4-(9-Acridin-9-yl­amino)-2,2,6,6-tetra­methyl­piperidine N-oxide

The title compound, C₂₂H₂₆N₃O, crystallizes in space group P2₁ with two mol­ecules in the asymmetric unit. Intermolecular N—H...O hydrogen bonds play an important role in the formation of polymeric chains running along the crystallographic a axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.120
• Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.42
           From the CIF: _reflns_number_total               4441
           Count of symmetry unique reflns         4464
           Completeness (_total/calc)             99.48%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: PROCESS-AUTO (Version 1.06; Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Version 3.60; Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

(I)

Crystal data

C22H26N3O	F(000) = 748
Mr = 348.46	Dx = 1.232 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 12213 reflections
a = 11.1168 (3) Å	θ = 2.2–27.4°
b = 14.2464 (3) Å	µ = 0.08 mm^−1
c = 11.8709 (3) Å	T = 293 K
β = 92.113 (1)°	Block, orange
V = 1878.77 (8) Å^3	0.4 × 0.3 × 0.18 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	3581 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.039
ω scans	θmax = 27.4°, θmin = 1.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
Tmin = 0.954, Tmax = 0.986	k = −18→18
17974 measured reflections	l = −15→14
4441 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0776P)^2 + 0.0762P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.044	(Δ/σ)max < 0.001
wR(F^2) = 0.120	Δρmax = 0.17 e Å^−3
S = 1.01	Δρmin = −0.17 e Å^−3
4441 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
480 parameters	Extinction coefficient: 0.0046 (13)
1 restraint

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.0020 (2)	0.88357 (19)	0.42369 (19)	0.0357 (5)
H1	0.0672	0.8778	0.3753	0.043*
C2	−0.0102 (3)	0.7976 (2)	0.4976 (2)	0.0404 (6)
H2A	−0.0192	0.7429	0.4493	0.049*
H2B	−0.0826	0.8025	0.5405	0.049*
C3	0.0969 (3)	0.78094 (19)	0.5803 (2)	0.0400 (6)
C4	0.2030 (3)	0.7363 (3)	0.5220 (3)	0.0659 (10)
H4A	0.2664	0.7233	0.5769	0.099*
H4B	0.2319	0.7788	0.4663	0.099*
H4C	0.1774	0.6789	0.4863	0.099*
C5	0.0583 (4)	0.7172 (2)	0.6758 (3)	0.0615 (9)
H5A	−0.0014	0.7486	0.7185	0.092*
H5B	0.1269	0.7028	0.7242	0.092*
H5C	0.0252	0.6601	0.6448	0.092*
C6	0.1288 (3)	0.9642 (2)	0.5765 (2)	0.0435 (7)
C7	0.1186 (4)	1.0376 (2)	0.6697 (3)	0.0703 (11)
H7A	0.1906	1.0369	0.7169	0.105*
H7B	0.0506	1.0234	0.7141	0.105*
H7C	0.1083	1.0987	0.6364	0.105*
C8	0.2427 (3)	0.9806 (3)	0.5098 (3)	0.0770 (12)
H8A	0.2427	0.9387	0.4465	0.115*
H8B	0.3126	0.9691	0.5577	0.115*
H8C	0.2439	1.0443	0.4835	0.115*
C9	0.0147 (3)	0.96796 (19)	0.5004 (2)	0.0417 (6)
H9A	−0.0545	0.9729	0.5474	0.05*
H9B	0.0172	1.0241	0.4544	0.05*
C10	−0.1211 (2)	0.8649 (2)	0.24124 (19)	0.0369 (5)
C11	−0.2085 (2)	0.79840 (19)	0.2048 (2)	0.0374 (6)
C12	−0.2922 (3)	0.7558 (2)	0.2766 (2)	0.0452 (6)
H12	−0.2904	0.7713	0.3527	0.054*
C13	−0.3743 (3)	0.6930 (2)	0.2364 (3)	0.0568 (8)
H13	−0.4286	0.6664	0.285	0.068*
C14	−0.3785 (3)	0.6675 (3)	0.1218 (3)	0.0614 (9)
H14	−0.4358	0.6247	0.095	0.074*
C15	−0.2998 (3)	0.7051 (2)	0.0507 (3)	0.0551 (8)
H15	−0.3029	0.6866	−0.0244	0.066*
C16	−0.2120 (3)	0.77248 (19)	0.0877 (2)	0.0418 (6)
C17	−0.0572 (2)	0.8716 (2)	0.0466 (2)	0.0410 (6)
C18	0.0202 (3)	0.9104 (2)	−0.0344 (2)	0.0506 (7)
H18	0.0151	0.8885	−0.1082	0.061*
C19	0.1011 (3)	0.9788 (3)	−0.0064 (3)	0.0570 (8)
H19	0.1524	1.002	−0.06	0.068*
C20	0.1069 (3)	1.0143 (3)	0.1048 (3)	0.0573 (8)
H20	0.1598	1.0629	0.1231	0.069*
C21	0.0368 (3)	0.9787 (2)	0.1848 (2)	0.0482 (7)
H21	0.0426	1.0032	0.2574	0.058*
C22	−0.0459 (2)	0.9047 (2)	0.1604 (2)	0.0385 (6)
C23	0.5164 (2)	0.8632 (2)	0.83784 (19)	0.0366 (5)
H23	0.5854	0.8509	0.8895	0.044*
C24	0.5386 (3)	0.9510 (2)	0.7696 (2)	0.0403 (6)
H24A	0.5496	1.0035	0.821	0.048*
H24B	0.4674	0.9638	0.7222	0.048*
C25	0.6467 (2)	0.94571 (19)	0.6954 (2)	0.0394 (6)
C26	0.7652 (3)	0.9468 (3)	0.7663 (3)	0.0547 (8)
H26A	0.8312	0.9346	0.7185	0.082*
H26B	0.7627	0.8994	0.8236	0.082*
H26C	0.7757	1.0073	0.8011	0.082*
C27	0.6432 (3)	1.0284 (2)	0.6126 (3)	0.0581 (8)
H27A	0.5698	1.0262	0.5675	0.087*
H27B	0.7107	1.0244	0.5646	0.087*
H27C	0.6471	1.0863	0.6539	0.087*
C28	0.5990 (2)	0.76586 (19)	0.6721 (2)	0.0384 (6)
C29	0.5481 (3)	0.7096 (2)	0.5714 (3)	0.0550 (8)
H29A	0.612	0.6942	0.5224	0.083*
H29B	0.4886	0.7465	0.5309	0.083*
H29C	0.5119	0.6529	0.5978	0.083*
C30	0.7062 (3)	0.7134 (2)	0.7253 (3)	0.0552 (8)
H30A	0.7376	0.7478	0.7894	0.083*
H30B	0.7676	0.707	0.6711	0.083*
H30C	0.681	0.6523	0.749	0.083*
C31	0.4990 (3)	0.7820 (2)	0.7557 (2)	0.0408 (6)
H31A	0.4241	0.792	0.7129	0.049*
H31B	0.4898	0.7249	0.7991	0.049*
C32	0.3934 (2)	0.85502 (19)	1.01506 (19)	0.0369 (6)
C33	0.4621 (2)	0.90111 (19)	1.1014 (2)	0.0391 (6)
C34	0.5545 (3)	0.9666 (2)	1.0809 (2)	0.0495 (7)
H34	0.5723	0.981	1.007	0.059*
C35	0.6177 (3)	1.0089 (2)	1.1667 (3)	0.0538 (8)
H35	0.6786	1.0512	1.151	0.065*
C36	0.5913 (3)	0.9890 (3)	1.2795 (3)	0.0578 (8)
H36	0.636	1.017	1.3381	0.069*
C37	0.5015 (3)	0.9294 (2)	1.3024 (2)	0.0563 (8)
H37	0.4843	0.9181	1.3773	0.068*
C38	0.4321 (3)	0.8833 (2)	1.2162 (2)	0.0445 (7)
C39	0.2780 (3)	0.7836 (2)	1.1643 (2)	0.0440 (6)
C40	0.1814 (3)	0.7246 (2)	1.1942 (3)	0.0531 (8)
H40	0.1626	0.7195	1.2697	0.064*
C41	0.1161 (3)	0.6759 (2)	1.1163 (3)	0.0567 (8)
H41	0.052	0.639	1.1383	0.068*
C42	0.1443 (3)	0.6803 (2)	1.0013 (3)	0.0574 (8)
H42	0.1017	0.6439	0.9484	0.069*
C43	0.2333 (3)	0.7377 (2)	0.9685 (3)	0.0515 (7)
H43	0.25	0.7411	0.8924	0.062*
C44	0.3021 (2)	0.7928 (2)	1.0468 (2)	0.0393 (6)
N1	0.13692 (19)	0.87159 (16)	0.63246 (16)	0.0368 (5)
N2	−0.1135 (2)	0.89488 (19)	0.35319 (17)	0.0444 (6)
H222	−0.1772	0.8804	0.3922	0.039 (7)*
N3	−0.1382 (2)	0.80731 (18)	0.01112 (18)	0.0457 (6)
N4	0.64069 (19)	0.85784 (17)	0.62823 (16)	0.0380 (5)
N5	0.4066 (2)	0.8754 (2)	0.90192 (16)	0.0466 (6)
H555	0.3444	0.8629	0.8578	0.033 (7)*
N6	0.3418 (2)	0.8275 (2)	1.24667 (19)	0.0514 (6)
O1	0.2132 (2)	0.86493 (17)	0.71561 (16)	0.0585 (6)
O2	0.70787 (19)	0.85413 (17)	0.54264 (16)	0.0552 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0300 (12)	0.0476 (15)	0.0292 (10)	0.0018 (11)	−0.0026 (9)	−0.0002 (12)
C2	0.0402 (15)	0.0437 (14)	0.0370 (13)	−0.0052 (12)	−0.0042 (11)	−0.0032 (12)
C3	0.0444 (16)	0.0388 (14)	0.0365 (13)	0.0035 (12)	−0.0033 (11)	−0.0042 (12)
C4	0.058 (2)	0.081 (2)	0.0578 (19)	0.0286 (18)	−0.0097 (16)	−0.0174 (19)
C5	0.089 (3)	0.0465 (16)	0.0481 (17)	−0.0141 (17)	−0.0138 (17)	0.0094 (16)
C6	0.0487 (16)	0.0430 (14)	0.0382 (13)	−0.0139 (13)	−0.0084 (12)	0.0025 (12)
C7	0.103 (3)	0.0468 (18)	0.0587 (19)	−0.0093 (18)	−0.027 (2)	−0.0078 (16)
C8	0.059 (2)	0.107 (3)	0.065 (2)	−0.037 (2)	−0.0042 (18)	0.027 (2)
C9	0.0508 (16)	0.0374 (13)	0.0364 (12)	0.0002 (12)	−0.0041 (11)	0.0034 (11)
C10	0.0362 (13)	0.0435 (13)	0.0306 (11)	0.0114 (12)	−0.0047 (10)	0.0019 (12)
C11	0.0403 (14)	0.0384 (13)	0.0331 (12)	0.0093 (11)	−0.0036 (11)	0.0028 (11)
C12	0.0506 (17)	0.0479 (15)	0.0372 (13)	0.0051 (13)	0.0011 (12)	0.0031 (13)
C13	0.058 (2)	0.0545 (18)	0.0578 (18)	−0.0086 (16)	0.0048 (15)	0.0055 (16)
C14	0.070 (2)	0.0541 (19)	0.0598 (18)	−0.0196 (16)	−0.0057 (17)	0.0017 (16)
C15	0.073 (2)	0.0496 (17)	0.0425 (15)	−0.0082 (16)	−0.0063 (15)	−0.0039 (14)
C16	0.0499 (16)	0.0402 (14)	0.0349 (12)	0.0049 (12)	−0.0053 (12)	0.0002 (12)
C17	0.0432 (15)	0.0460 (14)	0.0336 (12)	0.0077 (13)	−0.0028 (10)	0.0022 (13)
C18	0.0545 (18)	0.0626 (18)	0.0346 (13)	0.0029 (15)	0.0015 (13)	0.0013 (14)
C19	0.0528 (18)	0.071 (2)	0.0473 (16)	−0.0032 (16)	0.0078 (14)	0.0129 (16)
C20	0.0569 (19)	0.0592 (18)	0.0554 (18)	−0.0127 (16)	−0.0049 (15)	0.0087 (17)
C21	0.0563 (18)	0.0482 (16)	0.0399 (13)	−0.0005 (14)	−0.0030 (13)	−0.0022 (13)
C22	0.0410 (15)	0.0419 (13)	0.0322 (11)	0.0060 (11)	−0.0046 (10)	0.0023 (11)
C23	0.0327 (12)	0.0477 (14)	0.0297 (10)	0.0025 (11)	0.0037 (9)	0.0023 (12)
C24	0.0428 (15)	0.0440 (14)	0.0342 (12)	0.0037 (12)	0.0024 (11)	−0.0022 (12)
C25	0.0398 (15)	0.0406 (14)	0.0379 (13)	−0.0043 (12)	0.0015 (11)	0.0041 (12)
C26	0.0478 (17)	0.0617 (19)	0.0540 (17)	−0.0148 (15)	−0.0049 (14)	−0.0044 (16)
C27	0.070 (2)	0.0507 (18)	0.0547 (17)	−0.0028 (16)	0.0119 (16)	0.0136 (15)
C28	0.0371 (15)	0.0420 (14)	0.0362 (12)	−0.0003 (11)	0.0040 (11)	−0.0011 (12)
C29	0.059 (2)	0.0572 (18)	0.0496 (16)	−0.0103 (16)	0.0097 (14)	−0.0179 (15)
C30	0.055 (2)	0.0545 (17)	0.0567 (17)	0.0125 (15)	0.0064 (15)	0.0043 (16)
C31	0.0387 (14)	0.0459 (15)	0.0380 (13)	−0.0057 (12)	0.0069 (11)	−0.0016 (12)
C32	0.0363 (13)	0.0451 (14)	0.0296 (11)	0.0085 (12)	0.0049 (10)	−0.0017 (12)
C33	0.0424 (14)	0.0422 (14)	0.0325 (11)	0.0100 (12)	−0.0005 (10)	−0.0020 (11)
C34	0.0537 (18)	0.0544 (17)	0.0403 (14)	0.0000 (14)	0.0005 (13)	0.0013 (14)
C35	0.0526 (18)	0.0519 (17)	0.0566 (17)	−0.0032 (15)	−0.0012 (14)	−0.0075 (16)
C36	0.060 (2)	0.063 (2)	0.0489 (16)	0.0055 (17)	−0.0106 (15)	−0.0170 (16)
C37	0.069 (2)	0.066 (2)	0.0336 (13)	0.0078 (17)	−0.0030 (14)	−0.0090 (14)
C38	0.0510 (17)	0.0503 (16)	0.0322 (12)	0.0108 (14)	0.0014 (11)	−0.0027 (13)
C39	0.0496 (16)	0.0484 (15)	0.0346 (12)	0.0068 (13)	0.0078 (12)	0.0044 (12)
C40	0.060 (2)	0.0561 (18)	0.0435 (15)	−0.0004 (15)	0.0103 (14)	0.0129 (15)
C41	0.057 (2)	0.0522 (17)	0.0611 (18)	−0.0048 (15)	0.0065 (16)	0.0118 (16)
C42	0.063 (2)	0.0534 (18)	0.0550 (17)	−0.0035 (16)	−0.0017 (16)	−0.0051 (16)
C43	0.0536 (19)	0.0583 (18)	0.0429 (15)	−0.0019 (15)	0.0041 (13)	−0.0038 (14)
C44	0.0419 (15)	0.0442 (14)	0.0318 (11)	0.0089 (12)	0.0031 (11)	−0.0016 (12)
N1	0.0357 (11)	0.0442 (12)	0.0299 (9)	−0.0046 (10)	−0.0055 (8)	−0.0003 (10)
N2	0.0340 (12)	0.0696 (17)	0.0292 (9)	0.0059 (11)	−0.0024 (9)	−0.0033 (11)
N3	0.0544 (15)	0.0516 (14)	0.0307 (10)	−0.0003 (12)	−0.0019 (10)	−0.0039 (11)
N4	0.0330 (11)	0.0488 (12)	0.0324 (10)	−0.0020 (10)	0.0044 (8)	−0.0011 (10)
N5	0.0328 (11)	0.0792 (18)	0.0278 (9)	0.0045 (12)	0.0018 (8)	−0.0012 (12)
N6	0.0592 (16)	0.0634 (16)	0.0318 (11)	0.0000 (13)	0.0046 (11)	0.0020 (11)
O1	0.0596 (13)	0.0678 (14)	0.0460 (10)	−0.0042 (11)	−0.0263 (9)	0.0022 (11)
O2	0.0554 (12)	0.0706 (14)	0.0411 (9)	−0.0051 (11)	0.0227 (9)	−0.0032 (11)

Geometric parameters (Å, º)

C1—N2	1.479 (3)	C23—C31	1.521 (4)
C1—C2	1.511 (4)	C23—H23	0.98
C1—C9	1.516 (4)	C24—C25	1.518 (4)
C1—H1	0.98	C24—H24A	0.97
C2—C3	1.533 (4)	C24—H24B	0.97
C2—H2A	0.97	C25—N4	1.485 (4)
C2—H2B	0.97	C25—C27	1.533 (4)
C3—N1	1.493 (3)	C25—C26	1.537 (4)
C3—C5	1.526 (4)	C26—H26A	0.96
C3—C4	1.528 (4)	C26—H26B	0.96
C4—H4A	0.96	C26—H26C	0.96
C4—H4B	0.96	C27—H27A	0.96
C4—H4C	0.96	C27—H27B	0.96
C5—H5A	0.96	C27—H27C	0.96
C5—H5B	0.96	C28—N4	1.490 (4)
C5—H5C	0.96	C28—C30	1.524 (4)
C6—N1	1.479 (4)	C28—C29	1.530 (4)
C6—C7	1.529 (4)	C28—C31	1.535 (4)
C6—C9	1.530 (4)	C29—H29A	0.96
C6—C8	1.536 (5)	C29—H29B	0.96
C7—H7A	0.96	C29—H29C	0.96
C7—H7B	0.96	C30—H30A	0.96
C7—H7C	0.96	C30—H30B	0.96
C8—H8A	0.96	C30—H30C	0.96
C8—H8B	0.96	C31—H31A	0.97
C8—H8C	0.96	C31—H31B	0.97
C9—H9A	0.97	C32—N5	1.387 (3)
C9—H9B	0.97	C32—C44	1.409 (4)
C10—N2	1.395 (3)	C32—C33	1.417 (4)
C10—C11	1.414 (4)	C33—C34	1.415 (4)
C10—C22	1.414 (4)	C33—C38	1.438 (3)
C11—C12	1.421 (4)	C34—C35	1.357 (4)
C11—C16	1.437 (4)	C34—H34	0.93
C12—C13	1.352 (4)	C35—C36	1.411 (5)
C12—H12	0.93	C35—H35	0.93
C13—C14	1.407 (5)	C36—C37	1.346 (5)
C13—H13	0.93	C36—H36	0.93
C14—C15	1.348 (5)	C37—C38	1.419 (4)
C14—H14	0.93	C37—H37	0.93
C15—C16	1.427 (4)	C38—N6	1.341 (4)
C15—H15	0.93	C39—N6	1.341 (4)
C16—N3	1.342 (4)	C39—C40	1.419 (4)
C17—N3	1.341 (4)	C39—C44	1.436 (4)
C17—C18	1.425 (4)	C40—C41	1.348 (5)
C17—C22	1.432 (3)	C40—H40	0.93
C18—C19	1.359 (5)	C41—C42	1.412 (5)
C18—H18	0.93	C41—H41	0.93
C19—C20	1.413 (5)	C42—C43	1.352 (5)
C19—H19	0.93	C42—H42	0.93
C20—C21	1.349 (4)	C43—C44	1.418 (4)
C20—H20	0.93	C43—H43	0.93
C21—C22	1.422 (4)	N1—O1	1.281 (3)
C21—H21	0.93	N2—H222	0.885
C23—N5	1.472 (3)	N4—O2	1.284 (3)
C23—C24	1.515 (4)	N5—H555	0.871
N2—C1—C2	110.5 (2)	C23—C24—H24A	108.6
N2—C1—C9	109.6 (2)	C25—C24—H24A	108.6
C2—C1—C9	107.6 (2)	C23—C24—H24B	108.6
N2—C1—H1	109.7	C25—C24—H24B	108.6
C2—C1—H1	109.7	H24A—C24—H24B	107.6
C9—C1—H1	109.7	N4—C25—C24	109.4 (2)
C1—C2—C3	115.8 (2)	N4—C25—C27	107.7 (2)
C1—C2—H2A	108.3	C24—C25—C27	109.4 (2)
C3—C2—H2A	108.3	N4—C25—C26	108.9 (2)
C1—C2—H2B	108.3	C24—C25—C26	111.3 (2)
C3—C2—H2B	108.3	C27—C25—C26	110.1 (3)
H2A—C2—H2B	107.4	C25—C26—H26A	109.5
N1—C3—C5	107.1 (2)	C25—C26—H26B	109.5
N1—C3—C4	108.9 (3)	H26A—C26—H26B	109.5
C5—C3—C4	109.3 (3)	C25—C26—H26C	109.5
N1—C3—C2	110.1 (2)	H26A—C26—H26C	109.5
C5—C3—C2	109.6 (2)	H26B—C26—H26C	109.5
C4—C3—C2	111.7 (2)	C25—C27—H27A	109.5
C3—C4—H4A	109.5	C25—C27—H27B	109.5
C3—C4—H4B	109.5	H27A—C27—H27B	109.5
H4A—C4—H4B	109.5	C25—C27—H27C	109.5
C3—C4—H4C	109.5	H27A—C27—H27C	109.5
H4A—C4—H4C	109.5	H27B—C27—H27C	109.5
H4B—C4—H4C	109.5	N4—C28—C30	109.1 (2)
C3—C5—H5A	109.5	N4—C28—C29	107.3 (2)
C3—C5—H5B	109.5	C30—C28—C29	109.1 (3)
H5A—C5—H5B	109.5	N4—C28—C31	109.7 (2)
C3—C5—H5C	109.5	C30—C28—C31	112.3 (2)
H5A—C5—H5C	109.5	C29—C28—C31	109.1 (2)
H5B—C5—H5C	109.5	C28—C29—H29A	109.5
N1—C6—C7	106.9 (2)	C28—C29—H29B	109.5
N1—C6—C9	109.4 (2)	H29A—C29—H29B	109.5
C7—C6—C9	108.8 (3)	C28—C29—H29C	109.5
N1—C6—C8	109.2 (3)	H29A—C29—H29C	109.5
C7—C6—C8	110.7 (3)	H29B—C29—H29C	109.5
C9—C6—C8	111.8 (2)	C28—C30—H30A	109.5
C6—C7—H7A	109.5	C28—C30—H30B	109.5
C6—C7—H7B	109.5	H30A—C30—H30B	109.5
H7A—C7—H7B	109.5	C28—C30—H30C	109.5
C6—C7—H7C	109.5	H30A—C30—H30C	109.5
H7A—C7—H7C	109.5	H30B—C30—H30C	109.5
H7B—C7—H7C	109.5	C23—C31—C28	116.7 (2)
C6—C8—H8A	109.5	C23—C31—H31A	108.1
C6—C8—H8B	109.5	C28—C31—H31A	108.1
H8A—C8—H8B	109.5	C23—C31—H31B	108.1
C6—C8—H8C	109.5	C28—C31—H31B	108.1
H8A—C8—H8C	109.5	H31A—C31—H31B	107.3
H8B—C8—H8C	109.5	N5—C32—C44	119.5 (2)
C1—C9—C6	114.1 (2)	N5—C32—C33	122.0 (3)
C1—C9—H9A	108.7	C44—C32—C33	118.2 (2)
C6—C9—H9A	108.7	C34—C33—C32	123.9 (2)
C1—C9—H9B	108.7	C34—C33—C38	118.3 (2)
C6—C9—H9B	108.7	C32—C33—C38	117.8 (2)
H9A—C9—H9B	107.6	C35—C34—C33	121.6 (3)
N2—C10—C11	120.9 (2)	C35—C34—H34	119.2
N2—C10—C22	120.5 (3)	C33—C34—H34	119.2
C11—C10—C22	118.5 (2)	C34—C35—C36	120.2 (3)
C10—C11—C12	124.1 (2)	C34—C35—H35	119.9
C10—C11—C16	117.5 (3)	C36—C35—H35	119.9
C12—C11—C16	118.4 (3)	C37—C36—C35	120.0 (3)
C13—C12—C11	121.3 (3)	C37—C36—H36	120
C13—C12—H12	119.3	C35—C36—H36	120
C11—C12—H12	119.3	C36—C37—C38	122.3 (3)
C12—C13—C14	120.6 (3)	C36—C37—H37	118.9
C12—C13—H13	119.7	C38—C37—H37	118.9
C14—C13—H13	119.7	N6—C38—C37	118.2 (2)
C15—C14—C13	120.2 (3)	N6—C38—C33	124.2 (2)
C15—C14—H14	119.9	C37—C38—C33	117.6 (3)
C13—C14—H14	119.9	N6—C39—C40	118.6 (2)
C14—C15—C16	121.8 (3)	N6—C39—C44	123.6 (3)
C14—C15—H15	119.1	C40—C39—C44	117.8 (3)
C16—C15—H15	119.1	C41—C40—C39	121.8 (3)
N3—C16—C15	118.0 (2)	C41—C40—H40	119.1
N3—C16—C11	124.4 (3)	C39—C40—H40	119.1
C15—C16—C11	117.6 (3)	C40—C41—C42	120.5 (3)
N3—C17—C18	117.9 (2)	C40—C41—H41	119.7
N3—C17—C22	123.7 (3)	C42—C41—H41	119.7
C18—C17—C22	118.4 (3)	C43—C42—C41	119.7 (3)
C19—C18—C17	121.6 (3)	C43—C42—H42	120.1
C19—C18—H18	119.2	C41—C42—H42	120.1
C17—C18—H18	119.2	C42—C43—C44	121.9 (3)
C18—C19—C20	119.5 (3)	C42—C43—H43	119
C18—C19—H19	120.3	C44—C43—H43	119
C20—C19—H19	120.3	C32—C44—C43	123.3 (2)
C21—C20—C19	121.1 (3)	C32—C44—C39	118.6 (2)
C21—C20—H20	119.5	C43—C44—C39	118.1 (3)
C19—C20—H20	119.5	O1—N1—C6	116.1 (2)
C20—C21—C22	121.4 (3)	O1—N1—C3	115.8 (2)
C20—C21—H21	119.3	C6—N1—C3	124.97 (18)
C22—C21—H21	119.3	C10—N2—C1	121.7 (2)
C10—C22—C21	123.6 (2)	C10—N2—H222	113.9
C10—C22—C17	118.4 (3)	C1—N2—H222	110.4
C21—C22—C17	118.0 (3)	C17—N3—C16	117.4 (2)
N5—C23—C24	109.5 (2)	O2—N4—C25	116.3 (2)
N5—C23—C31	109.4 (2)	O2—N4—C28	116.0 (2)
C24—C23—C31	107.76 (19)	C25—N4—C28	124.20 (19)
N5—C23—H23	110.1	C32—N5—C23	126.5 (2)
C24—C23—H23	110.1	C32—N5—H555	115.5
C31—C23—H23	110.1	C23—N5—H555	108.7
C23—C24—C25	114.6 (2)	C38—N6—C39	117.5 (2)
N2—C1—C2—C3	−176.5 (2)	C36—C37—C38—C33	0.9 (5)
C9—C1—C2—C3	−56.9 (3)	C34—C33—C38—N6	175.7 (3)
C1—C2—C3—N1	41.5 (3)	C32—C33—C38—N6	−1.5 (4)
C1—C2—C3—C5	159.0 (2)	C34—C33—C38—C37	−3.0 (4)
C1—C2—C3—C4	−79.7 (3)	C32—C33—C38—C37	179.8 (3)
N2—C1—C9—C6	−179.3 (2)	N6—C39—C40—C41	−177.7 (3)
C2—C1—C9—C6	60.6 (3)	C44—C39—C40—C41	2.3 (5)
N1—C6—C9—C1	−48.6 (3)	C39—C40—C41—C42	1.6 (5)
C7—C6—C9—C1	−165.0 (2)	C40—C41—C42—C43	−3.5 (5)
C8—C6—C9—C1	72.5 (3)	C41—C42—C43—C44	1.4 (5)
N2—C10—C11—C12	−1.3 (4)	N5—C32—C44—C43	10.1 (4)
C22—C10—C11—C12	−177.8 (2)	C33—C32—C44—C43	−175.3 (3)
N2—C10—C11—C16	178.9 (2)	N5—C32—C44—C39	−170.7 (3)
C22—C10—C11—C16	2.5 (4)	C33—C32—C44—C39	3.8 (4)
C10—C11—C12—C13	179.5 (3)	C42—C43—C44—C32	−178.3 (3)
C16—C11—C12—C13	−0.7 (4)	C42—C43—C44—C39	2.5 (5)
C11—C12—C13—C14	0.5 (5)	N6—C39—C44—C32	−3.4 (4)
C12—C13—C14—C15	0.5 (6)	C40—C39—C44—C32	176.6 (3)
C13—C14—C15—C16	−1.2 (6)	N6—C39—C44—C43	175.8 (3)
C14—C15—C16—N3	−179.1 (3)	C40—C39—C44—C43	−4.2 (4)
C14—C15—C16—C11	1.0 (5)	C7—C6—N1—O1	−48.4 (3)
C10—C11—C16—N3	−0.1 (4)	C9—C6—N1—O1	−166.0 (2)
C12—C11—C16—N3	−179.9 (3)	C8—C6—N1—O1	71.3 (3)
C10—C11—C16—C15	179.8 (3)	C7—C6—N1—C3	152.6 (3)
C12—C11—C16—C15	0.0 (4)	C9—C6—N1—C3	35.1 (4)
N3—C17—C18—C19	177.1 (3)	C8—C6—N1—C3	−87.6 (3)
C22—C17—C18—C19	−1.5 (4)	C5—C3—N1—O1	50.5 (3)
C17—C18—C19—C20	−1.8 (5)	C4—C3—N1—O1	−67.7 (3)
C18—C19—C20—C21	2.8 (5)	C2—C3—N1—O1	169.5 (2)
C19—C20—C21—C22	−0.3 (5)	C5—C3—N1—C6	−150.5 (3)
N2—C10—C22—C21	−2.9 (4)	C4—C3—N1—C6	91.3 (3)
C11—C10—C22—C21	173.5 (3)	C2—C3—N1—C6	−31.5 (3)
N2—C10—C22—C17	−180.0 (2)	C11—C10—N2—C1	121.6 (3)
C11—C10—C22—C17	−3.6 (4)	C22—C10—N2—C1	−62.1 (4)
C20—C21—C22—C10	179.9 (3)	C2—C1—N2—C10	−98.5 (3)
C20—C21—C22—C17	−3.0 (4)	C9—C1—N2—C10	143.0 (3)
N3—C17—C22—C10	2.5 (4)	C18—C17—N3—C16	−178.8 (3)
C18—C17—C22—C10	−178.9 (3)	C22—C17—N3—C16	−0.2 (4)
N3—C17—C22—C21	−174.7 (3)	C15—C16—N3—C17	179.1 (3)
C18—C17—C22—C21	3.9 (4)	C11—C16—N3—C17	−1.0 (4)
N5—C23—C24—C25	−177.4 (2)	C24—C25—N4—O2	163.3 (2)
C31—C23—C24—C25	−58.6 (3)	C27—C25—N4—O2	44.5 (3)
C23—C24—C25—N4	49.9 (3)	C26—C25—N4—O2	−74.8 (3)
C23—C24—C25—C27	167.6 (2)	C24—C25—N4—C28	−38.7 (3)
C23—C24—C25—C26	−70.5 (3)	C27—C25—N4—C28	−157.4 (3)
N5—C23—C31—C28	173.3 (2)	C26—C25—N4—C28	83.2 (3)
C24—C23—C31—C28	54.4 (3)	C30—C28—N4—O2	69.0 (3)
N4—C28—C31—C23	−41.4 (3)	C29—C28—N4—O2	−49.1 (3)
C30—C28—C31—C23	80.1 (3)	C31—C28—N4—O2	−167.6 (2)
C29—C28—C31—C23	−158.8 (2)	C30—C28—N4—C25	−89.1 (3)
N5—C32—C33—C34	−4.2 (4)	C29—C28—N4—C25	152.8 (2)
C44—C32—C33—C34	−178.6 (3)	C31—C28—N4—C25	34.3 (3)
N5—C32—C33—C38	172.8 (2)	C44—C32—N5—C23	−123.9 (3)
C44—C32—C33—C38	−1.6 (4)	C33—C32—N5—C23	61.8 (4)
C32—C33—C34—C35	180.0 (3)	C24—C23—N5—C32	−133.0 (3)
C38—C33—C34—C35	2.9 (4)	C31—C23—N5—C32	109.1 (3)
C33—C34—C35—C36	−0.7 (5)	C37—C38—N6—C39	−179.2 (3)
C34—C35—C36—C37	−1.5 (5)	C33—C38—N6—C39	2.1 (4)
C35—C36—C37—C38	1.3 (5)	C40—C39—N6—C38	−179.6 (3)
C36—C37—C38—N6	−177.8 (3)	C44—C39—N6—C38	0.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H555···O1	0.87	2.19	3.031 (3)	162
N2—H222···O2^i	0.89	2.27	3.109 (3)	160

Symmetry code: (i) x−1, y, z.