Triethylaminium picrate

Muthamizhchelvan, C.; Saminathan, K.; SethuSankar, K.; Fraanje, J.; Peschar, R.; Sivakumar, K.

doi:10.1107/S1600536805025870

Triethylaminium picrate

C. Muthamizhchelvan, K. Saminathan, K. SethuSankar, J. Fraanje, R. Peschar and K. Sivakumar

The title salt, C₆H₁₆N⁺·C₆H₂N₃O₇⁻, crystallizes with two pairs of cations and anions in the asymmetric unit. Anions A and B are stacked alternately in the (020) plane to form anionic columns having an ABABAB… sequence, with possible π–π interactions between them. The cationic columns surround these columns in an almost hexagonal fashion, with each column of the same type of cation, A or B. The anions and cations are connected through lone N—H

O and by other C—H

O hydrogen bonds. N—H

O and C—H

O hydrogen bonds involving A-and B- type ions form a cyclic pattern with a graph-set descriptor R₂²(10).

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025870/at6023sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025870/at6023Isup2.hkl Contains datablock I

CCDC reference: 283742

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.009 Å
R factor = 0.052
wR factor = 0.165
Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT223_ALERT_4_B Large Solvent/Anion  H     Ueq(max)/Ueq(min) ...       4.53 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        N1B

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.64
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT221_ALERT_4_C Large Solvent/Anion  C     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT231_ALERT_4_C Hirshfeld Test (Solvent)   C9A    -   C10A    ..       8.40 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N1A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N3A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N3B
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C9A
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for       C11A
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        N4A
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        N4B
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.87
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N4A    -   H4A    ...       1.01 Ang.
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N4B    -   H4B    ...       1.01 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H9B    ..  H11B    ..       1.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12E   ..  O7B     ..       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7A    ..  O5B     ..       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8C    ..  O5A     ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10A   ..  O6A     ..       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B   ..  O4B     ..       2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12A   ..  O6B     ..       2.62 Ang.

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           74.74
           From the CIF: _reflns_number_total               3363
           Count of symmetry unique reflns         3363
           Completeness (_total/calc)            100.00%
           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
   2 ALERT level B = Potentially serious problem
  24 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
  14 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1997); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Triethylaminium picrate top

Crystal data top

C₆H₁₆N⁺·C₆H₂N₃O₇⁻	F(000) = 1392
M_r = 330.30	D_x = 1.378 Mg m⁻³
Orthorhombic, Pca2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2c -2ac	Cell parameters from 25 reflections
a = 21.9799 (15) Å	θ = 15–50°
b = 6.9727 (4) Å	µ = 0.98 mm⁻¹
c = 20.7700 (13) Å	T = 293 K
V = 3183.2 (3) Å³	Pyramidal, yellow
Z = 8	0.5 × 0.4 × 0.3 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2403 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.057
Graphite monochromator	θ_max = 74.7°, θ_min = 4.0°
ω–2θ scans	h = −8→27
Absorption correction: ψ scan (North et al., 1968)	k = −3→8
T_min = 0.682, T_max = 0.745	l = −8→25
3634 measured reflections	2 standard reflections every 100 reflections
3363 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.165	w = 1/[σ²(F_o²) + (0.1004P)² + 0.2349P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3363 reflections	Δρ_max = 0.27 e Å⁻³
440 parameters	Δρ_min = −0.18 e Å⁻³
3 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0009 (2)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1A	0.27755 (14)	0.9469 (6)	0.40260 (17)	0.0799 (9)
O2A	0.3783 (2)	0.8759 (8)	0.4768 (2)	0.1118 (15)
O3A	0.44675 (19)	1.0764 (7)	0.4429 (2)	0.0972 (12)
O4A	0.50171 (18)	0.9438 (7)	0.2210 (2)	0.1016 (13)
O5A	0.4305 (2)	0.8915 (8)	0.15120 (19)	0.1101 (14)
O6A	0.2197 (2)	0.9545 (10)	0.2250 (3)	0.1254 (18)
O7A	0.20470 (17)	0.7831 (8)	0.3094 (3)	0.1168 (15)
N1A	0.40325 (19)	0.9697 (7)	0.4339 (2)	0.0727 (10)
N2A	0.4485 (2)	0.9209 (6)	0.2065 (2)	0.0790 (11)
N3A	0.2370 (2)	0.8766 (7)	0.2741 (2)	0.0809 (11)
C1A	0.31536 (17)	0.9291 (5)	0.3591 (2)	0.0552 (9)
C2A	0.38041 (18)	0.9473 (5)	0.3690 (2)	0.0554 (9)
C3A	0.42253 (18)	0.9504 (5)	0.3202 (2)	0.0569 (9)
C4A	0.4028 (2)	0.9259 (6)	0.2577 (2)	0.0615 (10)
C5A	0.3426 (2)	0.9042 (6)	0.2426 (2)	0.0622 (10)
C6A	0.30067 (18)	0.9031 (6)	0.2914 (2)	0.0576 (9)
N4A	0.17041 (19)	0.9221 (8)	0.4721 (2)	0.0895 (14)
C7A	0.1472 (3)	0.7256 (9)	0.4619 (3)	0.0944 (16)
H7A	0.1798	0.6353	0.4704	0.113*
H7B	0.1356	0.7115	0.4171	0.113*
C8A	0.0928 (4)	0.6739 (12)	0.5042 (4)	0.124 (3)
H8A	0.0803	0.5447	0.4952	0.186*
H8B	0.0598	0.7600	0.4953	0.186*
H8C	0.1041	0.6844	0.5487	0.186*
C9A	0.1930 (5)	0.981 (2)	0.5343 (4)	0.252 (11)
H9A	0.1611	0.9571	0.5656	0.302*
H9B	0.1994	1.1184	0.5329	0.302*
C10A	0.2494 (6)	0.892 (3)	0.5588 (5)	0.284 (12)
H10A	0.2565	0.9329	0.6022	0.426*
H10B	0.2831	0.9292	0.5322	0.426*
H10C	0.2453	0.7545	0.5579	0.426*
C11A	0.1246 (5)	1.0724 (11)	0.4570 (8)	0.163 (5)
H11A	0.0910	1.0613	0.4870	0.196*
H11B	0.1430	1.1975	0.4631	0.196*
C12A	0.1004 (4)	1.0600 (17)	0.3903 (10)	0.191 (7)
H12A	0.0710	1.1598	0.3836	0.287*
H12B	0.0814	0.9374	0.3840	0.287*
H12C	0.1332	1.0746	0.3601	0.287*
O1B	0.54679 (15)	0.5403 (6)	0.72140 (19)	0.0860 (10)
O2B	0.6359 (3)	0.6909 (11)	0.6415 (2)	0.146 (2)
O3B	0.7158 (3)	0.5304 (12)	0.6599 (3)	0.147 (2)
O4B	0.78537 (14)	0.6353 (6)	0.8795 (2)	0.0921 (11)
O5B	0.72258 (18)	0.5833 (8)	0.9564 (2)	0.1003 (13)
O6B	0.5116 (2)	0.4255 (8)	0.9027 (3)	0.1154 (16)
O7B	0.47849 (17)	0.6244 (9)	0.8318 (3)	0.1257 (18)
N1B	0.6679 (2)	0.6027 (7)	0.6778 (2)	0.0826 (12)
N2B	0.73400 (17)	0.6036 (6)	0.8994 (2)	0.0708 (10)
N3B	0.51909 (17)	0.5309 (7)	0.8561 (3)	0.0842 (13)
C1B	0.58816 (19)	0.5621 (6)	0.7620 (2)	0.0597 (9)
C6B	0.58025 (17)	0.5511 (6)	0.8303 (2)	0.0599 (10)
C5B	0.62663 (19)	0.5578 (6)	0.8749 (2)	0.0587 (10)
C4B	0.68484 (17)	0.5855 (6)	0.8535 (2)	0.0564 (9)
C3B	0.69780 (19)	0.6014 (6)	0.7880 (2)	0.0598 (10)
C2B	0.65117 (19)	0.5894 (6)	0.7451 (2)	0.0584 (9)
N4B	0.43620 (15)	0.5500 (6)	0.65648 (18)	0.0671 (10)
C7B	0.4329 (3)	0.3752 (9)	0.6143 (3)	0.0932 (17)
H7C	0.4344	0.2614	0.6411	0.112*
H7D	0.4680	0.3729	0.5861	0.112*
C8B	0.3746 (4)	0.3706 (14)	0.5734 (4)	0.131 (3)
H8D	0.3746	0.2577	0.5469	0.196*
H8E	0.3731	0.4825	0.5465	0.196*
H8F	0.3397	0.3686	0.6012	0.196*
C9B	0.4404 (2)	0.7359 (9)	0.6186 (3)	0.0889 (15)
H9C	0.4031	0.7521	0.5944	0.107*
H9D	0.4432	0.8415	0.6489	0.107*
C10B	0.4921 (3)	0.7482 (14)	0.5738 (4)	0.120 (2)
H10D	0.4912	0.8697	0.5521	0.180*
H10E	0.4893	0.6466	0.5427	0.180*
H10F	0.5295	0.7363	0.5974	0.180*
C11B	0.3868 (2)	0.5622 (9)	0.7058 (3)	0.0862 (16)
H11C	0.3951	0.6697	0.7341	0.103*
H11D	0.3485	0.5872	0.6842	0.103*
C12B	0.3806 (3)	0.3875 (13)	0.7449 (4)	0.113 (2)
H12D	0.3490	0.4055	0.7762	0.170*
H12E	0.4183	0.3616	0.7666	0.170*
H12F	0.3704	0.2813	0.7176	0.170*
H3A	0.468 (3)	0.960 (8)	0.324 (3)	0.095 (18)*
H5A	0.3294 (19)	0.873 (6)	0.199 (2)	0.055 (11)*
H4A	0.209 (3)	0.918 (9)	0.446 (3)	0.094 (18)*
H3B	0.617 (2)	0.537 (7)	0.918 (2)	0.061 (12)*
H5B	0.737 (3)	0.630 (8)	0.768 (3)	0.083 (16)*
H4B	0.476 (3)	0.514 (11)	0.678 (4)	0.13 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0612 (17)	0.109 (3)	0.0691 (19)	0.0074 (16)	0.0189 (15)	−0.0032 (19)
O2A	0.098 (3)	0.166 (4)	0.072 (2)	0.004 (3)	0.001 (2)	0.035 (3)
O3A	0.085 (2)	0.120 (3)	0.087 (3)	−0.015 (2)	−0.022 (2)	−0.002 (2)
O4A	0.069 (2)	0.127 (4)	0.108 (3)	0.000 (2)	0.034 (2)	0.005 (3)
O5A	0.121 (3)	0.145 (4)	0.065 (2)	0.020 (3)	0.031 (2)	−0.003 (2)
O6A	0.087 (3)	0.193 (5)	0.096 (3)	0.013 (3)	−0.024 (2)	0.008 (3)
O7A	0.068 (2)	0.155 (4)	0.127 (3)	−0.037 (2)	0.001 (2)	0.012 (3)
N1A	0.062 (2)	0.091 (3)	0.065 (2)	0.0123 (19)	−0.0019 (17)	0.009 (2)
N2A	0.084 (3)	0.082 (3)	0.071 (3)	0.008 (2)	0.026 (2)	0.005 (2)
N3A	0.069 (2)	0.093 (3)	0.080 (3)	−0.002 (2)	−0.005 (2)	−0.009 (2)
C1A	0.0514 (19)	0.050 (2)	0.064 (2)	0.0033 (15)	0.0049 (17)	0.0018 (17)
C2A	0.0522 (19)	0.053 (2)	0.061 (2)	0.0035 (15)	0.0042 (16)	0.0043 (18)
C3A	0.0495 (19)	0.054 (2)	0.067 (2)	0.0057 (15)	0.0105 (18)	0.0013 (18)
C4A	0.069 (2)	0.052 (2)	0.064 (2)	0.0063 (17)	0.016 (2)	0.0039 (18)
C5A	0.073 (3)	0.056 (2)	0.058 (2)	0.0047 (19)	0.004 (2)	−0.0027 (19)
C6A	0.0535 (19)	0.054 (2)	0.065 (2)	0.0014 (16)	0.0031 (17)	−0.0051 (19)
N4A	0.061 (2)	0.127 (4)	0.080 (3)	−0.011 (2)	0.025 (2)	−0.021 (3)
C7A	0.102 (4)	0.091 (4)	0.090 (3)	0.016 (3)	0.020 (3)	0.006 (3)
C8A	0.140 (6)	0.112 (5)	0.120 (5)	−0.035 (4)	0.028 (5)	0.011 (4)
C9A	0.181 (11)	0.46 (3)	0.115 (7)	−0.177 (15)	0.082 (8)	−0.124 (12)
C10A	0.136 (9)	0.63 (4)	0.087 (6)	−0.020 (16)	0.018 (6)	0.053 (12)
C11A	0.127 (7)	0.079 (4)	0.284 (15)	−0.011 (4)	0.125 (9)	−0.016 (6)
C12A	0.081 (5)	0.154 (9)	0.34 (2)	0.017 (5)	0.008 (8)	0.094 (12)
O1B	0.0656 (18)	0.103 (3)	0.090 (2)	−0.0009 (17)	−0.0277 (18)	0.002 (2)
O2B	0.141 (4)	0.218 (7)	0.081 (3)	0.011 (4)	−0.008 (3)	0.045 (4)
O3B	0.128 (4)	0.225 (7)	0.087 (3)	0.025 (4)	0.024 (3)	−0.002 (4)
O4B	0.0517 (17)	0.121 (3)	0.103 (3)	−0.0057 (17)	−0.0094 (17)	−0.014 (2)
O5B	0.082 (2)	0.147 (4)	0.072 (2)	0.001 (2)	−0.0132 (18)	0.003 (2)
O6B	0.087 (3)	0.135 (4)	0.125 (4)	−0.016 (2)	0.030 (3)	0.017 (3)
O7B	0.0568 (19)	0.170 (4)	0.150 (4)	0.023 (2)	−0.005 (2)	−0.012 (4)
N1B	0.085 (3)	0.097 (3)	0.066 (2)	−0.002 (2)	−0.004 (2)	0.000 (2)
N2B	0.064 (2)	0.074 (2)	0.074 (3)	0.0040 (17)	−0.0172 (19)	−0.007 (2)
N3B	0.052 (2)	0.094 (3)	0.106 (3)	−0.004 (2)	0.001 (2)	−0.016 (3)
C1B	0.056 (2)	0.052 (2)	0.071 (2)	0.0059 (16)	−0.0130 (18)	−0.0016 (19)
C6B	0.0483 (18)	0.054 (2)	0.077 (3)	0.0035 (15)	−0.0006 (18)	0.001 (2)
C5B	0.059 (2)	0.054 (2)	0.064 (2)	−0.0014 (16)	−0.0027 (18)	0.0037 (19)
C4B	0.0489 (18)	0.050 (2)	0.071 (2)	0.0039 (15)	−0.0075 (17)	−0.0014 (17)
C3B	0.054 (2)	0.054 (2)	0.071 (3)	−0.0009 (17)	−0.0029 (19)	−0.0013 (19)
C2B	0.059 (2)	0.052 (2)	0.064 (2)	0.0016 (16)	−0.0046 (18)	0.0019 (18)
N4B	0.0489 (16)	0.097 (3)	0.0549 (18)	0.0111 (17)	−0.0060 (14)	−0.0012 (19)
C7B	0.099 (4)	0.103 (4)	0.078 (3)	0.033 (3)	−0.005 (3)	−0.007 (3)
C8B	0.146 (7)	0.146 (7)	0.100 (5)	−0.005 (5)	−0.029 (5)	−0.046 (5)
C9B	0.086 (3)	0.094 (4)	0.087 (3)	0.008 (3)	−0.015 (3)	−0.002 (3)
C10B	0.085 (4)	0.169 (7)	0.107 (4)	−0.022 (4)	−0.013 (3)	0.047 (5)
C11B	0.062 (2)	0.124 (5)	0.072 (3)	0.013 (3)	0.002 (2)	−0.010 (3)
C12B	0.081 (4)	0.162 (7)	0.096 (4)	−0.005 (4)	0.015 (3)	0.021 (4)

Geometric parameters (Å, º) top

O1A—C1A	1.234 (5)	O1B—C1B	1.250 (5)
O2A—N1A	1.233 (6)	O2B—N1B	1.200 (7)
O3A—N1A	1.226 (6)	O3B—N1B	1.227 (7)
O4A—N2A	1.219 (6)	O4B—N2B	1.222 (5)
O5A—N2A	1.232 (6)	O5B—N2B	1.218 (6)
O6A—N3A	1.217 (7)	O6B—N3B	1.226 (7)
O7A—N3A	1.210 (6)	O7B—N3B	1.215 (7)
N1A—C2A	1.447 (6)	N1B—C2B	1.447 (7)
N2A—C4A	1.463 (6)	N2B—C4B	1.447 (5)
N3A—C6A	1.457 (6)	N3B—C6B	1.454 (6)
C1A—C2A	1.450 (5)	C1B—C6B	1.431 (7)
C1A—C6A	1.454 (6)	C1B—C2B	1.441 (6)
C2A—C3A	1.373 (6)	C6B—C5B	1.379 (6)
C3A—C4A	1.378 (7)	C5B—C4B	1.369 (6)
C3A—H3A	1.00 (6)	C5B—H3B	0.93 (5)
C4A—C5A	1.368 (7)	C4B—C3B	1.393 (6)
C5A—C6A	1.371 (6)	C3B—C2B	1.362 (6)
C5A—H5A	0.97 (5)	C3B—H5B	0.97 (6)
N4A—C9A	1.444 (8)	N4B—C11B	1.495 (6)
N4A—C7A	1.477 (8)	N4B—C7B	1.502 (7)
N4A—C11A	1.487 (13)	N4B—C9B	1.519 (7)
N4A—H4A	1.01 (7)	N4B—H4B	1.00 (8)
C7A—C8A	1.526 (9)	C7B—C8B	1.539 (9)
C7A—H7A	0.9700	C7B—H7C	0.9700
C7A—H7B	0.9700	C7B—H7D	0.9700
C8A—H8A	0.9600	C8B—H8D	0.9600
C8A—H8B	0.9600	C8B—H8E	0.9600
C8A—H8C	0.9600	C8B—H8F	0.9600
C9A—C10A	1.479 (10)	C9B—C10B	1.471 (9)
C9A—H9A	0.9700	C9B—H9C	0.9700
C9A—H9B	0.9700	C9B—H9D	0.9700
C10A—H10A	0.9600	C10B—H10D	0.9600
C10A—H10B	0.9600	C10B—H10E	0.9600
C10A—H10C	0.9600	C10B—H10F	0.9600
C11A—C12A	1.49 (2)	C11B—C12B	1.470 (10)
C11A—H11A	0.9700	C11B—H11C	0.9700
C11A—H11B	0.9700	C11B—H11D	0.9700
C12A—H12A	0.9600	C12B—H12D	0.9600
C12A—H12B	0.9600	C12B—H12E	0.9600
C12A—H12C	0.9600	C12B—H12F	0.9600

O3A—N1A—O2A	123.9 (5)	O2B—N1B—O3B	121.5 (6)
O3A—N1A—C2A	118.6 (4)	O2B—N1B—C2B	119.4 (5)
O2A—N1A—C2A	117.5 (4)	O3B—N1B—C2B	119.0 (5)
O4A—N2A—O5A	124.0 (4)	O5B—N2B—O4B	122.7 (4)
O4A—N2A—C4A	118.4 (5)	O5B—N2B—C4B	118.4 (4)
O5A—N2A—C4A	117.6 (5)	O4B—N2B—C4B	118.9 (4)
O7A—N3A—O6A	124.4 (5)	O7B—N3B—O6B	123.4 (5)
O7A—N3A—C6A	118.9 (5)	O7B—N3B—C6B	118.3 (6)
O6A—N3A—C6A	116.8 (5)	O6B—N3B—C6B	118.2 (5)
O1A—C1A—C2A	123.5 (4)	O1B—C1B—C6B	125.0 (4)
O1A—C1A—C6A	124.8 (4)	O1B—C1B—C2B	123.4 (4)
C2A—C1A—C6A	111.5 (3)	C6B—C1B—C2B	111.5 (3)
C3A—C2A—N1A	116.9 (4)	C5B—C6B—C1B	125.1 (4)
C3A—C2A—C1A	124.2 (4)	C5B—C6B—N3B	116.1 (4)
N1A—C2A—C1A	118.9 (4)	C1B—C6B—N3B	118.9 (4)
C2A—C3A—C4A	118.7 (4)	C4B—C5B—C6B	118.5 (4)
C2A—C3A—H3A	127 (4)	C4B—C5B—H3B	123 (3)
C4A—C3A—H3A	114 (4)	C6B—C5B—H3B	118 (3)
C5A—C4A—C3A	122.3 (4)	C5B—C4B—C3B	121.4 (4)
C5A—C4A—N2A	119.6 (4)	C5B—C4B—N2B	119.7 (4)
C3A—C4A—N2A	118.1 (4)	C3B—C4B—N2B	118.9 (4)
C4A—C5A—C6A	118.7 (4)	C2B—C3B—C4B	118.7 (4)
C4A—C5A—H5A	122 (3)	C2B—C3B—H5B	113 (4)
C6A—C5A—H5A	119 (3)	C4B—C3B—H5B	128 (4)
C5A—C6A—C1A	124.4 (4)	C3B—C2B—C1B	124.8 (4)
C5A—C6A—N3A	117.7 (4)	C3B—C2B—N1B	116.0 (4)
C1A—C6A—N3A	117.8 (4)	C1B—C2B—N1B	119.2 (4)
C9A—N4A—C7A	120.6 (8)	C11B—N4B—C7B	114.3 (4)
C9A—N4A—C11A	102.8 (9)	C11B—N4B—C9B	110.5 (4)
C7A—N4A—C11A	112.9 (5)	C7B—N4B—C9B	113.2 (4)
C9A—N4A—H4A	102 (4)	C11B—N4B—H4B	110 (5)
C7A—N4A—H4A	101 (3)	C7B—N4B—H4B	96 (5)
C11A—N4A—H4A	118 (4)	C9B—N4B—H4B	113 (5)
N4A—C7A—C8A	114.0 (5)	N4B—C7B—C8B	112.3 (5)
N4A—C7A—H7A	108.7	N4B—C7B—H7C	109.1
C8A—C7A—H7A	108.7	C8B—C7B—H7C	109.1
N4A—C7A—H7B	108.7	N4B—C7B—H7D	109.1
C8A—C7A—H7B	108.7	C8B—C7B—H7D	109.1
H7A—C7A—H7B	107.6	H7C—C7B—H7D	107.9
C7A—C8A—H8A	109.5	C7B—C8B—H8D	109.5
C7A—C8A—H8B	109.5	C7B—C8B—H8E	109.5
H8A—C8A—H8B	109.5	H8D—C8B—H8E	109.5
C7A—C8A—H8C	109.5	C7B—C8B—H8F	109.5
H8A—C8A—H8C	109.5	H8D—C8B—H8F	109.5
H8B—C8A—H8C	109.5	H8E—C8B—H8F	109.5
N4A—C9A—C10A	118.5 (10)	C10B—C9B—N4B	115.1 (5)
N4A—C9A—H9A	107.7	C10B—C9B—H9C	108.5
C10A—C9A—H9A	107.7	N4B—C9B—H9C	108.5
N4A—C9A—H9B	107.7	C10B—C9B—H9D	108.5
C10A—C9A—H9B	107.7	N4B—C9B—H9D	108.5
H9A—C9A—H9B	107.1	H9C—C9B—H9D	107.5
C9A—C10A—H10A	109.5	C9B—C10B—H10D	109.5
C9A—C10A—H10B	109.5	C9B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
C9A—C10A—H10C	109.5	C9B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
C12A—C11A—N4A	113.4 (8)	C12B—C11B—N4B	113.5 (5)
C12A—C11A—H11A	108.9	C12B—C11B—H11C	108.9
N4A—C11A—H11A	108.9	N4B—C11B—H11C	108.9
C12A—C11A—H11B	108.9	C12B—C11B—H11D	108.9
N4A—C11A—H11B	108.9	N4B—C11B—H11D	108.9
H11A—C11A—H11B	107.7	H11C—C11B—H11D	107.7
C11A—C12A—H12A	109.5	C11B—C12B—H12D	109.5
C11A—C12A—H12B	109.5	C11B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C11A—C12A—H12C	109.5	C11B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5

O3A—N1A—C2A—C3A	35.3 (6)	O1B—C1B—C6B—C5B	173.8 (4)
O2A—N1A—C2A—C3A	−143.1 (4)	C2B—C1B—C6B—C5B	−2.4 (6)
O3A—N1A—C2A—C1A	−142.8 (4)	O1B—C1B—C6B—N3B	−6.1 (7)
O2A—N1A—C2A—C1A	38.8 (6)	C2B—C1B—C6B—N3B	177.7 (4)
O1A—C1A—C2A—C3A	−172.0 (4)	O7B—N3B—C6B—C5B	138.8 (5)
C6A—C1A—C2A—C3A	3.4 (5)	O6B—N3B—C6B—C5B	−38.6 (7)
O1A—C1A—C2A—N1A	6.0 (6)	O7B—N3B—C6B—C1B	−41.3 (7)
C6A—C1A—C2A—N1A	−178.6 (4)	O6B—N3B—C6B—C1B	141.3 (5)
N1A—C2A—C3A—C4A	178.8 (4)	C1B—C6B—C5B—C4B	3.0 (6)
C1A—C2A—C3A—C4A	−3.2 (6)	N3B—C6B—C5B—C4B	−177.1 (4)
C2A—C3A—C4A—C5A	1.9 (6)	C6B—C5B—C4B—C3B	−1.8 (6)
C2A—C3A—C4A—N2A	−177.3 (4)	C6B—C5B—C4B—N2B	176.6 (4)
O4A—N2A—C4A—C5A	178.8 (4)	O5B—N2B—C4B—C5B	3.9 (7)
O5A—N2A—C4A—C5A	−2.0 (7)	O4B—N2B—C4B—C5B	−177.4 (4)
O4A—N2A—C4A—C3A	−2.0 (6)	O5B—N2B—C4B—C3B	−177.7 (4)
O5A—N2A—C4A—C3A	177.3 (5)	O4B—N2B—C4B—C3B	1.1 (6)
C3A—C4A—C5A—C6A	−1.3 (6)	C5B—C4B—C3B—C2B	0.2 (6)
N2A—C4A—C5A—C6A	177.9 (4)	N2B—C4B—C3B—C2B	−178.2 (4)
C4A—C5A—C6A—C1A	1.8 (7)	C4B—C3B—C2B—C1B	0.4 (7)
C4A—C5A—C6A—N3A	−179.0 (4)	C4B—C3B—C2B—N1B	−178.7 (4)
O1A—C1A—C6A—C5A	172.6 (4)	O1B—C1B—C2B—C3B	−175.6 (4)
C2A—C1A—C6A—C5A	−2.7 (6)	C6B—C1B—C2B—C3B	0.7 (6)
O1A—C1A—C6A—N3A	−6.6 (6)	O1B—C1B—C2B—N1B	3.4 (6)
C2A—C1A—C6A—N3A	178.1 (4)	C6B—C1B—C2B—N1B	179.6 (4)
O7A—N3A—C6A—C5A	143.2 (5)	O2B—N1B—C2B—C3B	−140.7 (6)
O6A—N3A—C6A—C5A	−38.2 (7)	O3B—N1B—C2B—C3B	36.1 (8)
O7A—N3A—C6A—C1A	−37.6 (7)	O2B—N1B—C2B—C1B	40.3 (7)
O6A—N3A—C6A—C1A	141.1 (5)	O3B—N1B—C2B—C1B	−142.9 (6)
C9A—N4A—C7A—C8A	60.5 (9)	C11B—N4B—C7B—C8B	63.2 (7)
C11A—N4A—C7A—C8A	−61.5 (9)	C9B—N4B—C7B—C8B	−64.5 (7)
C7A—N4A—C9A—C10A	67.1 (11)	C11B—N4B—C9B—C10B	173.2 (5)
C11A—N4A—C9A—C10A	−166.1 (11)	C7B—N4B—C9B—C10B	−57.1 (6)
C9A—N4A—C11A—C12A	171.9 (7)	C7B—N4B—C11B—C12B	51.7 (6)
C7A—N4A—C11A—C12A	−56.6 (8)	C9B—N4B—C11B—C12B	−179.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H4A···O1A	1.01 (7)	1.76 (7)	2.767 (5)	172 (5)
N4B—H4B···O1B	1.00 (8)	1.82 (8)	2.781 (5)	160 (7)
C10A—H10B···O2A	0.96	2.42	3.307 (13)	154
C10B—H10F···O2B	0.96	2.53	3.483 (9)	170
C12B—H12E···O7B	0.96	2.64	3.258 (10)	123
C7A—H7A···O5Bⁱ	0.97	2.65	3.584 (7)	162
C8A—H8C···O5Aⁱⁱ	0.96	2.68	3.448 (10)	137
C10A—H10A···O6Aⁱⁱ	0.96	2.61	3.547 (14)	166
C11A—H11B···O4Bⁱⁱⁱ	0.97	2.62	3.265 (9)	124
C12A—H12A···O6B^iv	0.96	2.62	3.553 (11)	163
C7B—H7C···O4A^v	0.97	2.60	3.454 (7)	147
C9B—H9D···O4A^vi	0.97	2.44	3.336 (8)	154
C12B—H12D···O4B^vii	0.96	2.58	3.496 (8)	160

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

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