10-Methyl-8,9,10,11,11a,12-hexa­hydro-5H,7H-iso­quinolino[3,2-g][1,3,5]triazepine-7,11-dione

In the title compound, C₁₃H₁₅N₃O₂, the triazepane ring adopts a twist–boat conformation and the piperidine ring adopts a boat conformation. The mol­ecular packing is stabilized by N—H...O, C—H...O, C—H...π and van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.117
• Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.78 Ratio

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           27.87
           From the CIF: _reflns_number_total               3144
           Count of symmetry unique reflns         3174
           Completeness (_total/calc)             99.05%
           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
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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: COLLECT (Nonius, 1998); cell refinement: COLLECT; data reduction: HKL (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); 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 (Farrugia, 1999) and PLATON (Spek, 2003).

10-methyl-8,9,10,11,11a,12-hexahydro5H,7H-isoquinolino[3,2-g][1,3,5]triazepine- 7,11-dione

Crystal data

C13H15N3O2	F(000) = 1040
Mr = 245.28	Dx = 1.374 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 14659 reflections
a = 12.1766 (2) Å	θ = 1.0–27.9°
b = 12.5948 (2) Å	µ = 0.10 mm^−1
c = 15.4676 (3) Å	T = 293 K
V = 2372.14 (7) Å^3	Prism, colourless
Z = 8	0.6 × 0.6 × 0.5 mm

Data collection

Bruker Nonius KappaCCD area-detector diffractometer	2706 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.04
Graphite monochromator	θmax = 27.9°, θmin = 3.1°
oscillation scans	h = −16→16
14659 measured reflections	k = −16→16
3144 independent reflections	l = −20→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 0.3973P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.117	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.17 e Å^−3
3144 reflections	Δρmin = −0.17 e Å^−3
326 parameters

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
C1A	0.46720 (19)	0.57392 (18)	0.96834 (15)	0.0414 (5)
O1A	0.54408 (14)	0.52171 (14)	0.99769 (13)	0.0557 (5)
N1A	0.48924 (17)	0.66838 (16)	0.92842 (14)	0.0485 (5)
H1A	0.5564	0.6893	0.9301	0.058*
C2A	0.4137 (2)	0.73675 (19)	0.88398 (15)	0.0466 (5)
H2A	0.3765	0.6966	0.8392	0.056*
H3A	0.4543	0.7936	0.8562	0.056*
N2A	0.33211 (17)	0.78249 (15)	0.94217 (14)	0.0463 (5)
C3A	0.3471 (3)	0.89006 (19)	0.9757 (2)	0.0580 (7)
H4A	0.3947	0.9291	0.9378	0.087*
H6A	0.3794	0.8867	1.0323	0.087*
H5A	0.2772	0.925	0.9791	0.087*
C4A	0.26650 (19)	0.71595 (18)	0.98626 (15)	0.0422 (5)
O2A	0.21372 (15)	0.74415 (14)	1.04956 (13)	0.0579 (5)
C5A	0.26097 (19)	0.60109 (17)	0.95172 (16)	0.0406 (5)
H7A	0.2556	0.6028	0.8885	0.049*
C6A	0.1579 (2)	0.5500 (2)	0.9884 (2)	0.0547 (6)
H9A	0.1564	0.5605	1.0505	0.066*
H8A	0.0939	0.5848	0.9641	0.066*
C7A	0.1519 (2)	0.4332 (2)	0.96934 (17)	0.0515 (6)
C8A	0.0566 (3)	0.3815 (3)	0.9438 (2)	0.0681 (8)
H10A	−0.0077	0.4201	0.9356	0.082*
C9A	0.0568 (3)	0.2736 (3)	0.9305 (2)	0.0762 (10)
H11A	−0.0069	0.2395	0.9122	0.091*
C10A	0.1507 (4)	0.2163 (2)	0.9442 (2)	0.0789 (11)
H12A	0.1498	0.1429	0.9373	0.095*
C11A	0.2472 (3)	0.2668 (2)	0.96835 (19)	0.0682 (8)
H13A	0.3113	0.2277	0.9761	0.082*
C12A	0.2476 (2)	0.37596 (19)	0.98083 (16)	0.0528 (6)
C13A	0.3475 (3)	0.4333 (2)	1.0139 (2)	0.0575 (7)
H15A	0.3427	0.439	1.0763	0.069*
H14A	0.4123	0.3916	1.0003	0.069*
N3A	0.36041 (16)	0.54067 (15)	0.97678 (14)	0.0432 (5)
C21	0.18065 (19)	0.76712 (17)	0.73394 (16)	0.0421 (5)
O1B	0.22386 (16)	0.69371 (14)	0.69450 (14)	0.0618 (5)
N1B	0.09730 (17)	0.74571 (15)	0.78934 (14)	0.0494 (5)
H1B	0.0819	0.6795	0.7954	0.059*
C2B	0.0306 (2)	0.8170 (2)	0.83959 (18)	0.0506 (6)
H3B	0.0751	0.8469	0.8856	0.061*
H2B	−0.0284	0.777	0.8662	0.061*
N2B	−0.01659 (17)	0.90356 (17)	0.78909 (15)	0.0507 (5)
C3B	−0.1350 (2)	0.9051 (3)	0.7735 (2)	0.0653 (8)
H5	−0.1729	0.8844	0.8252	0.098*
H4B	−0.1526	0.8564	0.7278	0.098*
H6B	−0.1572	0.9754	0.7572	0.098*
C4B	0.0485 (2)	0.97624 (18)	0.75314 (17)	0.0453 (5)
O2B	0.01518 (16)	1.04940 (14)	0.70720 (15)	0.0646 (5)
C5B	0.17117 (19)	0.96219 (17)	0.77102 (17)	0.0442 (5)
H7B	0.1815	0.9486	0.8329	0.053*
C6B	0.2343 (2)	1.0628 (2)	0.7465 (2)	0.0566 (7)
H8B	0.2167	1.0827	0.6875	0.068*
H9B	0.2128	1.1206	0.7842	0.068*
C7B	0.3546 (2)	1.0435 (2)	0.75446 (18)	0.0576 (7)
C8B	0.4254 (3)	1.1081 (4)	0.8013 (2)	0.0907 (12)
H10B	0.3984	1.1679	0.8296	0.109*
C9B	0.5332 (4)	1.0841 (5)	0.8059 (3)	0.116 (2)
H11B	0.58	1.127	0.8381	0.139*
C10B	0.5743 (3)	0.9979 (5)	0.7639 (4)	0.117 (2)
H12B	0.6491	0.9834	0.7667	0.14*
C11B	0.5040 (3)	0.9295 (3)	0.7157 (3)	0.0919 (13)
H13B	0.5318	0.8701	0.6875	0.11*
C12B	0.3929 (2)	0.9539 (2)	0.71202 (19)	0.0573 (7)
C13B	0.3082 (2)	0.8891 (2)	0.6646 (2)	0.0565 (7)
H15B	0.2846	0.9266	0.6131	0.068*
H14B	0.3397	0.8217	0.6471	0.068*
N3B	0.21335 (16)	0.87046 (15)	0.72184 (15)	0.0453 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0419 (12)	0.0410 (11)	0.0412 (11)	0.0038 (10)	−0.0009 (9)	−0.0050 (9)
O1A	0.0481 (10)	0.0500 (9)	0.0691 (12)	0.0125 (8)	−0.0119 (9)	−0.0045 (9)
N1A	0.0358 (10)	0.0493 (11)	0.0604 (13)	−0.0020 (9)	0.0016 (9)	0.0064 (10)
C2A	0.0478 (13)	0.0472 (12)	0.0449 (12)	−0.0043 (11)	0.0027 (10)	0.0081 (11)
N2A	0.0465 (11)	0.0377 (9)	0.0547 (11)	0.0007 (9)	−0.0002 (9)	0.0023 (9)
C3A	0.0652 (17)	0.0374 (12)	0.0716 (17)	−0.0019 (11)	−0.0058 (15)	−0.0006 (12)
C4A	0.0358 (11)	0.0420 (11)	0.0487 (12)	0.0067 (10)	−0.0012 (10)	0.0040 (10)
O2A	0.0554 (11)	0.0519 (10)	0.0663 (11)	0.0086 (9)	0.0151 (9)	−0.0052 (9)
C5A	0.0381 (11)	0.0391 (10)	0.0447 (11)	0.0030 (9)	−0.0008 (10)	0.0029 (9)
C6A	0.0448 (13)	0.0502 (14)	0.0691 (17)	−0.0056 (11)	0.0069 (12)	0.0014 (13)
C7A	0.0561 (15)	0.0504 (13)	0.0482 (13)	−0.0134 (12)	0.0049 (12)	0.0050 (11)
C8A	0.0667 (19)	0.0711 (18)	0.0664 (17)	−0.0263 (16)	−0.0006 (15)	0.0112 (16)
C9A	0.097 (3)	0.073 (2)	0.0580 (17)	−0.043 (2)	−0.0051 (17)	0.0105 (16)
C10A	0.132 (3)	0.0470 (15)	0.0578 (17)	−0.034 (2)	0.009 (2)	−0.0017 (14)
C11A	0.098 (2)	0.0443 (13)	0.0623 (17)	−0.0061 (15)	0.0011 (18)	0.0048 (13)
C12A	0.0719 (18)	0.0407 (11)	0.0459 (12)	−0.0118 (12)	0.0026 (13)	0.0047 (10)
C13A	0.0663 (17)	0.0385 (12)	0.0676 (16)	−0.0021 (12)	−0.0093 (14)	0.0138 (12)
N3A	0.0388 (10)	0.0374 (9)	0.0533 (11)	0.0020 (8)	−0.0011 (9)	0.0044 (9)
C21	0.0389 (11)	0.0353 (10)	0.0521 (13)	0.0028 (9)	−0.0065 (10)	−0.0049 (10)
O1B	0.0618 (11)	0.0417 (9)	0.0818 (13)	0.0054 (8)	0.0089 (10)	−0.0146 (9)
N1B	0.0501 (11)	0.0342 (9)	0.0638 (12)	−0.0047 (8)	0.0052 (10)	−0.0012 (9)
C2B	0.0509 (14)	0.0493 (12)	0.0517 (13)	−0.0021 (11)	0.0070 (12)	0.0011 (11)
N2B	0.0416 (11)	0.0512 (11)	0.0593 (13)	0.0065 (9)	0.0050 (10)	0.0004 (10)
C3B	0.0385 (13)	0.081 (2)	0.0763 (19)	0.0026 (13)	0.0091 (13)	−0.0031 (17)
C4B	0.0443 (12)	0.0383 (10)	0.0531 (13)	0.0082 (10)	0.0036 (11)	−0.0050 (10)
O2B	0.0597 (11)	0.0479 (10)	0.0864 (14)	0.0177 (9)	0.0013 (11)	0.0092 (10)
C5B	0.0437 (12)	0.0367 (11)	0.0523 (13)	0.0012 (10)	−0.0004 (10)	−0.0039 (10)
C6B	0.0621 (16)	0.0409 (12)	0.0667 (16)	−0.0072 (12)	0.0063 (14)	−0.0061 (12)
C7B	0.0580 (15)	0.0623 (16)	0.0524 (14)	−0.0186 (14)	−0.0001 (12)	0.0101 (13)
C8B	0.092 (3)	0.115 (3)	0.0648 (19)	−0.063 (2)	−0.0073 (18)	0.012 (2)
C9B	0.085 (3)	0.174 (5)	0.090 (3)	−0.069 (3)	−0.028 (2)	0.057 (3)
C10B	0.0397 (17)	0.183 (5)	0.128 (4)	−0.029 (3)	−0.017 (2)	0.102 (4)
C11B	0.0502 (17)	0.107 (3)	0.119 (3)	0.0055 (19)	0.017 (2)	0.066 (3)
C12B	0.0422 (13)	0.0674 (16)	0.0623 (16)	−0.0056 (12)	0.0047 (12)	0.0295 (14)
C13B	0.0548 (15)	0.0523 (14)	0.0625 (16)	0.0014 (12)	0.0167 (13)	0.0014 (13)
N3B	0.0408 (10)	0.0369 (9)	0.0581 (12)	0.0010 (8)	0.0061 (9)	−0.0038 (9)

Geometric parameters (Å, º)

C1A—O1A	1.231 (3)	C21—O1B	1.226 (3)
C1A—N1A	1.367 (3)	C21—N1B	1.355 (3)
C1A—N3A	1.372 (3)	C21—N3B	1.374 (3)
N1A—C2A	1.435 (3)	N1B—C2B	1.439 (3)
N1A—H1A	0.86	N1B—H1B	0.86
C2A—N2A	1.459 (3)	C2B—N2B	1.459 (3)
C2A—H2A	0.97	C2B—H3B	0.97
C2A—H3A	0.97	C2B—H2B	0.97
N2A—C4A	1.344 (3)	N2B—C4B	1.332 (3)
N2A—C3A	1.462 (3)	N2B—C3B	1.462 (3)
C3A—H4A	0.96	C3B—H5	0.96
C3A—H6A	0.96	C3B—H4B	0.96
C3A—H5A	0.96	C3B—H6B	0.96
C4A—O2A	1.224 (3)	C4B—O2B	1.232 (3)
C4A—C5A	1.544 (3)	C4B—C5B	1.529 (3)
C5A—N3A	1.482 (3)	C5B—N3B	1.476 (3)
C5A—C6A	1.520 (3)	C5B—C6B	1.529 (3)
C5A—H7A	0.98	C5B—H7B	0.98
C6A—C7A	1.502 (4)	C6B—C7B	1.490 (4)
C6A—H9A	0.97	C6B—H8B	0.97
C6A—H8A	0.97	C6B—H9B	0.97
C7A—C12A	1.381 (4)	C7B—C12B	1.386 (4)
C7A—C8A	1.388 (4)	C7B—C8B	1.389 (4)
C8A—C9A	1.374 (5)	C8B—C9B	1.349 (7)
C8A—H10A	0.93	C8B—H10B	0.93
C9A—C10A	1.369 (6)	C9B—C10B	1.361 (7)
C9A—H11A	0.93	C9B—H11B	0.93
C10A—C11A	1.388 (5)	C10B—C11B	1.425 (7)
C10A—H12A	0.93	C10B—H12B	0.93
C11A—C12A	1.389 (4)	C11B—C12B	1.389 (4)
C11A—H13A	0.93	C11B—H13B	0.93
C12A—C13A	1.504 (4)	C12B—C13B	1.506 (4)
C13A—N3A	1.478 (3)	C13B—N3B	1.474 (3)
C13A—H15A	0.97	C13B—H15B	0.97
C13A—H14A	0.97	C13B—H14B	0.97
O1A—C1A—N1A	118.8 (2)	O1B—C21—N1B	119.1 (2)
O1A—C1A—N3A	121.5 (2)	O1B—C21—N3B	121.5 (2)
N1A—C1A—N3A	119.6 (2)	N1B—C21—N3B	119.4 (2)
C1A—N1A—C2A	127.8 (2)	C21—N1B—C2B	129.8 (2)
C1A—N1A—H1A	116.1	C21—N1B—H1B	115.1
C2A—N1A—H1A	116.1	C2B—N1B—H1B	115.1
N1A—C2A—N2A	112.20 (19)	N1B—C2B—N2B	113.5 (2)
N1A—C2A—H2A	109.2	N1B—C2B—H3B	108.9
N2A—C2A—H2A	109.2	N2B—C2B—H3B	108.9
N1A—C2A—H3A	109.2	N1B—C2B—H2B	108.9
N2A—C2A—H3A	109.2	N2B—C2B—H2B	108.9
H2A—C2A—H3A	107.9	H3B—C2B—H2B	107.7
C4A—N2A—C2A	118.14 (19)	C4B—N2B—C2B	120.1 (2)
C4A—N2A—C3A	118.2 (2)	C4B—N2B—C3B	120.6 (2)
C2A—N2A—C3A	120.0 (2)	C2B—N2B—C3B	119.1 (2)
N2A—C3A—H4A	109.5	N2B—C3B—H5	109.5
N2A—C3A—H6A	109.5	N2B—C3B—H4B	109.5
H4A—C3A—H6A	109.5	H5—C3B—H4B	109.5
N2A—C3A—H5A	109.5	N2B—C3B—H6B	109.5
H4A—C3A—H5A	109.5	H5—C3B—H6B	109.5
H6A—C3A—H5A	109.5	H4B—C3B—H6B	109.5
O2A—C4A—N2A	122.5 (2)	O2B—C4B—N2B	124.0 (2)
O2A—C4A—C5A	121.7 (2)	O2B—C4B—C5B	120.8 (2)
N2A—C4A—C5A	115.8 (2)	N2B—C4B—C5B	115.2 (2)
N3A—C5A—C6A	111.06 (19)	N3B—C5B—C4B	109.7 (2)
N3A—C5A—C4A	110.80 (19)	N3B—C5B—C6B	110.2 (2)
C6A—C5A—C4A	107.7 (2)	C4B—C5B—C6B	110.5 (2)
N3A—C5A—H7A	109.1	N3B—C5B—H7B	108.8
C6A—C5A—H7A	109.1	C4B—C5B—H7B	108.8
C4A—C5A—H7A	109.1	C6B—C5B—H7B	108.8
C7A—C6A—C5A	112.4 (2)	C7B—C6B—C5B	109.8 (2)
C7A—C6A—H9A	109.1	C7B—C6B—H8B	109.7
C5A—C6A—H9A	109.1	C5B—C6B—H8B	109.7
C7A—C6A—H8A	109.1	C7B—C6B—H9B	109.7
C5A—C6A—H8A	109.1	C5B—C6B—H9B	109.7
H9A—C6A—H8A	107.8	H8B—C6B—H9B	108.2
C12A—C7A—C8A	119.8 (3)	C12B—C7B—C8B	121.0 (3)
C12A—C7A—C6A	116.4 (2)	C12B—C7B—C6B	115.1 (2)
C8A—C7A—C6A	123.8 (3)	C8B—C7B—C6B	123.9 (3)
C9A—C8A—C7A	120.3 (4)	C9B—C8B—C7B	120.0 (5)
C9A—C8A—H10A	119.8	C9B—C8B—H10B	120
C7A—C8A—H10A	119.8	C7B—C8B—H10B	120
C10A—C9A—C8A	119.9 (3)	C8B—C9B—C10B	120.8 (5)
C10A—C9A—H11A	120	C8B—C9B—H11B	119.6
C8A—C9A—H11A	120	C10B—C9B—H11B	119.6
C9A—C10A—C11A	120.5 (3)	C9B—C10B—C11B	120.8 (4)
C9A—C10A—H12A	119.7	C9B—C10B—H12B	119.6
C11A—C10A—H12A	119.7	C11B—C10B—H12B	119.6
C10A—C11A—C12A	119.6 (3)	C12B—C11B—C10B	118.2 (4)
C10A—C11A—H13A	120.2	C12B—C11B—H13B	120.9
C12A—C11A—H13A	120.2	C10B—C11B—H13B	120.9
C7A—C12A—C11A	119.7 (3)	C7B—C12B—C11B	119.3 (3)
C7A—C12A—C13A	118.4 (2)	C7B—C12B—C13B	116.2 (2)
C11A—C12A—C13A	121.7 (3)	C11B—C12B—C13B	124.5 (3)
N3A—C13A—C12A	113.2 (2)	N3B—C13B—C12B	109.3 (2)
N3A—C13A—H15A	108.9	N3B—C13B—H15B	109.8
C12A—C13A—H15A	108.9	C12B—C13B—H15B	109.8
N3A—C13A—H14A	108.9	N3B—C13B—H14B	109.8
C12A—C13A—H14A	108.9	C12B—C13B—H14B	109.8
H15A—C13A—H14A	107.8	H15B—C13B—H14B	108.3
C1A—N3A—C13A	114.6 (2)	C21—N3B—C13B	117.4 (2)
C1A—N3A—C5A	126.35 (18)	C21—N3B—C5B	124.8 (2)
C13A—N3A—C5A	119.0 (2)	C13B—N3B—C5B	117.24 (19)
O1A—C1A—N1A—C2A	174.5 (2)	O1B—C21—N1B—C2B	−176.9 (2)
N3A—C1A—N1A—C2A	−7.1 (4)	N3B—C21—N1B—C2B	1.8 (4)
C1A—N1A—C2A—N2A	65.8 (3)	C21—N1B—C2B—N2B	50.6 (4)
N1A—C2A—N2A—C4A	−59.5 (3)	N1B—C2B—N2B—C4B	−65.2 (3)
N1A—C2A—N2A—C3A	98.4 (3)	N1B—C2B—N2B—C3B	110.5 (3)
C2A—N2A—C4A—O2A	163.3 (2)	C2B—N2B—C4B—O2B	177.4 (2)
C3A—N2A—C4A—O2A	5.0 (4)	C3B—N2B—C4B—O2B	1.7 (4)
C2A—N2A—C4A—C5A	−17.1 (3)	C2B—N2B—C4B—C5B	−1.4 (3)
C3A—N2A—C4A—C5A	−175.4 (2)	C3B—N2B—C4B—C5B	−177.0 (2)
O2A—C4A—C5A—N3A	−103.2 (3)	O2B—C4B—C5B—N3B	−106.5 (3)
N2A—C4A—C5A—N3A	77.1 (3)	N2B—C4B—C5B—N3B	72.3 (3)
O2A—C4A—C5A—C6A	18.4 (3)	O2B—C4B—C5B—C6B	15.2 (3)
N2A—C4A—C5A—C6A	−161.2 (2)	N2B—C4B—C5B—C6B	−166.0 (2)
N3A—C5A—C6A—C7A	−50.5 (3)	N3B—C5B—C6B—C7B	−52.0 (3)
C4A—C5A—C6A—C7A	−171.9 (2)	C4B—C5B—C6B—C7B	−173.4 (2)
C5A—C6A—C7A—C12A	43.9 (3)	C5B—C6B—C7B—C12B	51.5 (3)
C5A—C6A—C7A—C8A	−137.9 (3)	C5B—C6B—C7B—C8B	−127.7 (3)
C12A—C7A—C8A—C9A	0.5 (5)	C12B—C7B—C8B—C9B	0.1 (5)
C6A—C7A—C8A—C9A	−177.7 (3)	C6B—C7B—C8B—C9B	179.3 (3)
C7A—C8A—C9A—C10A	1.3 (5)	C7B—C8B—C9B—C10B	1.0 (6)
C8A—C9A—C10A—C11A	−2.5 (5)	C8B—C9B—C10B—C11B	−1.4 (7)
C9A—C10A—C11A—C12A	1.7 (5)	C9B—C10B—C11B—C12B	0.7 (6)
C8A—C7A—C12A—C11A	−1.3 (4)	C8B—C7B—C12B—C11B	−0.8 (4)
C6A—C7A—C12A—C11A	177.0 (3)	C6B—C7B—C12B—C11B	180.0 (3)
C8A—C7A—C12A—C13A	−176.3 (3)	C8B—C7B—C12B—C13B	179.0 (3)
C6A—C7A—C12A—C13A	2.0 (4)	C6B—C7B—C12B—C13B	−0.2 (3)
C10A—C11A—C12A—C7A	0.2 (4)	C10B—C11B—C12B—C7B	0.4 (4)
C10A—C11A—C12A—C13A	175.0 (3)	C10B—C11B—C12B—C13B	−179.4 (3)
C7A—C12A—C13A—N3A	−39.4 (4)	C7B—C12B—C13B—N3B	−48.2 (3)
C11A—C12A—C13A—N3A	145.7 (3)	C11B—C12B—C13B—N3B	131.6 (3)
O1A—C1A—N3A—C13A	−6.9 (3)	O1B—C21—N3B—C13B	−4.6 (4)
N1A—C1A—N3A—C13A	174.8 (2)	N1B—C21—N3B—C13B	176.8 (2)
O1A—C1A—N3A—C5A	173.8 (2)	O1B—C21—N3B—C5B	−175.5 (2)
N1A—C1A—N3A—C5A	−4.5 (4)	N1B—C21—N3B—C5B	5.9 (4)
C12A—C13A—N3A—C1A	−149.1 (2)	C12B—C13B—N3B—C21	−126.1 (2)
C12A—C13A—N3A—C5A	30.3 (3)	C12B—C13B—N3B—C5B	45.5 (3)
C6A—C5A—N3A—C1A	−167.5 (2)	C4B—C5B—N3B—C21	−63.8 (3)
C4A—C5A—N3A—C1A	−47.9 (3)	C6B—C5B—N3B—C21	174.3 (2)
C6A—C5A—N3A—C13A	13.2 (3)	C4B—C5B—N3B—C13B	125.3 (2)
C4A—C5A—N3A—C13A	132.9 (2)	C6B—C5B—N3B—C13B	3.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O2A^i	0.86	2.11	2.967 (3)	171
N1B—H1B···O2B^ii	0.86	2.02	2.827 (3)	156
C2B—H3B···O1A^iii	0.97	2.48	3.239 (3)	135
C3B—H4B···Cg^iv	0.97	2.87	3.700 (3)	145

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