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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2535.
Published online 2010 September 11. doi:  10.1107/S1600536810035853
PMCID: PMC2983198

2-Amino-5-chloro­pyridinium 2-carb­oxy­benzoate–benzene-1,2-dicarb­oxy­lic acid (3/1)

Abstract

The asymmetric unit of the title compound, 3C5H6ClN2 +·3C8H5O4 ·C8H6O4, contains three independent 2-amino-5-chloro­pyridinium cations, three independent hydrogen phthal­ate anions and one phthalic acid mol­ecule. In the crystal structure, there are two kinds of supra­molecular tapes. One is formed by two independent cations with two anions through N—H(...)O and C—H(...)O hydrogen bonds. Another one is formed by the other cation and anion, and the phthalic acid mol­ecule via N—H(...)O, O—H(...)O and C—H(...)O hydrogen bonds. These two tapes are connected by an O—H(...)O hydrogen bond, forming a double-tape structure.

Related literature

For details of hydrogen bonding, see: Jeffery (1997 [triangle]). For details of structures incorporating phthalic acid, see: Dale et al. (2004 [triangle]); Ballabh et al. (2005 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2535-scheme1.jpg

Experimental

Crystal data

  • 3C5H6ClN2 +·3C8H5O4 ·C8H6O4
  • M r = 1050.19
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2535-efi1.jpg
  • a = 9.8522 (2) Å
  • b = 14.0242 (2) Å
  • c = 17.4312 (3) Å
  • α = 68.920 (1)°
  • β = 87.507 (1)°
  • γ = 83.906 (1)°
  • V = 2234.54 (7) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 100 K
  • 0.49 × 0.22 × 0.22 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.870, T max = 0.940
  • 63061 measured reflections
  • 12966 independent reflections
  • 11359 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.101
  • S = 1.03
  • 12966 reflections
  • 696 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.44 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035853/is2597sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035853/is2597Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

MH and HKF thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

Hydrogen bonding is one of the key interactions for molecular assembly and molecular recognition (Jeffery, 1997). In nature, biopolymers such as nucleic acids and polypeptides form supramolecular structures through hydrogen bonding of which the dynamic nature of the interaction contributes to chemical and biological molecular processes. Phthalic acid forms hydrogen phthalate salts with various organic compounds. Hydrogen phthalates also form supramolecular assemblies, such as extended chains, ribbons and three-dimensional networks (Dale et al., 2004; Ballabh et al., 2005). In this paper, the hydrogen-bonding patterns of tris(2-amino-5-chloropyridinium hydrogen phthalate) phthalic acid, (I), are discussed.

The asymmetric unit of the title compound consists of three crystallographically independent 2-amino-5-chloropyridinium cations (A, B & C), three hydrogen phthalate anions (A, B & C) and one phthalic acid molecule (Fig. 1). Each 2-amino-5-chloropyridinium cation is planar, with a maximum deviation of 0.008 (1) Å for atom C4A (molecule A), 0.019 (1) Å for atom Cl1B (molecule B) and 0.028 (1) Å for atom N2C (molecule C).

In the crystal structure, there are two kinds of supramolecular tapes. One is formed by the cations A and B with the anions B and C, through N—H···O and C—H···O hydrogen bonds (Fig. 2). The another one is formed by the cation B, the anion A and the phthalic acid molecule via N—H···O, O—H···O and C—H···O hydrogen bonds (Fig. 3). Furthermore, these two tapes are connected by an O—H···O hydrogen bond, forming a double tape structure (Fig. 4). There is an intramolecular O—H···O hydrogen bond in the hydrogen phthalate anions, which generates an S(6) (Bernstein et al., 1995) ring motif.

Experimental

A hot methanol solution (20 ml) of 2-amino-5-chloropyridine (65 mg, Aldrich) and phthalic acid (83 mg, Merck) were mixed and warmed over a heating magnetic stirrer hotplate for a few minutes. The resulting solution was allowed to cool slowly at room temperature and yellow coloured crystals of the title compound appeared after a few days.

Refinement

Atoms H1OX, H2OX, H1NA, H2NA, H3NA, H1NB, H2NB, H3NB, H1NC, H2NC and H3NC were located from a difference Fourier map and were refined freely [N—H = 0.83 (2)–0.92 (2) Å and O—H =0.83 (2)–0.88 (2) Å]. The remaining O-bound H atoms were also located in a difference Fourier map. They were treated as riding and the isotropic displacement parameters were refined. The C-bound H atoms were positioned geometrically [C—H = 0.93 Å] and were refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A view of supramolecular tape formed by cations (A & B) with the anions (B & C) through N—H···O and C—H···O hydrogen bonds.
Fig. 3.
A view of supramolecular tape formed by cation B, the anion A and the phthalic acid molecule via N—H···O, O—H···O and C—H···O hydrogen bonds.
Fig. 4.
Hydrogen bonding patterns in (I).

Crystal data

3C5H6ClN2+·3C8H5O4·C8H6O4Z = 2
Mr = 1050.19F(000) = 1084
Triclinic, P1Dx = 1.561 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8522 (2) ÅCell parameters from 9964 reflections
b = 14.0242 (2) Åθ = 2.4–36.1°
c = 17.4312 (3) ŵ = 0.29 mm1
α = 68.920 (1)°T = 100 K
β = 87.507 (1)°Block, yellow
γ = 83.906 (1)°0.49 × 0.22 × 0.22 mm
V = 2234.54 (7) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer12966 independent reflections
Radiation source: fine-focus sealed tube11359 reflections with I > 2σ(I)
graphiteRint = 0.032
[var phi] and ω scansθmax = 30.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −13→13
Tmin = 0.870, Tmax = 0.940k = −19→19
63061 measured reflectionsl = −24→23

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0547P)2 + 0.8733P] where P = (Fo2 + 2Fc2)/3
12966 reflections(Δ/σ)max = 0.001
696 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = −0.35 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)

xyzUiso*/Ueq
Cl1A0.45378 (3)0.01683 (2)0.401827 (17)0.02226 (7)
N1A0.42388 (10)−0.14773 (7)0.26255 (6)0.01629 (18)
N2A0.37929 (11)−0.11497 (8)0.12618 (6)0.02002 (19)
C1A0.44162 (11)−0.11900 (9)0.32770 (7)0.0169 (2)
H1AA0.4604−0.16870.37930.020*
C2A0.43208 (11)−0.01796 (9)0.31773 (7)0.0166 (2)
C3A0.40361 (12)0.05652 (9)0.23923 (7)0.0186 (2)
H3AA0.39620.12600.23170.022*
C4A0.38690 (12)0.02632 (9)0.17425 (7)0.0186 (2)
H4AA0.36940.07520.12220.022*
C5A0.39631 (11)−0.07983 (9)0.18631 (7)0.0160 (2)
O1A0.10557 (9)0.89607 (6)0.30990 (5)0.02235 (18)
O2A0.12677 (9)0.75913 (7)0.27580 (5)0.02175 (17)
H1OA0.12410.69370.29900.074 (8)*
O3A0.11516 (9)0.57696 (6)0.34407 (5)0.02090 (17)
O4A0.13550 (9)0.45909 (6)0.46883 (5)0.01945 (16)
C6A0.15173 (11)0.73752 (8)0.42026 (7)0.01448 (19)
C7A0.15713 (11)0.62917 (8)0.45923 (7)0.01426 (19)
C8A0.18655 (12)0.58619 (9)0.54319 (7)0.0173 (2)
H8AA0.19000.51530.56910.021*
C9A0.21081 (12)0.64477 (9)0.58947 (7)0.0188 (2)
H9AA0.23090.61360.64510.023*
C10A0.20461 (11)0.75089 (9)0.55149 (7)0.0181 (2)
H10C0.22030.79160.58160.022*
C11A0.17475 (11)0.79561 (8)0.46828 (7)0.0166 (2)
H11C0.16990.86670.44350.020*
C12A0.12482 (11)0.80204 (9)0.33027 (7)0.0169 (2)
C13A0.13380 (11)0.55001 (8)0.42119 (7)0.0159 (2)
Cl1B0.83721 (3)0.98373 (2)0.460859 (17)0.02238 (7)
N1B0.87824 (10)0.68696 (7)0.58805 (6)0.01643 (18)
N2B0.92305 (11)0.58396 (8)0.72337 (6)0.0204 (2)
C1B0.85787 (11)0.77934 (9)0.52648 (7)0.0168 (2)
H1BA0.84190.78240.47340.020*
C2B0.86063 (11)0.86783 (8)0.54165 (7)0.0167 (2)
C3B0.88534 (12)0.86258 (9)0.62235 (7)0.0180 (2)
H3BA0.88760.92230.63370.022*
C4B0.90591 (12)0.76850 (9)0.68346 (7)0.0180 (2)
H4BA0.92240.76410.73680.022*
C5B0.90231 (11)0.67760 (9)0.66603 (7)0.0163 (2)
O1B0.69143 (10)0.98082 (7)0.04092 (6)0.02612 (19)
O2B0.65261 (11)0.84422 (7)0.01512 (5)0.02608 (19)
H1OB0.66050.77600.03940.063 (7)*
O3B0.66767 (10)0.65998 (7)0.08159 (5)0.02202 (17)
O4B0.74305 (12)0.54133 (7)0.19770 (6)0.0299 (2)
C6B0.72617 (11)0.82179 (8)0.15300 (7)0.0158 (2)
C7B0.73424 (11)0.71332 (8)0.19160 (7)0.0161 (2)
C8B0.76723 (13)0.67044 (9)0.27519 (7)0.0208 (2)
H8BA0.77310.59940.30090.025*
C9B0.79150 (13)0.72924 (10)0.32115 (8)0.0229 (2)
H9BA0.81150.69820.37680.027*
C10B0.78571 (13)0.83507 (9)0.28324 (8)0.0218 (2)
H10D0.80290.87570.31310.026*
C11B0.75399 (12)0.87967 (9)0.20027 (7)0.0189 (2)
H11D0.75110.95060.17510.023*
C12B0.68907 (12)0.88739 (9)0.06458 (7)0.0191 (2)
C13B0.71365 (12)0.63318 (9)0.15401 (7)0.0184 (2)
Cl1C0.74116 (3)0.09871 (2)0.262958 (19)0.02519 (7)
N1C0.71246 (10)0.39640 (8)0.14020 (6)0.01702 (18)
N2C0.66401 (12)0.50347 (8)0.00715 (6)0.0212 (2)
C1C0.73257 (12)0.30282 (9)0.20019 (7)0.0179 (2)
H1CA0.75860.29750.25230.022*
C2C0.71499 (12)0.21651 (9)0.18475 (7)0.0179 (2)
C3C0.67473 (12)0.22535 (9)0.10550 (7)0.0202 (2)
H3CA0.66100.16710.09430.024*
C4C0.65611 (12)0.32028 (9)0.04550 (7)0.0198 (2)
H4CA0.62960.3269−0.00690.024*
C5C0.67722 (11)0.40911 (9)0.06294 (7)0.0167 (2)
O1C0.43733 (9)0.64971 (6)0.32698 (5)0.02123 (17)
O2C0.40372 (9)0.63362 (6)0.20871 (5)0.02070 (17)
H2C0.40070.58750.19050.031*
O3C0.38734 (10)0.49905 (7)0.15591 (5)0.02425 (18)
O4C0.38122 (9)0.33117 (7)0.19965 (5)0.02149 (17)
C60.43344 (10)0.47894 (8)0.33267 (7)0.01398 (19)
C7C0.42704 (11)0.39947 (8)0.30070 (7)0.01478 (19)
C8C0.44379 (11)0.29758 (9)0.35547 (7)0.0178 (2)
H8CA0.44290.24490.33490.021*
C9C0.46168 (12)0.27235 (9)0.43908 (7)0.0197 (2)
H9CA0.47300.20390.47380.024*
C10C0.46265 (12)0.34990 (9)0.47055 (7)0.0203 (2)
H10B0.47160.33410.52680.024*
C11C0.45017 (11)0.45127 (9)0.41744 (7)0.0173 (2)
H11B0.45300.50280.43900.021*
C12C0.42405 (11)0.59425 (8)0.28679 (7)0.01572 (19)
C13C0.39680 (11)0.41033 (9)0.21310 (7)0.0163 (2)
O1X0.04664 (9)0.38078 (6)0.11892 (5)0.02047 (17)
O2X0.23396 (8)0.28591 (6)0.09895 (5)0.01790 (16)
O3X0.06412 (10)0.13221 (6)0.19699 (5)0.02195 (17)
O4X0.05428 (10)0.00430 (6)0.15024 (6)0.02134 (17)
C6X0.03190 (11)0.27963 (8)0.03490 (7)0.01521 (19)
C7X0.01326 (11)0.17532 (8)0.05616 (7)0.01504 (19)
C8X−0.04564 (11)0.14237 (9)−0.00028 (7)0.0180 (2)
H8XA−0.05900.07350.01380.022*
C9X−0.08435 (12)0.21229 (10)−0.07743 (7)0.0216 (2)
H9XA−0.12050.1898−0.11560.026*
C10X−0.06893 (13)0.31588 (10)−0.09748 (7)0.0222 (2)
H10A−0.09700.3627−0.14860.027*
C11X−0.01162 (12)0.34997 (9)−0.04143 (7)0.0191 (2)
H11A−0.00240.4194−0.05490.023*
C12X0.10282 (11)0.31957 (8)0.09010 (6)0.01542 (19)
C13X0.04723 (11)0.10283 (8)0.14117 (7)0.01508 (19)
H1OX0.2711 (19)0.3112 (15)0.1314 (12)0.041 (5)*
H2OX0.070 (2)−0.0309 (16)0.1993 (13)0.041 (5)*
H1NA0.4293 (17)−0.2157 (14)0.2731 (11)0.030 (4)*
H2NA0.3604 (17)−0.0697 (14)0.0756 (11)0.032 (4)*
H3NA0.3800 (17)−0.1818 (14)0.1364 (11)0.030 (4)*
H1NB0.880 (2)0.6302 (16)0.5737 (13)0.048 (6)*
H2NB0.9243 (18)0.5284 (15)0.7124 (11)0.033 (4)*
H3NB0.9351 (18)0.5837 (14)0.7723 (12)0.030 (4)*
H1NC0.7207 (19)0.4549 (15)0.1536 (13)0.044 (5)*
H2NC0.6456 (18)0.5087 (14)−0.0434 (12)0.034 (5)*
H3NC0.6673 (18)0.5536 (15)0.0214 (12)0.034 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl1A0.03296 (15)0.01957 (13)0.01586 (12)−0.00135 (11)−0.00293 (10)−0.00829 (10)
N1A0.0208 (4)0.0126 (4)0.0151 (4)−0.0025 (3)−0.0013 (3)−0.0041 (3)
N2A0.0270 (5)0.0179 (5)0.0163 (5)−0.0040 (4)−0.0025 (4)−0.0067 (4)
C1A0.0200 (5)0.0158 (5)0.0134 (5)−0.0023 (4)−0.0008 (4)−0.0033 (4)
C2A0.0199 (5)0.0166 (5)0.0141 (5)−0.0024 (4)−0.0013 (4)−0.0061 (4)
C3A0.0238 (5)0.0128 (5)0.0181 (5)−0.0014 (4)−0.0022 (4)−0.0042 (4)
C4A0.0230 (5)0.0155 (5)0.0145 (5)−0.0020 (4)−0.0027 (4)−0.0016 (4)
C5A0.0155 (4)0.0170 (5)0.0153 (5)−0.0027 (4)−0.0002 (4)−0.0052 (4)
O1A0.0317 (4)0.0138 (4)0.0201 (4)−0.0019 (3)−0.0044 (3)−0.0039 (3)
O2A0.0339 (5)0.0161 (4)0.0150 (4)−0.0027 (3)−0.0025 (3)−0.0050 (3)
O3A0.0321 (4)0.0161 (4)0.0168 (4)−0.0027 (3)−0.0044 (3)−0.0081 (3)
O4A0.0282 (4)0.0137 (4)0.0181 (4)−0.0040 (3)0.0005 (3)−0.0072 (3)
C6A0.0151 (4)0.0134 (5)0.0149 (5)−0.0024 (4)0.0002 (4)−0.0048 (4)
C7A0.0163 (4)0.0130 (5)0.0151 (5)−0.0024 (4)0.0000 (4)−0.0068 (4)
C8A0.0223 (5)0.0143 (5)0.0150 (5)−0.0025 (4)−0.0003 (4)−0.0046 (4)
C9A0.0232 (5)0.0193 (5)0.0148 (5)−0.0025 (4)−0.0019 (4)−0.0071 (4)
C10A0.0208 (5)0.0182 (5)0.0189 (5)−0.0031 (4)−0.0008 (4)−0.0107 (4)
C11A0.0185 (5)0.0137 (5)0.0185 (5)−0.0033 (4)0.0003 (4)−0.0065 (4)
C12A0.0173 (5)0.0163 (5)0.0166 (5)−0.0030 (4)−0.0010 (4)−0.0049 (4)
C13A0.0174 (5)0.0152 (5)0.0170 (5)−0.0017 (4)−0.0003 (4)−0.0082 (4)
Cl1B0.03245 (15)0.01553 (12)0.01737 (13)−0.00288 (10)−0.00214 (10)−0.00333 (10)
N1B0.0214 (4)0.0147 (4)0.0153 (4)−0.0026 (3)0.0000 (3)−0.0077 (4)
N2B0.0317 (5)0.0145 (4)0.0157 (5)−0.0021 (4)−0.0024 (4)−0.0062 (4)
C1B0.0191 (5)0.0180 (5)0.0148 (5)−0.0024 (4)−0.0006 (4)−0.0075 (4)
C2B0.0203 (5)0.0145 (5)0.0150 (5)−0.0022 (4)−0.0002 (4)−0.0048 (4)
C3B0.0232 (5)0.0161 (5)0.0180 (5)−0.0039 (4)0.0011 (4)−0.0098 (4)
C4B0.0244 (5)0.0171 (5)0.0154 (5)−0.0039 (4)0.0003 (4)−0.0087 (4)
C5B0.0187 (5)0.0164 (5)0.0158 (5)−0.0026 (4)0.0009 (4)−0.0080 (4)
O1B0.0377 (5)0.0162 (4)0.0208 (4)−0.0039 (4)−0.0039 (4)−0.0015 (3)
O2B0.0468 (6)0.0167 (4)0.0135 (4)0.0012 (4)−0.0051 (4)−0.0046 (3)
O3B0.0350 (5)0.0188 (4)0.0133 (4)−0.0041 (3)−0.0026 (3)−0.0063 (3)
O4B0.0557 (6)0.0146 (4)0.0204 (4)−0.0036 (4)−0.0118 (4)−0.0062 (3)
C6B0.0170 (5)0.0144 (5)0.0149 (5)−0.0021 (4)0.0003 (4)−0.0039 (4)
C7B0.0200 (5)0.0150 (5)0.0143 (5)−0.0033 (4)−0.0008 (4)−0.0060 (4)
C8B0.0311 (6)0.0152 (5)0.0158 (5)−0.0027 (4)−0.0046 (4)−0.0047 (4)
C9B0.0322 (6)0.0208 (6)0.0166 (5)−0.0015 (5)−0.0072 (4)−0.0073 (4)
C10B0.0262 (6)0.0197 (5)0.0224 (6)−0.0018 (4)−0.0055 (4)−0.0107 (5)
C11B0.0218 (5)0.0143 (5)0.0207 (5)−0.0023 (4)−0.0018 (4)−0.0062 (4)
C12B0.0231 (5)0.0172 (5)0.0153 (5)−0.0013 (4)0.0007 (4)−0.0038 (4)
C13B0.0255 (5)0.0163 (5)0.0140 (5)−0.0043 (4)−0.0005 (4)−0.0055 (4)
Cl1C0.03599 (16)0.01527 (13)0.02110 (14)−0.00401 (11)−0.00132 (11)−0.00209 (10)
N1C0.0234 (5)0.0146 (4)0.0141 (4)−0.0031 (3)−0.0017 (3)−0.0058 (3)
N2C0.0339 (5)0.0163 (5)0.0139 (4)−0.0053 (4)−0.0028 (4)−0.0050 (4)
C1C0.0228 (5)0.0163 (5)0.0143 (5)−0.0024 (4)−0.0011 (4)−0.0048 (4)
C2C0.0218 (5)0.0151 (5)0.0154 (5)−0.0028 (4)0.0013 (4)−0.0036 (4)
C3C0.0258 (5)0.0184 (5)0.0197 (5)−0.0053 (4)0.0019 (4)−0.0100 (4)
C4C0.0272 (6)0.0193 (5)0.0159 (5)−0.0055 (4)0.0000 (4)−0.0092 (4)
C5C0.0196 (5)0.0169 (5)0.0145 (5)−0.0034 (4)0.0006 (4)−0.0064 (4)
O1C0.0328 (4)0.0140 (4)0.0182 (4)−0.0034 (3)−0.0033 (3)−0.0067 (3)
O2C0.0326 (4)0.0150 (4)0.0147 (4)−0.0024 (3)−0.0025 (3)−0.0053 (3)
O3C0.0397 (5)0.0199 (4)0.0137 (4)−0.0033 (4)−0.0043 (3)−0.0060 (3)
O4C0.0261 (4)0.0210 (4)0.0219 (4)−0.0013 (3)−0.0069 (3)−0.0126 (3)
C60.0153 (4)0.0131 (4)0.0139 (5)−0.0015 (3)−0.0019 (3)−0.0050 (4)
C7C0.0156 (4)0.0161 (5)0.0140 (5)−0.0024 (4)−0.0020 (4)−0.0066 (4)
C8C0.0203 (5)0.0141 (5)0.0203 (5)−0.0025 (4)−0.0035 (4)−0.0069 (4)
C9C0.0226 (5)0.0150 (5)0.0192 (5)−0.0028 (4)−0.0039 (4)−0.0026 (4)
C10C0.0250 (5)0.0201 (5)0.0143 (5)−0.0010 (4)−0.0039 (4)−0.0044 (4)
C11C0.0215 (5)0.0170 (5)0.0144 (5)−0.0014 (4)−0.0031 (4)−0.0067 (4)
C12C0.0168 (5)0.0146 (5)0.0157 (5)−0.0019 (4)−0.0006 (4)−0.0052 (4)
C13C0.0170 (5)0.0187 (5)0.0152 (5)−0.0011 (4)−0.0025 (4)−0.0083 (4)
O1X0.0276 (4)0.0166 (4)0.0190 (4)−0.0009 (3)−0.0017 (3)−0.0087 (3)
O2X0.0203 (4)0.0190 (4)0.0179 (4)−0.0035 (3)−0.0032 (3)−0.0099 (3)
O3X0.0367 (5)0.0150 (4)0.0151 (4)−0.0046 (3)−0.0026 (3)−0.0057 (3)
O4X0.0341 (5)0.0121 (4)0.0180 (4)−0.0022 (3)−0.0065 (3)−0.0048 (3)
C6X0.0171 (5)0.0157 (5)0.0138 (5)−0.0020 (4)−0.0016 (4)−0.0061 (4)
C7X0.0173 (5)0.0144 (5)0.0143 (5)−0.0015 (4)−0.0015 (4)−0.0061 (4)
C8X0.0204 (5)0.0180 (5)0.0179 (5)−0.0030 (4)−0.0023 (4)−0.0086 (4)
C9X0.0232 (5)0.0266 (6)0.0175 (5)−0.0042 (4)−0.0047 (4)−0.0100 (5)
C10X0.0257 (6)0.0238 (6)0.0151 (5)−0.0031 (4)−0.0051 (4)−0.0038 (4)
C11X0.0236 (5)0.0164 (5)0.0160 (5)−0.0040 (4)−0.0027 (4)−0.0033 (4)
C12X0.0217 (5)0.0119 (4)0.0121 (4)−0.0046 (4)−0.0013 (4)−0.0025 (4)
C13X0.0173 (5)0.0129 (5)0.0158 (5)−0.0031 (4)−0.0007 (4)−0.0054 (4)

Geometric parameters (Å, °)

Cl1A—C2A1.7311 (11)C8B—H8BA0.9300
N1A—C5A1.3464 (14)C9B—C10B1.3865 (17)
N1A—C1A1.3579 (14)C9B—H9BA0.9300
N1A—H1NA0.899 (18)C10B—C11B1.3884 (17)
N2A—C5A1.3320 (15)C10B—H10D0.9300
N2A—H2NA0.896 (18)C11B—H11D0.9300
N2A—H3NA0.888 (18)Cl1C—C2C1.7246 (12)
C1A—C2A1.3575 (16)N1C—C5C1.3493 (14)
C1A—H1AA0.9300N1C—C1C1.3532 (14)
C2A—C3A1.4089 (15)N1C—H1NC0.94 (2)
C3A—C4A1.3659 (16)N2C—C5C1.3276 (15)
C3A—H3AA0.9300N2C—H2NC0.88 (2)
C4A—C5A1.4199 (16)N2C—H3NC0.83 (2)
C4A—H4AA0.9300C1C—C2C1.3603 (16)
O1A—C12A1.2315 (14)C1C—H1CA0.9300
O2A—C12A1.2927 (14)C2C—C3C1.4125 (16)
O2A—H1OA0.8626C3C—C4C1.3649 (17)
O3A—C13A1.2748 (14)C3C—H3CA0.9300
O4A—C13A1.2453 (14)C4C—C5C1.4214 (16)
C6A—C11A1.4007 (15)C4C—H4CA0.9300
C6A—C7A1.4201 (14)O1C—C12C1.2388 (14)
C6A—C12A1.5212 (15)O2C—C12C1.2873 (13)
C7A—C8A1.3981 (15)O2C—H2C0.8200
C7A—C13A1.5237 (15)O3C—C13C1.2814 (14)
C8A—C9A1.3849 (16)O4C—C13C1.2400 (14)
C8A—H8AA0.9300C6—C11C1.3986 (15)
C9A—C10A1.3902 (16)C6—C7C1.4218 (15)
C9A—H9AA0.9300C6—C12C1.5191 (15)
C10A—C11A1.3882 (16)C7C—C8C1.4009 (15)
C10A—H10C0.9300C7C—C13C1.5186 (15)
C11A—H11C0.9300C8C—C9C1.3852 (16)
Cl1B—C2B1.7264 (11)C8C—H8CA0.9300
N1B—C5B1.3468 (14)C9C—C10C1.3839 (17)
N1B—C1B1.3543 (15)C9C—H9CA0.9300
N1B—H1NB0.92 (2)C10C—C11C1.3854 (16)
N2B—C5B1.3349 (15)C10C—H10B0.9300
N2B—H2NB0.865 (19)C11C—H11B0.9300
N2B—H3NB0.865 (19)O1X—C12X1.2170 (14)
C1B—C2B1.3618 (15)O2X—C12X1.3234 (14)
C1B—H1BA0.9300O2X—H1OX0.88 (2)
C2B—C3B1.4125 (15)O3X—C13X1.2088 (14)
C3B—C4B1.3666 (16)O4X—C13X1.3277 (13)
C3B—H3BA0.9300O4X—H2OX0.83 (2)
C4B—C5B1.4169 (15)C6X—C11X1.3938 (15)
C4B—H4BA0.9300C6X—C7X1.4043 (15)
O1B—C12B1.2266 (15)C6X—C12X1.5023 (15)
O2B—C12B1.2990 (15)C7X—C8X1.3971 (15)
O2B—H1OB0.8922C7X—C13X1.4928 (15)
O3B—C13B1.2698 (14)C8X—C9X1.3900 (16)
O4B—C13B1.2480 (14)C8X—H8XA0.9300
C6B—C11B1.4004 (16)C9X—C10X1.3903 (18)
C6B—C7B1.4198 (15)C9X—H9XA0.9300
C6B—C12B1.5208 (15)C10X—C11X1.3940 (16)
C7B—C8B1.3999 (15)C10X—H10A0.9300
C7B—C13B1.5242 (16)C11X—H11A0.9300
C8B—C9B1.3829 (16)
C5A—N1A—C1A122.94 (10)C11B—C10B—H10D120.4
C5A—N1A—H1NA120.8 (11)C10B—C11B—C6B122.47 (11)
C1A—N1A—H1NA116.2 (11)C10B—C11B—H11D118.8
C5A—N2A—H2NA118.7 (12)C6B—C11B—H11D118.8
C5A—N2A—H3NA121.1 (12)O1B—C12B—O2B120.49 (11)
H2NA—N2A—H3NA120.1 (16)O1B—C12B—C6B119.76 (11)
C2A—C1A—N1A120.19 (10)O2B—C12B—C6B119.73 (10)
C2A—C1A—H1AA119.9O4B—C13B—O3B122.28 (11)
N1A—C1A—H1AA119.9O4B—C13B—C7B117.01 (10)
C1A—C2A—C3A119.33 (10)O3B—C13B—C7B120.71 (10)
C1A—C2A—Cl1A119.37 (9)C5C—N1C—C1C122.59 (10)
C3A—C2A—Cl1A121.30 (9)C5C—N1C—H1NC119.0 (13)
C4A—C3A—C2A119.73 (10)C1C—N1C—H1NC118.4 (13)
C4A—C3A—H3AA120.1C5C—N2C—H2NC116.2 (12)
C2A—C3A—H3AA120.1C5C—N2C—H3NC119.9 (13)
C3A—C4A—C5A119.92 (10)H2NC—N2C—H3NC123.7 (17)
C3A—C4A—H4AA120.0N1C—C1C—C2C120.46 (10)
C5A—C4A—H4AA120.0N1C—C1C—H1CA119.8
N2A—C5A—N1A118.85 (10)C2C—C1C—H1CA119.8
N2A—C5A—C4A123.27 (10)C1C—C2C—C3C119.41 (10)
N1A—C5A—C4A117.88 (10)C1C—C2C—Cl1C119.03 (9)
C12A—O2A—H1OA110.8C3C—C2C—Cl1C121.55 (9)
C11A—C6A—C7A118.17 (10)C4C—C3C—C2C119.35 (11)
C11A—C6A—C12A113.49 (9)C4C—C3C—H3CA120.3
C7A—C6A—C12A128.33 (10)C2C—C3C—H3CA120.3
C8A—C7A—C6A118.26 (10)C3C—C4C—C5C120.09 (11)
C8A—C7A—C13A113.54 (9)C3C—C4C—H4CA120.0
C6A—C7A—C13A128.20 (10)C5C—C4C—H4CA120.0
C9A—C8A—C7A122.76 (10)N2C—C5C—N1C118.63 (10)
C9A—C8A—H8AA118.6N2C—C5C—C4C123.31 (11)
C7A—C8A—H8AA118.6N1C—C5C—C4C118.06 (10)
C8A—C9A—C10A119.01 (11)C12C—O2C—H2C109.5
C8A—C9A—H9AA120.5C11C—C6—C7C118.23 (10)
C10A—C9A—H9AA120.5C11C—C6—C12C113.09 (9)
C11A—C10A—C9A119.41 (10)C7C—C6—C12C128.68 (10)
C11A—C10A—H10C120.3C8C—C7C—C6118.07 (10)
C9A—C10A—H10C120.3C8C—C7C—C13C113.93 (9)
C10A—C11A—C6A122.38 (10)C6—C7C—C13C127.93 (10)
C10A—C11A—H11C118.8C9C—C8C—C7C122.41 (11)
C6A—C11A—H11C118.8C9C—C8C—H8CA118.8
O1A—C12A—O2A120.63 (11)C7C—C8C—H8CA118.8
O1A—C12A—C6A118.80 (10)C10C—C9C—C8C119.41 (11)
O2A—C12A—C6A120.53 (10)C10C—C9C—H9CA120.3
O4A—C13A—O3A122.55 (10)C8C—C9C—H9CA120.3
O4A—C13A—C7A116.75 (10)C9C—C10C—C11C119.34 (11)
O3A—C13A—C7A120.70 (10)C9C—C10C—H10B120.3
C5B—N1B—C1B122.49 (10)C11C—C10C—H10B120.3
C5B—N1B—H1NB120.8 (13)C10C—C11C—C6122.45 (11)
C1B—N1B—H1NB116.6 (13)C10C—C11C—H11B118.8
C5B—N2B—H2NB122.8 (12)C6—C11C—H11B118.8
C5B—N2B—H3NB114.2 (12)O1C—C12C—O2C120.72 (10)
H2NB—N2B—H3NB123.0 (17)O1C—C12C—C6117.77 (10)
N1B—C1B—C2B120.52 (10)O2C—C12C—C6121.51 (10)
N1B—C1B—H1BA119.7O4C—C13C—O3C121.99 (10)
C2B—C1B—H1BA119.7O4C—C13C—C7C117.77 (10)
C1B—C2B—C3B119.40 (10)O3C—C13C—C7C120.24 (10)
C1B—C2B—Cl1B118.85 (9)C12X—O2X—H1OX109.1 (12)
C3B—C2B—Cl1B121.73 (9)C13X—O4X—H2OX108.6 (14)
C4B—C3B—C2B119.05 (10)C11X—C6X—C7X119.87 (10)
C4B—C3B—H3BA120.5C11X—C6X—C12X117.43 (10)
C2B—C3B—H3BA120.5C7X—C6X—C12X122.66 (9)
C3B—C4B—C5B120.41 (10)C8X—C7X—C6X119.68 (10)
C3B—C4B—H4BA119.8C8X—C7X—C13X121.01 (10)
C5B—C4B—H4BA119.8C6X—C7X—C13X119.15 (9)
N2B—C5B—N1B119.18 (10)C9X—C8X—C7X120.18 (11)
N2B—C5B—C4B122.69 (10)C9X—C8X—H8XA119.9
N1B—C5B—C4B118.13 (10)C7X—C8X—H8XA119.9
C12B—O2B—H1OB110.9C8X—C9X—C10X119.94 (11)
C11B—C6B—C7B118.19 (10)C8X—C9X—H9XA120.0
C11B—C6B—C12B113.14 (10)C10X—C9X—H9XA120.0
C7B—C6B—C12B128.66 (10)C9X—C10X—C11X120.44 (11)
C8B—C7B—C6B118.08 (10)C9X—C10X—H10A119.8
C8B—C7B—C13B113.18 (10)C11X—C10X—H10A119.8
C6B—C7B—C13B128.74 (10)C6X—C11X—C10X119.82 (11)
C9B—C8B—C7B122.76 (11)C6X—C11X—H11A120.1
C9B—C8B—H8BA118.6C10X—C11X—H11A120.1
C7B—C8B—H8BA118.6O1X—C12X—O2X124.43 (10)
C8B—C9B—C10B119.23 (11)O1X—C12X—C6X123.11 (10)
C8B—C9B—H9BA120.4O2X—C12X—C6X112.32 (9)
C10B—C9B—H9BA120.4O3X—C13X—O4X123.32 (10)
C9B—C10B—C11B119.25 (11)O3X—C13X—C7X122.29 (10)
C9B—C10B—H10D120.4O4X—C13X—C7X114.38 (9)
C5A—N1A—C1A—C2A−0.11 (17)C7B—C6B—C12B—O2B3.60 (18)
N1A—C1A—C2A—C3A0.01 (17)C8B—C7B—C13B—O4B−7.92 (16)
N1A—C1A—C2A—Cl1A179.51 (8)C6B—C7B—C13B—O4B171.08 (12)
C1A—C2A—C3A—C4A−0.43 (17)C8B—C7B—C13B—O3B171.62 (11)
Cl1A—C2A—C3A—C4A−179.91 (9)C6B—C7B—C13B—O3B−9.37 (19)
C2A—C3A—C4A—C5A0.91 (17)C5C—N1C—C1C—C2C−1.30 (17)
C1A—N1A—C5A—N2A−179.42 (10)N1C—C1C—C2C—C3C−0.34 (17)
C1A—N1A—C5A—C4A0.59 (16)N1C—C1C—C2C—Cl1C−179.82 (9)
C3A—C4A—C5A—N2A179.02 (11)C1C—C2C—C3C—C4C0.94 (18)
C3A—C4A—C5A—N1A−0.99 (16)Cl1C—C2C—C3C—C4C−179.60 (9)
C11A—C6A—C7A—C8A−0.66 (15)C2C—C3C—C4C—C5C0.03 (18)
C12A—C6A—C7A—C8A178.68 (10)C1C—N1C—C5C—N2C−177.75 (11)
C11A—C6A—C7A—C13A178.97 (10)C1C—N1C—C5C—C4C2.23 (17)
C12A—C6A—C7A—C13A−1.68 (18)C3C—C4C—C5C—N2C178.42 (12)
C6A—C7A—C8A—C9A−0.18 (17)C3C—C4C—C5C—N1C−1.57 (17)
C13A—C7A—C8A—C9A−179.86 (10)C11C—C6—C7C—C8C−2.71 (15)
C7A—C8A—C9A—C10A0.61 (18)C12C—C6—C7C—C8C177.49 (10)
C8A—C9A—C10A—C11A−0.19 (17)C11C—C6—C7C—C13C173.98 (10)
C9A—C10A—C11A—C6A−0.68 (17)C12C—C6—C7C—C13C−5.82 (18)
C7A—C6A—C11A—C10A1.11 (16)C6—C7C—C8C—C9C2.13 (16)
C12A—C6A—C11A—C10A−178.34 (10)C13C—C7C—C8C—C9C−175.01 (10)
C11A—C6A—C12A—O1A−10.47 (15)C7C—C8C—C9C—C10C0.30 (18)
C7A—C6A—C12A—O1A170.16 (11)C8C—C9C—C10C—C11C−2.10 (18)
C11A—C6A—C12A—O2A167.19 (10)C9C—C10C—C11C—C61.46 (18)
C7A—C6A—C12A—O2A−12.18 (17)C7C—C6—C11C—C10C0.99 (17)
C8A—C7A—C13A—O4A4.03 (14)C12C—C6—C11C—C10C−179.18 (10)
C6A—C7A—C13A—O4A−175.62 (10)C11C—C6—C12C—O1C2.83 (14)
C8A—C7A—C13A—O3A−175.22 (10)C7C—C6—C12C—O1C−177.36 (11)
C6A—C7A—C13A—O3A5.13 (17)C11C—C6—C12C—O2C−177.53 (10)
C5B—N1B—C1B—C2B−0.22 (17)C7C—C6—C12C—O2C2.28 (17)
N1B—C1B—C2B—C3B0.16 (17)C8C—C7C—C13C—O4C4.56 (15)
N1B—C1B—C2B—Cl1B178.83 (8)C6—C7C—C13C—O4C−172.25 (11)
C1B—C2B—C3B—C4B−0.02 (17)C8C—C7C—C13C—O3C−175.82 (10)
Cl1B—C2B—C3B—C4B−178.65 (9)C6—C7C—C13C—O3C7.38 (17)
C2B—C3B—C4B—C5B−0.07 (17)C11X—C6X—C7X—C8X1.67 (16)
C1B—N1B—C5B—N2B−179.22 (11)C12X—C6X—C7X—C8X−175.84 (10)
C1B—N1B—C5B—C4B0.13 (16)C11X—C6X—C7X—C13X−173.77 (10)
C3B—C4B—C5B—N2B179.35 (11)C12X—C6X—C7X—C13X8.72 (16)
C3B—C4B—C5B—N1B0.02 (17)C6X—C7X—C8X—C9X0.65 (17)
C11B—C6B—C7B—C8B1.11 (16)C13X—C7X—C8X—C9X176.00 (10)
C12B—C6B—C7B—C8B−178.24 (11)C7X—C8X—C9X—C10X−2.29 (18)
C11B—C6B—C7B—C13B−177.86 (11)C8X—C9X—C10X—C11X1.62 (19)
C12B—C6B—C7B—C13B2.79 (19)C7X—C6X—C11X—C10X−2.34 (17)
C6B—C7B—C8B—C9B0.24 (18)C12X—C6X—C11X—C10X175.30 (11)
C13B—C7B—C8B—C9B179.36 (12)C9X—C10X—C11X—C6X0.70 (18)
C7B—C8B—C9B—C10B−1.2 (2)C11X—C6X—C12X—O1X64.87 (15)
C8B—C9B—C10B—C11B0.80 (19)C7X—C6X—C12X—O1X−117.57 (13)
C9B—C10B—C11B—C6B0.58 (19)C11X—C6X—C12X—O2X−110.99 (11)
C7B—C6B—C11B—C10B−1.54 (17)C7X—C6X—C12X—O2X66.58 (14)
C12B—C6B—C11B—C10B177.91 (11)C8X—C7X—C13X—O3X−160.33 (11)
C11B—C6B—C12B—O1B2.92 (16)C6X—C7X—C13X—O3X15.04 (16)
C7B—C6B—C12B—O1B−177.70 (12)C8X—C7X—C13X—O4X18.32 (15)
C11B—C6B—C12B—O2B−175.78 (11)C6X—C7X—C13X—O4X−166.30 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2C—H2C···O3C0.821.582.4004 (13)177
O2A—H1OA···O3A0.861.552.4123 (13)177
O2B—H1OB···O3B0.891.522.4126 (14)178
O2X—H1OX···O4C0.88 (2)1.76 (2)2.6091 (12)163 (2)
O4X—H2OX···O1Ai0.83 (2)1.86 (2)2.6880 (13)177 (2)
N2A—H2NA···O1Bii0.895 (18)2.018 (18)2.9095 (14)173.4 (19)
N1B—H1NB···O4Aiii0.92 (2)1.69 (2)2.5938 (14)169 (2)
N2B—H2NB···O3Aiii0.87 (2)2.12 (2)2.9570 (14)161.8 (17)
N1C—H1NC···O4B0.94 (2)1.69 (2)2.6169 (16)168 (2)
N2C—H3NC···O3B0.83 (2)2.11 (2)2.9279 (15)168.4 (19)
C4A—H4AA···O2Bii0.932.263.1614 (14)164

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2597).

References

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