research communications
Crystal structures of four isomeric hydrogen-bonded co-crystals of 6-methylquinoline with 2-chloro-4-nitrobenzoic acid, 2-chloro-5-nitrobenzoic acid, 3-chloro-2-nitrobenzoic acid and 4-chloro-2-nitrobenzoic acid
aDepartment of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, Japan
*Correspondence e-mail: ishidah@cc.okayama-u.ac.jp
The structures of the four isomeric compounds of 6-methylquinoline with chloro- and nitro-substituted benzoic acids, C7H4ClNO4·C10H9N, namely, 2-chloro-4-nitrobenzoic acid–6-methylquinoline (1/1), (I), 2-chloro-5-nitrobenzoic acid–6-methylquinoline (1/1), (II), 3-chloro-2-nitrobenzoic acid–6-methylquinoline (1/1), (III), and 4-chloro-2-nitrobenzoic acid–6-methylquinoline (1/1), (IV), have been determined at 185–190 K. In each compound, the acid and base molecules are linked by a short hydrogen bond between a carboxyl O atom and an N atom of the base. The O⋯N distances are 2.5452 (12), 2.6569 (13), 2.5640 (17) and 2.514 (2) Å, respectively, for compounds (I)–(IV). In the hydrogen-bonded acid–base units of (I), (III) and (IV), the H atoms are each disordered over two positions with O site:N site occupancies of 0.65 (3):0.35 (3), 0.59 (4):0.41 (4) and 0.48 (5):0.52 (5), respectively, for (I), (III) and (IV). The H atom in the hydrogen-bonded unit of (II) is located at the O-atom site. In all of the crystals of (I)–(IV), π–π interactions between the quinoline ring system and the benzene ring of the acid molecule are observed. In addition, a π–π interaction between the benzene rings of adjacent acid molecules and a C—H⋯O hydrogen bond are observed in the crystal of (I), and C—H⋯O hydrogen bonds and O⋯Cl contacts occur in the crystals of (III) and (IV). These intermolecular interactions connect the acid and base molecules, forming a layer structure parallel to the bc plane in (I), a column along the a-axis direction in (II), a layer parallel to the ab plane in (III) and a three-dimensional network in (IV). Hirshfeld surfaces for the title compounds mapped over dnorm and shape index were generated to visualize the weak intermolecular interactions.
1. Chemical context
Properties of hydrogen bonds formed between organic acids and organic bases depend on the pKa values of the acids and bases as well as intermolecular interactions in the crystals. In our ongoing study on crystal structures of the system of quinoline derivatives–chloro- and nitro-substituted benzoic acids, we have shown that three compounds of quinoline with 3-chloro-2-nitrobenzoic acid, 4-chloro-2-nitrobenzoic acid and 5-chloro-2-nitrobenzoic acid, the ΔpKa [pKa(base) − pKa(acid)] values of which are 3.08, 2.93 and 3.04, respectively, have a short double-well O—H⋯N/O⋯H—N hydrogen bond between the carboxy O atom and the aromatic N atom (Gotoh & Ishida, 2009). On the other hand, in 2-chloro-5-nitrobenzoic acid–quinoline (1/1) (ΔpKa = 2.68; Gotoh & Ishida, 2009), 2-chloro-4-nitrobenzoic acid–quinoline (1/1) (ΔpKa = 2.86; Gotoh & Ishida, 2011), 3-chloro-2-nitrobenzoic acid–6-nitroquinolune (1/1) (ΔpKa = 1.42), 8-hydroxyquinolinium 3-chloro-2-nitrobenzoate (ΔpKa = 3.02) and 3-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1) (ΔpKa = 0.98) (Gotoh & Ishida, 2019a), 2-chloro-4-nitrobenzoic acid–5-nitroquinoline (1/1) (ΔpKa = 0.76), 5-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1) (ΔpKa = 0.94) (Gotoh & Ishida, 2019b), such a short disordered hydrogen bond was not observed. We report here crystal structures of title four isomeric compounds, namely, 2-chloro-4-nitrobenzoic acid–6-methylquinoline (1/1), (I), 2-chloro-5-nitrobenzoic acid–6-methylquinoline (1/1), (II), 3-chloro-2-nitrobenzoic acid–6-methylquinoline (1/1), (III), and 4-chloro-2-nitrobenzoic acid–6-methylquinoline (1/1), (IV), in order to extend our studies of short hydrogen bonding and weak intermolecular interactions in the system of quinoline derivatives–chloro- and nitro-substituted benzoic acids. The ΔpKa values are 3.16, 2.98, 3.38 and 3.23, respectively, for (I)–(IV).
2. Structural commentary
The molecular structures of compounds (I)–(IV) are shown in Fig. 1. In each compound, the acid and base molecules are linked by a hydrogen bond between the carboxy group and the N atom of the base. In (I), (III) and (IV), short hydrogen bonds are observed with N⋯O distances of 2.5452 (12), 2.5640 (17) and 2.515 (2) Å, respectively. (Tables 1, 3 and 4). In these hydrogen bonds, the H atoms are each disordered over two sites; the occupancies of the O site and the N site refined to 0.65 (3) and 0.35 (3), 0.59 (4) and 0.41 (4), and 0.48 (5) and 0.52 (5), respectively, for (I), (III) and (IV). In (II), the H atom in the hydrogen bond is located at the O site with an N⋯O distance of 2.6569 (13) Å (Table 2), being longer than those in (I), (III) and (IV). Weak C—H⋯O hydrogen bonds are each observed in the acid–base unit of (II) (C15—H15⋯O2; Table 2) and the unit of (III) (C8—H8⋯O2; Table 3).
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In the hydrogen-bonded acid–base unit of compound (I), the quinoline ring system (N2/C8–C16) and the benzene ring (C1–C6) are almost coplanar with a dihedral angle of 1.11 (4)°, while the quinoline ring system and the carboxy group (O1/C7/O2) of the acid are twisted to each other with a dihedral angle of 28.59 (12)°. In the acid molecule, the benzene ring makes dihedral angles of 29.36 (12) and 8.24 (11)°, respectively, with the carboxy group and the nitro group (O3/N1/O4).
Similar to (I), the quinoline ring system (N2/C8–C16) in the hydrogen-bonded acid–base unit of (II) makes dihedral angles of 2.15 (4) and 24.51 (15)°, respectively, with the benzene ring and the carboxy group. The benzene ring makes dihedral angles of 22.63 (15) and 0.77 (14)°, respectively, with the carboxy group and the nitro group.
Compound (III) crystallizes in the non-centrosymmetric P212121. In the acid–base unit, the quinoline ring system and the benzene ring of the acid are slightly twisted to each other with a dihedral angle of 14.50 (5)°. The quinoline ring system and the carboxy group are also slightly twisted with a dihedral angle of 12.55 (18)°. The benzene ring makes dihedral angles of 3.14 (18) and 85.04 (11)°, respectively, with the carboxy group and the nitro group.
Compound (IV) crystallizes in the non-centrosymmetric Cc. In the acid–base unit, the quinoline ring system and the benzene ring of the acid are twisted to each other with a dihedral angle of 30.39 (9)°. The quinoline ring system and the carboxy group are also twisted with a dihedral angle of 21.7 (3)°. The benzene ring makes dihedral angles of 16.4 (3) and 74.4 (3)°, respectively, with the carboxy group and the nitro group.
3. Supramolecular features
In the crystal of (I), the hydrogen–bonded acid-base units are linked by a C—H⋯O hydrogen bond (C8—H8⋯O4i; symmetry code as given in Table 1), forming a zigzag chain propagating along the c-axis direction (Fig. 2). The acid–base units, which are related to each other by an inversion center, are linked together via π–π interactions between the quinoline ring system and the benzene ring of the acid molecule, forming a centrosymmetric dimeric unit (Fig. 3); the centroid–centroid distances are 3.7217 (6) and 3.7216 (6) Å, respectively, for Cg1⋯Cg2iii and Cg1⋯Cg3iii, where Cg1, Cg2 and Cg3 are the centroids of the C1–C6, N2/C8–C11/C16 and C11–C16 rings, respectively [symmetry code: (iii) −x + 1, −y + 1, −z + 1]. The dimeric units are further linked into a column structure stacked along the b-axis direction through a weak π–π interaction between the benzene rings with Cg1⋯Cg1iv = 3.9401 (6) Å [symmetry code: (iv) −x + 1, −y + 2, −z + 1]. The molecular chains are thus stacked into a layer parallel to the bc plane via these π–π interactions.
In the crystal of (II), the acid and base molecules are alternately stacked in a column via π–π interactions between the acid benzene ring and the quinoline ring system, so that the hydrogen-bonded acid–base units related by an inversion center are linked into a column structure along the a-axis direction (Fig. 4). The centroid–centroid distances are 3.6438 (6), 3.5745 (6), 3.6560 (6) and 3.7375 (6) Å, respectively, for Cg1⋯Cg2i, Cg1⋯Cg2ii, Cg1⋯Cg3i and Cg1⋯Cg3ii, where Cg1, Cg2 and Cg3 are the centroids of the C1–C6, N2/C8–C11/C16 and C11–C16 rings, respectively [symmetry codes: (i) −x, −y + 1, −z + 1; (ii) −x + 1, −y + 1, −z + 1]. There are no significant interactions between the columns.
In the crystal of (III), the hydrogen-bonded acid–base units are linked by a C—H⋯O hydrogen bond (C5—H5⋯O2i; symmetry code as in Table 3), forming a tape structure propagating along the b-axis direction (Fig. 5). The acid and base molecules are alternately stacked in a column along the a axis direction via π–π interactions between the acid ring and the quinoline ring system (Fig. 6), and thus the hydrogen-bonded acid–base units form a layer lying parallel to the ab plane. The centroid–centroid distances are 3.6415 (8), 3.6126 (8) and 3.6393 (8) Å, respectively, for Cg1⋯Cg2iii, Cg1⋯Cg3iii and Cg1⋯Cg3iv, where Cg1, Cg2 and Cg3 are the centroids of the C1–C6, N2/C8–C11/C16 and C11–C16 rings, respectively [symmetry codes: (iii) −x + 1, y + , −z + ; (iv) −x, y + , −z + ]. A short O⋯Cl contact [O3⋯Cl1v = 3.0934 (14) Å; symmetry code: (v) x − , −y + , −z] is observed between the layers.
In the crystal of (IV), the hydrogen-bonded acid–base units are linked into a zigzag chain structure propagating along the c-axis direction (Fig. 7) via C—H⋯O hydrogen bonds (C10—H10⋯O2i; symmetry code as in Table 4). The chains are further linked into a sheet parallel to the bc plane via an O⋯Cl short contact [O4⋯Cl1ii = 3.017 (3) Å; (ii) x, −y, z + ]. Similar to (III), the acid and base molecules are alternately stacked in a column along the a-axis direction via π–π interactions between the acid ring and the quinoline ring system (Fig. 8), and thus the above sheets form a three-dimensional network. The centroid–centroid distances are 3.5813 (13), 3.7987 (14) and 3.7382 (14) Å, respectively, for Cg1⋯Cg2iii, Cg1⋯Cg3iii and Cg1⋯Cg3iv, where Cg1, Cg2 and Cg3 are the centroids of the C1–C6, N2/C8–C11/C16 and C11–C16 rings, respectively [symmetry codes: (iii) x − , −y + , z − ; (iv) x + , −y + , z − ].
Hirshfeld surfaces for compounds (I)–(IV) mapped over dnorm and shape index (Turner et al., 2017; McKinnon et al., 2004, 2007) are shown in Fig. 9. The C—H⋯O interactions in (I), (III) and (IV) are viewed as faint-red spots on the dnorm surfaces (black arrows in Fig. 9). In addition to these interactions, the O⋯Cl contacts in (III) and (IV) are shown as faint-red spots (magenta arrows). The π–π interactions between the acid ring and the quinoline ring system in (I)–(IV) are indicated by blue and red triangles on the shape index surfaces (white circles in Fig. 9).
4. Database survey
A search of the Cambridge Structural Database (Version 5.41, last update May 2020; Groom et al., 2016) for organic co-crystals/salts of 6-methylquinoline with carboxylic acid derivatives showed two structures, namely, 6-methylquinoline hemikis(trans-but-2-enedioic acid) (Cambridge Structural Database refcode LASGUJ; Bekö et al., 2012), sesquikis(6-methylquinoline) hemikis(quinoline) trans-but-2-enedioic acid (LASHAQ; Beko et al., 2012). A search for organic co-crystals/salts of 2-chloro-4-nitrobenzoic acid, 2-chloro-5-nitrobenzoic acid, 3-chloro-2-nitrobenzoic acid and 4-chloro-2-nitrobenzoic acid gave 61, 12, 9 and 9 structures, respectively. Limiting the search for quinoline derivatives of these compounds gave 3, 2, 4 and 2 compounds, namely, for 2-chloro-4-nitrobenzoic acid: 2-chloro-4-nitrobenzoic acid–5-nitroquinoline (NUBHEA; Gotoh & Ishida, 2019b), 8-hydroxyquinolinium 2-chloro-4-nitrobenzoate (WOPDEM; Babu & Chandrasekaran, 2014), 2-chloro-4-nitrobenzoic acid–quinoline (1/1) (YAGFAP; Gotoh & Ishida, 2011), for 2-chloro-5-nitrobenzoic acid: 2-chloro-5-nitrobenzoic acid–quinoline (1/1) (AJIWIA; Gotoh & Ishida, 2009), 8-hydroxy-2-methylquinolinium 2-chloro-5-nitrobenzoate dihydrate (HIHPIY; Tan, 2007), for 3-chloro-2-nitrobenzoic acid: 3-chloro-2-nitrobenzoic acid–quinoline (1/1) (AJIWOG, Gotoh & Ishida, 2009), 3-chloro-2-nitrobenzoic acid–5-nitroquinoline (1/1) (XOWVUD; Gotoh & Ishida, 2019a), 3-chloro-2-nitrobenzoic acid–6-nitroquinoline (1/1) (XOWWAK, Gotoh & Ishida, 2019a), 8-hydroxyquinolin-1-ium 3-chloro-2-nitrobenzoate (XOWWEO; Gotoh & Ishida, 2019a), and for 4-chloro-2-nitrobenzoic acid: 4-chloro-2-nitrobenzoic acid–quinoline (AJIWUM; Gotoh & Ishida, 2009), 4-hydroxyquinolin-1-ium 4-chloro-2-nitrobenzoate (WOVZOZ; Gotoh & Ishida, 2019c). Of these compounds, AJIWOG and AJIWUM show disordered O—H⋯N/O⋯H—N hydrogen bonds, while WOVZOZ shows a disorder structure in the O—H⋯O hydrogen bond accompanied by a keto–enol in the base molecule.
5. Synthesis and crystallization
Single crystals of the title compounds (I)–(IV) were obtained by slow evaporation from acetonitrile solutions of 6-methylquinoline with chloro-nitrobenzoic acids in a 1:1 molar ratio at room temperature [80 ml acetonitrile solution of 6-methylquinoline (0.20 g) and chloro-nitrobenzoic acid (0.28 g for each acid)].
6. Refinement
Crystal data, data collection and structure . All H atoms in compounds (I)–(IV) were found in difference-Fourier maps. The O-bound H atom in (II) was refined freely; the refined distance is given in Table 2. For (I), (III) and (IV), H atoms in the N⋯H⋯O hydrogen bonds were found to be disordered over two positions in difference-Fourier maps. Since the site-occupancy factors and isotropic displacement parameters are strongly collated, the positional parameters and occupancy factors were refined, with bond length restraints of N—H = 0.88 (1) Å and O—H = 0.84 (1) Å, and with Uiso(H) = 1.5Ueq(N or O); the refined distances are given in Tables 1, 3 and 4. Other H atoms were positioned geometrically (C—H = 0.95 Å) and treated as riding, with Uiso(H) = 1.2 or 1.5Ueq(C).
details are summarized in Table 5
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Supporting information
https://doi.org/10.1107/S2056989020013134/hb7946sup1.cif
contains datablocks global, I, II, III, IV. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989020013134/hb7946Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989020013134/hb7946IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989020013134/hb7946IIIsup4.hkl
Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S2056989020013134/hb7946IVsup5.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989020013134/hb7946Isup6.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020013134/hb7946IIsup7.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020013134/hb7946IIIsup8.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989020013134/hb7946IVsup9.cml
For all structures, data collection: PROCESS-AUTO (Rigaku, 2006); cell
PROCESS-AUTO (Rigaku, 2006); data reduction: PROCESS-AUTO (Rigaku, 2006). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (I), (II); SHELXS97 (Sheldrick, 2008) for (III), (IV). Program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b) for (I); SHELXL-2018/3 (Sheldrick, 2015b) for (II); SHELXL2016/6 (Sheldrick, 2015b) for (III); SHELXL2016/6 (Sheldrick, 2015b) for (IV). For all structures, molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2020); software used to prepare material for publication: CrystalStructure (Rigaku, 2018) and PLATON (Spek, 2020).C7H3.65ClNO4·C10H9.35N | F(000) = 712.00 |
Mr = 344.74 | Dx = 1.489 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
a = 9.5055 (2) Å | Cell parameters from 26323 reflections |
b = 8.3019 (4) Å | θ = 3.1–30.2° |
c = 19.5865 (4) Å | µ = 0.27 mm−1 |
β = 95.7214 (7)° | T = 185 K |
V = 1537.94 (8) Å3 | Block, colorless |
Z = 4 | 0.40 × 0.35 × 0.35 mm |
Rigaku R-AXIS RAPIDII diffractometer | 4065 reflections with I > 2σ(I) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.025 |
ω scans | θmax = 30.0°, θmin = 3.2° |
Absorption correction: numerical (NUMABS; Higashi, 1999) | h = −13→12 |
Tmin = 0.887, Tmax = 0.909 | k = −11→11 |
30539 measured reflections | l = −27→26 |
4487 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: mixed |
wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0572P)2 + 0.329P] where P = (Fo2 + 2Fc2)/3 |
4487 reflections | (Δ/σ)max = 0.001 |
225 parameters | Δρmax = 0.43 e Å−3 |
2 restraints | Δρmin = −0.22 e Å−3 |
Primary atom site location: structure-invariant direct methods |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.87370 (3) | 0.79426 (3) | 0.44087 (2) | 0.03134 (8) | |
O1 | 0.42961 (8) | 0.64577 (11) | 0.42646 (5) | 0.03635 (19) | |
H1 | 0.401 (3) | 0.576 (3) | 0.3967 (11) | 0.055* | 0.65 (3) |
O2 | 0.64551 (9) | 0.55323 (11) | 0.41332 (5) | 0.0415 (2) | |
O3 | 0.85703 (9) | 1.17879 (11) | 0.64471 (4) | 0.03715 (19) | |
O4 | 0.67137 (9) | 1.12532 (11) | 0.69548 (4) | 0.03875 (19) | |
N1 | 0.74667 (9) | 1.10600 (10) | 0.64913 (4) | 0.02564 (17) | |
N2 | 0.32928 (9) | 0.44919 (10) | 0.33444 (4) | 0.02445 (16) | |
H2 | 0.364 (4) | 0.521 (4) | 0.3649 (17) | 0.037* | 0.35 (3) |
C1 | 0.61850 (9) | 0.76377 (11) | 0.49454 (4) | 0.02042 (16) | |
C2 | 0.75219 (9) | 0.83696 (11) | 0.49820 (4) | 0.02126 (17) | |
C3 | 0.79336 (9) | 0.95089 (11) | 0.54813 (5) | 0.02240 (17) | |
H3 | 0.883075 | 1.001906 | 0.549641 | 0.027* | |
C4 | 0.70028 (10) | 0.98778 (11) | 0.59541 (4) | 0.02162 (17) | |
C5 | 0.56791 (10) | 0.91744 (12) | 0.59456 (5) | 0.02394 (18) | |
H5 | 0.506368 | 0.944280 | 0.628184 | 0.029* | |
C6 | 0.52786 (10) | 0.80690 (11) | 0.54331 (5) | 0.02350 (18) | |
H6 | 0.436619 | 0.759387 | 0.541313 | 0.028* | |
C7 | 0.56641 (10) | 0.64206 (11) | 0.44026 (5) | 0.02361 (17) | |
C8 | 0.40800 (11) | 0.39905 (13) | 0.28726 (5) | 0.0284 (2) | |
H8 | 0.500827 | 0.441308 | 0.287010 | 0.034* | |
C9 | 0.36003 (12) | 0.28509 (13) | 0.23709 (5) | 0.0314 (2) | |
H9 | 0.418985 | 0.252719 | 0.203149 | 0.038* | |
C10 | 0.22700 (12) | 0.22130 (12) | 0.23779 (5) | 0.0291 (2) | |
H10 | 0.193332 | 0.143923 | 0.204340 | 0.035* | |
C11 | 0.14049 (10) | 0.27092 (11) | 0.28827 (5) | 0.02387 (18) | |
C12 | 0.00279 (11) | 0.20841 (12) | 0.29329 (5) | 0.0285 (2) | |
H12 | −0.034075 | 0.128787 | 0.261562 | 0.034* | |
C13 | −0.07753 (11) | 0.26074 (13) | 0.34293 (6) | 0.0294 (2) | |
C14 | −0.02173 (11) | 0.38120 (13) | 0.38945 (6) | 0.0299 (2) | |
H14 | −0.078279 | 0.419813 | 0.423309 | 0.036* | |
C15 | 0.11154 (11) | 0.44368 (12) | 0.38702 (5) | 0.02705 (19) | |
H15 | 0.146830 | 0.523118 | 0.419192 | 0.032* | |
C16 | 0.19535 (10) | 0.38878 (11) | 0.33634 (5) | 0.02220 (17) | |
C17 | −0.22358 (12) | 0.19441 (16) | 0.34909 (8) | 0.0408 (3) | |
H17A | −0.290638 | 0.283656 | 0.350772 | 0.061* | |
H17B | −0.222599 | 0.130421 | 0.391184 | 0.061* | |
H17C | −0.252335 | 0.126106 | 0.309332 | 0.061* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.02668 (13) | 0.03764 (15) | 0.03157 (13) | −0.00822 (9) | 0.01214 (9) | −0.01037 (9) |
O1 | 0.0247 (4) | 0.0378 (4) | 0.0445 (4) | 0.0002 (3) | −0.0067 (3) | −0.0172 (3) |
O2 | 0.0293 (4) | 0.0412 (5) | 0.0547 (5) | −0.0052 (3) | 0.0083 (3) | −0.0239 (4) |
O3 | 0.0343 (4) | 0.0387 (4) | 0.0387 (4) | −0.0130 (3) | 0.0050 (3) | −0.0133 (3) |
O4 | 0.0452 (5) | 0.0433 (5) | 0.0297 (4) | −0.0057 (4) | 0.0133 (3) | −0.0115 (3) |
N1 | 0.0282 (4) | 0.0247 (4) | 0.0239 (4) | −0.0008 (3) | 0.0022 (3) | −0.0028 (3) |
N2 | 0.0244 (4) | 0.0227 (4) | 0.0254 (4) | −0.0023 (3) | −0.0015 (3) | −0.0010 (3) |
C1 | 0.0196 (4) | 0.0194 (4) | 0.0219 (4) | −0.0016 (3) | 0.0006 (3) | 0.0011 (3) |
C2 | 0.0195 (4) | 0.0228 (4) | 0.0219 (4) | −0.0016 (3) | 0.0043 (3) | −0.0005 (3) |
C3 | 0.0197 (4) | 0.0235 (4) | 0.0241 (4) | −0.0042 (3) | 0.0024 (3) | −0.0010 (3) |
C4 | 0.0235 (4) | 0.0200 (4) | 0.0211 (4) | −0.0012 (3) | 0.0011 (3) | −0.0012 (3) |
C5 | 0.0219 (4) | 0.0258 (4) | 0.0247 (4) | −0.0006 (3) | 0.0055 (3) | −0.0004 (3) |
C6 | 0.0193 (4) | 0.0246 (4) | 0.0268 (4) | −0.0033 (3) | 0.0034 (3) | 0.0000 (3) |
C7 | 0.0247 (4) | 0.0213 (4) | 0.0247 (4) | −0.0042 (3) | 0.0019 (3) | −0.0004 (3) |
C8 | 0.0274 (4) | 0.0280 (5) | 0.0297 (5) | −0.0020 (4) | 0.0029 (4) | 0.0016 (4) |
C9 | 0.0375 (5) | 0.0320 (5) | 0.0256 (4) | 0.0002 (4) | 0.0072 (4) | −0.0014 (4) |
C10 | 0.0389 (5) | 0.0267 (5) | 0.0212 (4) | −0.0027 (4) | 0.0000 (4) | −0.0031 (3) |
C11 | 0.0276 (4) | 0.0214 (4) | 0.0214 (4) | −0.0014 (3) | −0.0038 (3) | 0.0008 (3) |
C12 | 0.0286 (5) | 0.0257 (4) | 0.0295 (5) | −0.0047 (3) | −0.0060 (4) | 0.0000 (3) |
C13 | 0.0238 (4) | 0.0268 (4) | 0.0366 (5) | −0.0010 (4) | −0.0017 (4) | 0.0065 (4) |
C14 | 0.0280 (5) | 0.0274 (5) | 0.0346 (5) | 0.0035 (4) | 0.0052 (4) | 0.0015 (4) |
C15 | 0.0292 (5) | 0.0234 (4) | 0.0282 (4) | 0.0006 (3) | 0.0011 (3) | −0.0032 (3) |
C16 | 0.0237 (4) | 0.0197 (4) | 0.0223 (4) | −0.0004 (3) | −0.0023 (3) | 0.0003 (3) |
C17 | 0.0269 (5) | 0.0399 (6) | 0.0553 (7) | −0.0065 (4) | 0.0026 (5) | 0.0073 (5) |
Cl1—C2 | 1.7262 (9) | C8—C9 | 1.4069 (14) |
O1—C7 | 1.3019 (12) | C8—H8 | 0.9500 |
O1—H1 | 0.847 (10) | C9—C10 | 1.3722 (16) |
O2—C7 | 1.2111 (13) | C9—H9 | 0.9500 |
O3—N1 | 1.2211 (12) | C10—C11 | 1.4091 (14) |
O4—N1 | 1.2215 (11) | C10—H10 | 0.9500 |
N1—C4 | 1.4739 (12) | C11—C12 | 1.4206 (14) |
N2—C8 | 1.3134 (13) | C11—C16 | 1.4205 (12) |
N2—C16 | 1.3722 (12) | C12—C13 | 1.3656 (16) |
N2—H2 | 0.883 (10) | C12—H12 | 0.9500 |
C1—C6 | 1.3954 (13) | C13—C14 | 1.4196 (15) |
C1—C2 | 1.4039 (12) | C13—C17 | 1.5096 (15) |
C1—C7 | 1.5137 (12) | C14—C15 | 1.3741 (15) |
C2—C3 | 1.3884 (12) | C14—H14 | 0.9500 |
C3—C4 | 1.3774 (13) | C15—C16 | 1.4090 (14) |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
C4—C5 | 1.3857 (13) | C17—H17A | 0.9800 |
C5—C6 | 1.3851 (13) | C17—H17B | 0.9800 |
C5—H5 | 0.9500 | C17—H17C | 0.9800 |
C6—H6 | 0.9500 | ||
C7—O1—H1 | 112.0 (19) | C10—C9—C8 | 119.17 (10) |
O3—N1—O4 | 123.98 (9) | C10—C9—H9 | 120.4 |
O3—N1—C4 | 118.49 (8) | C8—C9—H9 | 120.4 |
O4—N1—C4 | 117.53 (8) | C9—C10—C11 | 119.80 (9) |
C8—N2—C16 | 119.89 (8) | C9—C10—H10 | 120.1 |
C8—N2—H2 | 119 (3) | C11—C10—H10 | 120.1 |
C16—N2—H2 | 121 (3) | C10—C11—C12 | 123.23 (9) |
C6—C1—C2 | 118.13 (8) | C10—C11—C16 | 117.72 (9) |
C6—C1—C7 | 118.10 (8) | C12—C11—C16 | 119.05 (9) |
C2—C1—C7 | 123.77 (8) | C13—C12—C11 | 121.16 (9) |
C3—C2—C1 | 121.40 (8) | C13—C12—H12 | 119.4 |
C3—C2—Cl1 | 115.99 (7) | C11—C12—H12 | 119.4 |
C1—C2—Cl1 | 122.60 (7) | C12—C13—C14 | 118.79 (9) |
C4—C3—C2 | 118.04 (8) | C12—C13—C17 | 121.65 (10) |
C4—C3—H3 | 121.0 | C14—C13—C17 | 119.56 (10) |
C2—C3—H3 | 121.0 | C15—C14—C13 | 122.03 (10) |
C3—C4—C5 | 122.79 (8) | C15—C14—H14 | 119.0 |
C3—C4—N1 | 117.48 (8) | C13—C14—H14 | 119.0 |
C5—C4—N1 | 119.73 (8) | C14—C15—C16 | 119.36 (9) |
C6—C5—C4 | 118.14 (8) | C14—C15—H15 | 120.3 |
C6—C5—H5 | 120.9 | C16—C15—H15 | 120.3 |
C4—C5—H5 | 120.9 | N2—C16—C15 | 119.48 (8) |
C5—C6—C1 | 121.48 (8) | N2—C16—C11 | 120.93 (9) |
C5—C6—H6 | 119.3 | C15—C16—C11 | 119.59 (9) |
C1—C6—H6 | 119.3 | C13—C17—H17A | 109.5 |
O2—C7—O1 | 125.07 (9) | C13—C17—H17B | 109.5 |
O2—C7—C1 | 122.59 (9) | H17A—C17—H17B | 109.5 |
O1—C7—C1 | 112.34 (8) | C13—C17—H17C | 109.5 |
N2—C8—C9 | 122.47 (9) | H17A—C17—H17C | 109.5 |
N2—C8—H8 | 118.8 | H17B—C17—H17C | 109.5 |
C9—C8—H8 | 118.8 | ||
C6—C1—C2—C3 | −0.91 (13) | C16—N2—C8—C9 | 0.66 (15) |
C7—C1—C2—C3 | 178.41 (8) | N2—C8—C9—C10 | −1.13 (16) |
C6—C1—C2—Cl1 | −179.86 (7) | C8—C9—C10—C11 | 0.25 (16) |
C7—C1—C2—Cl1 | −0.55 (13) | C9—C10—C11—C12 | −178.73 (9) |
C1—C2—C3—C4 | 1.56 (14) | C9—C10—C11—C16 | 0.97 (14) |
Cl1—C2—C3—C4 | −179.42 (7) | C10—C11—C12—C13 | −179.69 (9) |
C2—C3—C4—C5 | −0.70 (14) | C16—C11—C12—C13 | 0.62 (14) |
C2—C3—C4—N1 | 178.55 (8) | C11—C12—C13—C14 | 0.77 (15) |
O3—N1—C4—C3 | 8.31 (13) | C11—C12—C13—C17 | −179.57 (9) |
O4—N1—C4—C3 | −171.89 (9) | C12—C13—C14—C15 | −1.57 (16) |
O3—N1—C4—C5 | −172.41 (9) | C17—C13—C14—C15 | 178.76 (10) |
O4—N1—C4—C5 | 7.39 (13) | C13—C14—C15—C16 | 0.91 (15) |
C3—C4—C5—C6 | −0.78 (14) | C8—N2—C16—C15 | −179.81 (9) |
N1—C4—C5—C6 | 179.98 (8) | C8—N2—C16—C11 | 0.65 (14) |
C4—C5—C6—C1 | 1.46 (14) | C14—C15—C16—N2 | −179.02 (9) |
C2—C1—C6—C5 | −0.64 (14) | C14—C15—C16—C11 | 0.53 (14) |
C7—C1—C6—C5 | 180.00 (8) | C10—C11—C16—N2 | −1.45 (13) |
C6—C1—C7—O2 | −151.53 (10) | C12—C11—C16—N2 | 178.26 (9) |
C2—C1—C7—O2 | 29.15 (15) | C10—C11—C16—C15 | 179.01 (9) |
C6—C1—C7—O1 | 28.79 (12) | C12—C11—C16—C15 | −1.28 (13) |
C2—C1—C7—O1 | −150.52 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.85 (2) | 1.70 (2) | 2.5452 (12) | 174 (3) |
N2—H2···O1 | 0.88 (3) | 1.66 (3) | 2.5452 (12) | 176 (3) |
C8—H8···O4i | 0.95 | 2.59 | 3.2307 (13) | 125 |
Symmetry code: (i) x, −y+3/2, z−1/2. |
C7H4ClNO4·C10H9N | Z = 2 |
Mr = 344.74 | F(000) = 356.00 |
Triclinic, P1 | Dx = 1.517 Mg m−3 |
a = 6.8693 (3) Å | Mo Kα radiation, λ = 0.71075 Å |
b = 7.6482 (4) Å | Cell parameters from 13517 reflections |
c = 15.1195 (4) Å | θ = 3.1–30.1° |
α = 78.218 (3)° | µ = 0.28 mm−1 |
β = 81.1923 (18)° | T = 186 K |
γ = 77.754 (3)° | Block, colorless |
V = 754.89 (6) Å3 | 0.45 × 0.35 × 0.30 mm |
Rigaku R-AXIS RAPIDII diffractometer | 3868 reflections with I > 2σ(I) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.023 |
ω scans | θmax = 30.0°, θmin = 3.1° |
Absorption correction: numerical (NUMABS; Higashi, 1999) | h = −9→9 |
Tmin = 0.891, Tmax = 0.920 | k = −10→10 |
15404 measured reflections | l = −20→21 |
4381 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: mixed |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0662P)2 + 0.1585P] where P = (Fo2 + 2Fc2)/3 |
4381 reflections | (Δ/σ)max = 0.001 |
222 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.11678 (4) | 0.98086 (4) | 0.61864 (2) | 0.03561 (10) | |
O1 | 0.21038 (15) | 0.43541 (12) | 0.54709 (6) | 0.0366 (2) | |
O2 | 0.28610 (18) | 0.71213 (14) | 0.49895 (6) | 0.0478 (3) | |
O3 | 0.18489 (15) | 0.29378 (13) | 0.96192 (6) | 0.0392 (2) | |
O4 | 0.25163 (16) | 0.14131 (12) | 0.85221 (6) | 0.0405 (2) | |
N1 | 0.20962 (14) | 0.28451 (13) | 0.88057 (6) | 0.02681 (18) | |
N2 | 0.29763 (14) | 0.34416 (12) | 0.38322 (6) | 0.02569 (18) | |
C1 | 0.19890 (14) | 0.60827 (13) | 0.65842 (7) | 0.02253 (19) | |
C2 | 0.15118 (15) | 0.77299 (14) | 0.69035 (7) | 0.02393 (19) | |
C3 | 0.12289 (16) | 0.77660 (14) | 0.78333 (7) | 0.0264 (2) | |
H3 | 0.091426 | 0.890115 | 0.803551 | 0.032* | |
C4 | 0.14004 (15) | 0.61713 (14) | 0.84642 (7) | 0.0254 (2) | |
H4 | 0.119312 | 0.619066 | 0.909822 | 0.030* | |
C5 | 0.18819 (14) | 0.45521 (13) | 0.81441 (6) | 0.02191 (18) | |
C6 | 0.21638 (15) | 0.44738 (13) | 0.72259 (7) | 0.02259 (19) | |
H6 | 0.247515 | 0.333038 | 0.703216 | 0.027* | |
C7 | 0.23535 (16) | 0.59389 (15) | 0.55899 (7) | 0.0274 (2) | |
C8 | 0.34550 (16) | 0.16678 (15) | 0.38795 (7) | 0.0279 (2) | |
H8 | 0.346849 | 0.091817 | 0.446377 | 0.033* | |
C9 | 0.39475 (17) | 0.08253 (14) | 0.31103 (8) | 0.0284 (2) | |
H9 | 0.429397 | −0.046122 | 0.317664 | 0.034* | |
C10 | 0.39200 (16) | 0.18891 (14) | 0.22624 (7) | 0.0267 (2) | |
H10 | 0.424134 | 0.134301 | 0.173486 | 0.032* | |
C11 | 0.34115 (14) | 0.38015 (13) | 0.21768 (7) | 0.02121 (18) | |
C12 | 0.33604 (15) | 0.50006 (14) | 0.13253 (7) | 0.02423 (19) | |
H12 | 0.364652 | 0.451051 | 0.078062 | 0.029* | |
C13 | 0.29069 (15) | 0.68496 (14) | 0.12730 (7) | 0.02410 (19) | |
C14 | 0.24533 (16) | 0.75428 (14) | 0.20953 (8) | 0.0271 (2) | |
H14 | 0.212931 | 0.882237 | 0.206693 | 0.032* | |
C15 | 0.24652 (16) | 0.64331 (14) | 0.29307 (7) | 0.0264 (2) | |
H15 | 0.214505 | 0.694420 | 0.346914 | 0.032* | |
C16 | 0.29544 (14) | 0.45298 (13) | 0.29885 (6) | 0.02121 (18) | |
C17 | 0.28690 (19) | 0.81553 (17) | 0.03801 (8) | 0.0341 (2) | |
H17A | 0.323370 | 0.747133 | −0.012173 | 0.051* | |
H17B | 0.382979 | 0.895687 | 0.034211 | 0.051* | |
H17C | 0.151890 | 0.888699 | 0.033913 | 0.051* | |
H1 | 0.243 (3) | 0.420 (3) | 0.4899 (15) | 0.064 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.03973 (16) | 0.02267 (14) | 0.03659 (16) | −0.00175 (10) | −0.00100 (11) | 0.00595 (10) |
O1 | 0.0568 (6) | 0.0320 (4) | 0.0209 (4) | −0.0110 (4) | 0.0014 (3) | −0.0059 (3) |
O2 | 0.0815 (8) | 0.0429 (5) | 0.0220 (4) | −0.0271 (5) | −0.0024 (4) | 0.0010 (4) |
O3 | 0.0584 (6) | 0.0364 (5) | 0.0194 (4) | −0.0069 (4) | −0.0037 (3) | 0.0005 (3) |
O4 | 0.0648 (6) | 0.0216 (4) | 0.0315 (4) | −0.0031 (4) | −0.0064 (4) | −0.0010 (3) |
N1 | 0.0315 (4) | 0.0243 (4) | 0.0227 (4) | −0.0046 (3) | −0.0038 (3) | 0.0002 (3) |
N2 | 0.0299 (4) | 0.0250 (4) | 0.0208 (4) | −0.0049 (3) | −0.0029 (3) | −0.0012 (3) |
C1 | 0.0227 (4) | 0.0234 (5) | 0.0203 (4) | −0.0042 (3) | −0.0029 (3) | −0.0012 (3) |
C2 | 0.0222 (4) | 0.0215 (4) | 0.0262 (5) | −0.0043 (3) | −0.0032 (3) | 0.0007 (3) |
C3 | 0.0291 (5) | 0.0209 (4) | 0.0292 (5) | −0.0040 (4) | −0.0023 (4) | −0.0061 (4) |
C4 | 0.0278 (5) | 0.0265 (5) | 0.0221 (4) | −0.0054 (4) | −0.0022 (3) | −0.0050 (4) |
C5 | 0.0233 (4) | 0.0213 (4) | 0.0202 (4) | −0.0048 (3) | −0.0034 (3) | −0.0001 (3) |
C6 | 0.0250 (4) | 0.0213 (4) | 0.0208 (4) | −0.0038 (3) | −0.0027 (3) | −0.0028 (3) |
C7 | 0.0303 (5) | 0.0297 (5) | 0.0212 (5) | −0.0052 (4) | −0.0042 (4) | −0.0016 (4) |
C8 | 0.0298 (5) | 0.0249 (5) | 0.0269 (5) | −0.0066 (4) | −0.0042 (4) | 0.0027 (4) |
C9 | 0.0310 (5) | 0.0183 (4) | 0.0347 (5) | −0.0046 (4) | −0.0040 (4) | −0.0015 (4) |
C10 | 0.0308 (5) | 0.0201 (4) | 0.0293 (5) | −0.0050 (4) | −0.0006 (4) | −0.0065 (4) |
C11 | 0.0217 (4) | 0.0193 (4) | 0.0226 (4) | −0.0049 (3) | −0.0014 (3) | −0.0035 (3) |
C12 | 0.0274 (5) | 0.0250 (5) | 0.0203 (4) | −0.0060 (4) | −0.0013 (3) | −0.0039 (3) |
C13 | 0.0252 (4) | 0.0234 (5) | 0.0230 (5) | −0.0067 (4) | −0.0047 (3) | 0.0010 (3) |
C14 | 0.0326 (5) | 0.0188 (4) | 0.0298 (5) | −0.0035 (4) | −0.0067 (4) | −0.0033 (4) |
C15 | 0.0335 (5) | 0.0209 (5) | 0.0249 (5) | −0.0023 (4) | −0.0043 (4) | −0.0064 (4) |
C16 | 0.0223 (4) | 0.0204 (4) | 0.0206 (4) | −0.0042 (3) | −0.0024 (3) | −0.0028 (3) |
C17 | 0.0424 (6) | 0.0308 (5) | 0.0268 (5) | −0.0099 (5) | −0.0071 (4) | 0.0059 (4) |
Cl1—C2 | 1.7245 (10) | C8—C9 | 1.4055 (16) |
O1—C7 | 1.3106 (14) | C8—H8 | 0.9500 |
O1—H1 | 0.89 (2) | C9—C10 | 1.3713 (15) |
O2—C7 | 1.2104 (14) | C9—H9 | 0.9500 |
O3—N1 | 1.2302 (12) | C10—C11 | 1.4134 (13) |
O4—N1 | 1.2192 (13) | C10—H10 | 0.9500 |
N1—C5 | 1.4686 (13) | C11—C16 | 1.4149 (13) |
N2—C8 | 1.3161 (14) | C11—C12 | 1.4205 (13) |
N2—C16 | 1.3737 (12) | C12—C13 | 1.3705 (14) |
C1—C2 | 1.3972 (14) | C12—H12 | 0.9500 |
C1—C6 | 1.3984 (13) | C13—C14 | 1.4157 (15) |
C1—C7 | 1.5084 (14) | C13—C17 | 1.5066 (14) |
C2—C3 | 1.3946 (15) | C14—C15 | 1.3706 (15) |
C3—C4 | 1.3819 (15) | C14—H14 | 0.9500 |
C3—H3 | 0.9500 | C15—C16 | 1.4103 (14) |
C4—C5 | 1.3781 (14) | C15—H15 | 0.9500 |
C4—H4 | 0.9500 | C17—H17A | 0.9800 |
C5—C6 | 1.3838 (14) | C17—H17B | 0.9800 |
C6—H6 | 0.9500 | C17—H17C | 0.9800 |
C7—O1—H1 | 112.6 (13) | C10—C9—H9 | 120.5 |
O4—N1—O3 | 123.42 (10) | C8—C9—H9 | 120.5 |
O4—N1—C5 | 118.51 (9) | C9—C10—C11 | 119.73 (10) |
O3—N1—C5 | 118.07 (9) | C9—C10—H10 | 120.1 |
C8—N2—C16 | 118.47 (9) | C11—C10—H10 | 120.1 |
C2—C1—C6 | 117.92 (9) | C10—C11—C16 | 117.36 (9) |
C2—C1—C7 | 123.90 (9) | C10—C11—C12 | 123.30 (9) |
C6—C1—C7 | 118.17 (9) | C16—C11—C12 | 119.33 (9) |
C3—C2—C1 | 120.97 (9) | C13—C12—C11 | 121.38 (9) |
C3—C2—Cl1 | 116.41 (8) | C13—C12—H12 | 119.3 |
C1—C2—Cl1 | 122.59 (8) | C11—C12—H12 | 119.3 |
C4—C3—C2 | 120.83 (10) | C12—C13—C14 | 118.14 (9) |
C4—C3—H3 | 119.6 | C12—C13—C17 | 122.58 (10) |
C2—C3—H3 | 119.6 | C14—C13—C17 | 119.27 (10) |
C5—C4—C3 | 117.86 (9) | C15—C14—C13 | 122.32 (9) |
C5—C4—H4 | 121.1 | C15—C14—H14 | 118.8 |
C3—C4—H4 | 121.1 | C13—C14—H14 | 118.8 |
C4—C5—C6 | 122.59 (9) | C14—C15—C16 | 119.78 (9) |
C4—C5—N1 | 118.54 (9) | C14—C15—H15 | 120.1 |
C6—C5—N1 | 118.86 (9) | C16—C15—H15 | 120.1 |
C5—C6—C1 | 119.81 (9) | N2—C16—C15 | 118.88 (9) |
C5—C6—H6 | 120.1 | N2—C16—C11 | 122.08 (9) |
C1—C6—H6 | 120.1 | C15—C16—C11 | 119.03 (9) |
O2—C7—O1 | 124.98 (10) | C13—C17—H17A | 109.5 |
O2—C7—C1 | 123.97 (10) | C13—C17—H17B | 109.5 |
O1—C7—C1 | 111.02 (9) | H17A—C17—H17B | 109.5 |
N2—C8—C9 | 123.38 (10) | C13—C17—H17C | 109.5 |
N2—C8—H8 | 118.3 | H17A—C17—H17C | 109.5 |
C9—C8—H8 | 118.3 | H17B—C17—H17C | 109.5 |
C10—C9—C8 | 118.97 (10) | ||
C6—C1—C2—C3 | 0.31 (15) | C16—N2—C8—C9 | 0.03 (16) |
C7—C1—C2—C3 | −178.82 (10) | N2—C8—C9—C10 | −0.48 (17) |
C6—C1—C2—Cl1 | −177.73 (7) | C8—C9—C10—C11 | 0.35 (16) |
C7—C1—C2—Cl1 | 3.14 (14) | C9—C10—C11—C16 | 0.19 (15) |
C1—C2—C3—C4 | −0.43 (16) | C9—C10—C11—C12 | 179.57 (10) |
Cl1—C2—C3—C4 | 177.73 (8) | C10—C11—C12—C13 | −178.37 (10) |
C2—C3—C4—C5 | 0.75 (16) | C16—C11—C12—C13 | 0.99 (15) |
C3—C4—C5—C6 | −1.02 (16) | C11—C12—C13—C14 | −1.05 (15) |
C3—C4—C5—N1 | 179.20 (9) | C11—C12—C13—C17 | 179.13 (9) |
O4—N1—C5—C4 | 179.79 (10) | C12—C13—C14—C15 | 0.36 (16) |
O3—N1—C5—C4 | −0.50 (15) | C17—C13—C14—C15 | −179.82 (10) |
O4—N1—C5—C6 | −0.01 (15) | C13—C14—C15—C16 | 0.40 (16) |
O3—N1—C5—C6 | 179.71 (10) | C8—N2—C16—C15 | −179.29 (10) |
C4—C5—C6—C1 | 0.93 (16) | C8—N2—C16—C11 | 0.55 (15) |
N1—C5—C6—C1 | −179.29 (8) | C14—C15—C16—N2 | 179.39 (9) |
C2—C1—C6—C5 | −0.54 (15) | C14—C15—C16—C11 | −0.45 (15) |
C7—C1—C6—C5 | 178.64 (9) | C10—C11—C16—N2 | −0.65 (14) |
C2—C1—C7—O2 | 23.08 (17) | C12—C11—C16—N2 | 179.94 (9) |
C6—C1—C7—O2 | −156.05 (12) | C10—C11—C16—C15 | 179.19 (9) |
C2—C1—C7—O1 | −158.73 (10) | C12—C11—C16—C15 | −0.22 (14) |
C6—C1—C7—O1 | 22.14 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.89 (2) | 1.78 (2) | 2.6569 (13) | 169 (2) |
C15—H15···O2 | 0.95 | 2.46 | 3.3211 (14) | 151 |
C7H3.59ClNO4·C10H9.41N | Dx = 1.470 Mg m−3 |
Mr = 344.75 | Mo Kα radiation, λ = 0.71075 Å |
Orthorhombic, P212121 | Cell parameters from 28109 reflections |
a = 7.1156 (4) Å | θ = 3.0–30.0° |
b = 7.5854 (4) Å | µ = 0.27 mm−1 |
c = 28.8599 (14) Å | T = 190 K |
V = 1557.70 (14) Å3 | Block, colorless |
Z = 4 | 0.30 × 0.30 × 0.17 mm |
F(000) = 712.00 |
Rigaku R-AXIS RAPIDII diffractometer | 4365 reflections with I > 2σ(I) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.017 |
ω scans | θmax = 30.0°, θmin = 3.0° |
Absorption correction: numerical (NUMABS; Higashi, 1999) | h = −10→9 |
Tmin = 0.938, Tmax = 0.955 | k = −10→10 |
30061 measured reflections | l = −39→40 |
4532 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.079 | w = 1/[σ2(Fo2) + (0.0546P)2 + 0.1455P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
4532 reflections | Δρmax = 0.31 e Å−3 |
225 parameters | Δρmin = −0.26 e Å−3 |
2 restraints | Absolute structure: Flack x determined using 1821 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.014 (8) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.53139 (7) | 0.88067 (5) | 0.01741 (2) | 0.03788 (11) | |
O1 | 0.27295 (18) | 0.75649 (15) | 0.22566 (4) | 0.0324 (2) | |
H1 | 0.236 (6) | 0.671 (4) | 0.2421 (12) | 0.049* | 0.59 (4) |
O2 | 0.3168 (2) | 0.54391 (16) | 0.17307 (4) | 0.0419 (3) | |
O3 | 0.2617 (2) | 0.56590 (17) | 0.07241 (4) | 0.0410 (3) | |
O4 | 0.55968 (19) | 0.53587 (15) | 0.08592 (5) | 0.0385 (3) | |
N1 | 0.41299 (18) | 0.61877 (16) | 0.08702 (4) | 0.0263 (2) | |
N2 | 0.18381 (18) | 0.49896 (17) | 0.27884 (4) | 0.0260 (2) | |
H2 | 0.203 (8) | 0.585 (5) | 0.2590 (16) | 0.039* | 0.41 (4) |
C1 | 0.37616 (18) | 0.84027 (16) | 0.15112 (4) | 0.0210 (2) | |
C2 | 0.42073 (19) | 0.80125 (17) | 0.10505 (4) | 0.0216 (2) | |
C3 | 0.4747 (2) | 0.93226 (17) | 0.07416 (4) | 0.0240 (2) | |
C4 | 0.4842 (2) | 1.10660 (18) | 0.08878 (5) | 0.0265 (3) | |
H4 | 0.520281 | 1.196857 | 0.067766 | 0.032* | |
C5 | 0.4404 (2) | 1.14758 (18) | 0.13447 (5) | 0.0272 (3) | |
H5 | 0.446936 | 1.266384 | 0.144760 | 0.033* | |
C6 | 0.38715 (19) | 1.01549 (18) | 0.16517 (5) | 0.0246 (2) | |
H6 | 0.357703 | 1.045362 | 0.196302 | 0.030* | |
C7 | 0.3188 (2) | 0.69810 (18) | 0.18471 (5) | 0.0245 (3) | |
C8 | 0.2211 (2) | 0.3372 (2) | 0.26449 (5) | 0.0297 (3) | |
H8 | 0.261320 | 0.320660 | 0.233404 | 0.036* | |
C9 | 0.2039 (2) | 0.18918 (19) | 0.29319 (5) | 0.0307 (3) | |
H9 | 0.229500 | 0.074532 | 0.281546 | 0.037* | |
C10 | 0.1493 (2) | 0.21234 (19) | 0.33840 (5) | 0.0282 (3) | |
H10 | 0.138409 | 0.113530 | 0.358444 | 0.034* | |
C11 | 0.10940 (18) | 0.38383 (19) | 0.35510 (4) | 0.0234 (2) | |
C12 | 0.0566 (2) | 0.4191 (2) | 0.40170 (5) | 0.0269 (3) | |
H12 | 0.046576 | 0.324225 | 0.423028 | 0.032* | |
C13 | 0.0200 (2) | 0.5876 (2) | 0.41648 (5) | 0.0283 (3) | |
C14 | 0.0319 (2) | 0.7280 (2) | 0.38397 (5) | 0.0311 (3) | |
H14 | 0.003183 | 0.844465 | 0.393774 | 0.037* | |
C15 | 0.0841 (2) | 0.69943 (19) | 0.33867 (5) | 0.0292 (3) | |
H15 | 0.091762 | 0.795472 | 0.317624 | 0.035* | |
C16 | 0.12609 (19) | 0.52672 (18) | 0.32360 (5) | 0.0233 (2) | |
C17 | −0.0287 (3) | 0.6272 (3) | 0.46621 (5) | 0.0399 (4) | |
H17A | −0.128360 | 0.716224 | 0.467272 | 0.060* | |
H17B | 0.082912 | 0.671801 | 0.482279 | 0.060* | |
H17C | −0.072283 | 0.519138 | 0.481428 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0610 (2) | 0.03165 (18) | 0.02096 (15) | −0.00237 (17) | 0.01009 (15) | 0.00035 (13) |
O1 | 0.0498 (7) | 0.0250 (5) | 0.0223 (5) | −0.0041 (5) | 0.0099 (5) | −0.0005 (4) |
O2 | 0.0751 (9) | 0.0223 (5) | 0.0282 (5) | −0.0037 (5) | 0.0160 (6) | 0.0008 (4) |
O3 | 0.0507 (7) | 0.0332 (6) | 0.0390 (6) | −0.0137 (5) | −0.0115 (5) | −0.0032 (5) |
O4 | 0.0478 (6) | 0.0249 (5) | 0.0427 (6) | 0.0058 (5) | 0.0072 (5) | −0.0060 (5) |
N1 | 0.0391 (6) | 0.0201 (5) | 0.0197 (5) | −0.0037 (5) | 0.0015 (4) | −0.0007 (4) |
N2 | 0.0325 (6) | 0.0245 (5) | 0.0209 (5) | −0.0020 (5) | 0.0034 (4) | 0.0025 (4) |
C1 | 0.0240 (5) | 0.0193 (5) | 0.0199 (5) | −0.0003 (4) | 0.0020 (4) | 0.0011 (4) |
C2 | 0.0258 (5) | 0.0173 (5) | 0.0215 (5) | −0.0005 (4) | 0.0004 (4) | −0.0006 (4) |
C3 | 0.0298 (6) | 0.0222 (5) | 0.0198 (5) | 0.0002 (5) | 0.0032 (5) | 0.0012 (4) |
C4 | 0.0324 (6) | 0.0197 (5) | 0.0274 (6) | −0.0006 (5) | 0.0027 (5) | 0.0033 (5) |
C5 | 0.0341 (7) | 0.0187 (5) | 0.0289 (6) | 0.0012 (5) | 0.0029 (5) | −0.0017 (5) |
C6 | 0.0300 (6) | 0.0210 (5) | 0.0228 (6) | 0.0017 (5) | 0.0037 (5) | −0.0021 (5) |
C7 | 0.0302 (6) | 0.0226 (6) | 0.0209 (6) | −0.0012 (5) | 0.0038 (5) | 0.0029 (5) |
C8 | 0.0375 (7) | 0.0289 (7) | 0.0227 (6) | −0.0030 (6) | 0.0033 (5) | −0.0012 (5) |
C9 | 0.0409 (8) | 0.0219 (6) | 0.0292 (7) | −0.0017 (6) | 0.0016 (6) | −0.0021 (5) |
C10 | 0.0349 (7) | 0.0229 (6) | 0.0268 (6) | −0.0034 (5) | 0.0005 (5) | 0.0030 (5) |
C11 | 0.0247 (5) | 0.0238 (5) | 0.0218 (5) | −0.0027 (5) | −0.0009 (4) | 0.0023 (5) |
C12 | 0.0293 (6) | 0.0307 (7) | 0.0207 (6) | −0.0033 (5) | 0.0006 (5) | 0.0043 (5) |
C13 | 0.0275 (6) | 0.0346 (7) | 0.0228 (6) | −0.0013 (5) | 0.0025 (5) | −0.0005 (5) |
C14 | 0.0346 (7) | 0.0273 (6) | 0.0313 (7) | 0.0020 (6) | 0.0062 (6) | −0.0014 (5) |
C15 | 0.0356 (7) | 0.0229 (6) | 0.0291 (6) | 0.0008 (5) | 0.0051 (6) | 0.0034 (5) |
C16 | 0.0246 (5) | 0.0234 (6) | 0.0220 (6) | −0.0013 (4) | 0.0012 (5) | 0.0022 (5) |
C17 | 0.0464 (9) | 0.0483 (9) | 0.0251 (7) | 0.0006 (8) | 0.0071 (6) | −0.0055 (7) |
Cl1—C3 | 1.7316 (13) | C8—C9 | 1.401 (2) |
O1—C7 | 1.3035 (17) | C8—H8 | 0.9500 |
O1—H1 | 0.847 (13) | C9—C10 | 1.372 (2) |
O2—C7 | 1.2170 (18) | C9—H9 | 0.9500 |
O3—N1 | 1.2238 (18) | C10—C11 | 1.416 (2) |
O4—N1 | 1.2189 (18) | C10—H10 | 0.9500 |
N1—C2 | 1.4797 (17) | C11—C16 | 1.4197 (18) |
N2—C8 | 1.322 (2) | C11—C12 | 1.4217 (18) |
N2—C16 | 1.3717 (17) | C12—C13 | 1.372 (2) |
N2—H2 | 0.879 (14) | C12—H12 | 0.9500 |
C1—C6 | 1.3918 (18) | C13—C14 | 1.421 (2) |
C1—C2 | 1.3986 (17) | C13—C17 | 1.507 (2) |
C1—C7 | 1.5065 (18) | C14—C15 | 1.376 (2) |
C2—C3 | 1.3890 (17) | C14—H14 | 0.9500 |
C3—C4 | 1.3899 (19) | C15—C16 | 1.4124 (19) |
C4—C5 | 1.3900 (19) | C15—H15 | 0.9500 |
C4—H4 | 0.9500 | C17—H17A | 0.9800 |
C5—C6 | 1.3902 (19) | C17—H17B | 0.9800 |
C5—H5 | 0.9500 | C17—H17C | 0.9800 |
C6—H6 | 0.9500 | ||
C7—O1—H1 | 109 (3) | C10—C9—C8 | 118.97 (14) |
O4—N1—O3 | 125.11 (13) | C10—C9—H9 | 120.5 |
O4—N1—C2 | 117.38 (12) | C8—C9—H9 | 120.5 |
O3—N1—C2 | 117.42 (13) | C9—C10—C11 | 119.86 (13) |
C8—N2—C16 | 119.84 (12) | C9—C10—H10 | 120.1 |
C8—N2—H2 | 117 (4) | C11—C10—H10 | 120.1 |
C16—N2—H2 | 123 (4) | C10—C11—C16 | 117.81 (12) |
C6—C1—C2 | 117.80 (11) | C10—C11—C12 | 123.23 (13) |
C6—C1—C7 | 120.75 (11) | C16—C11—C12 | 118.95 (13) |
C2—C1—C7 | 121.45 (11) | C13—C12—C11 | 121.31 (13) |
C3—C2—C1 | 121.42 (12) | C13—C12—H12 | 119.3 |
C3—C2—N1 | 117.00 (11) | C11—C12—H12 | 119.3 |
C1—C2—N1 | 121.58 (11) | C12—C13—C14 | 118.75 (13) |
C2—C3—C4 | 119.96 (12) | C12—C13—C17 | 121.67 (14) |
C2—C3—Cl1 | 120.65 (10) | C14—C13—C17 | 119.56 (15) |
C4—C3—Cl1 | 119.39 (10) | C15—C14—C13 | 121.68 (14) |
C3—C4—C5 | 119.33 (12) | C15—C14—H14 | 119.2 |
C3—C4—H4 | 120.3 | C13—C14—H14 | 119.2 |
C5—C4—H4 | 120.3 | C14—C15—C16 | 119.71 (13) |
C4—C5—C6 | 120.30 (12) | C14—C15—H15 | 120.1 |
C4—C5—H5 | 119.9 | C16—C15—H15 | 120.1 |
C6—C5—H5 | 119.9 | N2—C16—C15 | 119.72 (12) |
C5—C6—C1 | 121.19 (12) | N2—C16—C11 | 120.72 (12) |
C5—C6—H6 | 119.4 | C15—C16—C11 | 119.55 (12) |
C1—C6—H6 | 119.4 | C13—C17—H17A | 109.5 |
O2—C7—O1 | 125.02 (13) | C13—C17—H17B | 109.5 |
O2—C7—C1 | 120.90 (12) | H17A—C17—H17B | 109.5 |
O1—C7—C1 | 114.08 (12) | C13—C17—H17C | 109.5 |
N2—C8—C9 | 122.77 (13) | H17A—C17—H17C | 109.5 |
N2—C8—H8 | 118.6 | H17B—C17—H17C | 109.5 |
C9—C8—H8 | 118.6 | ||
C6—C1—C2—C3 | 0.1 (2) | C2—C1—C7—O1 | −176.81 (13) |
C7—C1—C2—C3 | −179.62 (13) | C16—N2—C8—C9 | 0.2 (2) |
C6—C1—C2—N1 | 180.00 (13) | N2—C8—C9—C10 | −1.2 (3) |
C7—C1—C2—N1 | 0.25 (19) | C8—C9—C10—C11 | 0.8 (2) |
O4—N1—C2—C3 | 83.25 (16) | C9—C10—C11—C16 | 0.6 (2) |
O3—N1—C2—C3 | −93.42 (16) | C9—C10—C11—C12 | −178.41 (14) |
O4—N1—C2—C1 | −96.63 (16) | C10—C11—C12—C13 | 179.70 (14) |
O3—N1—C2—C1 | 86.70 (17) | C16—C11—C12—C13 | 0.7 (2) |
C1—C2—C3—C4 | −0.4 (2) | C11—C12—C13—C14 | 1.2 (2) |
N1—C2—C3—C4 | 179.77 (13) | C11—C12—C13—C17 | −177.59 (14) |
C1—C2—C3—Cl1 | 179.38 (10) | C12—C13—C14—C15 | −1.8 (2) |
N1—C2—C3—Cl1 | −0.49 (18) | C17—C13—C14—C15 | 177.06 (15) |
C2—C3—C4—C5 | 0.4 (2) | C13—C14—C15—C16 | 0.4 (2) |
Cl1—C3—C4—C5 | −179.37 (11) | C8—N2—C16—C15 | −179.21 (15) |
C3—C4—C5—C6 | −0.2 (2) | C8—N2—C16—C11 | 1.3 (2) |
C4—C5—C6—C1 | 0.0 (2) | C14—C15—C16—N2 | −177.94 (14) |
C2—C1—C6—C5 | 0.1 (2) | C14—C15—C16—C11 | 1.6 (2) |
C7—C1—C6—C5 | 179.82 (13) | C10—C11—C16—N2 | −1.7 (2) |
C6—C1—C7—O2 | −176.84 (16) | C12—C11—C16—N2 | 177.42 (13) |
C2—C1—C7—O2 | 2.9 (2) | C10—C11—C16—C15 | 178.81 (14) |
C6—C1—C7—O1 | 3.4 (2) | C12—C11—C16—C15 | −2.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.85 (3) | 1.72 (3) | 2.5640 (17) | 174 (3) |
N2—H2···O1 | 0.88 (4) | 1.69 (4) | 2.5640 (17) | 170 (4) |
C5—H5···.O2i | 0.95 | 2.44 | 3.3245 (19) | 155 |
C8—H8···.O2 | 0.95 | 2.46 | 3.1438 (19) | 129 |
Symmetry code: (i) x, y+1, z. |
C7H3.48ClNO4·C10H9.52N | F(000) = 712.00 |
Mr = 344.75 | Dx = 1.433 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71075 Å |
a = 7.4271 (6) Å | Cell parameters from 14736 reflections |
b = 14.4348 (6) Å | θ = 3.1–30.2° |
c = 16.2208 (7) Å | µ = 0.26 mm−1 |
β = 113.203 (3)° | T = 185 K |
V = 1598.35 (16) Å3 | Block, colorless |
Z = 4 | 0.28 × 0.25 × 0.20 mm |
Rigaku R-AXIS RAPIDII diffractometer | 4158 reflections with I > 2σ(I) |
Detector resolution: 10.000 pixels mm-1 | Rint = 0.015 |
ω scans | θmax = 30.0°, θmin = 3.1° |
Absorption correction: numerical (NUMABS; Higashi, 1999) | h = −10→10 |
Tmin = 0.931, Tmax = 0.949 | k = −19→20 |
16695 measured reflections | l = −22→22 |
4645 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0529P)2 + 0.1089P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
4645 reflections | Δρmax = 0.35 e Å−3 |
225 parameters | Δρmin = −0.16 e Å−3 |
4 restraints | Absolute structure: Flack x determined using 1899 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.023 (9) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.60068 (7) | 0.04982 (4) | 0.11442 (3) | 0.04410 (14) | |
O1 | 0.5629 (2) | 0.26210 (10) | 0.47141 (9) | 0.0398 (3) | |
H1 | 0.543 (10) | 0.290 (4) | 0.512 (3) | 0.060* | 0.48 (5) |
O2 | 0.5224 (3) | 0.38723 (10) | 0.38416 (11) | 0.0448 (4) | |
O3 | 0.8822 (3) | 0.13730 (13) | 0.49214 (11) | 0.0557 (5) | |
O4 | 0.6225 (5) | 0.05352 (14) | 0.45694 (15) | 0.0794 (8) | |
N1 | 0.7212 (3) | 0.11139 (11) | 0.44056 (12) | 0.0423 (4) | |
N2 | 0.5616 (2) | 0.36395 (11) | 0.59693 (10) | 0.0297 (3) | |
H2 | 0.543 (8) | 0.336 (3) | 0.546 (2) | 0.044* | 0.52 (5) |
C1 | 0.5733 (3) | 0.23966 (12) | 0.33064 (11) | 0.0274 (3) | |
C2 | 0.6451 (3) | 0.14958 (13) | 0.34899 (12) | 0.0292 (3) | |
C3 | 0.6568 (3) | 0.09002 (13) | 0.28407 (13) | 0.0325 (4) | |
H3 | 0.708220 | 0.029174 | 0.298910 | 0.039* | |
C4 | 0.5909 (3) | 0.12266 (15) | 0.19705 (12) | 0.0322 (4) | |
C5 | 0.5203 (3) | 0.21248 (15) | 0.17566 (12) | 0.0339 (4) | |
H5 | 0.478690 | 0.234289 | 0.115740 | 0.041* | |
C6 | 0.5111 (3) | 0.26997 (13) | 0.24225 (12) | 0.0311 (4) | |
H6 | 0.461428 | 0.331090 | 0.227361 | 0.037* | |
C7 | 0.5518 (3) | 0.30391 (14) | 0.39964 (12) | 0.0306 (4) | |
C8 | 0.5951 (3) | 0.45366 (13) | 0.59630 (12) | 0.0317 (4) | |
H8 | 0.593525 | 0.481201 | 0.542828 | 0.038* | |
C9 | 0.6328 (3) | 0.50947 (13) | 0.67162 (14) | 0.0353 (4) | |
H9 | 0.653792 | 0.574126 | 0.669007 | 0.042* | |
C10 | 0.6390 (3) | 0.46968 (13) | 0.74905 (13) | 0.0337 (4) | |
H10 | 0.666629 | 0.506454 | 0.801199 | 0.040* | |
C11 | 0.6041 (3) | 0.37319 (12) | 0.75145 (12) | 0.0282 (3) | |
C12 | 0.6091 (3) | 0.32621 (16) | 0.82941 (12) | 0.0350 (4) | |
H12 | 0.637854 | 0.360018 | 0.883369 | 0.042* | |
C13 | 0.5730 (3) | 0.23282 (16) | 0.82796 (15) | 0.0391 (4) | |
C14 | 0.5312 (3) | 0.18307 (15) | 0.74760 (17) | 0.0401 (4) | |
H14 | 0.506395 | 0.118429 | 0.746653 | 0.048* | |
C15 | 0.5253 (3) | 0.22500 (13) | 0.67141 (14) | 0.0354 (4) | |
H15 | 0.496495 | 0.189993 | 0.618127 | 0.042* | |
C16 | 0.5625 (2) | 0.32146 (13) | 0.67232 (12) | 0.0277 (3) | |
C17 | 0.5805 (4) | 0.1813 (2) | 0.9099 (2) | 0.0549 (6) | |
H17A | 0.456380 | 0.148651 | 0.896253 | 0.082* | |
H17B | 0.601873 | 0.225362 | 0.958894 | 0.082* | |
H17C | 0.688173 | 0.136438 | 0.928067 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0500 (3) | 0.0567 (3) | 0.0311 (2) | −0.0080 (2) | 0.02182 (19) | −0.0170 (2) |
O1 | 0.0611 (9) | 0.0370 (7) | 0.0260 (6) | 0.0069 (7) | 0.0223 (6) | −0.0011 (5) |
O2 | 0.0707 (11) | 0.0298 (7) | 0.0430 (8) | −0.0030 (7) | 0.0322 (8) | −0.0026 (6) |
O3 | 0.0667 (11) | 0.0593 (10) | 0.0284 (7) | 0.0180 (9) | 0.0052 (7) | 0.0040 (7) |
O4 | 0.149 (2) | 0.0547 (11) | 0.0454 (10) | −0.0336 (13) | 0.0493 (13) | 0.0042 (9) |
N1 | 0.0760 (13) | 0.0273 (8) | 0.0260 (7) | 0.0026 (8) | 0.0226 (8) | 0.0006 (6) |
N2 | 0.0320 (8) | 0.0326 (7) | 0.0246 (7) | 0.0054 (6) | 0.0113 (6) | −0.0020 (6) |
C1 | 0.0325 (8) | 0.0297 (8) | 0.0230 (7) | −0.0069 (7) | 0.0140 (6) | −0.0037 (6) |
C2 | 0.0370 (9) | 0.0307 (9) | 0.0214 (7) | −0.0053 (7) | 0.0133 (6) | −0.0006 (6) |
C3 | 0.0390 (9) | 0.0319 (9) | 0.0300 (8) | −0.0065 (7) | 0.0172 (7) | −0.0048 (7) |
C4 | 0.0333 (9) | 0.0428 (10) | 0.0243 (8) | −0.0098 (7) | 0.0154 (7) | −0.0110 (7) |
C5 | 0.0347 (9) | 0.0468 (10) | 0.0216 (7) | −0.0056 (8) | 0.0124 (7) | −0.0003 (7) |
C6 | 0.0314 (9) | 0.0365 (9) | 0.0261 (8) | −0.0038 (7) | 0.0122 (7) | 0.0016 (7) |
C7 | 0.0332 (9) | 0.0344 (9) | 0.0268 (8) | −0.0046 (7) | 0.0145 (7) | −0.0047 (7) |
C8 | 0.0341 (8) | 0.0350 (9) | 0.0271 (9) | 0.0064 (7) | 0.0133 (8) | 0.0056 (7) |
C9 | 0.0411 (10) | 0.0260 (8) | 0.0386 (9) | 0.0021 (7) | 0.0153 (8) | 0.0004 (8) |
C10 | 0.0389 (9) | 0.0304 (8) | 0.0304 (9) | 0.0030 (7) | 0.0120 (7) | −0.0064 (7) |
C11 | 0.0293 (8) | 0.0309 (8) | 0.0249 (7) | 0.0040 (6) | 0.0113 (6) | −0.0001 (6) |
C12 | 0.0363 (10) | 0.0443 (10) | 0.0258 (8) | 0.0066 (8) | 0.0137 (7) | 0.0039 (8) |
C13 | 0.0313 (9) | 0.0474 (11) | 0.0418 (10) | 0.0093 (8) | 0.0177 (8) | 0.0178 (9) |
C14 | 0.0342 (10) | 0.0320 (9) | 0.0546 (12) | 0.0012 (8) | 0.0180 (9) | 0.0083 (9) |
C15 | 0.0365 (10) | 0.0286 (8) | 0.0395 (10) | 0.0007 (7) | 0.0133 (8) | −0.0044 (7) |
C16 | 0.0269 (8) | 0.0289 (8) | 0.0273 (8) | 0.0037 (6) | 0.0108 (6) | −0.0006 (7) |
C17 | 0.0506 (13) | 0.0653 (15) | 0.0552 (14) | 0.0110 (11) | 0.0276 (11) | 0.0320 (12) |
Cl1—C4 | 1.7273 (18) | C8—C9 | 1.397 (3) |
O1—C7 | 1.285 (2) | C8—H8 | 0.9500 |
O1—H1 | 0.836 (15) | C9—C10 | 1.365 (3) |
O2—C7 | 1.230 (3) | C9—H9 | 0.9500 |
O3—N1 | 1.217 (3) | C10—C11 | 1.420 (3) |
O4—N1 | 1.208 (3) | C10—H10 | 0.9500 |
N1—C2 | 1.472 (2) | C11—C16 | 1.410 (2) |
N2—C8 | 1.319 (2) | C11—C12 | 1.423 (3) |
N2—C16 | 1.365 (2) | C12—C13 | 1.373 (3) |
N2—H2 | 0.873 (14) | C12—H12 | 0.9500 |
C1—C6 | 1.392 (2) | C13—C14 | 1.411 (3) |
C1—C2 | 1.392 (3) | C13—C17 | 1.505 (3) |
C1—C7 | 1.510 (2) | C14—C15 | 1.361 (3) |
C2—C3 | 1.389 (3) | C14—H14 | 0.9500 |
C3—C4 | 1.382 (3) | C15—C16 | 1.418 (3) |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
C4—C5 | 1.390 (3) | C17—H17A | 0.9800 |
C5—C6 | 1.385 (3) | C17—H17B | 0.9800 |
C5—H5 | 0.9500 | C17—H17C | 0.9800 |
C6—H6 | 0.9500 | ||
C7—O1—H1 | 122 (5) | C10—C9—C8 | 118.99 (17) |
O4—N1—O3 | 125.3 (2) | C10—C9—H9 | 120.5 |
O4—N1—C2 | 117.1 (2) | C8—C9—H9 | 120.5 |
O3—N1—C2 | 117.46 (18) | C9—C10—C11 | 119.82 (17) |
C8—N2—C16 | 120.89 (15) | C9—C10—H10 | 120.1 |
C8—N2—H2 | 113 (4) | C11—C10—H10 | 120.1 |
C16—N2—H2 | 126 (4) | C16—C11—C10 | 118.13 (16) |
C6—C1—C2 | 117.21 (16) | C16—C11—C12 | 118.45 (17) |
C6—C1—C7 | 118.77 (16) | C10—C11—C12 | 123.42 (17) |
C2—C1—C7 | 123.97 (16) | C13—C12—C11 | 121.08 (18) |
C3—C2—C1 | 123.32 (17) | C13—C12—H12 | 119.5 |
C3—C2—N1 | 114.79 (16) | C11—C12—H12 | 119.5 |
C1—C2—N1 | 121.85 (16) | C12—C13—C14 | 119.07 (18) |
C4—C3—C2 | 117.43 (18) | C12—C13—C17 | 122.1 (2) |
C4—C3—H3 | 121.3 | C14—C13—C17 | 118.9 (2) |
C2—C3—H3 | 121.3 | C15—C14—C13 | 121.93 (19) |
C3—C4—C5 | 121.32 (17) | C15—C14—H14 | 119.0 |
C3—C4—Cl1 | 118.61 (16) | C13—C14—H14 | 119.0 |
C5—C4—Cl1 | 120.06 (14) | C14—C15—C16 | 119.38 (19) |
C6—C5—C4 | 119.59 (16) | C14—C15—H15 | 120.3 |
C6—C5—H5 | 120.2 | C16—C15—H15 | 120.3 |
C4—C5—H5 | 120.2 | N2—C16—C11 | 119.95 (16) |
C5—C6—C1 | 121.10 (18) | N2—C16—C15 | 119.96 (16) |
C5—C6—H6 | 119.4 | C11—C16—C15 | 120.08 (17) |
C1—C6—H6 | 119.4 | C13—C17—H17A | 109.5 |
O2—C7—O1 | 125.94 (17) | C13—C17—H17B | 109.5 |
O2—C7—C1 | 120.75 (16) | H17A—C17—H17B | 109.5 |
O1—C7—C1 | 113.29 (16) | C13—C17—H17C | 109.5 |
N2—C8—C9 | 122.19 (16) | H17A—C17—H17C | 109.5 |
N2—C8—H8 | 118.9 | H17B—C17—H17C | 109.5 |
C9—C8—H8 | 118.9 | ||
C6—C1—C2—C3 | 0.0 (3) | C16—N2—C8—C9 | 0.0 (3) |
C7—C1—C2—C3 | 177.39 (18) | N2—C8—C9—C10 | 1.3 (3) |
C6—C1—C2—N1 | 177.83 (18) | C8—C9—C10—C11 | −1.0 (3) |
C7—C1—C2—N1 | −4.8 (3) | C9—C10—C11—C16 | −0.4 (3) |
O4—N1—C2—C3 | −73.6 (3) | C9—C10—C11—C12 | 179.57 (18) |
O3—N1—C2—C3 | 102.9 (2) | C16—C11—C12—C13 | −0.5 (3) |
O4—N1—C2—C1 | 108.3 (2) | C10—C11—C12—C13 | 179.59 (19) |
O3—N1—C2—C1 | −75.1 (3) | C11—C12—C13—C14 | 0.3 (3) |
C1—C2—C3—C4 | −0.9 (3) | C11—C12—C13—C17 | 179.03 (19) |
N1—C2—C3—C4 | −178.83 (17) | C12—C13—C14—C15 | −0.1 (3) |
C2—C3—C4—C5 | 1.6 (3) | C17—C13—C14—C15 | −178.90 (19) |
C2—C3—C4—Cl1 | −179.20 (14) | C13—C14—C15—C16 | 0.1 (3) |
C3—C4—C5—C6 | −1.6 (3) | C8—N2—C16—C11 | −1.4 (3) |
Cl1—C4—C5—C6 | 179.26 (14) | C8—N2—C16—C15 | 179.73 (18) |
C4—C5—C6—C1 | 0.7 (3) | C10—C11—C16—N2 | 1.6 (3) |
C2—C1—C6—C5 | 0.1 (3) | C12—C11—C16—N2 | −178.32 (16) |
C7—C1—C6—C5 | −177.44 (17) | C10—C11—C16—C15 | −179.54 (18) |
C6—C1—C7—O2 | −16.2 (3) | C12—C11—C16—C15 | 0.5 (3) |
C2—C1—C7—O2 | 166.48 (19) | C14—C15—C16—N2 | 178.48 (17) |
C6—C1—C7—O1 | 162.34 (17) | C14—C15—C16—C11 | −0.4 (3) |
C2—C1—C7—O1 | −15.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.84 (7) | 1.70 (6) | 2.514 (2) | 163 (7) |
N2—H2···O1 | 0.87 (4) | 1.67 (5) | 2.514 (2) | 162 (4) |
C10—H10···O2i | 0.95 | 2.54 | 3.364 (3) | 145 |
Symmetry code: (i) x, −y+1, z+1/2. |
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