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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989022010374/mw2192sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989022010374/mw2192Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989022010374/mw2192Isup3.cml
Supplementary material

CCDC reference: 2215550

Computing details top

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 top
Crystal data top
C30H42N4O2Dx = 1.130 Mg m3
Mr = 490.67Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 6091 reflections
a = 12.0297 (7) Åθ = 2.1–23.5°
b = 14.6357 (7) ŵ = 0.07 mm1
c = 32.763 (2) ÅT = 293 K
V = 5768.4 (6) Å3Needle, orange
Z = 80.56 × 0.27 × 0.18 mm
F(000) = 2128
Data collection top
XtaLAB Mini II
diffractometer
3812 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm-1Rint = 0.031
ω scansθmax = 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 = 1414
Tmin = 0.962, Tmax = 0.990k = 1716
80396 measured reflectionsl = 3939
5164 independent reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.049 w = 1/[σ2(Fo2) + (0.0686P)2 + 1.5942P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.142(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.25 e Å3
5164 reflectionsΔρmin = 0.15 e Å3
428 parametersExtinction correction: SHELXL-2016/6 (Sheldrick 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
156 restraintsExtinction coefficient: 0.0014 (3)
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.54190 (10)0.79035 (8)0.63165 (4)0.0600 (4)
N10.48104 (11)0.68697 (9)0.58470 (4)0.0497 (4)
O20.42262 (12)0.58100 (10)0.53855 (4)0.0785 (5)
N20.90392 (13)0.47902 (10)0.66263 (5)0.0620 (4)
H20.9083100.4260960.6513410.074*
C110.65878 (13)0.56849 (10)0.60677 (4)0.0385 (4)
C20.64762 (13)0.65558 (10)0.62532 (5)0.0419 (4)
C60.74695 (14)0.50901 (11)0.61780 (5)0.0429 (4)
N1'1.18903 (15)0.50136 (12)0.73813 (6)0.0739 (5)
C10.55558 (14)0.71571 (11)0.61494 (5)0.0450 (4)
C100.58162 (13)0.54143 (11)0.57671 (5)0.0427 (4)
C50.82443 (14)0.53746 (11)0.64913 (5)0.0484 (4)
C120.48992 (14)0.60266 (12)0.56483 (5)0.0501 (4)
C30.72623 (15)0.68194 (11)0.65358 (5)0.0512 (4)
H30.7208990.7397100.6652460.061*
C40.81258 (15)0.62551 (12)0.66515 (6)0.0562 (5)
H40.8641950.6465550.6840790.067*
C70.75413 (16)0.42440 (12)0.59757 (6)0.0559 (5)
H70.8108810.3840850.6044370.067*
C90.59299 (16)0.45839 (12)0.55745 (5)0.0555 (5)
H90.5426580.4412410.5373150.067*
C1A0.98242 (15)0.50075 (12)0.69519 (6)0.0561 (5)
H1A0.9432130.5368480.7158630.067*
C1B'0.386 (3)0.7491 (18)0.5753 (6)0.0582 (9)0.39
C80.67939 (17)0.40020 (13)0.56801 (6)0.0638 (5)
H80.6865600.3441960.5548620.077*
C5A1.02551 (18)0.41457 (13)0.71540 (7)0.0674 (6)
H5AA1.0650810.3781560.6953790.081*
H5AB0.9631280.3788040.7252310.081*
C2A1.08065 (17)0.55632 (14)0.68009 (7)0.0682 (6)
H2AA1.0535700.6106570.6663610.082*
H2AB1.1222490.5205360.6604050.082*
C4A1.10345 (18)0.43604 (13)0.75119 (7)0.0688 (6)
C3A1.15818 (17)0.58465 (14)0.71509 (7)0.0708 (6)
C6A1.1047 (2)0.65994 (15)0.74091 (8)0.0918 (8)
H6AA1.0320650.6407620.7494580.138*
H6AB1.0986440.7147630.7249820.138*
H6AC1.1500060.6714950.7644820.138*
C8A1.1671 (2)0.34944 (16)0.76296 (10)0.1126 (11)
H8AA1.2097700.3285890.7400090.169*
H8AB1.1154420.3027840.7709450.169*
H8AC1.2161850.3626310.7853160.169*
C16B0.3244 (8)0.8717 (5)0.5282 (2)0.0769 (8)0.39
C9A1.0374 (2)0.4680 (2)0.78833 (8)0.1004 (8)
H9AA1.0877140.4845400.8098350.151*
H9AB0.9897200.4195610.7974920.151*
H9AC0.9930900.5200900.7810220.151*
C7A1.2668 (2)0.6219 (2)0.69801 (10)0.1129 (10)
H7AA1.3163450.6360920.7200860.169*
H7AB1.2521500.6762290.6825040.169*
H7AC1.3004360.5768260.6806590.169*
C15B0.1852 (5)0.7834 (5)0.5713 (3)0.0908 (19)0.39
C13B0.4103 (6)0.7963 (5)0.5371 (2)0.0734 (15)0.39
H13A0.4101600.7524630.5149200.088*0.39
H13B0.4838110.8232250.5386430.088*0.39
C14B0.2731 (4)0.7072 (4)0.5771 (2)0.0772 (14)0.39
H14A0.2623010.6774890.6033060.093*0.39
H14B0.2653680.6615750.5558420.093*0.39
C17B0.1659 (9)0.8375 (7)0.6110 (3)0.120 (3)0.39
H17A0.1374500.7972480.6316450.180*0.39
H17B0.1133540.8855910.6060750.180*0.39
H17C0.2350040.8633740.6200720.180*0.39
C18B0.0732 (6)0.7362 (7)0.5625 (4)0.127 (3)0.39
H18A0.0810660.6960250.5395650.191*0.39
H18B0.0178870.7816170.5565780.191*0.39
H18C0.0507190.7016310.5860310.191*0.39
C1A'0.3888 (17)0.7484 (11)0.5710 (4)0.0582 (8)0.61
H1A'0.3521300.7163210.5484590.070*0.61
C14A0.3019 (3)0.7590 (3)0.60353 (11)0.0649 (8)0.61
H14C0.3346000.7900610.6267590.078*0.61
H14D0.2785710.6988430.6125310.078*0.61
C15A0.1991 (3)0.8127 (3)0.58943 (13)0.0769 (8)0.61
C18A0.1236 (5)0.7516 (4)0.5629 (2)0.116 (2)0.61
H18D0.1667080.7247950.5413770.174*0.61
H18E0.0650570.7879570.5513960.174*0.61
H18F0.0920890.7041750.5795080.174*0.61
C17A0.1309 (6)0.8422 (5)0.62700 (18)0.1162 (19)0.61
H17D0.1071250.7889600.6417540.174*0.61
H17E0.0669790.8762270.6182480.174*0.61
H17F0.1760170.8796880.6444070.174*0.61
N3A0.2379 (3)0.8959 (2)0.56933 (10)0.0702 (7)0.61
C19A0.3559 (5)0.9944 (3)0.5302 (2)0.151 (3)0.61
H19A0.2936171.0278950.5195940.227*0.61
H19B0.4153500.9953740.5106150.227*0.61
H19C0.3805071.0220240.5551580.227*0.61
C13A0.4234 (3)0.8408 (3)0.55399 (13)0.0711 (10)0.61
H13C0.4754350.8319700.5317380.085*0.61
H13D0.4604980.8757890.5751320.085*0.61
C20A0.2847 (6)0.8554 (5)0.49672 (15)0.153 (4)0.61
H20A0.3428690.8646100.4770880.229*0.61
H20B0.2184590.8858910.4876920.229*0.61
H20C0.2701800.7911810.4994770.229*0.61
N3B0.2136 (4)0.8350 (4)0.53552 (19)0.0963 (15)0.39
H3B0.1638990.8754340.5301330.116*0.39
C19B0.3506 (7)0.9570 (5)0.5541 (3)0.126 (3)0.39
H19D0.3753020.9383630.5806890.189*0.39
H19E0.2847700.9936210.5567050.189*0.39
H19F0.4078800.9919820.5410310.189*0.39
C20B0.3297 (13)0.8977 (11)0.4826 (3)0.176 (7)0.39
H20D0.3031230.8476070.4664220.264*0.39
H20E0.4051370.9112490.4752690.264*0.39
H20F0.2840570.9504340.4778490.264*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
C16A0.3210 (5)0.8948 (3)0.53838 (14)0.0769 (8)0.61
H3A0.189 (3)0.932 (3)0.5619 (12)0.088 (13)*0.61
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0614 (8)0.0420 (7)0.0765 (9)0.0064 (6)0.0148 (7)0.0154 (6)
N10.0488 (8)0.0465 (8)0.0539 (8)0.0030 (6)0.0119 (7)0.0058 (6)
O20.0732 (9)0.0864 (10)0.0759 (9)0.0147 (8)0.0352 (8)0.0298 (8)
N20.0676 (10)0.0485 (9)0.0699 (10)0.0146 (8)0.0251 (8)0.0177 (7)
C110.0439 (8)0.0363 (8)0.0354 (8)0.0046 (7)0.0012 (7)0.0020 (6)
C20.0484 (9)0.0368 (8)0.0404 (8)0.0024 (7)0.0042 (7)0.0036 (7)
C60.0479 (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)
C10.0480 (9)0.0388 (9)0.0482 (9)0.0044 (7)0.0034 (7)0.0014 (7)
C100.0447 (9)0.0440 (9)0.0394 (8)0.0058 (7)0.0012 (7)0.0042 (7)
C50.0519 (10)0.0437 (9)0.0495 (9)0.0029 (8)0.0095 (8)0.0054 (7)
C120.0496 (10)0.0556 (11)0.0450 (9)0.0036 (8)0.0068 (8)0.0067 (8)
C30.0619 (11)0.0366 (9)0.0550 (10)0.0025 (8)0.0139 (9)0.0114 (7)
C40.0609 (11)0.0471 (10)0.0604 (11)0.0038 (9)0.0230 (9)0.0145 (8)
C70.0611 (11)0.0445 (10)0.0622 (11)0.0063 (8)0.0090 (9)0.0120 (8)
C90.0588 (11)0.0535 (10)0.0543 (10)0.0052 (9)0.0117 (9)0.0155 (8)
C1A0.0568 (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)
C80.0727 (13)0.0472 (10)0.0716 (12)0.0049 (9)0.0137 (10)0.0236 (9)
C5A0.0678 (12)0.0518 (11)0.0825 (14)0.0083 (10)0.0217 (11)0.0027 (10)
C2A0.0664 (13)0.0653 (13)0.0730 (13)0.0063 (10)0.0119 (11)0.0037 (10)
C4A0.0690 (13)0.0555 (11)0.0817 (14)0.0073 (10)0.0262 (11)0.0087 (10)
C3A0.0605 (12)0.0657 (13)0.0863 (15)0.0003 (10)0.0237 (11)0.0095 (11)
C6A0.1029 (18)0.0602 (13)0.1121 (19)0.0030 (13)0.0456 (16)0.0121 (13)
C8A0.110 (2)0.0690 (15)0.159 (3)0.0135 (14)0.060 (2)0.0283 (16)
C16B0.0726 (11)0.0780 (18)0.0800 (19)0.0214 (12)0.0034 (12)0.0157 (13)
C9A0.106 (2)0.121 (2)0.0738 (16)0.0005 (17)0.0189 (15)0.0094 (15)
C7A0.0765 (17)0.112 (2)0.150 (3)0.0180 (16)0.0271 (17)0.030 (2)
C15B0.053 (2)0.098 (5)0.122 (5)0.019 (2)0.007 (3)0.023 (3)
C13B0.065 (3)0.073 (3)0.082 (4)0.008 (3)0.014 (3)0.020 (3)
C14B0.057 (2)0.076 (3)0.099 (4)0.0080 (19)0.009 (3)0.015 (3)
C17B0.100 (8)0.127 (6)0.133 (5)0.051 (5)0.005 (5)0.008 (5)
C18B0.055 (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)
C14A0.0532 (16)0.064 (2)0.077 (2)0.0032 (14)0.0037 (14)0.0146 (16)
C15A0.0726 (11)0.0780 (18)0.0800 (19)0.0214 (12)0.0034 (12)0.0157 (13)
C18A0.055 (3)0.096 (3)0.197 (5)0.013 (2)0.036 (3)0.006 (3)
C17A0.085 (4)0.145 (5)0.119 (3)0.039 (3)0.034 (3)0.028 (3)
N3A0.0652 (16)0.0639 (16)0.0816 (19)0.0207 (13)0.0055 (13)0.0049 (13)
C19A0.121 (4)0.102 (3)0.232 (8)0.032 (3)0.033 (4)0.100 (4)
C13A0.069 (2)0.068 (2)0.076 (3)0.0194 (18)0.0102 (19)0.0203 (18)
C20A0.185 (8)0.215 (8)0.058 (3)0.123 (7)0.019 (4)0.017 (4)
N3B0.0698 (19)0.099 (4)0.120 (4)0.013 (2)0.030 (2)0.030 (3)
C19B0.101 (5)0.087 (4)0.191 (8)0.023 (4)0.042 (6)0.015 (4)
C20B0.192 (13)0.214 (14)0.121 (9)0.030 (10)0.032 (9)0.098 (9)
C16A0.0726 (11)0.0780 (18)0.0800 (19)0.0214 (12)0.0034 (12)0.0157 (13)
Geometric parameters (Å, º) top
O1—C11.2328 (19)C9A—H9AA0.9600
N1—C11.401 (2)C9A—H9AB0.9600
N1—C121.399 (2)C9A—H9AC0.9600
N1—C1B'1.49 (3)C7A—H7AA0.9600
N1—C1A'1.497 (19)C7A—H7AB0.9600
O2—C121.224 (2)C7A—H7AC0.9600
N2—H20.8600C15B—C14B1.549 (9)
N2—C51.357 (2)C15B—C17B1.542 (3)
N2—C1A1.460 (2)C15B—C18B1.542 (3)
C11—C21.418 (2)C15B—N3B1.434 (9)
C11—C61.419 (2)C13B—H13A0.9700
C11—C101.410 (2)C13B—H13B0.9700
C2—C11.455 (2)C14B—H14A0.9700
C2—C31.379 (2)C14B—H14B0.9700
C6—C51.448 (2)C17B—H17A0.9600
C6—C71.407 (2)C17B—H17B0.9600
N1'—C4A1.469 (3)C17B—H17C0.9600
N1'—C3A1.481 (3)C18B—H18A0.9600
N1'—H1'0.87 (3)C18B—H18B0.9600
C10—C121.473 (2)C18B—H18C0.9600
C10—C91.376 (2)C1A'—H1A'0.9800
C5—C41.399 (2)C1A'—C14A1.500 (14)
C3—H30.9300C1A'—C13A1.522 (17)
C3—C41.380 (2)C14A—H14C0.9700
C4—H40.9300C14A—H14D0.9700
C7—H70.9300C14A—C15A1.536 (5)
C7—C81.368 (3)C15A—C18A1.542 (3)
C9—H90.9300C15A—C17A1.541 (3)
C9—C81.387 (3)C15A—N3A1.462 (5)
C1A—H1A0.9800C18A—H18D0.9600
C1A—C5A1.516 (3)C18A—H18E0.9600
C1A—C2A1.517 (3)C18A—H18F0.9600
C1B'—C13B1.46 (2)C17A—H17D0.9600
C1B'—C14B1.49 (3)C17A—H17E0.9600
C1B'—H1B'0.9800 (11)C17A—H17F0.9600
C8—H80.9300N3A—C16A1.424 (6)
C5A—H5AA0.9700N3A—H3A0.83 (4)
C5A—H5AB0.9700C19A—H19A0.9600
C5A—C4A1.534 (3)C19A—H19B0.9600
C2A—H2AA0.9700C19A—H19C0.9600
C2A—H2AB0.9700C19A—C16A1.541 (3)
C2A—C3A1.535 (3)C13A—H13C0.9700
C4A—C8A1.530 (3)C13A—H13D0.9700
C4A—C9A1.527 (3)C13A—C16A1.549 (7)
C3A—C6A1.531 (3)C20A—H20A0.9600
C3A—C7A1.522 (3)C20A—H20B0.9600
C6A—H6AA0.9600C20A—H20C0.9600
C6A—H6AB0.9600C20A—C16A1.545 (3)
C6A—H6AC0.9600N3B—H3B0.8602
C8A—H8AA0.9600C19B—H19D0.9600
C8A—H8AB0.9600C19B—H19E0.9600
C8A—H8AC0.9600C19B—H19F0.9600
C16B—C13B1.539 (10)C20B—H20D0.9600
C16B—N3B1.457 (10)C20B—H20E0.9600
C16B—C19B1.542 (3)C20B—H20F0.9600
C16B—C20B1.542 (3)
C1—N1—C1B'116.9 (10)C3A—C7A—H7AB109.5
C1—N1—C1A'120.4 (7)C3A—C7A—H7AC109.5
C12—N1—C1123.02 (14)H7AA—C7A—H7AB109.5
C12—N1—C1B'120.0 (11)H7AA—C7A—H7AC109.5
C12—N1—C1A'116.5 (6)H7AB—C7A—H7AC109.5
C5—N2—H2118.1C17B—C15B—C14B111.6 (7)
C5—N2—C1A123.83 (14)C17B—C15B—C18B104.8 (8)
C1A—N2—H2118.1C18B—C15B—C14B107.3 (6)
C2—C11—C6120.85 (14)N3B—C15B—C14B108.5 (5)
C10—C11—C2119.30 (14)N3B—C15B—C17B117.1 (7)
C10—C11—C6119.85 (14)N3B—C15B—C18B107.0 (7)
C11—C2—C1121.03 (14)C1B'—C13B—C16B111.7 (12)
C3—C2—C11118.32 (15)C1B'—C13B—H13A109.3
C3—C2—C1120.65 (14)C1B'—C13B—H13B109.3
C11—C6—C5119.04 (14)C16B—C13B—H13A109.3
C7—C6—C11117.76 (14)C16B—C13B—H13B109.3
C7—C6—C5123.20 (15)H13A—C13B—H13B107.9
C4A—N1'—C3A120.58 (16)C1B'—C14B—C15B108.7 (11)
C4A—N1'—H1'107 (2)C1B'—C14B—H14A109.9
C3A—N1'—H1'113 (2)C1B'—C14B—H14B109.9
O1—C1—N1119.64 (15)C15B—C14B—H14A109.9
O1—C1—C2122.27 (15)C15B—C14B—H14B109.9
N1—C1—C2118.09 (14)H14A—C14B—H14B108.3
C11—C10—C12120.43 (14)C15B—C17B—H17A109.5
C9—C10—C11120.18 (16)C15B—C17B—H17B109.5
C9—C10—C12119.37 (15)C15B—C17B—H17C109.5
N2—C5—C6120.23 (15)H17A—C17B—H17B109.5
N2—C5—C4122.02 (15)H17A—C17B—H17C109.5
C4—C5—C6117.74 (15)H17B—C17B—H17C109.5
N1—C12—C10118.07 (14)C15B—C18B—H18A109.5
O2—C12—N1120.35 (16)C15B—C18B—H18B109.5
O2—C12—C10121.58 (16)C15B—C18B—H18C109.5
C2—C3—H3118.9H18A—C18B—H18B109.5
C2—C3—C4122.22 (15)H18A—C18B—H18C109.5
C4—C3—H3118.9H18B—C18B—H18C109.5
C5—C4—H4119.2N1—C1A'—H1A'105.8
C3—C4—C5121.67 (15)N1—C1A'—C14A111.5 (9)
C3—C4—H4119.2N1—C1A'—C13A116.1 (13)
C6—C7—H7119.3C14A—C1A'—H1A'105.8
C8—C7—C6121.40 (17)C14A—C1A'—C13A111.0 (10)
C8—C7—H7119.3C13A—C1A'—H1A'105.8
C10—C9—H9119.9C1A'—C14A—H14C108.8
C10—C9—C8120.15 (16)C1A'—C14A—H14D108.8
C8—C9—H9119.9C1A'—C14A—C15A113.6 (7)
N2—C1A—H1A108.1H14C—C14A—H14D107.7
N2—C1A—C5A111.05 (15)C15A—C14A—H14C108.8
N2—C1A—C2A112.48 (16)C15A—C14A—H14D108.8
C5A—C1A—H1A108.1C14A—C15A—C18A110.3 (4)
C5A—C1A—C2A108.79 (16)C14A—C15A—C17A109.4 (4)
C2A—C1A—H1A108.1C17A—C15A—C18A107.4 (5)
N1—C1B'—C14B116.0 (17)N3A—C15A—C14A107.7 (3)
N1—C1B'—H1B'102 (3)N3A—C15A—C18A114.7 (4)
C13B—C1B'—N1108.3 (16)N3A—C15A—C17A107.2 (4)
C13B—C1B'—C14B114.2 (19)C15A—C18A—H18D109.5
C13B—C1B'—H1B'110 (3)C15A—C18A—H18E109.5
C14B—C1B'—H1B'105 (3)C15A—C18A—H18F109.5
C7—C8—C9120.65 (16)H18D—C18A—H18E109.5
C7—C8—H8119.7H18D—C18A—H18F109.5
C9—C8—H8119.7H18E—C18A—H18F109.5
C1A—C5A—H5AA109.2C15A—C17A—H17D109.5
C1A—C5A—H5AB109.2C15A—C17A—H17E109.5
C1A—C5A—C4A111.87 (15)C15A—C17A—H17F109.5
H5AA—C5A—H5AB107.9H17D—C17A—H17E109.5
C4A—C5A—H5AA109.2H17D—C17A—H17F109.5
C4A—C5A—H5AB109.2H17E—C17A—H17F109.5
C1A—C2A—H2AA109.2C15A—N3A—H3A115 (3)
C1A—C2A—H2AB109.2C16A—N3A—C15A122.3 (3)
C1A—C2A—C3A112.00 (17)C16A—N3A—H3A108 (3)
H2AA—C2A—H2AB107.9H19A—C19A—H19B109.5
C3A—C2A—H2AA109.2H19A—C19A—H19C109.5
C3A—C2A—H2AB109.2H19B—C19A—H19C109.5
N1'—C4A—C5A109.81 (18)C16A—C19A—H19A109.5
N1'—C4A—C8A105.17 (18)C16A—C19A—H19B109.5
N1'—C4A—C9A113.4 (2)C16A—C19A—H19C109.5
C8A—C4A—C5A109.21 (18)C1A'—C13A—H13C109.5
C9A—C4A—C5A110.71 (19)C1A'—C13A—H13D109.5
C9A—C4A—C8A108.3 (2)C1A'—C13A—C16A110.9 (8)
N1'—C3A—C2A108.10 (17)H13C—C13A—H13D108.1
N1'—C3A—C6A114.6 (2)C16A—C13A—H13C109.5
N1'—C3A—C7A105.48 (18)C16A—C13A—H13D109.5
C6A—C3A—C2A110.61 (17)H20A—C20A—H20B109.5
C7A—C3A—C2A110.1 (2)H20A—C20A—H20C109.5
C7A—C3A—C6A107.8 (2)H20B—C20A—H20C109.5
C3A—C6A—H6AA109.5C16A—C20A—H20A109.5
C3A—C6A—H6AB109.5C16A—C20A—H20B109.5
C3A—C6A—H6AC109.5C16A—C20A—H20C109.5
H6AA—C6A—H6AB109.5C16B—N3B—H3B110.4
H6AA—C6A—H6AC109.5C15B—N3B—C16B123.1 (6)
H6AB—C6A—H6AC109.5C15B—N3B—H3B111.4
C4A—C8A—H8AA109.5C16B—C19B—H19D109.5
C4A—C8A—H8AB109.5C16B—C19B—H19E109.5
C4A—C8A—H8AC109.5C16B—C19B—H19F109.5
H8AA—C8A—H8AB109.5H19D—C19B—H19E109.5
H8AA—C8A—H8AC109.5H19D—C19B—H19F109.5
H8AB—C8A—H8AC109.5H19E—C19B—H19F109.5
C13B—C16B—C19B109.8 (6)C16B—C20B—H20D109.5
C13B—C16B—C20B109.5 (7)C16B—C20B—H20E109.5
N3B—C16B—C13B108.5 (6)C16B—C20B—H20F109.5
N3B—C16B—C19B113.2 (7)H20D—C20B—H20E109.5
N3B—C16B—C20B106.8 (8)H20D—C20B—H20F109.5
C20B—C16B—C19B108.9 (9)H20E—C20B—H20F109.5
C4A—C9A—H9AA109.5N3A—C16A—C19A107.7 (4)
C4A—C9A—H9AB109.5N3A—C16A—C13A109.2 (4)
C4A—C9A—H9AC109.5N3A—C16A—C20A115.8 (5)
H9AA—C9A—H9AB109.5C19A—C16A—C13A108.8 (4)
H9AA—C9A—H9AC109.5C19A—C16A—C20A106.0 (6)
H9AB—C9A—H9AC109.5C20A—C16A—C13A109.1 (4)
C3A—C7A—H7AA109.5
N1—C1B'—C13B—C16B172.0 (11)C9—C10—C12—O20.9 (3)
N1—C1B'—C14B—C15B173.9 (11)C1A—N2—C5—C6177.46 (16)
N1—C1A'—C14A—C15A173.6 (8)C1A—N2—C5—C41.3 (3)
N1—C1A'—C13A—C16A176.2 (6)C1A—C5A—C4A—N1'50.5 (2)
N2—C5—C4—C3174.82 (18)C1A—C5A—C4A—C8A165.3 (2)
N2—C1A—C5A—C4A177.00 (17)C1A—C5A—C4A—C9A75.5 (2)
N2—C1A—C2A—C3A175.87 (16)C1A—C2A—C3A—N1'53.1 (2)
C11—C2—C1—O1177.45 (16)C1A—C2A—C3A—C6A73.0 (2)
C11—C2—C1—N12.9 (2)C1A—C2A—C3A—C7A167.90 (19)
C11—C2—C3—C42.0 (3)C1B'—N1—C1—O11.6 (10)
C11—C6—C5—N2174.59 (16)C1B'—N1—C1—C2178.7 (10)
C11—C6—C5—C44.2 (2)C1B'—N1—C12—O22.9 (11)
C11—C6—C7—C80.5 (3)C1B'—N1—C12—C10176.7 (10)
C11—C10—C12—N11.1 (2)C5A—C1A—C2A—C3A60.7 (2)
C11—C10—C12—O2179.29 (17)C2A—C1A—C5A—C4A58.7 (2)
C11—C10—C9—C81.1 (3)C4A—N1'—C3A—C2A48.5 (3)
C2—C11—C6—C51.5 (2)C4A—N1'—C3A—C6A75.3 (3)
C2—C11—C6—C7178.78 (15)C4A—N1'—C3A—C7A166.3 (2)
C2—C11—C10—C120.4 (2)C3A—N1'—C4A—C5A47.5 (3)
C2—C11—C10—C9178.00 (16)C3A—N1'—C4A—C8A164.9 (2)
C2—C3—C4—C50.8 (3)C3A—N1'—C4A—C9A76.9 (3)
C6—C11—C2—C1178.24 (14)C13B—C1B'—C14B—C15B59.1 (17)
C6—C11—C2—C31.6 (2)C13B—C16B—N3B—C15B46.5 (9)
C6—C11—C10—C12179.75 (15)C14B—C1B'—C13B—C16B57.1 (18)
C6—C11—C10—C91.4 (2)C14B—C15B—N3B—C16B49.9 (9)
C6—C5—C4—C33.9 (3)C17B—C15B—C14B—C1B'79.7 (11)
C6—C7—C8—C90.8 (3)C17B—C15B—N3B—C16B77.5 (9)
C1—N1—C12—O2179.84 (17)C18B—C15B—C14B—C1B'166.1 (11)
C1—N1—C12—C100.5 (2)C18B—C15B—N3B—C16B165.3 (7)
C1—N1—C1B'—C13B103.3 (14)C1A'—N1—C1—O13.3 (7)
C1—N1—C1B'—C14B126.8 (12)C1A'—N1—C1—C2176.4 (7)
C1—N1—C1A'—C14A70.1 (13)C1A'—N1—C12—O22.0 (7)
C1—N1—C1A'—C13A58.4 (9)C1A'—N1—C12—C10178.4 (6)
C1—C2—C3—C4177.84 (17)C1A'—C14A—C15A—C18A77.3 (9)
C10—C11—C2—C12.4 (2)C1A'—C14A—C15A—C17A164.8 (9)
C10—C11—C2—C3177.74 (15)C1A'—C14A—C15A—N3A48.6 (9)
C10—C11—C6—C5179.15 (15)C1A'—C13A—C16A—N3A50.7 (7)
C10—C11—C6—C70.6 (2)C1A'—C13A—C16A—C19A168.0 (7)
C10—C9—C8—C70.0 (3)C1A'—C13A—C16A—C20A76.8 (7)
C5—N2—C1A—C5A155.91 (18)C14A—C1A'—C13A—C16A55.0 (12)
C5—N2—C1A—C2A81.9 (2)C14A—C15A—N3A—C16A49.8 (5)
C5—C6—C7—C8179.77 (18)C15A—N3A—C16A—C19A169.7 (4)
C12—N1—C1—O1178.93 (16)C15A—N3A—C16A—C13A51.6 (5)
C12—N1—C1—C21.4 (2)C15A—N3A—C16A—C20A71.9 (6)
C12—N1—C1B'—C13B79.3 (19)C18A—C15A—N3A—C16A73.5 (5)
C12—N1—C1B'—C14B50.7 (15)C17A—C15A—N3A—C16A167.4 (5)
C12—N1—C1A'—C14A112.0 (9)C13A—C1A'—C14A—C15A55.2 (13)
C12—N1—C1A'—C13A119.5 (9)N3B—C16B—C13B—C1B'45.7 (15)
C12—C10—C9—C8179.47 (17)N3B—C15B—C14B—C1B'50.8 (11)
C3—C2—C1—O12.4 (3)C19B—C16B—C13B—C1B'78.6 (15)
C3—C2—C1—N1177.21 (16)C19B—C16B—N3B—C15B75.7 (10)
C7—C6—C5—N25.1 (3)C20B—C16B—C13B—C1B'161.9 (15)
C7—C6—C5—C4176.09 (17)C20B—C16B—N3B—C15B164.5 (8)
C9—C10—C12—N1179.46 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.173.0134 (18)165
C9—H9···O2ii0.932.543.203 (2)128
Symmetry codes: (i) x+3/2, y1/2, z; (ii) x+1, y+1, z+1.
 

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