Di­cyclo­hexyl­aminium 4-nitro­anthranilate

The crystal structure of di­cyclo­hexyl­amnium 4-nitro­anthra­nilate, C₁₂H₂₄N⁺·C₇H₅N₂O₄⁻, shows a three-dimensional hydrogen-bonded network polymer in which the protonated amine groups of both of the independent mol­ecules of di­cyclo­hexyl­amine give similar hydrogen-bonding interactions with oxy­gen acceptors of four separate anthranilate carboxyl­ate groups [N...O = 2.730 (3)–2.782 (2) Å]. Secondary centrosymmetric peripheral hydrogen-bonding linkages involve the amine groups of the anthranilate anions with nitro and carboxyl­ate O-atom acceptors, while these groups are also involved in intramolecular N—H...O(carboxyl­ate) associations [2.663 (3) and 2.679 (3) Å].

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.150
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........          ?
PLAT156_ALERT_4_C Axial System Input Cell not Standard ...........          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        N4A
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        N4B

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: PLATON for Windows.

N-cyclohexylcyclohexanaminium 2-amino-4-nitrobenzoate

Crystal data

C12H24N^+·C7H5N2O4^−	Z = 4
Mr = 363.45	F(000) = 784
Triclinic, P1	Dx = 1.244 Mg m^−3
Hall symbol: -P 1	Melting point = 394.2–395.1 K
a = 12.486 (2) Å	Mo Kα radiation, λ = 0.71069 Å
b = 13.1960 (19) Å	Cell parameters from 25 reflections
c = 12.068 (2) Å	θ = 12.6–16.9°
α = 98.775 (14)°	µ = 0.09 mm^−1
β = 90.839 (14)°	T = 295 K
γ = 98.860 (12)°	Block, orange
V = 1940.2 (5) Å^3	0.34 × 0.30 × 0.20 mm

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.016
Radiation source: Rigaku rotating anode	θmax = 25.0°, θmin = 2.5°
Graphite monochromator	h = −14→14
ω–2θ scans	k = −15→15
7699 measured reflections	l = −6→14
6830 independent reflections	3 standard reflections every 150 reflections
4384 reflections with I > 2σ(I)	intensity decay: 2.7%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.151	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.5711P] where P = (Fo^2 + 2Fc^2)/3
S = 0.89	(Δ/σ)max = 0.013
6830 reflections	Δρmax = 0.20 e Å^−3
502 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0054 (12)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
N1C	0.66786 (15)	0.49367 (14)	0.51677 (17)	0.0470 (6)
C1C	0.67701 (19)	0.38070 (17)	0.48784 (18)	0.0513 (8)
C2C	0.5645 (2)	0.32076 (19)	0.4546 (2)	0.0633 (9)
C3C	0.5655 (3)	0.2046 (2)	0.4267 (2)	0.0822 (13)
C4C	0.6172 (3)	0.1645 (2)	0.5221 (2)	0.0779 (12)
C5C	0.7299 (3)	0.2231 (2)	0.5521 (2)	0.0730 (10)
C6C	0.7283 (2)	0.33932 (19)	0.5833 (2)	0.0585 (8)
C7C	0.76681 (17)	0.56761 (17)	0.56508 (18)	0.0493 (7)
C8C	0.85921 (19)	0.56697 (19)	0.4858 (2)	0.0597 (9)
C9C	0.9580 (2)	0.6420 (2)	0.5369 (3)	0.0796 (11)
C10C	0.9324 (2)	0.7507 (2)	0.5677 (3)	0.0855 (13)
C11C	0.8368 (3)	0.7524 (2)	0.6428 (3)	0.0805 (11)
C12C	0.7380 (2)	0.67567 (19)	0.5933 (2)	0.0579 (8)
N1D	0.83565 (14)	0.98262 (15)	0.05850 (15)	0.0422 (6)
C1D	0.75099 (16)	0.98862 (16)	−0.02896 (17)	0.0429 (7)
C2D	0.80614 (19)	0.99674 (19)	−0.1395 (2)	0.0559 (8)
C3D	0.7230 (2)	0.9980 (2)	−0.2329 (2)	0.0689 (10)
C4D	0.6535 (2)	1.0822 (2)	−0.2021 (2)	0.0704 (10)
C5D	0.60264 (19)	1.0743 (2)	−0.0905 (2)	0.0619 (9)
C6D	0.68828 (18)	1.07824 (17)	0.00175 (19)	0.0518 (8)
C7D	0.80193 (16)	0.98805 (15)	0.17795 (17)	0.0424 (6)
C8D	0.70367 (17)	0.90812 (18)	0.18876 (19)	0.0527 (8)
C9D	0.6734 (2)	0.9091 (2)	0.3101 (2)	0.0729 (10)
C10D	0.7682 (3)	0.8957 (2)	0.3834 (2)	0.0783 (11)
C11D	0.8663 (2)	0.9754 (2)	0.3723 (2)	0.0739 (10)
C12D	0.89714 (18)	0.97344 (18)	0.2507 (2)	0.0556 (8)
O41A	0.94843 (16)	0.69529 (14)	0.25555 (19)	0.0848 (8)
O42A	1.09989 (18)	0.73343 (14)	0.1807 (2)	0.0997 (9)
O71A	1.12779 (12)	0.22052 (11)	0.00488 (14)	0.0578 (6)
O72A	0.97486 (12)	0.16978 (11)	0.08494 (15)	0.0604 (6)
N2A	0.85772 (19)	0.3124 (2)	0.1728 (3)	0.0843 (12)
N4A	1.02635 (17)	0.67082 (14)	0.20513 (18)	0.0576 (7)
C1A	1.03895 (15)	0.35085 (15)	0.10391 (16)	0.0386 (6)
C2A	0.94513 (16)	0.38229 (16)	0.15333 (18)	0.0455 (7)
C3A	0.94319 (16)	0.48867 (17)	0.18545 (19)	0.0495 (7)
C4A	1.03123 (16)	0.55980 (15)	0.17058 (17)	0.0435 (7)
C5A	1.12444 (17)	0.53137 (17)	0.1249 (2)	0.0519 (8)
C6A	1.12638 (16)	0.42706 (17)	0.0933 (2)	0.0498 (7)
C7A	1.04752 (16)	0.23825 (16)	0.06128 (17)	0.0423 (6)
O41B	0.55626 (16)	0.76679 (16)	−0.17153 (16)	0.0817 (8)
O42B	0.38891 (15)	0.70149 (19)	−0.17682 (15)	0.0854 (9)
O71B	0.45888 (14)	0.49619 (13)	0.30071 (14)	0.0648 (6)
O72B	0.63249 (15)	0.56392 (15)	0.31889 (14)	0.0728 (7)
N2B	0.72455 (16)	0.64113 (17)	0.14404 (19)	0.0559 (7)
N4B	0.47993 (16)	0.71635 (15)	−0.13404 (15)	0.0517 (6)
C1B	0.53090 (16)	0.59107 (14)	0.16069 (16)	0.0394 (6)
C2B	0.62067 (15)	0.63713 (14)	0.10618 (16)	0.0381 (6)
C3B	0.60125 (16)	0.67758 (15)	0.00818 (17)	0.0403 (6)
C4B	0.49693 (16)	0.67075 (15)	−0.03233 (16)	0.0406 (6)
C5B	0.40807 (16)	0.62463 (17)	0.01763 (18)	0.0487 (7)
C6B	0.42785 (17)	0.58564 (17)	0.11453 (18)	0.0484 (7)
C7B	0.54165 (19)	0.54679 (16)	0.26780 (18)	0.0484 (7)
H1C	0.721300	0.372400	0.424700	0.0620*
H7C	0.789300	0.546700	0.632500	0.0590*
H11C	0.656 (2)	0.517 (2)	0.452 (2)	0.080 (8)*
H12C	0.617 (2)	0.4964 (18)	0.568 (2)	0.059 (7)*
H13C	0.994000	0.793900	0.606000	0.1030*
H14C	0.916100	0.776400	0.501200	0.1030*
H15C	0.818400	0.820400	0.653400	0.0970*
H16C	0.857000	0.735600	0.713000	0.0970*
H17C	0.712600	0.696400	0.527000	0.0700*
H18C	0.682500	0.675000	0.646400	0.0700*
H21C	0.518000	0.333300	0.515000	0.0760*
H22C	0.537800	0.344400	0.390500	0.0760*
H31C	0.605300	0.191000	0.361100	0.0990*
H32C	0.492900	0.169600	0.413400	0.0990*
H41C	0.574000	0.172600	0.585900	0.0940*
H42C	0.621500	0.093000	0.500000	0.0940*
H51C	0.759000	0.198400	0.614200	0.0880*
H52C	0.774400	0.211900	0.489600	0.0880*
H61C	0.687500	0.351300	0.648500	0.0700*
H62C	0.800600	0.374600	0.598100	0.0700*
H81C	0.877100	0.498900	0.471000	0.0720*
H82C	0.837400	0.586900	0.417600	0.0720*
H91C	0.982300	0.619300	0.602500	0.0960*
H92C	1.013700	0.642700	0.484000	0.0960*
H1D	0.700800	0.925700	−0.038300	0.0520*
H7D	0.784000	1.055100	0.202400	0.0510*
H11D	0.860 (2)	0.917 (2)	0.036 (2)	0.072 (8)*
H12D	0.8920 (18)	1.0361 (18)	0.0559 (18)	0.050 (6)*
H13D	0.786200	0.828300	0.361800	0.0940*
H14D	0.748200	0.903500	0.459600	0.0940*
H15D	0.850700	1.042400	0.401000	0.0890*
H16D	0.925700	0.961200	0.414300	0.0890*
H17D	0.918900	0.908600	0.223800	0.0670*
H18D	0.955700	1.027900	0.246800	0.0670*
H21D	0.842800	0.938900	−0.158700	0.0670*
H22D	0.857100	1.059000	−0.131300	0.0670*
H31D	0.760200	1.010000	−0.299000	0.0830*
H32D	0.677400	0.932400	−0.246700	0.0830*
H41D	0.597700	1.075000	−0.258400	0.0850*
H42D	0.697500	1.148100	−0.198000	0.0850*
H51D	0.554200	1.010600	−0.096400	0.0740*
H52D	0.563600	1.130500	−0.071700	0.0740*
H61D	0.654200	1.072400	0.070900	0.0620*
H62D	0.736600	1.142200	0.009000	0.0620*
H81D	0.644200	0.922900	0.147200	0.0630*
H82D	0.719100	0.841300	0.159000	0.0630*
H91D	0.650400	0.973300	0.337200	0.0880*
H92D	0.615600	0.853700	0.313600	0.0880*
H3A	0.880300	0.511300	0.217800	0.0590*
H5A	1.185200	0.581900	0.115600	0.0620*
H6A	1.190700	0.406200	0.062800	0.0600*
H21A	0.862 (2)	0.247 (2)	0.150 (2)	0.077 (9)*
H22A	0.800 (2)	0.333 (2)	0.191 (2)	0.064 (8)*
H3B	0.660100	0.709500	−0.030000	0.0480*
H5B	0.336500	0.619800	−0.013000	0.0580*
H6B	0.367800	0.553600	0.151100	0.0580*
H21B	0.731 (2)	0.622 (2)	0.212 (2)	0.070 (8)*
H22B	0.779 (2)	0.6816 (19)	0.115 (2)	0.066 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1C	0.0491 (11)	0.0514 (11)	0.0433 (10)	0.0089 (8)	0.0048 (9)	0.0147 (8)
C1C	0.0640 (14)	0.0492 (13)	0.0434 (12)	0.0124 (11)	0.0090 (10)	0.0120 (10)
C2C	0.0803 (17)	0.0590 (15)	0.0499 (14)	0.0027 (13)	−0.0084 (12)	0.0153 (11)
C3C	0.125 (3)	0.0600 (16)	0.0575 (16)	−0.0004 (16)	−0.0093 (16)	0.0126 (13)
C4C	0.120 (3)	0.0541 (15)	0.0617 (16)	0.0108 (16)	0.0054 (16)	0.0183 (13)
C5C	0.098 (2)	0.0623 (16)	0.0695 (17)	0.0304 (15)	0.0145 (15)	0.0258 (13)
C6C	0.0607 (14)	0.0596 (15)	0.0603 (15)	0.0152 (12)	0.0017 (12)	0.0198 (12)
C7C	0.0504 (12)	0.0550 (13)	0.0454 (12)	0.0114 (10)	−0.0024 (10)	0.0145 (10)
C8C	0.0511 (13)	0.0580 (14)	0.0737 (17)	0.0135 (11)	0.0082 (12)	0.0164 (12)
C9C	0.0496 (14)	0.081 (2)	0.112 (2)	0.0104 (13)	−0.0035 (15)	0.0279 (17)
C10C	0.0606 (17)	0.0688 (18)	0.123 (3)	−0.0038 (14)	−0.0232 (17)	0.0185 (17)
C11C	0.092 (2)	0.0611 (17)	0.082 (2)	0.0116 (15)	−0.0267 (17)	−0.0052 (14)
C12C	0.0641 (15)	0.0592 (15)	0.0517 (13)	0.0168 (12)	0.0015 (11)	0.0058 (11)
N1D	0.0362 (9)	0.0385 (10)	0.0516 (11)	0.0049 (8)	0.0038 (8)	0.0070 (8)
C1D	0.0392 (11)	0.0411 (11)	0.0476 (12)	0.0023 (9)	−0.0007 (9)	0.0092 (9)
C2D	0.0564 (13)	0.0600 (14)	0.0542 (13)	0.0130 (11)	0.0111 (11)	0.0131 (11)
C3D	0.0787 (18)	0.0849 (19)	0.0468 (13)	0.0141 (15)	0.0045 (13)	0.0210 (13)
C4D	0.0683 (16)	0.0792 (18)	0.0710 (17)	0.0136 (14)	−0.0029 (14)	0.0332 (14)
C5D	0.0509 (13)	0.0681 (16)	0.0717 (17)	0.0170 (12)	−0.0007 (12)	0.0196 (13)
C6D	0.0473 (12)	0.0519 (13)	0.0585 (14)	0.0130 (10)	0.0031 (10)	0.0107 (11)
C7D	0.0434 (11)	0.0400 (11)	0.0439 (11)	0.0082 (9)	0.0020 (9)	0.0057 (9)
C8D	0.0442 (12)	0.0583 (14)	0.0558 (14)	0.0026 (10)	0.0036 (10)	0.0148 (11)
C9D	0.0665 (16)	0.089 (2)	0.0662 (17)	0.0072 (14)	0.0187 (14)	0.0254 (15)
C10D	0.095 (2)	0.089 (2)	0.0538 (15)	0.0103 (17)	0.0068 (15)	0.0247 (14)
C11D	0.0838 (19)	0.0809 (19)	0.0555 (15)	0.0086 (15)	−0.0139 (14)	0.0118 (14)
C12D	0.0498 (13)	0.0559 (14)	0.0591 (14)	0.0039 (10)	−0.0082 (11)	0.0082 (11)
O41A	0.0756 (13)	0.0571 (11)	0.1195 (17)	0.0230 (10)	0.0132 (12)	−0.0062 (11)
O42A	0.0853 (14)	0.0442 (11)	0.166 (2)	−0.0020 (10)	0.0225 (14)	0.0156 (12)
O71A	0.0548 (9)	0.0454 (9)	0.0731 (11)	0.0115 (7)	0.0166 (8)	0.0041 (8)
O72A	0.0549 (9)	0.0403 (8)	0.0829 (12)	−0.0028 (7)	0.0084 (8)	0.0093 (8)
N2A	0.0458 (13)	0.0547 (15)	0.145 (3)	−0.0027 (11)	0.0343 (14)	0.0005 (15)
N4A	0.0575 (12)	0.0412 (11)	0.0733 (14)	0.0106 (10)	−0.0087 (10)	0.0047 (9)
C1A	0.0352 (10)	0.0417 (11)	0.0397 (11)	0.0055 (8)	−0.0014 (8)	0.0094 (8)
C2A	0.0332 (10)	0.0465 (12)	0.0554 (13)	0.0019 (9)	0.0010 (9)	0.0078 (10)
C3A	0.0365 (11)	0.0503 (13)	0.0612 (14)	0.0099 (9)	0.0025 (10)	0.0040 (10)
C4A	0.0440 (11)	0.0383 (11)	0.0482 (12)	0.0068 (9)	−0.0061 (9)	0.0076 (9)
C5A	0.0444 (12)	0.0427 (12)	0.0663 (15)	−0.0030 (9)	0.0100 (11)	0.0101 (10)
C6A	0.0390 (11)	0.0474 (13)	0.0628 (14)	0.0054 (9)	0.0114 (10)	0.0083 (10)
C7A	0.0407 (11)	0.0406 (11)	0.0452 (11)	0.0042 (9)	−0.0036 (9)	0.0078 (9)
O41B	0.0815 (13)	0.0964 (14)	0.0684 (12)	−0.0149 (11)	−0.0065 (10)	0.0473 (11)
O42B	0.0547 (11)	0.148 (2)	0.0648 (12)	0.0234 (11)	−0.0026 (9)	0.0450 (12)
O71B	0.0705 (11)	0.0724 (11)	0.0569 (10)	0.0062 (9)	0.0199 (8)	0.0305 (9)
O72B	0.0733 (12)	0.0883 (13)	0.0582 (10)	−0.0057 (10)	−0.0132 (9)	0.0365 (9)
N2B	0.0419 (11)	0.0708 (14)	0.0597 (13)	0.0073 (9)	0.0021 (9)	0.0264 (11)
N4B	0.0537 (11)	0.0608 (12)	0.0427 (10)	0.0096 (9)	0.0012 (9)	0.0142 (9)
C1B	0.0465 (11)	0.0342 (10)	0.0374 (10)	0.0058 (8)	0.0056 (9)	0.0054 (8)
C2B	0.0412 (11)	0.0339 (10)	0.0399 (11)	0.0074 (8)	0.0027 (8)	0.0060 (8)
C3B	0.0419 (11)	0.0362 (10)	0.0427 (11)	0.0040 (8)	0.0075 (9)	0.0072 (8)
C4B	0.0458 (11)	0.0401 (11)	0.0368 (10)	0.0091 (9)	0.0020 (9)	0.0062 (8)
C5B	0.0409 (11)	0.0592 (14)	0.0461 (12)	0.0063 (10)	0.0013 (9)	0.0100 (10)
C6B	0.0431 (12)	0.0547 (13)	0.0454 (12)	−0.0007 (10)	0.0100 (10)	0.0095 (10)
C7B	0.0604 (14)	0.0438 (12)	0.0412 (12)	0.0063 (10)	0.0070 (11)	0.0089 (9)

Geometric parameters (Å, º)

O41A—N4A	1.215 (3)	C12C—H17C	0.9496
O42A—N4A	1.209 (3)	C12C—H18C	0.9507
O71A—C7A	1.251 (3)	C1D—C2D	1.521 (3)
O72A—C7A	1.247 (3)	C1D—C6D	1.520 (3)
O41B—N4B	1.210 (3)	C2D—C3D	1.525 (3)
O42B—N4B	1.216 (3)	C3D—C4D	1.519 (4)
O71B—C7B	1.246 (3)	C4D—C5D	1.508 (3)
O72B—C7B	1.255 (3)	C5D—C6D	1.522 (3)
N1C—C7C	1.501 (3)	C7D—C12D	1.521 (3)
N1C—C1C	1.501 (3)	C7D—C8D	1.511 (3)
N1C—H12C	0.89 (2)	C8D—C9D	1.516 (3)
N1C—H11C	0.90 (2)	C9D—C10D	1.515 (4)
N1D—C7D	1.502 (3)	C10D—C11D	1.508 (4)
N1D—C1D	1.502 (3)	C11D—C12D	1.520 (3)
N1D—H11D	0.96 (3)	C1D—H1D	0.9507
N1D—H12D	0.92 (2)	C2D—H21D	0.9500
N2A—C2A	1.364 (3)	C2D—H22D	0.9497
N4A—C4A	1.472 (3)	C3D—H31D	0.9507
N2A—H22A	0.83 (3)	C3D—H32D	0.9501
N2A—H21A	0.87 (3)	C4D—H41D	0.9498
N2B—C2B	1.359 (3)	C4D—H42D	0.9484
N4B—C4B	1.473 (3)	C5D—H51D	0.9494
N2B—H21B	0.90 (2)	C5D—H52D	0.9499
N2B—H22B	0.91 (3)	C6D—H61D	0.9504
C1C—C2C	1.518 (3)	C6D—H62D	0.9503
C1C—C6C	1.521 (3)	C7D—H7D	0.9504
C2C—C3C	1.520 (4)	C8D—H81D	0.9511
C3C—C4C	1.514 (4)	C8D—H82D	0.9494
C4C—C5C	1.508 (5)	C9D—H91D	0.9488
C5C—C6C	1.526 (4)	C9D—H92D	0.9512
C7C—C8C	1.510 (3)	C10D—H13D	0.9498
C7C—C12C	1.514 (3)	C10D—H14D	0.9510
C8C—C9C	1.516 (4)	C11D—H16D	0.9502
C9C—C10C	1.510 (4)	C11D—H15D	0.9493
C10C—C11C	1.510 (5)	C12D—H18D	0.9501
C11C—C12C	1.521 (4)	C12D—H17D	0.9491
C1C—H1C	0.9508	C1A—C6A	1.387 (3)
C2C—H21C	0.9492	C1A—C7A	1.517 (3)
C2C—H22C	0.9513	C1A—C2A	1.412 (3)
C3C—H31C	0.9495	C2A—C3A	1.402 (3)
C3C—H32C	0.9513	C3A—C4A	1.364 (3)
C4C—H41C	0.9487	C4A—C5A	1.375 (3)
C4C—H42C	0.9505	C5A—C6A	1.375 (3)
C5C—H52C	0.9503	C3A—H3A	0.9507
C5C—H51C	0.9502	C5A—H5A	0.9499
C6C—H62C	0.9508	C6A—H6A	0.9498
C6C—H61C	0.9498	C1B—C7B	1.510 (3)
C7C—H7C	0.9501	C1B—C2B	1.411 (3)
C8C—H81C	0.9501	C1B—C6B	1.382 (3)
C8C—H82C	0.9499	C2B—C3B	1.402 (3)
C9C—H92C	0.9509	C3B—C4B	1.369 (3)
C9C—H91C	0.9496	C4B—C5B	1.374 (3)
C10C—H14C	0.9487	C5B—C6B	1.381 (3)
C10C—H13C	0.9510	C3B—H3B	0.9505
C11C—H15C	0.9506	C5B—H5B	0.9512
C11C—H16C	0.9480	C6B—H6B	0.9511
C1C—N1C—C7C	118.09 (18)	N1D—C7D—C12D	108.87 (17)
C7C—N1C—H11C	101.5 (16)	N1D—C7D—C8D	111.49 (17)
C1C—N1C—H11C	107.3 (16)	C7D—C8D—C9D	111.63 (19)
C1C—N1C—H12C	105.1 (15)	C8D—C9D—C10D	111.7 (2)
C7C—N1C—H12C	107.4 (16)	C9D—C10D—C11D	111.2 (2)
H11C—N1C—H12C	118 (2)	C10D—C11D—C12D	111.6 (2)
C1D—N1D—C7D	117.56 (16)	C7D—C12D—C11D	111.00 (19)
C1D—N1D—H12D	107.8 (14)	C6D—C1D—H1D	108.13
C1D—N1D—H11D	105.4 (15)	N1D—C1D—H1D	108.13
C7D—N1D—H12D	107.8 (13)	C2D—C1D—H1D	108.13
H11D—N1D—H12D	110 (2)	C1D—C2D—H22D	109.14
C7D—N1D—H11D	108.4 (15)	C1D—C2D—H21D	109.22
O42A—N4A—C4A	118.2 (2)	C3D—C2D—H22D	109.17
O41A—N4A—O42A	123.1 (2)	C3D—C2D—H21D	109.20
O41A—N4A—C4A	118.71 (19)	H21D—C2D—H22D	109.41
C2A—N2A—H21A	116.0 (17)	C2D—C3D—H31D	108.86
H21A—N2A—H22A	123 (2)	C4D—C3D—H31D	108.93
C2A—N2A—H22A	119.5 (18)	C4D—C3D—H32D	109.00
O41B—N4B—C4B	119.16 (19)	C2D—C3D—H32D	108.81
O41B—N4B—O42B	122.7 (2)	H31D—C3D—H32D	109.38
O42B—N4B—C4B	118.11 (19)	C5D—C4D—H41D	109.02
H21B—N2B—H22B	122 (2)	C5D—C4D—H42D	109.06
C2B—N2B—H22B	119.4 (16)	H41D—C4D—H42D	109.51
C2B—N2B—H21B	114.7 (16)	C3D—C4D—H42D	109.05
C2C—C1C—C6C	111.25 (19)	C3D—C4D—H41D	108.96
N1C—C1C—C2C	108.16 (19)	C4D—C5D—H51D	109.02
N1C—C1C—C6C	112.56 (18)	H51D—C5D—H52D	109.44
C1C—C2C—C3C	111.8 (2)	C6D—C5D—H52D	109.04
C2C—C3C—C4C	111.1 (2)	C4D—C5D—H52D	108.96
C3C—C4C—C5C	111.1 (2)	C6D—C5D—H51D	109.07
C4C—C5C—C6C	111.1 (3)	C5D—C6D—H62D	109.69
C1C—C6C—C5C	110.5 (2)	H61D—C6D—H62D	109.37
N1C—C7C—C8C	111.71 (18)	C5D—C6D—H61D	109.65
C8C—C7C—C12C	110.73 (19)	C1D—C6D—H62D	109.60
N1C—C7C—C12C	109.21 (18)	C1D—C6D—H61D	109.63
C7C—C8C—C9C	110.5 (2)	C12D—C7D—H7D	108.49
C8C—C9C—C10C	111.4 (2)	C8D—C7D—H7D	108.42
C9C—C10C—C11C	111.3 (2)	N1D—C7D—H7D	108.44
C10C—C11C—C12C	112.4 (3)	C7D—C8D—H82D	108.89
C7C—C12C—C11C	110.4 (2)	C9D—C8D—H82D	109.07
N1C—C1C—H1C	108.23	H81D—C8D—H82D	109.46
C6C—C1C—H1C	108.25	C9D—C8D—H81D	108.93
C2C—C1C—H1C	108.25	C7D—C8D—H81D	108.84
C1C—C2C—H21C	108.91	C8D—C9D—H91D	108.91
C3C—C2C—H21C	108.91	H91D—C9D—H92D	109.53
C3C—C2C—H22C	108.86	C10D—C9D—H92D	108.84
C1C—C2C—H22C	108.85	C10D—C9D—H91D	109.09
H21C—C2C—H22C	109.44	C8D—C9D—H92D	108.72
C2C—C3C—H32C	109.04	H13D—C10D—H14D	109.42
H31C—C3C—H32C	109.38	C9D—C10D—H14D	109.13
C4C—C3C—H32C	108.99	C9D—C10D—H13D	109.30
C4C—C3C—H31C	109.11	C11D—C10D—H13D	108.94
C2C—C3C—H31C	109.16	C11D—C10D—H14D	108.80
C3C—C4C—H41C	109.20	C12D—C11D—H15D	108.85
H41C—C4C—H42C	109.56	C12D—C11D—H16D	108.83
C3C—C4C—H42C	109.10	C10D—C11D—H16D	108.97
C5C—C4C—H42C	108.88	C10D—C11D—H15D	108.97
C5C—C4C—H41C	109.02	H15D—C11D—H16D	109.56
C4C—C5C—H51C	109.16	C11D—C12D—H17D	109.01
C4C—C5C—H52C	109.15	H17D—C12D—H18D	109.54
H51C—C5C—H52C	109.52	C7D—C12D—H17D	109.21
C6C—C5C—H52C	108.99	C7D—C12D—H18D	109.12
C6C—C5C—H51C	108.92	C11D—C12D—H18D	108.95
C1C—C6C—H61C	109.17	C6A—C1A—C7A	118.99 (18)
C5C—C6C—H62C	109.24	C2A—C1A—C6A	118.05 (19)
H61C—C6C—H62C	109.43	C2A—C1A—C7A	122.96 (18)
C1C—C6C—H62C	109.21	N2A—C2A—C3A	119.2 (2)
C5C—C6C—H61C	109.33	C1A—C2A—C3A	118.71 (19)
C8C—C7C—H7C	108.36	N2A—C2A—C1A	122.0 (2)
N1C—C7C—H7C	108.34	C2A—C3A—C4A	120.26 (19)
C12C—C7C—H7C	108.40	N4A—C4A—C5A	118.88 (19)
C7C—C8C—H82C	109.19	C3A—C4A—C5A	122.3 (2)
H81C—C8C—H82C	109.44	N4A—C4A—C3A	118.82 (19)
C7C—C8C—H81C	109.16	C4A—C5A—C6A	117.5 (2)
C9C—C8C—H81C	109.25	C1A—C6A—C5A	123.2 (2)
C9C—C8C—H82C	109.25	O72A—C7A—C1A	118.15 (18)
C10C—C9C—H92C	108.99	O71A—C7A—C1A	117.42 (18)
C8C—C9C—H91C	108.98	O71A—C7A—O72A	124.4 (2)
H91C—C9C—H92C	109.47	C4A—C3A—H3A	119.88
C8C—C9C—H92C	108.88	C2A—C3A—H3A	119.86
C10C—C9C—H91C	109.07	C4A—C5A—H5A	121.22
C11C—C10C—H13C	108.97	C6A—C5A—H5A	121.31
C9C—C10C—H13C	108.95	C5A—C6A—H6A	118.41
H13C—C10C—H14C	109.43	C1A—C6A—H6A	118.43
C11C—C10C—H14C	109.12	C6B—C1B—C7B	117.87 (19)
C9C—C10C—H14C	109.10	C2B—C1B—C6B	118.99 (18)
H15C—C11C—H16C	109.48	C2B—C1B—C7B	123.14 (18)
C12C—C11C—H16C	108.91	N2B—C2B—C3B	119.37 (19)
C10C—C11C—H15C	108.56	N2B—C2B—C1B	122.21 (18)
C12C—C11C—H15C	108.76	C1B—C2B—C3B	118.40 (18)
C10C—C11C—H16C	108.71	C2B—C3B—C4B	119.61 (18)
C7C—C12C—H17C	109.24	N4B—C4B—C3B	117.87 (18)
H17C—C12C—H18C	109.38	N4B—C4B—C5B	118.79 (18)
C11C—C12C—H18C	109.18	C3B—C4B—C5B	123.34 (19)
C7C—C12C—H18C	109.25	C4B—C5B—C6B	116.68 (19)
C11C—C12C—H17C	109.36	C1B—C6B—C5B	123.0 (2)
C2D—C1D—C6D	110.35 (18)	O71B—C7B—O72B	124.0 (2)
N1D—C1D—C2D	108.40 (17)	O71B—C7B—C1B	117.6 (2)
N1D—C1D—C6D	113.55 (17)	O72B—C7B—C1B	118.4 (2)
C1D—C2D—C3D	110.68 (19)	C2B—C3B—H3B	120.25
C2D—C3D—C4D	111.8 (2)	C4B—C3B—H3B	120.14
C3D—C4D—C5D	111.2 (2)	C4B—C5B—H5B	121.66
C4D—C5D—C6D	111.3 (2)	C6B—C5B—H5B	121.66
C1D—C6D—C5D	108.89 (19)	C1B—C6B—H6B	118.55
C8D—C7D—C12D	111.05 (18)	C5B—C6B—H6B	118.48
C7C—N1C—C1C—C2C	173.10 (18)	C12D—C7D—C8D—C9D	55.0 (2)
C7C—N1C—C1C—C6C	49.8 (3)	N1D—C7D—C8D—C9D	176.64 (18)
C1C—N1C—C7C—C8C	60.0 (3)	N1D—C7D—C12D—C11D	−178.48 (18)
C1C—N1C—C7C—C12C	−177.14 (18)	C7D—C8D—C9D—C10D	−54.6 (3)
C1D—N1D—C7D—C12D	176.29 (18)	C8D—C9D—C10D—C11D	54.3 (3)
C1D—N1D—C7D—C8D	53.4 (2)	C9D—C10D—C11D—C12D	−55.0 (3)
C7D—N1D—C1D—C6D	49.3 (2)	C10D—C11D—C12D—C7D	55.6 (3)
C7D—N1D—C1D—C2D	172.26 (18)	C6A—C1A—C2A—N2A	−176.3 (2)
O42A—N4A—C4A—C5A	8.1 (3)	C2A—C1A—C7A—O71A	170.03 (19)
O42A—N4A—C4A—C3A	−172.2 (2)	C7A—C1A—C6A—C5A	177.1 (2)
O41A—N4A—C4A—C3A	7.0 (3)	C2A—C1A—C7A—O72A	−10.3 (3)
O41A—N4A—C4A—C5A	−172.7 (2)	C6A—C1A—C7A—O71A	−9.3 (3)
O42B—N4B—C4B—C3B	172.7 (2)	C2A—C1A—C6A—C5A	−2.3 (3)
O42B—N4B—C4B—C5B	−7.9 (3)	C6A—C1A—C2A—C3A	2.3 (3)
O41B—N4B—C4B—C5B	172.1 (2)	C7A—C1A—C2A—N2A	4.3 (3)
O41B—N4B—C4B—C3B	−7.3 (3)	C7A—C1A—C2A—C3A	−177.09 (19)
C2C—C1C—C6C—C5C	55.2 (3)	C6A—C1A—C7A—O72A	170.4 (2)
N1C—C1C—C6C—C5C	176.8 (2)	C1A—C2A—C3A—C4A	−1.0 (3)
C6C—C1C—C2C—C3C	−54.4 (3)	N2A—C2A—C3A—C4A	177.6 (2)
N1C—C1C—C2C—C3C	−178.49 (18)	C2A—C3A—C4A—C5A	−0.3 (3)
C1C—C2C—C3C—C4C	54.3 (3)	C2A—C3A—C4A—N4A	179.9 (4)
C2C—C3C—C4C—C5C	−55.7 (3)	C3A—C4A—C5A—C6A	0.4 (4)
C3C—C4C—C5C—C6C	57.3 (3)	N4A—C4A—C5A—C6A	−179.9 (2)
C4C—C5C—C6C—C1C	−57.0 (3)	C4A—C5A—C6A—C1A	1.0 (3)
N1C—C7C—C12C—C11C	179.9 (3)	C6B—C1B—C2B—N2B	−177.1 (2)
N1C—C7C—C8C—C9C	−179.82 (19)	C6B—C1B—C2B—C3B	1.3 (3)
C8C—C7C—C12C—C11C	−56.7 (3)	C2B—C1B—C7B—O71B	−170.91 (19)
C12C—C7C—C8C—C9C	58.2 (3)	C2B—C1B—C7B—O72B	9.9 (3)
C7C—C8C—C9C—C10C	−56.9 (3)	C6B—C1B—C7B—O71B	9.0 (3)
C8C—C9C—C10C—C11C	54.2 (4)	C6B—C1B—C7B—O72B	−170.2 (2)
C9C—C10C—C11C—C12C	−53.3 (3)	C7B—C1B—C2B—N2B	2.8 (3)
C10C—C11C—C12C—C7C	54.5 (3)	C7B—C1B—C2B—C3B	−178.81 (18)
C2D—C1D—C6D—C5D	60.1 (2)	C2B—C1B—C6B—C5B	−0.9 (3)
N1D—C1D—C6D—C5D	−178.02 (18)	C7B—C1B—C6B—C5B	179.2 (2)
N1D—C1D—C2D—C3D	177.36 (19)	N2B—C2B—C3B—C4B	177.9 (2)
C6D—C1D—C2D—C3D	−57.7 (2)	C1B—C2B—C3B—C4B	−0.5 (3)
C1D—C2D—C3D—C4D	53.9 (3)	C2B—C3B—C4B—N4B	178.63 (18)
C2D—C3D—C4D—C5D	−53.0 (3)	C2B—C3B—C4B—C5B	−0.7 (3)
C3D—C4D—C5D—C6D	56.1 (3)	C3B—C4B—C5B—C6B	1.2 (3)
C4D—C5D—C6D—C1D	−59.4 (3)	N4B—C4B—C5B—C6B	−178.20 (19)
C8D—C7D—C12D—C11D	−55.4 (2)	C4B—C5B—C6B—C1B	−0.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H21A···O72A	0.87 (3)	1.97 (3)	2.663 (3)	135 (2)
N2B—H21B···O72B	0.90 (2)	1.95 (3)	2.679 (3)	136 (2)
N1C—H11C···O72B	0.90 (2)	1.84 (2)	2.744 (3)	179 (2)
N1C—H12C···O71B^i	0.89 (2)	1.86 (2)	2.730 (3)	165 (2)
N1D—H12D···O72A^ii	0.92 (2)	1.88 (2)	2.765 (2)	160 (2)
N1D—H11D···O71A^iii	0.96 (3)	1.84 (3)	2.782 (2)	166 (2)
N2B—H22B···O71A^iii	0.91 (3)	2.30 (2)	3.166 (3)	161 (2)
N2A—H22A···O42B^iv	0.83 (3)	2.33 (3)	3.058 (3)	147 (2)
C6A—H6A···O71A	0.95	2.44	2.774 (3)	100
C6B—H6B···O71B	0.95	2.40	2.742 (3)	101

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