N,N′,N′′′-Triphenyl­guanidinium nitrate

The title salt, C₁₉H₁₈N₃⁺·NO₃⁻, has two symmetry-independent cations and two symmetry-independent anions in the asymmetric unit, with almost identical geometries. Bond lengths and angles within the guanidinium unit are close to those expected for a Csp² atom. Inter­molecular hydrogen bonds link anions and cations, forming chains that run along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.054
• wR factor = 0.165
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        N4C
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        N4D
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 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

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: SDP-Plus (Frenz, 1985); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

N,N',N''-triphenylguanidinium nitrate

Crystal data

C19H18N3^+·NO3^−	Z = 4
Mr = 350.37	F(000) = 736
Triclinic, P1	Dx = 1.284 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.783 (3) Å	Cell parameters from 25 reflections
b = 13.849 (3) Å	θ = 9.8–13.6°
c = 14.237 (3) Å	µ = 0.09 mm^−1
α = 76.285 (13)°	T = 293 K
β = 89.264 (12)°	Thin square plate, clear pale yellow
γ = 75.609 (12)°	0.49 × 0.44 × 0.09 mm
V = 1812.8 (8) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.043
Radiation source: fine-focus sealed tube	θmax = 25.5°, θmin = 2.6°
Graphite monochromator	h = −11→11
profile data from ω–2θ scans	k = −16→16
11545 measured reflections	l = −16→16
6704 independent reflections	3 standard reflections every 180 min
3901 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.165	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0881P)^2 + 0.2511P] where P = (Fo^2 + 2Fc^2)/3
6704 reflections	(Δ/σ)max < 0.001
469 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.30 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
N1A	0.1236 (2)	0.16779 (15)	1.08809 (14)	0.0450 (5)
H1A	0.0593	0.1529	1.1265	0.054*
N2A	0.2025 (2)	−0.00100 (15)	1.09285 (15)	0.0464 (5)
H2A	0.1834	−0.0091	1.1529	0.056*
N3A	0.2365 (2)	0.11753 (16)	0.95546 (14)	0.0446 (5)
H3A	0.3095	0.0744	0.9423	0.054*
C1A	0.1895 (3)	0.09529 (19)	1.04365 (17)	0.0416 (6)
C2A	0.1476 (3)	0.26627 (18)	1.07922 (17)	0.0407 (6)
C3A	0.2686 (3)	0.2918 (2)	1.0456 (2)	0.0517 (7)
H31A	0.3397	0.2441	1.0250	0.062*
C4A	0.2849 (3)	0.3887 (2)	1.0425 (2)	0.0609 (8)
H4A	0.3666	0.4065	1.0188	0.073*
C5A	0.1809 (4)	0.4591 (2)	1.0744 (2)	0.0633 (8)
H5A	0.1916	0.5247	1.0714	0.076*
C6A	0.0626 (4)	0.4324 (2)	1.1103 (2)	0.0628 (8)
H6A	−0.0060	0.4792	1.1339	0.075*
C7A	0.0429 (3)	0.3365 (2)	1.1122 (2)	0.0515 (7)
H7A	−0.0395	0.3193	1.1353	0.062*
C8A	0.1775 (3)	0.20558 (19)	0.88112 (17)	0.0427 (6)
C9A	0.2663 (3)	0.2442 (2)	0.8138 (2)	0.0573 (8)
H9A	0.3632	0.2148	0.8195	0.069*
C10A	0.2080 (5)	0.3273 (3)	0.7383 (2)	0.0722 (10)
H10A	0.2667	0.3530	0.6924	0.087*
C11A	0.0681 (5)	0.3720 (3)	0.7294 (2)	0.0744 (10)
H11A	0.0311	0.4283	0.6784	0.089*
C12A	−0.0186 (4)	0.3339 (2)	0.7959 (2)	0.0664 (9)
H12A	−0.1152	0.3644	0.7900	0.080*
C13A	0.0355 (3)	0.2505 (2)	0.87175 (19)	0.0519 (7)
H13A	−0.0246	0.2248	0.9165	0.062*
C14A	0.2438 (3)	−0.09278 (19)	1.05951 (19)	0.0433 (6)
C15A	0.2086 (3)	−0.0989 (2)	0.96868 (19)	0.0488 (7)
H15A	0.1551	−0.0412	0.9249	0.059*
C16A	0.2525 (3)	−0.1908 (2)	0.9424 (2)	0.0593 (8)
H16A	0.2309	−0.1946	0.8802	0.071*
C17A	0.3279 (4)	−0.2768 (2)	1.0076 (3)	0.0691 (9)
H17A	0.3568	−0.3389	0.9898	0.083*
C18A	0.3602 (4)	−0.2710 (2)	1.0987 (3)	0.0713 (9)
H18A	0.4105	−0.3296	1.1430	0.086*
C19A	0.3192 (3)	−0.1788 (2)	1.1260 (2)	0.0562 (7)
H19A	0.3419	−0.1750	1.1880	0.067*
N1B	0.6174 (2)	0.16547 (15)	0.33693 (14)	0.0449 (5)
H1B	0.5565	0.1481	0.3057	0.054*
N2B	0.7025 (2)	−0.00300 (15)	0.40739 (15)	0.0462 (5)
H2B	0.6839	−0.0109	0.3512	0.055*
N3B	0.7332 (2)	0.11660 (16)	0.48981 (15)	0.0461 (5)
H3B	0.8043	0.0725	0.5229	0.055*
C1B	0.6861 (3)	0.09382 (18)	0.41325 (17)	0.0410 (6)
C14B	0.7465 (3)	−0.09475 (18)	0.48128 (18)	0.0417 (6)
C15B	0.7137 (3)	−0.1020 (2)	0.57673 (18)	0.0473 (6)
H15B	0.6607	−0.0448	0.5959	0.057*
C16B	0.7600 (3)	−0.1946 (2)	0.6436 (2)	0.0560 (7)
H16B	0.7405	−0.1993	0.7084	0.067*
C17B	0.8343 (4)	−0.2797 (2)	0.6154 (2)	0.0663 (9)
H17B	0.8652	−0.3420	0.6609	0.080*
C18B	0.8632 (4)	−0.2730 (2)	0.5201 (2)	0.0689 (9)
H18B	0.9119	−0.3312	0.5007	0.083*
C19B	0.8207 (3)	−0.1806 (2)	0.4527 (2)	0.0560 (7)
H19B	0.8418	−0.1761	0.3881	0.067*
C2B	0.6334 (3)	0.26665 (19)	0.30151 (17)	0.0429 (6)
C3B	0.7554 (3)	0.2934 (2)	0.3165 (2)	0.0521 (7)
H31B	0.8315	0.2451	0.3525	0.063*
C4B	0.7647 (4)	0.3926 (2)	0.2777 (2)	0.0613 (8)
H4B	0.8465	0.4116	0.2890	0.074*
C5B	0.6540 (4)	0.4633 (2)	0.2226 (2)	0.0706 (9)
H5B	0.6605	0.5302	0.1968	0.085*
C6B	0.5347 (4)	0.4354 (2)	0.2060 (3)	0.0766 (10)
H6B	0.4605	0.4830	0.1674	0.092*
C7B	0.5228 (3)	0.3369 (2)	0.2461 (2)	0.0598 (8)
H7B	0.4402	0.3185	0.2355	0.072*
C8B	0.6776 (3)	0.2068 (2)	0.52236 (17)	0.0453 (6)
C9B	0.7694 (4)	0.2458 (2)	0.5658 (2)	0.0674 (9)
H9B	0.8657	0.2144	0.5723	0.081*
C10B	0.7150 (6)	0.3329 (3)	0.5997 (3)	0.0899 (13)
H10B	0.7757	0.3587	0.6309	0.108*
C11B	0.5765 (6)	0.3808 (3)	0.5886 (3)	0.0946 (13)
H11B	0.5424	0.4402	0.6104	0.114*
C12B	0.4872 (4)	0.3422 (3)	0.5454 (3)	0.0797 (11)
H12B	0.3914	0.3753	0.5376	0.096*
C13B	0.5367 (3)	0.2544 (2)	0.5128 (2)	0.0580 (8)
H13B	0.4743	0.2276	0.4844	0.070*
O1D	0.4632 (2)	0.09339 (17)	0.21283 (16)	0.0700 (6)
O2D	0.5130 (2)	0.01587 (17)	0.09816 (14)	0.0649 (6)
O3D	0.6608 (2)	−0.01962 (16)	0.21877 (14)	0.0632 (6)
N4D	0.5445 (2)	0.02932 (18)	0.17679 (16)	0.0482 (6)
O2C	0.0156 (2)	0.01468 (18)	0.39649 (13)	0.0669 (6)
O3C	0.1647 (2)	−0.02060 (16)	0.29041 (13)	0.0652 (6)
O1C	−0.0316 (2)	0.09374 (18)	0.24718 (14)	0.0718 (6)
N4C	0.0483 (3)	0.02896 (18)	0.31123 (15)	0.0501 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0551 (14)	0.0418 (12)	0.0385 (11)	−0.0116 (10)	0.0126 (10)	−0.0115 (10)
N2A	0.0606 (14)	0.0394 (12)	0.0351 (11)	−0.0071 (10)	0.0089 (10)	−0.0074 (9)
N3A	0.0511 (13)	0.0404 (12)	0.0395 (11)	−0.0061 (10)	0.0102 (10)	−0.0103 (10)
C1A	0.0481 (15)	0.0400 (14)	0.0359 (13)	−0.0094 (12)	0.0062 (11)	−0.0095 (11)
C2A	0.0522 (16)	0.0365 (13)	0.0316 (12)	−0.0081 (12)	−0.0019 (11)	−0.0078 (10)
C3A	0.0526 (17)	0.0545 (17)	0.0505 (16)	−0.0109 (14)	−0.0001 (13)	−0.0199 (13)
C4A	0.066 (2)	0.066 (2)	0.0566 (17)	−0.0256 (16)	−0.0028 (15)	−0.0159 (15)
C5A	0.079 (2)	0.0437 (16)	0.0676 (19)	−0.0181 (16)	−0.0045 (17)	−0.0117 (15)
C6A	0.073 (2)	0.0445 (17)	0.0676 (19)	−0.0032 (15)	0.0034 (17)	−0.0201 (15)
C7A	0.0562 (17)	0.0445 (15)	0.0527 (16)	−0.0090 (13)	0.0101 (13)	−0.0138 (13)
C8A	0.0586 (17)	0.0404 (14)	0.0344 (12)	−0.0183 (13)	0.0085 (12)	−0.0135 (11)
C9A	0.069 (2)	0.0595 (18)	0.0518 (16)	−0.0266 (16)	0.0169 (15)	−0.0189 (15)
C10A	0.115 (3)	0.065 (2)	0.0468 (17)	−0.049 (2)	0.0221 (19)	−0.0082 (16)
C11A	0.122 (3)	0.0544 (19)	0.0434 (17)	−0.025 (2)	−0.003 (2)	−0.0023 (15)
C12A	0.079 (2)	0.064 (2)	0.0489 (17)	−0.0066 (17)	−0.0103 (16)	−0.0099 (15)
C13A	0.0580 (18)	0.0564 (17)	0.0415 (14)	−0.0167 (14)	0.0055 (13)	−0.0100 (13)
C14A	0.0443 (15)	0.0379 (14)	0.0469 (14)	−0.0083 (12)	0.0066 (12)	−0.0110 (12)
C15A	0.0559 (17)	0.0439 (15)	0.0469 (15)	−0.0140 (13)	0.0078 (13)	−0.0105 (12)
C16A	0.065 (2)	0.0638 (19)	0.0613 (18)	−0.0264 (16)	0.0178 (15)	−0.0293 (16)
C17A	0.065 (2)	0.0504 (18)	0.100 (3)	−0.0118 (16)	0.0131 (19)	−0.0358 (19)
C18A	0.064 (2)	0.0396 (16)	0.100 (3)	−0.0010 (15)	−0.0049 (19)	−0.0097 (17)
C19A	0.0600 (18)	0.0417 (15)	0.0621 (18)	−0.0080 (13)	−0.0080 (14)	−0.0080 (14)
N1B	0.0565 (14)	0.0402 (12)	0.0395 (11)	−0.0143 (10)	−0.0070 (10)	−0.0096 (10)
N2B	0.0649 (15)	0.0395 (12)	0.0348 (11)	−0.0115 (11)	−0.0023 (10)	−0.0116 (9)
N3B	0.0571 (14)	0.0407 (12)	0.0387 (11)	−0.0087 (10)	−0.0067 (10)	−0.0095 (9)
C1B	0.0456 (15)	0.0395 (14)	0.0376 (13)	−0.0109 (12)	0.0017 (11)	−0.0088 (11)
C14B	0.0444 (15)	0.0378 (13)	0.0430 (14)	−0.0127 (12)	0.0005 (11)	−0.0076 (11)
C15B	0.0569 (17)	0.0451 (15)	0.0417 (14)	−0.0161 (13)	0.0058 (12)	−0.0108 (12)
C16B	0.0632 (19)	0.0626 (19)	0.0418 (14)	−0.0223 (15)	0.0005 (13)	−0.0050 (14)
C17B	0.069 (2)	0.0517 (18)	0.064 (2)	−0.0084 (16)	0.0006 (16)	0.0062 (15)
C18B	0.074 (2)	0.0449 (17)	0.077 (2)	−0.0005 (15)	0.0113 (18)	−0.0093 (16)
C19B	0.0655 (19)	0.0458 (16)	0.0536 (16)	−0.0087 (14)	0.0120 (14)	−0.0121 (13)
C2B	0.0544 (16)	0.0368 (13)	0.0376 (13)	−0.0107 (12)	0.0048 (12)	−0.0101 (11)
C3B	0.0530 (17)	0.0505 (16)	0.0490 (15)	−0.0110 (14)	0.0092 (13)	−0.0072 (13)
C4B	0.068 (2)	0.0564 (18)	0.0648 (19)	−0.0253 (16)	0.0108 (16)	−0.0145 (16)
C5B	0.096 (3)	0.0423 (17)	0.072 (2)	−0.0239 (18)	−0.0049 (19)	−0.0051 (15)
C6B	0.093 (3)	0.0426 (17)	0.085 (2)	−0.0126 (17)	−0.029 (2)	−0.0023 (17)
C7B	0.068 (2)	0.0432 (16)	0.0649 (19)	−0.0126 (15)	−0.0142 (16)	−0.0068 (14)
C8B	0.0610 (18)	0.0425 (14)	0.0348 (13)	−0.0172 (13)	0.0029 (12)	−0.0097 (11)
C9B	0.083 (2)	0.064 (2)	0.0629 (19)	−0.0281 (18)	−0.0087 (17)	−0.0207 (16)
C10B	0.139 (4)	0.073 (2)	0.073 (2)	−0.040 (3)	−0.018 (2)	−0.032 (2)
C11B	0.150 (4)	0.066 (2)	0.075 (2)	−0.020 (3)	0.010 (3)	−0.039 (2)
C12B	0.093 (3)	0.073 (2)	0.073 (2)	−0.007 (2)	0.021 (2)	−0.0324 (19)
C13B	0.064 (2)	0.0635 (19)	0.0554 (17)	−0.0213 (16)	0.0155 (15)	−0.0261 (15)
O1D	0.0621 (13)	0.0808 (15)	0.0720 (14)	0.0009 (11)	0.0023 (11)	−0.0475 (13)
O2D	0.0616 (13)	0.0898 (15)	0.0516 (12)	−0.0127 (11)	0.0003 (10)	−0.0395 (11)
O3D	0.0671 (14)	0.0676 (13)	0.0474 (11)	0.0061 (11)	−0.0046 (10)	−0.0233 (10)
N4D	0.0529 (14)	0.0546 (14)	0.0417 (12)	−0.0133 (12)	0.0088 (11)	−0.0213 (11)
O2C	0.0636 (13)	0.0930 (16)	0.0373 (11)	−0.0173 (12)	0.0100 (9)	−0.0056 (10)
O3C	0.0666 (14)	0.0707 (14)	0.0427 (11)	0.0047 (11)	0.0050 (10)	−0.0071 (10)
O1C	0.0632 (14)	0.0819 (15)	0.0472 (11)	0.0022 (12)	0.0008 (10)	0.0074 (11)
N4C	0.0544 (15)	0.0569 (14)	0.0364 (12)	−0.0150 (12)	0.0006 (11)	−0.0054 (11)

Geometric parameters (Å, º)

N1A—C1A	1.339 (3)	N2B—C1B	1.333 (3)
N1A—C2A	1.417 (3)	N2B—C14B	1.419 (3)
N1A—H1A	0.8600	N2B—H2B	0.8600
N2A—C1A	1.327 (3)	N3B—C1B	1.322 (3)
N2A—C14A	1.425 (3)	N3B—C8B	1.415 (3)
N2A—H2A	0.8600	N3B—H3B	0.8600
N3A—C1A	1.325 (3)	C14B—C19B	1.378 (4)
N3A—C8A	1.412 (3)	C14B—C15B	1.378 (4)
N3A—H3A	0.8600	C15B—C16B	1.379 (4)
C2A—C3A	1.367 (4)	C15B—H15B	0.9300
C2A—C7A	1.387 (4)	C16B—C17B	1.367 (4)
C3A—C4A	1.380 (4)	C16B—H16B	0.9300
C3A—H31A	0.9300	C17B—C18B	1.369 (4)
C4A—C5A	1.378 (4)	C17B—H17B	0.9300
C4A—H4A	0.9300	C18B—C19B	1.377 (4)
C5A—C6A	1.358 (5)	C18B—H18B	0.9300
C5A—H5A	0.9300	C19B—H19B	0.9300
C6A—C7A	1.383 (4)	C2B—C3B	1.368 (4)
C6A—H6A	0.9300	C2B—C7B	1.370 (4)
C7A—H7A	0.9300	C3B—C4B	1.378 (4)
C8A—C13A	1.368 (4)	C3B—H31B	0.9300
C8A—C9A	1.387 (4)	C4B—C5B	1.370 (4)
C9A—C10A	1.381 (4)	C4B—H4B	0.9300
C9A—H9A	0.9300	C5B—C6B	1.357 (5)
C10A—C11A	1.349 (5)	C5B—H5B	0.9300
C10A—H10A	0.9300	C6B—C7B	1.381 (4)
C11A—C12A	1.363 (5)	C6B—H6B	0.9300
C11A—H11A	0.9300	C7B—H7B	0.9300
C12A—C13A	1.378 (4)	C8B—C13B	1.365 (4)
C12A—H12A	0.9300	C8B—C9B	1.376 (4)
C13A—H13A	0.9300	C9B—C10B	1.386 (5)
C14A—C15A	1.370 (4)	C9B—H9B	0.9300
C14A—C19A	1.381 (4)	C10B—C11B	1.346 (6)
C15A—C16A	1.375 (4)	C10B—H10B	0.9300
C15A—H15A	0.9300	C11B—C12B	1.352 (6)
C16A—C17A	1.372 (5)	C11B—H11B	0.9300
C16A—H16A	0.9300	C12B—C13B	1.378 (4)
C17A—C18A	1.364 (5)	C12B—H12B	0.9300
C17A—H17A	0.9300	C13B—H13B	0.9300
C18A—C19A	1.384 (4)	O1D—N4D	1.240 (3)
C18A—H18A	0.9300	O2D—N4D	1.232 (3)
C19A—H19A	0.9300	O3D—N4D	1.246 (3)
N1B—C1B	1.339 (3)	O2C—N4C	1.234 (3)
N1B—C2B	1.419 (3)	O3C—N4C	1.247 (3)
N1B—H1B	0.8600	O1C—N4C	1.237 (3)
C1A—N1A—C2A	127.5 (2)	C1B—N2B—C14B	128.7 (2)
C1A—N1A—H1A	116.2	C1B—N2B—H2B	115.6
C2A—N1A—H1A	116.2	C14B—N2B—H2B	115.6
C1A—N2A—C14A	128.7 (2)	C1B—N3B—C8B	126.1 (2)
C1A—N2A—H2A	115.7	C1B—N3B—H3B	117.0
C14A—N2A—H2A	115.7	C8B—N3B—H3B	117.0
C1A—N3A—C8A	125.9 (2)	N3B—C1B—N2B	121.9 (2)
C1A—N3A—H3A	117.0	N3B—C1B—N1B	122.9 (2)
C8A—N3A—H3A	117.0	N2B—C1B—N1B	115.2 (2)
N3A—C1A—N2A	121.7 (2)	C19B—C14B—C15B	120.0 (2)
N3A—C1A—N1A	122.6 (2)	C19B—C14B—N2B	116.5 (2)
N2A—C1A—N1A	115.7 (2)	C15B—C14B—N2B	123.5 (2)
C3A—C2A—C7A	120.2 (2)	C14B—C15B—C16B	119.5 (2)
C3A—C2A—N1A	123.7 (2)	C14B—C15B—H15B	120.3
C7A—C2A—N1A	116.0 (2)	C16B—C15B—H15B	120.3
C2A—C3A—C4A	119.7 (3)	C17B—C16B—C15B	120.5 (3)
C2A—C3A—H31A	120.1	C17B—C16B—H16B	119.7
C4A—C3A—H31A	120.1	C15B—C16B—H16B	119.7
C5A—C4A—C3A	120.4 (3)	C16B—C17B—C18B	119.8 (3)
C5A—C4A—H4A	119.8	C16B—C17B—H17B	120.1
C3A—C4A—H4A	119.8	C18B—C17B—H17B	120.1
C6A—C5A—C4A	119.6 (3)	C17B—C18B—C19B	120.5 (3)
C6A—C5A—H5A	120.2	C17B—C18B—H18B	119.8
C4A—C5A—H5A	120.2	C19B—C18B—H18B	119.8
C5A—C6A—C7A	120.9 (3)	C18B—C19B—C14B	119.6 (3)
C5A—C6A—H6A	119.6	C18B—C19B—H19B	120.2
C7A—C6A—H6A	119.6	C14B—C19B—H19B	120.2
C6A—C7A—C2A	119.1 (3)	C3B—C2B—C7B	120.3 (3)
C6A—C7A—H7A	120.5	C3B—C2B—N1B	122.7 (2)
C2A—C7A—H7A	120.5	C7B—C2B—N1B	116.9 (3)
C13A—C8A—C9A	119.7 (3)	C2B—C3B—C4B	119.5 (3)
C13A—C8A—N3A	121.7 (2)	C2B—C3B—H31B	120.3
C9A—C8A—N3A	118.5 (3)	C4B—C3B—H31B	120.3
C10A—C9A—C8A	118.7 (3)	C5B—C4B—C3B	120.4 (3)
C10A—C9A—H9A	120.6	C5B—C4B—H4B	119.8
C8A—C9A—H9A	120.6	C3B—C4B—H4B	119.8
C11A—C10A—C9A	121.6 (3)	C6B—C5B—C4B	119.7 (3)
C11A—C10A—H10A	119.2	C6B—C5B—H5B	120.1
C9A—C10A—H10A	119.2	C4B—C5B—H5B	120.1
C10A—C11A—C12A	119.4 (3)	C5B—C6B—C7B	120.5 (3)
C10A—C11A—H11A	120.3	C5B—C6B—H6B	119.7
C12A—C11A—H11A	120.3	C7B—C6B—H6B	119.7
C11A—C12A—C13A	120.6 (3)	C2B—C7B—C6B	119.5 (3)
C11A—C12A—H12A	119.7	C2B—C7B—H7B	120.2
C13A—C12A—H12A	119.7	C6B—C7B—H7B	120.2
C8A—C13A—C12A	119.9 (3)	C13B—C8B—C9B	119.9 (3)
C8A—C13A—H13A	120.0	C13B—C8B—N3B	121.8 (3)
C12A—C13A—H13A	120.0	C9B—C8B—N3B	118.3 (3)
C15A—C14A—C19A	120.5 (2)	C8B—C9B—C10B	118.5 (3)
C15A—C14A—N2A	123.5 (2)	C8B—C9B—H9B	120.8
C19A—C14A—N2A	115.9 (2)	C10B—C9B—H9B	120.8
C14A—C15A—C16A	119.8 (3)	C11B—C10B—C9B	121.5 (4)
C14A—C15A—H15A	120.1	C11B—C10B—H10B	119.2
C16A—C15A—H15A	120.1	C9B—C10B—H10B	119.2
C17A—C16A—C15A	120.3 (3)	C10B—C11B—C12B	119.6 (3)
C17A—C16A—H16A	119.9	C10B—C11B—H11B	120.2
C15A—C16A—H16A	119.9	C12B—C11B—H11B	120.2
C18A—C17A—C16A	119.8 (3)	C11B—C12B—C13B	120.6 (4)
C18A—C17A—H17A	120.1	C11B—C12B—H12B	119.7
C16A—C17A—H17A	120.1	C13B—C12B—H12B	119.7
C17A—C18A—C19A	120.8 (3)	C8B—C13B—C12B	119.9 (3)
C17A—C18A—H18A	119.6	C8B—C13B—H13B	120.1
C19A—C18A—H18A	119.6	C12B—C13B—H13B	120.1
C14A—C19A—C18A	118.8 (3)	O2D—N4D—O1D	120.5 (2)
C14A—C19A—H19A	120.6	O2D—N4D—O3D	119.6 (2)
C18A—C19A—H19A	120.6	O1D—N4D—O3D	119.9 (2)
C1B—N1B—C2B	127.6 (2)	O2C—N4C—O1C	120.5 (2)
C1B—N1B—H1B	116.2	O2C—N4C—O3C	119.4 (2)
C2B—N1B—H1B	116.2	O1C—N4C—O3C	120.1 (2)
C8A—N3A—C1A—N2A	148.7 (3)	C8B—N3B—C1B—N2B	−153.1 (3)
C8A—N3A—C1A—N1A	−29.9 (4)	C8B—N3B—C1B—N1B	26.1 (4)
C14A—N2A—C1A—N3A	−10.9 (4)	C14B—N2B—C1B—N3B	11.7 (4)
C14A—N2A—C1A—N1A	167.8 (2)	C14B—N2B—C1B—N1B	−167.5 (2)
C2A—N1A—C1A—N3A	−32.7 (4)	C2B—N1B—C1B—N3B	29.9 (4)
C2A—N1A—C1A—N2A	148.6 (2)	C2B—N1B—C1B—N2B	−151.0 (2)
C1A—N1A—C2A—C3A	−19.7 (4)	C1B—N2B—C14B—C19B	−148.6 (3)
C1A—N1A—C2A—C7A	163.8 (2)	C1B—N2B—C14B—C15B	34.2 (4)
C7A—C2A—C3A—C4A	−1.5 (4)	C19B—C14B—C15B—C16B	2.4 (4)
N1A—C2A—C3A—C4A	−177.8 (2)	N2B—C14B—C15B—C16B	179.4 (3)
C2A—C3A—C4A—C5A	1.0 (4)	C14B—C15B—C16B—C17B	−1.9 (4)
C3A—C4A—C5A—C6A	0.9 (5)	C15B—C16B—C17B—C18B	0.0 (5)
C4A—C5A—C6A—C7A	−2.3 (5)	C16B—C17B—C18B—C19B	1.5 (5)
C5A—C6A—C7A—C2A	1.7 (5)	C17B—C18B—C19B—C14B	−1.1 (5)
C3A—C2A—C7A—C6A	0.2 (4)	C15B—C14B—C19B—C18B	−0.9 (4)
N1A—C2A—C7A—C6A	176.7 (2)	N2B—C14B—C19B—C18B	−178.2 (3)
C1A—N3A—C8A—C13A	−32.9 (4)	C1B—N1B—C2B—C3B	25.6 (4)
C1A—N3A—C8A—C9A	149.8 (3)	C1B—N1B—C2B—C7B	−157.9 (3)
C13A—C8A—C9A—C10A	−0.5 (4)	C7B—C2B—C3B—C4B	1.9 (4)
N3A—C8A—C9A—C10A	176.8 (2)	N1B—C2B—C3B—C4B	178.3 (2)
C8A—C9A—C10A—C11A	0.9 (5)	C2B—C3B—C4B—C5B	−1.6 (4)
C9A—C10A—C11A—C12A	−0.7 (5)	C3B—C4B—C5B—C6B	−0.2 (5)
C10A—C11A—C12A—C13A	0.1 (5)	C4B—C5B—C6B—C7B	1.5 (6)
C9A—C8A—C13A—C12A	−0.2 (4)	C3B—C2B—C7B—C6B	−0.6 (4)
N3A—C8A—C13A—C12A	−177.4 (2)	N1B—C2B—C7B—C6B	−177.1 (3)
C11A—C12A—C13A—C8A	0.4 (5)	C5B—C6B—C7B—C2B	−1.2 (5)
C1A—N2A—C14A—C15A	−35.5 (4)	C1B—N3B—C8B—C13B	34.0 (4)
C1A—N2A—C14A—C19A	146.7 (3)	C1B—N3B—C8B—C9B	−146.9 (3)
C19A—C14A—C15A—C16A	−2.1 (4)	C13B—C8B—C9B—C10B	0.5 (5)
N2A—C14A—C15A—C16A	−179.8 (2)	N3B—C8B—C9B—C10B	−178.6 (3)
C14A—C15A—C16A—C17A	1.8 (4)	C8B—C9B—C10B—C11B	−1.9 (6)
C15A—C16A—C17A—C18A	−0.4 (5)	C9B—C10B—C11B—C12B	1.6 (6)
C16A—C17A—C18A—C19A	−0.7 (5)	C10B—C11B—C12B—C13B	0.0 (6)
C15A—C14A—C19A—C18A	0.9 (4)	C9B—C8B—C13B—C12B	1.0 (4)
N2A—C14A—C19A—C18A	178.8 (3)	N3B—C8B—C13B—C12B	−179.9 (3)
C17A—C18A—C19A—C14A	0.5 (5)	C11B—C12B—C13B—C8B	−1.3 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1C^i	0.86	2.02	2.841 (3)	160
N1B—H1B···O1D	0.86	2.00	2.837 (3)	164
N2A—H2A···O3C^i	0.86	1.94	2.790 (3)	172
N2B—H2B···O3D	0.86	1.94	2.792 (3)	173
N3A—H3A···O2D^ii	0.86	2.04	2.893 (3)	174
N3A—H3A···O3D^ii	0.86	2.57	3.139 (3)	124
N3B—H3B···O2C^ii	0.86	2.05	2.907 (3)	172
N3B—H3B···O3C^ii	0.86	2.58	3.163 (3)	126
C3A—H31A···N3A	0.93	2.61	3.071 (3)	111

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