research communications
The structures of eleven (4-phenyl)piperazinium salts containing organic anions
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570 006, India, bInstitute of Materials Science, Darmstadt University of Technology, Alarich-Weiss-Strasse 2, D-64287 Darmstadt, Germany, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA
*Correspondence e-mail: yathirajan@hotmail.com
Eleven (4-phenyl)piperazinium salts containing organic anions have been prepared and structurally characterized, namely, 4-phenylpiperazin-1-ium 4-fluorobenzoate monohydrate, C10H15N2+·C7H4FO2−·H2O, 1; 4-phenylpiperazin-1-ium 4-bromobenzoate monohydrate, C10H15N2+·C7H4BrO2−·H2O, 3; 4-phenylpiperazin-1-ium 4-iodobenzoate, C10H15N2+·C7H4IO2−, 4; 4-phenylpiperazin-1-ium 4-nitrobenzoate, C10H15N2+·C7H4NO4−, 5; 4-phenylpiperazin-1-ium 3,5-dinitrosalicylate, C10H15N2+·C7H3N2O7−, 6; 4-phenylpiperazin-1-ium 3,5-dinitrobenzoate, C10H15N2+·C7H3N2O6−, 7; 4-phenylpiperazin-1-ium picrate, C10H15N2+·C6H2N3O7−, 8; 4-phenylpiperazin-1-ium benzoate monohydrate, C10H15N2+·C7H5O2−·H2O, 9; 4-phenylpiperazin-1-ium p-toluenesulfonate, C10H15N2+·C7H7O3S−, 10; 4-phenylpiperazin-1-ium tartarate monohydrate, C10H15N2+·C4H5O6−·H2O, 11; and 4-phenylpiperazin-1-ium fumarate, C10H15N2+·C4H3O4−, 12. Compounds 1 and 3–12 are all 1:1 salts with the acid proton transferred to the phenylpiperaizine basic N atom (the secondary amine) with the exception of 3 where there is disorder in the proton position with it being 68% attached to the base and 32% attached to the acid. Of the structures with similar stoichiometries only 3 and 9 are isomorphous. The 4-phenyl substituent in all cases occupies an equatorial position except for 12 where it is in an axial position. The crystal chosen for structure 7 was refined as a non-merohedral twin. There is disorder in 5, 6, 10 and 11. For both 5 and 6, a nitro group is disordered and was modeled with two equivalent orientations with occupancies of 0.62 (3)/0.38 (3) and 0.690 (11)/0.310 (11), respectively. For 6, 10 and 11, this disorder is associated with the phenyl ring of the phenylpiperazinium cation with occupancies of 0.687 (10)/0.313 (10), 0.51 (7)/0.49 (7) and 0.611 (13)/389 (13), respectively. For all salts, the packing is dominated by the N—H⋯O hydrogen bonds formed by the cation and anion. In addition, several structures contain C—H⋯π (1, 3, 4, 8, 9, 10, and 12) and aromatic π–π stacking interactions (6 and 8) and one structure (5) contains a –NO2⋯π interaction. For all structures, the Hirshfeld surface fingerprint plots show the expected prominent spikes as a result of the N—H⋯O and O—H⋯O hydrogen bonds.
Keywords: crystal structure; phenylpiperazinium cation; organic salt.
1. Chemical context
The pharmacological properties of phenylpiperazines and their derivatives have been described by various researchers (Cohen et al. 1982; Conrado et al. 2010; Neves et al. 2003; Hanano et al. 2000). The design and synthesis of phenylpiperazine derivatives as potent anticancer agents for prostate cancer have been reported (Demirci et al., 2019). Many pharmaceutical compounds are derived from 1-phenylpiperazine, including oxypertine (Archer et al., 1962), trazodone (Alhaider, 1992) and nefazodone. Derivatives of 1-phenylpiperazine have shown other interesting properties, such as (C10H15N2)+4(Pb3Cl10)4– where dielectric relaxation spectroscopy has shown different molecular motions and measurements of AC conductivity as a function of frequency at different temperatures indicated a hopping conduction mechanism (Mathlouthi et al., 2017) and new organic–inorganic hybrid materials of formula (C10H15N2)7(Sb2Cl10)(Sb2Cl9)(SbCl5)2(SbCl4)2Cl·7H2O (Lahbib et al., 2017).
As part of our ongoing studies of hydrogen-bonding patterns in molecular salts (Sagar et al., 2017; Kiran Kumar et al., 2019a,b, 2020, Harish Chinthal et al., 2020), the present paper reports the syntheses and crystal structures of eleven molecular salts of 1-phenylpiperazine, C10H14N2, viz.: 4-phenylpiperazin-1-ium 4-fluorobenzoate monohydrate, C10H15N2+·C7H4FO2−·H2O, 1; phenylpiperazin-1-ium 4-bromobenzoate monohydrate, C10H15N2+·C7H4BrO2−·H2O, 3; phenylpiperazin-1-ium 4-iodobenzoate, C10H15N2+·C7H4IO2−, 4; phenylpiperazin-1-ium 4-nitrobenzoate, C10H15N2+·C7H4NO4−, 5; phenylpiperazin-1-ium 3,5-dinitrosalicylate, C10H15N2+·C7H3N2O7−, 6; phenylpiperazin-1-ium 3,5-dinitrobenzoate, C10H15N2+·C7H3N2O6−, 7; phenylpiperazin-1-ium picrate, C10H15N2+·C6H2N3O7−, 8; phenylpiperazin-1-ium benzoate monohydrate, C10H15N2+·C7H5O2−·H2O, 9; phenylpiperazin-1-ium p-toluenesulfonate, C10H15N2+·C7H7O3S−, 10; phenylpiperazin-1-ium tartarate monohydrate, C10H15N2+·C4H5O6−·H2O, 11; and phenylpiperazin-1-ium fumarate, C10H15N2+·C4H3O4−, 12.
2. Structural commentary
Compounds 1 and 3–12 (Figs. 1–11) are all 1:1 molecular salts with the acid proton transferred to the secondary N atom of the phenylpiperaizine base with the exception of 3 where there is disorder in the proton position with it being 68% attached to the base and 32% attached to the acid. Compounds 1, 3 and 9 crystallize as mono-hydrates but the remaining crystals are solvent free. In compounds 1, 3, 4, 5 and 9, the anions are all benzoate ions or p-substituted benzoates but only 3 and 9 are isomorphous. Compounds 6, 7 and 8 contain picrate or nitrated benzoate anions while 10 contains a tosylate anion and 11 and 12 contain hydrogen tartarate and hydrogen fumarate mono-anions. Apart from the disorder in the acidic proton position mentioned above, there is disorder in 5, 6, 10 and 11. For 5 this disorder is confined to the nitro substituent on the benzoate anion, which is disordered over two orientations with occupancies of 0.62 (3)/0.38 (2). For 6, 10 and 11 the disorder is associated with the phenyl ring of the phenylpiperazinium cation, with occupancies of 0.687 (10)/0.313 (10), 0.51 (7)/0.49 (7) and 0.611 (13)/389 (13), respectively. This is a common feature of this moiety as shown in a recent study (Kiran Kumar et al., 2019a) of 12 salts of the 4-methoxyphenylpiperazinium cation, of which four were found to contain similar disorder of the phenyl ring.
For the structures containing benzoate or p-substituted benzoate anions, the C—O distances fall into two groups. In one group (3, 5), these distances are the same within experimental error at 2.246 (4) Å, while in the second group (1, 4, and 9) these are substantially different and average 2.235 (4) and 2.255 (4) Å.
For the structures containing the 3,5-dinitrosalicylic (6), 3,5-dinitrobenzoate (7) and 2,3,5-trinitrophenolate ions (8), some interesting patterns emerge. In the anion of compound 6, the carboxyl group is unionized, with C—O distances of 1.211 (4) and 1.309 (4) Å and it is the phenolic H atom that has been lost (Fig. 5). The C12—O3 distance, 1.283 (4) Å, is closer to that normally found in than to that typical of or (Allen et al., 1987). In addition, the C11—C12 and C12—C13 distances, 1.428 (4) and 1.449 (5) Å, respectively, are significantly larger than the other C—C distances in this ring, which lie in the rather narrow range 1.370 (4)–1.398 (4) Å, but the C—N and N—O distances of the nitro substituents are all typical of their types. These observations indicate that the negative charge in this anion is delocalized over the five atoms C11, C13, C14, C15 and C16, but without any significant delocalization onto the nitro groups, as has been observed in trinitrophenolate (picrate) anions (Kavitha et al., 2006; Sagar et al., 2017; Shaibah et al., 2017a,b). The carboxylate anion in 7 contains similar C—O distances [C17—O1 = 1.251 (14); C17—O2 = 1.256 (14) Å]. Structure 8 contains a picrate anion. Here the situation is similar to that of 6 in that the C—O distance is even shorter at 1.244 (3) Å and in the phenyl ring the C—C bonds are not equal with C11—C12 and C11—C16 being 1.443 (3) and 1.445 (3) Å, respectively, while the remaining C—C bonds range from 1.360 (3) to 1.386 (3) Å. For the nitro groups the C—N distances range from 1.441 (3) to 1.456 (3) Å, indicating that the negative charge in this anion is also delocalized over the five atoms C11, C13, C14, C15 and C16, but without any significant delocalization onto the nitro groups.
Structure 10 contains the tosylate anion. There are two formula units in the and in both anions the S—O distances are almost equal within experimental error ranging from 1.448 (12) to 1.462 (11) Å and 1.430 (13) to 1.473 (11) Å. Structures 11 and 12 contain the mono-anions of the di-carboxylic acids tartaric acid and fumaric acid. For both structures the metrical parameters of both cation and anion are in the normal range for such species. It notable that in 1 and 3–11, the phenyl substituent occupies an equatorial position in the piperazinium cation, but for 12 this substituent occupies an axial position.
3. Supramolecular features
In discussing the supramolecular features of these eleven molecular salts it is convenient to break these up into four groups based on the nature of the anion and the stoichiometry of the resulting salt. In the first group are structures 1, 3, 4, 5, and 9, which contain benzoate and substituted benzoate anions. In the second group are 6, 7, and 8 in which the anions contain nitrated phenyl rings. In the third group, 10 contains a tosylate anion, and in the fourth group, 11 and 12 contain the mono-deprotonated dicarboxylate anions hydrogen tartarate and hydrogen fumarate. The hydrogen bonds for 1 and 3–12 are listed in Tables 1–11.
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Even though 1, 3, 4, 5, and 9 contain similar anions, only 3 and 9 are isomorphous. For 1 (Fig. 12), which contains a water molecule of crystallization, there are R63(12) rings (Etter et al., 1990) made up of N—H⋯O and O—H⋯O hydrogen bonds, which involve the water molecule, and R42(10) rings made up of N—H⋯O hydrogen bonds, which do not involve the water molecule. This combination of R63(12) and R42(10) rings form ribbons propagating in the a-axis direction. In addition, there is a C—H⋯π interaction involving C2—H2 and the C11–C16 phenyl ring (Cg1) [C2⋯Cg1 = 3.610 (6) Å; C2—H2⋯Cg1 = 133°; −x, 1 − y, 1 − z]. In the packing arrangement for 3 shown in Fig. 13, both R44(12) rings exhibit N—H⋯O and O—H⋯O hydrogen bonds involving the cation, anion and water molecule as well as R42(10) rings showing O—H⋯O hydrogen bonds just associated with the cation and anion. These link the cations, anions and water molecules into ribbons propagating in the [101] direction. In addition there is a C—H⋯π interaction involving C2—H2 and the C11–C16 phenyl ring (Cg1) [C2⋯Cg1 = 3.6040 (14) Å; C2—H2⋯Cg1 = 133°; 1 − x, 1 − y, 1 − z].
In 4, there is no water molecule of crystallization. In this case there is an R88(24) ring with a topology analogous to the seam of a tennis ball (Fig. 14) involving N—H⋯O hydrogen bonds. These collections of cations and anions linked by R88(24) rings pack in the a-axis direction (Fig. 15). In addition there is a C—H⋯π interaction involving C19—H19 and the C21–C26 phenyl ring (Cg1) [C19⋯Cg1 = 3.750 (4) Å; C19—H19B⋯Cg1 = 154°; 1 − x, 1 − y, 1 − z]. In 5, R44(12) rings link the cations and anions via N—H⋯O hydrogen bonds and this collection forms ribbons in the b-axis direction (Fig. 16). In addition, the –NO2 group accepts an N—H⋯(O,O) bifurcated hydrogen bond. There is a further interaction with a phenyl ring (C11–C16, Cg1) involving the nitro substituent [N3⋯Cg1 = 3.530 (14) Å; N3—O3⋯Cg1 = 140.6 (13)°, x, − y, + z].
In 6, there are R44(16) loops linking the phenylpiperazinium cations and the 3,5-dintrosalicylate anions via N—H⋯O hydrogen bonds (Fig. 17). In addition, there are π–π interactions involving the phenyl ring (C11–C16, Cg1) of the 3,5-dintrosalicylate anions, which form offset stacks (slippages of 1.580 and 1.900 Å) in the [110] direction [Cg1⋯Cg1 = 3.3600 (15) Å; −x, 1 − y, 1 − z; Cg1⋯Cg1 = 3.3690 (15) Å; −x, 2 − y, 1 − z].
The packing of 7 is composed of R44(22) rings in the (101) plane made up of N—H⋯O hydrogen bonds involving the phenylpiperazinium cation and carboxylate group of the 3,5-dinitrobenzoate anion (Fig. 18). These planes are linked in the [111] direction by C22(6) chains also involving N—H⋯O hydrogen-bonding interactions involving the phenylpiperazinium cation and carboxylate group of the 3,5-dinitrobenzoate anion and weak C—H⋯O interactions (Fig. 19). In this structure there are no C—H⋯π or π–π interactions.
In 8 there are C22(8) chains made up of N—H⋯O hydrogen bonds involving the phenylpiperazinium cation and a nitro group of the picrate anion (Fig. 20). In addition, the picrate anions form strong π–π interactions (C1–C6, Cg1) in the a-axis direction [Cg1⋯Cg1 = 3.4395 (5) Å; 2 − x, 1 − y, −z; Cg1⋯Cg1 = 3.4223 (5) Å; 2 − x, −y, −z] (Fig. 21). Furthermore, there are C—H⋯π interactions involving the phenyl ring (C1–C6, Cg1) of the phenylpiperazinium cation [C3⋯Cg1 = 3.683 (3) Å, C3—H3⋯Cg1 = 134°, 2 − x, + y, − z; C8⋯Cg1 = 3.512 (3) Å, C8—H8A⋯Cg1 = 160°, 1 − x, − + y, − z] (one example shown in Fig. 22).
In the case of 9 there are two anti-parallel C22(6) chains linked by N—H⋯O hydrogen bonds as well as C—H⋯O interactions involving the water oxygen atom, which combine to form ribbons propagating in the a-axis direction (Fig. 23). In addition, there are C—H⋯π interactions (C11–C16, Cg1) involving the benzoate phenyl ring [C2⋯Cg1 = 3.710 (4) Å, C2—H2⋯Cg1 = 141°, −x, 1 − y, 1 − z; C6⋯Cg1 = 3.656 (4) Å, C6—H6⋯Cg1 = 142°, 1 − x, 1 − y, 2 − z]. The overall packing is shown in Fig. 24.
The structure of 10 contains the tosylate anion, which contains the non-planar –SO3− group. This results in a packing arrangement in which N—H⋯O hydrogen bonds involving the phenylpiperazinium cations and tosylate anions are arranged such that there are hydrophilic and hydrophobic (110) planes (Fig. 25). This structure also contains C—H⋯π interactions involving one of the phenylpiperazinium cations (C18–C23, Cg1) and tosylate anions [C30⋯Cg1 = 3.74 (3) Å, C30—H30⋯Cg1 = 144°, 1 − x, − + y, −z].
Structure 11 has a complicated packing arrangement as in addition to the phenylpiperazinium NH2 group, the flexible tartarate anion contains four OH groups and there is a water molecule of crystallization. Multiple N—H⋯O and O—H⋯O hydrogen-bonding interactions combine to form a three-dimensional array (Fig. 26).
Structure 12 contains a phenylpiperazinium cation and the monoanion of fumaric acid. In the packing of this structure, there are two C11(7) chains in the b-axis direction involving the fumarate anions and composed of O—H⋯O hydrogen bonds. These chains are in turn cross-linked by both N—H⋯O hydrogen bonds and C—H⋯O interactions (Fig. 27). There are also C—H⋯π interactions involving the phenyl ring (C1–C6, Cg1) of the phenylpiperazinium cation [C5⋯Cg1 = 3.723 (3) Å, C5—H5⋯Cg1 =144°, −x, 1 − y, + z; C10⋯Cg1 = 3.608 (3) Å, C10—H10A⋯Cg1 = 145°, −x, −y, − + z].
The Hirshfeld surface fingerprint plots for 1 and 3–12 generated using CrystalExplorer are available in the supporting information. All of them show the distinctive `pincer spikes' associated with the N—H⋯O and/or O—H⋯O hydrogen bonds (Spackman et al., 2021).
4. Database survey
The structural versatility of the 1-phenylpiperazine moiety itself is shown by its involvement in many structural forms, including as neutral co-crystals [Cambridge Structural Database (Groom et al., 2016) refcodes HINQUR and HINRAY, Müller-Buschbaum & Zurawski, 2007], as neutral ligands (HIWJAY, Stocker et al., 1999; HIWJAY01, VIYPIE, VIYPOK, VIYPUQ; Pike et al., 2014), as simultaneously both neutral ligands and co-crystals (FITTEI and FITTIM, Quitmann & Müller-Buschbaum, 2005; HOCBEH, HOCBIL, PIYXEB, Zurawski & Müller-Buschbaum, 2008). In addition, there have been many structural investigations of 1-phenylpiperazine as a cation, combined with simple anions (DMPIPZ, Chothia & Pauling, 1978; JEHXIE, Batsanov et al., 2006; KUZWUY, Marouani et al., 2010; LOHQIL, Oueslati et al., 2019; QORVEB, Marouani et al., 2012; SUYXEQ, Essid et al., 2010), with simple anionic metal salts (BEBKAX, Lahbib et al., 2017; CEBHIB, Garbia et al., 2005; PENWAJ, Mathlouthi et al., 2017; PHPIPZ, Battaglia et al., 1979; QIZPIA, Dhieb et al., 2014; SUKKAM, Dhieb et al., 2015; ZAMHUQ, Zouari et al., 1995), combined with anionic carboxylates (IGOGUI, Pang et al., 2015; VAKCIW, Zong et al., 2016; Mahesha et al., 2022), combined with anionic pyrimidines (DUPMUY, DUPNAF, Al-Alshaikh et al., 2015), combined with anionic ligands (WOVKAW, Lo et al., 2019), combined with a clathrate (GUBHOB, Wu et al., 2009), and combined with anionic metal complexes (DUJPIK, Shin et al., 2020; SICGUJ, Nasr et al., 2018; SICGUJ01, Khedhiri et al. 2018).
5. Synthesis and crystallization
For the synthesis of salts 1–12, a solution of commercially available 1-phenylpiperazine (100 mg, 0.62 mol) (from Sigma-Aldrich) in methanol (10 ml) was mixed with an equimolar solution of (1) 4-fluorobenzoic acid (87 mg, 0.62 mol), (2) 4-chlorobenzoic acid (97 mg, 0.62 mol), (3) 4-bromobenzoic acid (125 mg, 0.62 mol), (4) 4-iodobenzoic acid (154 mg, 0.62 mol), (5) 4-nitrobenzoic acid (104 mg, 0.62 mol), (6) 3,5-dinitrosalicylic acid (104 mg, 0.62 mol), (7) 3,5-dinitrobenzoic acid (132 mg, 0.62 mol), (8) picric acid (142 mg, 0.62 mol), (9) benzoic acid (76 mg, 0.62 mol), (10) p-toluenesulfonic acid (107 mg, 0.62 mol), (11) tartaric acid (93 mg, 0.62 mol) and (12) fumaric acid (72 mg, 0.62 mol). The resulting mixture was stirred for 30 min at 323 K and allowed to stand at room temperature. X-ray quality crystals of 1 and 3–12 were formed on slow evaporation after one week (m.p.: 381–384 K (1), 382–387 K (3), 413–418 K (4), 423–428 K (5), 431–436 K (6), 427–429 K (7), 430–433 K (8), 455–457 K (9), 377–380 K (10), 416–420 K (11) and 438–440 K (12). No crystals of (2) (m.p. 488–490 K) suitable for X-ray diffraction were obtained.
6. Refinement
Crystal data, data collection and structure 1 and 3–12 are summarized in Table 12. All hydrogen atoms were positioned geometrically with their Uiso values 1.2 times that of their attached atoms. For some structures (6, 10, and 11), the phenyl ring of the piperazinium cation was disordered over two orientations in ratios of 0.687 (10)/0.313 (10); 0.51 (7)/0.49 (7), and 0.611 (13)/0.389 (13) for 6, 10, and 11, respectively. For both 5 and 6, a nitro group was disordered and modeled with two orientations with occupancies of 0.62 (3)/0.38 (3) and 0.690 (11)/0.310 (11), respectively.
details for structures
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Supporting information
https://doi.org/10.1107/S2056989022009057/hb8034sup1.cif
contains datablocks 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12. DOI:Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989022009057/hb80341sup2.hkl
Structure factors: contains datablock 3. DOI: https://doi.org/10.1107/S2056989022009057/hb80343sup3.hkl
Structure factors: contains datablock 4. DOI: https://doi.org/10.1107/S2056989022009057/hb80344sup4.hkl
Structure factors: contains datablock 5. DOI: https://doi.org/10.1107/S2056989022009057/hb80345sup5.hkl
Structure factors: contains datablock 6. DOI: https://doi.org/10.1107/S2056989022009057/hb80346sup6.hkl
Structure factors: contains datablock 7. DOI: https://doi.org/10.1107/S2056989022009057/hb80347sup7.hkl
Structure factors: contains datablock 8. DOI: https://doi.org/10.1107/S2056989022009057/hb80348sup8.hkl
Structure factors: contains datablock 9. DOI: https://doi.org/10.1107/S2056989022009057/hb80349sup9.hkl
Structure factors: contains datablock 10. DOI: https://doi.org/10.1107/S2056989022009057/hb803410sup10.hkl
Structure factors: contains datablock 11. DOI: https://doi.org/10.1107/S2056989022009057/hb803411sup11.hkl
Structure factors: contains datablock 12. DOI: https://doi.org/10.1107/S2056989022009057/hb803412sup12.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989022009057/hb80343sup12.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989022009057/hb80344sup13.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989022009057/hb80345sup14.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989022009057/hb80346sup15.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989022009057/hb80347sup16.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989022009057/hb80348sup17.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989022009057/hb80349sup18.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989022009057/hb803410sup19.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989022009057/hb803411sup20.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989022009057/hb803412sup21.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989022009057/hb80341sup22.cml
Hirschfeld fingerprint plots for the eleven structures. DOI: https://doi.org/10.1107/S2056989022009057/hb8034sup22.docx
For all structures, data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell
CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (1), (3), (4), (5), (6), (7), (8), (9), (10), (11); SHELXT2014 (Sheldrick, 2015a) for (12). Program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b) for (1), (3), (4), (5), (6), (7), (8), (9), (10); SHELXL2014/6 (Sheldrick, 2015b) for (11), (12). For all structures, molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C10H15N2+·C7H4FO2−·H2O | Z = 2 |
Mr = 320.36 | F(000) = 340 |
Triclinic, P1 | Dx = 1.286 Mg m−3 |
a = 6.239 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.496 (1) Å | Cell parameters from 1437 reflections |
c = 17.817 (3) Å | θ = 2.8–27.7° |
α = 93.55 (2)° | µ = 0.10 mm−1 |
β = 92.94 (2)° | T = 293 K |
γ = 94.87 (2)° | Rod, colourless |
V = 827.3 (2) Å3 | 0.44 × 0.32 × 0.16 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 1611 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.033 |
ω and φ scans | θmax = 25.3°, θmin = 2.9° |
Absorption correction: multi-scan (CrysalisRED; Oxford Diffraction, 2007) | h = −7→7 |
Tmin = 0.613, Tmax = 1.000 | k = −9→8 |
4669 measured reflections | l = −21→20 |
3013 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.090 | Hydrogen site location: mixed |
wR(F2) = 0.226 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0717P)2 + 0.6694P] where P = (Fo2 + 2Fc2)/3 |
3013 reflections | (Δ/σ)max < 0.001 |
220 parameters | Δρmax = 0.27 e Å−3 |
4 restraints | Δρmin = −0.20 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 | ||
N1 | 0.1673 (5) | 0.6916 (4) | 0.28754 (18) | 0.0488 (8) | |
N2 | 0.2637 (6) | 0.7578 (5) | 0.4474 (2) | 0.0582 (10) | |
H21 | 0.321 (6) | 0.736 (6) | 0.4932 (14) | 0.070* | |
H22 | 0.222 (6) | 0.867 (3) | 0.453 (2) | 0.070* | |
C1 | 0.1054 (6) | 0.7113 (5) | 0.2116 (2) | 0.0517 (10) | |
C2 | −0.0937 (8) | 0.6442 (7) | 0.1796 (3) | 0.0795 (15) | |
H2 | −0.193159 | 0.589826 | 0.210092 | 0.095* | |
C3 | −0.1510 (9) | 0.6546 (8) | 0.1045 (3) | 0.1007 (19) | |
H3 | −0.285388 | 0.604546 | 0.084997 | 0.121* | |
C4 | −0.0122 (11) | 0.7376 (9) | 0.0585 (3) | 0.1030 (19) | |
H4 | −0.049909 | 0.745192 | 0.007649 | 0.124* | |
C5 | 0.1822 (10) | 0.8090 (10) | 0.0887 (3) | 0.122 (3) | |
H5 | 0.278723 | 0.865814 | 0.057892 | 0.147* | |
C6 | 0.2409 (9) | 0.7997 (8) | 0.1637 (3) | 0.0979 (19) | |
H6 | 0.373978 | 0.853592 | 0.182809 | 0.117* | |
C7 | 0.3620 (6) | 0.8019 (6) | 0.3177 (2) | 0.0608 (11) | |
H7A | 0.332558 | 0.927034 | 0.320838 | 0.073* | |
H7B | 0.476070 | 0.788623 | 0.283301 | 0.073* | |
C8 | 0.4378 (7) | 0.7509 (6) | 0.3946 (2) | 0.0616 (12) | |
H8A | 0.484338 | 0.630572 | 0.390672 | 0.074* | |
H8B | 0.560050 | 0.832523 | 0.413731 | 0.074* | |
C9 | 0.0695 (7) | 0.6398 (6) | 0.4170 (2) | 0.0599 (11) | |
H9A | −0.045974 | 0.649597 | 0.451027 | 0.072* | |
H9B | 0.103679 | 0.515781 | 0.413417 | 0.072* | |
C10 | −0.0033 (6) | 0.6933 (6) | 0.3403 (2) | 0.0558 (11) | |
H10A | −0.124568 | 0.611513 | 0.320378 | 0.067* | |
H10B | −0.051786 | 0.812879 | 0.345074 | 0.067* | |
F1 | 0.5316 (7) | 0.7684 (6) | 0.94599 (18) | 0.1434 (15) | |
O1 | 0.1448 (6) | 0.8383 (6) | 0.6190 (2) | 0.1136 (14) | |
O2 | 0.4185 (6) | 0.6849 (4) | 0.59104 (18) | 0.0761 (10) | |
C11 | 0.3677 (6) | 0.7628 (5) | 0.7197 (2) | 0.0519 (10) | |
C12 | 0.5515 (7) | 0.6900 (6) | 0.7457 (2) | 0.0605 (11) | |
H12 | 0.639144 | 0.638731 | 0.711219 | 0.073* | |
C13 | 0.6074 (8) | 0.6918 (7) | 0.8214 (3) | 0.0777 (14) | |
H13 | 0.731513 | 0.642435 | 0.838182 | 0.093* | |
C14 | 0.4782 (10) | 0.7668 (8) | 0.8711 (3) | 0.0885 (16) | |
C15 | 0.2959 (10) | 0.8423 (8) | 0.8486 (3) | 0.0890 (16) | |
H15 | 0.210580 | 0.894321 | 0.883627 | 0.107* | |
C16 | 0.2416 (7) | 0.8393 (6) | 0.7725 (3) | 0.0723 (13) | |
H16 | 0.117563 | 0.889726 | 0.756336 | 0.087* | |
C17 | 0.3049 (7) | 0.7617 (6) | 0.6375 (3) | 0.0609 (12) | |
O3 | 0.7825 (5) | 0.8718 (5) | 0.5423 (2) | 0.0747 (10) | |
H31 | 0.898 (5) | 0.857 (8) | 0.565 (3) | 0.112* | |
H32 | 0.674 (6) | 0.829 (8) | 0.562 (3) | 0.112* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0464 (19) | 0.0462 (19) | 0.053 (2) | −0.0029 (14) | 0.0061 (15) | 0.0075 (14) |
N2 | 0.072 (2) | 0.048 (2) | 0.055 (2) | 0.0064 (18) | −0.0066 (19) | 0.0061 (17) |
C1 | 0.058 (3) | 0.048 (2) | 0.048 (3) | 0.0003 (19) | 0.005 (2) | 0.0056 (18) |
C2 | 0.079 (3) | 0.094 (4) | 0.060 (3) | −0.022 (3) | −0.005 (3) | 0.017 (3) |
C3 | 0.104 (4) | 0.118 (5) | 0.070 (4) | −0.036 (4) | −0.021 (3) | 0.017 (3) |
C4 | 0.129 (5) | 0.120 (5) | 0.056 (3) | −0.015 (4) | −0.006 (3) | 0.014 (3) |
C5 | 0.116 (5) | 0.185 (7) | 0.059 (4) | −0.045 (5) | 0.008 (3) | 0.029 (4) |
C6 | 0.088 (4) | 0.141 (5) | 0.058 (3) | −0.039 (4) | 0.003 (3) | 0.020 (3) |
C7 | 0.049 (2) | 0.072 (3) | 0.059 (3) | −0.009 (2) | 0.004 (2) | 0.009 (2) |
C8 | 0.053 (3) | 0.065 (3) | 0.065 (3) | 0.000 (2) | −0.002 (2) | 0.003 (2) |
C9 | 0.064 (3) | 0.056 (3) | 0.058 (3) | −0.008 (2) | 0.005 (2) | 0.007 (2) |
C10 | 0.049 (2) | 0.058 (3) | 0.060 (3) | −0.0019 (19) | 0.006 (2) | 0.006 (2) |
F1 | 0.180 (4) | 0.187 (4) | 0.060 (2) | 0.003 (3) | −0.002 (2) | 0.004 (2) |
O1 | 0.090 (3) | 0.140 (4) | 0.114 (3) | 0.037 (3) | −0.027 (2) | 0.029 (3) |
O2 | 0.097 (2) | 0.069 (2) | 0.061 (2) | 0.0018 (18) | −0.0046 (18) | 0.0101 (16) |
C11 | 0.049 (2) | 0.041 (2) | 0.066 (3) | −0.0054 (18) | 0.007 (2) | 0.0126 (19) |
C12 | 0.062 (3) | 0.056 (3) | 0.062 (3) | 0.004 (2) | −0.001 (2) | 0.006 (2) |
C13 | 0.082 (3) | 0.083 (4) | 0.067 (3) | 0.009 (3) | −0.009 (3) | 0.010 (3) |
C14 | 0.105 (4) | 0.098 (4) | 0.059 (3) | −0.005 (3) | −0.002 (3) | 0.004 (3) |
C15 | 0.097 (4) | 0.093 (4) | 0.079 (4) | 0.004 (3) | 0.031 (3) | 0.001 (3) |
C16 | 0.057 (3) | 0.066 (3) | 0.096 (4) | 0.002 (2) | 0.012 (3) | 0.018 (3) |
C17 | 0.056 (3) | 0.049 (3) | 0.076 (3) | −0.012 (2) | −0.009 (2) | 0.020 (2) |
O3 | 0.071 (2) | 0.065 (2) | 0.088 (3) | 0.0124 (18) | −0.0088 (18) | 0.0039 (17) |
N1—C1 | 1.408 (5) | C8—H8B | 0.9700 |
N1—C10 | 1.456 (5) | C9—C10 | 1.507 (5) |
N1—C7 | 1.468 (5) | C9—H9A | 0.9700 |
N2—C8 | 1.475 (5) | C9—H9B | 0.9700 |
N2—C9 | 1.495 (5) | C10—H10A | 0.9700 |
N2—H21 | 0.904 (19) | C10—H10B | 0.9700 |
N2—H22 | 0.881 (19) | F1—C14 | 1.358 (6) |
C1—C2 | 1.381 (6) | O1—C17 | 1.235 (5) |
C1—C6 | 1.389 (6) | O2—C17 | 1.261 (5) |
C2—C3 | 1.377 (6) | C11—C12 | 1.382 (5) |
C2—H2 | 0.9300 | C11—C16 | 1.386 (6) |
C3—C4 | 1.361 (8) | C11—C17 | 1.496 (6) |
C3—H3 | 0.9300 | C12—C13 | 1.375 (6) |
C4—C5 | 1.355 (8) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—C14 | 1.356 (7) |
C5—C6 | 1.375 (7) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—C15 | 1.366 (7) |
C6—H6 | 0.9300 | C15—C16 | 1.377 (7) |
C7—C8 | 1.509 (5) | C15—H15 | 0.9300 |
C7—H7A | 0.9700 | C16—H16 | 0.9300 |
C7—H7B | 0.9700 | O3—H31 | 0.83 (2) |
C8—H8A | 0.9700 | O3—H32 | 0.83 (2) |
C1—N1—C10 | 116.2 (3) | C7—C8—H8B | 109.5 |
C1—N1—C7 | 115.9 (3) | H8A—C8—H8B | 108.1 |
C10—N1—C7 | 111.5 (3) | N2—C9—C10 | 110.4 (3) |
C8—N2—C9 | 110.3 (3) | N2—C9—H9A | 109.6 |
C8—N2—H21 | 107 (3) | C10—C9—H9A | 109.6 |
C9—N2—H21 | 117 (3) | N2—C9—H9B | 109.6 |
C8—N2—H22 | 111 (3) | C10—C9—H9B | 109.6 |
C9—N2—H22 | 106 (3) | H9A—C9—H9B | 108.1 |
H21—N2—H22 | 105 (4) | N1—C10—C9 | 112.3 (3) |
C2—C1—C6 | 115.5 (4) | N1—C10—H10A | 109.1 |
C2—C1—N1 | 122.4 (4) | C9—C10—H10A | 109.1 |
C6—C1—N1 | 122.2 (4) | N1—C10—H10B | 109.1 |
C3—C2—C1 | 122.7 (5) | C9—C10—H10B | 109.1 |
C3—C2—H2 | 118.7 | H10A—C10—H10B | 107.9 |
C1—C2—H2 | 118.7 | C12—C11—C16 | 117.8 (4) |
C4—C3—C2 | 120.5 (5) | C12—C11—C17 | 121.9 (4) |
C4—C3—H3 | 119.8 | C16—C11—C17 | 120.2 (4) |
C2—C3—H3 | 119.8 | C13—C12—C11 | 121.4 (4) |
C5—C4—C3 | 118.2 (5) | C13—C12—H12 | 119.3 |
C5—C4—H4 | 120.9 | C11—C12—H12 | 119.3 |
C3—C4—H4 | 120.9 | C14—C13—C12 | 118.8 (5) |
C4—C5—C6 | 121.8 (5) | C14—C13—H13 | 120.6 |
C4—C5—H5 | 119.1 | C12—C13—H13 | 120.6 |
C6—C5—H5 | 119.1 | C13—C14—F1 | 119.2 (6) |
C5—C6—C1 | 121.3 (5) | C13—C14—C15 | 122.3 (5) |
C5—C6—H6 | 119.4 | F1—C14—C15 | 118.5 (6) |
C1—C6—H6 | 119.4 | C14—C15—C16 | 118.3 (5) |
N1—C7—C8 | 112.4 (3) | C14—C15—H15 | 120.9 |
N1—C7—H7A | 109.1 | C16—C15—H15 | 120.9 |
C8—C7—H7A | 109.1 | C15—C16—C11 | 121.4 (5) |
N1—C7—H7B | 109.1 | C15—C16—H16 | 119.3 |
C8—C7—H7B | 109.1 | C11—C16—H16 | 119.3 |
H7A—C7—H7B | 107.9 | O1—C17—O2 | 123.6 (5) |
N2—C8—C7 | 110.8 (3) | O1—C17—C11 | 117.7 (5) |
N2—C8—H8A | 109.5 | O2—C17—C11 | 118.7 (4) |
C7—C8—H8A | 109.5 | H31—O3—H32 | 115 (6) |
N2—C8—H8B | 109.5 | ||
C10—N1—C1—C2 | −33.4 (6) | C1—N1—C10—C9 | 170.1 (3) |
C7—N1—C1—C2 | −167.2 (4) | C7—N1—C10—C9 | −54.1 (4) |
C10—N1—C1—C6 | 146.6 (5) | N2—C9—C10—N1 | 55.9 (4) |
C7—N1—C1—C6 | 12.8 (6) | C16—C11—C12—C13 | 0.5 (6) |
C6—C1—C2—C3 | 3.5 (8) | C17—C11—C12—C13 | −180.0 (4) |
N1—C1—C2—C3 | −176.4 (5) | C11—C12—C13—C14 | 0.0 (7) |
C1—C2—C3—C4 | −1.9 (9) | C12—C13—C14—F1 | 179.7 (4) |
C2—C3—C4—C5 | 0.0 (10) | C12—C13—C14—C15 | −0.7 (8) |
C3—C4—C5—C6 | −0.2 (11) | C13—C14—C15—C16 | 0.8 (9) |
C4—C5—C6—C1 | 2.1 (11) | F1—C14—C15—C16 | −179.6 (4) |
C2—C1—C6—C5 | −3.6 (8) | C14—C15—C16—C11 | −0.3 (8) |
N1—C1—C6—C5 | 176.4 (6) | C12—C11—C16—C15 | −0.4 (6) |
C1—N1—C7—C8 | −170.5 (3) | C17—C11—C16—C15 | −179.9 (4) |
C10—N1—C7—C8 | 53.5 (5) | C12—C11—C17—O1 | −176.1 (4) |
C9—N2—C8—C7 | 56.3 (4) | C16—C11—C17—O1 | 3.4 (6) |
N1—C7—C8—N2 | −55.1 (5) | C12—C11—C17—O2 | 3.2 (6) |
C8—N2—C9—C10 | −56.6 (4) | C16—C11—C17—O2 | −177.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1 | 0.90 (2) | 2.65 (4) | 3.215 (6) | 122 (3) |
N2—H21···O2 | 0.90 (2) | 1.89 (2) | 2.791 (5) | 175 (4) |
N2—H22···O3i | 0.88 (2) | 1.96 (2) | 2.812 (5) | 163 (4) |
C8—H8A···O2ii | 0.97 | 2.53 | 3.481 (6) | 168 |
C8—H8B···O3 | 0.97 | 2.60 | 3.341 (5) | 133 |
C9—H9A···O3iii | 0.97 | 2.59 | 3.416 (6) | 143 |
O3—H31···O1iv | 0.83 (2) | 1.79 (2) | 2.619 (5) | 176 (6) |
O3—H32···O2 | 0.83 (2) | 1.96 (2) | 2.773 (5) | 167 (6) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z; (iv) x+1, y, z. |
C10H15N2+·C7H4BrO2−·H2O | F(000) = 784 |
Mr = 381.27 | Dx = 1.449 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.183 (2) Å | Cell parameters from 1437 reflections |
b = 37.748 (7) Å | θ = 2.8–27.7° |
c = 7.506 (2) Å | µ = 2.37 mm−1 |
β = 93.69 (4)° | T = 293 K |
V = 1748.2 (8) Å3 | Rod, colourless |
Z = 4 | 0.46 × 0.20 × 0.12 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 1374 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.061 |
ω and φ scans | θmax = 25.4°, θmin = 2.8° |
Absorption correction: multi-scan (CrysalisRED; Oxford Diffraction, 2007) | h = −4→7 |
Tmin = 0.613, Tmax = 1.000 | k = −45→24 |
6103 measured reflections | l = −8→9 |
3170 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.138 | Hydrogen site location: mixed |
wR(F2) = 0.375 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.1282P)2 + 10.0601P] where P = (Fo2 + 2Fc2)/3 |
3170 reflections | (Δ/σ)max = 0.003 |
215 parameters | Δρmax = 0.49 e Å−3 |
7 restraints | Δρmin = −0.61 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 | Occ. (<1) | |
N1 | 0.7034 (12) | 0.4002 (2) | 0.2295 (10) | 0.047 (2) | |
N2 | 0.7744 (14) | 0.4754 (2) | 0.2661 (11) | 0.057 (2) | |
H2N1 | 0.816948 | 0.495983 | 0.221941 | 0.068* | 0.68 (16) |
H2N2 | 0.734325 | 0.479226 | 0.376244 | 0.068* | |
C1 | 0.6526 (17) | 0.3649 (3) | 0.2644 (14) | 0.052 (3) | |
C2 | 0.4510 (19) | 0.3499 (3) | 0.2008 (17) | 0.077 (4) | |
H2 | 0.347995 | 0.364177 | 0.140653 | 0.092* | |
C3 | 0.406 (2) | 0.3151 (4) | 0.226 (2) | 0.095 (4) | |
H3 | 0.275365 | 0.305737 | 0.179024 | 0.114* | |
C4 | 0.552 (3) | 0.2938 (4) | 0.320 (2) | 0.101 (5) | |
H4 | 0.518855 | 0.270118 | 0.340272 | 0.122* | |
C5 | 0.745 (3) | 0.3071 (4) | 0.385 (2) | 0.109 (5) | |
H5 | 0.846262 | 0.292510 | 0.444957 | 0.131* | |
C6 | 0.790 (2) | 0.3418 (3) | 0.361 (2) | 0.091 (4) | |
H6 | 0.919874 | 0.350644 | 0.411615 | 0.109* | |
C7 | 0.8936 (15) | 0.4148 (3) | 0.3321 (15) | 0.056 (3) | |
H7A | 0.863266 | 0.416060 | 0.457161 | 0.067* | |
H7B | 1.015626 | 0.398972 | 0.321899 | 0.067* | |
C8 | 0.9530 (18) | 0.4502 (3) | 0.2711 (16) | 0.066 (3) | |
H8A | 1.070611 | 0.459306 | 0.349995 | 0.080* | |
H8B | 1.005544 | 0.448322 | 0.152505 | 0.080* | |
C9 | 0.5886 (17) | 0.4613 (3) | 0.1532 (15) | 0.063 (3) | |
H9A | 0.628083 | 0.459435 | 0.030616 | 0.075* | |
H9B | 0.466823 | 0.477483 | 0.156218 | 0.075* | |
C10 | 0.5255 (17) | 0.4260 (3) | 0.2189 (14) | 0.057 (3) | |
H10A | 0.471137 | 0.428689 | 0.336512 | 0.069* | |
H10B | 0.408395 | 0.416774 | 0.140070 | 0.069* | |
Br1 | 0.9708 (5) | 0.72340 (4) | 0.1736 (4) | 0.1674 (14) | |
O1 | 0.6289 (16) | 0.5558 (3) | 0.3222 (15) | 0.114 (4) | |
O2 | 0.9081 (15) | 0.5426 (2) | 0.1687 (11) | 0.077 (2) | |
H2O | 0.853628 | 0.522821 | 0.170738 | 0.093* | 0.32 (16) |
C11 | 0.8325 (17) | 0.6031 (3) | 0.2219 (13) | 0.053 (3) | |
C12 | 1.0163 (19) | 0.6155 (3) | 0.1465 (14) | 0.063 (3) | |
H12 | 1.115409 | 0.599557 | 0.104078 | 0.076* | |
C13 | 1.053 (2) | 0.6508 (3) | 0.1343 (16) | 0.072 (3) | |
H13 | 1.177707 | 0.658367 | 0.083258 | 0.086* | |
C14 | 0.919 (3) | 0.6747 (4) | 0.1911 (19) | 0.088 (4) | |
C15 | 0.741 (3) | 0.6638 (4) | 0.277 (2) | 0.097 (5) | |
H15 | 0.650657 | 0.680550 | 0.324796 | 0.116* | |
C16 | 0.694 (2) | 0.6281 (4) | 0.2929 (17) | 0.080 (4) | |
H16 | 0.572770 | 0.620785 | 0.349992 | 0.096* | |
C17 | 0.787 (2) | 0.5643 (4) | 0.2376 (14) | 0.062 (3) | |
O3 | 0.7207 (13) | 0.4796 (2) | 0.6335 (11) | 0.073 (2) | |
H31 | 0.830 (14) | 0.4755 (18) | 0.696 (17) | 0.109* | |
H32 | 0.697 (5) | 0.5004 (5) | 0.635 (5) | 0.109* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.044 (5) | 0.050 (5) | 0.046 (5) | 0.003 (4) | 0.002 (4) | −0.005 (4) |
N2 | 0.063 (6) | 0.056 (5) | 0.052 (5) | −0.003 (5) | 0.011 (4) | 0.000 (4) |
C1 | 0.054 (6) | 0.053 (6) | 0.048 (6) | 0.007 (5) | −0.001 (5) | −0.010 (5) |
C2 | 0.066 (8) | 0.085 (9) | 0.076 (8) | −0.005 (7) | −0.021 (7) | 0.021 (7) |
C3 | 0.092 (10) | 0.077 (9) | 0.113 (12) | −0.021 (8) | −0.018 (9) | 0.004 (9) |
C4 | 0.119 (13) | 0.067 (9) | 0.116 (12) | −0.010 (9) | −0.015 (10) | 0.016 (9) |
C5 | 0.127 (13) | 0.062 (9) | 0.134 (14) | 0.012 (9) | −0.021 (11) | 0.010 (9) |
C6 | 0.085 (9) | 0.068 (8) | 0.117 (12) | −0.004 (7) | −0.015 (8) | 0.000 (8) |
C7 | 0.039 (6) | 0.060 (7) | 0.068 (7) | 0.003 (5) | 0.000 (5) | −0.003 (6) |
C8 | 0.056 (7) | 0.084 (9) | 0.061 (7) | −0.004 (6) | 0.010 (6) | 0.004 (6) |
C9 | 0.054 (7) | 0.068 (7) | 0.066 (7) | 0.003 (6) | 0.005 (6) | 0.006 (6) |
C10 | 0.065 (7) | 0.060 (7) | 0.045 (6) | 0.004 (6) | −0.012 (5) | −0.003 (5) |
Br1 | 0.266 (3) | 0.0626 (11) | 0.169 (2) | −0.0154 (13) | −0.020 (2) | −0.0006 (12) |
O1 | 0.091 (7) | 0.131 (9) | 0.123 (8) | −0.028 (6) | 0.036 (7) | 0.037 (7) |
O2 | 0.098 (6) | 0.063 (5) | 0.072 (6) | −0.005 (5) | 0.015 (5) | 0.005 (4) |
C11 | 0.052 (6) | 0.074 (7) | 0.033 (5) | 0.004 (6) | 0.006 (5) | −0.005 (5) |
C12 | 0.069 (7) | 0.074 (8) | 0.047 (6) | 0.004 (6) | 0.008 (6) | −0.003 (6) |
C13 | 0.085 (9) | 0.069 (8) | 0.060 (8) | −0.015 (7) | −0.003 (6) | 0.000 (7) |
C14 | 0.128 (13) | 0.067 (8) | 0.071 (9) | 0.011 (9) | 0.012 (9) | 0.006 (7) |
C15 | 0.110 (12) | 0.090 (11) | 0.089 (10) | 0.036 (9) | 0.006 (10) | −0.016 (9) |
C16 | 0.079 (9) | 0.102 (11) | 0.060 (7) | 0.006 (8) | 0.010 (6) | 0.009 (8) |
C17 | 0.058 (7) | 0.089 (9) | 0.037 (6) | −0.009 (7) | −0.013 (5) | 0.008 (6) |
O3 | 0.081 (6) | 0.073 (5) | 0.064 (5) | −0.015 (4) | 0.010 (4) | −0.006 (4) |
N1—C1 | 1.398 (12) | C9—C10 | 1.483 (14) |
N1—C10 | 1.467 (12) | C9—H9A | 0.9700 |
N1—C7 | 1.471 (12) | C9—H9B | 0.9700 |
N2—C8 | 1.456 (13) | C10—H10A | 0.9700 |
N2—C9 | 1.481 (13) | C10—H10B | 0.9700 |
N2—H2N1 | 0.8900 | Br1—C14 | 1.872 (14) |
N2—H2N2 | 0.8900 | O1—C17 | 1.242 (13) |
C1—C6 | 1.387 (16) | O2—C17 | 1.244 (14) |
C1—C2 | 1.424 (15) | O2—H2O | 0.8200 |
C2—C3 | 1.356 (17) | C11—C12 | 1.384 (14) |
C2—H2 | 0.9300 | C11—C16 | 1.402 (16) |
C3—C4 | 1.38 (2) | C11—C17 | 1.495 (16) |
C3—H3 | 0.9300 | C12—C13 | 1.354 (16) |
C4—C5 | 1.35 (2) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—C14 | 1.312 (18) |
C5—C6 | 1.352 (17) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—C15 | 1.38 (2) |
C6—H6 | 0.9300 | C15—C16 | 1.385 (19) |
C7—C8 | 1.467 (14) | C15—H15 | 0.9300 |
C7—H7A | 0.9700 | C16—H16 | 0.9300 |
C7—H7B | 0.9700 | O3—H31 | 0.81 (2) |
C8—H8A | 0.9700 | O3—H32 | 0.796 (19) |
C8—H8B | 0.9700 | ||
C1—N1—C10 | 117.8 (8) | C7—C8—H8B | 108.9 |
C1—N1—C7 | 116.2 (8) | H8A—C8—H8B | 107.7 |
C10—N1—C7 | 110.5 (7) | N2—C9—C10 | 110.1 (9) |
C8—N2—C9 | 109.8 (8) | N2—C9—H9A | 109.6 |
C8—N2—H2N1 | 109.7 | C10—C9—H9A | 109.6 |
C9—N2—H2N1 | 109.7 | N2—C9—H9B | 109.6 |
C8—N2—H2N2 | 109.7 | C10—C9—H9B | 109.6 |
C9—N2—H2N2 | 109.7 | H9A—C9—H9B | 108.2 |
H2N1—N2—H2N2 | 108.2 | N1—C10—C9 | 113.8 (9) |
C6—C1—N1 | 124.0 (10) | N1—C10—H10A | 108.8 |
C6—C1—C2 | 114.6 (10) | C9—C10—H10A | 108.8 |
N1—C1—C2 | 121.3 (9) | N1—C10—H10B | 108.8 |
C3—C2—C1 | 121.5 (11) | C9—C10—H10B | 108.8 |
C3—C2—H2 | 119.3 | H10A—C10—H10B | 107.7 |
C1—C2—H2 | 119.3 | C17—O2—H2O | 109.5 |
C2—C3—C4 | 120.3 (13) | C12—C11—C16 | 117.6 (11) |
C2—C3—H3 | 119.8 | C12—C11—C17 | 121.9 (10) |
C4—C3—H3 | 119.8 | C16—C11—C17 | 120.4 (11) |
C5—C4—C3 | 120.0 (14) | C13—C12—C11 | 120.4 (11) |
C5—C4—H4 | 120.0 | C13—C12—H12 | 119.8 |
C3—C4—H4 | 120.0 | C11—C12—H12 | 119.8 |
C6—C5—C4 | 119.8 (15) | C14—C13—C12 | 123.0 (13) |
C6—C5—H5 | 120.1 | C14—C13—H13 | 118.5 |
C4—C5—H5 | 120.1 | C12—C13—H13 | 118.5 |
C5—C6—C1 | 123.7 (13) | C13—C14—C15 | 119.1 (13) |
C5—C6—H6 | 118.2 | C13—C14—Br1 | 122.7 (13) |
C1—C6—H6 | 118.2 | C15—C14—Br1 | 118.1 (12) |
C8—C7—N1 | 112.7 (9) | C14—C15—C16 | 120.5 (13) |
C8—C7—H7A | 109.0 | C14—C15—H15 | 119.7 |
N1—C7—H7A | 109.0 | C16—C15—H15 | 119.7 |
C8—C7—H7B | 109.0 | C15—C16—C11 | 119.2 (12) |
N1—C7—H7B | 109.0 | C15—C16—H16 | 120.4 |
H7A—C7—H7B | 107.8 | C11—C16—H16 | 120.4 |
N2—C8—C7 | 113.5 (9) | O1—C17—O2 | 123.8 (12) |
N2—C8—H8A | 108.9 | O1—C17—C11 | 116.9 (12) |
C7—C8—H8A | 108.9 | O2—C17—C11 | 119.3 (10) |
N2—C8—H8B | 108.9 | H31—O3—H32 | 109 (4) |
C10—N1—C1—C6 | −147.2 (11) | C1—N1—C10—C9 | −170.7 (9) |
C7—N1—C1—C6 | −12.7 (15) | C7—N1—C10—C9 | 52.4 (11) |
C10—N1—C1—C2 | 33.1 (14) | N2—C9—C10—N1 | −55.9 (12) |
C7—N1—C1—C2 | 167.6 (10) | C16—C11—C12—C13 | −3.5 (15) |
C6—C1—C2—C3 | −3.4 (18) | C17—C11—C12—C13 | −180.0 (10) |
N1—C1—C2—C3 | 176.3 (12) | C11—C12—C13—C14 | −0.2 (19) |
C1—C2—C3—C4 | 3 (2) | C12—C13—C14—C15 | 4 (2) |
C2—C3—C4—C5 | −2 (3) | C12—C13—C14—Br1 | −180.0 (9) |
C3—C4—C5—C6 | 2 (3) | C13—C14—C15—C16 | −4 (2) |
C4—C5—C6—C1 | −3 (3) | Br1—C14—C15—C16 | 179.6 (11) |
N1—C1—C6—C5 | −175.8 (14) | C14—C15—C16—C11 | 1 (2) |
C2—C1—C6—C5 | 4 (2) | C12—C11—C16—C15 | 3.2 (17) |
C1—N1—C7—C8 | 172.4 (9) | C17—C11—C16—C15 | 179.7 (11) |
C10—N1—C7—C8 | −50.0 (11) | C12—C11—C17—O1 | 173.4 (10) |
C9—N2—C8—C7 | −55.9 (12) | C16—C11—C17—O1 | −3.0 (15) |
N1—C7—C8—N2 | 53.6 (12) | C12—C11—C17—O2 | −5.8 (15) |
C8—N2—C9—C10 | 55.7 (11) | C16—C11—C17—O2 | 177.8 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N1···O2 | 0.89 | 1.90 | 2.780 (11) | 170 |
N2—H2N2···O3 | 0.89 | 1.94 | 2.803 (12) | 164 |
C8—H8A···O3i | 0.97 | 2.64 | 3.377 (14) | 133 |
C8—H8B···O2ii | 0.97 | 2.53 | 3.475 (14) | 166 |
C9—H9B···O3iii | 0.97 | 2.59 | 3.403 (14) | 142 |
O2—H2O···N2 | 0.82 | 2.00 | 2.780 (11) | 159 |
O3—H31···O2i | 0.81 (2) | 1.98 (2) | 2.782 (12) | 170 (7) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y+1, −z; (iii) −x+1, −y+1, −z+1. |
C10H15N2+·C7H4IO2− | F(000) = 1632 |
Mr = 410.24 | Dx = 1.652 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.8507 (4) Å | Cell parameters from 6801 reflections |
b = 23.4045 (7) Å | θ = 2.6–27.8° |
c = 13.3019 (4) Å | µ = 1.95 mm−1 |
β = 102.491 (4)° | T = 293 K |
V = 3298.13 (19) Å3 | Prism, colourless |
Z = 8 | 0.48 × 0.48 × 0.40 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 4641 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.024 |
Rotation method data acquisition using ω scans. | θmax = 27.8°, θmin = 2.8° |
Absorption correction: multi-scan (CrysalisRED; Oxford Diffraction, 2007) | h = −7→13 |
Tmin = 0.575, Tmax = 1.000 | k = −30→15 |
14154 measured reflections | l = −17→17 |
7079 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: mixed |
wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0402P)2] where P = (Fo2 + 2Fc2)/3 |
7079 reflections | (Δ/σ)max = 0.002 |
409 parameters | Δρmax = 0.77 e Å−3 |
4 restraints | Δρmin = −1.25 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 | ||
C1 | 0.6237 (3) | 0.57603 (14) | 0.0843 (2) | 0.0363 (8) | |
C2 | 0.4969 (3) | 0.58795 (15) | 0.0505 (3) | 0.0431 (9) | |
H2 | 0.437868 | 0.568638 | 0.079160 | 0.052* | |
C3 | 0.4565 (4) | 0.62827 (17) | −0.0255 (3) | 0.0535 (10) | |
H3 | 0.370693 | 0.635548 | −0.047848 | 0.064* | |
C4 | 0.5422 (4) | 0.65774 (17) | −0.0684 (3) | 0.0587 (11) | |
H4 | 0.514944 | 0.685086 | −0.119018 | 0.070* | |
C5 | 0.6689 (4) | 0.64613 (17) | −0.0351 (3) | 0.0578 (11) | |
H5 | 0.727710 | 0.665869 | −0.063350 | 0.069* | |
C6 | 0.7087 (3) | 0.60578 (16) | 0.0390 (3) | 0.0488 (9) | |
H6 | 0.794547 | 0.598015 | 0.059728 | 0.059* | |
C7 | 0.5780 (3) | 0.49980 (14) | 0.1955 (2) | 0.0399 (8) | |
H7A | 0.522273 | 0.482727 | 0.136209 | 0.048* | |
H7B | 0.527435 | 0.523672 | 0.230538 | 0.048* | |
C8 | 0.6407 (3) | 0.45316 (15) | 0.2676 (3) | 0.0461 (9) | |
H8A | 0.576921 | 0.431322 | 0.291939 | 0.055* | |
H8B | 0.685619 | 0.427387 | 0.231077 | 0.055* | |
C9 | 0.8241 (3) | 0.51415 (16) | 0.3220 (3) | 0.0506 (10) | |
H9A | 0.875290 | 0.490380 | 0.287377 | 0.061* | |
H9B | 0.879334 | 0.531571 | 0.381165 | 0.061* | |
C10 | 0.7615 (3) | 0.56009 (15) | 0.2497 (3) | 0.0437 (9) | |
H10A | 0.716702 | 0.586020 | 0.286126 | 0.052* | |
H10B | 0.825224 | 0.581826 | 0.225187 | 0.052* | |
C11 | 0.1383 (3) | 0.57882 (14) | 0.0931 (3) | 0.0378 (8) | |
C12 | 0.0736 (3) | 0.62745 (16) | 0.1107 (3) | 0.0500 (10) | |
H12 | 0.060684 | 0.634674 | 0.176404 | 0.060* | |
C13 | 0.0276 (4) | 0.66576 (16) | 0.0312 (3) | 0.0604 (11) | |
H13 | −0.014418 | 0.698638 | 0.044310 | 0.072* | |
C14 | 0.0443 (4) | 0.65500 (19) | −0.0669 (3) | 0.0609 (12) | |
H14 | 0.012708 | 0.680304 | −0.120126 | 0.073* | |
C15 | 0.1071 (3) | 0.60727 (17) | −0.0854 (3) | 0.0519 (10) | |
H15 | 0.117968 | 0.600061 | −0.151708 | 0.062* | |
C16 | 0.1549 (3) | 0.56928 (15) | −0.0072 (3) | 0.0435 (9) | |
H16 | 0.198547 | 0.537080 | −0.021249 | 0.052* | |
C17 | 0.1510 (4) | 0.48047 (15) | 0.1505 (3) | 0.0540 (10) | |
H17A | 0.154730 | 0.470809 | 0.080323 | 0.065* | |
H17B | 0.064339 | 0.476153 | 0.157480 | 0.065* | |
C18 | 0.2346 (4) | 0.44063 (16) | 0.2238 (3) | 0.0516 (10) | |
H18A | 0.203871 | 0.401837 | 0.210497 | 0.062* | |
H18B | 0.319385 | 0.442244 | 0.211451 | 0.062* | |
C19 | 0.1817 (3) | 0.55429 (15) | 0.2758 (3) | 0.0441 (9) | |
H19A | 0.094917 | 0.550003 | 0.282589 | 0.053* | |
H19B | 0.206022 | 0.593865 | 0.289794 | 0.053* | |
C20 | 0.2659 (3) | 0.51623 (15) | 0.3526 (3) | 0.0480 (9) | |
H20A | 0.353238 | 0.523724 | 0.350540 | 0.058* | |
H20B | 0.254904 | 0.525406 | 0.421236 | 0.058* | |
C21 | 0.5418 (3) | 0.35843 (13) | 0.5875 (2) | 0.0330 (7) | |
C22 | 0.6116 (3) | 0.31980 (14) | 0.5442 (3) | 0.0403 (8) | |
H22 | 0.609882 | 0.321699 | 0.474075 | 0.048* | |
C23 | 0.6838 (3) | 0.27831 (14) | 0.6037 (3) | 0.0421 (9) | |
H23 | 0.730730 | 0.252638 | 0.573877 | 0.050* | |
C24 | 0.6857 (3) | 0.27537 (14) | 0.7075 (3) | 0.0378 (8) | |
C25 | 0.6173 (3) | 0.31365 (15) | 0.7525 (3) | 0.0422 (9) | |
H25 | 0.618742 | 0.311707 | 0.822587 | 0.051* | |
C26 | 0.5467 (3) | 0.35490 (15) | 0.6916 (3) | 0.0439 (9) | |
H26 | 0.501084 | 0.381014 | 0.721785 | 0.053* | |
C27 | 0.4575 (3) | 0.40162 (15) | 0.5219 (3) | 0.0393 (8) | |
C28 | 1.0539 (3) | 0.35016 (13) | 0.5371 (2) | 0.0332 (7) | |
C29 | 1.0084 (3) | 0.32960 (15) | 0.6197 (3) | 0.0435 (9) | |
H29 | 0.927288 | 0.339430 | 0.625776 | 0.052* | |
C30 | 1.0812 (3) | 0.29473 (14) | 0.6934 (3) | 0.0436 (9) | |
H30 | 1.050319 | 0.282046 | 0.749431 | 0.052* | |
C31 | 1.2002 (3) | 0.27904 (13) | 0.6825 (3) | 0.0365 (8) | |
C32 | 1.2455 (3) | 0.29675 (14) | 0.5995 (3) | 0.0411 (8) | |
H32 | 1.324481 | 0.284729 | 0.591371 | 0.049* | |
C33 | 1.1730 (3) | 0.33275 (14) | 0.5275 (3) | 0.0413 (8) | |
H33 | 1.204660 | 0.345427 | 0.471774 | 0.050* | |
C34 | 0.9773 (3) | 0.39127 (14) | 0.4615 (3) | 0.0419 (9) | |
I1 | 0.78561 (3) | 0.21027 (2) | 0.79917 (2) | 0.05702 (10) | |
I2 | 1.31203 (3) | 0.22704 (2) | 0.79616 (2) | 0.05455 (10) | |
N1 | 0.6722 (2) | 0.53483 (12) | 0.1613 (2) | 0.0367 (7) | |
N2 | 0.7303 (3) | 0.47858 (13) | 0.3568 (2) | 0.0450 (8) | |
H21N | 0.684 (3) | 0.4978 (14) | 0.392 (2) | 0.054* | |
H22N | 0.771 (3) | 0.4508 (12) | 0.397 (2) | 0.054* | |
N3 | 0.1911 (2) | 0.53973 (11) | 0.1718 (2) | 0.0367 (7) | |
N4 | 0.2388 (3) | 0.45488 (14) | 0.3322 (2) | 0.0460 (8) | |
H41N | 0.300 (3) | 0.4353 (14) | 0.370 (2) | 0.055* | |
H42N | 0.170 (2) | 0.4466 (15) | 0.350 (3) | 0.055* | |
O1 | 0.4122 (2) | 0.44040 (11) | 0.56598 (19) | 0.0571 (7) | |
O2 | 0.4359 (2) | 0.39436 (11) | 0.42592 (19) | 0.0561 (7) | |
O3 | 1.0238 (2) | 0.41261 (12) | 0.3931 (2) | 0.0644 (8) | |
O4 | 0.8680 (2) | 0.40136 (11) | 0.4733 (2) | 0.0645 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.043 (2) | 0.033 (2) | 0.0308 (18) | −0.0001 (16) | 0.0052 (16) | −0.0052 (15) |
C2 | 0.039 (2) | 0.046 (2) | 0.041 (2) | −0.0046 (17) | 0.0016 (17) | −0.0035 (17) |
C3 | 0.051 (2) | 0.056 (3) | 0.047 (2) | 0.003 (2) | −0.0029 (19) | 0.004 (2) |
C4 | 0.071 (3) | 0.055 (3) | 0.046 (2) | 0.009 (2) | 0.004 (2) | 0.0126 (19) |
C5 | 0.059 (3) | 0.062 (3) | 0.055 (3) | −0.001 (2) | 0.018 (2) | 0.016 (2) |
C6 | 0.045 (2) | 0.053 (2) | 0.047 (2) | 0.0058 (19) | 0.0084 (19) | 0.0039 (19) |
C7 | 0.039 (2) | 0.040 (2) | 0.038 (2) | −0.0020 (16) | 0.0033 (16) | −0.0034 (16) |
C8 | 0.049 (2) | 0.043 (2) | 0.047 (2) | −0.0008 (18) | 0.0116 (19) | 0.0044 (18) |
C9 | 0.051 (2) | 0.045 (2) | 0.047 (2) | −0.0004 (19) | −0.0076 (19) | −0.0001 (18) |
C10 | 0.045 (2) | 0.040 (2) | 0.041 (2) | −0.0041 (17) | −0.0035 (17) | −0.0029 (17) |
C11 | 0.0287 (18) | 0.034 (2) | 0.045 (2) | −0.0064 (15) | −0.0052 (16) | 0.0021 (16) |
C12 | 0.052 (2) | 0.041 (2) | 0.052 (2) | 0.0060 (18) | −0.0013 (19) | 0.0017 (18) |
C13 | 0.055 (3) | 0.038 (2) | 0.079 (3) | 0.0053 (19) | −0.007 (2) | 0.008 (2) |
C14 | 0.055 (3) | 0.056 (3) | 0.063 (3) | −0.005 (2) | −0.006 (2) | 0.025 (2) |
C15 | 0.047 (2) | 0.055 (3) | 0.050 (2) | −0.011 (2) | 0.0033 (19) | 0.015 (2) |
C16 | 0.038 (2) | 0.042 (2) | 0.048 (2) | −0.0036 (16) | 0.0020 (18) | 0.0056 (17) |
C17 | 0.068 (3) | 0.036 (2) | 0.047 (2) | −0.0018 (19) | −0.011 (2) | 0.0027 (17) |
C18 | 0.069 (3) | 0.035 (2) | 0.045 (2) | 0.0006 (18) | −0.001 (2) | 0.0045 (17) |
C19 | 0.047 (2) | 0.042 (2) | 0.040 (2) | 0.0026 (17) | 0.0040 (18) | 0.0009 (17) |
C20 | 0.054 (2) | 0.048 (2) | 0.037 (2) | 0.0068 (19) | −0.0002 (18) | 0.0008 (17) |
C21 | 0.0347 (18) | 0.0315 (19) | 0.0323 (18) | −0.0013 (15) | 0.0060 (15) | −0.0008 (15) |
C22 | 0.042 (2) | 0.045 (2) | 0.0341 (19) | 0.0010 (17) | 0.0088 (16) | −0.0007 (16) |
C23 | 0.050 (2) | 0.035 (2) | 0.043 (2) | 0.0115 (16) | 0.0121 (18) | −0.0007 (16) |
C24 | 0.0397 (19) | 0.0293 (19) | 0.0396 (19) | −0.0034 (15) | −0.0018 (16) | 0.0035 (15) |
C25 | 0.051 (2) | 0.045 (2) | 0.0300 (18) | 0.0019 (18) | 0.0073 (17) | −0.0025 (16) |
C26 | 0.049 (2) | 0.043 (2) | 0.040 (2) | 0.0125 (17) | 0.0076 (17) | −0.0043 (17) |
C27 | 0.037 (2) | 0.038 (2) | 0.041 (2) | 0.0022 (16) | 0.0039 (17) | 0.0011 (16) |
C28 | 0.0345 (18) | 0.0255 (18) | 0.0378 (19) | −0.0007 (15) | 0.0040 (16) | −0.0040 (14) |
C29 | 0.040 (2) | 0.038 (2) | 0.057 (2) | 0.0005 (17) | 0.0202 (18) | −0.0016 (18) |
C30 | 0.056 (2) | 0.034 (2) | 0.046 (2) | 0.0014 (18) | 0.0232 (19) | 0.0025 (17) |
C31 | 0.049 (2) | 0.0234 (18) | 0.0368 (19) | −0.0023 (15) | 0.0091 (17) | −0.0032 (14) |
C32 | 0.0384 (19) | 0.041 (2) | 0.045 (2) | 0.0062 (16) | 0.0121 (17) | 0.0039 (17) |
C33 | 0.047 (2) | 0.040 (2) | 0.039 (2) | 0.0017 (17) | 0.0147 (17) | 0.0038 (16) |
C34 | 0.043 (2) | 0.032 (2) | 0.048 (2) | −0.0049 (16) | 0.0022 (19) | −0.0041 (17) |
I1 | 0.0741 (2) | 0.03693 (15) | 0.05275 (17) | 0.00927 (12) | −0.00227 (14) | 0.00844 (12) |
I2 | 0.07106 (19) | 0.04819 (17) | 0.04096 (15) | 0.00624 (13) | 0.00451 (13) | 0.00842 (11) |
N1 | 0.0384 (16) | 0.0353 (17) | 0.0340 (15) | −0.0029 (13) | 0.0024 (13) | −0.0008 (13) |
N2 | 0.055 (2) | 0.039 (2) | 0.0394 (18) | 0.0156 (15) | 0.0074 (16) | 0.0050 (14) |
N3 | 0.0403 (16) | 0.0308 (16) | 0.0344 (15) | −0.0016 (13) | −0.0020 (13) | −0.0011 (12) |
N4 | 0.0415 (19) | 0.050 (2) | 0.0430 (19) | 0.0044 (16) | 0.0021 (16) | 0.0144 (15) |
O1 | 0.0706 (18) | 0.0487 (17) | 0.0495 (16) | 0.0268 (14) | 0.0076 (14) | −0.0019 (13) |
O2 | 0.0652 (18) | 0.0619 (18) | 0.0362 (15) | 0.0221 (14) | 0.0001 (13) | 0.0015 (13) |
O3 | 0.0583 (18) | 0.074 (2) | 0.0632 (18) | 0.0164 (15) | 0.0181 (15) | 0.0297 (16) |
O4 | 0.0441 (16) | 0.0659 (19) | 0.085 (2) | 0.0157 (14) | 0.0169 (15) | 0.0297 (16) |
C1—C2 | 1.380 (4) | C18—N4 | 1.472 (4) |
C1—C6 | 1.393 (5) | C18—H18A | 0.9700 |
C1—N1 | 1.422 (4) | C18—H18B | 0.9700 |
C2—C3 | 1.383 (5) | C19—N3 | 1.450 (4) |
C2—H2 | 0.9300 | C19—C20 | 1.506 (5) |
C3—C4 | 1.376 (5) | C19—H19A | 0.9700 |
C3—H3 | 0.9300 | C19—H19B | 0.9700 |
C4—C5 | 1.377 (5) | C20—N4 | 1.479 (5) |
C4—H4 | 0.9300 | C20—H20A | 0.9700 |
C5—C6 | 1.367 (5) | C20—H20B | 0.9700 |
C5—H5 | 0.9300 | C21—C26 | 1.377 (4) |
C6—H6 | 0.9300 | C21—C22 | 1.382 (4) |
C7—N1 | 1.458 (4) | C21—C27 | 1.509 (4) |
C7—C8 | 1.514 (4) | C22—C23 | 1.384 (4) |
C7—H7A | 0.9700 | C22—H22 | 0.9300 |
C7—H7B | 0.9700 | C23—C24 | 1.378 (4) |
C8—N2 | 1.485 (4) | C23—H23 | 0.9300 |
C8—H8A | 0.9700 | C24—C25 | 1.380 (5) |
C8—H8B | 0.9700 | C24—I1 | 2.101 (3) |
C9—N2 | 1.465 (5) | C25—C26 | 1.381 (4) |
C9—C10 | 1.503 (5) | C25—H25 | 0.9300 |
C9—H9A | 0.9700 | C26—H26 | 0.9300 |
C9—H9B | 0.9700 | C27—O1 | 1.238 (4) |
C10—N1 | 1.477 (4) | C27—O2 | 1.258 (4) |
C10—H10A | 0.9700 | C28—C29 | 1.385 (4) |
C10—H10B | 0.9700 | C28—C33 | 1.387 (4) |
C11—C12 | 1.384 (5) | C28—C34 | 1.506 (5) |
C11—C16 | 1.403 (5) | C29—C30 | 1.384 (5) |
C11—N3 | 1.415 (4) | C29—H29 | 0.9300 |
C12—C13 | 1.394 (5) | C30—C31 | 1.380 (5) |
C12—H12 | 0.9300 | C30—H30 | 0.9300 |
C13—C14 | 1.378 (6) | C31—C32 | 1.366 (4) |
C13—H13 | 0.9300 | C31—I2 | 2.109 (3) |
C14—C15 | 1.358 (5) | C32—C33 | 1.386 (4) |
C14—H14 | 0.9300 | C32—H32 | 0.9300 |
C15—C16 | 1.381 (5) | C33—H33 | 0.9300 |
C15—H15 | 0.9300 | C34—O3 | 1.237 (4) |
C16—H16 | 0.9300 | C34—O4 | 1.253 (4) |
C17—N3 | 1.463 (4) | N2—H21N | 0.877 (18) |
C17—C18 | 1.503 (5) | N2—H22N | 0.897 (18) |
C17—H17A | 0.9700 | N4—H41N | 0.869 (18) |
C17—H17B | 0.9700 | N4—H42N | 0.851 (18) |
C2—C1—C6 | 117.7 (3) | N3—C19—C20 | 110.5 (3) |
C2—C1—N1 | 124.0 (3) | N3—C19—H19A | 109.5 |
C6—C1—N1 | 118.3 (3) | C20—C19—H19A | 109.5 |
C1—C2—C3 | 120.8 (3) | N3—C19—H19B | 109.5 |
C1—C2—H2 | 119.6 | C20—C19—H19B | 109.5 |
C3—C2—H2 | 119.6 | H19A—C19—H19B | 108.1 |
C4—C3—C2 | 120.6 (4) | N4—C20—C19 | 112.5 (3) |
C4—C3—H3 | 119.7 | N4—C20—H20A | 109.1 |
C2—C3—H3 | 119.7 | C19—C20—H20A | 109.1 |
C3—C4—C5 | 119.0 (4) | N4—C20—H20B | 109.1 |
C3—C4—H4 | 120.5 | C19—C20—H20B | 109.1 |
C5—C4—H4 | 120.5 | H20A—C20—H20B | 107.8 |
C6—C5—C4 | 120.4 (4) | C26—C21—C22 | 118.3 (3) |
C6—C5—H5 | 119.8 | C26—C21—C27 | 120.6 (3) |
C4—C5—H5 | 119.8 | C22—C21—C27 | 121.0 (3) |
C5—C6—C1 | 121.5 (3) | C21—C22—C23 | 120.9 (3) |
C5—C6—H6 | 119.3 | C21—C22—H22 | 119.5 |
C1—C6—H6 | 119.3 | C23—C22—H22 | 119.5 |
N1—C7—C8 | 110.7 (3) | C24—C23—C22 | 119.5 (3) |
N1—C7—H7A | 109.5 | C24—C23—H23 | 120.3 |
C8—C7—H7A | 109.5 | C22—C23—H23 | 120.3 |
N1—C7—H7B | 109.5 | C23—C24—C25 | 120.6 (3) |
C8—C7—H7B | 109.5 | C23—C24—I1 | 120.8 (2) |
H7A—C7—H7B | 108.1 | C25—C24—I1 | 118.5 (3) |
N2—C8—C7 | 110.1 (3) | C24—C25—C26 | 118.8 (3) |
N2—C8—H8A | 109.6 | C24—C25—H25 | 120.6 |
C7—C8—H8A | 109.6 | C26—C25—H25 | 120.6 |
N2—C8—H8B | 109.6 | C21—C26—C25 | 121.8 (3) |
C7—C8—H8B | 109.6 | C21—C26—H26 | 119.1 |
H8A—C8—H8B | 108.2 | C25—C26—H26 | 119.1 |
N2—C9—C10 | 111.1 (3) | O1—C27—O2 | 125.0 (3) |
N2—C9—H9A | 109.4 | O1—C27—C21 | 118.0 (3) |
C10—C9—H9A | 109.4 | O2—C27—C21 | 116.9 (3) |
N2—C9—H9B | 109.4 | C29—C28—C33 | 118.1 (3) |
C10—C9—H9B | 109.4 | C29—C28—C34 | 120.8 (3) |
H9A—C9—H9B | 108.0 | C33—C28—C34 | 121.1 (3) |
N1—C10—C9 | 110.6 (3) | C30—C29—C28 | 121.3 (3) |
N1—C10—H10A | 109.5 | C30—C29—H29 | 119.3 |
C9—C10—H10A | 109.5 | C28—C29—H29 | 119.3 |
N1—C10—H10B | 109.5 | C31—C30—C29 | 119.1 (3) |
C9—C10—H10B | 109.5 | C31—C30—H30 | 120.5 |
H10A—C10—H10B | 108.1 | C29—C30—H30 | 120.5 |
C12—C11—C16 | 117.8 (3) | C32—C31—C30 | 120.8 (3) |
C12—C11—N3 | 123.1 (3) | C32—C31—I2 | 120.2 (2) |
C16—C11—N3 | 119.1 (3) | C30—C31—I2 | 119.0 (3) |
C11—C12—C13 | 120.8 (4) | C31—C32—C33 | 119.5 (3) |
C11—C12—H12 | 119.6 | C31—C32—H32 | 120.2 |
C13—C12—H12 | 119.6 | C33—C32—H32 | 120.2 |
C14—C13—C12 | 120.1 (4) | C32—C33—C28 | 121.1 (3) |
C14—C13—H13 | 119.9 | C32—C33—H33 | 119.5 |
C12—C13—H13 | 119.9 | C28—C33—H33 | 119.5 |
C15—C14—C13 | 119.7 (4) | O3—C34—O4 | 124.4 (3) |
C15—C14—H14 | 120.1 | O3—C34—C28 | 119.7 (3) |
C13—C14—H14 | 120.1 | O4—C34—C28 | 115.9 (3) |
C14—C15—C16 | 120.9 (4) | C1—N1—C7 | 115.5 (3) |
C14—C15—H15 | 119.5 | C1—N1—C10 | 112.3 (3) |
C16—C15—H15 | 119.5 | C7—N1—C10 | 111.1 (3) |
C15—C16—C11 | 120.6 (4) | C9—N2—C8 | 110.8 (3) |
C15—C16—H16 | 119.7 | C9—N2—H21N | 113 (2) |
C11—C16—H16 | 119.7 | C8—N2—H21N | 106 (2) |
N3—C17—C18 | 110.5 (3) | C9—N2—H22N | 108 (2) |
N3—C17—H17A | 109.5 | C8—N2—H22N | 110 (2) |
C18—C17—H17A | 109.5 | H21N—N2—H22N | 109 (3) |
N3—C17—H17B | 109.5 | C11—N3—C19 | 116.9 (3) |
C18—C17—H17B | 109.5 | C11—N3—C17 | 114.5 (3) |
H17A—C17—H17B | 108.1 | C19—N3—C17 | 109.1 (3) |
N4—C18—C17 | 112.4 (3) | C18—N4—C20 | 111.3 (3) |
N4—C18—H18A | 109.1 | C18—N4—H41N | 108 (2) |
C17—C18—H18A | 109.1 | C20—N4—H41N | 108 (2) |
N4—C18—H18B | 109.1 | C18—N4—H42N | 112 (3) |
C17—C18—H18B | 109.1 | C20—N4—H42N | 109 (3) |
H18A—C18—H18B | 107.9 | H41N—N4—H42N | 109 (3) |
C6—C1—C2—C3 | −0.2 (5) | C33—C28—C29—C30 | 2.8 (5) |
N1—C1—C2—C3 | −179.4 (3) | C34—C28—C29—C30 | −175.8 (3) |
C1—C2—C3—C4 | −0.6 (6) | C28—C29—C30—C31 | −1.7 (5) |
C2—C3—C4—C5 | 0.6 (6) | C29—C30—C31—C32 | −1.0 (5) |
C3—C4—C5—C6 | 0.2 (6) | C29—C30—C31—I2 | 179.0 (3) |
C4—C5—C6—C1 | −1.1 (6) | C30—C31—C32—C33 | 2.6 (5) |
C2—C1—C6—C5 | 1.1 (5) | I2—C31—C32—C33 | −177.5 (3) |
N1—C1—C6—C5 | −179.7 (3) | C31—C32—C33—C28 | −1.4 (5) |
N1—C7—C8—N2 | 56.9 (4) | C29—C28—C33—C32 | −1.3 (5) |
N2—C9—C10—N1 | −56.4 (4) | C34—C28—C33—C32 | 177.3 (3) |
C16—C11—C12—C13 | −0.5 (5) | C29—C28—C34—O3 | 174.3 (3) |
N3—C11—C12—C13 | 177.5 (3) | C33—C28—C34—O3 | −4.3 (5) |
C11—C12—C13—C14 | 1.1 (6) | C29—C28—C34—O4 | −5.8 (5) |
C12—C13—C14—C15 | −0.8 (6) | C33—C28—C34—O4 | 175.6 (3) |
C13—C14—C15—C16 | −0.2 (6) | C2—C1—N1—C7 | 7.2 (4) |
C14—C15—C16—C11 | 0.8 (5) | C6—C1—N1—C7 | −172.0 (3) |
C12—C11—C16—C15 | −0.5 (5) | C2—C1—N1—C10 | −121.7 (3) |
N3—C11—C16—C15 | −178.5 (3) | C6—C1—N1—C10 | 59.2 (4) |
N3—C17—C18—N4 | 56.1 (4) | C8—C7—N1—C1 | 173.3 (3) |
N3—C19—C20—N4 | −55.9 (4) | C8—C7—N1—C10 | −57.3 (3) |
C26—C21—C22—C23 | 0.4 (5) | C9—C10—N1—C1 | −172.1 (3) |
C27—C21—C22—C23 | −176.6 (3) | C9—C10—N1—C7 | 56.8 (4) |
C21—C22—C23—C24 | 0.3 (5) | C10—C9—N2—C8 | 56.7 (4) |
C22—C23—C24—C25 | −0.6 (5) | C7—C8—N2—C9 | −56.5 (4) |
C22—C23—C24—I1 | 176.5 (2) | C12—C11—N3—C19 | −3.6 (5) |
C23—C24—C25—C26 | 0.2 (5) | C16—C11—N3—C19 | 174.3 (3) |
I1—C24—C25—C26 | −177.0 (3) | C12—C11—N3—C17 | 125.8 (4) |
C22—C21—C26—C25 | −0.9 (5) | C16—C11—N3—C17 | −56.2 (4) |
C27—C21—C26—C25 | 176.2 (3) | C20—C19—N3—C11 | −167.4 (3) |
C24—C25—C26—C21 | 0.6 (5) | C20—C19—N3—C17 | 60.7 (4) |
C26—C21—C27—O1 | 13.6 (5) | C18—C17—N3—C11 | 165.9 (3) |
C22—C21—C27—O1 | −169.4 (3) | C18—C17—N3—C19 | −60.9 (4) |
C26—C21—C27—O2 | −164.6 (3) | C17—C18—N4—C20 | −50.0 (4) |
C22—C21—C27—O2 | 12.4 (5) | C19—C20—N4—C18 | 49.9 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O3 | 0.97 | 2.63 | 3.218 (4) | 119 |
N2—H21N···O1i | 0.88 (2) | 1.94 (2) | 2.780 (4) | 160 (3) |
N2—H22N···O4 | 0.90 (2) | 1.74 (2) | 2.627 (4) | 173 (3) |
N4—H41N···O1 | 0.87 (2) | 2.63 (3) | 3.285 (4) | 133 (3) |
N4—H41N···O2 | 0.87 (2) | 1.78 (2) | 2.643 (4) | 169 (3) |
N4—H42N···O3ii | 0.85 (2) | 1.97 (2) | 2.809 (4) | 169 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z. |
C10H15N2+·C7H4NO4− | F(000) = 696 |
Mr = 329.35 | Dx = 1.343 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.0683 (9) Å | Cell parameters from 4084 reflections |
b = 15.7868 (9) Å | θ = 2.6–27.9° |
c = 7.9255 (5) Å | µ = 0.10 mm−1 |
β = 95.137 (6)° | T = 293 K |
V = 1628.52 (18) Å3 | Prism, yellow |
Z = 4 | 0.48 × 0.44 × 0.16 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 2088 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.035 |
Rotation method data acquisition using ω scans. | θmax = 28.0°, θmin = 2.9° |
Absorption correction: multi-scan (CrysalisRED; Oxford Diffraction, 2007) | h = −12→17 |
Tmin = 0.790, Tmax = 1.000 | k = −19→20 |
11699 measured reflections | l = −10→10 |
3587 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: mixed |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0406P)2 + 0.2296P] where P = (Fo2 + 2Fc2)/3 |
3587 reflections | (Δ/σ)max < 0.001 |
251 parameters | Δρmax = 0.15 e Å−3 |
83 restraints | Δρmin = −0.13 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 | Occ. (<1) | |
N1 | 0.31713 (11) | 0.63737 (9) | 0.06853 (18) | 0.0443 (4) | |
N2 | 0.42384 (12) | 0.61812 (10) | 0.3978 (2) | 0.0497 (4) | |
H21 | 0.4059 (14) | 0.5640 (10) | 0.412 (2) | 0.060* | |
H22 | 0.4650 (13) | 0.6358 (11) | 0.493 (2) | 0.060* | |
C1 | 0.25304 (14) | 0.61655 (11) | −0.0794 (2) | 0.0451 (5) | |
C2 | 0.16112 (15) | 0.66029 (13) | −0.1177 (3) | 0.0592 (5) | |
H2 | 0.141977 | 0.702437 | −0.044776 | 0.071* | |
C3 | 0.09843 (17) | 0.64191 (16) | −0.2618 (3) | 0.0711 (7) | |
H3 | 0.037601 | 0.671965 | −0.285079 | 0.085* | |
C4 | 0.12406 (19) | 0.58034 (18) | −0.3709 (3) | 0.0786 (7) | |
H4 | 0.080984 | 0.567936 | −0.467562 | 0.094* | |
C5 | 0.21412 (19) | 0.53709 (16) | −0.3360 (3) | 0.0769 (7) | |
H5 | 0.232309 | 0.495042 | −0.409926 | 0.092* | |
C6 | 0.27853 (16) | 0.55500 (13) | −0.1925 (2) | 0.0603 (6) | |
H6 | 0.339789 | 0.525251 | −0.171661 | 0.072* | |
C7 | 0.41360 (13) | 0.59047 (11) | 0.0927 (2) | 0.0482 (5) | |
H7A | 0.450391 | 0.596351 | −0.007625 | 0.058* | |
H7B | 0.398842 | 0.530823 | 0.107119 | 0.058* | |
C8 | 0.48078 (14) | 0.62161 (12) | 0.2451 (2) | 0.0546 (5) | |
H8A | 0.541877 | 0.586642 | 0.261820 | 0.066* | |
H8B | 0.502144 | 0.679404 | 0.226049 | 0.066* | |
C9 | 0.33189 (14) | 0.67211 (12) | 0.3727 (2) | 0.0551 (5) | |
H9A | 0.352164 | 0.730174 | 0.353462 | 0.066* | |
H9B | 0.294913 | 0.670810 | 0.473427 | 0.066* | |
C10 | 0.26333 (14) | 0.64092 (12) | 0.2229 (2) | 0.0525 (5) | |
H10A | 0.238174 | 0.584849 | 0.247440 | 0.063* | |
H10B | 0.204495 | 0.678299 | 0.204255 | 0.063* | |
O1 | 0.54550 (10) | 0.66915 (8) | 0.67450 (17) | 0.0659 (4) | |
O2 | 0.62576 (10) | 0.55694 (8) | 0.58251 (17) | 0.0596 (4) | |
N3 | 0.9330 (8) | 0.6415 (18) | 1.2296 (16) | 0.0790 (18) | 0.62 (3) |
O3 | 0.9183 (12) | 0.6862 (8) | 1.3520 (19) | 0.108 (3) | 0.62 (3) |
O4 | 1.0096 (8) | 0.5973 (11) | 1.2186 (12) | 0.095 (2) | 0.62 (3) |
N3A | 0.9219 (15) | 0.647 (3) | 1.244 (3) | 0.082 (3) | 0.38 (3) |
O3A | 0.8898 (15) | 0.6659 (14) | 1.380 (2) | 0.095 (3) | 0.38 (3) |
O4A | 1.0127 (12) | 0.6352 (18) | 1.223 (2) | 0.101 (3) | 0.38 (3) |
C11 | 0.70169 (13) | 0.62778 (10) | 0.8251 (2) | 0.0422 (4) | |
C12 | 0.68311 (14) | 0.67242 (11) | 0.9690 (2) | 0.0505 (5) | |
H12 | 0.620157 | 0.699232 | 0.974825 | 0.061* | |
C13 | 0.75707 (16) | 0.67767 (12) | 1.1045 (3) | 0.0591 (5) | |
H13 | 0.744175 | 0.706602 | 1.202574 | 0.071* | |
C14 | 0.84977 (16) | 0.63922 (13) | 1.0907 (3) | 0.0567 (5) | |
C15 | 0.87192 (15) | 0.59666 (13) | 0.9479 (3) | 0.0603 (6) | |
H15 | 0.936114 | 0.572184 | 0.940687 | 0.072* | |
C16 | 0.79686 (14) | 0.59106 (12) | 0.8155 (2) | 0.0523 (5) | |
H16 | 0.810377 | 0.562065 | 0.717750 | 0.063* | |
C17 | 0.61816 (14) | 0.61734 (11) | 0.6823 (2) | 0.0465 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0417 (9) | 0.0431 (8) | 0.0468 (9) | 0.0018 (7) | −0.0038 (7) | 0.0015 (7) |
N2 | 0.0525 (10) | 0.0434 (9) | 0.0505 (10) | 0.0009 (7) | −0.0110 (8) | −0.0029 (8) |
C1 | 0.0461 (11) | 0.0442 (10) | 0.0437 (11) | −0.0081 (8) | −0.0027 (8) | 0.0094 (9) |
C2 | 0.0514 (12) | 0.0637 (13) | 0.0606 (13) | −0.0023 (10) | −0.0057 (10) | 0.0071 (11) |
C3 | 0.0526 (14) | 0.0923 (17) | 0.0657 (16) | −0.0093 (12) | −0.0104 (11) | 0.0187 (14) |
C4 | 0.0733 (17) | 0.112 (2) | 0.0476 (14) | −0.0251 (15) | −0.0141 (12) | 0.0100 (14) |
C5 | 0.092 (2) | 0.0928 (18) | 0.0446 (13) | −0.0129 (14) | −0.0014 (12) | −0.0059 (12) |
C6 | 0.0661 (14) | 0.0663 (13) | 0.0472 (12) | 0.0008 (10) | −0.0018 (10) | 0.0001 (11) |
C7 | 0.0458 (11) | 0.0493 (10) | 0.0489 (12) | 0.0022 (9) | 0.0014 (8) | 0.0022 (9) |
C8 | 0.0457 (12) | 0.0565 (12) | 0.0603 (13) | 0.0002 (9) | −0.0025 (10) | 0.0042 (10) |
C9 | 0.0561 (12) | 0.0510 (11) | 0.0562 (12) | 0.0111 (9) | −0.0070 (9) | −0.0086 (10) |
C10 | 0.0478 (12) | 0.0564 (12) | 0.0522 (12) | 0.0093 (9) | −0.0026 (9) | −0.0065 (9) |
O1 | 0.0597 (9) | 0.0622 (8) | 0.0710 (10) | 0.0133 (7) | −0.0213 (7) | −0.0130 (7) |
O2 | 0.0715 (10) | 0.0475 (7) | 0.0567 (9) | 0.0020 (7) | −0.0117 (7) | −0.0087 (7) |
N3 | 0.068 (4) | 0.100 (5) | 0.065 (3) | −0.018 (4) | −0.019 (3) | 0.005 (3) |
O3 | 0.106 (5) | 0.126 (5) | 0.084 (5) | −0.009 (4) | −0.036 (4) | −0.028 (4) |
O4 | 0.056 (3) | 0.140 (6) | 0.084 (3) | 0.000 (4) | −0.0213 (18) | 0.014 (4) |
N3A | 0.064 (5) | 0.105 (6) | 0.071 (5) | −0.007 (5) | −0.024 (5) | 0.007 (5) |
O3A | 0.091 (7) | 0.124 (7) | 0.066 (5) | −0.011 (5) | −0.025 (4) | −0.011 (5) |
O4A | 0.050 (4) | 0.146 (8) | 0.102 (5) | −0.018 (6) | −0.023 (3) | 0.020 (6) |
C11 | 0.0450 (11) | 0.0361 (9) | 0.0444 (11) | −0.0045 (8) | −0.0029 (8) | 0.0032 (8) |
C12 | 0.0491 (12) | 0.0475 (11) | 0.0538 (12) | 0.0021 (9) | −0.0014 (9) | −0.0022 (9) |
C13 | 0.0690 (15) | 0.0557 (12) | 0.0510 (12) | −0.0014 (11) | −0.0046 (10) | −0.0104 (10) |
C14 | 0.0520 (13) | 0.0599 (13) | 0.0550 (13) | −0.0116 (10) | −0.0127 (10) | 0.0058 (10) |
C15 | 0.0414 (12) | 0.0722 (14) | 0.0664 (15) | 0.0017 (10) | −0.0008 (10) | 0.0060 (12) |
C16 | 0.0500 (12) | 0.0564 (12) | 0.0500 (12) | 0.0033 (10) | 0.0016 (9) | −0.0033 (9) |
C17 | 0.0498 (12) | 0.0389 (10) | 0.0492 (12) | −0.0040 (9) | −0.0044 (9) | 0.0045 (9) |
N1—C1 | 1.417 (2) | C9—H9A | 0.9700 |
N1—C7 | 1.460 (2) | C9—H9B | 0.9700 |
N1—C10 | 1.466 (2) | C10—H10A | 0.9700 |
N2—C9 | 1.472 (2) | C10—H10B | 0.9700 |
N2—C8 | 1.477 (3) | O1—C17 | 1.250 (2) |
N2—H21 | 0.896 (14) | O2—C17 | 1.248 (2) |
N2—H22 | 0.931 (14) | N3—O4 | 1.229 (10) |
C1—C6 | 1.383 (3) | N3—O3 | 1.229 (9) |
C1—C2 | 1.395 (3) | N3—C14 | 1.477 (8) |
C2—C3 | 1.376 (3) | N3A—O4A | 1.229 (10) |
C2—H2 | 0.9300 | N3A—O3A | 1.229 (9) |
C3—C4 | 1.363 (3) | N3A—C14 | 1.474 (14) |
C3—H3 | 0.9300 | C11—C16 | 1.380 (2) |
C4—C5 | 1.367 (3) | C11—C12 | 1.381 (2) |
C4—H4 | 0.9300 | C11—C17 | 1.510 (2) |
C5—C6 | 1.383 (3) | C12—C13 | 1.381 (3) |
C5—H5 | 0.9300 | C12—H12 | 0.9300 |
C6—H6 | 0.9300 | C13—C14 | 1.368 (3) |
C7—C8 | 1.510 (2) | C13—H13 | 0.9300 |
C7—H7A | 0.9700 | C14—C15 | 1.370 (3) |
C7—H7B | 0.9700 | C15—C16 | 1.374 (3) |
C8—H8A | 0.9700 | C15—H15 | 0.9300 |
C8—H8B | 0.9700 | C16—H16 | 0.9300 |
C9—C10 | 1.504 (2) | ||
C1—N1—C7 | 115.50 (14) | N2—C9—H9A | 109.7 |
C1—N1—C10 | 114.03 (14) | C10—C9—H9A | 109.7 |
C7—N1—C10 | 112.51 (13) | N2—C9—H9B | 109.7 |
C9—N2—C8 | 109.43 (15) | C10—C9—H9B | 109.7 |
C9—N2—H21 | 110.4 (12) | H9A—C9—H9B | 108.2 |
C8—N2—H21 | 107.1 (13) | N1—C10—C9 | 112.01 (16) |
C9—N2—H22 | 110.0 (11) | N1—C10—H10A | 109.2 |
C8—N2—H22 | 110.9 (12) | C9—C10—H10A | 109.2 |
H21—N2—H22 | 108.9 (16) | N1—C10—H10B | 109.2 |
C6—C1—C2 | 117.37 (17) | C9—C10—H10B | 109.2 |
C6—C1—N1 | 122.71 (16) | H10A—C10—H10B | 107.9 |
C2—C1—N1 | 119.91 (17) | O4—N3—O3 | 124.7 (4) |
C3—C2—C1 | 120.9 (2) | O4—N3—C14 | 118.9 (9) |
C3—C2—H2 | 119.6 | O3—N3—C14 | 116.4 (9) |
C1—C2—H2 | 119.6 | O4A—N3A—O3A | 124.6 (5) |
C4—C3—C2 | 121.0 (2) | O4A—N3A—C14 | 115.4 (12) |
C4—C3—H3 | 119.5 | O3A—N3A—C14 | 120.0 (12) |
C2—C3—H3 | 119.5 | C16—C11—C12 | 119.07 (16) |
C3—C4—C5 | 118.9 (2) | C16—C11—C17 | 120.49 (17) |
C3—C4—H4 | 120.5 | C12—C11—C17 | 120.42 (17) |
C5—C4—H4 | 120.5 | C11—C12—C13 | 120.68 (18) |
C4—C5—C6 | 120.9 (2) | C11—C12—H12 | 119.7 |
C4—C5—H5 | 119.5 | C13—C12—H12 | 119.7 |
C6—C5—H5 | 119.5 | C14—C13—C12 | 118.33 (19) |
C5—C6—C1 | 120.9 (2) | C14—C13—H13 | 120.8 |
C5—C6—H6 | 119.6 | C12—C13—H13 | 120.8 |
C1—C6—H6 | 119.6 | C13—C14—C15 | 122.52 (18) |
N1—C7—C8 | 111.92 (15) | C13—C14—N3A | 113.8 (8) |
N1—C7—H7A | 109.2 | C15—C14—N3A | 123.7 (8) |
C8—C7—H7A | 109.2 | C13—C14—N3 | 121.9 (5) |
N1—C7—H7B | 109.2 | C15—C14—N3 | 115.6 (5) |
C8—C7—H7B | 109.2 | C14—C15—C16 | 118.29 (19) |
H7A—C7—H7B | 107.9 | C14—C15—H15 | 120.9 |
N2—C8—C7 | 110.09 (16) | C16—C15—H15 | 120.9 |
N2—C8—H8A | 109.6 | C15—C16—C11 | 121.07 (19) |
C7—C8—H8A | 109.6 | C15—C16—H16 | 119.5 |
N2—C8—H8B | 109.6 | C11—C16—H16 | 119.5 |
C7—C8—H8B | 109.6 | O2—C17—O1 | 124.86 (16) |
H8A—C8—H8B | 108.2 | O2—C17—C11 | 117.72 (16) |
N2—C9—C10 | 109.78 (15) | O1—C17—C11 | 117.41 (17) |
C7—N1—C1—C6 | 1.1 (2) | C11—C12—C13—C14 | 1.5 (3) |
C10—N1—C1—C6 | −131.49 (19) | C12—C13—C14—C15 | 0.6 (3) |
C7—N1—C1—C2 | −177.35 (16) | C12—C13—C14—N3A | −179 (2) |
C10—N1—C1—C2 | 50.0 (2) | C12—C13—C14—N3 | −179.8 (14) |
C6—C1—C2—C3 | 0.6 (3) | O4A—N3A—C14—C13 | −160 (3) |
N1—C1—C2—C3 | 179.11 (18) | O3A—N3A—C14—C13 | 18 (5) |
C1—C2—C3—C4 | 0.2 (3) | O4A—N3A—C14—C15 | 21 (5) |
C2—C3—C4—C5 | −0.6 (3) | O3A—N3A—C14—C15 | −161 (3) |
C3—C4—C5—C6 | 0.1 (4) | O4—N3—C14—C13 | 171.1 (17) |
C4—C5—C6—C1 | 0.7 (3) | O3—N3—C14—C13 | −7 (3) |
C2—C1—C6—C5 | −1.0 (3) | O4—N3—C14—C15 | −9 (3) |
N1—C1—C6—C5 | −179.50 (18) | O3—N3—C14—C15 | 173.1 (18) |
C1—N1—C7—C8 | 175.30 (15) | C13—C14—C15—C16 | −1.5 (3) |
C10—N1—C7—C8 | −51.4 (2) | N3A—C14—C15—C16 | 177 (2) |
C9—N2—C8—C7 | −60.00 (19) | N3—C14—C15—C16 | 178.8 (13) |
N1—C7—C8—N2 | 55.4 (2) | C14—C15—C16—C11 | 0.4 (3) |
C8—N2—C9—C10 | 60.4 (2) | C12—C11—C16—C15 | 1.5 (3) |
C1—N1—C10—C9 | −173.98 (14) | C17—C11—C16—C15 | −176.86 (17) |
C7—N1—C10—C9 | 52.0 (2) | C16—C11—C17—O2 | 20.4 (3) |
N2—C9—C10—N1 | −56.4 (2) | C12—C11—C17—O2 | −157.93 (17) |
C16—C11—C12—C13 | −2.5 (3) | C16—C11—C17—O1 | −160.75 (18) |
C17—C11—C12—C13 | 175.88 (17) | C12—C11—C17—O1 | 20.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O2i | 0.90 (1) | 1.96 (2) | 2.846 (2) | 173 (2) |
N2—H22···O1 | 0.93 (1) | 1.78 (2) | 2.7135 (19) | 179 (2) |
N2—H22···O2 | 0.93 (1) | 2.49 (2) | 3.057 (2) | 120 (1) |
C8—H8B···O1ii | 0.97 | 2.50 | 3.468 (2) | 176 |
C10—H10B···O4Aiii | 0.97 | 2.61 | 3.276 (15) | 126 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x−1, y, z−1. |
C10H15N2+·C7H3N2O7− | F(000) = 816 |
Mr = 390.35 | Dx = 1.444 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.779 (3) Å | Cell parameters from 1200 reflections |
b = 7.411 (3) Å | θ = 2.6–27.9° |
c = 31.357 (9) Å | µ = 0.11 mm−1 |
β = 96.82 (3)° | T = 293 K |
V = 1794.9 (11) Å3 | Prism, yellow |
Z = 4 | 0.20 × 0.18 × 0.12 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 1590 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.055 |
Rotation method data acquisition using ω scans. | θmax = 28.0°, θmin = 2.6° |
Absorption correction: multi-scan (CrysalisRED; Oxford Diffraction, 2007) | h = −9→9 |
Tmin = 0.959, Tmax = 1.000 | k = −9→9 |
7737 measured reflections | l = −40→26 |
3882 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.085 | Hydrogen site location: mixed |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0396P)2 + 0.7929P] where P = (Fo2 + 2Fc2)/3 |
3882 reflections | (Δ/σ)max < 0.001 |
321 parameters | Δρmax = 0.18 e Å−3 |
288 restraints | Δρmin = −0.20 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 | Occ. (<1) | |
O1 | 0.2174 (3) | 0.5690 (4) | 0.40623 (8) | 0.0678 (9) | |
O2 | 0.3815 (3) | 0.5542 (4) | 0.46760 (8) | 0.0644 (9) | |
H2O | 0.372 (5) | 0.581 (6) | 0.4933 (7) | 0.077* | |
O3 | 0.2737 (3) | 0.6604 (4) | 0.53481 (7) | 0.0538 (8) | |
N3 | 0.0028 (7) | 0.8237 (11) | 0.57913 (17) | 0.0504 (16) | 0.690 (11) |
O4 | 0.1059 (7) | 0.7315 (9) | 0.60356 (18) | 0.069 (2) | 0.690 (11) |
O5 | −0.0948 (7) | 0.9353 (9) | 0.5930 (2) | 0.0602 (19) | 0.690 (11) |
N3A | −0.0015 (11) | 0.825 (2) | 0.5769 (3) | 0.053 (3) | 0.310 (11) |
O4A | 0.1438 (10) | 0.818 (2) | 0.5983 (4) | 0.065 (4) | 0.310 (11) |
O5A | −0.1263 (11) | 0.898 (2) | 0.5910 (5) | 0.053 (4) | 0.310 (11) |
O6 | −0.4591 (3) | 0.9346 (4) | 0.45916 (8) | 0.0725 (9) | |
O7 | −0.3746 (3) | 0.8095 (4) | 0.40327 (8) | 0.0738 (9) | |
N4 | −0.3514 (4) | 0.8515 (5) | 0.44113 (10) | 0.0517 (9) | |
C11 | 0.0978 (4) | 0.6775 (5) | 0.46853 (11) | 0.0390 (9) | |
C12 | 0.1281 (4) | 0.7048 (5) | 0.51389 (11) | 0.0418 (9) | |
C13 | −0.0142 (4) | 0.7862 (5) | 0.53288 (10) | 0.0400 (9) | |
C14 | −0.1672 (4) | 0.8346 (5) | 0.50932 (11) | 0.0398 (9) | |
H14 | −0.254887 | 0.888430 | 0.522579 | 0.048* | |
C15 | −0.1890 (4) | 0.8024 (5) | 0.46600 (11) | 0.0393 (9) | |
C16 | −0.0579 (4) | 0.7232 (5) | 0.44552 (11) | 0.0413 (10) | |
H16 | −0.075920 | 0.701222 | 0.416128 | 0.050* | |
C17 | 0.2359 (5) | 0.5974 (5) | 0.44453 (12) | 0.0477 (10) | |
N1 | 0.6156 (4) | 0.6931 (4) | 0.70321 (9) | 0.0467 (8) | |
N2 | 0.4692 (4) | 0.6095 (6) | 0.61759 (11) | 0.0666 (11) | |
H21 | 0.387 (4) | 0.620 (5) | 0.5958 (9) | 0.080* | |
H22 | 0.548 (4) | 0.538 (4) | 0.6091 (11) | 0.080* | |
C1 | 0.7285 (5) | 0.6958 (7) | 0.74341 (14) | 0.0502 (14) | 0.687 (10) |
C2 | 0.8534 (7) | 0.8298 (8) | 0.75105 (14) | 0.0631 (17) | 0.687 (10) |
H2A | 0.863427 | 0.918478 | 0.730495 | 0.076* | 0.687 (10) |
C3 | 0.9631 (6) | 0.8314 (9) | 0.78940 (16) | 0.0671 (17) | 0.687 (10) |
H3A | 1.046662 | 0.921115 | 0.794514 | 0.081* | 0.687 (10) |
C4 | 0.9481 (6) | 0.6989 (9) | 0.82012 (14) | 0.0613 (17) | 0.687 (10) |
H4A | 1.021562 | 0.699993 | 0.845781 | 0.074* | 0.687 (10) |
C5 | 0.8233 (7) | 0.5649 (7) | 0.81248 (16) | 0.0652 (17) | 0.687 (10) |
H5A | 0.813228 | 0.476232 | 0.833028 | 0.078* | 0.687 (10) |
C6 | 0.7135 (7) | 0.5633 (7) | 0.77412 (17) | 0.0585 (16) | 0.687 (10) |
H6A | 0.629992 | 0.473592 | 0.769009 | 0.070* | 0.687 (10) |
C1A | 0.7263 (12) | 0.7159 (17) | 0.7414 (3) | 0.054 (2) | 0.313 (10) |
C2A | 0.8039 (15) | 0.8840 (16) | 0.7482 (3) | 0.062 (2) | 0.313 (10) |
H2AA | 0.782198 | 0.974477 | 0.727712 | 0.075* | 0.313 (10) |
C3A | 0.9139 (16) | 0.9170 (17) | 0.7856 (4) | 0.066 (2) | 0.313 (10) |
H3AA | 0.965778 | 1.029454 | 0.790219 | 0.080* | 0.313 (10) |
C4A | 0.9463 (13) | 0.782 (2) | 0.8163 (3) | 0.064 (2) | 0.313 (10) |
H4AA | 1.019913 | 0.803779 | 0.841325 | 0.076* | 0.313 (10) |
C5A | 0.8688 (16) | 0.6136 (17) | 0.8094 (4) | 0.059 (2) | 0.313 (10) |
H5AA | 0.890467 | 0.523125 | 0.829924 | 0.070* | 0.313 (10) |
C6A | 0.7588 (16) | 0.5806 (15) | 0.7720 (4) | 0.059 (2) | 0.313 (10) |
H6AA | 0.706886 | 0.468144 | 0.767417 | 0.071* | 0.313 (10) |
C7 | 0.5365 (5) | 0.5189 (6) | 0.69241 (12) | 0.0624 (12) | |
H7A | 0.488024 | 0.471054 | 0.717189 | 0.075* | |
H7B | 0.624264 | 0.435314 | 0.685038 | 0.075* | |
C8 | 0.3961 (5) | 0.5342 (6) | 0.65535 (12) | 0.0674 (13) | |
H8A | 0.346810 | 0.416157 | 0.648371 | 0.081* | |
H8B | 0.304749 | 0.612321 | 0.663122 | 0.081* | |
C9 | 0.5459 (5) | 0.7883 (6) | 0.62835 (12) | 0.0652 (13) | |
H9A | 0.456601 | 0.870777 | 0.635373 | 0.078* | |
H9B | 0.595482 | 0.836462 | 0.603764 | 0.078* | |
C10 | 0.6842 (5) | 0.7725 (6) | 0.66592 (12) | 0.0645 (13) | |
H10A | 0.777785 | 0.697905 | 0.657962 | 0.077* | |
H10B | 0.730882 | 0.891256 | 0.673425 | 0.077* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0641 (18) | 0.097 (2) | 0.0424 (17) | 0.0242 (16) | 0.0060 (13) | −0.0135 (18) |
O2 | 0.0490 (17) | 0.099 (2) | 0.0463 (17) | 0.0219 (16) | 0.0089 (14) | 0.0024 (19) |
O3 | 0.0412 (15) | 0.077 (2) | 0.0425 (16) | 0.0074 (14) | 0.0000 (12) | 0.0002 (15) |
N3 | 0.047 (3) | 0.068 (4) | 0.037 (3) | −0.003 (3) | 0.006 (3) | −0.006 (3) |
O4 | 0.062 (3) | 0.104 (5) | 0.040 (3) | 0.015 (3) | 0.000 (2) | 0.005 (3) |
O5 | 0.059 (3) | 0.070 (4) | 0.053 (3) | −0.002 (3) | 0.015 (3) | −0.018 (3) |
N3A | 0.045 (5) | 0.072 (6) | 0.042 (6) | −0.001 (5) | 0.003 (5) | −0.006 (6) |
O4A | 0.053 (5) | 0.093 (8) | 0.045 (6) | 0.009 (6) | −0.008 (5) | −0.005 (6) |
O5A | 0.049 (5) | 0.078 (8) | 0.032 (6) | −0.002 (5) | 0.006 (5) | −0.021 (6) |
O6 | 0.0612 (18) | 0.096 (2) | 0.0589 (19) | 0.0335 (17) | 0.0024 (14) | −0.0098 (18) |
O7 | 0.074 (2) | 0.103 (3) | 0.0416 (17) | 0.0259 (17) | −0.0089 (13) | −0.0162 (18) |
N4 | 0.049 (2) | 0.059 (2) | 0.047 (2) | 0.0105 (18) | 0.0045 (16) | −0.004 (2) |
C11 | 0.041 (2) | 0.039 (2) | 0.037 (2) | 0.0007 (18) | 0.0059 (17) | 0.001 (2) |
C12 | 0.040 (2) | 0.044 (2) | 0.042 (2) | −0.0043 (19) | 0.0037 (17) | −0.001 (2) |
C13 | 0.048 (2) | 0.043 (3) | 0.030 (2) | −0.0043 (19) | 0.0082 (17) | −0.007 (2) |
C14 | 0.041 (2) | 0.036 (2) | 0.044 (2) | 0.0019 (18) | 0.0103 (17) | −0.002 (2) |
C15 | 0.038 (2) | 0.043 (2) | 0.037 (2) | 0.0041 (18) | 0.0025 (16) | −0.002 (2) |
C16 | 0.051 (2) | 0.040 (3) | 0.032 (2) | 0.0016 (19) | 0.0056 (17) | −0.0001 (19) |
C17 | 0.042 (2) | 0.056 (3) | 0.046 (3) | 0.006 (2) | 0.0065 (19) | 0.001 (2) |
N1 | 0.0485 (18) | 0.055 (2) | 0.0368 (18) | −0.0090 (17) | 0.0049 (14) | 0.0003 (18) |
N2 | 0.054 (2) | 0.103 (3) | 0.042 (2) | 0.022 (2) | −0.0011 (16) | −0.015 (2) |
C1 | 0.047 (3) | 0.067 (3) | 0.038 (3) | −0.006 (3) | 0.010 (2) | −0.006 (3) |
C2 | 0.061 (3) | 0.076 (4) | 0.050 (3) | −0.016 (3) | −0.004 (3) | 0.007 (3) |
C3 | 0.065 (3) | 0.080 (4) | 0.055 (3) | −0.019 (3) | −0.001 (3) | 0.008 (3) |
C4 | 0.069 (3) | 0.076 (4) | 0.038 (3) | −0.015 (3) | 0.003 (2) | −0.004 (3) |
C5 | 0.064 (3) | 0.089 (4) | 0.043 (3) | −0.020 (3) | 0.011 (3) | 0.009 (3) |
C6 | 0.057 (3) | 0.081 (3) | 0.038 (3) | −0.014 (3) | 0.008 (2) | 0.007 (3) |
C1A | 0.051 (4) | 0.075 (4) | 0.037 (4) | −0.011 (4) | 0.011 (4) | 0.003 (4) |
C2A | 0.058 (4) | 0.081 (5) | 0.049 (4) | −0.014 (4) | 0.010 (4) | −0.004 (4) |
C3A | 0.062 (4) | 0.084 (5) | 0.053 (4) | −0.013 (4) | 0.007 (4) | −0.001 (4) |
C4A | 0.064 (4) | 0.084 (5) | 0.043 (4) | −0.025 (4) | 0.011 (4) | 0.002 (4) |
C5A | 0.060 (4) | 0.080 (4) | 0.037 (4) | −0.023 (4) | 0.008 (4) | 0.009 (4) |
C6A | 0.057 (4) | 0.079 (4) | 0.041 (4) | −0.020 (4) | 0.005 (4) | 0.005 (4) |
C7 | 0.073 (3) | 0.067 (3) | 0.046 (3) | −0.008 (2) | −0.001 (2) | 0.003 (2) |
C8 | 0.069 (3) | 0.081 (4) | 0.051 (3) | −0.013 (2) | 0.002 (2) | −0.009 (3) |
C9 | 0.059 (3) | 0.086 (4) | 0.050 (3) | −0.001 (3) | 0.0037 (19) | 0.018 (3) |
C10 | 0.058 (3) | 0.089 (4) | 0.045 (2) | −0.013 (2) | 0.0022 (19) | 0.015 (3) |
O1—C17 | 1.211 (4) | C1—C6 | 1.3900 |
O2—C17 | 1.309 (4) | C2—C3 | 1.3900 |
O2—H2O | 0.841 (18) | C2—H2A | 0.9300 |
O3—C12 | 1.283 (4) | C3—C4 | 1.3900 |
N3—O5 | 1.236 (4) | C3—H3A | 0.9300 |
N3—O4 | 1.246 (5) | C4—C5 | 1.3900 |
N3—C13 | 1.467 (6) | C4—H4A | 0.9300 |
N3A—O5A | 1.237 (4) | C5—C6 | 1.3900 |
N3A—O4A | 1.246 (5) | C5—H5A | 0.9300 |
N3A—C13 | 1.401 (10) | C6—H6A | 0.9300 |
O6—N4 | 1.230 (3) | C1A—C2A | 1.3900 |
O7—N4 | 1.220 (3) | C1A—C6A | 1.3900 |
N4—C15 | 1.450 (4) | C2A—C3A | 1.3900 |
C11—C16 | 1.376 (4) | C2A—H2AA | 0.9300 |
C11—C12 | 1.428 (4) | C3A—C4A | 1.3900 |
C11—C17 | 1.505 (5) | C3A—H3AA | 0.9300 |
C12—C13 | 1.449 (5) | C4A—C5A | 1.3900 |
C13—C14 | 1.372 (4) | C4A—H4AA | 0.9300 |
C14—C15 | 1.370 (4) | C5A—C6A | 1.3900 |
C14—H14 | 0.9300 | C5A—H5AA | 0.9300 |
C15—C16 | 1.398 (4) | C6A—H6AA | 0.9300 |
C16—H16 | 0.9300 | C7—C8 | 1.501 (5) |
N1—C1A | 1.399 (9) | C7—H7A | 0.9700 |
N1—C1 | 1.448 (5) | C7—H7B | 0.9700 |
N1—C7 | 1.453 (5) | C8—H8A | 0.9700 |
N1—C10 | 1.465 (4) | C8—H8B | 0.9700 |
N2—C9 | 1.476 (5) | C9—C10 | 1.503 (5) |
N2—C8 | 1.482 (5) | C9—H9A | 0.9700 |
N2—H21 | 0.884 (18) | C9—H9B | 0.9700 |
N2—H22 | 0.874 (18) | C10—H10A | 0.9700 |
C1—C2 | 1.3900 | C10—H10B | 0.9700 |
C17—O2—H2O | 108 (3) | C4—C3—H3A | 120.0 |
O5—N3—O4 | 121.9 (4) | C5—C4—C3 | 120.0 |
O5—N3—C13 | 119.2 (5) | C5—C4—H4A | 120.0 |
O4—N3—C13 | 118.7 (5) | C3—C4—H4A | 120.0 |
O5A—N3A—O4A | 121.8 (6) | C6—C5—C4 | 120.0 |
O5A—N3A—C13 | 118.4 (8) | C6—C5—H5A | 120.0 |
O4A—N3A—C13 | 118.4 (8) | C4—C5—H5A | 120.0 |
O7—N4—O6 | 123.1 (3) | C5—C6—C1 | 120.0 |
O7—N4—C15 | 118.5 (3) | C5—C6—H6A | 120.0 |
O6—N4—C15 | 118.4 (3) | C1—C6—H6A | 120.0 |
C16—C11—C12 | 121.2 (3) | C2A—C1A—C6A | 120.0 |
C16—C11—C17 | 118.1 (3) | C2A—C1A—N1 | 116.8 (8) |
C12—C11—C17 | 120.7 (3) | C6A—C1A—N1 | 123.1 (8) |
O3—C12—C11 | 120.3 (3) | C1A—C2A—C3A | 120.0 |
O3—C12—C13 | 124.6 (3) | C1A—C2A—H2AA | 120.0 |
C11—C12—C13 | 115.1 (3) | C3A—C2A—H2AA | 120.0 |
C14—C13—N3A | 115.6 (4) | C4A—C3A—C2A | 120.0 |
C14—C13—C12 | 122.9 (3) | C4A—C3A—H3AA | 120.0 |
N3A—C13—C12 | 121.5 (4) | C2A—C3A—H3AA | 120.0 |
C14—C13—N3 | 117.0 (3) | C3A—C4A—C5A | 120.0 |
C12—C13—N3 | 120.1 (3) | C3A—C4A—H4AA | 120.0 |
C15—C14—C13 | 119.1 (3) | C5A—C4A—H4AA | 120.0 |
C15—C14—H14 | 120.5 | C4A—C5A—C6A | 120.0 |
C13—C14—H14 | 120.5 | C4A—C5A—H5AA | 120.0 |
C14—C15—C16 | 121.2 (3) | C6A—C5A—H5AA | 120.0 |
C14—C15—N4 | 119.1 (3) | C5A—C6A—C1A | 120.0 |
C16—C15—N4 | 119.7 (3) | C5A—C6A—H6AA | 120.0 |
C11—C16—C15 | 120.5 (3) | C1A—C6A—H6AA | 120.0 |
C11—C16—H16 | 119.8 | N1—C7—C8 | 111.2 (3) |
C15—C16—H16 | 119.8 | N1—C7—H7A | 109.4 |
O1—C17—O2 | 119.9 (3) | C8—C7—H7A | 109.4 |
O1—C17—C11 | 123.8 (3) | N1—C7—H7B | 109.4 |
O2—C17—C11 | 116.2 (3) | C8—C7—H7B | 109.4 |
C1A—N1—C7 | 120.5 (6) | H7A—C7—H7B | 108.0 |
C1—N1—C7 | 114.3 (3) | N2—C8—C7 | 109.5 (3) |
C1A—N1—C10 | 112.9 (5) | N2—C8—H8A | 109.8 |
C1—N1—C10 | 116.6 (3) | C7—C8—H8A | 109.8 |
C7—N1—C10 | 110.8 (3) | N2—C8—H8B | 109.8 |
C9—N2—C8 | 109.8 (3) | C7—C8—H8B | 109.8 |
C9—N2—H21 | 109 (3) | H8A—C8—H8B | 108.2 |
C8—N2—H21 | 110 (3) | N2—C9—C10 | 110.0 (4) |
C9—N2—H22 | 109 (3) | N2—C9—H9A | 109.7 |
C8—N2—H22 | 111 (3) | C10—C9—H9A | 109.7 |
H21—N2—H22 | 107 (4) | N2—C9—H9B | 109.7 |
C2—C1—C6 | 120.0 | C10—C9—H9B | 109.7 |
C2—C1—N1 | 119.9 (3) | H9A—C9—H9B | 108.2 |
C6—C1—N1 | 120.1 (3) | N1—C10—C9 | 111.2 (3) |
C3—C2—C1 | 120.0 | N1—C10—H10A | 109.4 |
C3—C2—H2A | 120.0 | C9—C10—H10A | 109.4 |
C1—C2—H2A | 120.0 | N1—C10—H10B | 109.4 |
C2—C3—C4 | 120.0 | C9—C10—H10B | 109.4 |
C2—C3—H3A | 120.0 | H10A—C10—H10B | 108.0 |
C16—C11—C12—O3 | 179.6 (3) | C7—N1—C1—C2 | 159.1 (3) |
C17—C11—C12—O3 | −0.4 (5) | C10—N1—C1—C2 | 27.7 (5) |
C16—C11—C12—C13 | −1.2 (5) | C7—N1—C1—C6 | −20.2 (4) |
C17—C11—C12—C13 | 178.8 (3) | C10—N1—C1—C6 | −151.6 (3) |
O5A—N3A—C13—C14 | 0.4 (19) | C6—C1—C2—C3 | 0.0 |
O4A—N3A—C13—C14 | −166.2 (13) | N1—C1—C2—C3 | −179.3 (4) |
O5A—N3A—C13—C12 | 178.7 (12) | C1—C2—C3—C4 | 0.0 |
O4A—N3A—C13—C12 | 12 (2) | C2—C3—C4—C5 | 0.0 |
O3—C12—C13—C14 | 179.0 (4) | C3—C4—C5—C6 | 0.0 |
C11—C12—C13—C14 | −0.2 (5) | C4—C5—C6—C1 | 0.0 |
O3—C12—C13—N3A | 0.8 (10) | C2—C1—C6—C5 | 0.0 |
C11—C12—C13—N3A | −178.4 (9) | N1—C1—C6—C5 | 179.3 (4) |
O3—C12—C13—N3 | 0.2 (6) | C7—N1—C1A—C2A | 176.7 (5) |
C11—C12—C13—N3 | −179.0 (5) | C10—N1—C1A—C2A | 42.6 (8) |
O5—N3—C13—C14 | −18.9 (9) | C7—N1—C1A—C6A | −4.1 (9) |
O4—N3—C13—C14 | 155.4 (6) | C10—N1—C1A—C6A | −138.2 (6) |
O5—N3—C13—C12 | 160.0 (6) | C6A—C1A—C2A—C3A | 0.0 |
O4—N3—C13—C12 | −25.7 (9) | N1—C1A—C2A—C3A | 179.2 (8) |
N3A—C13—C14—C15 | 179.4 (9) | C1A—C2A—C3A—C4A | 0.0 |
C12—C13—C14—C15 | 1.1 (5) | C2A—C3A—C4A—C5A | 0.0 |
N3—C13—C14—C15 | 179.9 (5) | C3A—C4A—C5A—C6A | 0.0 |
C13—C14—C15—C16 | −0.6 (6) | C4A—C5A—C6A—C1A | 0.0 |
C13—C14—C15—N4 | 179.3 (3) | C2A—C1A—C6A—C5A | 0.0 |
O7—N4—C15—C14 | −174.3 (4) | N1—C1A—C6A—C5A | −179.2 (9) |
O6—N4—C15—C14 | 6.1 (5) | C1A—N1—C7—C8 | 168.3 (6) |
O7—N4—C15—C16 | 5.6 (5) | C1—N1—C7—C8 | 168.9 (3) |
O6—N4—C15—C16 | −174.0 (3) | C10—N1—C7—C8 | −56.9 (4) |
C12—C11—C16—C15 | 1.7 (5) | C9—N2—C8—C7 | −58.8 (4) |
C17—C11—C16—C15 | −178.3 (3) | N1—C7—C8—N2 | 58.3 (5) |
C14—C15—C16—C11 | −0.8 (6) | C8—N2—C9—C10 | 58.3 (4) |
N4—C15—C16—C11 | 179.3 (3) | C1A—N1—C10—C9 | −165.4 (6) |
C16—C11—C17—O1 | −0.9 (6) | C1—N1—C10—C9 | −170.9 (4) |
C12—C11—C17—O1 | 179.1 (4) | C7—N1—C10—C9 | 56.1 (5) |
C16—C11—C17—O2 | −179.4 (3) | N2—C9—C10—N1 | −57.0 (5) |
C12—C11—C17—O2 | 0.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O3 | 0.84 (2) | 1.69 (2) | 2.487 (3) | 156 (4) |
N2—H21···O3 | 0.88 (2) | 2.03 (2) | 2.873 (4) | 159 (3) |
N2—H21···O4 | 0.88 (2) | 2.37 (3) | 2.950 (6) | 123 (3) |
N2—H21···O4A | 0.88 (2) | 2.40 (4) | 2.966 (10) | 122 (3) |
N2—H22···O1i | 0.87 (2) | 2.10 (2) | 2.947 (4) | 164 (4) |
N2—H22···O2i | 0.87 (2) | 2.62 (3) | 3.270 (4) | 132 (3) |
C8—H8A···O7ii | 0.97 | 2.36 | 3.134 (5) | 137 |
C8—H8B···O4 | 0.97 | 2.44 | 3.000 (6) | 116 |
C9—H9A···O4A | 0.97 | 2.60 | 3.166 (8) | 118 |
C9—H9B···O5iii | 0.97 | 2.58 | 3.311 (8) | 132 |
C9—H9B···O5Aiii | 0.97 | 2.29 | 3.040 (13) | 133 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x+1, y, z. |
C10H15N2+·C7H3N2O6− | Z = 2 |
Mr = 374.35 | F(000) = 392 |
Triclinic, P1 | Dx = 1.379 Mg m−3 |
a = 5.707 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.505 (3) Å | Cell parameters from 838 reflections |
c = 13.116 (3) Å | θ = 3.1–28.1° |
α = 97.41 (2)° | µ = 0.11 mm−1 |
β = 93.28 (2)° | T = 293 K |
γ = 102.82 (2)° | Needle, yellow |
V = 901.5 (4) Å3 | 0.48 × 0.08 × 0.04 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 2647 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.087 |
Rotation method data acquisition using ω scans. | θmax = 28.1°, θmin = 3.2° |
Absorption correction: multi-scan (CrysalisRED; Oxford Diffraction, 2007) | h = −7→7 |
Tmin = 0.647, Tmax = 1.000 | k = −16→15 |
7800 measured reflections | l = −16→17 |
7800 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.147 | Hydrogen site location: mixed |
wR(F2) = 0.297 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0451P)2 + 3.195P] where P = (Fo2 + 2Fc2)/3 |
7800 reflections | (Δ/σ)max < 0.001 |
251 parameters | Δρmax = 0.28 e Å−3 |
2 restraints | Δρmin = −0.30 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. |
Refinement. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.122 (2) | 0.6276 (12) | 0.8824 (9) | 0.051 (4) | |
C2 | 1.091 (2) | 0.7342 (12) | 0.9003 (10) | 0.062 (4) | |
H2 | 0.954536 | 0.750440 | 0.869306 | 0.074* | |
C3 | 1.256 (3) | 0.8180 (14) | 0.9629 (11) | 0.089 (5) | |
H3 | 1.229141 | 0.889054 | 0.974939 | 0.107* | |
C4 | 1.462 (3) | 0.7954 (17) | 1.0076 (11) | 0.090 (6) | |
H4 | 1.577146 | 0.850571 | 1.049126 | 0.108* | |
C5 | 1.491 (3) | 0.6892 (17) | 0.9888 (11) | 0.084 (5) | |
H5 | 1.626416 | 0.672664 | 1.019709 | 0.101* | |
C6 | 1.329 (2) | 0.6064 (13) | 0.9265 (10) | 0.066 (4) | |
H6 | 1.358012 | 0.535803 | 0.913969 | 0.079* | |
C7 | 0.956 (2) | 0.4298 (10) | 0.8199 (9) | 0.055 (4) | |
H7A | 0.973803 | 0.416389 | 0.890828 | 0.066* | |
H7B | 1.095257 | 0.415218 | 0.786306 | 0.066* | |
C8 | 0.729 (2) | 0.3532 (10) | 0.7652 (9) | 0.056 (4) | |
H8A | 0.738219 | 0.276750 | 0.765936 | 0.067* | |
H8B | 0.590703 | 0.365439 | 0.800390 | 0.067* | |
C9 | 0.700 (2) | 0.4918 (11) | 0.6524 (9) | 0.063 (4) | |
H9A | 0.557086 | 0.508210 | 0.681256 | 0.076* | |
H9B | 0.694830 | 0.504487 | 0.580979 | 0.076* | |
C10 | 0.920 (2) | 0.5662 (10) | 0.7114 (9) | 0.055 (4) | |
H10A | 1.061481 | 0.555114 | 0.677531 | 0.066* | |
H10B | 0.911569 | 0.642726 | 0.711107 | 0.066* | |
C11 | −0.018 (2) | 0.1731 (10) | 0.4335 (9) | 0.041 (3) | |
C12 | 0.037 (2) | 0.0713 (10) | 0.4039 (8) | 0.046 (3) | |
H12 | 0.169558 | 0.053646 | 0.436202 | 0.055* | |
C13 | −0.106 (2) | −0.0027 (11) | 0.3270 (10) | 0.046 (3) | |
C14 | −0.307 (2) | 0.0161 (10) | 0.2780 (9) | 0.054 (4) | |
H14 | −0.406231 | −0.036584 | 0.227934 | 0.065* | |
C15 | −0.353 (2) | 0.1182 (12) | 0.3079 (10) | 0.052 (4) | |
C16 | −0.219 (2) | 0.1950 (10) | 0.3858 (9) | 0.047 (3) | |
H16 | −0.264440 | 0.261054 | 0.406096 | 0.056* | |
C17 | 0.144 (3) | 0.2554 (12) | 0.5164 (10) | 0.056 (4) | |
N1 | 0.9454 (16) | 0.5450 (8) | 0.8180 (7) | 0.046 (3) | |
N2 | 0.7030 (19) | 0.3750 (10) | 0.6575 (9) | 0.060 (3) | |
H21 | 0.585 (14) | 0.323 (8) | 0.625 (8) | 0.072* | |
H22 | 0.817 (15) | 0.354 (9) | 0.624 (8) | 0.072* | |
N3 | −0.040 (2) | −0.1092 (10) | 0.2942 (9) | 0.063 (3) | |
N4 | −0.560 (2) | 0.1460 (14) | 0.2536 (10) | 0.075 (4) | |
O1 | 0.0892 (15) | 0.3455 (7) | 0.5441 (7) | 0.069 (3) | |
O2 | 0.3327 (15) | 0.2290 (7) | 0.5475 (7) | 0.071 (3) | |
O3 | 0.1442 (18) | −0.1237 (7) | 0.3359 (7) | 0.076 (3) | |
O4 | −0.1697 (18) | −0.1757 (8) | 0.2251 (7) | 0.099 (4) | |
O5 | −0.5922 (18) | 0.2403 (11) | 0.2752 (8) | 0.094 (4) | |
O6 | −0.6948 (17) | 0.0739 (10) | 0.1901 (8) | 0.090 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.045 (9) | 0.059 (11) | 0.043 (8) | 0.005 (8) | −0.004 (7) | −0.001 (7) |
C2 | 0.068 (10) | 0.053 (11) | 0.064 (10) | 0.012 (9) | 0.006 (8) | 0.005 (8) |
C3 | 0.102 (14) | 0.073 (13) | 0.072 (11) | −0.006 (12) | 0.001 (10) | −0.014 (9) |
C4 | 0.074 (13) | 0.108 (17) | 0.057 (10) | −0.029 (12) | −0.011 (9) | −0.012 (11) |
C5 | 0.082 (13) | 0.111 (16) | 0.055 (10) | 0.012 (13) | 0.004 (9) | 0.017 (10) |
C6 | 0.054 (10) | 0.080 (13) | 0.053 (9) | 0.002 (9) | −0.004 (8) | −0.001 (8) |
C7 | 0.058 (9) | 0.061 (11) | 0.052 (8) | 0.023 (8) | 0.007 (7) | 0.012 (7) |
C8 | 0.064 (10) | 0.039 (9) | 0.062 (9) | 0.008 (7) | 0.011 (8) | 0.000 (7) |
C9 | 0.069 (10) | 0.055 (11) | 0.062 (9) | 0.011 (8) | −0.010 (8) | 0.006 (7) |
C10 | 0.055 (9) | 0.047 (9) | 0.058 (9) | 0.013 (7) | −0.005 (7) | −0.005 (7) |
C11 | 0.035 (7) | 0.026 (8) | 0.058 (8) | 0.002 (6) | 0.010 (7) | 0.006 (6) |
C12 | 0.048 (8) | 0.048 (9) | 0.036 (8) | 0.000 (7) | −0.004 (7) | 0.013 (6) |
C13 | 0.035 (8) | 0.055 (10) | 0.050 (8) | 0.015 (7) | −0.001 (7) | 0.010 (7) |
C14 | 0.050 (9) | 0.038 (10) | 0.061 (9) | −0.012 (8) | 0.004 (8) | 0.000 (7) |
C15 | 0.039 (9) | 0.067 (11) | 0.047 (8) | 0.001 (8) | −0.006 (7) | 0.018 (8) |
C16 | 0.038 (8) | 0.042 (9) | 0.068 (9) | 0.019 (7) | 0.016 (7) | 0.010 (7) |
C17 | 0.058 (10) | 0.050 (11) | 0.052 (9) | 0.004 (8) | 0.016 (8) | −0.008 (8) |
N1 | 0.048 (7) | 0.045 (8) | 0.045 (7) | 0.015 (6) | 0.001 (6) | 0.004 (5) |
N2 | 0.050 (8) | 0.058 (10) | 0.061 (9) | 0.005 (6) | 0.005 (6) | −0.015 (6) |
N3 | 0.078 (10) | 0.053 (9) | 0.062 (8) | 0.026 (8) | 0.003 (7) | −0.002 (7) |
N4 | 0.055 (9) | 0.111 (14) | 0.069 (9) | 0.028 (10) | 0.012 (8) | 0.028 (9) |
O1 | 0.070 (7) | 0.048 (7) | 0.083 (7) | 0.008 (5) | 0.019 (5) | −0.009 (5) |
O2 | 0.051 (6) | 0.063 (7) | 0.087 (7) | 0.012 (5) | −0.013 (6) | −0.021 (5) |
O3 | 0.079 (8) | 0.056 (7) | 0.096 (8) | 0.028 (6) | 0.000 (6) | 0.001 (5) |
O4 | 0.136 (9) | 0.061 (8) | 0.083 (7) | 0.022 (7) | −0.022 (7) | −0.032 (6) |
O5 | 0.077 (8) | 0.130 (12) | 0.100 (9) | 0.060 (8) | 0.019 (6) | 0.042 (8) |
O6 | 0.056 (7) | 0.132 (11) | 0.080 (7) | 0.017 (7) | −0.009 (6) | 0.029 (7) |
C1—C6 | 1.377 (15) | C10—N1 | 1.461 (13) |
C1—C2 | 1.377 (16) | C10—H10A | 0.9700 |
C1—N1 | 1.418 (14) | C10—H10B | 0.9700 |
C2—C3 | 1.384 (17) | C11—C16 | 1.374 (14) |
C2—H2 | 0.9300 | C11—C12 | 1.390 (15) |
C3—C4 | 1.385 (19) | C11—C17 | 1.507 (15) |
C3—H3 | 0.9300 | C12—C13 | 1.367 (14) |
C4—C5 | 1.37 (2) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—C14 | 1.363 (14) |
C5—C6 | 1.365 (18) | C13—N3 | 1.481 (15) |
C5—H5 | 0.9300 | C14—C15 | 1.373 (16) |
C6—H6 | 0.9300 | C14—H14 | 0.9300 |
C7—N1 | 1.459 (13) | C15—C16 | 1.372 (14) |
C7—C8 | 1.507 (14) | C15—N4 | 1.473 (15) |
C7—H7A | 0.9700 | C16—H16 | 0.9300 |
C7—H7B | 0.9700 | C17—O1 | 1.251 (14) |
C8—N2 | 1.479 (15) | C17—O2 | 1.256 (14) |
C8—H8A | 0.9700 | N2—H21 | 0.87 (3) |
C8—H8B | 0.9700 | N2—H22 | 0.87 (3) |
C9—N2 | 1.475 (16) | N3—O3 | 1.219 (11) |
C9—C10 | 1.492 (14) | N3—O4 | 1.230 (12) |
C9—H9A | 0.9700 | N4—O5 | 1.233 (15) |
C9—H9B | 0.9700 | N4—O6 | 1.234 (14) |
C6—C1—C2 | 118.0 (13) | N1—C10—H10B | 109.2 |
C6—C1—N1 | 122.7 (14) | C9—C10—H10B | 109.2 |
C2—C1—N1 | 119.3 (13) | H10A—C10—H10B | 107.9 |
C1—C2—C3 | 121.9 (15) | C16—C11—C12 | 118.5 (11) |
C1—C2—H2 | 119.1 | C16—C11—C17 | 122.3 (12) |
C3—C2—H2 | 119.1 | C12—C11—C17 | 119.2 (12) |
C2—C3—C4 | 119.5 (17) | C13—C12—C11 | 119.5 (11) |
C2—C3—H3 | 120.2 | C13—C12—H12 | 120.2 |
C4—C3—H3 | 120.2 | C11—C12—H12 | 120.2 |
C5—C4—C3 | 117.8 (16) | C14—C13—C12 | 123.6 (13) |
C5—C4—H4 | 121.1 | C14—C13—N3 | 117.6 (12) |
C3—C4—H4 | 121.1 | C12—C13—N3 | 118.7 (12) |
C6—C5—C4 | 122.9 (17) | C13—C14—C15 | 115.2 (12) |
C6—C5—H5 | 118.5 | C13—C14—H14 | 122.4 |
C4—C5—H5 | 118.5 | C15—C14—H14 | 122.4 |
C5—C6—C1 | 119.8 (15) | C16—C15—C14 | 123.7 (13) |
C5—C6—H6 | 120.1 | C16—C15—N4 | 118.4 (14) |
C1—C6—H6 | 120.1 | C14—C15—N4 | 117.9 (13) |
N1—C7—C8 | 110.1 (10) | C15—C16—C11 | 119.2 (12) |
N1—C7—H7A | 109.6 | C15—C16—H16 | 120.4 |
C8—C7—H7A | 109.6 | C11—C16—H16 | 120.4 |
N1—C7—H7B | 109.6 | O1—C17—O2 | 125.5 (13) |
C8—C7—H7B | 109.6 | O1—C17—C11 | 118.5 (14) |
H7A—C7—H7B | 108.2 | O2—C17—C11 | 115.8 (13) |
N2—C8—C7 | 109.2 (10) | C1—N1—C7 | 117.2 (11) |
N2—C8—H8A | 109.8 | C1—N1—C10 | 113.8 (10) |
C7—C8—H8A | 109.8 | C7—N1—C10 | 110.0 (9) |
N2—C8—H8B | 109.8 | C9—N2—C8 | 111.8 (9) |
C7—C8—H8B | 109.8 | C9—N2—H21 | 119 (9) |
H8A—C8—H8B | 108.3 | C8—N2—H21 | 107 (8) |
N2—C9—C10 | 109.9 (10) | C9—N2—H22 | 112 (8) |
N2—C9—H9A | 109.7 | C8—N2—H22 | 109 (8) |
C10—C9—H9A | 109.7 | H21—N2—H22 | 96 (10) |
N2—C9—H9B | 109.7 | O3—N3—O4 | 124.1 (13) |
C10—C9—H9B | 109.7 | O3—N3—C13 | 117.2 (12) |
H9A—C9—H9B | 108.2 | O4—N3—C13 | 118.6 (13) |
N1—C10—C9 | 111.9 (11) | O5—N4—O6 | 123.1 (15) |
N1—C10—H10A | 109.2 | O5—N4—C15 | 118.1 (15) |
C9—C10—H10A | 109.2 | O6—N4—C15 | 118.8 (15) |
C6—C1—C2—C3 | −2 (2) | C16—C11—C17—O1 | 1.7 (18) |
N1—C1—C2—C3 | 179.6 (12) | C12—C11—C17—O1 | −178.2 (12) |
C1—C2—C3—C4 | 1 (2) | C16—C11—C17—O2 | −174.2 (12) |
C2—C3—C4—C5 | −1 (2) | C12—C11—C17—O2 | 5.8 (17) |
C3—C4—C5—C6 | 1 (3) | C6—C1—N1—C7 | 15.3 (16) |
C4—C5—C6—C1 | −2 (2) | C2—C1—N1—C7 | −166.4 (11) |
C2—C1—C6—C5 | 2.3 (19) | C6—C1—N1—C10 | −115.1 (13) |
N1—C1—C6—C5 | −179.3 (12) | C2—C1—N1—C10 | 63.3 (15) |
N1—C7—C8—N2 | 58.8 (12) | C8—C7—N1—C1 | 168.3 (10) |
N2—C9—C10—N1 | −55.4 (13) | C8—C7—N1—C10 | −59.6 (12) |
C16—C11—C12—C13 | 1.7 (17) | C9—C10—N1—C1 | −167.8 (10) |
C17—C11—C12—C13 | −178.4 (11) | C9—C10—N1—C7 | 58.3 (13) |
C11—C12—C13—C14 | −1.8 (18) | C10—C9—N2—C8 | 55.0 (13) |
C11—C12—C13—N3 | 178.0 (11) | C7—C8—N2—C9 | −56.9 (13) |
C12—C13—C14—C15 | 2.8 (18) | C14—C13—N3—O3 | 177.5 (12) |
N3—C13—C14—C15 | −177.0 (12) | C12—C13—N3—O3 | −2.3 (17) |
C13—C14—C15—C16 | −4.0 (19) | C14—C13—N3—O4 | −0.4 (18) |
C13—C14—C15—N4 | 176.5 (11) | C12—C13—N3—O4 | 179.8 (12) |
C14—C15—C16—C11 | 4.2 (19) | C16—C15—N4—O5 | 5.4 (18) |
N4—C15—C16—C11 | −176.4 (11) | C14—C15—N4—O5 | −175.0 (14) |
C12—C11—C16—C15 | −2.8 (16) | C16—C15—N4—O6 | −173.4 (13) |
C17—C11—C16—C15 | 177.3 (11) | C14—C15—N4—O6 | 6.1 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O3i | 0.97 | 2.43 | 3.250 (14) | 142 |
C10—H10B···O5ii | 0.97 | 2.58 | 3.366 (16) | 138 |
N2—H21···O2 | 0.87 (3) | 1.81 (4) | 2.672 (13) | 172 (13) |
N2—H22···O1iii | 0.87 (3) | 1.94 (4) | 2.792 (13) | 166 (12) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1; (iii) x+1, y, z. |
C10H15N2+·C6H2N3O7− | F(000) = 816 |
Mr = 391.34 | Dx = 1.484 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.517 (1) Å | Cell parameters from 2640 reflections |
b = 6.825 (1) Å | θ = 2.6–27.9° |
c = 30.265 (4) Å | µ = 0.12 mm−1 |
β = 95.33 (1)° | T = 293 K |
V = 1751.7 (4) Å3 | Prism, yellow |
Z = 4 | 0.50 × 0.36 × 0.20 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 2389 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.076 |
ω and φ scans | θmax = 28.0°, θmin = 2.6° |
Absorption correction: multi-scan (CrysalisRED; Oxford Diffraction, 2007) | h = −10→10 |
Tmin = 0.835, Tmax = 1.000 | k = −8→4 |
12427 measured reflections | l = −34→38 |
3893 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.149 | w = 1/[σ2(Fo2) + (0.0504P)2 + 0.8725P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3893 reflections | Δρmax = 0.26 e Å−3 |
260 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: dual | Extinction coefficient: 0.0131 (17) |
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 | ||
C1 | 0.7177 (3) | 0.4179 (4) | 0.26101 (7) | 0.0433 (6) | |
C2 | 0.7900 (3) | 0.5991 (4) | 0.25921 (9) | 0.0570 (7) | |
H2 | 0.780507 | 0.690261 | 0.281649 | 0.068* | |
C3 | 0.8768 (3) | 0.6449 (5) | 0.22386 (10) | 0.0688 (9) | |
H3 | 0.923005 | 0.768012 | 0.222678 | 0.083* | |
C4 | 0.8954 (3) | 0.5133 (6) | 0.19100 (10) | 0.0694 (9) | |
H4 | 0.953581 | 0.545868 | 0.167535 | 0.083* | |
C5 | 0.8277 (3) | 0.3334 (5) | 0.19292 (9) | 0.0669 (8) | |
H5 | 0.841487 | 0.241929 | 0.170835 | 0.080* | |
C6 | 0.7388 (3) | 0.2847 (4) | 0.22725 (8) | 0.0556 (7) | |
H6 | 0.692475 | 0.161451 | 0.227796 | 0.067* | |
C7 | 0.6520 (3) | 0.1721 (4) | 0.31432 (9) | 0.0593 (7) | |
H7A | 0.753277 | 0.171429 | 0.331875 | 0.071* | |
H7B | 0.656412 | 0.077286 | 0.290590 | 0.071* | |
C8 | 0.5257 (3) | 0.1140 (4) | 0.34299 (9) | 0.0608 (8) | |
H8A | 0.425199 | 0.106259 | 0.325154 | 0.073* | |
H8B | 0.549272 | −0.014205 | 0.355756 | 0.073* | |
C9 | 0.4869 (3) | 0.4552 (5) | 0.35981 (10) | 0.0659 (8) | |
H9A | 0.485333 | 0.550341 | 0.383577 | 0.079* | |
H9B | 0.384923 | 0.457927 | 0.342652 | 0.079* | |
C10 | 0.6136 (3) | 0.5090 (4) | 0.33044 (9) | 0.0574 (7) | |
H10A | 0.591245 | 0.637189 | 0.317528 | 0.069* | |
H10B | 0.714497 | 0.515872 | 0.348122 | 0.069* | |
C11 | −0.1176 (3) | 0.2795 (3) | 0.46054 (8) | 0.0401 (5) | |
C12 | 0.0517 (3) | 0.2586 (3) | 0.46416 (7) | 0.0378 (5) | |
C13 | 0.1453 (3) | 0.2289 (3) | 0.50261 (8) | 0.0403 (5) | |
H13 | 0.253635 | 0.212835 | 0.502247 | 0.048* | |
C14 | 0.0762 (3) | 0.2232 (3) | 0.54215 (7) | 0.0393 (5) | |
C15 | −0.0855 (3) | 0.2447 (3) | 0.54264 (8) | 0.0406 (6) | |
H15 | −0.131175 | 0.242523 | 0.569377 | 0.049* | |
C16 | −0.1766 (3) | 0.2689 (3) | 0.50371 (8) | 0.0395 (5) | |
N1 | 0.6227 (2) | 0.3663 (3) | 0.29532 (6) | 0.0426 (5) | |
N2 | 0.5157 (3) | 0.2589 (4) | 0.37874 (8) | 0.0600 (7) | |
H21 | 0.446 (4) | 0.227 (4) | 0.3950 (10) | 0.072* | |
H22 | 0.614 (4) | 0.265 (4) | 0.3984 (10) | 0.072* | |
N3 | 0.1308 (3) | 0.2645 (3) | 0.42356 (7) | 0.0491 (5) | |
N4 | 0.1728 (3) | 0.1928 (3) | 0.58323 (7) | 0.0551 (6) | |
N5 | −0.3455 (3) | 0.2877 (4) | 0.50670 (8) | 0.0561 (6) | |
O1 | −0.1980 (2) | 0.3022 (3) | 0.42443 (6) | 0.0645 (6) | |
O2 | 0.2413 (2) | 0.1487 (3) | 0.42128 (6) | 0.0648 (6) | |
O3 | 0.0884 (3) | 0.3800 (3) | 0.39444 (6) | 0.0705 (6) | |
O4 | 0.3160 (3) | 0.1892 (4) | 0.58218 (7) | 0.0770 (7) | |
O5 | 0.1098 (3) | 0.1737 (3) | 0.61764 (6) | 0.0763 (7) | |
O6 | −0.3873 (3) | 0.3692 (4) | 0.53943 (8) | 0.0982 (9) | |
O7 | −0.4365 (2) | 0.2218 (4) | 0.47735 (8) | 0.0836 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0335 (12) | 0.0615 (16) | 0.0346 (12) | 0.0028 (11) | 0.0017 (10) | 0.0009 (11) |
C2 | 0.0524 (16) | 0.0688 (19) | 0.0505 (16) | −0.0122 (14) | 0.0088 (13) | −0.0012 (14) |
C3 | 0.0500 (17) | 0.092 (2) | 0.0650 (19) | −0.0185 (15) | 0.0072 (14) | 0.0147 (18) |
C4 | 0.0457 (16) | 0.117 (3) | 0.0474 (17) | 0.0019 (17) | 0.0123 (13) | 0.0096 (18) |
C5 | 0.0599 (18) | 0.098 (3) | 0.0439 (16) | 0.0138 (17) | 0.0087 (13) | −0.0068 (16) |
C6 | 0.0541 (16) | 0.0721 (19) | 0.0410 (14) | 0.0017 (13) | 0.0066 (12) | −0.0043 (14) |
C7 | 0.0650 (18) | 0.0619 (18) | 0.0530 (16) | 0.0100 (14) | 0.0154 (13) | 0.0096 (14) |
C8 | 0.0599 (17) | 0.0671 (19) | 0.0548 (17) | −0.0037 (14) | 0.0028 (13) | 0.0169 (15) |
C9 | 0.0609 (18) | 0.079 (2) | 0.0621 (18) | −0.0024 (15) | 0.0273 (15) | −0.0079 (16) |
C10 | 0.0589 (17) | 0.0638 (18) | 0.0524 (16) | −0.0096 (13) | 0.0198 (13) | −0.0097 (14) |
C11 | 0.0419 (13) | 0.0392 (13) | 0.0393 (13) | −0.0045 (10) | 0.0040 (10) | −0.0039 (10) |
C12 | 0.0437 (13) | 0.0337 (12) | 0.0375 (12) | −0.0070 (10) | 0.0114 (10) | −0.0035 (10) |
C13 | 0.0387 (12) | 0.0326 (12) | 0.0501 (14) | −0.0034 (10) | 0.0059 (10) | −0.0017 (11) |
C14 | 0.0481 (14) | 0.0324 (12) | 0.0369 (13) | −0.0025 (10) | 0.0012 (10) | 0.0030 (10) |
C15 | 0.0519 (14) | 0.0337 (12) | 0.0377 (13) | −0.0024 (10) | 0.0119 (11) | −0.0022 (10) |
C16 | 0.0401 (12) | 0.0337 (12) | 0.0458 (14) | −0.0007 (10) | 0.0094 (10) | −0.0039 (10) |
N1 | 0.0411 (11) | 0.0501 (12) | 0.0374 (10) | −0.0014 (9) | 0.0082 (8) | −0.0003 (9) |
N2 | 0.0369 (12) | 0.102 (2) | 0.0419 (13) | −0.0107 (12) | 0.0070 (10) | 0.0129 (13) |
N3 | 0.0497 (13) | 0.0538 (14) | 0.0456 (13) | −0.0141 (11) | 0.0136 (10) | −0.0062 (11) |
N4 | 0.0633 (15) | 0.0533 (14) | 0.0476 (13) | −0.0044 (11) | −0.0016 (11) | 0.0095 (11) |
N5 | 0.0466 (13) | 0.0710 (16) | 0.0522 (14) | 0.0037 (11) | 0.0115 (11) | −0.0040 (12) |
O1 | 0.0492 (11) | 0.0992 (16) | 0.0439 (11) | −0.0128 (10) | −0.0022 (8) | 0.0049 (10) |
O2 | 0.0475 (11) | 0.0813 (15) | 0.0695 (13) | −0.0011 (10) | 0.0256 (9) | −0.0093 (11) |
O3 | 0.0900 (16) | 0.0759 (15) | 0.0487 (11) | −0.0030 (11) | 0.0225 (11) | 0.0104 (11) |
O4 | 0.0533 (13) | 0.1053 (18) | 0.0699 (14) | 0.0007 (11) | −0.0073 (10) | 0.0184 (12) |
O5 | 0.0829 (15) | 0.1026 (18) | 0.0430 (11) | −0.0078 (12) | 0.0044 (10) | 0.0215 (11) |
O6 | 0.0651 (15) | 0.161 (3) | 0.0722 (15) | 0.0199 (15) | 0.0266 (12) | −0.0310 (16) |
O7 | 0.0460 (12) | 0.131 (2) | 0.0738 (15) | −0.0125 (12) | 0.0081 (11) | −0.0182 (14) |
C1—C2 | 1.385 (4) | C10—N1 | 1.449 (3) |
C1—C6 | 1.392 (3) | C10—H10A | 0.9700 |
C1—N1 | 1.419 (3) | C10—H10B | 0.9700 |
C2—C3 | 1.391 (4) | C11—O1 | 1.244 (3) |
C2—H2 | 0.9300 | C11—C12 | 1.443 (3) |
C3—C4 | 1.361 (4) | C11—C16 | 1.445 (3) |
C3—H3 | 0.9300 | C12—C13 | 1.363 (3) |
C4—C5 | 1.359 (4) | C12—N3 | 1.456 (3) |
C4—H4 | 0.9300 | C13—C14 | 1.382 (3) |
C5—C6 | 1.382 (4) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—C15 | 1.386 (3) |
C6—H6 | 0.9300 | C14—N4 | 1.441 (3) |
C7—N1 | 1.457 (3) | C15—C16 | 1.360 (3) |
C7—C8 | 1.497 (4) | C15—H15 | 0.9300 |
C7—H7A | 0.9700 | C16—N5 | 1.455 (3) |
C7—H7B | 0.9700 | N2—H21 | 0.83 (3) |
C8—N2 | 1.474 (4) | N2—H22 | 0.98 (3) |
C8—H8A | 0.9700 | N3—O3 | 1.212 (3) |
C8—H8B | 0.9700 | N3—O2 | 1.236 (3) |
C9—N2 | 1.469 (4) | N4—O5 | 1.222 (3) |
C9—C10 | 1.506 (3) | N4—O4 | 1.223 (3) |
C9—H9A | 0.9700 | N5—O7 | 1.210 (3) |
C9—H9B | 0.9700 | N5—O6 | 1.218 (3) |
C2—C1—C6 | 117.8 (2) | N1—C10—H10B | 109.4 |
C2—C1—N1 | 122.4 (2) | C9—C10—H10B | 109.4 |
C6—C1—N1 | 119.8 (2) | H10A—C10—H10B | 108.0 |
C1—C2—C3 | 120.1 (3) | O1—C11—C12 | 122.9 (2) |
C1—C2—H2 | 120.0 | O1—C11—C16 | 126.2 (2) |
C3—C2—H2 | 120.0 | C12—C11—C16 | 110.8 (2) |
C4—C3—C2 | 121.3 (3) | C13—C12—C11 | 125.5 (2) |
C4—C3—H3 | 119.3 | C13—C12—N3 | 116.4 (2) |
C2—C3—H3 | 119.3 | C11—C12—N3 | 118.1 (2) |
C5—C4—C3 | 119.1 (3) | C12—C13—C14 | 118.7 (2) |
C5—C4—H4 | 120.4 | C12—C13—H13 | 120.6 |
C3—C4—H4 | 120.4 | C14—C13—H13 | 120.6 |
C4—C5—C6 | 120.9 (3) | C13—C14—C15 | 120.6 (2) |
C4—C5—H5 | 119.6 | C13—C14—N4 | 119.7 (2) |
C6—C5—H5 | 119.6 | C15—C14—N4 | 119.6 (2) |
C5—C6—C1 | 120.8 (3) | C16—C15—C14 | 119.4 (2) |
C5—C6—H6 | 119.6 | C16—C15—H15 | 120.3 |
C1—C6—H6 | 119.6 | C14—C15—H15 | 120.3 |
N1—C7—C8 | 111.3 (2) | C15—C16—C11 | 124.8 (2) |
N1—C7—H7A | 109.4 | C15—C16—N5 | 116.4 (2) |
C8—C7—H7A | 109.4 | C11—C16—N5 | 118.7 (2) |
N1—C7—H7B | 109.4 | C1—N1—C10 | 116.3 (2) |
C8—C7—H7B | 109.4 | C1—N1—C7 | 115.2 (2) |
H7A—C7—H7B | 108.0 | C10—N1—C7 | 109.9 (2) |
N2—C8—C7 | 110.0 (2) | C9—N2—C8 | 110.2 (2) |
N2—C8—H8A | 109.7 | C9—N2—H21 | 112 (2) |
C7—C8—H8A | 109.7 | C8—N2—H21 | 111 (2) |
N2—C8—H8B | 109.7 | C9—N2—H22 | 107.5 (17) |
C7—C8—H8B | 109.7 | C8—N2—H22 | 111.7 (17) |
H8A—C8—H8B | 108.2 | H21—N2—H22 | 105 (3) |
N2—C9—C10 | 110.5 (2) | O3—N3—O2 | 123.5 (2) |
N2—C9—H9A | 109.6 | O3—N3—C12 | 120.1 (2) |
C10—C9—H9A | 109.6 | O2—N3—C12 | 116.3 (2) |
N2—C9—H9B | 109.6 | O5—N4—O4 | 122.5 (2) |
C10—C9—H9B | 109.6 | O5—N4—C14 | 119.4 (2) |
H9A—C9—H9B | 108.1 | O4—N4—C14 | 118.1 (2) |
N1—C10—C9 | 111.0 (2) | O7—N5—O6 | 123.4 (2) |
N1—C10—H10A | 109.4 | O7—N5—C16 | 119.4 (2) |
C9—C10—H10A | 109.4 | O6—N5—C16 | 117.1 (2) |
C6—C1—C2—C3 | 1.7 (4) | O1—C11—C16—N5 | −0.6 (4) |
N1—C1—C2—C3 | −177.4 (2) | C12—C11—C16—N5 | 179.8 (2) |
C1—C2—C3—C4 | −1.3 (4) | C2—C1—N1—C10 | −4.1 (3) |
C2—C3—C4—C5 | −0.1 (5) | C6—C1—N1—C10 | 176.8 (2) |
C3—C4—C5—C6 | 1.1 (5) | C2—C1—N1—C7 | −134.9 (3) |
C4—C5—C6—C1 | −0.7 (4) | C6—C1—N1—C7 | 46.0 (3) |
C2—C1—C6—C5 | −0.7 (4) | C9—C10—N1—C1 | 169.3 (2) |
N1—C1—C6—C5 | 178.5 (2) | C9—C10—N1—C7 | −57.6 (3) |
N1—C7—C8—N2 | −58.0 (3) | C8—C7—N1—C1 | −168.0 (2) |
N2—C9—C10—N1 | 57.4 (3) | C8—C7—N1—C10 | 58.3 (3) |
O1—C11—C12—C13 | −178.4 (2) | C10—C9—N2—C8 | −56.6 (3) |
C16—C11—C12—C13 | 1.2 (3) | C7—C8—N2—C9 | 56.8 (3) |
O1—C11—C12—N3 | 0.0 (3) | C13—C12—N3—O3 | −141.4 (2) |
C16—C11—C12—N3 | 179.6 (2) | C11—C12—N3—O3 | 40.1 (3) |
C11—C12—C13—C14 | −2.0 (3) | C13—C12—N3—O2 | 37.9 (3) |
N3—C12—C13—C14 | 179.6 (2) | C11—C12—N3—O2 | −140.6 (2) |
C12—C13—C14—C15 | 0.8 (3) | C13—C14—N4—O5 | −174.7 (2) |
C12—C13—C14—N4 | −179.8 (2) | C15—C14—N4—O5 | 4.7 (3) |
C13—C14—C15—C16 | 0.9 (3) | C13—C14—N4—O4 | 6.0 (3) |
N4—C14—C15—C16 | −178.5 (2) | C15—C14—N4—O4 | −174.6 (2) |
C14—C15—C16—C11 | −1.7 (4) | C15—C16—N5—O7 | −146.1 (3) |
C14—C15—C16—N5 | 179.1 (2) | C11—C16—N5—O7 | 34.6 (3) |
O1—C11—C16—C15 | −179.7 (2) | C15—C16—N5—O6 | 33.4 (3) |
C12—C11—C16—C15 | 0.6 (3) | C11—C16—N5—O6 | −145.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8B···O4i | 0.97 | 2.42 | 3.265 (4) | 145 |
C9—H9A···O4ii | 0.97 | 2.60 | 3.353 (4) | 134 |
C9—H9A···O6iii | 0.97 | 2.61 | 3.455 (4) | 146 |
N2—H21···O2 | 0.83 (3) | 2.06 (3) | 2.871 (3) | 166 (3) |
N2—H21···O7iv | 0.83 (3) | 2.60 (3) | 2.985 (3) | 110 (2) |
N2—H22···O1iv | 0.98 (3) | 1.74 (3) | 2.705 (3) | 168 (3) |
N2—H21···O7iv | 0.83 (3) | 2.60 (3) | 2.985 (3) | 110 (2) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) x+1, y, z. |
C10H15N2+·C7H5O2−·H2O | F(000) = 648 |
Mr = 302.36 | Dx = 1.236 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.202 (2) Å | Cell parameters from 885 reflections |
b = 34.573 (9) Å | θ = 2.7–27.8° |
c = 7.596 (2) Å | µ = 0.09 mm−1 |
β = 93.83 (2)° | T = 293 K |
V = 1625.1 (8) Å3 | Rod, colourless |
Z = 4 | 0.32 × 0.20 × 0.16 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 1387 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.039 |
ω and φ scans | θmax = 27.8°, θmin = 2.9° |
Absorption correction: multi-scan (CrysalisRED; Oxford Diffraction, 2007) | h = −7→8 |
Tmin = 0.985, Tmax = 1.000 | k = −32→44 |
6075 measured reflections | l = −8→9 |
3492 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.065 | Hydrogen site location: mixed |
wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0549P)2] where P = (Fo2 + 2Fc2)/3 |
3492 reflections | (Δ/σ)max < 0.001 |
211 parameters | Δρmax = 0.24 e Å−3 |
4 restraints | Δρmin = −0.16 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 | ||
N1 | 0.2813 (3) | 0.60989 (6) | 0.7704 (3) | 0.0434 (6) | |
N2 | 0.2143 (4) | 0.52769 (7) | 0.7340 (3) | 0.0540 (7) | |
H21 | 0.175 (4) | 0.5046 (6) | 0.776 (3) | 0.065* | |
H22 | 0.244 (4) | 0.5249 (8) | 0.621 (2) | 0.065* | |
C1 | 0.3322 (4) | 0.64902 (8) | 0.7364 (3) | 0.0458 (7) | |
C2 | 0.1985 (5) | 0.67263 (9) | 0.6301 (4) | 0.0732 (9) | |
H2 | 0.073519 | 0.662304 | 0.574143 | 0.088* | |
C3 | 0.2469 (6) | 0.71136 (9) | 0.6050 (5) | 0.0890 (11) | |
H3 | 0.153321 | 0.726509 | 0.533416 | 0.107* | |
C4 | 0.4287 (7) | 0.72754 (10) | 0.6834 (5) | 0.0871 (11) | |
H4 | 0.460834 | 0.753486 | 0.666273 | 0.105* | |
C5 | 0.5623 (6) | 0.70463 (10) | 0.7878 (5) | 0.0849 (11) | |
H5 | 0.687062 | 0.715266 | 0.842693 | 0.102* | |
C6 | 0.5172 (5) | 0.66585 (9) | 0.8144 (4) | 0.0684 (9) | |
H6 | 0.612551 | 0.650963 | 0.885571 | 0.082* | |
C7 | 0.4623 (4) | 0.58257 (7) | 0.7779 (4) | 0.0500 (7) | |
H7A | 0.579852 | 0.592960 | 0.854289 | 0.060* | |
H7B | 0.513636 | 0.579710 | 0.660752 | 0.060* | |
C8 | 0.4003 (4) | 0.54349 (7) | 0.8453 (4) | 0.0554 (8) | |
H8A | 0.522296 | 0.525995 | 0.842923 | 0.067* | |
H8B | 0.361408 | 0.545749 | 0.966498 | 0.067* | |
C9 | 0.0303 (4) | 0.55502 (8) | 0.7319 (4) | 0.0586 (8) | |
H9A | −0.018777 | 0.557418 | 0.849982 | 0.070* | |
H9B | −0.088519 | 0.545041 | 0.655591 | 0.070* | |
C10 | 0.0951 (4) | 0.59416 (8) | 0.6670 (4) | 0.0544 (7) | |
H10A | 0.129289 | 0.592100 | 0.544591 | 0.065* | |
H10B | −0.025699 | 0.611834 | 0.672570 | 0.065* | |
O1 | 0.0826 (4) | 0.45352 (6) | 0.8352 (3) | 0.0739 (6) | |
O2 | 0.3636 (4) | 0.44271 (8) | 0.6833 (4) | 0.1271 (11) | |
C11 | 0.1746 (4) | 0.38836 (9) | 0.7732 (3) | 0.0488 (7) | |
C12 | 0.3158 (5) | 0.36281 (11) | 0.6979 (4) | 0.0710 (9) | |
H12 | 0.434100 | 0.372529 | 0.643180 | 0.085* | |
C13 | 0.2834 (6) | 0.32351 (12) | 0.7030 (4) | 0.0850 (11) | |
H13 | 0.378578 | 0.306980 | 0.650576 | 0.102* | |
C14 | 0.1131 (7) | 0.30867 (10) | 0.7841 (5) | 0.0841 (10) | |
H14 | 0.092772 | 0.282041 | 0.788617 | 0.101* | |
C15 | −0.0285 (5) | 0.33305 (10) | 0.8592 (4) | 0.0758 (10) | |
H15 | −0.145442 | 0.322946 | 0.914408 | 0.091* | |
C16 | 0.0017 (4) | 0.37282 (8) | 0.8532 (4) | 0.0566 (8) | |
H16 | −0.096028 | 0.389140 | 0.903761 | 0.068* | |
C17 | 0.2108 (5) | 0.43133 (10) | 0.7647 (4) | 0.0605 (8) | |
O3 | 0.7231 (3) | 0.47794 (7) | 0.6283 (3) | 0.0737 (7) | |
H31 | 0.816 (5) | 0.4679 (11) | 0.697 (4) | 0.111* | |
H32 | 0.609 (4) | 0.4665 (9) | 0.645 (5) | 0.111* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0406 (13) | 0.0418 (14) | 0.0472 (14) | −0.0004 (11) | −0.0012 (10) | −0.0001 (11) |
N2 | 0.0689 (17) | 0.0449 (15) | 0.0493 (16) | −0.0092 (14) | 0.0112 (14) | 0.0018 (14) |
C1 | 0.0524 (17) | 0.0389 (16) | 0.0463 (17) | −0.0012 (14) | 0.0049 (13) | −0.0033 (14) |
C2 | 0.074 (2) | 0.050 (2) | 0.092 (2) | −0.0010 (17) | −0.0224 (19) | 0.0050 (19) |
C3 | 0.109 (3) | 0.048 (2) | 0.106 (3) | 0.004 (2) | −0.026 (2) | 0.010 (2) |
C4 | 0.133 (3) | 0.044 (2) | 0.082 (3) | −0.014 (2) | −0.012 (2) | 0.000 (2) |
C5 | 0.105 (3) | 0.060 (2) | 0.086 (3) | −0.031 (2) | −0.024 (2) | 0.000 (2) |
C6 | 0.074 (2) | 0.054 (2) | 0.075 (2) | −0.0112 (18) | −0.0153 (17) | 0.0072 (17) |
C7 | 0.0442 (16) | 0.0485 (18) | 0.0566 (18) | −0.0019 (14) | −0.0008 (13) | −0.0016 (15) |
C8 | 0.0595 (18) | 0.0498 (18) | 0.0556 (18) | 0.0000 (15) | −0.0066 (15) | 0.0025 (15) |
C9 | 0.0512 (17) | 0.0590 (19) | 0.0659 (19) | −0.0085 (16) | 0.0071 (14) | −0.0031 (17) |
C10 | 0.0434 (16) | 0.0507 (18) | 0.068 (2) | −0.0008 (14) | −0.0024 (14) | 0.0025 (16) |
O1 | 0.0960 (16) | 0.0529 (14) | 0.0741 (15) | −0.0102 (12) | 0.0157 (13) | 0.0002 (12) |
O2 | 0.0889 (17) | 0.104 (2) | 0.195 (3) | −0.0264 (15) | 0.0568 (19) | 0.035 (2) |
C11 | 0.0447 (16) | 0.0594 (19) | 0.0417 (16) | 0.0016 (15) | −0.0014 (13) | 0.0053 (15) |
C12 | 0.062 (2) | 0.089 (3) | 0.063 (2) | 0.017 (2) | 0.0069 (16) | 0.0160 (19) |
C13 | 0.106 (3) | 0.077 (3) | 0.072 (2) | 0.040 (2) | 0.007 (2) | 0.002 (2) |
C14 | 0.125 (3) | 0.053 (2) | 0.073 (2) | 0.003 (2) | −0.009 (2) | −0.004 (2) |
C15 | 0.087 (2) | 0.062 (2) | 0.079 (2) | −0.023 (2) | 0.0130 (19) | 0.000 (2) |
C16 | 0.0602 (18) | 0.055 (2) | 0.0557 (18) | −0.0061 (16) | 0.0122 (15) | −0.0043 (15) |
C17 | 0.056 (2) | 0.066 (2) | 0.059 (2) | −0.0128 (18) | −0.0014 (16) | 0.0198 (18) |
O3 | 0.0697 (16) | 0.0830 (17) | 0.0700 (15) | −0.0213 (13) | 0.0159 (12) | −0.0070 (13) |
N1—C1 | 1.417 (3) | C8—H8B | 0.9700 |
N1—C10 | 1.458 (3) | C9—C10 | 1.504 (3) |
N1—C7 | 1.465 (3) | C9—H9A | 0.9700 |
N2—C9 | 1.481 (3) | C9—H9B | 0.9700 |
N2—C8 | 1.488 (3) | C10—H10A | 0.9700 |
N2—H21 | 0.898 (17) | C10—H10B | 0.9700 |
N2—H22 | 0.893 (16) | O1—C17 | 1.251 (3) |
C1—C6 | 1.384 (3) | O2—C17 | 1.230 (3) |
C1—C2 | 1.384 (3) | C11—C16 | 1.376 (3) |
C2—C3 | 1.388 (4) | C11—C12 | 1.393 (4) |
C2—H2 | 0.9300 | C11—C17 | 1.504 (4) |
C3—C4 | 1.360 (4) | C12—C13 | 1.375 (4) |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C5 | 1.362 (4) | C13—C14 | 1.358 (4) |
C4—H4 | 0.9300 | C13—H13 | 0.9300 |
C5—C6 | 1.387 (4) | C14—C15 | 1.369 (4) |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C6—H6 | 0.9300 | C15—C16 | 1.389 (4) |
C7—C8 | 1.504 (3) | C15—H15 | 0.9300 |
C7—H7A | 0.9700 | C16—H16 | 0.9300 |
C7—H7B | 0.9700 | O3—H31 | 0.830 (18) |
C8—H8A | 0.9700 | O3—H32 | 0.826 (18) |
C1—N1—C10 | 115.8 (2) | C7—C8—H8B | 109.7 |
C1—N1—C7 | 116.32 (19) | H8A—C8—H8B | 108.2 |
C10—N1—C7 | 110.9 (2) | N2—C9—C10 | 110.8 (2) |
C9—N2—C8 | 109.8 (2) | N2—C9—H9A | 109.5 |
C9—N2—H21 | 110.3 (17) | C10—C9—H9A | 109.5 |
C8—N2—H21 | 110.0 (17) | N2—C9—H9B | 109.5 |
C9—N2—H22 | 105.5 (17) | C10—C9—H9B | 109.5 |
C8—N2—H22 | 112.5 (17) | H9A—C9—H9B | 108.1 |
H21—N2—H22 | 109 (3) | N1—C10—C9 | 112.3 (2) |
C6—C1—C2 | 116.7 (3) | N1—C10—H10A | 109.2 |
C6—C1—N1 | 120.8 (2) | C9—C10—H10A | 109.2 |
C2—C1—N1 | 122.5 (3) | N1—C10—H10B | 109.2 |
C1—C2—C3 | 121.5 (3) | C9—C10—H10B | 109.2 |
C1—C2—H2 | 119.3 | H10A—C10—H10B | 107.9 |
C3—C2—H2 | 119.3 | C16—C11—C12 | 117.6 (3) |
C4—C3—C2 | 121.2 (3) | C16—C11—C17 | 121.8 (3) |
C4—C3—H3 | 119.4 | C12—C11—C17 | 120.6 (3) |
C2—C3—H3 | 119.4 | C13—C12—C11 | 121.2 (3) |
C3—C4—C5 | 118.0 (3) | C13—C12—H12 | 119.4 |
C3—C4—H4 | 121.0 | C11—C12—H12 | 119.4 |
C5—C4—H4 | 121.0 | C14—C13—C12 | 120.4 (3) |
C4—C5—C6 | 121.7 (3) | C14—C13—H13 | 119.8 |
C4—C5—H5 | 119.1 | C12—C13—H13 | 119.8 |
C6—C5—H5 | 119.1 | C13—C14—C15 | 119.7 (3) |
C1—C6—C5 | 120.9 (3) | C13—C14—H14 | 120.1 |
C1—C6—H6 | 119.5 | C15—C14—H14 | 120.1 |
C5—C6—H6 | 119.5 | C14—C15—C16 | 120.3 (3) |
N1—C7—C8 | 112.3 (2) | C14—C15—H15 | 119.9 |
N1—C7—H7A | 109.1 | C16—C15—H15 | 119.9 |
C8—C7—H7A | 109.1 | C11—C16—C15 | 120.8 (3) |
N1—C7—H7B | 109.1 | C11—C16—H16 | 119.6 |
C8—C7—H7B | 109.1 | C15—C16—H16 | 119.6 |
H7A—C7—H7B | 107.9 | O2—C17—O1 | 123.5 (3) |
N2—C8—C7 | 110.0 (2) | O2—C17—C11 | 117.4 (3) |
N2—C8—H8A | 109.7 | O1—C17—C11 | 119.1 (3) |
C7—C8—H8A | 109.7 | H31—O3—H32 | 106 (4) |
N2—C8—H8B | 109.7 | ||
C10—N1—C1—C6 | −173.8 (2) | C8—N2—C9—C10 | 57.0 (3) |
C7—N1—C1—C6 | −40.8 (3) | C1—N1—C10—C9 | −170.5 (2) |
C10—N1—C1—C2 | 8.5 (3) | C7—N1—C10—C9 | 54.1 (3) |
C7—N1—C1—C2 | 141.5 (3) | N2—C9—C10—N1 | −56.0 (3) |
C6—C1—C2—C3 | −0.8 (4) | C16—C11—C12—C13 | 0.1 (4) |
N1—C1—C2—C3 | 177.0 (3) | C17—C11—C12—C13 | −179.3 (3) |
C1—C2—C3—C4 | 0.4 (5) | C11—C12—C13—C14 | −0.8 (5) |
C2—C3—C4—C5 | −0.1 (5) | C12—C13—C14—C15 | 0.9 (5) |
C3—C4—C5—C6 | 0.2 (5) | C13—C14—C15—C16 | −0.2 (5) |
C2—C1—C6—C5 | 0.8 (4) | C12—C11—C16—C15 | 0.5 (4) |
N1—C1—C6—C5 | −177.0 (3) | C17—C11—C16—C15 | 179.9 (3) |
C4—C5—C6—C1 | −0.6 (5) | C14—C15—C16—C11 | −0.5 (5) |
C1—N1—C7—C8 | 170.0 (2) | C16—C11—C17—O2 | −176.6 (3) |
C10—N1—C7—C8 | −54.7 (3) | C12—C11—C17—O2 | 2.8 (4) |
C9—N2—C8—C7 | −57.2 (3) | C16—C11—C17—O1 | 1.4 (4) |
N1—C7—C8—N2 | 56.6 (3) | C12—C11—C17—O1 | −179.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O1 | 0.90 (2) | 1.92 (2) | 2.813 (3) | 173 (2) |
N2—H21···O2 | 0.90 (2) | 2.56 (2) | 3.112 (4) | 121 (2) |
N2—H22···O3i | 0.89 (2) | 1.92 (2) | 2.812 (3) | 173 (2) |
C9—H9A···O1ii | 0.97 | 2.48 | 3.420 (4) | 164 |
C9—H9B···O3iii | 0.97 | 2.60 | 3.340 (4) | 133 |
O3—H31···O1iv | 0.83 (2) | 1.96 (2) | 2.772 (3) | 166 (4) |
O3—H32···O2 | 0.83 (2) | 1.77 (2) | 2.599 (3) | 179 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+2; (iii) x−1, y, z; (iv) x+1, y, z. |
C10H15N2+·C7H7O3S− | F(000) = 712 |
Mr = 334.42 | Dx = 1.325 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.325 (1) Å | Cell parameters from 2252 reflections |
b = 10.949 (2) Å | θ = 2.9–27.6° |
c = 18.418 (4) Å | µ = 0.21 mm−1 |
β = 92.67 (2)° | T = 293 K |
V = 1677.0 (5) Å3 | Plate, colourless |
Z = 4 | 0.50 × 0.36 × 0.14 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 2767 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.044 |
Rotation method data acquisition using ω scans. | θmax = 27.7°, θmin = 2.9° |
Absorption correction: multi-scan (CrysalisRED; Oxford Diffraction, 2007) | h = −10→9 |
Tmin = 0.696, Tmax = 1.000 | k = −14→11 |
6123 measured reflections | l = −24→20 |
4918 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)] = 0.126 | H-atom parameters constrained |
wR(F2) = 0.298 | w = 1/[σ2(Fo2) + (0.0541P)2 + 11.2654P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
4918 reflections | Δρmax = 1.08 e Å−3 |
480 parameters | Δρmin = −0.41 e Å−3 |
853 restraints | Absolute structure: Flack x determined using 597 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: dual | Absolute structure parameter: 0.00 (11) |
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. |
Refinement. Refined as a 2-component twin. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.3198 (15) | 0.0451 (12) | 0.1981 (8) | 0.044 (3) | |
N2 | 0.3315 (13) | −0.0070 (11) | 0.0453 (8) | 0.041 (3) | |
H21N | 0.301100 | 0.008772 | −0.000733 | 0.050* | |
H22N | 0.400866 | −0.068854 | 0.045658 | 0.050* | |
C1 | 0.345 (5) | 0.050 (4) | 0.2756 (14) | 0.056 (4) | 0.49 (7) |
C2 | 0.244 (4) | −0.010 (4) | 0.322 (2) | 0.058 (4) | 0.49 (7) |
H2 | 0.163707 | −0.061632 | 0.302457 | 0.069* | 0.49 (7) |
C3 | 0.263 (4) | 0.006 (5) | 0.3965 (19) | 0.060 (4) | 0.49 (7) |
H3 | 0.195547 | −0.034965 | 0.427260 | 0.073* | 0.49 (7) |
C4 | 0.383 (5) | 0.082 (4) | 0.4252 (14) | 0.062 (4) | 0.49 (7) |
H4 | 0.395978 | 0.092749 | 0.475215 | 0.074* | 0.49 (7) |
C5 | 0.484 (6) | 0.143 (3) | 0.3791 (18) | 0.061 (4) | 0.49 (7) |
H5 | 0.564573 | 0.193797 | 0.398368 | 0.074* | 0.49 (7) |
C6 | 0.465 (5) | 0.127 (4) | 0.3044 (17) | 0.058 (4) | 0.49 (7) |
H6 | 0.532736 | 0.167132 | 0.273565 | 0.070* | 0.49 (7) |
C1A | 0.338 (4) | 0.047 (3) | 0.2748 (13) | 0.055 (3) | 0.51 (7) |
C2A | 0.259 (5) | −0.042 (4) | 0.3132 (19) | 0.057 (4) | 0.51 (7) |
H2A | 0.204660 | −0.104759 | 0.288426 | 0.069* | 0.51 (7) |
C3A | 0.261 (4) | −0.038 (4) | 0.3887 (19) | 0.061 (4) | 0.51 (7) |
H3A | 0.207972 | −0.097323 | 0.414372 | 0.073* | 0.51 (7) |
C4A | 0.342 (5) | 0.056 (4) | 0.4258 (13) | 0.062 (4) | 0.51 (7) |
H4A | 0.342913 | 0.059306 | 0.476246 | 0.075* | 0.51 (7) |
C5A | 0.420 (7) | 0.146 (2) | 0.3874 (18) | 0.060 (4) | 0.51 (7) |
H5A | 0.474543 | 0.208501 | 0.412173 | 0.072* | 0.51 (7) |
C6A | 0.418 (5) | 0.141 (3) | 0.3119 (18) | 0.059 (4) | 0.51 (7) |
H6A | 0.471233 | 0.201067 | 0.286226 | 0.070* | 0.51 (7) |
C7 | 0.4521 (18) | 0.0840 (15) | 0.1564 (9) | 0.049 (4) | |
H7A | 0.537245 | 0.023733 | 0.161521 | 0.059* | |
H7B | 0.493647 | 0.160291 | 0.176389 | 0.059* | |
C8 | 0.411 (2) | 0.1017 (15) | 0.0780 (9) | 0.052 (4) | |
H8A | 0.339429 | 0.171509 | 0.071858 | 0.063* | |
H8B | 0.507744 | 0.119164 | 0.052790 | 0.063* | |
C9 | 0.1907 (17) | −0.0413 (16) | 0.0857 (9) | 0.046 (4) | |
H9A | 0.144478 | −0.115915 | 0.065528 | 0.056* | |
H9B | 0.110126 | 0.022516 | 0.080775 | 0.056* | |
C10 | 0.2369 (19) | −0.0603 (15) | 0.1653 (10) | 0.049 (4) | |
H10A | 0.140631 | −0.076696 | 0.191354 | 0.059* | |
H10B | 0.306204 | −0.131345 | 0.170331 | 0.059* | |
S1 | 0.1579 (4) | 0.7481 (4) | −0.1011 (2) | 0.0439 (10) | |
O1 | 0.1787 (12) | 0.6159 (9) | −0.0944 (6) | 0.049 (3) | |
O2 | 0.2928 (18) | 0.8175 (11) | −0.0705 (7) | 0.076 (4) | |
O3 | 0.0028 (16) | 0.7862 (13) | −0.0762 (7) | 0.082 (5) | |
C11 | 0.1506 (16) | 0.7750 (13) | −0.1938 (8) | 0.036 (3) | |
C12 | 0.2354 (19) | 0.8746 (17) | −0.2240 (10) | 0.054 (4) | |
H12 | 0.298418 | 0.925481 | −0.193938 | 0.065* | |
C13 | 0.224 (2) | 0.8952 (19) | −0.2971 (11) | 0.067 (5) | |
H13 | 0.283222 | 0.959399 | −0.315160 | 0.081* | |
C14 | 0.133 (2) | 0.830 (2) | −0.3450 (11) | 0.070 (5) | |
C15 | 0.042 (2) | 0.735 (2) | −0.3146 (10) | 0.069 (5) | |
H15 | −0.025524 | 0.687927 | −0.344707 | 0.083* | |
C16 | 0.051 (2) | 0.7130 (15) | −0.2414 (9) | 0.060 (5) | |
H16 | −0.013532 | 0.652069 | −0.223331 | 0.072* | |
C17 | 0.121 (3) | 0.853 (3) | −0.4249 (11) | 0.101 (8) | |
H17A | 0.138438 | 0.778329 | −0.450528 | 0.152* | |
H17B | 0.200838 | 0.911924 | −0.437227 | 0.152* | |
H17C | 0.015970 | 0.884299 | −0.438319 | 0.152* | |
N3 | 0.2216 (15) | 0.5462 (13) | 0.1956 (8) | 0.046 (3) | |
N4 | 0.1795 (13) | 0.4911 (11) | 0.0439 (8) | 0.041 (3) | |
H41N | 0.110853 | 0.428961 | 0.045763 | 0.049* | |
H42N | 0.200180 | 0.504089 | −0.002420 | 0.049* | |
C18 | 0.212 (4) | 0.553 (3) | 0.2730 (13) | 0.052 (3) | 0.53 (7) |
C19 | 0.321 (4) | 0.490 (4) | 0.3187 (18) | 0.055 (4) | 0.53 (7) |
H19 | 0.395669 | 0.437535 | 0.299289 | 0.066* | 0.53 (7) |
C20 | 0.319 (3) | 0.506 (4) | 0.3935 (17) | 0.058 (4) | 0.53 (7) |
H20 | 0.392116 | 0.464559 | 0.424139 | 0.070* | 0.53 (7) |
C21 | 0.208 (5) | 0.585 (3) | 0.4226 (13) | 0.060 (4) | 0.53 (7) |
H21 | 0.206786 | 0.596177 | 0.472606 | 0.071* | 0.53 (7) |
C22 | 0.099 (6) | 0.648 (3) | 0.3768 (17) | 0.058 (4) | 0.53 (7) |
H22 | 0.025007 | 0.700772 | 0.396224 | 0.070* | 0.53 (7) |
C23 | 0.101 (5) | 0.632 (3) | 0.3020 (16) | 0.056 (4) | 0.53 (7) |
H23 | 0.028557 | 0.673749 | 0.271374 | 0.067* | 0.53 (7) |
C18A | 0.222 (5) | 0.547 (4) | 0.2737 (15) | 0.053 (3) | 0.47 (7) |
C19A | 0.308 (5) | 0.459 (4) | 0.313 (2) | 0.054 (4) | 0.47 (7) |
H19A | 0.355887 | 0.394865 | 0.289012 | 0.065* | 0.47 (7) |
C20A | 0.322 (4) | 0.466 (4) | 0.388 (2) | 0.057 (4) | 0.47 (7) |
H20A | 0.379451 | 0.406632 | 0.414826 | 0.069* | 0.47 (7) |
C21A | 0.250 (6) | 0.562 (4) | 0.4245 (15) | 0.059 (4) | 0.47 (7) |
H21A | 0.259318 | 0.566251 | 0.474911 | 0.071* | 0.47 (7) |
C22A | 0.164 (7) | 0.650 (3) | 0.385 (2) | 0.058 (4) | 0.47 (7) |
H22A | 0.115621 | 0.714105 | 0.409183 | 0.070* | 0.47 (7) |
C23A | 0.150 (6) | 0.643 (3) | 0.310 (2) | 0.057 (4) | 0.47 (7) |
H23A | 0.092056 | 0.702341 | 0.283368 | 0.068* | 0.47 (7) |
C24 | 0.2995 (19) | 0.4424 (17) | 0.1647 (10) | 0.053 (4) | |
H24A | 0.233128 | 0.370513 | 0.170301 | 0.064* | |
H24B | 0.401590 | 0.428310 | 0.190816 | 0.064* | |
C25 | 0.3281 (16) | 0.4609 (14) | 0.0851 (9) | 0.042 (3) | |
H25A | 0.405263 | 0.526314 | 0.079855 | 0.051* | |
H25B | 0.373358 | 0.386948 | 0.065500 | 0.051* | |
C26 | 0.107 (2) | 0.6013 (14) | 0.0745 (9) | 0.049 (4) | |
H26A | 0.005379 | 0.618567 | 0.048646 | 0.058* | |
H26B | 0.177715 | 0.670632 | 0.068350 | 0.058* | |
C27 | 0.0796 (19) | 0.5836 (16) | 0.1541 (9) | 0.050 (4) | |
H27A | 0.040882 | 0.659632 | 0.173988 | 0.059* | |
H27B | −0.003443 | 0.522492 | 0.159258 | 0.059* | |
S2 | 0.3197 (4) | 0.2483 (4) | −0.1000 (2) | 0.0434 (10) | |
O4 | 0.4827 (15) | 0.2874 (13) | −0.0758 (7) | 0.082 (5) | |
O5 | 0.1897 (18) | 0.3143 (12) | −0.0704 (7) | 0.076 (4) | |
O6 | 0.3029 (13) | 0.1184 (10) | −0.0925 (6) | 0.055 (3) | |
C28 | 0.3101 (15) | 0.2744 (12) | −0.1926 (7) | 0.030 (3) | |
C29 | 0.398 (2) | 0.2104 (14) | −0.2397 (9) | 0.056 (4) | |
H29 | 0.464748 | 0.148626 | −0.221269 | 0.067* | |
C30 | 0.393 (2) | 0.2318 (19) | −0.3126 (9) | 0.069 (5) | |
H30 | 0.454820 | 0.183365 | −0.341942 | 0.083* | |
C31 | 0.299 (3) | 0.3227 (19) | −0.3444 (11) | 0.067 (5) | |
C32 | 0.213 (2) | 0.3916 (17) | −0.2971 (11) | 0.063 (5) | |
H32 | 0.149972 | 0.455303 | −0.315993 | 0.076* | |
C33 | 0.2151 (19) | 0.3708 (15) | −0.2229 (11) | 0.051 (4) | |
H33 | 0.154699 | 0.419715 | −0.193132 | 0.061* | |
C34 | 0.291 (3) | 0.347 (3) | −0.4236 (12) | 0.108 (9) | |
H34A | 0.211715 | 0.408803 | −0.434536 | 0.163* | |
H34B | 0.261493 | 0.273269 | −0.449234 | 0.163* | |
H34C | 0.393878 | 0.374298 | −0.438393 | 0.163* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.035 (6) | 0.025 (6) | 0.073 (6) | −0.004 (5) | 0.003 (5) | 0.004 (5) |
N2 | 0.022 (6) | 0.028 (7) | 0.075 (9) | −0.001 (5) | 0.003 (5) | −0.001 (6) |
C1 | 0.057 (8) | 0.041 (8) | 0.070 (6) | −0.002 (7) | 0.006 (6) | 0.002 (6) |
C2 | 0.060 (8) | 0.043 (8) | 0.070 (7) | −0.006 (7) | 0.006 (6) | 0.000 (7) |
C3 | 0.065 (8) | 0.046 (9) | 0.071 (7) | −0.008 (8) | 0.007 (6) | −0.001 (7) |
C4 | 0.065 (9) | 0.049 (9) | 0.072 (7) | −0.009 (8) | 0.005 (7) | 0.000 (7) |
C5 | 0.062 (9) | 0.049 (8) | 0.073 (7) | −0.007 (8) | 0.006 (7) | −0.002 (7) |
C6 | 0.059 (9) | 0.045 (8) | 0.071 (6) | −0.004 (7) | 0.007 (7) | −0.001 (7) |
C1A | 0.056 (8) | 0.041 (7) | 0.070 (6) | −0.002 (7) | 0.007 (6) | 0.002 (6) |
C2A | 0.058 (8) | 0.044 (8) | 0.071 (6) | −0.004 (7) | 0.007 (6) | 0.001 (7) |
C3A | 0.065 (8) | 0.046 (9) | 0.071 (7) | −0.009 (8) | 0.007 (7) | 0.001 (7) |
C4A | 0.065 (9) | 0.050 (8) | 0.072 (7) | −0.009 (8) | 0.005 (7) | 0.001 (7) |
C5A | 0.061 (9) | 0.048 (8) | 0.072 (7) | −0.007 (8) | 0.006 (7) | −0.001 (7) |
C6A | 0.059 (9) | 0.046 (8) | 0.071 (6) | −0.006 (7) | 0.007 (7) | 0.000 (6) |
C7 | 0.033 (7) | 0.041 (10) | 0.073 (7) | −0.010 (7) | 0.004 (6) | −0.009 (8) |
C8 | 0.051 (9) | 0.029 (8) | 0.077 (8) | −0.016 (7) | 0.004 (7) | 0.005 (8) |
C9 | 0.031 (7) | 0.036 (9) | 0.073 (8) | −0.007 (6) | 0.009 (6) | −0.010 (8) |
C10 | 0.038 (9) | 0.035 (9) | 0.076 (8) | −0.012 (7) | 0.012 (7) | 0.003 (7) |
S1 | 0.042 (2) | 0.029 (2) | 0.061 (3) | 0.009 (2) | 0.0026 (17) | −0.003 (2) |
O1 | 0.046 (7) | 0.018 (5) | 0.083 (8) | 0.002 (5) | 0.006 (5) | 0.004 (5) |
O2 | 0.114 (10) | 0.036 (7) | 0.076 (9) | −0.037 (7) | −0.030 (8) | 0.007 (7) |
O3 | 0.077 (8) | 0.095 (11) | 0.078 (8) | 0.057 (8) | 0.038 (7) | 0.019 (8) |
C11 | 0.031 (4) | 0.034 (4) | 0.043 (4) | 0.001 (3) | 0.002 (3) | −0.003 (3) |
C12 | 0.037 (9) | 0.057 (10) | 0.068 (8) | −0.018 (8) | 0.000 (7) | 0.005 (8) |
C13 | 0.064 (12) | 0.068 (13) | 0.070 (9) | −0.016 (9) | 0.011 (8) | 0.013 (9) |
C14 | 0.067 (12) | 0.080 (13) | 0.062 (9) | 0.005 (9) | 0.002 (8) | 0.000 (9) |
C15 | 0.076 (11) | 0.064 (12) | 0.067 (8) | −0.009 (10) | −0.017 (8) | −0.012 (9) |
C16 | 0.069 (10) | 0.039 (11) | 0.069 (8) | −0.017 (8) | −0.013 (8) | −0.002 (7) |
C17 | 0.108 (19) | 0.13 (2) | 0.068 (10) | 0.026 (17) | 0.009 (11) | 0.013 (12) |
N3 | 0.033 (6) | 0.037 (7) | 0.067 (5) | −0.005 (5) | −0.002 (5) | 0.001 (6) |
N4 | 0.024 (6) | 0.023 (6) | 0.076 (8) | −0.006 (5) | 0.006 (5) | 0.005 (6) |
C18 | 0.048 (8) | 0.040 (7) | 0.067 (6) | −0.001 (7) | −0.002 (5) | 0.004 (6) |
C19 | 0.052 (7) | 0.044 (8) | 0.068 (6) | 0.004 (7) | −0.003 (6) | 0.002 (7) |
C20 | 0.058 (8) | 0.046 (9) | 0.069 (6) | 0.007 (8) | −0.002 (6) | 0.003 (7) |
C21 | 0.058 (9) | 0.049 (8) | 0.071 (7) | 0.008 (8) | −0.002 (6) | 0.003 (7) |
C22 | 0.055 (9) | 0.048 (8) | 0.071 (7) | 0.007 (8) | −0.003 (7) | 0.000 (7) |
C23 | 0.051 (8) | 0.045 (7) | 0.071 (6) | 0.005 (7) | −0.003 (6) | 0.001 (7) |
C18A | 0.049 (8) | 0.041 (7) | 0.067 (6) | −0.001 (7) | −0.002 (6) | 0.003 (6) |
C19A | 0.051 (8) | 0.043 (8) | 0.068 (6) | 0.002 (7) | −0.002 (6) | 0.003 (7) |
C20A | 0.057 (8) | 0.045 (9) | 0.069 (6) | 0.008 (8) | −0.003 (6) | 0.003 (7) |
C21A | 0.058 (9) | 0.048 (8) | 0.071 (7) | 0.009 (8) | −0.001 (7) | 0.002 (7) |
C22A | 0.056 (9) | 0.047 (8) | 0.072 (7) | 0.007 (8) | −0.002 (7) | 0.000 (7) |
C23A | 0.053 (9) | 0.045 (7) | 0.071 (6) | 0.003 (8) | −0.003 (7) | 0.000 (6) |
C24 | 0.029 (8) | 0.052 (10) | 0.079 (8) | 0.010 (7) | 0.000 (7) | 0.004 (8) |
C25 | 0.022 (6) | 0.022 (8) | 0.083 (8) | −0.004 (6) | 0.003 (6) | −0.005 (7) |
C26 | 0.052 (9) | 0.021 (7) | 0.073 (8) | 0.012 (7) | 0.003 (7) | 0.008 (7) |
C27 | 0.047 (4) | 0.047 (5) | 0.054 (4) | 0.005 (3) | 0.001 (3) | −0.002 (3) |
S2 | 0.041 (2) | 0.030 (2) | 0.059 (3) | −0.014 (2) | 0.0019 (17) | −0.002 (2) |
O4 | 0.072 (7) | 0.087 (11) | 0.082 (9) | −0.056 (7) | −0.035 (6) | 0.031 (8) |
O5 | 0.107 (10) | 0.048 (8) | 0.076 (9) | 0.008 (7) | 0.035 (8) | 0.000 (7) |
O6 | 0.058 (7) | 0.026 (6) | 0.082 (9) | −0.017 (5) | −0.004 (6) | 0.009 (6) |
C28 | 0.025 (4) | 0.025 (4) | 0.039 (4) | −0.008 (3) | 0.002 (3) | −0.003 (3) |
C29 | 0.075 (11) | 0.033 (10) | 0.061 (8) | 0.011 (7) | 0.011 (8) | −0.004 (7) |
C30 | 0.097 (13) | 0.053 (12) | 0.059 (8) | 0.003 (9) | 0.018 (8) | −0.015 (8) |
C31 | 0.069 (12) | 0.063 (12) | 0.068 (9) | −0.021 (8) | −0.005 (8) | 0.005 (8) |
C32 | 0.058 (12) | 0.044 (11) | 0.087 (9) | 0.000 (8) | −0.008 (8) | 0.019 (9) |
C33 | 0.035 (8) | 0.031 (8) | 0.087 (9) | 0.005 (6) | 0.001 (8) | 0.007 (8) |
C34 | 0.11 (2) | 0.13 (2) | 0.076 (10) | −0.039 (18) | −0.012 (11) | 0.022 (13) |
N1—C1A | 1.41 (3) | N3—C18 | 1.43 (3) |
N1—C1 | 1.44 (3) | N3—C27 | 1.437 (19) |
N1—C7 | 1.437 (19) | N3—C18A | 1.44 (3) |
N1—C10 | 1.461 (19) | N3—C24 | 1.44 (2) |
N2—C9 | 1.467 (18) | N4—C25 | 1.459 (19) |
N2—C8 | 1.475 (19) | N4—C26 | 1.473 (18) |
N2—H21N | 0.8900 | N4—H41N | 0.8900 |
N2—H22N | 0.8900 | N4—H42N | 0.8900 |
C1—C2 | 1.3900 | C18—C19 | 1.3900 |
C1—C6 | 1.3900 | C18—C23 | 1.3900 |
C2—C3 | 1.3900 | C19—C20 | 1.3900 |
C2—H2 | 0.9300 | C19—H19 | 0.9300 |
C3—C4 | 1.3900 | C20—C21 | 1.3900 |
C3—H3 | 0.9300 | C20—H20 | 0.9300 |
C4—C5 | 1.3900 | C21—C22 | 1.3900 |
C4—H4 | 0.9300 | C21—H21 | 0.9300 |
C5—C6 | 1.3900 | C22—C23 | 1.3900 |
C5—H5 | 0.9300 | C22—H22 | 0.9300 |
C6—H6 | 0.9300 | C23—H23 | 0.9300 |
C1A—C2A | 1.3900 | C18A—C19A | 1.3900 |
C1A—C6A | 1.3900 | C18A—C23A | 1.3900 |
C2A—C3A | 1.3900 | C19A—C20A | 1.3900 |
C2A—H2A | 0.9300 | C19A—H19A | 0.9300 |
C3A—C4A | 1.3900 | C20A—C21A | 1.3900 |
C3A—H3A | 0.9300 | C20A—H20A | 0.9300 |
C4A—C5A | 1.3900 | C21A—C22A | 1.3900 |
C4A—H4A | 0.9300 | C21A—H21A | 0.9300 |
C5A—C6A | 1.3900 | C22A—C23A | 1.3900 |
C5A—H5A | 0.9300 | C22A—H22A | 0.9300 |
C6A—H6A | 0.9300 | C23A—H23A | 0.9300 |
C7—C8 | 1.48 (2) | C24—C25 | 1.51 (2) |
C7—H7A | 0.9700 | C24—H24A | 0.9700 |
C7—H7B | 0.9700 | C24—H24B | 0.9700 |
C8—H8A | 0.9700 | C25—H25A | 0.9700 |
C8—H8B | 0.9700 | C25—H25B | 0.9700 |
C9—C10 | 1.51 (2) | C26—C27 | 1.51 (2) |
C9—H9A | 0.9700 | C26—H26A | 0.9700 |
C9—H9B | 0.9700 | C26—H26B | 0.9700 |
C10—H10A | 0.9700 | C27—H27A | 0.9700 |
C10—H10B | 0.9700 | C27—H27B | 0.9700 |
S1—O2 | 1.448 (12) | S2—O5 | 1.430 (13) |
S1—O3 | 1.451 (12) | S2—O6 | 1.436 (11) |
S1—O1 | 1.462 (11) | S2—O4 | 1.473 (11) |
S1—C11 | 1.731 (15) | S2—C28 | 1.728 (14) |
C11—C16 | 1.358 (19) | C28—C29 | 1.355 (19) |
C11—C12 | 1.43 (2) | C28—C33 | 1.42 (2) |
C12—C13 | 1.36 (2) | C29—C30 | 1.36 (2) |
C12—H12 | 0.9300 | C29—H29 | 0.9300 |
C13—C14 | 1.34 (3) | C30—C31 | 1.38 (3) |
C13—H13 | 0.9300 | C30—H30 | 0.9300 |
C14—C15 | 1.41 (3) | C31—C32 | 1.38 (3) |
C14—C17 | 1.49 (3) | C31—C34 | 1.48 (3) |
C15—C16 | 1.37 (2) | C32—C33 | 1.39 (3) |
C15—H15 | 0.9300 | C32—H32 | 0.9300 |
C16—H16 | 0.9300 | C33—H33 | 0.9300 |
C17—H17A | 0.9600 | C34—H34A | 0.9600 |
C17—H17B | 0.9600 | C34—H34B | 0.9600 |
C17—H17C | 0.9600 | C34—H34C | 0.9600 |
C1A—N1—C7 | 118.8 (19) | C18—N3—C27 | 115.7 (18) |
C1—N1—C7 | 116.1 (19) | C27—N3—C18A | 119 (2) |
C1A—N1—C10 | 116.9 (19) | C18—N3—C24 | 118.7 (19) |
C1—N1—C10 | 119.1 (19) | C27—N3—C24 | 112.9 (14) |
C7—N1—C10 | 111.9 (13) | C18A—N3—C24 | 115 (2) |
C9—N2—C8 | 110.6 (13) | C25—N4—C26 | 109.8 (13) |
C9—N2—H21N | 109.5 | C25—N4—H41N | 109.7 |
C8—N2—H21N | 109.5 | C26—N4—H41N | 109.7 |
C9—N2—H22N | 109.5 | C25—N4—H42N | 109.7 |
C8—N2—H22N | 109.5 | C26—N4—H42N | 109.7 |
H21N—N2—H22N | 108.1 | H41N—N4—H42N | 108.2 |
C2—C1—C6 | 120.0 | C19—C18—C23 | 120.0 |
C2—C1—N1 | 122 (2) | C19—C18—N3 | 121 (2) |
C6—C1—N1 | 118 (2) | C23—C18—N3 | 119 (2) |
C3—C2—C1 | 120.0 | C20—C19—C18 | 120.0 |
C3—C2—H2 | 120.0 | C20—C19—H19 | 120.0 |
C1—C2—H2 | 120.0 | C18—C19—H19 | 120.0 |
C2—C3—C4 | 120.0 | C21—C20—C19 | 120.0 |
C2—C3—H3 | 120.0 | C21—C20—H20 | 120.0 |
C4—C3—H3 | 120.0 | C19—C20—H20 | 120.0 |
C3—C4—C5 | 120.0 | C22—C21—C20 | 120.0 |
C3—C4—H4 | 120.0 | C22—C21—H21 | 120.0 |
C5—C4—H4 | 120.0 | C20—C21—H21 | 120.0 |
C6—C5—C4 | 120.0 | C21—C22—C23 | 120.0 |
C6—C5—H5 | 120.0 | C21—C22—H22 | 120.0 |
C4—C5—H5 | 120.0 | C23—C22—H22 | 120.0 |
C5—C6—C1 | 120.0 | C22—C23—C18 | 120.0 |
C5—C6—H6 | 120.0 | C22—C23—H23 | 120.0 |
C1—C6—H6 | 120.0 | C18—C23—H23 | 120.0 |
C2A—C1A—C6A | 120.0 | C19A—C18A—C23A | 120.0 |
C2A—C1A—N1 | 118 (2) | C19A—C18A—N3 | 119 (3) |
C6A—C1A—N1 | 122 (2) | C23A—C18A—N3 | 120 (3) |
C1A—C2A—C3A | 120.0 | C20A—C19A—C18A | 120.0 |
C1A—C2A—H2A | 120.0 | C20A—C19A—H19A | 120.0 |
C3A—C2A—H2A | 120.0 | C18A—C19A—H19A | 120.0 |
C4A—C3A—C2A | 120.0 | C19A—C20A—C21A | 120.0 |
C4A—C3A—H3A | 120.0 | C19A—C20A—H20A | 120.0 |
C2A—C3A—H3A | 120.0 | C21A—C20A—H20A | 120.0 |
C3A—C4A—C5A | 120.0 | C20A—C21A—C22A | 120.0 |
C3A—C4A—H4A | 120.0 | C20A—C21A—H21A | 120.0 |
C5A—C4A—H4A | 120.0 | C22A—C21A—H21A | 120.0 |
C6A—C5A—C4A | 120.0 | C23A—C22A—C21A | 120.0 |
C6A—C5A—H5A | 120.0 | C23A—C22A—H22A | 120.0 |
C4A—C5A—H5A | 120.0 | C21A—C22A—H22A | 120.0 |
C5A—C6A—C1A | 120.0 | C22A—C23A—C18A | 120.0 |
C5A—C6A—H6A | 120.0 | C22A—C23A—H23A | 120.0 |
C1A—C6A—H6A | 120.0 | C18A—C23A—H23A | 120.0 |
N1—C7—C8 | 114.2 (13) | N3—C24—C25 | 111.9 (14) |
N1—C7—H7A | 108.7 | N3—C24—H24A | 109.2 |
C8—C7—H7A | 108.7 | C25—C24—H24A | 109.2 |
N1—C7—H7B | 108.7 | N3—C24—H24B | 109.2 |
C8—C7—H7B | 108.7 | C25—C24—H24B | 109.2 |
H7A—C7—H7B | 107.6 | H24A—C24—H24B | 107.9 |
N2—C8—C7 | 111.8 (13) | N4—C25—C24 | 111.5 (12) |
N2—C8—H8A | 109.3 | N4—C25—H25A | 109.3 |
C7—C8—H8A | 109.3 | C24—C25—H25A | 109.3 |
N2—C8—H8B | 109.3 | N4—C25—H25B | 109.3 |
C7—C8—H8B | 109.3 | C24—C25—H25B | 109.3 |
H8A—C8—H8B | 107.9 | H25A—C25—H25B | 108.0 |
N2—C9—C10 | 110.8 (12) | N4—C26—C27 | 110.5 (13) |
N2—C9—H9A | 109.5 | N4—C26—H26A | 109.6 |
C10—C9—H9A | 109.5 | C27—C26—H26A | 109.6 |
N2—C9—H9B | 109.5 | N4—C26—H26B | 109.6 |
C10—C9—H9B | 109.5 | C27—C26—H26B | 109.6 |
H9A—C9—H9B | 108.1 | H26A—C26—H26B | 108.1 |
N1—C10—C9 | 112.7 (13) | N3—C27—C26 | 113.3 (13) |
N1—C10—H10A | 109.1 | N3—C27—H27A | 108.9 |
C9—C10—H10A | 109.1 | C26—C27—H27A | 108.9 |
N1—C10—H10B | 109.1 | N3—C27—H27B | 108.9 |
C9—C10—H10B | 109.1 | C26—C27—H27B | 108.9 |
H10A—C10—H10B | 107.8 | H27A—C27—H27B | 107.7 |
O2—S1—O3 | 114.3 (10) | O5—S2—O6 | 112.7 (8) |
O2—S1—O1 | 113.6 (8) | O5—S2—O4 | 116.2 (9) |
O3—S1—O1 | 111.2 (8) | O6—S2—O4 | 110.6 (8) |
O2—S1—C11 | 106.6 (7) | O5—S2—C28 | 106.9 (8) |
O3—S1—C11 | 105.8 (7) | O6—S2—C28 | 105.0 (7) |
O1—S1—C11 | 104.5 (7) | O4—S2—C28 | 104.5 (7) |
C16—C11—C12 | 115.3 (15) | C29—C28—C33 | 116.1 (14) |
C16—C11—S1 | 123.0 (12) | C29—C28—S2 | 123.0 (12) |
C12—C11—S1 | 121.3 (12) | C33—C28—S2 | 120.7 (12) |
C13—C12—C11 | 119.8 (17) | C28—C29—C30 | 123.4 (16) |
C13—C12—H12 | 120.1 | C28—C29—H29 | 118.3 |
C11—C12—H12 | 120.1 | C30—C29—H29 | 118.3 |
C14—C13—C12 | 124.9 (19) | C29—C30—C31 | 122.3 (18) |
C14—C13—H13 | 117.5 | C29—C30—H30 | 118.9 |
C12—C13—H13 | 117.5 | C31—C30—H30 | 118.9 |
C13—C14—C15 | 115.2 (19) | C30—C31—C32 | 115.3 (19) |
C13—C14—C17 | 124 (2) | C30—C31—C34 | 123 (2) |
C15—C14—C17 | 120 (2) | C32—C31—C34 | 121 (2) |
C16—C15—C14 | 121.0 (18) | C31—C32—C33 | 123.4 (18) |
C16—C15—H15 | 119.5 | C31—C32—H32 | 118.3 |
C14—C15—H15 | 119.5 | C33—C32—H32 | 118.3 |
C11—C16—C15 | 123.5 (17) | C32—C33—C28 | 119.5 (16) |
C11—C16—H16 | 118.3 | C32—C33—H33 | 120.2 |
C15—C16—H16 | 118.3 | C28—C33—H33 | 120.2 |
C14—C17—H17A | 109.5 | C31—C34—H34A | 109.5 |
C14—C17—H17B | 109.5 | C31—C34—H34B | 109.5 |
H17A—C17—H17B | 109.5 | H34A—C34—H34B | 109.5 |
C14—C17—H17C | 109.5 | C31—C34—H34C | 109.5 |
H17A—C17—H17C | 109.5 | H34A—C34—H34C | 109.5 |
H17B—C17—H17C | 109.5 | H34B—C34—H34C | 109.5 |
C7—N1—C1—C2 | −165 (2) | C27—N3—C18—C19 | 163 (2) |
C10—N1—C1—C2 | −26 (3) | C24—N3—C18—C19 | 23 (3) |
C7—N1—C1—C6 | 21 (3) | C27—N3—C18—C23 | −23 (3) |
C10—N1—C1—C6 | 159 (2) | C24—N3—C18—C23 | −162 (2) |
C6—C1—C2—C3 | 0.0 | C23—C18—C19—C20 | 0.0 |
N1—C1—C2—C3 | −174 (3) | N3—C18—C19—C20 | 174 (3) |
C1—C2—C3—C4 | 0.0 | C18—C19—C20—C21 | 0.0 |
C2—C3—C4—C5 | 0.0 | C19—C20—C21—C22 | 0.0 |
C3—C4—C5—C6 | 0.0 | C20—C21—C22—C23 | 0.0 |
C4—C5—C6—C1 | 0.0 | C21—C22—C23—C18 | 0.0 |
C2—C1—C6—C5 | 0.0 | C19—C18—C23—C22 | 0.0 |
N1—C1—C6—C5 | 174 (3) | N3—C18—C23—C22 | −174 (3) |
C7—N1—C1A—C2A | −147 (2) | C27—N3—C18A—C19A | 146 (2) |
C10—N1—C1A—C2A | −8 (3) | C24—N3—C18A—C19A | 6 (3) |
C7—N1—C1A—C6A | 39 (3) | C27—N3—C18A—C23A | −41 (3) |
C10—N1—C1A—C6A | 178 (2) | C24—N3—C18A—C23A | −180 (2) |
C6A—C1A—C2A—C3A | 0.0 | C23A—C18A—C19A—C20A | 0.0 |
N1—C1A—C2A—C3A | −174 (3) | N3—C18A—C19A—C20A | 174 (3) |
C1A—C2A—C3A—C4A | 0.0 | C18A—C19A—C20A—C21A | 0.0 |
C2A—C3A—C4A—C5A | 0.0 | C19A—C20A—C21A—C22A | 0.0 |
C3A—C4A—C5A—C6A | 0.0 | C20A—C21A—C22A—C23A | 0.0 |
C4A—C5A—C6A—C1A | 0.0 | C21A—C22A—C23A—C18A | 0.0 |
C2A—C1A—C6A—C5A | 0.0 | C19A—C18A—C23A—C22A | 0.0 |
N1—C1A—C6A—C5A | 174 (3) | N3—C18A—C23A—C22A | −174 (3) |
C1A—N1—C7—C8 | −168 (2) | C18—N3—C24—C25 | −168.7 (18) |
C1—N1—C7—C8 | −168 (2) | C27—N3—C24—C25 | 51.1 (17) |
C10—N1—C7—C8 | 50.7 (18) | C18A—N3—C24—C25 | −167 (2) |
C9—N2—C8—C7 | 54.6 (17) | C26—N4—C25—C24 | 57.4 (16) |
N1—C7—C8—N2 | −52.8 (19) | N3—C24—C25—N4 | −54.9 (17) |
C8—N2—C9—C10 | −55.4 (17) | C25—N4—C26—C27 | −56.2 (16) |
C1A—N1—C10—C9 | 167 (2) | C18—N3—C27—C26 | 167.3 (19) |
C1—N1—C10—C9 | 169 (2) | C18A—N3—C27—C26 | 169 (2) |
C7—N1—C10—C9 | −51.2 (17) | C24—N3—C27—C26 | −51.3 (19) |
N2—C9—C10—N1 | 54.4 (18) | N4—C26—C27—N3 | 53.6 (19) |
O2—S1—C11—C16 | 171.6 (14) | O5—S2—C28—C29 | −168.7 (13) |
O3—S1—C11—C16 | −66.3 (15) | O6—S2—C28—C29 | −48.8 (14) |
O1—S1—C11—C16 | 51.1 (15) | O4—S2—C28—C29 | 67.7 (14) |
O2—S1—C11—C12 | −16.1 (15) | O5—S2—C28—C33 | 15.2 (14) |
O3—S1—C11—C12 | 105.9 (14) | O6—S2—C28—C33 | 135.1 (12) |
O1—S1—C11—C12 | −136.7 (13) | O4—S2—C28—C33 | −108.5 (13) |
C16—C11—C12—C13 | −5 (2) | C33—C28—C29—C30 | −3 (2) |
S1—C11—C12—C13 | −178.3 (14) | S2—C28—C29—C30 | −178.9 (14) |
C11—C12—C13—C14 | 2 (3) | C28—C29—C30—C31 | 1 (3) |
C12—C13—C14—C15 | 2 (3) | C29—C30—C31—C32 | 1 (3) |
C12—C13—C14—C17 | 180 (2) | C29—C30—C31—C34 | −179.4 (19) |
C13—C14—C15—C16 | −2 (3) | C30—C31—C32—C33 | −1 (3) |
C17—C14—C15—C16 | −179.9 (19) | C34—C31—C32—C33 | 178.8 (19) |
C12—C11—C16—C15 | 6 (3) | C31—C32—C33—C28 | 0 (3) |
S1—C11—C16—C15 | 178.4 (15) | C29—C28—C33—C32 | 2 (2) |
C14—C15—C16—C11 | −2 (3) | S2—C28—C33—C32 | 178.3 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21N···O6 | 0.89 | 2.07 | 2.884 (18) | 151 |
N2—H22N···O4i | 0.89 | 1.92 | 2.774 (17) | 161 |
C9—H9B···O1ii | 0.97 | 2.64 | 3.534 (19) | 154 |
N4—H41N···O3ii | 0.89 | 1.92 | 2.788 (16) | 163 |
N4—H42N···O1 | 0.89 | 2.09 | 2.890 (18) | 149 |
N4—H42N···O5 | 0.89 | 2.43 | 2.865 (18) | 111 |
C25—H25A···O6iii | 0.97 | 2.63 | 3.520 (18) | 153 |
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x, y−1/2, −z; (iii) −x+1, y+1/2, −z. |
C10H15N2+·C4H5O6−·H2O | Dx = 1.367 Mg m−3 |
Mr = 330.33 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 3790 reflections |
a = 7.1185 (7) Å | θ = 2.9–27.8° |
b = 7.5255 (8) Å | µ = 0.11 mm−1 |
c = 29.955 (3) Å | T = 293 K |
V = 1604.7 (3) Å3 | Prism, colourless |
Z = 4 | 0.42 × 0.32 × 0.24 mm |
F(000) = 704 |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 2808 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.019 |
Rotation method data acquisition using ω scans. | θmax = 27.8°, θmin = 2.9° |
Absorption correction: multi-scan (CrysalisRED; Oxford Diffraction, 2007) | h = −9→9 |
Tmin = 0.883, Tmax = 1.000 | k = −6→9 |
6773 measured reflections | l = −36→38 |
3354 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0359P)2 + 0.5036P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
3354 reflections | Δρmax = 0.20 e Å−3 |
260 parameters | Δρmin = −0.16 e Å−3 |
211 restraints | Absolute structure: Flack x determined using 912 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: dual | Absolute structure parameter: −0.2 (5) |
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) | |
N1 | 0.2138 (4) | 0.3376 (4) | 0.69293 (7) | 0.0428 (6) | |
N2 | 0.0481 (4) | 0.3028 (5) | 0.60649 (9) | 0.0515 (8) | |
H21 | 0.057 (6) | 0.189 (3) | 0.6004 (13) | 0.062* | |
H22 | −0.007 (5) | 0.338 (5) | 0.5825 (9) | 0.062* | |
C1 | 0.3025 (8) | 0.3071 (7) | 0.7352 (2) | 0.0393 (16) | 0.611 (13) |
C2 | 0.4926 (8) | 0.2687 (11) | 0.73967 (16) | 0.0489 (16) | 0.611 (13) |
H2 | 0.566167 | 0.250879 | 0.714417 | 0.059* | 0.611 (13) |
C3 | 0.5726 (8) | 0.2568 (12) | 0.78189 (19) | 0.0596 (18) | 0.611 (13) |
H3 | 0.699769 | 0.231094 | 0.784885 | 0.071* | 0.611 (13) |
C4 | 0.4626 (12) | 0.2834 (8) | 0.81965 (16) | 0.0629 (19) | 0.611 (13) |
H4 | 0.516140 | 0.275436 | 0.847893 | 0.076* | 0.611 (13) |
C5 | 0.2725 (11) | 0.3218 (11) | 0.8152 (2) | 0.0565 (19) | 0.611 (13) |
H5 | 0.198908 | 0.339564 | 0.840434 | 0.068* | 0.611 (13) |
C6 | 0.1925 (8) | 0.3336 (10) | 0.7730 (3) | 0.0469 (17) | 0.611 (13) |
H6 | 0.065303 | 0.359351 | 0.769967 | 0.056* | 0.611 (13) |
C1A | 0.3005 (14) | 0.3277 (13) | 0.7366 (4) | 0.044 (2) | 0.389 (13) |
C2A | 0.4913 (13) | 0.3634 (19) | 0.7408 (3) | 0.054 (2) | 0.389 (13) |
H2A | 0.561166 | 0.395753 | 0.715828 | 0.065* | 0.389 (13) |
C3A | 0.5777 (13) | 0.3508 (18) | 0.7823 (3) | 0.058 (2) | 0.389 (13) |
H3A | 0.705291 | 0.374729 | 0.785092 | 0.069* | 0.389 (13) |
C4A | 0.4732 (18) | 0.3026 (13) | 0.8196 (3) | 0.060 (3) | 0.389 (13) |
H4A | 0.531021 | 0.294126 | 0.847328 | 0.073* | 0.389 (13) |
C5A | 0.2825 (18) | 0.2669 (16) | 0.8154 (4) | 0.052 (2) | 0.389 (13) |
H5A | 0.212626 | 0.234547 | 0.840300 | 0.062* | 0.389 (13) |
C6A | 0.1961 (13) | 0.2795 (15) | 0.7739 (5) | 0.044 (2) | 0.389 (13) |
H6A | 0.068497 | 0.255570 | 0.771037 | 0.053* | 0.389 (13) |
C7 | 0.0322 (4) | 0.2513 (6) | 0.68665 (10) | 0.0600 (10) | |
H7A | −0.044378 | 0.269546 | 0.713032 | 0.072* | |
H7B | 0.051046 | 0.124480 | 0.683019 | 0.072* | |
C8 | −0.0694 (5) | 0.3230 (6) | 0.64654 (11) | 0.0615 (11) | |
H8A | −0.186632 | 0.259277 | 0.642510 | 0.074* | |
H8B | −0.098445 | 0.447573 | 0.651123 | 0.074* | |
C9 | 0.2345 (5) | 0.3864 (6) | 0.61270 (11) | 0.0626 (11) | |
H9A | 0.219400 | 0.513976 | 0.615495 | 0.075* | |
H9B | 0.311852 | 0.363336 | 0.586672 | 0.075* | |
C10 | 0.3310 (4) | 0.3153 (6) | 0.65361 (9) | 0.0516 (9) | |
H10A | 0.358743 | 0.190224 | 0.649445 | 0.062* | |
H10B | 0.448994 | 0.377545 | 0.657941 | 0.062* | |
O1 | 0.3807 (3) | 0.8465 (3) | 0.42742 (7) | 0.0391 (5) | |
O2 | 0.0905 (3) | 0.9424 (3) | 0.44164 (9) | 0.0536 (6) | |
O3 | −0.0601 (3) | 0.6256 (3) | 0.44303 (8) | 0.0403 (5) | |
H3O | −0.097 (5) | 0.721 (3) | 0.4540 (10) | 0.048* | |
O4 | 0.1952 (3) | 0.6293 (3) | 0.51830 (6) | 0.0405 (5) | |
H4O | 0.091 (3) | 0.613 (5) | 0.5267 (11) | 0.049* | |
O5 | 0.0826 (3) | 0.2841 (3) | 0.51284 (7) | 0.0513 (6) | |
O6 | 0.1893 (3) | 0.2612 (2) | 0.44300 (6) | 0.0369 (5) | |
H6O | 0.153 (4) | 0.156 (3) | 0.4444 (11) | 0.044* | |
C11 | 0.2097 (4) | 0.8232 (3) | 0.43575 (9) | 0.0323 (6) | |
C12 | 0.1380 (3) | 0.6322 (3) | 0.43867 (9) | 0.0277 (5) | |
H12 | 0.173538 | 0.569709 | 0.411225 | 0.033* | |
C13 | 0.2286 (4) | 0.5366 (3) | 0.47836 (8) | 0.0284 (6) | |
H13 | 0.364670 | 0.533612 | 0.473374 | 0.034* | |
C14 | 0.1588 (4) | 0.3466 (4) | 0.48051 (8) | 0.0311 (6) | |
O7 | −0.3916 (4) | 0.5658 (4) | 0.39633 (9) | 0.0629 (7) | |
H71O | −0.286 (4) | 0.586 (6) | 0.4077 (13) | 0.075* | |
H72O | −0.462 (5) | 0.649 (4) | 0.4054 (14) | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0367 (13) | 0.0643 (16) | 0.0275 (11) | −0.0036 (13) | −0.0040 (10) | 0.0023 (12) |
N2 | 0.0418 (14) | 0.083 (2) | 0.0299 (13) | −0.0080 (17) | −0.0080 (11) | 0.0064 (15) |
C1 | 0.042 (3) | 0.047 (3) | 0.029 (3) | 0.000 (3) | −0.004 (3) | −0.009 (3) |
C2 | 0.044 (3) | 0.067 (4) | 0.037 (2) | 0.012 (3) | −0.003 (2) | 0.001 (3) |
C3 | 0.056 (3) | 0.075 (5) | 0.048 (3) | 0.012 (4) | −0.017 (2) | 0.003 (4) |
C4 | 0.074 (4) | 0.079 (4) | 0.036 (3) | 0.007 (4) | −0.016 (3) | 0.002 (3) |
C5 | 0.067 (3) | 0.069 (5) | 0.033 (3) | 0.005 (4) | −0.002 (3) | −0.002 (3) |
C6 | 0.048 (3) | 0.056 (4) | 0.037 (3) | 0.009 (3) | −0.002 (2) | −0.005 (3) |
C1A | 0.044 (4) | 0.051 (5) | 0.036 (4) | 0.003 (4) | −0.005 (4) | 0.010 (4) |
C2A | 0.050 (4) | 0.072 (5) | 0.039 (4) | −0.001 (5) | −0.003 (3) | 0.006 (4) |
C3A | 0.052 (4) | 0.078 (6) | 0.043 (4) | 0.000 (5) | −0.016 (3) | −0.001 (5) |
C4A | 0.068 (5) | 0.078 (5) | 0.036 (4) | 0.001 (5) | −0.017 (4) | −0.002 (4) |
C5A | 0.065 (4) | 0.058 (5) | 0.032 (4) | 0.005 (4) | 0.001 (4) | 0.001 (4) |
C6A | 0.048 (4) | 0.048 (5) | 0.036 (4) | 0.002 (4) | −0.001 (3) | 0.003 (4) |
C7 | 0.0388 (17) | 0.108 (3) | 0.0335 (16) | −0.015 (2) | 0.0016 (13) | 0.0005 (19) |
C8 | 0.0405 (18) | 0.101 (3) | 0.0431 (18) | 0.007 (2) | −0.0058 (14) | −0.010 (2) |
C9 | 0.051 (2) | 0.097 (3) | 0.0398 (17) | −0.023 (2) | −0.0084 (15) | 0.0173 (19) |
C10 | 0.0357 (16) | 0.085 (3) | 0.0343 (15) | −0.0079 (18) | −0.0012 (12) | 0.0073 (17) |
O1 | 0.0305 (10) | 0.0412 (11) | 0.0458 (11) | −0.0059 (9) | 0.0039 (9) | −0.0013 (10) |
O2 | 0.0379 (12) | 0.0274 (10) | 0.0954 (18) | 0.0020 (9) | 0.0058 (12) | −0.0045 (12) |
O3 | 0.0255 (10) | 0.0319 (10) | 0.0635 (14) | −0.0007 (9) | −0.0047 (10) | −0.0087 (11) |
O4 | 0.0355 (11) | 0.0538 (12) | 0.0323 (10) | −0.0080 (11) | 0.0028 (9) | −0.0162 (10) |
O5 | 0.0641 (15) | 0.0544 (13) | 0.0354 (11) | −0.0131 (12) | 0.0138 (10) | 0.0052 (10) |
O6 | 0.0472 (12) | 0.0257 (9) | 0.0379 (10) | −0.0018 (9) | 0.0084 (9) | −0.0025 (9) |
C11 | 0.0325 (14) | 0.0308 (14) | 0.0336 (14) | −0.0019 (13) | −0.0026 (12) | −0.0016 (12) |
C12 | 0.0231 (12) | 0.0276 (13) | 0.0326 (13) | 0.0017 (11) | −0.0013 (11) | −0.0044 (12) |
C13 | 0.0249 (13) | 0.0353 (14) | 0.0248 (12) | −0.0001 (12) | 0.0015 (11) | −0.0045 (11) |
C14 | 0.0291 (14) | 0.0349 (14) | 0.0293 (13) | 0.0013 (12) | 0.0002 (11) | 0.0009 (12) |
O7 | 0.0411 (13) | 0.0784 (19) | 0.0691 (16) | 0.0049 (14) | −0.0092 (12) | −0.0320 (15) |
N1—C1 | 1.434 (6) | C5A—H5A | 0.9300 |
N1—C1A | 1.448 (9) | C6A—H6A | 0.9300 |
N1—C10 | 1.453 (4) | C7—C8 | 1.502 (5) |
N1—C7 | 1.459 (4) | C7—H7A | 0.9700 |
N2—C8 | 1.470 (4) | C7—H7B | 0.9700 |
N2—C9 | 1.480 (4) | C8—H8A | 0.9700 |
N2—H21 | 0.88 (2) | C8—H8B | 0.9700 |
N2—H22 | 0.86 (2) | C9—C10 | 1.503 (4) |
C1—C2 | 1.3900 | C9—H9A | 0.9700 |
C1—C6 | 1.3900 | C9—H9B | 0.9700 |
C2—C3 | 1.3900 | C10—H10A | 0.9700 |
C2—H2 | 0.9300 | C10—H10B | 0.9700 |
C3—C4 | 1.3900 | O1—C11 | 1.255 (3) |
C3—H3 | 0.9300 | O2—C11 | 1.247 (3) |
C4—C5 | 1.3900 | O3—C12 | 1.417 (3) |
C4—H4 | 0.9300 | O3—H3O | 0.83 (2) |
C5—C6 | 1.3900 | O4—C13 | 1.405 (3) |
C5—H5 | 0.9300 | O4—H4O | 0.79 (2) |
C6—H6 | 0.9300 | O5—C14 | 1.205 (3) |
C1A—C2A | 1.3900 | O6—C14 | 1.312 (3) |
C1A—C6A | 1.3900 | O6—H6O | 0.83 (2) |
C2A—C3A | 1.3900 | C11—C12 | 1.528 (4) |
C2A—H2A | 0.9300 | C12—C13 | 1.532 (4) |
C3A—C4A | 1.3900 | C12—H12 | 0.9800 |
C3A—H3A | 0.9300 | C13—C14 | 1.516 (4) |
C4A—C5A | 1.3900 | C13—H13 | 0.9800 |
C4A—H4A | 0.9300 | O7—H71O | 0.84 (2) |
C5A—C6A | 1.3900 | O7—H72O | 0.85 (2) |
C1—N1—C10 | 116.4 (3) | N1—C7—C8 | 111.7 (3) |
C1A—N1—C10 | 118.8 (5) | N1—C7—H7A | 109.3 |
C1—N1—C7 | 115.6 (3) | C8—C7—H7A | 109.3 |
C1A—N1—C7 | 118.1 (5) | N1—C7—H7B | 109.3 |
C10—N1—C7 | 110.7 (2) | C8—C7—H7B | 109.3 |
C8—N2—C9 | 111.3 (3) | H7A—C7—H7B | 107.9 |
C8—N2—H21 | 108 (3) | N2—C8—C7 | 110.0 (3) |
C9—N2—H21 | 112 (3) | N2—C8—H8A | 109.7 |
C8—N2—H22 | 113 (3) | C7—C8—H8A | 109.7 |
C9—N2—H22 | 112 (3) | N2—C8—H8B | 109.7 |
H21—N2—H22 | 99 (4) | C7—C8—H8B | 109.7 |
C2—C1—C6 | 120.0 | H8A—C8—H8B | 108.2 |
C2—C1—N1 | 123.2 (5) | N2—C9—C10 | 111.2 (3) |
C6—C1—N1 | 116.6 (5) | N2—C9—H9A | 109.4 |
C1—C2—C3 | 120.0 | C10—C9—H9A | 109.4 |
C1—C2—H2 | 120.0 | N2—C9—H9B | 109.4 |
C3—C2—H2 | 120.0 | C10—C9—H9B | 109.4 |
C4—C3—C2 | 120.0 | H9A—C9—H9B | 108.0 |
C4—C3—H3 | 120.0 | N1—C10—C9 | 110.9 (3) |
C2—C3—H3 | 120.0 | N1—C10—H10A | 109.5 |
C3—C4—C5 | 120.0 | C9—C10—H10A | 109.5 |
C3—C4—H4 | 120.0 | N1—C10—H10B | 109.5 |
C5—C4—H4 | 120.0 | C9—C10—H10B | 109.5 |
C4—C5—C6 | 120.0 | H10A—C10—H10B | 108.0 |
C4—C5—H5 | 120.0 | C12—O3—H3O | 109 (2) |
C6—C5—H5 | 120.0 | C13—O4—H4O | 111 (3) |
C5—C6—C1 | 120.0 | C14—O6—H6O | 112 (2) |
C5—C6—H6 | 120.0 | O2—C11—O1 | 126.0 (3) |
C1—C6—H6 | 120.0 | O2—C11—C12 | 116.2 (2) |
C2A—C1A—C6A | 120.0 | O1—C11—C12 | 117.8 (2) |
C2A—C1A—N1 | 119.3 (7) | O3—C12—C11 | 111.7 (2) |
C6A—C1A—N1 | 120.7 (7) | O3—C12—C13 | 109.3 (2) |
C1A—C2A—C3A | 120.0 | C11—C12—C13 | 110.2 (2) |
C1A—C2A—H2A | 120.0 | O3—C12—H12 | 108.5 |
C3A—C2A—H2A | 120.0 | C11—C12—H12 | 108.5 |
C4A—C3A—C2A | 120.0 | C13—C12—H12 | 108.5 |
C4A—C3A—H3A | 120.0 | O4—C13—C14 | 112.1 (2) |
C2A—C3A—H3A | 120.0 | O4—C13—C12 | 110.9 (2) |
C3A—C4A—C5A | 120.0 | C14—C13—C12 | 109.7 (2) |
C3A—C4A—H4A | 120.0 | O4—C13—H13 | 108.0 |
C5A—C4A—H4A | 120.0 | C14—C13—H13 | 108.0 |
C4A—C5A—C6A | 120.0 | C12—C13—H13 | 108.0 |
C4A—C5A—H5A | 120.0 | O5—C14—O6 | 124.9 (3) |
C6A—C5A—H5A | 120.0 | O5—C14—C13 | 123.3 (2) |
C5A—C6A—C1A | 120.0 | O6—C14—C13 | 111.8 (2) |
C5A—C6A—H6A | 120.0 | H71O—O7—H72O | 105 (4) |
C1A—C6A—H6A | 120.0 | ||
C10—N1—C1—C2 | 3.8 (6) | N1—C1A—C6A—C5A | 178.6 (8) |
C7—N1—C1—C2 | 136.3 (5) | C1—N1—C7—C8 | 166.9 (4) |
C10—N1—C1—C6 | 178.1 (4) | C1A—N1—C7—C8 | 160.3 (5) |
C7—N1—C1—C6 | −49.5 (5) | C10—N1—C7—C8 | −58.0 (4) |
C6—C1—C2—C3 | 0.0 | C9—N2—C8—C7 | −54.9 (5) |
N1—C1—C2—C3 | 174.0 (5) | N1—C7—C8—N2 | 56.7 (5) |
C1—C2—C3—C4 | 0.0 | C8—N2—C9—C10 | 54.9 (5) |
C2—C3—C4—C5 | 0.0 | C1—N1—C10—C9 | −168.4 (4) |
C3—C4—C5—C6 | 0.0 | C1A—N1—C10—C9 | −161.7 (5) |
C4—C5—C6—C1 | 0.0 | C7—N1—C10—C9 | 56.8 (4) |
C2—C1—C6—C5 | 0.0 | N2—C9—C10—N1 | −55.5 (4) |
N1—C1—C6—C5 | −174.4 (5) | O2—C11—C12—O3 | 6.3 (3) |
C10—N1—C1A—C2A | 23.7 (8) | O1—C11—C12—O3 | −173.2 (2) |
C7—N1—C1A—C2A | 162.3 (6) | O2—C11—C12—C13 | −115.4 (3) |
C10—N1—C1A—C6A | −154.9 (6) | O1—C11—C12—C13 | 65.1 (3) |
C7—N1—C1A—C6A | −16.3 (9) | O3—C12—C13—O4 | −66.8 (3) |
C6A—C1A—C2A—C3A | 0.0 | C11—C12—C13—O4 | 56.4 (3) |
N1—C1A—C2A—C3A | −178.6 (8) | O3—C12—C13—C14 | 57.7 (3) |
C1A—C2A—C3A—C4A | 0.0 | C11—C12—C13—C14 | −179.2 (2) |
C2A—C3A—C4A—C5A | 0.0 | O4—C13—C14—O5 | 0.4 (4) |
C3A—C4A—C5A—C6A | 0.0 | C12—C13—C14—O5 | −123.3 (3) |
C4A—C5A—C6A—C1A | 0.0 | O4—C13—C14—O6 | 179.5 (2) |
C2A—C1A—C6A—C5A | 0.0 | C12—C13—C14—O6 | 55.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O7i | 0.88 (2) | 1.95 (2) | 2.808 (5) | 164 (4) |
N2—H22···O1ii | 0.86 (2) | 2.52 (3) | 3.069 (4) | 122 (3) |
N2—H22···O5 | 0.86 (2) | 2.22 (3) | 2.820 (3) | 127 (3) |
N2—H22···O6iii | 0.86 (2) | 2.41 (3) | 2.992 (3) | 125 (3) |
C9—H9B···O2iv | 0.97 | 2.61 | 3.276 (4) | 126 |
O3—H3O···O2 | 0.83 (2) | 2.17 (3) | 2.614 (3) | 114 (3) |
O3—H3O···O4ii | 0.83 (2) | 2.04 (2) | 2.789 (3) | 150 (3) |
O4—H4O···O1ii | 0.79 (2) | 2.06 (3) | 2.773 (3) | 151 (3) |
O6—H6O···O2v | 0.83 (2) | 1.67 (2) | 2.501 (3) | 174 (3) |
O7—H71O···O3 | 0.84 (2) | 1.95 (2) | 2.780 (3) | 171 (4) |
O7—H72O···O1vi | 0.85 (2) | 1.97 (2) | 2.821 (3) | 178 (4) |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x−1/2, −y+3/2, −z+1; (iii) x−1/2, −y+1/2, −z+1; (iv) x+1/2, −y+3/2, −z+1; (v) x, y−1, z; (vi) x−1, y, z. |
C10H15N2+·C4H3O4− | Dx = 1.287 Mg m−3 |
Mr = 278.30 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 6248 reflections |
a = 26.702 (1) Å | θ = 2.7–27.8° |
b = 7.9626 (3) Å | µ = 0.10 mm−1 |
c = 6.7571 (3) Å | T = 293 K |
V = 1436.68 (10) Å3 | Prism, light brown |
Z = 4 | 0.48 × 0.44 × 0.40 mm |
F(000) = 592 |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 2770 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.018 |
Rotation method data acquisition using ω scans. | θmax = 27.9°, θmin = 3.0° |
Absorption correction: multi-scan (CrysalisRED; Oxford Diffraction, 2007) | h = −33→33 |
Tmin = 0.894, Tmax = 1.000 | k = −10→5 |
9534 measured reflections | l = −8→8 |
3127 independent reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0296P)2 + 0.3161P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.077 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.17 e Å−3 |
3127 reflections | Δρmin = −0.13 e Å−3 |
191 parameters | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
4 restraints | Extinction coefficient: 0.024 (5) |
Primary atom site location: dual | Absolute structure: Flack x determined using 1130 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.3 (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 | ||
N1 | 0.07139 (6) | 0.0974 (2) | 0.4560 (3) | 0.0396 (4) | |
N2 | 0.15289 (7) | 0.1889 (2) | 0.2018 (3) | 0.0359 (4) | |
H21 | 0.1639 (9) | 0.258 (3) | 0.111 (3) | 0.043* | |
H22 | 0.1758 (8) | 0.112 (3) | 0.231 (4) | 0.043* | |
C1 | 0.02675 (7) | 0.1920 (3) | 0.4495 (3) | 0.0341 (5) | |
C2 | −0.01118 (8) | 0.1565 (3) | 0.3155 (4) | 0.0460 (5) | |
H2 | −0.006524 | 0.072842 | 0.221209 | 0.055* | |
C3 | −0.05581 (9) | 0.2442 (3) | 0.3210 (5) | 0.0554 (6) | |
H3 | −0.080837 | 0.217775 | 0.230469 | 0.066* | |
C4 | −0.06407 (10) | 0.3685 (3) | 0.4555 (5) | 0.0581 (8) | |
H4 | −0.094144 | 0.427343 | 0.457231 | 0.070* | |
C5 | −0.02681 (11) | 0.4041 (4) | 0.5880 (5) | 0.0605 (8) | |
H5 | −0.031873 | 0.488166 | 0.681492 | 0.073* | |
C6 | 0.01794 (9) | 0.3187 (3) | 0.5862 (4) | 0.0493 (6) | |
H6 | 0.042619 | 0.346194 | 0.677785 | 0.059* | |
C7 | 0.11662 (9) | 0.1763 (4) | 0.5335 (4) | 0.0516 (7) | |
H7A | 0.140074 | 0.089729 | 0.573846 | 0.062* | |
H7B | 0.108145 | 0.242129 | 0.649545 | 0.062* | |
C8 | 0.14116 (9) | 0.2881 (3) | 0.3825 (4) | 0.0453 (6) | |
H8A | 0.118887 | 0.380029 | 0.348976 | 0.054* | |
H8B | 0.171722 | 0.335098 | 0.436782 | 0.054* | |
C9 | 0.10846 (8) | 0.0982 (3) | 0.1241 (3) | 0.0406 (5) | |
H9A | 0.118462 | 0.025512 | 0.015935 | 0.049* | |
H9B | 0.084244 | 0.178364 | 0.073747 | 0.049* | |
C10 | 0.08503 (8) | −0.0048 (3) | 0.2859 (4) | 0.0458 (6) | |
H10A | 0.055321 | −0.060037 | 0.234969 | 0.055* | |
H10B | 0.108400 | −0.091175 | 0.327448 | 0.055* | |
O1 | 0.28279 (5) | 0.92767 (16) | −0.2019 (3) | 0.0457 (4) | |
O2 | 0.20615 (5) | 1.03469 (16) | −0.1699 (3) | 0.0403 (4) | |
H2O | 0.2217 (8) | 1.136 (3) | −0.190 (4) | 0.048* | |
O3 | 0.24248 (5) | 0.31442 (15) | −0.2281 (3) | 0.0395 (4) | |
O4 | 0.17409 (5) | 0.41963 (17) | −0.0874 (3) | 0.0411 (4) | |
C11 | 0.23766 (7) | 0.9127 (2) | −0.1764 (3) | 0.0298 (4) | |
C12 | 0.21444 (7) | 0.7446 (2) | −0.1522 (4) | 0.0324 (5) | |
H12 | 0.181218 | 0.738436 | −0.111463 | 0.039* | |
C13 | 0.23863 (7) | 0.6049 (2) | −0.1857 (3) | 0.0297 (4) | |
H13 | 0.271921 | 0.611739 | −0.225248 | 0.036* | |
C14 | 0.21578 (7) | 0.4351 (2) | −0.1639 (3) | 0.0283 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0316 (9) | 0.0426 (10) | 0.0447 (11) | 0.0009 (8) | 0.0062 (8) | 0.0066 (9) |
N2 | 0.0258 (9) | 0.0317 (9) | 0.0504 (12) | 0.0015 (7) | 0.0070 (8) | 0.0071 (9) |
C1 | 0.0292 (10) | 0.0343 (10) | 0.0389 (11) | −0.0044 (8) | 0.0063 (9) | 0.0047 (10) |
C2 | 0.0385 (11) | 0.0495 (12) | 0.0502 (14) | −0.0029 (10) | 0.0001 (12) | −0.0091 (13) |
C3 | 0.0355 (11) | 0.0636 (15) | 0.0670 (17) | −0.0042 (11) | −0.0095 (14) | 0.0038 (16) |
C4 | 0.0364 (13) | 0.0466 (14) | 0.091 (2) | 0.0085 (11) | 0.0081 (15) | 0.0066 (16) |
C5 | 0.0538 (16) | 0.0474 (15) | 0.080 (2) | 0.0057 (12) | 0.0095 (15) | −0.0165 (15) |
C6 | 0.0423 (13) | 0.0489 (14) | 0.0567 (16) | −0.0027 (11) | −0.0030 (12) | −0.0138 (13) |
C7 | 0.0339 (13) | 0.0817 (19) | 0.0391 (13) | 0.0062 (13) | −0.0057 (10) | 0.0027 (14) |
C8 | 0.0279 (10) | 0.0477 (13) | 0.0604 (16) | −0.0049 (10) | −0.0010 (10) | −0.0136 (12) |
C9 | 0.0338 (12) | 0.0459 (13) | 0.0419 (13) | −0.0004 (10) | 0.0034 (10) | −0.0075 (11) |
C10 | 0.0368 (11) | 0.0295 (10) | 0.0709 (17) | −0.0033 (9) | 0.0130 (12) | −0.0028 (12) |
O1 | 0.0309 (7) | 0.0259 (7) | 0.0802 (13) | −0.0035 (6) | 0.0087 (9) | 0.0026 (9) |
O2 | 0.0367 (7) | 0.0188 (6) | 0.0654 (11) | 0.0011 (6) | 0.0051 (8) | 0.0038 (8) |
O3 | 0.0374 (8) | 0.0208 (6) | 0.0604 (11) | 0.0016 (6) | 0.0103 (7) | −0.0015 (7) |
O4 | 0.0305 (8) | 0.0258 (7) | 0.0671 (11) | 0.0008 (6) | 0.0107 (7) | 0.0088 (7) |
C11 | 0.0332 (10) | 0.0224 (9) | 0.0338 (11) | −0.0009 (7) | 0.0011 (9) | 0.0004 (9) |
C12 | 0.0297 (9) | 0.0231 (8) | 0.0443 (12) | −0.0037 (8) | 0.0045 (9) | 0.0019 (9) |
C13 | 0.0297 (9) | 0.0224 (8) | 0.0369 (11) | −0.0028 (7) | 0.0024 (9) | 0.0029 (9) |
C14 | 0.0283 (9) | 0.0201 (8) | 0.0365 (10) | 0.0003 (7) | −0.0024 (9) | 0.0033 (9) |
N1—C1 | 1.411 (3) | C7—H7A | 0.9700 |
N1—C10 | 1.455 (3) | C7—H7B | 0.9700 |
N1—C7 | 1.459 (3) | C8—H8A | 0.9700 |
N2—C9 | 1.485 (3) | C8—H8B | 0.9700 |
N2—C8 | 1.487 (3) | C9—C10 | 1.504 (3) |
N2—H21 | 0.87 (2) | C9—H9A | 0.9700 |
N2—H22 | 0.89 (2) | C9—H9B | 0.9700 |
C1—C2 | 1.388 (3) | C10—H10A | 0.9700 |
C1—C6 | 1.388 (3) | C10—H10B | 0.9700 |
C2—C3 | 1.382 (3) | O1—C11 | 1.223 (2) |
C2—H2 | 0.9300 | O2—C11 | 1.286 (2) |
C3—C4 | 1.361 (4) | O2—H2O | 0.921 (19) |
C3—H3 | 0.9300 | O3—C14 | 1.273 (2) |
C4—C5 | 1.368 (4) | O4—C14 | 1.234 (2) |
C4—H4 | 0.9300 | C11—C12 | 1.485 (2) |
C5—C6 | 1.375 (4) | C12—C13 | 1.306 (3) |
C5—H5 | 0.9300 | C12—H12 | 0.9300 |
C6—H6 | 0.9300 | C13—C14 | 1.490 (2) |
C7—C8 | 1.505 (4) | C13—H13 | 0.9300 |
C1—N1—C10 | 119.1 (2) | H7A—C7—H7B | 107.9 |
C1—N1—C7 | 118.8 (2) | N2—C8—C7 | 109.53 (19) |
C10—N1—C7 | 108.50 (18) | N2—C8—H8A | 109.8 |
C9—N2—C8 | 112.35 (16) | C7—C8—H8A | 109.8 |
C9—N2—H21 | 109.1 (17) | N2—C8—H8B | 109.8 |
C8—N2—H21 | 108.3 (17) | C7—C8—H8B | 109.8 |
C9—N2—H22 | 107.1 (16) | H8A—C8—H8B | 108.2 |
C8—N2—H22 | 109.1 (17) | N2—C9—C10 | 109.9 (2) |
H21—N2—H22 | 111 (2) | N2—C9—H9A | 109.7 |
C2—C1—C6 | 117.3 (2) | C10—C9—H9A | 109.7 |
C2—C1—N1 | 121.9 (2) | N2—C9—H9B | 109.7 |
C6—C1—N1 | 120.7 (2) | C10—C9—H9B | 109.7 |
C3—C2—C1 | 120.6 (2) | H9A—C9—H9B | 108.2 |
C3—C2—H2 | 119.7 | N1—C10—C9 | 111.91 (17) |
C1—C2—H2 | 119.7 | N1—C10—H10A | 109.2 |
C4—C3—C2 | 121.7 (3) | C9—C10—H10A | 109.2 |
C4—C3—H3 | 119.2 | N1—C10—H10B | 109.2 |
C2—C3—H3 | 119.2 | C9—C10—H10B | 109.2 |
C3—C4—C5 | 118.0 (2) | H10A—C10—H10B | 107.9 |
C3—C4—H4 | 121.0 | C11—O2—H2O | 111.3 (14) |
C5—C4—H4 | 121.0 | O1—C11—O2 | 125.17 (17) |
C4—C5—C6 | 121.6 (3) | O1—C11—C12 | 120.99 (17) |
C4—C5—H5 | 119.2 | O2—C11—C12 | 113.83 (16) |
C6—C5—H5 | 119.2 | C13—C12—C11 | 122.85 (17) |
C5—C6—C1 | 120.8 (2) | C13—C12—H12 | 118.6 |
C5—C6—H6 | 119.6 | C11—C12—H12 | 118.6 |
C1—C6—H6 | 119.6 | C12—C13—C14 | 123.57 (17) |
N1—C7—C8 | 111.8 (2) | C12—C13—H13 | 118.2 |
N1—C7—H7A | 109.3 | C14—C13—H13 | 118.2 |
C8—C7—H7A | 109.3 | O4—C14—O3 | 124.92 (16) |
N1—C7—H7B | 109.3 | O4—C14—C13 | 120.10 (17) |
C8—C7—H7B | 109.3 | O3—C14—C13 | 114.97 (16) |
C10—N1—C1—C2 | 18.6 (3) | C10—N1—C7—C8 | 60.7 (3) |
C7—N1—C1—C2 | 154.6 (2) | C9—N2—C8—C7 | 53.1 (3) |
C10—N1—C1—C6 | −165.3 (2) | N1—C7—C8—N2 | −57.3 (3) |
C7—N1—C1—C6 | −29.3 (3) | C8—N2—C9—C10 | −52.9 (2) |
C6—C1—C2—C3 | −0.4 (4) | C1—N1—C10—C9 | 79.8 (2) |
N1—C1—C2—C3 | 175.8 (2) | C7—N1—C10—C9 | −60.2 (3) |
C1—C2—C3—C4 | 0.5 (4) | N2—C9—C10—N1 | 56.7 (2) |
C2—C3—C4—C5 | −0.5 (4) | O1—C11—C12—C13 | −10.5 (4) |
C3—C4—C5—C6 | 0.4 (5) | O2—C11—C12—C13 | 168.7 (2) |
C4—C5—C6—C1 | −0.3 (5) | C11—C12—C13—C14 | −179.4 (2) |
C2—C1—C6—C5 | 0.3 (4) | C12—C13—C14—O4 | −9.5 (3) |
N1—C1—C6—C5 | −176.0 (3) | C12—C13—C14—O3 | 170.9 (2) |
C1—N1—C7—C8 | −79.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O4 | 0.87 (2) | 1.88 (2) | 2.741 (2) | 168 (2) |
N2—H22···O1i | 0.89 (2) | 1.89 (2) | 2.775 (2) | 172 (2) |
C7—H7A···O2ii | 0.97 | 2.51 | 3.317 (3) | 141 |
C8—H8B···O3iii | 0.97 | 2.55 | 3.203 (3) | 124 |
C9—H9A···O2iv | 0.97 | 2.66 | 3.318 (3) | 126 |
O2—H2O···O3v | 0.92 (2) | 1.54 (2) | 2.4610 (18) | 174 (2) |
Symmetry codes: (i) −x+1/2, y−1, z+1/2; (ii) x, y−1, z+1; (iii) −x+1/2, y, z+1/2; (iv) x, y−1, z; (v) x, y+1, z. |
Acknowledgements
SDA is grateful to the University of Mysore for research facilities. HSY thanks UGC for a BSR Faculty fellowship for three years.
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