A—C8A—C13A	59.43 (16)	C1B—C2B—C8B—C13B	−61.25 (18)
C1A—C2A—C8A—C13A	−58.52 (16)	C3B—C2B—C8B—C13B	56.38 (18)
C13A—C8A—C9A—C10A	−1.8 (2)	C13B—C8B—C9B—C10B	−0.9 (3)
C2A—C8A—C9A—C10A	177.11 (14)	C2B—C8B—C9B—C10B	179.98 (16)
C8A—C9A—C10A—C11A	0.5 (2)	C8B—C9B—C10B—C11B	0.4 (3)
C9A—C10A—C11A—C12A	1.1 (3)	C9B—C10B—C11B—C12B	0.1 (3)
C9A—C10A—C11A—Cl1A	−178.76 (12)	C9B—C10B—C11B—Cl1B	−179.65 (15)
C10A—C11A—C12A—C13A	−1.4 (2)	C10B—C11B—C12B—C13B	−0.2 (3)
Cl1A—C11A—C12A—C13A	178.49 (12)	Cl1B—C11B—C12B—C13B	179.63 (13)
C11A—C12A—C13A—C8A	0.0 (2)	C11B—C12B—C13B—C8B	−0.4 (3)
C9A—C8A—C13A—C12A	1.5 (2)	C9B—C8B—C13B—C12B	0.9 (2)
C2A—C8A—C13A—C12A	−177.39 (13)	C2B—C8B—C13B—C12B	179.99 (15)
C2A—C3A—C14A—O1A	5.1 (2)	C2B—C3B—C14B—O1B	20.61 (19)
C4A—C3A—C14A—O1A	−116.27 (16)	C4B—C3B—C14B—O1B	−97.02 (16)
C2A—C3A—C14A—C15A	−174.96 (12)	C2B—C3B—C14B—C15B	−162.94 (11)
C4A—C3A—C14A—C15A	63.68 (17)	C4B—C3B—C14B—C15B	79.43 (15)
O1A—C14A—C15A—C20A	−161.49 (17)	O1B—C14B—C15B—C20B	−151.52 (15)
C3A—C14A—C15A—C20A	18.6 (2)	C3B—C14B—C15B—C20B	32.04 (19)
O1A—C14A—C15A—C16A	19.8 (3)	O1B—C14B—C15B—C16B	27.3 (2)
C3A—C14A—C15A—C16A	−160.12 (17)	C3B—C14B—C15B—C16B	−149.11 (14)
C20A—C15A—C16A—C17A	−1.3 (3)	C20B—C15B—C16B—C17B	−0.5 (2)
C14A—C15A—C16A—C17A	177.4 (2)	C14B—C15B—C16B—C17B	−179.41 (15)
C15A—C16A—C17A—C18A	0.6 (4)	C15B—C16B—C17B—C18B	1.4 (3)
C16A—C17A—C18A—C19A	0.7 (5)	C16B—C17B—C18B—C19B	−1.0 (3)
C17A—C18A—C19A—C20A	−1.3 (4)	C17B—C18B—C19B—C20B	−0.4 (3)
C16A—C15A—C20A—C19A	0.7 (3)	C16B—C15B—C20B—C19B	−0.8 (2)
C14A—C15A—C20A—C19A	−177.94 (17)	C14B—C15B—C20B—C19B	178.01 (14)
C18A—C19A—C20A—C15A	0.6 (3)	C18B—C19B—C20B—C15B	1.3 (2)
N1A—C4A—C21A—O2A	−79.16 (18)	N1B—C4B—C21B—O2B	−43.9 (2)
C28A—C4A—C21A—O2A	170.40 (14)	C28B—C4B—C21B—O2B	−169.60 (14)
C3A—C4A—C21A—O2A	45.3 (2)	C3B—C4B—C21B—O2B	72.71 (18)
N1A—C4A—C21A—C22A	100.67 (12)	N1B—C4B—C21B—C22B	135.66 (12)
C28A—C4A—C21A—C22A	−9.77 (14)	C28B—C4B—C21B—C22B	9.96 (14)
C3A—C4A—C21A—C22A	−134.89 (12)	C3B—C4B—C21B—C22B	−107.73 (12)
O2A—C21A—C22A—C27A	−174.41 (15)	O2B—C21B—C22B—C27B	173.92 (15)
C4A—C21A—C22A—C27A	5.76 (16)	C4B—C21B—C22B—C27B	−5.63 (16)
O2A—C21A—C22A—C23A	4.9 (3)	O2B—C21B—C22B—C23B	−4.7 (3)
C4A—C21A—C22A—C23A	−174.94 (15)	C4B—C21B—C22B—C23B	175.70 (14)
C27A—C22A—C23A—C24A	−0.1 (2)	C27B—C22B—C23B—C24B	0.9 (2)
C21A—C22A—C23A—C24A	−179.38 (15)	C21B—C22B—C23B—C24B	179.44 (16)
C22A—C23A—C24A—C25A	0.5 (3)	C22B—C23B—C24B—C25B	0.6 (3)
C23A—C24A—C25A—C26A	0.0 (3)	C23B—C24B—C25B—C26B	−1.3 (3)
C24A—C25A—C26A—C27A	−0.7 (3)	C24B—C25B—C26B—C27B	0.5 (3)
C23A—C22A—C27A—C26A	−0.6 (2)	C23B—C22B—C27B—C26B	−1.7 (2)
C21A—C22A—C27A—C26A	178.74 (13)	C21B—C22B—C27B—C26B	179.47 (14)
C23A—C22A—C27A—C28A	−178.16 (14)	C23B—C22B—C27B—C28B	177.17 (13)
C21A—C22A—C27A—C28A	1.20 (16)	C21B—C22B—C27B—C28B	−1.63 (16)
C25A—C26A—C27A—C22A	1.0 (2)	C25B—C26B—C27B—C22B	1.0 (2)
C25A—C26A—C27A—C28A	178.06 (15)	C25B—C26B—C27B—C28B	−177.67 (16)
C22A—C27A—C28A—O3A	172.69 (14)	C22B—C27B—C28B—O3B	−171.97 (14)
C26A—C27A—C28A—O3A	−4.6 (2)	C26B—C27B—C28B—O3B	6.8 (3)
C22A—C27A—C28A—C4A	−7.68 (15)	C22B—C27B—C28B—C4B	8.28 (15)
C26A—C27A—C28A—C4A	175.01 (14)	C26B—C27B—C28B—C4B	−172.92 (15)
N1A—C4A—C28A—O3A	75.03 (16)	N1B—C4B—C28B—O3B	41.45 (19)
C21A—C4A—C28A—O3A	−169.84 (14)	C21B—C4B—C28B—O3B	169.35 (14)
C3A—C4A—C28A—O3A	−40.97 (18)	C3B—C4B—C28B—O3B	−72.80 (18)
N1A—C4A—C28A—C27A	−104.60 (12)	N1B—C4B—C28B—C27B	−138.79 (12)
C21A—C4A—C28A—C27A	10.53 (13)	C21B—C4B—C28B—C27B	−10.90 (14)
C3A—C4A—C28A—C27A	139.39 (11)	C3B—C4B—C28B—C27B	106.96 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5B—H5B1···O2B	0.97	2.57	3.199 (2)	123
C2A—H2A···O1A^i	0.98	2.60	3.490 (2)	152
C24A—H24A···O2B^ii	0.93	2.51	3.372 (2)	154
C12B—H12B···O3B^iii	0.93	2.48	3.285 (2)	144
C17B—H17B···O3B^iv	0.93	2.43	3.347 (2)	167

Symmetry codes: (i) −x, −y, −z+1; (ii) x−1, y−1, z; (iii) −x, −y, −z; (iv) x+1, y, z.