Crystal structure of 2-(2,2,6,6-tetra­methyl­piperidin-4-yl)-6-[(2,2,6,6-tetra­methyl­piperidin-4-yl)amino]-1H-benz[de]iso­quinoline-1,3(2H)-dione

The title compound comprises a 4-amino-1,8-naphthalimide core with a 2,2,6,6-tetra­methyl-4-piperidinyl substituent bonded to each nitro­gen atom and features varying bond lengths as a result of resonance.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.049
• wR factor = 0.142
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        4.6 Ratio
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        5.4 Ratio
PLAT234_ALERT_4_C Large Hirshfeld Difference C16A     --C20A     .       0.16 Ang.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C3A Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C4A Check
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N1'      --H1'      .     Please Check
PLAT420_ALERT_2_C D-H Bond Without Acceptor  N3A      --H3A      .     Please Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      5.259 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.598         11 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         16 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          2 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT012_ALERT_1_G No       _shelx_res_checksum Found in CIF ......     Please Check
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          7 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          2 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          3 Report
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT300_ALERT_4_G Atom Site Occupancy of N3A        Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C1A'       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C13A       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C14A       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C15A       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C16A       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C17A       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C18A       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C19A       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C20A       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of N3B        Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C1B'       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C13B       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C14B       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C15B       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C16B       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C17B       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C18B       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C19B       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C20B       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3A        Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H13C       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H13D       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14C       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14D       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1A'       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H17D       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H17E       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H17F       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H18D       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H18E       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H18F       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H19A       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H19B       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H19C       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H20A       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H20B       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H20C       Constrained at       0.61 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H3B        Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H13A       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H13B       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14A       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H14B       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H17A       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H17B       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H17C       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H1B'       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H18A       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H18B       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H18C       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H19D       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H19E       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H19F       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H20D       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H20E       Constrained at       0.39 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H20F       Constrained at       0.39 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        28% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         20 Note
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        156 Note
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        46% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

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

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

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2022); cell refinement: CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2-(2,2,6,6-Tetramethylpiperidin-4-yl)-6-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1H-benz[de]isoquinoline-1,3(2H)-dione

Crystal data

C30H42N4O2	Dx = 1.130 Mg m^−3
Mr = 490.67	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 6091 reflections
a = 12.0297 (7) Å	θ = 2.1–23.5°
b = 14.6357 (7) Å	µ = 0.07 mm^−1
c = 32.763 (2) Å	T = 293 K
V = 5768.4 (6) Å^3	Needle, orange
Z = 8	0.56 × 0.27 × 0.18 mm
F(000) = 2128

Data collection

XtaLAB Mini II diffractometer	3812 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.031
ω scans	θmax = 25.2°, θmin = 2.1°
Absorption correction: analytical [CrysAlisPro; Rigaku OD, 2022; analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995)]	h = −14→14
Tmin = 0.962, Tmax = 0.990	k = −17→16
80396 measured reflections	l = −39→39
5164 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0686P)^2 + 1.5942P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.142	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.25 e Å^−3
5164 reflections	Δρmin = −0.15 e Å^−3
428 parameters	Extinction correction: SHELXL-2016/6 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
156 restraints	Extinction coefficient: 0.0014 (3)

Special details

Experimental. A clear, orange rod-like crystal of C₃₀H₄₂N₄O₂ was grown from slow evaporation of acetone. The crystal of dimensions 0.178 x 0.265 x 0.563 mm was mounted on MiTeGen loop with Parabar oil and diffraction data was collected. Diffraction data was collected with a Rigaku XtaLAB Mini II benchtop X-ray diffractometer with a fine-focus sealed Mo-target X-ray tube (λ = 0.71073 Å) operated at 600 W power (50 kV, 12 mA) and a HyPix-Bantam Hybrid Photon Counting (HPC) Detector. The X-ray intensities were measured at 293 (2) K; the detector was placed at a distance 4.50 cm from the crystal. The collected frames were integrated with the CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2022) software package using a narrow-frame algorithm. Data were corrected for absorption effects using a multifaceted crystal analytical numeric absorption correction (Clark & Reid, 1995) and spherical harmonic empirical absorption correction implemented in the SCALE3 ABSPACK scaling algorithm. With the use of a Mo fine focus beam, both standard multi-scan and combined multi-scan/analytical absorption corrections yielding similar results, and the linear absorption coefficient of 0.071 it was surmised that shape anisotropy had negligible influence on absorption and the crystal analyzed showed the highest quality. The space group was assigned using the GRAL algorithm within the CrysAlisPro 1.171.41.89a software package, solved with ShelXT (Sheldrick, 2015a) and refined with ShelXL (Sheldrick, 2015b) and the graphical interface Olex2 v1.3 (Dolomanov et al., 2009). The asymmetric unit includes one unit of the C₃₀H₄₂N₄O₂ molecule. All non-hydrogen atoms were refined anisotropically.

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.54190 (10)	0.79035 (8)	0.63165 (4)	0.0600 (4)
N1	0.48104 (11)	0.68697 (9)	0.58470 (4)	0.0497 (4)
O2	0.42262 (12)	0.58100 (10)	0.53855 (4)	0.0785 (5)
N2	0.90392 (13)	0.47902 (10)	0.66263 (5)	0.0620 (4)
H2	0.908310	0.426096	0.651341	0.074*
C11	0.65878 (13)	0.56849 (10)	0.60677 (4)	0.0385 (4)
C2	0.64762 (13)	0.65558 (10)	0.62532 (5)	0.0419 (4)
C6	0.74695 (14)	0.50901 (11)	0.61780 (5)	0.0429 (4)
N1'	1.18903 (15)	0.50136 (12)	0.73813 (6)	0.0739 (5)
C1	0.55558 (14)	0.71571 (11)	0.61494 (5)	0.0450 (4)
C10	0.58162 (13)	0.54143 (11)	0.57671 (5)	0.0427 (4)
C5	0.82443 (14)	0.53746 (11)	0.64913 (5)	0.0484 (4)
C12	0.48992 (14)	0.60266 (12)	0.56483 (5)	0.0501 (4)
C3	0.72623 (15)	0.68194 (11)	0.65358 (5)	0.0512 (4)
H3	0.720899	0.739710	0.665246	0.061*
C4	0.81258 (15)	0.62551 (12)	0.66515 (6)	0.0562 (5)
H4	0.864195	0.646555	0.684079	0.067*
C7	0.75413 (16)	0.42440 (12)	0.59757 (6)	0.0559 (5)
H7	0.810881	0.384085	0.604437	0.067*
C9	0.59299 (16)	0.45839 (12)	0.55745 (5)	0.0555 (5)
H9	0.542658	0.441241	0.537315	0.067*
C1A	0.98242 (15)	0.50075 (12)	0.69519 (6)	0.0561 (5)
H1A	0.943213	0.536848	0.715863	0.067*
C1B'	0.386 (3)	0.7491 (18)	0.5753 (6)	0.0582 (9)	0.39
C8	0.67939 (17)	0.40020 (13)	0.56801 (6)	0.0638 (5)
H8	0.686560	0.344196	0.554862	0.077*
C5A	1.02551 (18)	0.41457 (13)	0.71540 (7)	0.0674 (6)
H5AA	1.065081	0.378156	0.695379	0.081*
H5AB	0.963128	0.378804	0.725231	0.081*
C2A	1.08065 (17)	0.55632 (14)	0.68009 (7)	0.0682 (6)
H2AA	1.053570	0.610657	0.666361	0.082*
H2AB	1.122249	0.520536	0.660405	0.082*
C4A	1.10345 (18)	0.43604 (13)	0.75119 (7)	0.0688 (6)
C3A	1.15818 (17)	0.58465 (14)	0.71509 (7)	0.0708 (6)
C6A	1.1047 (2)	0.65994 (15)	0.74091 (8)	0.0918 (8)
H6AA	1.032065	0.640762	0.749458	0.138*
H6AB	1.098644	0.714763	0.724982	0.138*
H6AC	1.150006	0.671495	0.764482	0.138*
C8A	1.1671 (2)	0.34944 (16)	0.76296 (10)	0.1126 (11)
H8AA	1.209770	0.328589	0.740009	0.169*
H8AB	1.115442	0.302784	0.770945	0.169*
H8AC	1.216185	0.362631	0.785316	0.169*
C16B	0.3244 (8)	0.8717 (5)	0.5282 (2)	0.0769 (8)	0.39
C9A	1.0374 (2)	0.4680 (2)	0.78833 (8)	0.1004 (8)
H9AA	1.087714	0.484540	0.809835	0.151*
H9AB	0.989720	0.419561	0.797492	0.151*
H9AC	0.993090	0.520090	0.781022	0.151*
C7A	1.2668 (2)	0.6219 (2)	0.69801 (10)	0.1129 (10)
H7AA	1.316345	0.636092	0.720086	0.169*
H7AB	1.252150	0.676229	0.682504	0.169*
H7AC	1.300436	0.576826	0.680659	0.169*
C15B	0.1852 (5)	0.7834 (5)	0.5713 (3)	0.0908 (19)	0.39
C13B	0.4103 (6)	0.7963 (5)	0.5371 (2)	0.0734 (15)	0.39
H13A	0.410160	0.752463	0.514920	0.088*	0.39
H13B	0.483811	0.823225	0.538643	0.088*	0.39
C14B	0.2731 (4)	0.7072 (4)	0.5771 (2)	0.0772 (14)	0.39
H14A	0.262301	0.677489	0.603306	0.093*	0.39
H14B	0.265368	0.661575	0.555842	0.093*	0.39
C17B	0.1659 (9)	0.8375 (7)	0.6110 (3)	0.120 (3)	0.39
H17A	0.137450	0.797248	0.631645	0.180*	0.39
H17B	0.113354	0.885591	0.606075	0.180*	0.39
H17C	0.235004	0.863374	0.620072	0.180*	0.39
C18B	0.0732 (6)	0.7362 (7)	0.5625 (4)	0.127 (3)	0.39
H18A	0.081066	0.696025	0.539565	0.191*	0.39
H18B	0.017887	0.781617	0.556578	0.191*	0.39
H18C	0.050719	0.701631	0.586031	0.191*	0.39
C1A'	0.3888 (17)	0.7484 (11)	0.5710 (4)	0.0582 (8)	0.61
H1A'	0.352130	0.716321	0.548459	0.070*	0.61
C14A	0.3019 (3)	0.7590 (3)	0.60353 (11)	0.0649 (8)	0.61
H14C	0.334600	0.790061	0.626759	0.078*	0.61
H14D	0.278571	0.698843	0.612531	0.078*	0.61
C15A	0.1991 (3)	0.8127 (3)	0.58943 (13)	0.0769 (8)	0.61
C18A	0.1236 (5)	0.7516 (4)	0.5629 (2)	0.116 (2)	0.61
H18D	0.166708	0.724795	0.541377	0.174*	0.61
H18E	0.065057	0.787957	0.551396	0.174*	0.61
H18F	0.092089	0.704175	0.579508	0.174*	0.61
C17A	0.1309 (6)	0.8422 (5)	0.62700 (18)	0.1162 (19)	0.61
H17D	0.107125	0.788960	0.641754	0.174*	0.61
H17E	0.066979	0.876227	0.618248	0.174*	0.61
H17F	0.176017	0.879688	0.644407	0.174*	0.61
N3A	0.2379 (3)	0.8959 (2)	0.56933 (10)	0.0702 (7)	0.61
C19A	0.3559 (5)	0.9944 (3)	0.5302 (2)	0.151 (3)	0.61
H19A	0.293617	1.027895	0.519594	0.227*	0.61
H19B	0.415350	0.995374	0.510615	0.227*	0.61
H19C	0.380507	1.022024	0.555158	0.227*	0.61
C13A	0.4234 (3)	0.8408 (3)	0.55399 (13)	0.0711 (10)	0.61
H13C	0.475435	0.831970	0.531738	0.085*	0.61
H13D	0.460498	0.875789	0.575132	0.085*	0.61
C20A	0.2847 (6)	0.8554 (5)	0.49672 (15)	0.153 (4)	0.61
H20A	0.342869	0.864610	0.477088	0.229*	0.61
H20B	0.218459	0.885891	0.487692	0.229*	0.61
H20C	0.270180	0.791181	0.499477	0.229*	0.61
N3B	0.2136 (4)	0.8350 (4)	0.53552 (19)	0.0963 (15)	0.39
H3B	0.163899	0.875434	0.530133	0.116*	0.39
C19B	0.3506 (7)	0.9570 (5)	0.5541 (3)	0.126 (3)	0.39
H19D	0.375302	0.938363	0.580689	0.189*	0.39
H19E	0.284770	0.993621	0.556705	0.189*	0.39
H19F	0.407880	0.991982	0.541031	0.189*	0.39
C20B	0.3297 (13)	0.8977 (11)	0.4826 (3)	0.176 (7)	0.39
H20D	0.303123	0.847607	0.466422	0.264*	0.39
H20E	0.405137	0.911249	0.475269	0.264*	0.39
H20F	0.284057	0.950434	0.477849	0.264*	0.39
H1'	1.230 (3)	0.513 (2)	0.7596 (10)	0.156 (13)*
H1B'	0.388 (4)	0.792 (2)	0.5982 (8)	0.049 (12)*	0.39
C16A	0.3210 (5)	0.8948 (3)	0.53838 (14)	0.0769 (8)	0.61
H3A	0.189 (3)	0.932 (3)	0.5619 (12)	0.088 (13)*	0.61

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0614 (8)	0.0420 (7)	0.0765 (9)	0.0064 (6)	−0.0148 (7)	−0.0154 (6)
N1	0.0488 (8)	0.0465 (8)	0.0539 (8)	0.0030 (6)	−0.0119 (7)	−0.0058 (6)
O2	0.0732 (9)	0.0864 (10)	0.0759 (9)	0.0147 (8)	−0.0352 (8)	−0.0298 (8)
N2	0.0676 (10)	0.0485 (9)	0.0699 (10)	0.0146 (8)	−0.0251 (8)	−0.0177 (7)
C11	0.0439 (8)	0.0363 (8)	0.0354 (8)	−0.0046 (7)	0.0012 (7)	−0.0020 (6)
C2	0.0484 (9)	0.0368 (8)	0.0404 (8)	−0.0024 (7)	−0.0042 (7)	−0.0036 (7)
C6	0.0479 (9)	0.0378 (8)	0.0429 (8)	−0.0026 (7)	−0.0020 (7)	−0.0046 (7)
N1'	0.0624 (11)	0.0655 (11)	0.0938 (14)	0.0067 (9)	−0.0289 (10)	0.0072 (10)
C1	0.0480 (9)	0.0388 (9)	0.0482 (9)	−0.0044 (7)	−0.0034 (7)	−0.0014 (7)
C10	0.0447 (9)	0.0440 (9)	0.0394 (8)	−0.0058 (7)	−0.0012 (7)	−0.0042 (7)
C5	0.0519 (10)	0.0437 (9)	0.0495 (9)	0.0029 (8)	−0.0095 (8)	−0.0054 (7)
C12	0.0496 (10)	0.0556 (11)	0.0450 (9)	−0.0036 (8)	−0.0068 (8)	−0.0067 (8)
C3	0.0619 (11)	0.0366 (9)	0.0550 (10)	0.0025 (8)	−0.0139 (9)	−0.0114 (7)
C4	0.0609 (11)	0.0471 (10)	0.0604 (11)	0.0038 (9)	−0.0230 (9)	−0.0145 (8)
C7	0.0611 (11)	0.0445 (10)	0.0622 (11)	0.0063 (8)	−0.0090 (9)	−0.0120 (8)
C9	0.0588 (11)	0.0535 (10)	0.0543 (10)	−0.0052 (9)	−0.0117 (9)	−0.0155 (8)
C1A	0.0568 (11)	0.0509 (10)	0.0607 (11)	0.0090 (9)	−0.0184 (9)	−0.0078 (8)
C1B'	0.0549 (12)	0.0563 (13)	0.064 (2)	0.0103 (11)	−0.0130 (18)	−0.0010 (15)
C8	0.0727 (13)	0.0472 (10)	0.0716 (12)	0.0049 (9)	−0.0137 (10)	−0.0236 (9)
C5A	0.0678 (12)	0.0518 (11)	0.0825 (14)	0.0083 (10)	−0.0217 (11)	−0.0027 (10)
C2A	0.0664 (13)	0.0653 (13)	0.0730 (13)	0.0063 (10)	−0.0119 (11)	0.0037 (10)
C4A	0.0690 (13)	0.0555 (11)	0.0817 (14)	0.0073 (10)	−0.0262 (11)	0.0087 (10)
C3A	0.0605 (12)	0.0657 (13)	0.0863 (15)	−0.0003 (10)	−0.0237 (11)	0.0095 (11)
C6A	0.1029 (18)	0.0602 (13)	0.1121 (19)	0.0030 (13)	−0.0456 (16)	−0.0121 (13)
C8A	0.110 (2)	0.0690 (15)	0.159 (3)	0.0135 (14)	−0.060 (2)	0.0283 (16)
C16B	0.0726 (11)	0.0780 (18)	0.0800 (19)	0.0214 (12)	−0.0034 (12)	0.0157 (13)
C9A	0.106 (2)	0.121 (2)	0.0738 (16)	−0.0005 (17)	−0.0189 (15)	0.0094 (15)
C7A	0.0765 (17)	0.112 (2)	0.150 (3)	−0.0180 (16)	−0.0271 (17)	0.030 (2)
C15B	0.053 (2)	0.098 (5)	0.122 (5)	0.019 (2)	−0.007 (3)	0.023 (3)
C13B	0.065 (3)	0.073 (3)	0.082 (4)	0.008 (3)	−0.014 (3)	0.020 (3)
C14B	0.057 (2)	0.076 (3)	0.099 (4)	0.0080 (19)	−0.009 (3)	0.015 (3)
C17B	0.100 (8)	0.127 (6)	0.133 (5)	0.051 (5)	−0.005 (5)	0.008 (5)
C18B	0.055 (3)	0.124 (6)	0.202 (9)	0.009 (3)	−0.014 (5)	0.023 (5)
C1A'	0.0548 (11)	0.0563 (12)	0.063 (2)	0.0096 (10)	−0.0128 (17)	−0.0008 (15)
C14A	0.0532 (16)	0.064 (2)	0.077 (2)	0.0032 (14)	−0.0037 (14)	0.0146 (16)
C15A	0.0726 (11)	0.0780 (18)	0.0800 (19)	0.0214 (12)	−0.0034 (12)	0.0157 (13)
C18A	0.055 (3)	0.096 (3)	0.197 (5)	0.013 (2)	−0.036 (3)	−0.006 (3)
C17A	0.085 (4)	0.145 (5)	0.119 (3)	0.039 (3)	0.034 (3)	0.028 (3)
N3A	0.0652 (16)	0.0639 (16)	0.0816 (19)	0.0207 (13)	−0.0055 (13)	0.0049 (13)
C19A	0.121 (4)	0.102 (3)	0.232 (8)	0.032 (3)	0.033 (4)	0.100 (4)
C13A	0.069 (2)	0.068 (2)	0.076 (3)	0.0194 (18)	0.0102 (19)	0.0203 (18)
C20A	0.185 (8)	0.215 (8)	0.058 (3)	0.123 (7)	−0.019 (4)	0.017 (4)
N3B	0.0698 (19)	0.099 (4)	0.120 (4)	0.013 (2)	−0.030 (2)	0.030 (3)
C19B	0.101 (5)	0.087 (4)	0.191 (8)	0.023 (4)	−0.042 (6)	−0.015 (4)
C20B	0.192 (13)	0.214 (14)	0.121 (9)	0.030 (10)	−0.032 (9)	0.098 (9)
C16A	0.0726 (11)	0.0780 (18)	0.0800 (19)	0.0214 (12)	−0.0034 (12)	0.0157 (13)

Geometric parameters (Å, º)

O1—C1	1.2328 (19)	C9A—H9AA	0.9600
N1—C1	1.401 (2)	C9A—H9AB	0.9600
N1—C12	1.399 (2)	C9A—H9AC	0.9600
N1—C1B'	1.49 (3)	C7A—H7AA	0.9600
N1—C1A'	1.497 (19)	C7A—H7AB	0.9600
O2—C12	1.224 (2)	C7A—H7AC	0.9600
N2—H2	0.8600	C15B—C14B	1.549 (9)
N2—C5	1.357 (2)	C15B—C17B	1.542 (3)
N2—C1A	1.460 (2)	C15B—C18B	1.542 (3)
C11—C2	1.418 (2)	C15B—N3B	1.434 (9)
C11—C6	1.419 (2)	C13B—H13A	0.9700
C11—C10	1.410 (2)	C13B—H13B	0.9700
C2—C1	1.455 (2)	C14B—H14A	0.9700
C2—C3	1.379 (2)	C14B—H14B	0.9700
C6—C5	1.448 (2)	C17B—H17A	0.9600
C6—C7	1.407 (2)	C17B—H17B	0.9600
N1'—C4A	1.469 (3)	C17B—H17C	0.9600
N1'—C3A	1.481 (3)	C18B—H18A	0.9600
N1'—H1'	0.87 (3)	C18B—H18B	0.9600
C10—C12	1.473 (2)	C18B—H18C	0.9600
C10—C9	1.376 (2)	C1A'—H1A'	0.9800
C5—C4	1.399 (2)	C1A'—C14A	1.500 (14)
C3—H3	0.9300	C1A'—C13A	1.522 (17)
C3—C4	1.380 (2)	C14A—H14C	0.9700
C4—H4	0.9300	C14A—H14D	0.9700
C7—H7	0.9300	C14A—C15A	1.536 (5)
C7—C8	1.368 (3)	C15A—C18A	1.542 (3)
C9—H9	0.9300	C15A—C17A	1.541 (3)
C9—C8	1.387 (3)	C15A—N3A	1.462 (5)
C1A—H1A	0.9800	C18A—H18D	0.9600
C1A—C5A	1.516 (3)	C18A—H18E	0.9600
C1A—C2A	1.517 (3)	C18A—H18F	0.9600
C1B'—C13B	1.46 (2)	C17A—H17D	0.9600
C1B'—C14B	1.49 (3)	C17A—H17E	0.9600
C1B'—H1B'	0.9800 (11)	C17A—H17F	0.9600
C8—H8	0.9300	N3A—C16A	1.424 (6)
C5A—H5AA	0.9700	N3A—H3A	0.83 (4)
C5A—H5AB	0.9700	C19A—H19A	0.9600
C5A—C4A	1.534 (3)	C19A—H19B	0.9600
C2A—H2AA	0.9700	C19A—H19C	0.9600
C2A—H2AB	0.9700	C19A—C16A	1.541 (3)
C2A—C3A	1.535 (3)	C13A—H13C	0.9700
C4A—C8A	1.530 (3)	C13A—H13D	0.9700
C4A—C9A	1.527 (3)	C13A—C16A	1.549 (7)
C3A—C6A	1.531 (3)	C20A—H20A	0.9600
C3A—C7A	1.522 (3)	C20A—H20B	0.9600
C6A—H6AA	0.9600	C20A—H20C	0.9600
C6A—H6AB	0.9600	C20A—C16A	1.545 (3)
C6A—H6AC	0.9600	N3B—H3B	0.8602
C8A—H8AA	0.9600	C19B—H19D	0.9600
C8A—H8AB	0.9600	C19B—H19E	0.9600
C8A—H8AC	0.9600	C19B—H19F	0.9600
C16B—C13B	1.539 (10)	C20B—H20D	0.9600
C16B—N3B	1.457 (10)	C20B—H20E	0.9600
C16B—C19B	1.542 (3)	C20B—H20F	0.9600
C16B—C20B	1.542 (3)
C1—N1—C1B'	116.9 (10)	C3A—C7A—H7AB	109.5
C1—N1—C1A'	120.4 (7)	C3A—C7A—H7AC	109.5
C12—N1—C1	123.02 (14)	H7AA—C7A—H7AB	109.5
C12—N1—C1B'	120.0 (11)	H7AA—C7A—H7AC	109.5
C12—N1—C1A'	116.5 (6)	H7AB—C7A—H7AC	109.5
C5—N2—H2	118.1	C17B—C15B—C14B	111.6 (7)
C5—N2—C1A	123.83 (14)	C17B—C15B—C18B	104.8 (8)
C1A—N2—H2	118.1	C18B—C15B—C14B	107.3 (6)
C2—C11—C6	120.85 (14)	N3B—C15B—C14B	108.5 (5)
C10—C11—C2	119.30 (14)	N3B—C15B—C17B	117.1 (7)
C10—C11—C6	119.85 (14)	N3B—C15B—C18B	107.0 (7)
C11—C2—C1	121.03 (14)	C1B'—C13B—C16B	111.7 (12)
C3—C2—C11	118.32 (15)	C1B'—C13B—H13A	109.3
C3—C2—C1	120.65 (14)	C1B'—C13B—H13B	109.3
C11—C6—C5	119.04 (14)	C16B—C13B—H13A	109.3
C7—C6—C11	117.76 (14)	C16B—C13B—H13B	109.3
C7—C6—C5	123.20 (15)	H13A—C13B—H13B	107.9
C4A—N1'—C3A	120.58 (16)	C1B'—C14B—C15B	108.7 (11)
C4A—N1'—H1'	107 (2)	C1B'—C14B—H14A	109.9
C3A—N1'—H1'	113 (2)	C1B'—C14B—H14B	109.9
O1—C1—N1	119.64 (15)	C15B—C14B—H14A	109.9
O1—C1—C2	122.27 (15)	C15B—C14B—H14B	109.9
N1—C1—C2	118.09 (14)	H14A—C14B—H14B	108.3
C11—C10—C12	120.43 (14)	C15B—C17B—H17A	109.5
C9—C10—C11	120.18 (16)	C15B—C17B—H17B	109.5
C9—C10—C12	119.37 (15)	C15B—C17B—H17C	109.5
N2—C5—C6	120.23 (15)	H17A—C17B—H17B	109.5
N2—C5—C4	122.02 (15)	H17A—C17B—H17C	109.5
C4—C5—C6	117.74 (15)	H17B—C17B—H17C	109.5
N1—C12—C10	118.07 (14)	C15B—C18B—H18A	109.5
O2—C12—N1	120.35 (16)	C15B—C18B—H18B	109.5
O2—C12—C10	121.58 (16)	C15B—C18B—H18C	109.5
C2—C3—H3	118.9	H18A—C18B—H18B	109.5
C2—C3—C4	122.22 (15)	H18A—C18B—H18C	109.5
C4—C3—H3	118.9	H18B—C18B—H18C	109.5
C5—C4—H4	119.2	N1—C1A'—H1A'	105.8
C3—C4—C5	121.67 (15)	N1—C1A'—C14A	111.5 (9)
C3—C4—H4	119.2	N1—C1A'—C13A	116.1 (13)
C6—C7—H7	119.3	C14A—C1A'—H1A'	105.8
C8—C7—C6	121.40 (17)	C14A—C1A'—C13A	111.0 (10)
C8—C7—H7	119.3	C13A—C1A'—H1A'	105.8
C10—C9—H9	119.9	C1A'—C14A—H14C	108.8
C10—C9—C8	120.15 (16)	C1A'—C14A—H14D	108.8
C8—C9—H9	119.9	C1A'—C14A—C15A	113.6 (7)
N2—C1A—H1A	108.1	H14C—C14A—H14D	107.7
N2—C1A—C5A	111.05 (15)	C15A—C14A—H14C	108.8
N2—C1A—C2A	112.48 (16)	C15A—C14A—H14D	108.8
C5A—C1A—H1A	108.1	C14A—C15A—C18A	110.3 (4)
C5A—C1A—C2A	108.79 (16)	C14A—C15A—C17A	109.4 (4)
C2A—C1A—H1A	108.1	C17A—C15A—C18A	107.4 (5)
N1—C1B'—C14B	116.0 (17)	N3A—C15A—C14A	107.7 (3)
N1—C1B'—H1B'	102 (3)	N3A—C15A—C18A	114.7 (4)
C13B—C1B'—N1	108.3 (16)	N3A—C15A—C17A	107.2 (4)
C13B—C1B'—C14B	114.2 (19)	C15A—C18A—H18D	109.5
C13B—C1B'—H1B'	110 (3)	C15A—C18A—H18E	109.5
C14B—C1B'—H1B'	105 (3)	C15A—C18A—H18F	109.5
C7—C8—C9	120.65 (16)	H18D—C18A—H18E	109.5
C7—C8—H8	119.7	H18D—C18A—H18F	109.5
C9—C8—H8	119.7	H18E—C18A—H18F	109.5
C1A—C5A—H5AA	109.2	C15A—C17A—H17D	109.5
C1A—C5A—H5AB	109.2	C15A—C17A—H17E	109.5
C1A—C5A—C4A	111.87 (15)	C15A—C17A—H17F	109.5
H5AA—C5A—H5AB	107.9	H17D—C17A—H17E	109.5
C4A—C5A—H5AA	109.2	H17D—C17A—H17F	109.5
C4A—C5A—H5AB	109.2	H17E—C17A—H17F	109.5
C1A—C2A—H2AA	109.2	C15A—N3A—H3A	115 (3)
C1A—C2A—H2AB	109.2	C16A—N3A—C15A	122.3 (3)
C1A—C2A—C3A	112.00 (17)	C16A—N3A—H3A	108 (3)
H2AA—C2A—H2AB	107.9	H19A—C19A—H19B	109.5
C3A—C2A—H2AA	109.2	H19A—C19A—H19C	109.5
C3A—C2A—H2AB	109.2	H19B—C19A—H19C	109.5
N1'—C4A—C5A	109.81 (18)	C16A—C19A—H19A	109.5
N1'—C4A—C8A	105.17 (18)	C16A—C19A—H19B	109.5
N1'—C4A—C9A	113.4 (2)	C16A—C19A—H19C	109.5
C8A—C4A—C5A	109.21 (18)	C1A'—C13A—H13C	109.5
C9A—C4A—C5A	110.71 (19)	C1A'—C13A—H13D	109.5
C9A—C4A—C8A	108.3 (2)	C1A'—C13A—C16A	110.9 (8)
N1'—C3A—C2A	108.10 (17)	H13C—C13A—H13D	108.1
N1'—C3A—C6A	114.6 (2)	C16A—C13A—H13C	109.5
N1'—C3A—C7A	105.48 (18)	C16A—C13A—H13D	109.5
C6A—C3A—C2A	110.61 (17)	H20A—C20A—H20B	109.5
C7A—C3A—C2A	110.1 (2)	H20A—C20A—H20C	109.5
C7A—C3A—C6A	107.8 (2)	H20B—C20A—H20C	109.5
C3A—C6A—H6AA	109.5	C16A—C20A—H20A	109.5
C3A—C6A—H6AB	109.5	C16A—C20A—H20B	109.5
C3A—C6A—H6AC	109.5	C16A—C20A—H20C	109.5
H6AA—C6A—H6AB	109.5	C16B—N3B—H3B	110.4
H6AA—C6A—H6AC	109.5	C15B—N3B—C16B	123.1 (6)
H6AB—C6A—H6AC	109.5	C15B—N3B—H3B	111.4
C4A—C8A—H8AA	109.5	C16B—C19B—H19D	109.5
C4A—C8A—H8AB	109.5	C16B—C19B—H19E	109.5
C4A—C8A—H8AC	109.5	C16B—C19B—H19F	109.5
H8AA—C8A—H8AB	109.5	H19D—C19B—H19E	109.5
H8AA—C8A—H8AC	109.5	H19D—C19B—H19F	109.5
H8AB—C8A—H8AC	109.5	H19E—C19B—H19F	109.5
C13B—C16B—C19B	109.8 (6)	C16B—C20B—H20D	109.5
C13B—C16B—C20B	109.5 (7)	C16B—C20B—H20E	109.5
N3B—C16B—C13B	108.5 (6)	C16B—C20B—H20F	109.5
N3B—C16B—C19B	113.2 (7)	H20D—C20B—H20E	109.5
N3B—C16B—C20B	106.8 (8)	H20D—C20B—H20F	109.5
C20B—C16B—C19B	108.9 (9)	H20E—C20B—H20F	109.5
C4A—C9A—H9AA	109.5	N3A—C16A—C19A	107.7 (4)
C4A—C9A—H9AB	109.5	N3A—C16A—C13A	109.2 (4)
C4A—C9A—H9AC	109.5	N3A—C16A—C20A	115.8 (5)
H9AA—C9A—H9AB	109.5	C19A—C16A—C13A	108.8 (4)
H9AA—C9A—H9AC	109.5	C19A—C16A—C20A	106.0 (6)
H9AB—C9A—H9AC	109.5	C20A—C16A—C13A	109.1 (4)
C3A—C7A—H7AA	109.5
N1—C1B'—C13B—C16B	−172.0 (11)	C9—C10—C12—O2	0.9 (3)
N1—C1B'—C14B—C15B	173.9 (11)	C1A—N2—C5—C6	−177.46 (16)
N1—C1A'—C14A—C15A	−173.6 (8)	C1A—N2—C5—C4	1.3 (3)
N1—C1A'—C13A—C16A	176.2 (6)	C1A—C5A—C4A—N1'	−50.5 (2)
N2—C5—C4—C3	−174.82 (18)	C1A—C5A—C4A—C8A	−165.3 (2)
N2—C1A—C5A—C4A	−177.00 (17)	C1A—C5A—C4A—C9A	75.5 (2)
N2—C1A—C2A—C3A	175.87 (16)	C1A—C2A—C3A—N1'	53.1 (2)
C11—C2—C1—O1	177.45 (16)	C1A—C2A—C3A—C6A	−73.0 (2)
C11—C2—C1—N1	−2.9 (2)	C1A—C2A—C3A—C7A	167.90 (19)
C11—C2—C3—C4	−2.0 (3)	C1B'—N1—C1—O1	−1.6 (10)
C11—C6—C5—N2	174.59 (16)	C1B'—N1—C1—C2	178.7 (10)
C11—C6—C5—C4	−4.2 (2)	C1B'—N1—C12—O2	2.9 (11)
C11—C6—C7—C8	0.5 (3)	C1B'—N1—C12—C10	−176.7 (10)
C11—C10—C12—N1	−1.1 (2)	C5A—C1A—C2A—C3A	−60.7 (2)
C11—C10—C12—O2	179.29 (17)	C2A—C1A—C5A—C4A	58.7 (2)
C11—C10—C9—C8	1.1 (3)	C4A—N1'—C3A—C2A	−48.5 (3)
C2—C11—C6—C5	1.5 (2)	C4A—N1'—C3A—C6A	75.3 (3)
C2—C11—C6—C7	−178.78 (15)	C4A—N1'—C3A—C7A	−166.3 (2)
C2—C11—C10—C12	−0.4 (2)	C3A—N1'—C4A—C5A	47.5 (3)
C2—C11—C10—C9	178.00 (16)	C3A—N1'—C4A—C8A	164.9 (2)
C2—C3—C4—C5	−0.8 (3)	C3A—N1'—C4A—C9A	−76.9 (3)
C6—C11—C2—C1	−178.24 (14)	C13B—C1B'—C14B—C15B	−59.1 (17)
C6—C11—C2—C3	1.6 (2)	C13B—C16B—N3B—C15B	46.5 (9)
C6—C11—C10—C12	−179.75 (15)	C14B—C1B'—C13B—C16B	57.1 (18)
C6—C11—C10—C9	−1.4 (2)	C14B—C15B—N3B—C16B	−49.9 (9)
C6—C5—C4—C3	3.9 (3)	C17B—C15B—C14B—C1B'	−79.7 (11)
C6—C7—C8—C9	−0.8 (3)	C17B—C15B—N3B—C16B	77.5 (9)
C1—N1—C12—O2	−179.84 (17)	C18B—C15B—C14B—C1B'	166.1 (11)
C1—N1—C12—C10	0.5 (2)	C18B—C15B—N3B—C16B	−165.3 (7)
C1—N1—C1B'—C13B	103.3 (14)	C1A'—N1—C1—O1	3.3 (7)
C1—N1—C1B'—C14B	−126.8 (12)	C1A'—N1—C1—C2	−176.4 (7)
C1—N1—C1A'—C14A	−70.1 (13)	C1A'—N1—C12—O2	−2.0 (7)
C1—N1—C1A'—C13A	58.4 (9)	C1A'—N1—C12—C10	178.4 (6)
C1—C2—C3—C4	177.84 (17)	C1A'—C14A—C15A—C18A	77.3 (9)
C10—C11—C2—C1	2.4 (2)	C1A'—C14A—C15A—C17A	−164.8 (9)
C10—C11—C2—C3	−177.74 (15)	C1A'—C14A—C15A—N3A	−48.6 (9)
C10—C11—C6—C5	−179.15 (15)	C1A'—C13A—C16A—N3A	50.7 (7)
C10—C11—C6—C7	0.6 (2)	C1A'—C13A—C16A—C19A	168.0 (7)
C10—C9—C8—C7	0.0 (3)	C1A'—C13A—C16A—C20A	−76.8 (7)
C5—N2—C1A—C5A	155.91 (18)	C14A—C1A'—C13A—C16A	−55.0 (12)
C5—N2—C1A—C2A	−81.9 (2)	C14A—C15A—N3A—C16A	49.8 (5)
C5—C6—C7—C8	−179.77 (18)	C15A—N3A—C16A—C19A	−169.7 (4)
C12—N1—C1—O1	−178.93 (16)	C15A—N3A—C16A—C13A	−51.6 (5)
C12—N1—C1—C2	1.4 (2)	C15A—N3A—C16A—C20A	71.9 (6)
C12—N1—C1B'—C13B	−79.3 (19)	C18A—C15A—N3A—C16A	−73.5 (5)
C12—N1—C1B'—C14B	50.7 (15)	C17A—C15A—N3A—C16A	167.4 (5)
C12—N1—C1A'—C14A	112.0 (9)	C13A—C1A'—C14A—C15A	55.2 (13)
C12—N1—C1A'—C13A	−119.5 (9)	N3B—C16B—C13B—C1B'	−45.7 (15)
C12—C10—C9—C8	179.47 (17)	N3B—C15B—C14B—C1B'	50.8 (11)
C3—C2—C1—O1	−2.4 (3)	C19B—C16B—C13B—C1B'	78.6 (15)
C3—C2—C1—N1	177.21 (16)	C19B—C16B—N3B—C15B	−75.7 (10)
C7—C6—C5—N2	−5.1 (3)	C20B—C16B—C13B—C1B'	−161.9 (15)
C7—C6—C5—C4	176.09 (17)	C20B—C16B—N3B—C15B	164.5 (8)
C9—C10—C12—N1	−179.46 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	0.86	2.17	3.0134 (18)	165
C9—H9···O2^ii	0.93	2.54	3.203 (2)	128

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