Crystal structure of 6-(4-chloro­phen­yl)-6a-nitro-6a,6b,8,9,10,12a-hexa­hydro-6H,7H-spiro[chromeno[3,4-a]indolizine-12,11′-indeno­[1,2-b]quinoxaline]

Syed Abuthahir, S.; NizamMohideen, M.; Viswanathan, V.; Velmurugan, D.; Nagasivarao, J.

doi:10.1107/S2056989019000975

Crystal structure of 6-(4-chlorophenyl)-6a-nitro-6a,6b,8,9,10,12a-hexahydro-6H,7H-spiro[chromeno[3,4-a]indolizine-12,11′-indeno[1,2-b]quinoxaline]

S. Syed Abuthahir, M. NizamMohideen, V. Viswanathan, D. Velmurugan and J. Nagasivarao

The title compound crystallized with two independent molecules (A and B) in the asymmetric unit. They differ essentially in the conformation of the pyrrolidine and cyclopentene rings; respectively, twisted and flat in molecule A, but envelope and twisted in molecule B.

Keywords: crystal structure; spiro compounds; cycloaddition; piperidine; pyran; pyrrolidine; cyclopentene; hydrogen bonding; C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019000975/su5475sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019000975/su5475Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019000975/su5475Isup3.cml Supplementary material

CCDC reference: 1024832

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.048
wR factor = 0.128
Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2B      --C21B     .        6.8 s.u.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        N2B Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of       C30B Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        N2A Check
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         32 Ang   3
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     10.556 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         13 Report

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT230_ALERT_2_G Hirshfeld Test Diff for    O3B      --N2B      .        8.3 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         7% Note
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  2  )         5% Note
PLAT432_ALERT_2_G Short Inter X...Y Contact  O3B'     ..C7A              2.91 Ang.
                                           1-x,-1/2+y,3/2-z  =      2_646 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4 Note
PLAT793_ALERT_4_G Model has Chirality at C12A        (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C12B        (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C13A        (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C13B        (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C20A        (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C20B        (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C21A        (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C21B        (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C22A        (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C22B        (Centro SPGR)          R Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2018 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  21 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 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
  12 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS2018 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

6-(4-Chlorophenyl)-6a-nitro-6a,6b,8,9,10,12a-hexahydro-6H,7H-spiro[chromeno[3,4-a]indolizine-12,11'-indeno[1,2-b]quinoxaline] top

Crystal data top

C₃₅H₂₇ClN₄O₃	F(000) = 2448
M_r = 587.05	D_x = 1.318 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.1880 (1) Å	Cell parameters from 14290 reflections
b = 23.4450 (3) Å	θ = 1.4–28.3°
c = 18.3710 (2) Å	µ = 0.17 mm⁻¹
β = 104.541 (2)°	T = 293 K
V = 5915.14 (12) Å³	Block, colourless
Z = 8	0.28 × 0.24 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	6368 reflections with I > 2σ(I)
ω and φ scans	R_int = 0.049
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θ_max = 25.5°, θ_min = 1.4°
T_min = 0.763, T_max = 0.841	h = −17→16
47802 measured reflections	k = −28→28
11007 independent reflections	l = −22→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0582P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.006
11007 reflections	Δρ_max = 0.35 e Å⁻³
824 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00059 (14)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1A	−0.00824 (5)	0.11344 (4)	0.58679 (6)	0.1082 (3)
O3A	0.4634 (4)	0.3265 (3)	0.6462 (7)	0.093 (3)	0.59 (2)
O4A	0.3489 (13)	0.2767 (4)	0.5822 (8)	0.156 (5)	0.59 (2)
O3A'	0.4590 (5)	0.2989 (9)	0.5979 (10)	0.109 (6)	0.41 (2)
O4A'	0.3204 (7)	0.2772 (5)	0.6066 (6)	0.071 (3)	0.41 (2)
O2A	0.45596 (11)	0.16374 (7)	0.58900 (9)	0.0664 (4)
N1A	0.50758 (12)	0.25630 (7)	0.81689 (10)	0.0495 (5)
N2A	0.4135 (2)	0.27834 (10)	0.63100 (16)	0.0724 (7)
N3A	0.73468 (12)	0.10164 (7)	0.88894 (11)	0.0546 (5)
N4A	0.53615 (12)	0.12159 (7)	0.80912 (10)	0.0479 (4)
C1A	0.60146 (14)	0.16158 (8)	0.82389 (12)	0.0441 (5)
C2A	0.69943 (14)	0.15201 (9)	0.86567 (13)	0.0491 (5)
C3A	0.66770 (15)	0.05800 (8)	0.87139 (12)	0.0473 (5)
C4A	0.56935 (15)	0.06792 (8)	0.83442 (12)	0.0464 (5)
C5A	0.50372 (16)	0.02191 (9)	0.82077 (14)	0.0580 (6)
H5A	0.438395	0.028115	0.797377	0.070*
C6A	0.84079 (17)	0.22040 (11)	0.92049 (17)	0.0791 (8)
H6A	0.883968	0.192052	0.943431	0.095*
C7A	0.8676 (2)	0.27716 (12)	0.92813 (19)	0.0902 (9)
H7A	0.929121	0.287229	0.956886	0.108*
C8A	0.8040 (2)	0.31873 (11)	0.89352 (17)	0.0792 (8)
H8A	0.822850	0.356768	0.899789	0.095*
C9A	0.71276 (18)	0.30543 (10)	0.84969 (16)	0.0698 (7)
H9A	0.670705	0.333954	0.825732	0.084*
C10A	0.68507 (15)	0.24874 (9)	0.84208 (14)	0.0541 (6)
C11A	0.74920 (15)	0.20657 (9)	0.87840 (14)	0.0556 (6)
C12A	0.58742 (14)	0.22441 (8)	0.79981 (13)	0.0475 (5)
C13A	0.56278 (15)	0.23380 (8)	0.71304 (13)	0.0501 (6)
H13A	0.581056	0.273216	0.705252	0.060*
C14A	0.61130 (16)	0.19680 (9)	0.66583 (14)	0.0555 (6)
C15A	0.71259 (17)	0.19720 (11)	0.67750 (16)	0.0753 (8)
H15A	0.750681	0.217889	0.717366	0.090*
C16A	0.7565 (2)	0.16720 (14)	0.6304 (2)	0.0964 (10)
H16A	0.823903	0.167393	0.638981	0.116*
C17A	0.7008 (3)	0.13700 (15)	0.5708 (2)	0.1035 (11)
H17A	0.730750	0.117208	0.538892	0.124*
C18A	0.6011 (2)	0.13591 (12)	0.55817 (16)	0.0837 (8)
H18A	0.563482	0.115436	0.517886	0.100*
C19A	0.55733 (18)	0.16564 (10)	0.60611 (14)	0.0623 (6)
C20A	0.41794 (15)	0.17284 (9)	0.65322 (12)	0.0528 (6)
H20A	0.449631	0.144457	0.690557	0.063*
C21A	0.45075 (15)	0.23143 (8)	0.68847 (12)	0.0484 (5)
C22A	0.41783 (15)	0.24203 (9)	0.76128 (13)	0.0488 (5)
H22A	0.394694	0.205552	0.776279	0.059*
C23A	0.34060 (17)	0.28633 (10)	0.76270 (15)	0.0691 (7)
H23A	0.279773	0.275799	0.727673	0.083*
H23B	0.360646	0.323168	0.747801	0.083*
C24A	0.32669 (19)	0.28976 (12)	0.84187 (17)	0.0853 (8)
H24A	0.282177	0.320671	0.844364	0.102*
H24B	0.297454	0.254555	0.853285	0.102*
C25A	0.42135 (19)	0.29947 (12)	0.90013 (16)	0.0799 (8)
H25A	0.409834	0.297599	0.949940	0.096*
H25B	0.445771	0.337265	0.893556	0.096*
C26A	0.49693 (18)	0.25542 (10)	0.89383 (14)	0.0655 (7)
H26A	0.558686	0.264254	0.928826	0.079*
H26B	0.476419	0.217866	0.905839	0.079*
C27A	0.31104 (16)	0.15833 (9)	0.63324 (13)	0.0540 (6)
C28A	0.24932 (17)	0.16813 (10)	0.56282 (14)	0.0660 (7)
H28A	0.273935	0.183682	0.524812	0.079*
C29A	0.15004 (18)	0.15474 (11)	0.54862 (15)	0.0733 (7)
H29A	0.108512	0.161832	0.501616	0.088*
C30A	0.11461 (17)	0.13090 (11)	0.60519 (17)	0.0694 (7)
C31A	0.17473 (19)	0.11935 (11)	0.67385 (16)	0.0712 (7)
H31A	0.150240	0.102750	0.711277	0.085*
C32A	0.27203 (18)	0.13245 (10)	0.68733 (14)	0.0639 (6)
H32A	0.313046	0.123757	0.734010	0.077*
C33A	0.53600 (19)	−0.03179 (10)	0.84187 (15)	0.0684 (7)
H33A	0.492516	−0.062175	0.831999	0.082*
C34A	0.6328 (2)	−0.04175 (10)	0.87785 (15)	0.0694 (7)
H34A	0.653630	−0.078651	0.891996	0.083*
C35A	0.69781 (18)	0.00240 (9)	0.89266 (14)	0.0611 (6)
H35A	0.762530	−0.004646	0.917074	0.073*
Cl2	−0.4783 (4)	−0.0038 (8)	0.6049 (3)	0.1272 (17)	0.72 (3)
Cl2'	−0.4841 (8)	−0.0219 (5)	0.6031 (6)	0.075 (3)	0.28 (3)
O2B	−0.00811 (9)	−0.04381 (5)	0.61628 (8)	0.0465 (4)
O3B	0.0158 (3)	−0.19290 (12)	0.7246 (4)	0.0803 (19)	0.686 (13)
O4B	−0.0989 (6)	−0.1554 (3)	0.6417 (4)	0.0762 (18)	0.686 (13)
O3B'	0.0164 (6)	−0.1739 (6)	0.6662 (11)	0.103 (7)	0.314 (13)
O4B'	−0.1267 (10)	−0.1518 (7)	0.6652 (10)	0.085 (4)	0.314 (13)
N1B	0.05316 (11)	−0.10204 (6)	0.86520 (9)	0.0425 (4)
N2B	−0.03373 (16)	−0.14979 (8)	0.69290 (14)	0.0569 (5)
N3B	0.26320 (15)	0.05649 (8)	0.92353 (11)	0.0627 (5)
N4B	0.07324 (13)	0.02914 (7)	0.83140 (10)	0.0499 (5)
C1B	0.14136 (15)	−0.00887 (8)	0.85633 (11)	0.0413 (5)
C2B	0.23529 (15)	0.00447 (9)	0.90188 (12)	0.0469 (5)
C3B	0.1926 (2)	0.09760 (9)	0.89932 (15)	0.0615 (7)
C4B	0.09943 (19)	0.08441 (9)	0.85415 (13)	0.0551 (6)
C5B	0.0311 (2)	0.12806 (10)	0.82974 (15)	0.0730 (8)
H5B	−0.030148	0.119622	0.799127	0.088*
C6B	0.38409 (16)	−0.05878 (12)	0.96269 (14)	0.0638 (7)
H6B	0.424242	−0.028847	0.984698	0.077*
C7B	0.41665 (17)	−0.11435 (13)	0.97233 (15)	0.0722 (7)
H7B	0.479521	−0.121910	1.000663	0.087*
C8B	0.35666 (18)	−0.15897 (11)	0.94023 (15)	0.0683 (7)
H8B	0.379491	−0.196242	0.947687	0.082*
C9B	0.26356 (16)	−0.14892 (9)	0.89737 (13)	0.0568 (6)
H9B	0.223331	−0.179045	0.876142	0.068*
C10B	0.23102 (14)	−0.09319 (8)	0.88649 (12)	0.0427 (5)
C11B	0.29053 (14)	−0.04826 (9)	0.91966 (12)	0.0468 (5)
C12B	0.13200 (13)	−0.07268 (7)	0.84181 (11)	0.0389 (5)
C13B	0.10657 (13)	−0.08981 (7)	0.75708 (11)	0.0376 (5)
H13B	0.129220	−0.129182	0.755638	0.045*
C14B	0.14984 (14)	−0.05683 (8)	0.70283 (12)	0.0400 (5)
C15B	0.25031 (15)	−0.05025 (9)	0.71576 (13)	0.0509 (5)
H15B	0.290440	−0.061195	0.761853	0.061*
C16B	0.29121 (16)	−0.02786 (10)	0.66161 (14)	0.0608 (6)
H16B	0.358347	−0.023378	0.671331	0.073*
C17B	0.23213 (16)	−0.01207 (10)	0.59272 (14)	0.0619 (6)
H17B	0.259923	0.002197	0.555686	0.074*
C18B	0.13295 (15)	−0.01723 (9)	0.57845 (13)	0.0530 (6)
H18B	0.093362	−0.006287	0.532149	0.064*
C19B	0.09235 (14)	−0.03897 (8)	0.63384 (12)	0.0414 (5)
C20B	−0.04584 (14)	−0.04205 (8)	0.68166 (11)	0.0417 (5)
H20B	−0.018549	−0.007621	0.709294	0.050*
C21B	−0.00534 (13)	−0.09262 (7)	0.73357 (11)	0.0388 (5)
C22B	−0.03703 (13)	−0.09156 (8)	0.80785 (12)	0.0427 (5)
H22B	−0.057926	−0.052574	0.815036	0.051*
C23B	−0.11678 (15)	−0.13179 (10)	0.81870 (14)	0.0601 (6)
H23C	−0.177409	−0.123216	0.782169	0.072*
H23D	−0.099102	−0.170920	0.811213	0.072*
C24B	−0.12967 (17)	−0.12448 (11)	0.89788 (15)	0.0712 (7)
H24C	−0.156099	−0.086913	0.902717	0.085*
H24D	−0.175717	−0.152580	0.906753	0.085*
C25B	−0.03347 (16)	−0.13142 (11)	0.95634 (14)	0.0666 (7)
H25C	−0.042950	−0.123592	1.005857	0.080*
H25D	−0.011283	−0.170526	0.955883	0.080*
C26B	0.04359 (16)	−0.09150 (9)	0.94120 (13)	0.0558 (6)
H26C	0.024780	−0.052179	0.946009	0.067*
H26D	0.105333	−0.098277	0.977321	0.067*
C27B	−0.15509 (14)	−0.03312 (9)	0.65835 (12)	0.0463 (5)
C28B	−0.21425 (15)	−0.05551 (9)	0.59349 (13)	0.0542 (6)
H28B	−0.186285	−0.075848	0.560808	0.065*
C29B	−0.31419 (16)	−0.04849 (11)	0.57578 (14)	0.0657 (7)
H29B	−0.353288	−0.064274	0.532108	0.079*
C30B	−0.35442 (16)	−0.01785 (12)	0.62382 (15)	0.0712 (8)
C31B	−0.29829 (18)	0.00675 (13)	0.68675 (16)	0.0824 (9)
H31B	−0.326700	0.028081	0.718270	0.099*
C32B	−0.19809 (17)	−0.00026 (10)	0.70355 (14)	0.0661 (7)
H32B	−0.159238	0.017412	0.745877	0.079*
C33B	0.0553 (3)	0.18321 (11)	0.8514 (2)	0.0940 (10)
H33B	0.010335	0.212283	0.835047	0.113*
C34B	0.1459 (3)	0.19590 (12)	0.8972 (2)	0.1033 (13)
H34B	0.160509	0.233535	0.911693	0.124*
C35B	0.2144 (2)	0.15477 (12)	0.92177 (18)	0.0885 (10)
H35B	0.274860	0.164220	0.952918	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1A	0.0558 (4)	0.1295 (7)	0.1340 (8)	−0.0009 (4)	0.0141 (5)	−0.0236 (6)
O3A	0.090 (3)	0.060 (3)	0.125 (7)	0.012 (2)	0.019 (3)	0.041 (3)
O4A	0.211 (12)	0.103 (4)	0.096 (7)	−0.009 (6)	−0.069 (7)	0.044 (5)
O3A'	0.071 (4)	0.138 (11)	0.119 (10)	0.007 (4)	0.026 (5)	0.083 (9)
O4A'	0.050 (4)	0.089 (4)	0.068 (6)	0.030 (3)	0.000 (3)	0.036 (4)
O2A	0.0599 (10)	0.0933 (12)	0.0451 (10)	0.0200 (9)	0.0114 (8)	−0.0011 (8)
N1A	0.0466 (10)	0.0523 (10)	0.0482 (12)	0.0092 (8)	0.0096 (10)	0.0035 (9)
N2A	0.0817 (18)	0.0717 (17)	0.0695 (19)	0.0311 (14)	0.0297 (17)	0.0288 (15)
N3A	0.0496 (11)	0.0496 (11)	0.0604 (13)	0.0099 (9)	0.0060 (10)	0.0068 (9)
N4A	0.0468 (10)	0.0476 (10)	0.0464 (12)	0.0015 (9)	0.0064 (9)	0.0083 (8)
C1A	0.0420 (12)	0.0467 (12)	0.0429 (13)	0.0046 (10)	0.0092 (10)	0.0060 (10)
C2A	0.0415 (12)	0.0505 (13)	0.0524 (15)	0.0045 (10)	0.0064 (11)	0.0051 (11)
C3A	0.0532 (13)	0.0447 (12)	0.0432 (14)	0.0050 (11)	0.0110 (11)	0.0024 (10)
C4A	0.0538 (13)	0.0448 (12)	0.0400 (13)	0.0053 (11)	0.0105 (11)	0.0045 (10)
C5A	0.0574 (14)	0.0490 (14)	0.0625 (17)	−0.0005 (11)	0.0053 (12)	0.0059 (11)
C6A	0.0535 (16)	0.0696 (17)	0.103 (2)	−0.0053 (13)	−0.0017 (16)	0.0133 (15)
C7A	0.0613 (17)	0.084 (2)	0.111 (3)	−0.0188 (16)	−0.0050 (17)	0.0029 (18)
C8A	0.0722 (18)	0.0607 (16)	0.101 (2)	−0.0163 (15)	0.0157 (18)	0.0041 (16)
C9A	0.0645 (16)	0.0510 (15)	0.092 (2)	−0.0031 (12)	0.0161 (15)	0.0096 (13)
C10A	0.0499 (13)	0.0484 (13)	0.0635 (17)	0.0002 (11)	0.0131 (12)	0.0048 (11)
C11A	0.0445 (13)	0.0564 (14)	0.0624 (17)	−0.0016 (11)	0.0071 (12)	0.0029 (12)
C12A	0.0450 (12)	0.0421 (12)	0.0540 (15)	0.0075 (10)	0.0096 (11)	0.0083 (10)
C13A	0.0513 (13)	0.0471 (12)	0.0532 (15)	0.0067 (10)	0.0157 (12)	0.0123 (10)
C14A	0.0541 (14)	0.0605 (14)	0.0557 (17)	0.0138 (11)	0.0207 (13)	0.0146 (12)
C15A	0.0587 (16)	0.0902 (18)	0.085 (2)	0.0135 (14)	0.0327 (16)	0.0109 (15)
C16A	0.0688 (19)	0.125 (3)	0.106 (3)	0.0219 (18)	0.041 (2)	−0.002 (2)
C17A	0.097 (3)	0.132 (3)	0.098 (3)	0.038 (2)	0.055 (2)	−0.003 (2)
C18A	0.083 (2)	0.107 (2)	0.067 (2)	0.0278 (16)	0.0297 (17)	−0.0042 (16)
C19A	0.0624 (16)	0.0752 (16)	0.0528 (17)	0.0194 (13)	0.0207 (14)	0.0121 (13)
C20A	0.0532 (13)	0.0664 (14)	0.0379 (14)	0.0171 (11)	0.0100 (11)	0.0078 (11)
C21A	0.0503 (13)	0.0488 (12)	0.0462 (14)	0.0164 (10)	0.0124 (11)	0.0151 (10)
C22A	0.0491 (13)	0.0487 (12)	0.0490 (15)	0.0058 (10)	0.0133 (12)	0.0044 (10)
C23A	0.0566 (15)	0.0798 (16)	0.0704 (19)	0.0256 (13)	0.0151 (14)	−0.0013 (14)
C24A	0.0693 (18)	0.111 (2)	0.081 (2)	0.0211 (16)	0.0309 (17)	−0.0120 (17)
C25A	0.0826 (19)	0.098 (2)	0.0613 (19)	0.0209 (16)	0.0223 (16)	−0.0129 (15)
C26A	0.0728 (16)	0.0730 (16)	0.0498 (16)	0.0088 (13)	0.0139 (14)	0.0032 (12)
C27A	0.0527 (13)	0.0606 (14)	0.0439 (15)	0.0150 (11)	0.0036 (12)	−0.0028 (11)
C28A	0.0611 (16)	0.0875 (18)	0.0461 (16)	0.0169 (13)	0.0073 (13)	0.0003 (13)
C29A	0.0555 (16)	0.102 (2)	0.0532 (17)	0.0227 (14)	−0.0031 (14)	−0.0085 (15)
C30A	0.0519 (15)	0.0826 (17)	0.071 (2)	0.0077 (13)	0.0111 (15)	−0.0173 (15)
C31A	0.0637 (17)	0.0844 (18)	0.064 (2)	−0.0125 (14)	0.0140 (15)	−0.0043 (14)
C32A	0.0682 (17)	0.0716 (16)	0.0462 (16)	−0.0012 (13)	0.0036 (13)	0.0050 (12)
C33A	0.0770 (18)	0.0504 (14)	0.075 (2)	−0.0092 (13)	0.0149 (15)	0.0022 (13)
C34A	0.0859 (19)	0.0449 (14)	0.077 (2)	0.0088 (14)	0.0191 (16)	0.0082 (13)
C35A	0.0670 (15)	0.0500 (14)	0.0633 (17)	0.0163 (12)	0.0104 (13)	0.0062 (12)
Cl2	0.0427 (12)	0.233 (6)	0.107 (2)	0.020 (2)	0.0209 (14)	0.054 (2)
Cl2'	0.034 (2)	0.125 (6)	0.069 (4)	−0.001 (2)	0.018 (2)	−0.016 (5)
O2B	0.0380 (8)	0.0614 (9)	0.0388 (9)	−0.0054 (6)	0.0073 (7)	0.0037 (7)
O3B	0.087 (2)	0.0405 (17)	0.096 (4)	0.0010 (14)	−0.010 (2)	−0.0061 (18)
O4B	0.090 (5)	0.061 (2)	0.056 (3)	−0.010 (3)	−0.023 (3)	−0.011 (2)
O3B'	0.065 (5)	0.095 (7)	0.158 (15)	−0.025 (4)	0.047 (6)	−0.080 (9)
O4B'	0.056 (6)	0.077 (5)	0.113 (11)	−0.023 (4)	0.005 (5)	−0.039 (6)
N1B	0.0381 (9)	0.0496 (10)	0.0382 (11)	−0.0030 (8)	0.0066 (8)	0.0028 (8)
N2B	0.0561 (13)	0.0554 (13)	0.0594 (16)	−0.0195 (11)	0.0150 (14)	−0.0131 (12)
N3B	0.0740 (13)	0.0585 (12)	0.0564 (14)	−0.0248 (11)	0.0179 (11)	−0.0137 (10)
N4B	0.0648 (12)	0.0390 (10)	0.0437 (11)	0.0004 (9)	0.0094 (9)	−0.0022 (8)
C1B	0.0486 (12)	0.0422 (12)	0.0322 (12)	−0.0035 (10)	0.0086 (10)	−0.0009 (9)
C2B	0.0516 (13)	0.0487 (13)	0.0407 (14)	−0.0128 (11)	0.0119 (11)	−0.0033 (10)
C3B	0.0920 (19)	0.0442 (13)	0.0571 (17)	−0.0184 (14)	0.0350 (15)	−0.0052 (12)
C4B	0.0858 (18)	0.0403 (13)	0.0433 (15)	−0.0034 (13)	0.0238 (14)	0.0010 (10)
C5B	0.109 (2)	0.0484 (15)	0.0691 (19)	0.0136 (14)	0.0356 (17)	0.0049 (13)
C6B	0.0423 (13)	0.0922 (19)	0.0542 (17)	−0.0118 (13)	0.0069 (12)	−0.0103 (14)
C7B	0.0450 (14)	0.111 (2)	0.0561 (18)	0.0170 (15)	0.0036 (13)	0.0054 (16)
C8B	0.0595 (16)	0.0815 (18)	0.0620 (18)	0.0246 (14)	0.0113 (14)	0.0097 (14)
C9B	0.0527 (14)	0.0566 (14)	0.0586 (16)	0.0065 (11)	0.0092 (13)	0.0033 (11)
C10B	0.0411 (11)	0.0487 (12)	0.0378 (13)	0.0019 (10)	0.0090 (10)	0.0036 (10)
C11B	0.0404 (12)	0.0609 (14)	0.0371 (13)	−0.0075 (11)	0.0060 (10)	−0.0014 (10)
C12B	0.0397 (11)	0.0380 (11)	0.0372 (13)	−0.0016 (9)	0.0062 (10)	0.0001 (9)
C13B	0.0385 (11)	0.0347 (10)	0.0381 (12)	−0.0007 (8)	0.0069 (10)	−0.0025 (9)
C14B	0.0400 (11)	0.0401 (11)	0.0406 (13)	−0.0030 (9)	0.0118 (10)	−0.0039 (9)
C15B	0.0413 (12)	0.0654 (14)	0.0447 (14)	−0.0050 (10)	0.0083 (11)	−0.0023 (11)
C16B	0.0409 (13)	0.0850 (17)	0.0582 (17)	−0.0112 (12)	0.0155 (13)	−0.0006 (13)
C17B	0.0555 (15)	0.0802 (16)	0.0545 (17)	−0.0104 (13)	0.0220 (13)	0.0077 (13)
C18B	0.0509 (13)	0.0595 (13)	0.0485 (15)	−0.0051 (11)	0.0123 (12)	0.0068 (11)
C19B	0.0384 (11)	0.0416 (11)	0.0444 (14)	−0.0027 (9)	0.0106 (11)	−0.0015 (9)
C20B	0.0398 (11)	0.0465 (12)	0.0368 (13)	−0.0049 (9)	0.0058 (10)	−0.0025 (9)
C21B	0.0391 (11)	0.0366 (10)	0.0383 (13)	−0.0083 (9)	0.0053 (10)	−0.0067 (9)
C22B	0.0399 (11)	0.0457 (11)	0.0417 (13)	−0.0029 (9)	0.0086 (10)	0.0009 (9)
C23B	0.0417 (12)	0.0777 (16)	0.0625 (17)	−0.0116 (11)	0.0160 (12)	0.0107 (13)
C24B	0.0505 (14)	0.0999 (19)	0.0679 (19)	0.0002 (13)	0.0235 (14)	0.0182 (15)
C25B	0.0590 (15)	0.0902 (18)	0.0534 (17)	−0.0021 (13)	0.0195 (13)	0.0159 (13)
C26B	0.0580 (14)	0.0680 (14)	0.0409 (14)	0.0015 (12)	0.0118 (12)	0.0039 (11)
C27B	0.0406 (12)	0.0606 (13)	0.0359 (13)	0.0009 (10)	0.0062 (11)	0.0054 (11)
C28B	0.0432 (13)	0.0741 (15)	0.0440 (15)	−0.0028 (11)	0.0083 (12)	−0.0002 (12)
C29B	0.0445 (13)	0.0996 (19)	0.0488 (16)	−0.0106 (13)	0.0039 (12)	0.0070 (14)
C30B	0.0362 (12)	0.128 (2)	0.0480 (17)	0.0101 (14)	0.0077 (13)	0.0243 (16)
C31B	0.0577 (16)	0.141 (3)	0.0496 (18)	0.0362 (16)	0.0158 (15)	0.0031 (17)
C32B	0.0585 (15)	0.0905 (17)	0.0443 (15)	0.0173 (13)	0.0036 (12)	−0.0043 (13)
C33B	0.151 (3)	0.0446 (17)	0.109 (3)	0.0099 (18)	0.074 (3)	0.0111 (16)
C34B	0.159 (3)	0.0409 (17)	0.140 (3)	−0.022 (2)	0.093 (3)	−0.0154 (19)
C35B	0.121 (2)	0.0559 (17)	0.103 (3)	−0.0356 (17)	0.055 (2)	−0.0220 (16)

Geometric parameters (Å, º) top

Cl1A—C30A	1.739 (2)	Cl2'—C30B	1.785 (11)
O3A—N2A	1.325 (8)	O2B—C19B	1.385 (2)
O4A—N2A	1.110 (9)	O2B—C20B	1.433 (2)
O3A'—N2A	1.102 (7)	O3B—N2B	1.284 (4)
O4A'—N2A	1.284 (12)	O4B—N2B	1.149 (6)
O2A—C19A	1.394 (3)	O3B'—N2B	1.115 (7)
O2A—C20A	1.431 (2)	O4B'—N2B	1.290 (15)
N1A—C12A	1.456 (2)	N1B—C26B	1.457 (3)
N1A—C22A	1.457 (3)	N1B—C22B	1.460 (2)
N1A—C26A	1.459 (3)	N1B—C12B	1.467 (2)
N2A—C21A	1.524 (3)	N2B—C21B	1.538 (3)
N3A—C2A	1.312 (2)	N3B—C2B	1.313 (2)
N3A—C3A	1.378 (3)	N3B—C3B	1.381 (3)
N4A—C1A	1.298 (2)	N4B—C1B	1.310 (2)
N4A—C4A	1.383 (2)	N4B—C4B	1.383 (3)
C1A—C2A	1.427 (3)	C1B—C2B	1.419 (3)
C1A—C12A	1.537 (3)	C1B—C12B	1.519 (3)
C2A—C11A	1.451 (3)	C2B—C11B	1.456 (3)
C3A—C35A	1.397 (3)	C3B—C4B	1.407 (3)
C3A—C4A	1.409 (3)	C3B—C35B	1.414 (3)
C4A—C5A	1.406 (3)	C4B—C5B	1.404 (3)
C5A—C33A	1.362 (3)	C5B—C33B	1.371 (4)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C11A	1.374 (3)	C6B—C7B	1.379 (3)
C6A—C7A	1.382 (3)	C6B—C11B	1.386 (3)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C8A	1.372 (4)	C7B—C8B	1.384 (3)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—C9A	1.377 (3)	C8B—C9B	1.378 (3)
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—C10A	1.383 (3)	C9B—C10B	1.383 (3)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.395 (3)	C10B—C11B	1.391 (3)
C10A—C12A	1.519 (3)	C10B—C12B	1.517 (3)
C12A—C13A	1.559 (3)	C12B—C13B	1.560 (3)
C13A—C14A	1.509 (3)	C13B—C14B	1.508 (3)
C13A—C21A	1.540 (3)	C13B—C21B	1.539 (2)
C13A—H13A	0.9800	C13B—H13B	0.9800
C14A—C19A	1.379 (3)	C14B—C19B	1.388 (3)
C14A—C15A	1.399 (3)	C14B—C15B	1.394 (3)
C15A—C16A	1.379 (4)	C15B—C16B	1.375 (3)
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—C17A	1.374 (4)	C16B—C17B	1.382 (3)
C16A—H16A	0.9300	C16B—H16B	0.9300
C17A—C18A	1.375 (4)	C17B—C18B	1.370 (3)
C17A—H17A	0.9300	C17B—H17B	0.9300
C18A—C19A	1.387 (3)	C18B—C19B	1.386 (3)
C18A—H18A	0.9300	C18B—H18B	0.9300
C20A—C27A	1.507 (3)	C20B—C27B	1.515 (3)
C20A—C21A	1.540 (3)	C20B—C21B	1.540 (3)
C20A—H20A	0.9800	C20B—H20B	0.9800
C21A—C22A	1.544 (3)	C21B—C22B	1.540 (3)
C22A—C23A	1.515 (3)	C22B—C23B	1.524 (3)
C22A—H22A	0.9800	C22B—H22B	0.9800
C23A—C24A	1.518 (4)	C23B—C24B	1.521 (3)
C23A—H23A	0.9700	C23B—H23C	0.9700
C23A—H23B	0.9700	C23B—H23D	0.9700
C24A—C25A	1.510 (4)	C24B—C25B	1.519 (3)
C24A—H24A	0.9700	C24B—H24C	0.9700
C24A—H24B	0.9700	C24B—H24D	0.9700
C25A—C26A	1.514 (3)	C25B—C26B	1.517 (3)
C25A—H25A	0.9700	C25B—H25C	0.9700
C25A—H25B	0.9700	C25B—H25D	0.9700
C26A—H26A	0.9700	C26B—H26C	0.9700
C26A—H26B	0.9700	C26B—H26D	0.9700
C27A—C28A	1.387 (3)	C27B—C28B	1.378 (3)
C27A—C32A	1.392 (3)	C27B—C32B	1.382 (3)
C28A—C29A	1.402 (3)	C28B—C29B	1.383 (3)
C28A—H28A	0.9300	C28B—H28B	0.9300
C29A—C30A	1.381 (4)	C29B—C30B	1.369 (3)
C29A—H29A	0.9300	C29B—H29B	0.9300
C30A—C31A	1.361 (4)	C30B—C31B	1.357 (4)
C31A—C32A	1.375 (3)	C31B—C32B	1.387 (3)
C31A—H31A	0.9300	C31B—H31B	0.9300
C32A—H32A	0.9300	C32B—H32B	0.9300
C33A—C34A	1.386 (3)	C33B—C34B	1.380 (5)
C33A—H33A	0.9300	C33B—H33B	0.9300
C34A—C35A	1.368 (3)	C34B—C35B	1.364 (4)
C34A—H34A	0.9300	C34B—H34B	0.9300
C35A—H35A	0.9300	C35B—H35B	0.9300
Cl2—C30B	1.735 (5)

C19A—O2A—C20A	112.99 (17)	C26B—N1B—C22B	112.79 (15)
C12A—N1A—C22A	108.73 (16)	C26B—N1B—C12B	117.55 (16)
C12A—N1A—C26A	118.50 (18)	C22B—N1B—C12B	107.72 (15)
C22A—N1A—C26A	113.02 (17)	O4B—N2B—O3B	121.1 (4)
O3A'—N2A—O4A'	120.6 (6)	O3B'—N2B—O4B'	120.7 (7)
O4A—N2A—O3A	119.3 (6)	O3B'—N2B—C21B	122.5 (4)
O3A'—N2A—C21A	123.2 (5)	O4B—N2B—C21B	123.8 (4)
O4A—N2A—C21A	127.4 (6)	O3B—N2B—C21B	114.7 (2)
O4A'—N2A—C21A	112.0 (5)	O4B'—N2B—C21B	109.9 (7)
O3A—N2A—C21A	113.2 (4)	C2B—N3B—C3B	114.3 (2)
C2A—N3A—C3A	114.08 (18)	C1B—N4B—C4B	114.39 (19)
C1A—N4A—C4A	114.97 (17)	N4B—C1B—C2B	123.88 (18)
N4A—C1A—C2A	123.15 (18)	N4B—C1B—C12B	125.74 (18)
N4A—C1A—C12A	126.74 (18)	C2B—C1B—C12B	110.38 (17)
C2A—C1A—C12A	110.11 (17)	N3B—C2B—C1B	123.4 (2)
N3A—C2A—C1A	123.86 (19)	N3B—C2B—C11B	128.0 (2)
N3A—C2A—C11A	127.6 (2)	C1B—C2B—C11B	108.55 (17)
C1A—C2A—C11A	108.48 (18)	N3B—C3B—C4B	122.31 (19)
N3A—C3A—C35A	118.9 (2)	N3B—C3B—C35B	118.7 (3)
N3A—C3A—C4A	122.10 (18)	C4B—C3B—C35B	119.0 (3)
C35A—C3A—C4A	119.0 (2)	N4B—C4B—C5B	118.3 (2)
N4A—C4A—C5A	118.9 (2)	N4B—C4B—C3B	121.7 (2)
N4A—C4A—C3A	121.64 (18)	C5B—C4B—C3B	120.0 (2)
C5A—C4A—C3A	119.38 (19)	C33B—C5B—C4B	119.5 (3)
C33A—C5A—C4A	119.9 (2)	C33B—C5B—H5B	120.2
C33A—C5A—H5A	120.1	C4B—C5B—H5B	120.2
C4A—C5A—H5A	120.1	C7B—C6B—C11B	118.9 (2)
C11A—C6A—C7A	118.8 (2)	C7B—C6B—H6B	120.5
C11A—C6A—H6A	120.6	C11B—C6B—H6B	120.5
C7A—C6A—H6A	120.6	C6B—C7B—C8B	120.6 (2)
C8A—C7A—C6A	120.3 (3)	C6B—C7B—H7B	119.7
C8A—C7A—H7A	119.8	C8B—C7B—H7B	119.7
C6A—C7A—H7A	119.8	C9B—C8B—C7B	120.9 (2)
C7A—C8A—C9A	121.5 (2)	C9B—C8B—H8B	119.6
C7A—C8A—H8A	119.2	C7B—C8B—H8B	119.6
C9A—C8A—H8A	119.2	C8B—C9B—C10B	118.8 (2)
C8A—C9A—C10A	118.5 (2)	C8B—C9B—H9B	120.6
C8A—C9A—H9A	120.7	C10B—C9B—H9B	120.6
C10A—C9A—H9A	120.7	C9B—C10B—C11B	120.5 (2)
C9A—C10A—C11A	119.9 (2)	C9B—C10B—C12B	127.44 (19)
C9A—C10A—C12A	127.7 (2)	C11B—C10B—C12B	112.01 (17)
C11A—C10A—C12A	112.34 (18)	C6B—C11B—C10B	120.3 (2)
C6A—C11A—C10A	120.9 (2)	C6B—C11B—C2B	131.6 (2)
C6A—C11A—C2A	130.7 (2)	C10B—C11B—C2B	108.13 (18)
C10A—C11A—C2A	108.37 (19)	N1B—C12B—C10B	111.32 (15)
N1A—C12A—C10A	110.86 (17)	N1B—C12B—C1B	116.76 (15)
N1A—C12A—C1A	118.80 (16)	C10B—C12B—C1B	100.89 (15)
C10A—C12A—C1A	100.20 (16)	N1B—C12B—C13B	99.74 (14)
N1A—C12A—C13A	99.27 (16)	C10B—C12B—C13B	114.16 (15)
C10A—C12A—C13A	114.28 (17)	C1B—C12B—C13B	114.64 (15)
C1A—C12A—C13A	114.15 (17)	C14B—C13B—C21B	113.52 (16)
C14A—C13A—C21A	113.38 (19)	C14B—C13B—C12B	119.80 (15)
C14A—C13A—C12A	119.26 (17)	C21B—C13B—C12B	104.77 (14)
C21A—C13A—C12A	104.14 (16)	C14B—C13B—H13B	105.9
C14A—C13A—H13A	106.4	C21B—C13B—H13B	105.9
C21A—C13A—H13A	106.4	C12B—C13B—H13B	105.9
C12A—C13A—H13A	106.4	C19B—C14B—C15B	117.62 (18)
C19A—C14A—C15A	118.0 (2)	C19B—C14B—C13B	120.96 (17)
C19A—C14A—C13A	121.3 (2)	C15B—C14B—C13B	120.84 (18)
C15A—C14A—C13A	120.5 (2)	C16B—C15B—C14B	121.2 (2)
C16A—C15A—C14A	120.6 (3)	C16B—C15B—H15B	119.4
C16A—C15A—H15A	119.7	C14B—C15B—H15B	119.4
C14A—C15A—H15A	119.7	C15B—C16B—C17B	119.7 (2)
C17A—C16A—C15A	120.2 (3)	C15B—C16B—H16B	120.1
C17A—C16A—H16A	119.9	C17B—C16B—H16B	120.1
C15A—C16A—H16A	119.9	C18B—C17B—C16B	120.6 (2)
C18A—C17A—C16A	120.3 (3)	C18B—C17B—H17B	119.7
C18A—C17A—H17A	119.8	C16B—C17B—H17B	119.7
C16A—C17A—H17A	119.8	C17B—C18B—C19B	119.2 (2)
C17A—C18A—C19A	119.3 (3)	C17B—C18B—H18B	120.4
C17A—C18A—H18A	120.3	C19B—C18B—H18B	120.4
C19A—C18A—H18A	120.3	O2B—C19B—C18B	116.89 (19)
C14A—C19A—C18A	121.6 (2)	O2B—C19B—C14B	121.49 (17)
C14A—C19A—O2A	122.1 (2)	C18B—C19B—C14B	121.59 (18)
C18A—C19A—O2A	116.3 (2)	O2B—C20B—C27B	109.76 (16)
O2A—C20A—C27A	109.28 (18)	O2B—C20B—C21B	109.69 (14)
O2A—C20A—C21A	110.05 (17)	C27B—C20B—C21B	118.53 (15)
C27A—C20A—C21A	118.89 (17)	O2B—C20B—H20B	106.0
O2A—C20A—H20A	105.9	C27B—C20B—H20B	106.0
C27A—C20A—H20A	105.9	C21B—C20B—H20B	106.0
C21A—C20A—H20A	105.9	N2B—C21B—C13B	107.44 (15)
N2A—C21A—C20A	109.7 (2)	N2B—C21B—C20B	111.02 (17)
N2A—C21A—C13A	109.26 (19)	C13B—C21B—C20B	109.83 (14)
C20A—C21A—C13A	109.64 (16)	N2B—C21B—C22B	110.21 (15)
N2A—C21A—C22A	110.86 (17)	C13B—C21B—C22B	105.12 (16)
C20A—C21A—C22A	112.50 (16)	C20B—C21B—C22B	112.93 (15)
C13A—C21A—C22A	104.76 (18)	N1B—C22B—C23B	110.28 (17)
N1A—C22A—C23A	109.82 (18)	N1B—C22B—C21B	103.81 (14)
N1A—C22A—C21A	104.07 (16)	C23B—C22B—C21B	119.82 (17)
C23A—C22A—C21A	120.19 (18)	N1B—C22B—H22B	107.4
N1A—C22A—H22A	107.4	C23B—C22B—H22B	107.4
C23A—C22A—H22A	107.4	C21B—C22B—H22B	107.4
C21A—C22A—H22A	107.4	C24B—C23B—C22B	109.08 (19)
C22A—C23A—C24A	108.7 (2)	C24B—C23B—H23C	109.9
C22A—C23A—H23A	109.9	C22B—C23B—H23C	109.9
C24A—C23A—H23A	109.9	C24B—C23B—H23D	109.9
C22A—C23A—H23B	109.9	C22B—C23B—H23D	109.9
C24A—C23A—H23B	109.9	H23C—C23B—H23D	108.3
H23A—C23A—H23B	108.3	C25B—C24B—C23B	111.20 (18)
C25A—C24A—C23A	112.4 (2)	C25B—C24B—H24C	109.4
C25A—C24A—H24A	109.1	C23B—C24B—H24C	109.4
C23A—C24A—H24A	109.1	C25B—C24B—H24D	109.4
C25A—C24A—H24B	109.1	C23B—C24B—H24D	109.4
C23A—C24A—H24B	109.1	H24C—C24B—H24D	108.0
H24A—C24A—H24B	107.9	C26B—C25B—C24B	111.43 (19)
C24A—C25A—C26A	111.3 (2)	C26B—C25B—H25C	109.3
C24A—C25A—H25A	109.4	C24B—C25B—H25C	109.3
C26A—C25A—H25A	109.4	C26B—C25B—H25D	109.3
C24A—C25A—H25B	109.4	C24B—C25B—H25D	109.3
C26A—C25A—H25B	109.4	H25C—C25B—H25D	108.0
H25A—C25A—H25B	108.0	N1B—C26B—C25B	108.41 (18)
N1A—C26A—C25A	108.2 (2)	N1B—C26B—H26C	110.0
N1A—C26A—H26A	110.1	C25B—C26B—H26C	110.0
C25A—C26A—H26A	110.1	N1B—C26B—H26D	110.0
N1A—C26A—H26B	110.1	C25B—C26B—H26D	110.0
C25A—C26A—H26B	110.1	H26C—C26B—H26D	108.4
H26A—C26A—H26B	108.4	C28B—C27B—C32B	117.8 (2)
C28A—C27A—C32A	117.8 (2)	C28B—C27B—C20B	123.35 (18)
C28A—C27A—C20A	123.4 (2)	C32B—C27B—C20B	118.8 (2)
C32A—C27A—C20A	118.7 (2)	C27B—C28B—C29B	121.6 (2)
C27A—C28A—C29A	120.4 (2)	C27B—C28B—H28B	119.2
C27A—C28A—H28A	119.8	C29B—C28B—H28B	119.2
C29A—C28A—H28A	119.8	C30B—C29B—C28B	118.7 (2)
C30A—C29A—C28A	119.3 (2)	C30B—C29B—H29B	120.7
C30A—C29A—H29A	120.4	C28B—C29B—H29B	120.7
C28A—C29A—H29A	120.4	C31B—C30B—C29B	121.5 (2)
C31A—C30A—C29A	121.1 (2)	C31B—C30B—Cl2	116.0 (5)
C31A—C30A—Cl1A	119.8 (2)	C29B—C30B—Cl2	122.4 (4)
C29A—C30A—Cl1A	119.0 (2)	C31B—C30B—Cl2'	123.9 (3)
C30A—C31A—C32A	119.3 (2)	C29B—C30B—Cl2'	114.1 (3)
C30A—C31A—H31A	120.3	C30B—C31B—C32B	119.3 (2)
C32A—C31A—H31A	120.3	C30B—C31B—H31B	120.4
C31A—C32A—C27A	122.0 (2)	C32B—C31B—H31B	120.4
C31A—C32A—H32A	119.0	C27B—C32B—C31B	121.0 (2)
C27A—C32A—H32A	119.0	C27B—C32B—H32B	119.5
C5A—C33A—C34A	120.9 (2)	C31B—C32B—H32B	119.5
C5A—C33A—H33A	119.6	C5B—C33B—C34B	120.5 (3)
C34A—C33A—H33A	119.6	C5B—C33B—H33B	119.8
C35A—C34A—C33A	120.4 (2)	C34B—C33B—H33B	119.8
C35A—C34A—H34A	119.8	C35B—C34B—C33B	121.8 (3)
C33A—C34A—H34A	119.8	C35B—C34B—H34B	119.1
C34A—C35A—C3A	120.5 (2)	C33B—C34B—H34B	119.1
C34A—C35A—H35A	119.8	C34B—C35B—C3B	119.2 (3)
C3A—C35A—H35A	119.8	C34B—C35B—H35B	120.4
C19B—O2B—C20B	112.44 (15)	C3B—C35B—H35B	120.4

C4A—N4A—C1A—C2A	−2.5 (3)	C4B—N4B—C1B—C12B	178.48 (17)
C4A—N4A—C1A—C12A	176.95 (19)	C3B—N3B—C2B—C1B	1.1 (3)
C3A—N3A—C2A—C1A	−1.8 (3)	C3B—N3B—C2B—C11B	−177.9 (2)
C3A—N3A—C2A—C11A	176.6 (2)	N4B—C1B—C2B—N3B	0.0 (3)
N4A—C1A—C2A—N3A	4.6 (3)	C12B—C1B—C2B—N3B	−179.61 (18)
C12A—C1A—C2A—N3A	−174.9 (2)	N4B—C1B—C2B—C11B	179.10 (18)
N4A—C1A—C2A—C11A	−174.02 (19)	C12B—C1B—C2B—C11B	−0.5 (2)
C12A—C1A—C2A—C11A	6.5 (2)	C2B—N3B—C3B—C4B	−1.1 (3)
C2A—N3A—C3A—C35A	179.2 (2)	C2B—N3B—C3B—C35B	177.9 (2)
C2A—N3A—C3A—C4A	−2.5 (3)	C1B—N4B—C4B—C5B	179.66 (19)
C1A—N4A—C4A—C5A	−179.82 (19)	C1B—N4B—C4B—C3B	1.0 (3)
C1A—N4A—C4A—C3A	−1.8 (3)	N3B—C3B—C4B—N4B	0.1 (3)
N3A—C3A—C4A—N4A	4.5 (3)	C35B—C3B—C4B—N4B	−179.0 (2)
C35A—C3A—C4A—N4A	−177.15 (19)	N3B—C3B—C4B—C5B	−178.6 (2)
N3A—C3A—C4A—C5A	−177.5 (2)	C35B—C3B—C4B—C5B	2.4 (3)
C35A—C3A—C4A—C5A	0.9 (3)	N4B—C4B—C5B—C33B	−179.9 (2)
N4A—C4A—C5A—C33A	176.7 (2)	C3B—C4B—C5B—C33B	−1.2 (3)
C3A—C4A—C5A—C33A	−1.4 (3)	C11B—C6B—C7B—C8B	−0.6 (4)
C11A—C6A—C7A—C8A	−0.7 (5)	C6B—C7B—C8B—C9B	0.7 (4)
C6A—C7A—C8A—C9A	−0.9 (5)	C7B—C8B—C9B—C10B	0.4 (3)
C7A—C8A—C9A—C10A	1.2 (4)	C8B—C9B—C10B—C11B	−1.4 (3)
C8A—C9A—C10A—C11A	−0.1 (4)	C8B—C9B—C10B—C12B	−179.9 (2)
C8A—C9A—C10A—C12A	177.1 (2)	C7B—C6B—C11B—C10B	−0.4 (3)
C7A—C6A—C11A—C10A	1.8 (4)	C7B—C6B—C11B—C2B	177.4 (2)
C7A—C6A—C11A—C2A	−174.7 (3)	C9B—C10B—C11B—C6B	1.4 (3)
C9A—C10A—C11A—C6A	−1.5 (4)	C12B—C10B—C11B—C6B	−179.87 (19)
C12A—C10A—C11A—C6A	−179.1 (2)	C9B—C10B—C11B—C2B	−176.84 (18)
C9A—C10A—C11A—C2A	175.7 (2)	C12B—C10B—C11B—C2B	1.8 (2)
C12A—C10A—C11A—C2A	−1.9 (3)	N3B—C2B—C11B—C6B	0.2 (4)
N3A—C2A—C11A—C6A	−4.6 (4)	C1B—C2B—C11B—C6B	−178.9 (2)
C1A—C2A—C11A—C6A	173.9 (3)	N3B—C2B—C11B—C10B	178.2 (2)
N3A—C2A—C11A—C10A	178.6 (2)	C1B—C2B—C11B—C10B	−0.8 (2)
C1A—C2A—C11A—C10A	−2.9 (3)	C26B—N1B—C12B—C10B	66.0 (2)
C22A—N1A—C12A—C10A	164.91 (17)	C22B—N1B—C12B—C10B	−165.34 (15)
C26A—N1A—C12A—C10A	−64.2 (2)	C26B—N1B—C12B—C1B	−49.1 (2)
C22A—N1A—C12A—C1A	−79.9 (2)	C22B—N1B—C12B—C1B	79.6 (2)
C26A—N1A—C12A—C1A	51.0 (3)	C26B—N1B—C12B—C13B	−173.19 (16)
C22A—N1A—C12A—C13A	44.37 (19)	C22B—N1B—C12B—C13B	−44.49 (17)
C26A—N1A—C12A—C13A	175.23 (18)	C9B—C10B—C12B—N1B	52.0 (3)
C9A—C10A—C12A—N1A	−45.7 (3)	C11B—C10B—C12B—N1B	−126.56 (17)
C11A—C10A—C12A—N1A	131.70 (19)	C9B—C10B—C12B—C1B	176.56 (19)
C9A—C10A—C12A—C1A	−172.0 (2)	C11B—C10B—C12B—C1B	−2.0 (2)
C11A—C10A—C12A—C1A	5.4 (2)	C9B—C10B—C12B—C13B	−60.0 (3)
C9A—C10A—C12A—C13A	65.5 (3)	C11B—C10B—C12B—C13B	121.47 (18)
C11A—C10A—C12A—C13A	−117.1 (2)	N4B—C1B—C12B—N1B	−57.3 (3)
N4A—C1A—C12A—N1A	52.7 (3)	C2B—C1B—C12B—N1B	122.22 (18)
C2A—C1A—C12A—N1A	−127.8 (2)	N4B—C1B—C12B—C10B	−178.12 (18)
N4A—C1A—C12A—C10A	173.5 (2)	C2B—C1B—C12B—C10B	1.4 (2)
C2A—C1A—C12A—C10A	−7.0 (2)	N4B—C1B—C12B—C13B	58.7 (2)
N4A—C1A—C12A—C13A	−63.9 (3)	C2B—C1B—C12B—C13B	−121.69 (18)
C2A—C1A—C12A—C13A	115.5 (2)	N1B—C12B—C13B—C14B	162.78 (16)
N1A—C12A—C13A—C14A	−165.11 (18)	C10B—C12B—C13B—C14B	−78.4 (2)
C10A—C12A—C13A—C14A	76.9 (2)	C1B—C12B—C13B—C14B	37.2 (2)
C1A—C12A—C13A—C14A	−37.7 (3)	N1B—C12B—C13B—C21B	33.99 (17)
N1A—C12A—C13A—C21A	−37.50 (18)	C10B—C12B—C13B—C21B	152.76 (15)
C10A—C12A—C13A—C21A	−155.51 (16)	C1B—C12B—C13B—C21B	−91.55 (17)
C1A—C12A—C13A—C21A	89.96 (19)	C21B—C13B—C14B—C19B	−8.9 (2)
C21A—C13A—C14A—C19A	1.3 (3)	C12B—C13B—C14B—C19B	−133.61 (18)
C12A—C13A—C14A—C19A	124.5 (2)	C21B—C13B—C14B—C15B	−179.94 (17)
C21A—C13A—C14A—C15A	175.57 (19)	C12B—C13B—C14B—C15B	55.3 (2)
C12A—C13A—C14A—C15A	−61.2 (3)	C19B—C14B—C15B—C16B	−1.2 (3)
C19A—C14A—C15A—C16A	0.0 (4)	C13B—C14B—C15B—C16B	170.14 (19)
C13A—C14A—C15A—C16A	−174.5 (2)	C14B—C15B—C16B—C17B	−0.7 (3)
C14A—C15A—C16A—C17A	0.7 (5)	C15B—C16B—C17B—C18B	1.6 (4)
C15A—C16A—C17A—C18A	−0.8 (5)	C16B—C17B—C18B—C19B	−0.5 (3)
C16A—C17A—C18A—C19A	0.1 (5)	C20B—O2B—C19B—C18B	−154.42 (17)
C15A—C14A—C19A—C18A	−0.7 (4)	C20B—O2B—C19B—C14B	27.7 (2)
C13A—C14A—C19A—C18A	173.8 (2)	C17B—C18B—C19B—O2B	−179.39 (18)
C15A—C14A—C19A—O2A	−178.5 (2)	C17B—C18B—C19B—C14B	−1.5 (3)
C13A—C14A—C19A—O2A	−4.1 (3)	C15B—C14B—C19B—O2B	−179.88 (17)
C17A—C18A—C19A—C14A	0.6 (4)	C13B—C14B—C19B—O2B	8.8 (3)
C17A—C18A—C19A—O2A	178.6 (2)	C15B—C14B—C19B—C18B	2.3 (3)
C20A—O2A—C19A—C14A	−27.2 (3)	C13B—C14B—C19B—C18B	−169.04 (18)
C20A—O2A—C19A—C18A	154.9 (2)	C19B—O2B—C20B—C27B	166.38 (15)
C19A—O2A—C20A—C27A	−168.56 (18)	C19B—O2B—C20B—C21B	−61.74 (19)
C19A—O2A—C20A—C21A	59.2 (2)	O3B'—N2B—C21B—C13B	−22.4 (14)
O3A'—N2A—C21A—C20A	−99.6 (17)	O4B—N2B—C21B—C13B	−142.6 (5)
O4A—N2A—C21A—C20A	25.4 (15)	O3B—N2B—C21B—C13B	43.6 (4)
O4A'—N2A—C21A—C20A	57.6 (6)	O4B'—N2B—C21B—C13B	−173.4 (9)
O3A—N2A—C21A—C20A	−158.5 (6)	O3B'—N2B—C21B—C20B	97.7 (14)
O3A'—N2A—C21A—C13A	20.6 (17)	O4B—N2B—C21B—C20B	−22.4 (6)
O4A—N2A—C21A—C13A	145.6 (15)	O3B—N2B—C21B—C20B	163.7 (4)
O4A'—N2A—C21A—C13A	177.8 (6)	O4B'—N2B—C21B—C20B	−53.3 (9)
O3A—N2A—C21A—C13A	−38.3 (6)	O3B'—N2B—C21B—C22B	−136.4 (14)
O3A'—N2A—C21A—C22A	135.6 (17)	O4B—N2B—C21B—C22B	103.4 (6)
O4A—N2A—C21A—C22A	−99.4 (15)	O3B—N2B—C21B—C22B	−70.4 (4)
O4A'—N2A—C21A—C22A	−67.2 (6)	O4B'—N2B—C21B—C22B	72.5 (9)
O3A—N2A—C21A—C22A	76.7 (6)	C14B—C13B—C21B—N2B	96.99 (19)
O2A—C20A—C21A—N2A	60.0 (2)	C12B—C13B—C21B—N2B	−130.54 (16)
C27A—C20A—C21A—N2A	−67.0 (2)	C14B—C13B—C21B—C20B	−23.9 (2)
O2A—C20A—C21A—C13A	−59.9 (2)	C12B—C13B—C21B—C20B	108.61 (16)
C27A—C20A—C21A—C13A	172.98 (18)	C14B—C13B—C21B—C22B	−145.63 (15)
O2A—C20A—C21A—C22A	−176.09 (16)	C12B—C13B—C21B—C22B	−13.16 (18)
C27A—C20A—C21A—C22A	56.8 (3)	O2B—C20B—C21B—N2B	−59.52 (19)
C14A—C13A—C21A—N2A	−91.0 (2)	C27B—C20B—C21B—N2B	67.6 (2)
C12A—C13A—C21A—N2A	137.88 (18)	O2B—C20B—C21B—C13B	59.2 (2)
C14A—C13A—C21A—C20A	29.2 (2)	C27B—C20B—C21B—C13B	−173.75 (16)
C12A—C13A—C21A—C20A	−101.90 (18)	O2B—C20B—C21B—C22B	176.12 (14)
C14A—C13A—C21A—C22A	150.20 (17)	C27B—C20B—C21B—C22B	−56.8 (2)
C12A—C13A—C21A—C22A	19.04 (19)	C26B—N1B—C22B—C23B	−62.0 (2)
C12A—N1A—C22A—C23A	−163.08 (17)	C12B—N1B—C22B—C23B	166.59 (16)
C26A—N1A—C22A—C23A	63.2 (2)	C26B—N1B—C22B—C21B	168.41 (15)
C12A—N1A—C22A—C21A	−33.18 (19)	C12B—N1B—C22B—C21B	37.05 (18)
C26A—N1A—C22A—C21A	−166.94 (16)	N2B—C21B—C22B—N1B	102.47 (18)
N2A—C21A—C22A—N1A	−110.9 (2)	C13B—C21B—C22B—N1B	−13.01 (18)
C20A—C21A—C22A—N1A	125.88 (17)	C20B—C21B—C22B—N1B	−132.74 (16)
C13A—C21A—C22A—N1A	6.84 (19)	N2B—C21B—C22B—C23B	−21.0 (3)
N2A—C21A—C22A—C23A	12.5 (3)	C13B—C21B—C22B—C23B	−136.53 (18)
C20A—C21A—C22A—C23A	−110.7 (2)	C20B—C21B—C22B—C23B	103.8 (2)
C13A—C21A—C22A—C23A	130.2 (2)	N1B—C22B—C23B—C24B	56.4 (2)
N1A—C22A—C23A—C24A	−56.5 (3)	C21B—C22B—C23B—C24B	176.73 (18)
C21A—C22A—C23A—C24A	−177.1 (2)	C22B—C23B—C24B—C25B	−53.5 (3)
C22A—C23A—C24A—C25A	53.1 (3)	C23B—C24B—C25B—C26B	54.6 (3)
C23A—C24A—C25A—C26A	−53.5 (3)	C22B—N1B—C26B—C25B	60.7 (2)
C12A—N1A—C26A—C25A	170.03 (19)	C12B—N1B—C26B—C25B	−173.01 (17)
C22A—N1A—C26A—C25A	−61.1 (2)	C24B—C25B—C26B—N1B	−56.2 (3)
C24A—C25A—C26A—N1A	54.9 (3)	O2B—C20B—C27B—C28B	34.6 (3)
O2A—C20A—C27A—C28A	−35.0 (3)	C21B—C20B—C27B—C28B	−92.5 (2)
C21A—C20A—C27A—C28A	92.5 (3)	O2B—C20B—C27B—C32B	−144.46 (19)
O2A—C20A—C27A—C32A	143.4 (2)	C21B—C20B—C27B—C32B	88.5 (2)
C21A—C20A—C27A—C32A	−89.2 (3)	C32B—C27B—C28B—C29B	−3.8 (3)
C32A—C27A—C28A—C29A	3.1 (3)	C20B—C27B—C28B—C29B	177.15 (19)
C20A—C27A—C28A—C29A	−178.6 (2)	C27B—C28B—C29B—C30B	0.8 (3)
C27A—C28A—C29A—C30A	−0.9 (4)	C28B—C29B—C30B—C31B	1.8 (4)
C28A—C29A—C30A—C31A	−1.2 (4)	C28B—C29B—C30B—Cl2	177.0 (6)
C28A—C29A—C30A—Cl1A	−179.08 (18)	C28B—C29B—C30B—Cl2'	−170.1 (5)
C29A—C30A—C31A—C32A	1.0 (4)	C29B—C30B—C31B—C32B	−1.3 (4)
Cl1A—C30A—C31A—C32A	178.90 (18)	Cl2—C30B—C31B—C32B	−176.9 (6)
C30A—C31A—C32A—C27A	1.3 (4)	Cl2'—C30B—C31B—C32B	169.7 (6)
C28A—C27A—C32A—C31A	−3.3 (3)	C28B—C27B—C32B—C31B	4.2 (3)
C20A—C27A—C32A—C31A	178.3 (2)	C20B—C27B—C32B—C31B	−176.6 (2)
C4A—C5A—C33A—C34A	1.0 (4)	C30B—C31B—C32B—C27B	−1.8 (4)
C5A—C33A—C34A—C35A	−0.2 (4)	C4B—C5B—C33B—C34B	−0.4 (4)
C33A—C34A—C35A—C3A	−0.4 (4)	C5B—C33B—C34B—C35B	0.8 (5)
N3A—C3A—C35A—C34A	178.4 (2)	C33B—C34B—C35B—C3B	0.5 (4)
C4A—C3A—C35A—C34A	0.0 (3)	N3B—C3B—C35B—C34B	178.9 (2)
C4B—N4B—C1B—C2B	−1.0 (3)	C4B—C3B—C35B—C34B	−2.0 (4)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of rings C14B–C19B, C3B–C5B/C33B–C35B and C3A–C5A/C33A–C35A, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C20A—H20A···N4A	0.98	2.28	3.170 (3)	151
C20B—H20B···N4B	0.98	2.45	3.298 (3)	144
C33B—H33B···O3Bⁱ	0.93	2.46	3.271 (5)	145
C8A—H8A···Cg1ⁱⁱ	0.93	2.69	3.536 (3)	151
C25B—H25C···Cg2ⁱⁱⁱ	0.97	2.73	3.629 (3)	155
C31B—H31B···Cg3^iv	0.93	2.99	3.742 (3)	139

Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2; (iii) −x, −y, −z+2; (iv) x−1, y, z.

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Crystal structure of 6-(4-chloro­phen­yl)-6a-nitro-6a,6b,8,9,10,12a-hexa­hydro-6H,7H-spiro[chromeno[3,4-a]indolizine-12,11′-indeno­[1,2-b]quinoxaline]

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure of 6-(4-chlorophenyl)-6a-nitro-6a,6b,8,9,10,12a-hexahydro-6H,7H-spiro[chromeno[3,4-a]indolizine-12,11′-indeno[1,2-b]quinoxaline]