l-Histidinium trichloro­acetate

Gokul Raj, S.; Kumar, G.R.; Mohan, R.; Jayavel, R.; Varghese, B.

doi:10.1107/S1600536806011342

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L-Histidinium trichloroacetate

S. Gokul Raj, G. R. Kumar, R. Mohan, R. Jayavel and B. Varghese

The title compound, C₆H₁₀N₃O₂⁺·C₂Cl₃O₂⁻, crystallizes with two histidinium cations and two trichloroacetate anions in the asymmetric unit. The cations and anions are linked through a number of intermolecular N—H

O hydrogen bonds, forming a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011342/wn2004sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011342/wn2004Isup2.hkl Contains datablock I

CCDC reference: 267511

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R factor = 0.039
wR factor = 0.109
Data-to-parameter ratio = 5.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............      24.98 Deg.
PLAT089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) .....       5.39
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         80 PerFit
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         93 PerFit

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.87
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.10
PLAT301_ALERT_3_C Main Residue  Disorder .........................      14.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl4    ..  O7      ..       3.17 Ang.
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.25 Ratio
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      32.50 Deg.
              CL3  -C7   -CL3'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      21.00 Deg.
              CL2' -C7   -CL2     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      20.10 Deg.
              CL1  -C7   -CL1'    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.50 Deg.
              CL5' -C15  -CL5     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      26.90 Deg.
              CL4  -C15  -CL4'    1.555   1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C2 Cl2.99 O2

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.865
            Tmax scaled      0.864 Tmin scaled      0.760
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           24.98
           From the CIF: _reflns_number_total               2300
           Count of symmetry unique reflns         2302
           Completeness (_total/calc)             99.91%
           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        yes

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

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

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1988); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995) in WinGX (Farrugia, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1993) in WinGX; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

L-histidinium trichloroacetate top

Crystal data top

C₆H₁₀N₃O₂⁺·C₂Cl₃O₂⁻	F(000) = 648
M_r = 318.54	D_x = 1.661 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 5.4505 (18) Å	Cell parameters from 25 reflections
b = 25.769 (8) Å	θ = 10–14°
c = 9.210 (2) Å	µ = 0.73 mm⁻¹
β = 99.98 (2)°	T = 293 K
V = 1274.0 (7) Å³	Cut from a needle, colourless
Z = 4	0.3 × 0.3 × 0.2 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2155 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 25.0°, θ_min = 2.3°
ω–2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = 0→30
T_min = 0.879, T_max = 0.999	l = −10→10
2539 measured reflections	2 standard reflections every 60 min
2300 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.0685P)² + 0.5935P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.109	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.36 e Å⁻³
2300 reflections	Δρ_min = −0.29 e Å⁻³
427 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
263 restraints	Extinction coefficient: 0.080 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 253 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.21 (11)

Special details top

Experimental. Number of psi-scan sets used was 4 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

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	Occ. (<1)
C1	0.7823 (11)	−0.1583 (2)	0.6214 (6)	0.0471 (12)
C2	1.0290 (9)	−0.14907 (19)	0.4615 (6)	0.0412 (11)
C3	0.8872 (8)	−0.10619 (18)	0.4528 (5)	0.0305 (9)
C4	0.8736 (8)	−0.06109 (17)	0.3510 (5)	0.0316 (9)
H4A	0.7501	−0.0687	0.2645	0.038*
H4B	1.0332	−0.0577	0.3189	0.038*
C5	0.8087 (7)	−0.00863 (15)	0.4134 (4)	0.0261 (8)
H6	0.8933	−0.0058	0.5161	0.031*
C6	0.5258 (7)	−0.00231 (17)	0.4078 (4)	0.0287 (8)
C7	0.2809 (10)	−0.1625 (2)	0.0293 (6)	0.0471 (12)
C8	0.4055 (8)	−0.16412 (18)	−0.1124 (5)	0.0338 (9)
C9	0.2924 (12)	0.1685 (2)	1.1207 (7)	0.0536 (14)
C10	0.5306 (9)	0.1619 (2)	0.9564 (6)	0.0411 (11)
C11	0.3932 (8)	0.11810 (19)	0.9482 (5)	0.0329 (9)
C12	0.3634 (9)	0.07396 (18)	0.8430 (5)	0.0365 (10)
H12A	0.4445	0.0831	0.7607	0.044*
H12B	0.1872	0.0698	0.8045	0.044*
C13	0.4668 (7)	0.02098 (16)	0.9041 (4)	0.0272 (8)
H13	0.4279	0.0157	1.0030	0.033*
C14	0.7510 (7)	0.01860 (18)	0.9104 (4)	0.0307 (9)
C15	0.7900 (13)	0.1784 (2)	0.5299 (7)	0.0550 (14)
C16	0.9018 (9)	0.17816 (18)	0.3840 (6)	0.0360 (10)
N1	0.9597 (8)	−0.18083 (14)	0.5669 (5)	0.0409 (9)
N2	0.7307 (8)	−0.11348 (16)	0.5541 (5)	0.0436 (10)
N3	0.9037 (6)	0.03239 (14)	0.3254 (4)	0.0276 (7)
H3A	1.0678	0.0289	0.3321	0.033*
H3B	0.8698	0.0634	0.3596	0.033*
H3C	0.8308	0.0295	0.2315	0.033*
N4	0.2435 (8)	0.12337 (17)	1.0513 (5)	0.0464 (11)
N5	0.4653 (8)	0.19219 (13)	1.0648 (5)	0.0423 (10)
N6	0.3388 (6)	−0.01904 (14)	0.8022 (4)	0.0283 (7)
H6A	0.3858	−0.0160	0.7147	0.057 (17)*
H6B	0.1747	−0.0147	0.7919	0.053 (16)*
H6C	0.3793	−0.0504	0.8389	0.027 (9)*
O1	0.4122 (6)	0.02412 (17)	0.3066 (4)	0.0498 (9)
O2	0.4336 (5)	−0.02631 (14)	0.5038 (3)	0.0363 (7)
O3	0.4619 (7)	−0.20731 (13)	−0.1501 (4)	0.0426 (8)
O4	0.4347 (9)	−0.12222 (15)	−0.1705 (5)	0.0611 (12)
O5	0.8256 (5)	−0.00107 (17)	0.8040 (4)	0.0482 (9)
O6	0.8793 (6)	0.03907 (17)	1.0212 (4)	0.0472 (9)
O7	0.9625 (8)	0.22106 (14)	0.3431 (4)	0.0485 (9)
O8	0.9148 (9)	0.13640 (16)	0.3250 (5)	0.0622 (12)
Cl1	0.0142 (14)	−0.1941 (9)	0.0094 (10)	0.076 (3)	0.47 (3)
Cl1'	0.058 (2)	−0.2174 (5)	0.0135 (11)	0.069 (2)	0.52 (3)
Cl2	0.5056 (8)	−0.1878 (6)	0.1829 (5)	0.0790 (19)	0.75 (3)
Cl2'	0.473 (4)	−0.1629 (13)	0.1795 (16)	0.069 (6)	0.25 (3)
Cl3'	0.250 (3)	−0.0970 (2)	0.0904 (8)	0.088 (3)	0.51 (2)
Cl3	0.090 (3)	−0.1077 (3)	0.0287 (16)	0.102 (4)	0.49 (2)
Cl4'	0.5827 (15)	0.2359 (3)	0.5189 (9)	0.080 (2)	0.401 (16)
Cl4	0.5155 (9)	0.2064 (4)	0.5132 (5)	0.085 (3)	0.579 (16)
Cl5	1.0098 (6)	0.2116 (2)	0.6769 (3)	0.0731 (13)	0.629 (13)
Cl5'	0.9769 (13)	0.1746 (6)	0.6735 (6)	0.095 (4)	0.353 (13)
Cl6'	0.7904 (7)	0.11324 (12)	0.6080 (3)	0.0759 (13)	0.621 (7)
Cl6	0.5457 (12)	0.1272 (2)	0.5035 (7)	0.099 (3)	0.416 (8)
H1'	0.696 (9)	−0.177 (2)	0.681 (5)	0.052 (15)*
H1	1.019 (14)	−0.2105 (14)	0.594 (9)	0.09 (3)*
H2'	1.144 (7)	−0.158 (2)	0.404 (4)	0.038 (13)*
H2	0.637 (8)	−0.0887 (14)	0.571 (5)	0.039 (14)*
H4	0.205 (18)	0.099 (2)	1.107 (8)	0.08 (3)*
H5	0.510 (9)	0.2227 (8)	1.094 (5)	0.033 (13)*
H9	0.231 (11)	0.178 (2)	1.204 (4)	0.055 (16)*
H10	0.647 (8)	0.172 (3)	0.901 (5)	0.052 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.062 (3)	0.037 (3)	0.049 (3)	0.008 (2)	0.030 (2)	0.010 (2)
C2	0.045 (3)	0.031 (2)	0.053 (3)	0.005 (2)	0.025 (2)	0.004 (2)
C3	0.034 (2)	0.025 (2)	0.034 (2)	0.0008 (17)	0.0108 (17)	0.0017 (18)
C4	0.033 (2)	0.027 (2)	0.038 (2)	0.0012 (16)	0.0143 (18)	0.0016 (17)
C5	0.0220 (17)	0.028 (2)	0.0294 (18)	0.0008 (15)	0.0065 (14)	0.0003 (15)
C6	0.0205 (17)	0.0287 (18)	0.037 (2)	−0.0004 (15)	0.0063 (15)	−0.0026 (16)
C7	0.054 (3)	0.043 (3)	0.052 (3)	0.003 (2)	0.028 (2)	0.001 (2)
C8	0.030 (2)	0.028 (2)	0.046 (2)	0.0012 (18)	0.0141 (18)	0.006 (2)
C9	0.067 (3)	0.046 (3)	0.056 (3)	−0.004 (3)	0.033 (3)	−0.011 (2)
C10	0.043 (3)	0.034 (3)	0.052 (3)	−0.009 (2)	0.024 (2)	−0.004 (2)
C11	0.029 (2)	0.029 (2)	0.043 (2)	0.0020 (17)	0.0124 (17)	0.0027 (19)
C12	0.038 (2)	0.028 (2)	0.043 (3)	0.0014 (18)	0.0061 (19)	−0.0013 (19)
C13	0.0248 (18)	0.0252 (18)	0.0321 (19)	−0.0029 (15)	0.0065 (15)	−0.0010 (15)
C14	0.0228 (18)	0.037 (2)	0.033 (2)	−0.0031 (16)	0.0058 (15)	0.0018 (17)
C15	0.066 (4)	0.044 (3)	0.063 (3)	−0.006 (3)	0.034 (3)	−0.002 (3)
C16	0.040 (2)	0.025 (2)	0.045 (2)	−0.0008 (18)	0.013 (2)	0.0045 (19)
N1	0.049 (2)	0.0262 (19)	0.051 (2)	0.0047 (17)	0.0191 (19)	0.0097 (18)
N2	0.050 (2)	0.037 (2)	0.052 (2)	0.0124 (18)	0.031 (2)	0.0079 (19)
N3	0.0205 (15)	0.0268 (17)	0.0355 (18)	−0.0009 (13)	0.0048 (13)	0.0028 (14)
N4	0.050 (2)	0.034 (2)	0.062 (3)	−0.0082 (18)	0.029 (2)	−0.001 (2)
N5	0.053 (2)	0.024 (2)	0.052 (2)	−0.0056 (17)	0.017 (2)	−0.0060 (18)
N6	0.0221 (15)	0.0248 (17)	0.0389 (19)	−0.0007 (13)	0.0074 (13)	−0.0010 (14)
O1	0.0217 (14)	0.064 (2)	0.064 (2)	0.0049 (15)	0.0078 (13)	0.0287 (18)
O2	0.0285 (14)	0.0451 (18)	0.0378 (16)	0.0006 (13)	0.0127 (12)	0.0044 (13)
O3	0.056 (2)	0.0255 (17)	0.051 (2)	0.0033 (15)	0.0218 (16)	0.0023 (14)
O4	0.090 (3)	0.0276 (19)	0.079 (3)	0.0097 (18)	0.052 (2)	0.0069 (17)
O5	0.0235 (14)	0.072 (2)	0.0512 (19)	−0.0012 (15)	0.0105 (13)	−0.0173 (17)
O6	0.0338 (16)	0.067 (2)	0.0407 (18)	−0.0186 (16)	0.0071 (14)	−0.0087 (16)
O7	0.069 (2)	0.0279 (18)	0.054 (2)	−0.0077 (15)	0.0253 (18)	−0.0013 (15)
O8	0.097 (3)	0.028 (2)	0.074 (3)	−0.0065 (19)	0.050 (2)	−0.0048 (17)
Cl1	0.035 (2)	0.108 (8)	0.086 (3)	−0.018 (3)	0.0171 (18)	0.013 (4)
Cl1'	0.052 (3)	0.067 (4)	0.099 (3)	−0.022 (3)	0.039 (2)	−0.006 (3)
Cl2	0.0671 (18)	0.125 (5)	0.0430 (14)	0.016 (2)	0.0042 (10)	0.010 (2)
Cl2'	0.052 (6)	0.105 (11)	0.047 (4)	−0.026 (6)	0.004 (4)	−0.009 (5)
Cl3'	0.141 (7)	0.063 (2)	0.080 (3)	0.025 (3)	0.072 (4)	−0.007 (2)
Cl3	0.130 (7)	0.067 (3)	0.135 (7)	0.042 (4)	0.100 (6)	0.011 (4)
Cl4'	0.065 (3)	0.054 (4)	0.138 (5)	0.008 (3)	0.062 (3)	−0.005 (3)
Cl4	0.042 (2)	0.121 (6)	0.093 (2)	0.030 (3)	0.0198 (15)	−0.007 (3)
Cl5	0.084 (2)	0.088 (3)	0.0486 (15)	−0.0215 (17)	0.0129 (12)	−0.0129 (15)
Cl5'	0.065 (4)	0.172 (11)	0.047 (3)	0.025 (5)	0.003 (2)	0.018 (4)
Cl6'	0.117 (3)	0.0544 (16)	0.0664 (18)	−0.0120 (14)	0.0431 (17)	0.0116 (12)
Cl6	0.131 (5)	0.062 (3)	0.128 (4)	−0.045 (3)	0.089 (4)	−0.018 (3)

Geometric parameters (Å, º) top

C1—N1	1.301 (7)	C12—H12B	0.9700
C1—N2	1.317 (7)	C13—N6	1.484 (5)
C1—H1'	0.92 (5)	C13—C14	1.541 (5)
C2—C3	1.343 (7)	C13—H13	0.9800
C2—N1	1.372 (6)	C14—O5	1.233 (5)
C2—H2'	0.92 (4)	C14—O6	1.249 (5)
C3—N2	1.382 (6)	C15—Cl5'	1.526 (9)
C3—C4	1.487 (6)	C15—C16	1.569 (7)
C4—C5	1.534 (6)	C15—Cl4	1.644 (7)
C4—H4A	0.9700	C15—Cl6'	1.826 (7)
C4—H4B	0.9700	C15—Cl5	1.854 (7)
C5—N3	1.479 (5)	C15—Cl4'	1.855 (9)
C5—C6	1.542 (5)	C15—Cl6	1.859 (8)
C5—H6	0.9800	C16—O8	1.213 (6)
C6—O1	1.231 (5)	C16—O7	1.231 (6)
C6—O2	1.253 (5)	N1—H1	0.85 (5)
C7—C8	1.573 (6)	N2—H2	0.85 (4)
C7—Cl2'	1.59 (2)	N3—H3A	0.8900
C7—Cl1	1.648 (11)	N3—H3B	0.8900
C7—Cl3	1.755 (8)	N3—H3C	0.8900
C7—Cl3'	1.797 (8)	N4—H4	0.86 (6)
C7—Cl2	1.824 (8)	N5—H5	0.85 (3)
C7—Cl1'	1.853 (9)	N6—H6A	0.8900
C8—O3	1.221 (6)	N6—H6B	0.8900
C8—O4	1.227 (6)	N6—H6C	0.8900
C9—N5	1.302 (8)	Cl1—Cl1'	0.644 (10)
C9—N4	1.332 (8)	Cl1—Cl3	2.27 (2)
C9—H9	0.92 (4)	Cl2—Cl2'	0.66 (3)
C10—C11	1.350 (7)	Cl2'—Cl3'	2.17 (4)
C10—N5	1.362 (6)	Cl3'—Cl3	0.994 (9)
C10—H10	0.92 (5)	Cl4'—Cl4	0.841 (6)
C11—N4	1.362 (6)	Cl4—Cl6	2.050 (12)
C11—C12	1.485 (7)	Cl5—Cl5'	0.969 (14)
C12—C13	1.545 (6)	Cl5'—Cl6'	1.919 (17)
C12—H12A	0.9700	Cl6'—Cl6	1.546 (8)

N1—C1—N2	108.8 (4)	C16—C15—Cl4	113.8 (5)
N1—C1—H1'	119 (4)	Cl5'—C15—Cl6'	69.2 (7)
N2—C1—H1'	131 (4)	C16—C15—Cl6'	111.1 (4)
C3—C2—N1	107.9 (4)	Cl4—C15—Cl6'	112.3 (5)
C3—C2—H2'	128 (3)	Cl5'—C15—Cl5	31.5 (5)
N1—C2—H2'	124 (3)	C16—C15—Cl5	109.2 (4)
C2—C3—N2	105.3 (4)	Cl4—C15—Cl5	109.1 (5)
C2—C3—C4	130.3 (4)	Cl6'—C15—Cl5	100.4 (4)
N2—C3—C4	124.2 (4)	Cl5'—C15—Cl4'	114.0 (7)
C3—C4—C5	116.2 (4)	C16—C15—Cl4'	106.2 (4)
C3—C4—H4A	108.2	Cl4—C15—Cl4'	26.9 (2)
C5—C4—H4A	108.2	Cl6'—C15—Cl4'	135.6 (4)
C3—C4—H4B	108.2	Cl5—C15—Cl4'	89.0 (5)
C5—C4—H4B	108.2	Cl5'—C15—Cl6	115.0 (7)
H4A—C4—H4B	107.4	C16—C15—Cl6	105.1 (4)
N3—C5—C4	107.4 (3)	Cl4—C15—Cl6	71.3 (5)
N3—C5—C6	110.4 (3)	Cl6'—C15—Cl6	49.6 (3)
C4—C5—C6	112.0 (3)	Cl5—C15—Cl6	141.3 (4)
N3—C5—H6	109.0	Cl4'—C15—Cl6	98.2 (5)
C4—C5—H6	109.0	O8—C16—O7	128.3 (5)
C6—C5—H6	109.0	O8—C16—C15	116.6 (4)
O1—C6—O2	126.6 (4)	O7—C16—C15	115.1 (4)
O1—C6—C5	116.9 (3)	C1—N1—C2	108.7 (4)
O2—C6—C5	116.4 (3)	C1—N1—H1	124 (6)
C8—C7—Cl2'	114.1 (7)	C2—N1—H1	128 (6)
C8—C7—Cl1	113.2 (6)	C1—N2—C3	109.3 (4)
Cl2'—C7—Cl1	122.1 (7)	C1—N2—H2	131 (4)
C8—C7—Cl3	111.1 (4)	C3—N2—H2	119 (4)
Cl2'—C7—Cl3	108.1 (14)	C5—N3—H3A	109.5
Cl1—C7—Cl3	83.4 (10)	C5—N3—H3B	109.5
C8—C7—Cl3'	111.2 (4)	H3A—N3—H3B	109.5
Cl2'—C7—Cl3'	79.4 (14)	C5—N3—H3C	109.5
Cl1—C7—Cl3'	111.7 (10)	H3A—N3—H3C	109.5
Cl3—C7—Cl3'	32.5 (3)	H3B—N3—H3C	109.5
C8—C7—Cl2	107.8 (4)	C9—N4—C11	109.1 (4)
Cl2'—C7—Cl2	21.0 (9)	C9—N4—H4	113 (6)
Cl1—C7—Cl2	111.7 (6)	C11—N4—H4	126 (7)
Cl3—C7—Cl2	127.5 (8)	C9—N5—C10	108.7 (4)
Cl3'—C7—Cl2	100.3 (7)	C9—N5—H5	120 (4)
C8—C7—Cl1'	106.7 (4)	C10—N5—H5	131 (4)
Cl2'—C7—Cl1'	112.9 (10)	C13—N6—H6A	109.5
Cl1—C7—Cl1'	20.1 (4)	C13—N6—H6B	109.5
Cl3—C7—Cl1'	103.5 (7)	H6A—N6—H6B	109.5
Cl3'—C7—Cl1'	130.1 (6)	C13—N6—H6C	109.5
Cl2—C7—Cl1'	97.5 (7)	H6A—N6—H6C	109.5
O3—C8—O4	128.3 (4)	H6B—N6—H6C	109.5
O3—C8—C7	115.2 (4)	Cl1'—Cl1—C7	98.2 (11)
O4—C8—C7	116.5 (5)	Cl1'—Cl1—Cl3	148.2 (13)
N5—C9—N4	108.5 (5)	C7—Cl1—Cl3	50.3 (7)
N5—C9—H9	127 (4)	Cl1—Cl1'—C7	61.7 (10)
N4—C9—H9	124 (4)	Cl2'—Cl2—C7	58.8 (14)
C11—C10—N5	107.9 (4)	Cl2—Cl2'—C7	100.2 (14)
C11—C10—H10	130 (4)	Cl2—Cl2'—Cl3'	154.3 (19)
N5—C10—H10	122 (4)	C7—Cl2'—Cl3'	54.6 (12)
C10—C11—N4	105.7 (4)	Cl3—Cl3'—C7	71.4 (5)
C10—C11—C12	132.4 (5)	Cl3—Cl3'—Cl2'	112.3 (7)
N4—C11—C12	121.4 (4)	C7—Cl3'—Cl2'	46.0 (4)
C11—C12—C13	116.6 (4)	Cl3'—Cl3—C7	76.1 (6)
C11—C12—H12A	108.1	Cl3'—Cl3—Cl1	116.5 (7)
C13—C12—H12A	108.1	C7—Cl3—Cl1	46.3 (4)
C11—C12—H12B	108.1	Cl4—Cl4'—C15	62.4 (5)
C13—C12—H12B	108.1	Cl4'—Cl4—C15	90.6 (5)
H12A—C12—H12B	107.3	Cl4'—Cl4—Cl6	149.8 (6)
N6—C13—C14	110.8 (3)	C15—Cl4—Cl6	59.2 (4)
N6—C13—C12	106.4 (3)	Cl5'—Cl5—C15	55.3 (4)
C14—C13—C12	110.5 (3)	Cl5—Cl5'—C15	93.3 (7)
N6—C13—H13	109.7	Cl5—Cl5'—Cl6'	154.8 (6)
C14—C13—H13	109.7	C15—Cl5'—Cl6'	62.8 (6)
C12—C13—H13	109.7	Cl6—Cl6'—C15	66.3 (3)
O5—C14—O6	127.4 (4)	Cl6—Cl6'—Cl5'	110.9 (3)
O5—C14—C13	117.0 (3)	C15—Cl6'—Cl5'	48.0 (3)
O6—C14—C13	115.5 (4)	Cl6'—Cl6—C15	64.1 (3)
Cl5'—C15—C16	116.2 (5)	Cl6'—Cl6—Cl4	105.8 (3)
Cl5'—C15—Cl4	124.7 (5)	C15—Cl6—Cl4	49.5 (3)

N1—C2—C3—N2	−0.6 (6)	Cl1—C7—Cl3'—Cl3	−31.4 (7)
N1—C2—C3—C4	−175.7 (4)	Cl2—C7—Cl3'—Cl3	−149.9 (6)
C2—C3—C4—C5	−148.7 (5)	Cl1'—C7—Cl3'—Cl3	−40.7 (8)
N2—C3—C4—C5	37.1 (6)	C8—C7—Cl3'—Cl2'	−111.9 (6)
C3—C4—C5—N3	157.0 (3)	Cl1—C7—Cl3'—Cl2'	120.5 (6)
C3—C4—C5—C6	−81.6 (5)	Cl3—C7—Cl3'—Cl2'	151.9 (8)
N3—C5—C6—O1	19.0 (5)	Cl2—C7—Cl3'—Cl2'	2.0 (6)
C4—C5—C6—O1	−100.6 (5)	Cl1'—C7—Cl3'—Cl2'	111.2 (9)
N3—C5—C6—O2	−163.6 (4)	Cl2—Cl2'—Cl3'—Cl3	16 (4)
C4—C5—C6—O2	76.8 (5)	C7—Cl2'—Cl3'—Cl3	28.9 (7)
Cl2'—C7—C8—O3	83.5 (14)	Cl2—Cl2'—Cl3'—C7	−12 (4)
Cl1—C7—C8—O3	−62.2 (9)	Cl2'—Cl3'—Cl3—C7	−21.5 (6)
Cl3—C7—C8—O3	−154.0 (8)	C7—Cl3'—Cl3—Cl1	23.1 (5)
Cl3'—C7—C8—O3	171.1 (6)	Cl2'—Cl3'—Cl3—Cl1	1.6 (9)
Cl2—C7—C8—O3	62.0 (7)	C8—C7—Cl3—Cl3'	−96.7 (8)
Cl1'—C7—C8—O3	−41.9 (7)	Cl2'—C7—Cl3—Cl3'	29.2 (8)
Cl2'—C7—C8—O4	−96.1 (14)	Cl1—C7—Cl3—Cl3'	150.9 (7)
Cl1—C7—C8—O4	118.2 (9)	Cl2—C7—Cl3—Cl3'	38.4 (7)
Cl3—C7—C8—O4	26.3 (9)	Cl1'—C7—Cl3—Cl3'	149.1 (6)
Cl3'—C7—C8—O4	−8.6 (8)	C8—C7—Cl3—Cl1	112.4 (6)
Cl2—C7—C8—O4	−117.7 (7)	Cl2'—C7—Cl3—Cl1	−121.7 (7)
Cl1'—C7—C8—O4	138.4 (7)	Cl3'—C7—Cl3—Cl1	−150.9 (7)
N5—C10—C11—N4	1.0 (6)	Cl2—C7—Cl3—Cl1	−112.4 (7)
N5—C10—C11—C12	172.7 (5)	Cl1'—C7—Cl3—Cl1	−1.7 (6)
C10—C11—C12—C13	112.5 (6)	Cl1'—Cl1—Cl3—Cl3'	−23 (4)
N4—C11—C12—C13	−76.8 (6)	C7—Cl1—Cl3—Cl3'	−31.9 (6)
C11—C12—C13—N6	159.7 (4)	Cl1'—Cl1—Cl3—C7	9 (3)
C11—C12—C13—C14	−80.0 (5)	Cl5'—C15—Cl4'—Cl4	−119.8 (9)
N6—C13—C14—O5	23.2 (5)	C16—C15—Cl4'—Cl4	110.9 (7)
C12—C13—C14—O5	−94.4 (5)	Cl6'—C15—Cl4'—Cl4	−35.6 (10)
N6—C13—C14—O6	−159.8 (4)	Cl5—C15—Cl4'—Cl4	−139.4 (7)
C12—C13—C14—O6	82.6 (5)	Cl6—C15—Cl4'—Cl4	2.4 (7)
Cl5'—C15—C16—O8	93.7 (9)	C15—Cl4'—Cl4—Cl6	−4.2 (13)
Cl4—C15—C16—O8	−110.7 (7)	Cl5'—C15—Cl4—Cl4'	74.5 (12)
Cl6'—C15—C16—O8	17.2 (7)	C16—C15—Cl4—Cl4'	−78.8 (8)
Cl5—C15—C16—O8	127.0 (5)	Cl6'—C15—Cl4—Cl4'	153.9 (7)
Cl4'—C15—C16—O8	−138.3 (6)	Cl5—C15—Cl4—Cl4'	43.5 (8)
Cl6—C15—C16—O8	−34.8 (7)	Cl6—C15—Cl4—Cl4'	−177.5 (8)
Cl5'—C15—C16—O7	−87.2 (9)	Cl5'—C15—Cl4—Cl6	−108.0 (9)
Cl4—C15—C16—O7	68.3 (7)	C16—C15—Cl4—Cl6	98.8 (5)
Cl6'—C15—C16—O7	−163.7 (4)	Cl6'—C15—Cl4—Cl6	−28.6 (3)
Cl5—C15—C16—O7	−53.9 (6)	Cl5—C15—Cl4—Cl6	−139.0 (5)
Cl4'—C15—C16—O7	40.8 (7)	Cl4'—C15—Cl4—Cl6	177.5 (8)
Cl6—C15—C16—O7	144.3 (5)	C16—C15—Cl5—Cl5'	−109.1 (7)
N2—C1—N1—C2	0.9 (6)	Cl4—C15—Cl5—Cl5'	125.9 (7)
C3—C2—N1—C1	−0.2 (6)	Cl6'—C15—Cl5—Cl5'	7.7 (6)
N1—C1—N2—C3	−1.4 (7)	Cl4'—C15—Cl5—Cl5'	144.1 (6)
C2—C3—N2—C1	1.2 (6)	Cl6—C15—Cl5—Cl5'	42.1 (8)
C4—C3—N2—C1	176.7 (5)	C15—Cl5—Cl5'—Cl6'	−17.2 (12)
N5—C9—N4—C11	0.5 (7)	C16—C15—Cl5'—Cl5	84.1 (7)
C10—C11—N4—C9	−0.9 (6)	Cl4—C15—Cl5'—Cl5	−68.5 (9)
C12—C11—N4—C9	−173.8 (5)	Cl6'—C15—Cl5'—Cl5	−171.9 (6)
N4—C9—N5—C10	0.1 (7)	Cl4'—C15—Cl5'—Cl5	−40.0 (7)
C11—C10—N5—C9	−0.7 (6)	Cl6—C15—Cl5'—Cl5	−152.4 (5)
C8—C7—Cl1—Cl1'	74.7 (15)	C16—C15—Cl5'—Cl6'	−104.0 (6)
Cl2'—C7—Cl1—Cl1'	−68 (2)	Cl4—C15—Cl5'—Cl6'	103.4 (8)
Cl3—C7—Cl1—Cl1'	−175.1 (17)	Cl5—C15—Cl5'—Cl6'	171.9 (6)
Cl3'—C7—Cl1—Cl1'	−158.8 (16)	Cl4'—C15—Cl5'—Cl6'	131.9 (5)
Cl2—C7—Cl1—Cl1'	−47.3 (19)	Cl6—C15—Cl5'—Cl6'	19.5 (4)
C8—C7—Cl1—Cl3	−110.2 (7)	Cl5'—C15—Cl6'—Cl6	156.6 (4)
Cl2'—C7—Cl1—Cl3	107.3 (17)	C16—C15—Cl6'—Cl6	−92.3 (5)
Cl3'—C7—Cl1—Cl3	16.3 (4)	Cl4—C15—Cl6'—Cl6	36.5 (4)
Cl2—C7—Cl1—Cl3	127.8 (7)	Cl5—C15—Cl6'—Cl6	152.3 (4)
Cl1'—C7—Cl1—Cl3	175.1 (17)	Cl4'—C15—Cl6'—Cl6	53.1 (7)
Cl3—Cl1—Cl1'—C7	−7 (2)	C16—C15—Cl6'—Cl5'	111.1 (6)
C8—C7—Cl1'—Cl1	−112.3 (16)	Cl4—C15—Cl6'—Cl5'	−120.1 (5)
Cl2'—C7—Cl1'—Cl1	122 (2)	Cl5—C15—Cl6'—Cl5'	−4.3 (3)
Cl3—C7—Cl1'—Cl1	5.0 (17)	Cl4'—C15—Cl6'—Cl5'	−103.6 (8)
Cl3'—C7—Cl1'—Cl1	26 (2)	Cl6—C15—Cl6'—Cl5'	−156.6 (4)
Cl2—C7—Cl1'—Cl1	136.5 (16)	Cl5—Cl5'—Cl6'—Cl6	−3.5 (16)
C8—C7—Cl2—Cl2'	111.0 (16)	C15—Cl5'—Cl6'—Cl6	−22.9 (4)
Cl1—C7—Cl2—Cl2'	−123.9 (19)	Cl5—Cl5'—Cl6'—C15	19.4 (14)
Cl3—C7—Cl2—Cl2'	−25.3 (19)	Cl5'—Cl6'—Cl6—C15	18.4 (3)
Cl3'—C7—Cl2—Cl2'	−5.5 (17)	C15—Cl6'—Cl6—Cl4	−27.3 (3)
Cl1'—C7—Cl2—Cl2'	−138.7 (17)	Cl5'—Cl6'—Cl6—Cl4	−8.9 (4)
C7—Cl2—Cl2'—Cl3'	10 (3)	Cl5'—C15—Cl6—Cl6'	−24.2 (5)
C8—C7—Cl2'—Cl2	−76.8 (16)	C16—C15—Cl6—Cl6'	105.0 (4)
Cl1—C7—Cl2'—Cl2	65 (2)	Cl4—C15—Cl6—Cl6'	−144.5 (4)
Cl3—C7—Cl2'—Cl2	159.1 (16)	Cl5—C15—Cl6—Cl6'	−46.9 (7)
Cl3'—C7—Cl2'—Cl2	174.5 (17)	Cl4'—C15—Cl6—Cl6'	−145.6 (4)
Cl1'—C7—Cl2'—Cl2	45 (2)	Cl5'—C15—Cl6—Cl4	120.3 (6)
C8—C7—Cl2'—Cl3'	108.6 (8)	C16—C15—Cl6—Cl4	−110.5 (5)
Cl1—C7—Cl2'—Cl3'	−109.0 (13)	Cl6'—C15—Cl6—Cl4	144.5 (4)
Cl3—C7—Cl2'—Cl3'	−15.4 (4)	Cl5—C15—Cl6—Cl4	97.6 (7)
Cl2—C7—Cl2'—Cl3'	−174.5 (17)	Cl4'—C15—Cl6—Cl4	−1.1 (4)
Cl1'—C7—Cl2'—Cl3'	−129.3 (8)	Cl4'—Cl4—Cl6—Cl6'	37.8 (17)
C8—C7—Cl3'—Cl3	96.2 (7)	C15—Cl4—Cl6—Cl6'	32.9 (3)
Cl2'—C7—Cl3'—Cl3	−151.9 (8)	Cl4'—Cl4—Cl6—C15	4.9 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.89	1.94	2.815 (5)	169
N3—H3B···O8	0.89	1.93	2.681 (5)	141
N3—H3C···O6ⁱⁱ	0.89	2.02	2.787 (5)	144
N6—H6A···O2	0.89	2.02	2.889 (5)	164
N6—H6B···O5ⁱⁱⁱ	0.89	1.96	2.839 (4)	170
N6—H6C···O4^iv	0.89	1.88	2.713 (5)	155
N1—H1···O7^v	0.85 (5)	1.85 (3)	2.671 (5)	161 (8)
N2—H2···O2	0.85 (4)	1.99 (3)	2.761 (5)	150 (5)
N4—H4···O6ⁱⁱⁱ	0.86 (6)	2.39 (8)	2.923 (6)	122 (8)
N5—H5···O3^vi	0.85 (3)	1.88 (1)	2.715 (5)	168 (5)

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

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