4-[3-(1H-Imidazol-1-yl)prop­yl]-3-phenyl-1H-1,2,4-triazol-5(4H)-one

The title compound, C₁₄H₁₅N₅O, has two similar independent mol­ecules in the asymmetric unit. The crystal structure is stabilized by C—H...O, C—H...N and N—H...N inter­molecular hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.047
• wR factor = 0.105
• Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12

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           26.00
           From the CIF: _reflns_number_total               2953
           Count of symmetry unique reflns         3075
           Completeness (_total/calc)             96.03%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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 (Farrugia, 1999).

4-[3-(1H-Imidazol-1-yl)propyl]-3-phenyl-1H-1,2,4-triazol-5(4H)-one

Crystal data

C14H15N5O	Dx = 1.289 Mg m^−3
Mr = 269.31	Melting point = 456–457 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2237 reflections
a = 10.073 (5) Å	θ = 2.3–26.0°
b = 15.594 (8) Å	µ = 0.09 mm^−1
c = 17.669 (9) Å	T = 293 K
V = 2775 (2) Å^3	Prism, colourless
Z = 8	0.50 × 0.45 × 0.40 mm
F(000) = 1136

Data collection

Bruker SMART CCD area-detector diffractometer	2237 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 26.0°, θmin = 2.3°
φ and ω scans	h = −8→12
13657 measured reflections	k = −19→19
2953 independent reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0623P)^2] where P = (Fo^2 + 2Fc^2)/3
2953 reflections	(Δ/σ)max < 0.001
362 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
N2B	0.0427 (2)	0.35199 (14)	0.19297 (11)	0.0430 (5)
N3B	0.0644 (2)	0.55298 (15)	0.01770 (13)	0.0539 (6)
C8B	−0.0184 (3)	0.59490 (17)	−0.03183 (15)	0.0511 (8)
C4B	−0.0611 (3)	0.3650 (2)	0.13666 (15)	0.0549 (8)
H4B2	−0.1340	0.3961	0.1598	0.066*
H4B1	−0.0946	0.3096	0.1206	0.066*
N5B	0.0425 (3)	0.61543 (16)	−0.09378 (14)	0.0631 (7)
C6B	0.0296 (3)	0.50458 (17)	0.08641 (13)	0.0500 (7)
H6B2	−0.0419	0.5338	0.1127	0.060*
H6B1	0.1057	0.5027	0.1200	0.060*
C9B	−0.1573 (3)	0.61681 (17)	−0.01750 (15)	0.0473 (7)
N4B	0.1691 (3)	0.58538 (18)	−0.08347 (15)	0.0722 (8)
H7B	0.2309	0.5912	−0.1167	0.087*
C2B	0.1389 (3)	0.29074 (19)	0.19174 (15)	0.0500 (7)
H2B	0.1522	0.2496	0.1544	0.060*
C5B	−0.0133 (3)	0.41417 (18)	0.06763 (15)	0.0562 (8)
H5B1	0.0609	0.3837	0.0451	0.067*
H5B2	−0.0841	0.4163	0.0305	0.067*
N1B	0.1621 (3)	0.36827 (17)	0.29559 (14)	0.0635 (8)
C3B	0.0609 (3)	0.39623 (19)	0.25697 (16)	0.0595 (8)
H3B	0.0075	0.4417	0.2721	0.071*
O1B	0.2866 (3)	0.51084 (18)	0.00934 (14)	0.0891 (8)
C7B	0.1878 (4)	0.5456 (2)	−0.01591 (18)	0.0639 (9)
C10B	−0.1950 (3)	0.6629 (2)	0.04638 (16)	0.0584 (8)
H10B	−0.1310	0.6781	0.0819	0.070*
C11B	−0.3246 (3)	0.6863 (2)	0.05790 (19)	0.0680 (9)
H11B	−0.3475	0.7179	0.1006	0.082*
C1B	0.2106 (3)	0.3012 (2)	0.25458 (16)	0.0554 (8)
H1B	0.2830	0.2677	0.2684	0.066*
C12B	−0.4196 (4)	0.6637 (3)	0.0073 (2)	0.0784 (10)
H12B	−0.5075	0.6793	0.0156	0.094*
C14B	−0.2561 (4)	0.5950 (2)	−0.06789 (19)	0.0692 (10)
H14B	−0.2347	0.5639	−0.1111	0.083*
C13B	−0.3867 (4)	0.6185 (3)	−0.0553 (2)	0.0790 (11)
H13B	−0.4520	0.6032	−0.0899	0.095*
N2A	0.5421 (2)	0.34817 (14)	0.06132 (11)	0.0433 (5)
N3A	0.5819 (2)	0.55965 (14)	0.22840 (12)	0.0436 (5)
N4A	0.6829 (3)	0.59900 (15)	0.32935 (14)	0.0575 (7)
H7A	0.7432	0.6064	0.3632	0.069*
C8A	0.4969 (3)	0.60634 (16)	0.27371 (14)	0.0461 (7)
N1A	0.6579 (3)	0.35869 (16)	−0.04299 (12)	0.0576 (7)
N5A	0.5562 (3)	0.63157 (15)	0.33515 (13)	0.0575 (7)
O1A	0.8015 (2)	0.51731 (16)	0.24348 (13)	0.0727 (7)
C6A	0.5473 (3)	0.50718 (16)	0.16327 (13)	0.0460 (6)
H6A1	0.6242	0.5020	0.1305	0.055*
H6A2	0.4776	0.5355	0.1348	0.055*
C7A	0.7020 (3)	0.55446 (19)	0.26513 (16)	0.0515 (7)
C5A	0.5006 (3)	0.41853 (17)	0.18566 (14)	0.0542 (8)
H5A2	0.4330	0.4239	0.2245	0.065*
H5A1	0.5746	0.3872	0.2073	0.065*
C9A	0.3597 (3)	0.62835 (18)	0.25528 (16)	0.0503 (7)
C4A	0.4444 (3)	0.36764 (19)	0.11982 (14)	0.0540 (8)
H4A1	0.4080	0.3143	0.1389	0.065*
H4A2	0.3722	0.3999	0.0973	0.065*
C3A	0.5610 (3)	0.39115 (18)	−0.00330 (15)	0.0547 (8)
H3A	0.5111	0.4384	−0.0181	0.066*
C2A	0.6338 (3)	0.2845 (2)	0.06285 (17)	0.0562 (8)
H2A	0.6459	0.2440	0.1009	0.067*
C1A	0.7031 (3)	0.29136 (19)	−0.00115 (16)	0.0563 (8)
H1A	0.7724	0.2553	−0.0152	0.068*
C12A	0.1028 (4)	0.6735 (3)	0.2198 (3)	0.0885 (13)
H12A	0.0162	0.6896	0.2084	0.106*
C14A	0.2569 (4)	0.6083 (2)	0.3039 (2)	0.0688 (9)
H14A	0.2743	0.5798	0.3490	0.083*
C11A	0.2005 (5)	0.6929 (3)	0.1719 (2)	0.0977 (14)
H11A	0.1813	0.7209	0.1268	0.117*
C10A	0.3307 (4)	0.6715 (3)	0.1890 (2)	0.0813 (12)
H10A	0.3986	0.6863	0.1559	0.098*
C13A	0.1282 (4)	0.6306 (3)	0.2852 (3)	0.0839 (12)
H13A	0.0588	0.6163	0.3175	0.101*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N2B	0.0464 (14)	0.0483 (12)	0.0343 (11)	−0.0056 (12)	−0.0023 (10)	0.0031 (9)
N3B	0.0574 (16)	0.0581 (14)	0.0461 (13)	0.0092 (13)	0.0138 (12)	0.0100 (12)
C8B	0.067 (2)	0.0463 (15)	0.0396 (15)	0.0054 (15)	0.0023 (14)	0.0014 (12)
C4B	0.0585 (19)	0.0612 (18)	0.0448 (15)	−0.0102 (16)	−0.0119 (14)	0.0069 (13)
N5B	0.0771 (19)	0.0605 (15)	0.0517 (14)	0.0119 (16)	0.0188 (14)	0.0124 (12)
C6B	0.0584 (18)	0.0571 (16)	0.0344 (13)	0.0018 (16)	0.0054 (13)	0.0072 (12)
C9B	0.0589 (19)	0.0394 (13)	0.0437 (14)	0.0014 (14)	0.0012 (14)	0.0008 (13)
N4B	0.076 (2)	0.0727 (17)	0.0674 (17)	0.0188 (16)	0.0328 (15)	0.0200 (14)
C2B	0.0534 (18)	0.0566 (17)	0.0399 (15)	0.0073 (16)	0.0033 (13)	−0.0022 (13)
C5B	0.072 (2)	0.0630 (17)	0.0336 (13)	−0.0032 (17)	−0.0111 (14)	0.0019 (13)
N1B	0.0660 (19)	0.0746 (18)	0.0498 (14)	0.0097 (16)	−0.0190 (13)	−0.0101 (13)
C3B	0.074 (2)	0.0609 (19)	0.0440 (16)	0.0103 (18)	−0.0098 (16)	−0.0118 (14)
O1B	0.0665 (16)	0.1042 (19)	0.0966 (19)	0.0278 (16)	0.0185 (15)	0.0306 (16)
C7B	0.067 (2)	0.0631 (19)	0.0619 (19)	0.0114 (18)	0.0214 (18)	0.0129 (16)
C10B	0.058 (2)	0.0636 (19)	0.0538 (17)	−0.0046 (18)	−0.0018 (14)	−0.0052 (15)
C11B	0.062 (2)	0.076 (2)	0.066 (2)	0.009 (2)	0.0125 (18)	−0.0025 (17)
C1B	0.0432 (17)	0.072 (2)	0.0512 (17)	0.0037 (16)	0.0013 (14)	0.0063 (16)
C12B	0.058 (2)	0.094 (3)	0.082 (3)	0.010 (2)	0.001 (2)	0.022 (2)
C14B	0.085 (3)	0.064 (2)	0.0586 (19)	0.000 (2)	−0.0084 (18)	−0.0115 (17)
C13B	0.064 (3)	0.095 (3)	0.078 (3)	−0.012 (2)	−0.0237 (19)	0.008 (2)
N2A	0.0494 (14)	0.0482 (12)	0.0322 (11)	−0.0097 (12)	0.0051 (10)	−0.0026 (9)
N3A	0.0453 (13)	0.0450 (12)	0.0405 (11)	0.0017 (11)	−0.0030 (10)	−0.0080 (10)
N4A	0.0633 (18)	0.0567 (14)	0.0525 (13)	0.0103 (14)	−0.0216 (12)	−0.0139 (12)
C8A	0.0565 (18)	0.0377 (14)	0.0440 (15)	0.0075 (14)	−0.0018 (13)	−0.0049 (12)
N1A	0.0687 (18)	0.0638 (16)	0.0404 (12)	−0.0012 (15)	0.0151 (12)	−0.0011 (12)
N5A	0.0664 (18)	0.0579 (14)	0.0481 (13)	0.0150 (14)	−0.0124 (13)	−0.0132 (12)
O1A	0.0513 (14)	0.0882 (16)	0.0787 (15)	0.0181 (13)	−0.0113 (12)	−0.0175 (13)
C6A	0.0535 (17)	0.0491 (15)	0.0353 (13)	0.0032 (15)	−0.0018 (12)	−0.0050 (11)
C7A	0.0490 (18)	0.0522 (16)	0.0532 (16)	0.0037 (15)	−0.0067 (15)	−0.0050 (14)
C5A	0.068 (2)	0.0587 (16)	0.0354 (14)	−0.0116 (16)	0.0124 (13)	−0.0054 (12)
C9A	0.0548 (19)	0.0450 (15)	0.0512 (17)	0.0076 (14)	−0.0048 (15)	−0.0105 (13)
C4A	0.0584 (19)	0.0599 (17)	0.0438 (15)	−0.0194 (16)	0.0165 (14)	−0.0095 (13)
C3A	0.070 (2)	0.0560 (16)	0.0378 (14)	0.0112 (17)	0.0107 (15)	0.0049 (13)
C2A	0.067 (2)	0.0522 (17)	0.0495 (17)	0.0018 (18)	−0.0051 (16)	0.0041 (14)
C1A	0.0609 (19)	0.0568 (17)	0.0514 (17)	0.0090 (16)	0.0015 (16)	−0.0117 (15)
C12A	0.060 (2)	0.105 (3)	0.101 (3)	0.026 (2)	−0.015 (2)	−0.038 (3)
C14A	0.068 (2)	0.064 (2)	0.075 (2)	−0.003 (2)	0.0002 (18)	−0.0062 (18)
C11A	0.093 (3)	0.114 (3)	0.086 (3)	0.044 (3)	−0.023 (3)	−0.001 (3)
C10A	0.068 (3)	0.108 (3)	0.068 (2)	0.031 (2)	0.0000 (18)	0.014 (2)
C13A	0.057 (2)	0.092 (3)	0.103 (3)	−0.003 (2)	0.011 (2)	−0.022 (3)

Geometric parameters (Å, º)

N2B—C3B	1.337 (3)	N2A—C3A	1.338 (3)
N2B—C2B	1.361 (4)	N2A—C2A	1.357 (4)
N2B—C4B	1.458 (3)	N2A—C4A	1.459 (3)
N3B—C8B	1.374 (3)	N3A—C7A	1.375 (4)
N3B—C7B	1.383 (4)	N3A—C8A	1.380 (3)
N3B—C6B	1.472 (3)	N3A—C6A	1.454 (3)
C8B—N5B	1.295 (4)	N4A—C7A	1.344 (4)
C8B—C9B	1.463 (4)	N4A—N5A	1.378 (4)
C4B—C5B	1.520 (4)	N4A—H7A	0.8600
C4B—H4B2	0.9700	C8A—N5A	1.300 (3)
C4B—H4B1	0.9700	C8A—C9A	1.460 (4)
N5B—N4B	1.370 (4)	N1A—C3A	1.304 (4)
C6B—C5B	1.511 (4)	N1A—C1A	1.362 (4)
C6B—H6B2	0.9700	O1A—C7A	1.219 (3)
C6B—H6B1	0.9700	C6A—C5A	1.513 (4)
C9B—C14B	1.378 (4)	C6A—H6A1	0.9700
C9B—C10B	1.391 (4)	C6A—H6A2	0.9700
N4B—C7B	1.358 (4)	C5A—C4A	1.518 (4)
N4B—H7B	0.8600	C5A—H5A2	0.9700
C2B—C1B	1.334 (4)	C5A—H5A1	0.9700
C2B—H2B	0.9300	C9A—C14A	1.381 (5)
C5B—H5B1	0.9700	C9A—C10A	1.382 (4)
C5B—H5B2	0.9700	C4A—H4A1	0.9700
N1B—C3B	1.301 (4)	C4A—H4A2	0.9700
N1B—C1B	1.363 (4)	C3A—H3A	0.9300
C3B—H3B	0.9300	C2A—C1A	1.333 (4)
O1B—C7B	1.218 (4)	C2A—H2A	0.9300
C10B—C11B	1.371 (4)	C1A—H1A	0.9300
C10B—H10B	0.9300	C12A—C11A	1.333 (6)
C11B—C12B	1.357 (5)	C12A—C13A	1.360 (6)
C11B—H11B	0.9300	C12A—H12A	0.9300
C1B—H1B	0.9300	C14A—C13A	1.382 (6)
C12B—C13B	1.352 (5)	C14A—H14A	0.9300
C12B—H12B	0.9300	C11A—C10A	1.386 (5)
C14B—C13B	1.384 (5)	C11A—H11A	0.9300
C14B—H14B	0.9300	C10A—H10A	0.9300
C13B—H13B	0.9300	C13A—H13A	0.9300
C3B—N2B—C2B	106.1 (2)	C3A—N2A—C2A	106.7 (2)
C3B—N2B—C4B	127.2 (3)	C3A—N2A—C4A	126.6 (3)
C2B—N2B—C4B	126.7 (2)	C2A—N2A—C4A	126.7 (2)
C8B—N3B—C7B	108.2 (2)	C7A—N3A—C8A	107.7 (2)
C8B—N3B—C6B	128.7 (2)	C7A—N3A—C6A	123.5 (2)
C7B—N3B—C6B	121.7 (2)	C8A—N3A—C6A	127.3 (2)
N5B—C8B—N3B	111.6 (3)	C7A—N4A—N5A	112.7 (2)
N5B—C8B—C9B	122.8 (3)	C7A—N4A—H7A	123.6
N3B—C8B—C9B	125.6 (2)	N5A—N4A—H7A	123.6
N2B—C4B—C5B	113.0 (2)	N5A—C8A—N3A	111.0 (3)
N2B—C4B—H4B2	109.0	N5A—C8A—C9A	123.4 (3)
C5B—C4B—H4B2	109.0	N3A—C8A—C9A	125.6 (2)
N2B—C4B—H4B1	109.0	C3A—N1A—C1A	104.9 (2)
C5B—C4B—H4B1	109.0	C8A—N5A—N4A	104.6 (2)
H4B2—C4B—H4B1	107.8	N3A—C6A—C5A	112.4 (2)
C8B—N5B—N4B	104.1 (3)	N3A—C6A—H6A1	109.1
N3B—C6B—C5B	111.4 (2)	C5A—C6A—H6A1	109.1
N3B—C6B—H6B2	109.3	N3A—C6A—H6A2	109.1
C5B—C6B—H6B2	109.3	C5A—C6A—H6A2	109.1
N3B—C6B—H6B1	109.3	H6A1—C6A—H6A2	107.8
C5B—C6B—H6B1	109.3	O1A—C7A—N4A	128.9 (3)
H6B2—C6B—H6B1	108.0	O1A—C7A—N3A	127.1 (3)
C14B—C9B—C10B	117.1 (3)	N4A—C7A—N3A	104.0 (2)
C14B—C9B—C8B	121.4 (3)	C6A—C5A—C4A	113.2 (2)
C10B—C9B—C8B	121.5 (3)	C6A—C5A—H5A2	108.9
C7B—N4B—N5B	113.7 (3)	C4A—C5A—H5A2	108.9
C7B—N4B—H7B	123.1	C6A—C5A—H5A1	108.9
N5B—N4B—H7B	123.1	C4A—C5A—H5A1	108.9
C1B—C2B—N2B	106.6 (3)	H5A2—C5A—H5A1	107.8
C1B—C2B—H2B	126.7	C14A—C9A—C10A	118.6 (3)
N2B—C2B—H2B	126.7	C14A—C9A—C8A	121.2 (3)
C6B—C5B—C4B	112.7 (2)	C10A—C9A—C8A	120.2 (3)
C6B—C5B—H5B1	109.1	N2A—C4A—C5A	113.6 (2)
C4B—C5B—H5B1	109.1	N2A—C4A—H4A1	108.8
C6B—C5B—H5B2	109.1	C5A—C4A—H4A1	108.8
C4B—C5B—H5B2	109.1	N2A—C4A—H4A2	108.8
H5B1—C5B—H5B2	107.8	C5A—C4A—H4A2	108.8
C3B—N1B—C1B	105.0 (2)	H4A1—C4A—H4A2	107.7
N1B—C3B—N2B	112.2 (3)	N1A—C3A—N2A	111.8 (3)
N1B—C3B—H3B	123.9	N1A—C3A—H3A	124.1
N2B—C3B—H3B	123.9	N2A—C3A—H3A	124.1
O1B—C7B—N4B	129.7 (3)	C1A—C2A—N2A	106.3 (3)
O1B—C7B—N3B	127.9 (3)	C1A—C2A—H2A	126.9
N4B—C7B—N3B	102.4 (3)	N2A—C2A—H2A	126.9
C11B—C10B—C9B	121.2 (3)	C2A—C1A—N1A	110.3 (3)
C11B—C10B—H10B	119.4	C2A—C1A—H1A	124.8
C9B—C10B—H10B	119.4	N1A—C1A—H1A	124.8
C12B—C11B—C10B	120.3 (3)	C11A—C12A—C13A	120.8 (4)
C12B—C11B—H11B	119.8	C11A—C12A—H12A	119.6
C10B—C11B—H11B	119.8	C13A—C12A—H12A	119.6
C2B—C1B—N1B	110.0 (3)	C9A—C14A—C13A	119.9 (4)
C2B—C1B—H1B	125.0	C9A—C14A—H14A	120.1
N1B—C1B—H1B	125.0	C13A—C14A—H14A	120.1
C13B—C12B—C11B	120.1 (4)	C12A—C11A—C10A	120.4 (4)
C13B—C12B—H12B	120.0	C12A—C11A—H11A	119.8
C11B—C12B—H12B	120.0	C10A—C11A—H11A	119.8
C9B—C14B—C13B	121.1 (3)	C9A—C10A—C11A	120.1 (4)
C9B—C14B—H14B	119.4	C9A—C10A—H10A	119.9
C13B—C14B—H14B	119.4	C11A—C10A—H10A	119.9
C12B—C13B—C14B	120.2 (3)	C12A—C13A—C14A	120.2 (4)
C12B—C13B—H13B	119.9	C12A—C13A—H13A	119.9
C14B—C13B—H13B	119.9	C14A—C13A—H13A	119.9
C7B—N3B—C8B—N5B	−0.6 (3)	C7A—N3A—C8A—N5A	1.0 (3)
C6B—N3B—C8B—N5B	−166.8 (3)	C6A—N3A—C8A—N5A	167.2 (2)
C7B—N3B—C8B—C9B	−179.0 (3)	C7A—N3A—C8A—C9A	178.8 (3)
C6B—N3B—C8B—C9B	14.9 (4)	C6A—N3A—C8A—C9A	−15.1 (4)
C3B—N2B—C4B—C5B	100.9 (3)	N3A—C8A—N5A—N4A	−0.7 (3)
C2B—N2B—C4B—C5B	−80.8 (3)	C9A—C8A—N5A—N4A	−178.6 (3)
N3B—C8B—N5B—N4B	0.1 (3)	C7A—N4A—N5A—C8A	0.2 (3)
C9B—C8B—N5B—N4B	178.5 (3)	C7A—N3A—C6A—C5A	81.5 (3)
C8B—N3B—C6B—C5B	82.3 (3)	C8A—N3A—C6A—C5A	−82.6 (3)
C7B—N3B—C6B—C5B	−82.2 (3)	N5A—N4A—C7A—O1A	−179.3 (3)
N5B—C8B—C9B—C14B	53.6 (4)	N5A—N4A—C7A—N3A	0.4 (3)
N3B—C8B—C9B—C14B	−128.2 (3)	C8A—N3A—C7A—O1A	178.9 (3)
N5B—C8B—C9B—C10B	−124.4 (3)	C6A—N3A—C7A—O1A	12.1 (5)
N3B—C8B—C9B—C10B	53.9 (4)	C8A—N3A—C7A—N4A	−0.8 (3)
C8B—N5B—N4B—C7B	0.5 (4)	C6A—N3A—C7A—N4A	−167.6 (2)
C3B—N2B—C2B—C1B	−0.3 (3)	N3A—C6A—C5A—C4A	171.3 (2)
C4B—N2B—C2B—C1B	−178.8 (3)	N5A—C8A—C9A—C14A	−56.9 (4)
N3B—C6B—C5B—C4B	−175.1 (2)	N3A—C8A—C9A—C14A	125.6 (3)
N2B—C4B—C5B—C6B	−63.8 (3)	N5A—C8A—C9A—C10A	121.8 (3)
C1B—N1B—C3B—N2B	−0.9 (4)	N3A—C8A—C9A—C10A	−55.7 (4)
C2B—N2B—C3B—N1B	0.8 (3)	C3A—N2A—C4A—C5A	−97.8 (3)
C4B—N2B—C3B—N1B	179.3 (3)	C2A—N2A—C4A—C5A	80.2 (3)
N5B—N4B—C7B—O1B	178.2 (4)	C6A—C5A—C4A—N2A	64.5 (3)
N5B—N4B—C7B—N3B	−0.8 (4)	C1A—N1A—C3A—N2A	0.0 (3)
C8B—N3B—C7B—O1B	−178.3 (3)	C2A—N2A—C3A—N1A	0.4 (3)
C6B—N3B—C7B—O1B	−10.9 (5)	C4A—N2A—C3A—N1A	178.7 (2)
C8B—N3B—C7B—N4B	0.8 (3)	C3A—N2A—C2A—C1A	−0.5 (3)
C6B—N3B—C7B—N4B	168.1 (2)	C4A—N2A—C2A—C1A	−178.8 (3)
C14B—C9B—C10B—C11B	−0.8 (5)	N2A—C2A—C1A—N1A	0.5 (3)
C8B—C9B—C10B—C11B	177.2 (3)	C3A—N1A—C1A—C2A	−0.3 (3)
C9B—C10B—C11B—C12B	1.0 (5)	C10A—C9A—C14A—C13A	0.7 (5)
N2B—C2B—C1B—N1B	−0.3 (3)	C8A—C9A—C14A—C13A	179.4 (3)
C3B—N1B—C1B—C2B	0.7 (4)	C13A—C12A—C11A—C10A	−1.7 (7)
C10B—C11B—C12B—C13B	−0.6 (6)	C14A—C9A—C10A—C11A	−0.8 (6)
C10B—C9B—C14B—C13B	0.3 (5)	C8A—C9A—C10A—C11A	−179.6 (4)
C8B—C9B—C14B—C13B	−177.7 (3)	C12A—C11A—C10A—C9A	1.4 (7)
C11B—C12B—C13B—C14B	0.1 (6)	C11A—C12A—C13A—C14A	1.6 (6)
C9B—C14B—C13B—C12B	0.0 (6)	C9A—C14A—C13A—C12A	−1.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H7A···N1A^i	0.86	2.01	2.845 (4)	164
N4B—H7B···N1B^ii	0.86	1.99	2.825 (4)	163
C2B—H2B···N1A^iii	0.93	2.59	3.518 (4)	172
C3A—H3A···O1B	0.93	2.57	3.343 (4)	140
C3B—H3B···O1A^iv	0.93	2.44	3.233 (4)	143
C4A—H4A2···O1B	0.97	2.48	3.365 (4)	152
C4B—H4B2···O1A^iv	0.97	2.49	3.335 (4)	146

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