research communications
of the of 5-aminoisophthalic acid and 1,2-bis(pyridin-4-yl)ethene
a764 Natural Sciences Complex, Buffalo, 14260-3000, USA, b345 Natural Sciences Complex, Buffalo, 14260-3000, USA, and c771 Natural Sciences Complex, Buffalo, 14260-3000, USA
*Correspondence e-mail: jbb6@buffalo.edu
In the title 1:1 12H10N2·C8H7NO4, the bipyridine moiety shows whole-molecule disorder over two sets of sites in a 0.588 (3): 0.412 (3) ratio. In the crystal, the components form hydrogen-bonded sheets linked by N—H⋯O and O—H⋯N interactions, which stack along the a axis. A comparison to a related and previously published of 5-amino-isophthalic acid and the shorter 4,4′-bipryidine is presented.
CKeywords: crystal structure; 5-aminoisophthalic acid; 5AIA; 1,2-bis(pyridin-4-yl)ethene (BE); co-crystal; hydrogen bonding.
CCDC reference: 1471029
1. Chemical context
5-Amino-isophthalic acid (5AIA) is an emerging secondary building unit for a wide variety of metal–organic frameworks (MOFs). (Zeng et al., 2009; Wang et al., 2011; Cox et al., 2015) This compound is also a convenient precursor for the synthesis of azo-derivatized framework ligands, a key component in the rapidly evolving field of photochromic MOFs. (Brown et al., 2013; Castellanos et al., 2016; Walton et al., 2013; Patel et al., 2014). Similarly, 1,2-bis(pyridin-4-yl)ethene (BE) is also commonly used in MOF synthesis; however, it is routinely used in engineering as well (Kongshaug & Fjellvag, 2003; MacGillivray et al., 2008; Desiraju, 1995) The 5AIA–BE presented herein was produced as part of an undergraduate physical chemistry laboratory experiment developed by Jason Benedict.
Recently, the et al., 2009). Unlike many MOFs in which different length linkers lead to isorecticular structures (Eddaoudi et al., 2002), the 5AIA–BP exhibits several notable similarities and differences when compared to 5AIA–BE. As shown in Figs. 4, 5AIA forms hydrogen bonds with two 5AIA molecules and two BP molecules. The 5AIA–BP interactions and one of the 5AIA–5AIA interactions are similar to those found in 5AIA–BE. The remaining 5AIA–5AIA interaction in 5AIA–BP consists solely of an N(amine)–H⋯OH hydrogen bond, as opposed to the N(amine)—H⋯O=C interaction found in 5AIA–BP. Interestingly, this results in a total of five hydrogen bonds in the 5AIA–BP structure compared to the six hydrogen bonds observed in 5AIA–BE.
structure of 5AIA and 4,4′-bipyridine (BP), a shorter analogue of BE, was reported (Zhang2. Structural commentary
The 5AIA–BE ). Both molecules are effectively planar in the solid state (r.m.s. deviation for 5AIA = 0.155 Å). The BE moiety shows whole molecule disorder over two sets of sites, consistent with a local C2 rotation about the long axis of the molecule. The occupancy of the major and minor components was refined to be 0.588 (3) and 0.412 (3), respectively.
crystallizes with one molecule of 5AIA and one molecule of BE in the (Fig. 13. Supramolecular features
In this structure, the 5AIA molecule forms hydrogen bonds to both itself and the BE moiety, forming extended sheets (Table 1 and Fig. 2). The 5AIA–5AIA interactions consist of N(amine)—H⋯O=C hydrogen bonds where each 5AIA makes two hydrogen bonds with two neighboring 5AIA molecules. The 5AIA–BE interaction consists of an O—H⋯N(pyridyl) hydrogen bond such that each 5AIA makes one hydrogen bond with two neighboring BE molecules. The sheets formed by these interactions stack along the the a axis to produce a layered structure (Fig. 3).
4. Database survey
Recently, the et al., 2009). Unlike many MOFs in which different length linkers lead to isorecticular structures (Eddaoudi et al., 2002), the 5AIA–BP exhibits several notable similarites and differences when compared to 5AIA–BE. As shown in Figs. 4, 5AIA forms hydrogen bonds with two 5AIA molecules and two BP molecules. The 5AIA–BP interactions and one of the 5AIA–5AIA interactions are similar to those found in 5AIA–BE. The remaining 5AIA–5AIA interaction in 5AIA–BP consists solely of an N(amine)—H⋯OH hydrogen bond, as opposed to the N(amine)—H⋯O=C interaction found in 5AIA–BP. Interestingly, this results in a total of five hydrogen bonds in the 5AIA–BP structure compared to the six hydrogen bonds observed in 5AIA–BE.
structure of 5AIA and 4,4′-bipyridine (BP), a shorter analogue of BE, was reported (Zhang5. Synthesis and crystallization
Solid BE (0.0119 g, 6.53 × 10−5 mol) and 5AIA (0.0109 g, 6.02 × 10−5 mol) were added to a 25 ml scintillation vial. To this was added approximately 15 ml of ethyl acetate followed by gentle heating. An additional 2 ml of methanol was added and all remaining solids dissolved. The loosely capped vial was then placed into a dark cabinet. After two weeks, yellow block-shaped crystals of the title compound suitable for single-crystal X-ray diffraction measurements were obtained.
6. Refinement
Crystal data, data collection and structure . Heteroatom hydrogen atoms were located in difference electron-density maps and freely refined. Hydrogen atoms attached to carbon atoms were refined using riding models with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C). The BE was found to be disordered over two sets of sites in a 0.588 (3): 0.412 (3) ratio.
details are summarized in Table 2
|
Supporting information
CCDC reference: 1471029
10.1107/S2056989016005259/hb7561sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016005259/hb7561Isup2.hkl
5-Amino-isophthalic acid (5AIA) is an emerging secondary building unit for a wide variety of metal–organic frameworks (MOFs). (Zeng et al., 2009; Wang et al., 2011; Cox et al., 2015) This compound is also a convenient precursor for the synthesis of azo-derivatized framework ligands, a key component in the rapidly evolving field of photochromic MOFs. (Brown et al., 2013; Castellanos et al., 2016; Walton et al., 2013; Patel et al., 2014). Similarly, 1,2-bis(pyridin-4-yl)ethene (BE) is also commonly used in MOF synthesis; however, it is routinely used in
engineering as well (Kongshaug & Fjellvag, 2003; MacGillivray et al., 2008; Desiraju, 1995) The 5AIA–BE presented herein was produced as part of an undergraduate physical chemistry laboratory experiment developed by Jason Benedict.Recently, the
structure of 5AIA and 4,4'-bipyridine (BP), a shorter analogue of BE, was reported (Zhang et al., 2009). Unlike many MOFs in which different length linkers lead to isorecticular structures (Eddaoudi et al., 2002), the 5AIA–BP exhibits several notable similarities and differences when compared to 5AIA–BE. As shown in Fig. 4, 5AIA forms hydrogen bonds with two 5AIA molecules and two BP molecules. The 5AIA–BP interactions and one of the 5AIA–5AIA interactions are similar to those found in 5AIA–BE. The remaining 5AIA–5AIA interaction in 5AIA–BP consists solely of an N(amine)–H···OH hydrogen bond, as opposed to the N(amine)—H···O=C found in 5AIA–BP. Interestingly, this results in a total of five hydrogen bonds in the 5AIA–BP structure compared to the six hydrogen bonds observed in 5AIA–BE.The 5AIA–BE
crystallizes with one molecule of 5AIA and one molecule of BE in the (Fig. 1). Both molecules are effectively planar in the solid state (r.m.s. deviation for 5AIA = 0.155 Å). The BE moiety shows whole molecule disorder over two sets of sites, consistent with a local C2 rotation about the long axis of the molecule. The occupancy of the major and minor components was refined to be 0.588 (3) and 0.412 (3), respectively.In this structure, the 5AIA molecule forms hydrogen bonds to both itself and the BE moiety, forming extended sheets (Table 1 and Fig. 2). The 5AIA–5AIA interactions consist of N(amine)—H···O=C hydrogen bonds where each 5AIA makes two hydrogen bonds with two neighboring 5AIA molecules. The 5AIA–BE interaction consists of an O—H···N(pyridyl) hydrogen bond such that each 5AIA makes one hydrogen bond with two neighboring BE molecules. The sheets formed by these interactions stack along the the a axis to produce a layered structure (Fig. 3).
Recently, the
structure of 5AIA and 4,4'-bipyridine (BP), a shorter analogue of BE, was reported (Zhang et al., 2009). Unlike many MOFs in which different length linkers lead to isorecticular structures (Eddaoudi et al., 2002), the 5AIA–BP exhibits several notable similarites and differences when compared to 5AIA–BE. As shown in Fig. 4, 5AIA forms hydrogen bonds with two 5AIA molecules and two BP molecules. The 5AIA–BP interactions and one of the 5AIA–5AIA interactions are similar to those found in 5AIA–BE. The remaining 5AIA–5AIA interaction in 5AIA–BP consists solely of an N(amine)—H···OH hydrogen bond, as opposed to the N(amine)—H···O=C interaction found in 5AIA–BP. Interestingly, this results in a total of five hydrogen bonds in the 5AIA–BP structure compared to the six hydrogen bonds observed in 5AIA–BE.Solid BE (0.0119 g, 6.53 × 10 -5 mol) and 5AIA (0.0109 g, 6.02 × 10 -5 mol) were added to a 25 ml scintillation vial. To this was added approximately 15 ml of ethyl acetate followed by gentle heating. An additional 2 ml of methanol was added and all remaining solids dissolved. The loosely capped vial was then placed into a dark cabinet. After two weeks, yellow block-shaped crystals of the title compound suitable for single-crystal X-ray diffraction measurements were obtained.
Crystal data, data collection and structure
details are summarized in Table 2. Heteroatom hydrogen atoms were located in difference electron-density maps and freely refined. Hydrogen atoms attached to carbon atoms were refined using riding models with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C). The BE was found to be disordered over two sets of sites in a 0.588 (3): 0.412 (3) ratio.5-Amino-isophthalic acid (5AIA) is an emerging secondary building unit for a wide variety of metal–organic frameworks (MOFs). (Zeng et al., 2009; Wang et al., 2011; Cox et al., 2015) This compound is also a convenient precursor for the synthesis of azo-derivatized framework ligands, a key component in the rapidly evolving field of photochromic MOFs. (Brown et al., 2013; Castellanos et al., 2016; Walton et al., 2013; Patel et al., 2014). Similarly, 1,2-bis(pyridin-4-yl)ethene (BE) is also commonly used in MOF synthesis; however, it is routinely used in
engineering as well (Kongshaug & Fjellvag, 2003; MacGillivray et al., 2008; Desiraju, 1995) The 5AIA–BE presented herein was produced as part of an undergraduate physical chemistry laboratory experiment developed by Jason Benedict.Recently, the
structure of 5AIA and 4,4'-bipyridine (BP), a shorter analogue of BE, was reported (Zhang et al., 2009). Unlike many MOFs in which different length linkers lead to isorecticular structures (Eddaoudi et al., 2002), the 5AIA–BP exhibits several notable similarities and differences when compared to 5AIA–BE. As shown in Fig. 4, 5AIA forms hydrogen bonds with two 5AIA molecules and two BP molecules. The 5AIA–BP interactions and one of the 5AIA–5AIA interactions are similar to those found in 5AIA–BE. The remaining 5AIA–5AIA interaction in 5AIA–BP consists solely of an N(amine)–H···OH hydrogen bond, as opposed to the N(amine)—H···O=C found in 5AIA–BP. Interestingly, this results in a total of five hydrogen bonds in the 5AIA–BP structure compared to the six hydrogen bonds observed in 5AIA–BE.The 5AIA–BE
crystallizes with one molecule of 5AIA and one molecule of BE in the (Fig. 1). Both molecules are effectively planar in the solid state (r.m.s. deviation for 5AIA = 0.155 Å). The BE moiety shows whole molecule disorder over two sets of sites, consistent with a local C2 rotation about the long axis of the molecule. The occupancy of the major and minor components was refined to be 0.588 (3) and 0.412 (3), respectively.In this structure, the 5AIA molecule forms hydrogen bonds to both itself and the BE moiety, forming extended sheets (Table 1 and Fig. 2). The 5AIA–5AIA interactions consist of N(amine)—H···O=C hydrogen bonds where each 5AIA makes two hydrogen bonds with two neighboring 5AIA molecules. The 5AIA–BE interaction consists of an O—H···N(pyridyl) hydrogen bond such that each 5AIA makes one hydrogen bond with two neighboring BE molecules. The sheets formed by these interactions stack along the the a axis to produce a layered structure (Fig. 3).
Recently, the
structure of 5AIA and 4,4'-bipyridine (BP), a shorter analogue of BE, was reported (Zhang et al., 2009). Unlike many MOFs in which different length linkers lead to isorecticular structures (Eddaoudi et al., 2002), the 5AIA–BP exhibits several notable similarites and differences when compared to 5AIA–BE. As shown in Fig. 4, 5AIA forms hydrogen bonds with two 5AIA molecules and two BP molecules. The 5AIA–BP interactions and one of the 5AIA–5AIA interactions are similar to those found in 5AIA–BE. The remaining 5AIA–5AIA interaction in 5AIA–BP consists solely of an N(amine)—H···OH hydrogen bond, as opposed to the N(amine)—H···O=C interaction found in 5AIA–BP. Interestingly, this results in a total of five hydrogen bonds in the 5AIA–BP structure compared to the six hydrogen bonds observed in 5AIA–BE.Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009).Fig. 1. The asymmetric unit of the title compound, showing the numbering scheme. Displacement ellipsoids are shown at the 50% probability level. | |
Fig. 2. Diagram illustrating the hydrogen-bonding interactions present in the two-dimensional sheets found in the 5AIA–BE co-crystal. | |
Fig. 3. View down [001] showing the (100) sheets in the extended structure of the title compound. | |
Fig. 4. Diagram illustrating the hydrogen bonding interactions present in the previously reported 5AIA–BP co-crystal. |
C12H10N2·C8H7NO4 | F(000) = 760 |
Mr = 363.36 | Dx = 1.405 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.1614 (10) Å | Cell parameters from 428 reflections |
b = 12.0782 (12) Å | θ = 2.8–22.0° |
c = 14.0537 (14) Å | µ = 0.10 mm−1 |
β = 95.027 (2)° | T = 90 K |
V = 1718.2 (3) Å3 | Block, yellow |
Z = 4 | 0.22 × 0.2 × 0.18 mm |
Bruker SMART APEXII CCD diffractometer | 6546 independent reflections |
Radiation source: microfocus rotating anode, Incoatec Iµs | 4519 reflections with I > 2σ(I) |
Mirror optics monochromator | Rint = 0.033 |
Detector resolution: 7.9 pixels mm-1 | θmax = 33.2°, θmin = 2.2° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | k = −16→18 |
Tmin = 0.683, Tmax = 0.747 | l = −19→21 |
24372 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0727P)2 + 0.2884P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
6546 reflections | Δρmax = 0.40 e Å−3 |
378 parameters | Δρmin = −0.24 e Å−3 |
C12H10N2·C8H7NO4 | V = 1718.2 (3) Å3 |
Mr = 363.36 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.1614 (10) Å | µ = 0.10 mm−1 |
b = 12.0782 (12) Å | T = 90 K |
c = 14.0537 (14) Å | 0.22 × 0.2 × 0.18 mm |
β = 95.027 (2)° |
Bruker SMART APEXII CCD diffractometer | 6546 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | 4519 reflections with I > 2σ(I) |
Tmin = 0.683, Tmax = 0.747 | Rint = 0.033 |
24372 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.143 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.40 e Å−3 |
6546 reflections | Δρmin = −0.24 e Å−3 |
378 parameters |
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 | 0.21821 (10) | 0.91797 (6) | 0.42759 (6) | 0.0299 (2) | |
O2 | 0.18838 (9) | 0.81890 (6) | 0.55840 (5) | 0.02654 (18) | |
H2 | 0.1646 (19) | 0.8932 (16) | 0.5810 (13) | 0.058 (5)* | |
O3 | 0.35542 (10) | 0.33662 (6) | 0.42624 (6) | 0.0309 (2) | |
O4 | 0.35891 (9) | 0.43117 (6) | 0.56369 (5) | 0.02640 (18) | |
H4 | 0.388 (2) | 0.3606 (16) | 0.5933 (14) | 0.064 (6)* | |
N1 | 0.27113 (12) | 0.63283 (8) | 0.17186 (7) | 0.0291 (2) | |
H1A | 0.2656 (17) | 0.5692 (14) | 0.1385 (12) | 0.043 (4)* | |
H1B | 0.2351 (16) | 0.6925 (14) | 0.1424 (11) | 0.040 (4)* | |
C1 | 0.27076 (11) | 0.62966 (8) | 0.26981 (7) | 0.02010 (19) | |
C2 | 0.29909 (11) | 0.53166 (8) | 0.32097 (7) | 0.02032 (19) | |
H2A | 0.3164 | 0.4657 | 0.2874 | 0.024* | |
C3 | 0.30223 (10) | 0.52951 (8) | 0.42012 (7) | 0.01921 (19) | |
C4 | 0.27368 (11) | 0.62462 (8) | 0.47130 (7) | 0.01990 (19) | |
H4A | 0.2728 | 0.6226 | 0.5388 | 0.024* | |
C5 | 0.24644 (10) | 0.72289 (8) | 0.42033 (7) | 0.01881 (19) | |
C6 | 0.24657 (10) | 0.72561 (8) | 0.32144 (7) | 0.01947 (19) | |
H6 | 0.2300 | 0.7935 | 0.2884 | 0.023* | |
C7 | 0.21669 (11) | 0.82903 (8) | 0.46877 (7) | 0.0211 (2) | |
C8 | 0.34070 (11) | 0.42315 (8) | 0.46985 (7) | 0.0215 (2) | |
C18 | 0.89056 (13) | 0.89912 (9) | 0.43551 (9) | 0.0306 (3) | |
H18 | 0.8831 | 0.9091 | 0.5019 | 0.037* | 0.588 (3) |
H18A | 0.8865 | 0.9167 | 0.5011 | 0.037* | 0.412 (3) |
N2 | 0.9309 (8) | 0.2578 (6) | 0.1571 (3) | 0.0206 (8) | 0.588 (3) |
N3 | 0.8888 (10) | 0.9864 (5) | 0.3724 (9) | 0.0203 (11) | 0.588 (3) |
C9 | 0.9283 (3) | 0.3491 (2) | 0.1046 (2) | 0.0259 (5) | 0.588 (3) |
H9 | 0.9195 | 0.3426 | 0.0370 | 0.031* | 0.588 (3) |
C10 | 0.9382 (2) | 0.45426 (16) | 0.1453 (2) | 0.0246 (4) | 0.588 (3) |
H10 | 0.9393 | 0.5181 | 0.1058 | 0.029* | 0.588 (3) |
C11 | 0.94634 (18) | 0.46501 (16) | 0.24375 (18) | 0.0202 (4) | 0.588 (3) |
C12 | 0.9527 (2) | 0.36771 (18) | 0.29764 (18) | 0.0260 (5) | 0.588 (3) |
H12 | 0.9624 | 0.3709 | 0.3654 | 0.031* | 0.588 (3) |
C13 | 0.9446 (4) | 0.2666 (3) | 0.2511 (2) | 0.0240 (6) | 0.588 (3) |
H13 | 0.9491 | 0.2008 | 0.2883 | 0.029* | 0.588 (3) |
C14 | 0.9425 (2) | 0.57258 (15) | 0.29274 (13) | 0.0245 (5) | 0.588 (3) |
H14 | 0.9538 | 0.5724 | 0.3606 | 0.029* | 0.588 (3) |
C15 | 0.9246 (2) | 0.66976 (15) | 0.24941 (15) | 0.0241 (4) | 0.588 (3) |
H15 | 0.9170 | 0.6692 | 0.1816 | 0.029* | 0.588 (3) |
C16 | 0.9152 (3) | 0.7790 (2) | 0.2963 (2) | 0.0182 (5) | 0.588 (3) |
C17 | 0.9045 (7) | 0.7916 (5) | 0.3934 (2) | 0.0242 (8) | 0.588 (3) |
H17 | 0.9064 | 0.7278 | 0.4330 | 0.029* | 0.588 (3) |
C19 | 0.9010 (9) | 0.9740 (6) | 0.2814 (5) | 0.0214 (8) | 0.588 (3) |
H19 | 0.8997 | 1.0381 | 0.2422 | 0.026* | 0.588 (3) |
C20 | 0.9153 (4) | 0.8733 (3) | 0.2402 (3) | 0.0244 (6) | 0.588 (3) |
H20 | 0.9254 | 0.8678 | 0.1738 | 0.029* | 0.588 (3) |
C17A | 0.9027 (10) | 0.7907 (7) | 0.4220 (4) | 0.0258 (10) | 0.412 (3) |
H17A | 0.9026 | 0.7388 | 0.4728 | 0.031* | 0.412 (3) |
C9A | 0.9486 (4) | 0.3433 (3) | 0.0717 (3) | 0.0219 (7) | 0.412 (3) |
H9A | 0.9550 | 0.3259 | 0.0064 | 0.026* | 0.412 (3) |
C20A | 0.9161 (6) | 0.8429 (4) | 0.2607 (4) | 0.0260 (11) | 0.412 (3) |
H20A | 0.9275 | 0.8265 | 0.1958 | 0.031* | 0.412 (3) |
N2A | 0.9319 (11) | 0.2579 (10) | 0.1328 (4) | 0.0202 (10) | 0.412 (3) |
N3A | 0.8830 (15) | 0.9861 (9) | 0.3829 (13) | 0.025 (2) | 0.412 (3) |
C19A | 0.8995 (15) | 0.9532 (9) | 0.2902 (9) | 0.034 (2) | 0.412 (3) |
H19A | 0.8996 | 1.0094 | 0.2428 | 0.040* | 0.412 (3) |
C10A | 0.9569 (3) | 0.4532 (2) | 0.0982 (3) | 0.0243 (6) | 0.412 (3) |
H10A | 0.9663 | 0.5087 | 0.0514 | 0.029* | 0.412 (3) |
C11A | 0.9515 (3) | 0.4826 (2) | 0.1934 (3) | 0.0195 (6) | 0.412 (3) |
C12A | 0.9434 (3) | 0.3974 (3) | 0.2586 (3) | 0.0250 (6) | 0.412 (3) |
H12A | 0.9448 | 0.4125 | 0.3250 | 0.030* | 0.412 (3) |
C13A | 0.9330 (6) | 0.2880 (4) | 0.2245 (4) | 0.0293 (10) | 0.412 (3) |
H13A | 0.9262 | 0.2309 | 0.2703 | 0.035* | 0.412 (3) |
C14A | 0.9493 (3) | 0.6007 (2) | 0.21878 (19) | 0.0235 (6) | 0.412 (3) |
H14A | 0.9676 | 0.6526 | 0.1709 | 0.028* | 0.412 (3) |
C15A | 0.9237 (3) | 0.6405 (2) | 0.3033 (2) | 0.0226 (6) | 0.412 (3) |
H15A | 0.9095 | 0.5884 | 0.3521 | 0.027* | 0.412 (3) |
C16A | 0.9155 (4) | 0.7585 (4) | 0.3276 (3) | 0.0186 (7) | 0.412 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0508 (6) | 0.0126 (3) | 0.0286 (4) | 0.0008 (3) | 0.0170 (4) | −0.0002 (3) |
O2 | 0.0459 (5) | 0.0155 (3) | 0.0195 (3) | 0.0059 (3) | 0.0096 (3) | −0.0016 (3) |
O3 | 0.0510 (6) | 0.0143 (3) | 0.0270 (4) | 0.0041 (3) | 0.0012 (4) | −0.0046 (3) |
O4 | 0.0438 (5) | 0.0149 (3) | 0.0201 (3) | 0.0063 (3) | 0.0006 (3) | −0.0003 (3) |
N1 | 0.0510 (7) | 0.0180 (4) | 0.0186 (4) | 0.0067 (4) | 0.0058 (4) | −0.0018 (3) |
C1 | 0.0246 (5) | 0.0175 (4) | 0.0187 (4) | 0.0010 (4) | 0.0046 (4) | −0.0022 (3) |
C2 | 0.0255 (5) | 0.0148 (4) | 0.0210 (4) | 0.0017 (4) | 0.0039 (4) | −0.0038 (3) |
C3 | 0.0242 (5) | 0.0130 (4) | 0.0206 (4) | 0.0003 (3) | 0.0030 (4) | −0.0012 (3) |
C4 | 0.0269 (5) | 0.0142 (4) | 0.0191 (4) | 0.0002 (4) | 0.0047 (4) | −0.0016 (3) |
C5 | 0.0235 (5) | 0.0130 (4) | 0.0206 (4) | −0.0001 (3) | 0.0056 (4) | −0.0026 (3) |
C6 | 0.0236 (5) | 0.0140 (4) | 0.0213 (4) | 0.0010 (3) | 0.0050 (4) | −0.0006 (3) |
C7 | 0.0285 (5) | 0.0142 (4) | 0.0214 (4) | 0.0004 (4) | 0.0069 (4) | −0.0025 (3) |
C8 | 0.0285 (5) | 0.0145 (4) | 0.0217 (5) | −0.0002 (4) | 0.0025 (4) | −0.0023 (3) |
C18 | 0.0394 (7) | 0.0178 (5) | 0.0360 (6) | 0.0017 (4) | 0.0118 (5) | −0.0001 (4) |
N2 | 0.0261 (11) | 0.0147 (9) | 0.021 (2) | −0.0007 (7) | 0.0014 (18) | −0.0088 (18) |
N3 | 0.0306 (19) | 0.0099 (16) | 0.022 (3) | 0.0050 (11) | 0.0112 (14) | −0.0001 (12) |
C9 | 0.0351 (14) | 0.0194 (9) | 0.0238 (13) | −0.0024 (8) | 0.0066 (10) | −0.0027 (10) |
C10 | 0.0400 (12) | 0.0158 (8) | 0.0182 (11) | −0.0012 (7) | 0.0044 (9) | −0.0006 (8) |
C11 | 0.0232 (9) | 0.0158 (10) | 0.0219 (11) | −0.0012 (6) | 0.0037 (7) | −0.0024 (7) |
C12 | 0.0388 (12) | 0.0170 (9) | 0.0225 (10) | 0.0016 (8) | 0.0038 (9) | −0.0012 (8) |
C13 | 0.0341 (13) | 0.0160 (13) | 0.0225 (15) | 0.0007 (10) | 0.0055 (12) | −0.0034 (9) |
C14 | 0.0348 (11) | 0.0173 (9) | 0.0218 (8) | 0.0012 (7) | 0.0053 (7) | −0.0064 (6) |
C15 | 0.0325 (10) | 0.0176 (8) | 0.0223 (9) | −0.0004 (7) | 0.0021 (7) | −0.0056 (7) |
C16 | 0.0226 (9) | 0.0109 (14) | 0.0211 (13) | 0.0001 (8) | 0.0021 (10) | 0.0004 (10) |
C17 | 0.0346 (13) | 0.0133 (9) | 0.026 (2) | 0.0011 (8) | 0.0086 (18) | −0.0038 (17) |
C19 | 0.0301 (15) | 0.0192 (19) | 0.0155 (15) | 0.0019 (14) | 0.0054 (11) | −0.0047 (15) |
C20 | 0.0324 (12) | 0.0204 (16) | 0.0205 (14) | 0.0012 (12) | 0.0019 (10) | −0.0034 (10) |
C17A | 0.0330 (18) | 0.0195 (15) | 0.027 (3) | 0.0003 (12) | 0.011 (3) | −0.005 (2) |
C9A | 0.0281 (17) | 0.0136 (11) | 0.0247 (18) | −0.0015 (10) | 0.0065 (14) | −0.0010 (13) |
C20A | 0.0378 (18) | 0.019 (3) | 0.021 (2) | 0.0028 (19) | 0.0022 (17) | −0.0085 (17) |
N2A | 0.0234 (15) | 0.0201 (13) | 0.017 (3) | 0.0010 (10) | −0.001 (2) | −0.010 (2) |
N3A | 0.026 (3) | 0.033 (4) | 0.016 (3) | −0.001 (2) | 0.008 (2) | −0.011 (2) |
C19A | 0.039 (3) | 0.029 (4) | 0.032 (3) | −0.002 (3) | 0.0015 (19) | 0.006 (2) |
C10A | 0.0320 (15) | 0.0166 (11) | 0.0243 (15) | −0.0019 (10) | 0.0035 (12) | −0.0024 (10) |
C11A | 0.0250 (13) | 0.0163 (11) | 0.0170 (15) | −0.0012 (9) | 0.0008 (10) | −0.0038 (11) |
C12A | 0.0386 (17) | 0.0155 (16) | 0.0209 (15) | 0.0010 (11) | 0.0017 (12) | −0.0020 (11) |
C13A | 0.041 (2) | 0.019 (2) | 0.027 (3) | 0.0004 (15) | 0.0012 (19) | 0.0024 (15) |
C14A | 0.0299 (14) | 0.0125 (10) | 0.0283 (13) | −0.0003 (9) | 0.0033 (10) | −0.0035 (9) |
C15A | 0.0308 (14) | 0.0119 (12) | 0.0251 (14) | 0.0007 (9) | 0.0020 (10) | −0.0013 (9) |
C16A | 0.0207 (13) | 0.0107 (14) | 0.024 (2) | 0.0002 (10) | 0.0012 (14) | 0.0033 (15) |
O1—C7 | 1.2209 (12) | C12—H12 | 0.9500 |
O2—H2 | 0.990 (19) | C12—C13 | 1.385 (4) |
O2—C7 | 1.3222 (12) | C13—H13 | 0.9500 |
O3—C8 | 1.2274 (12) | C14—H14 | 0.9500 |
O4—H4 | 0.98 (2) | C14—C15 | 1.327 (3) |
O4—C8 | 1.3191 (12) | C15—H15 | 0.9500 |
N1—H1A | 0.899 (17) | C15—C16 | 1.482 (3) |
N1—H1B | 0.894 (17) | C16—C17 | 1.387 (4) |
N1—C1 | 1.3775 (13) | C16—C20 | 1.385 (3) |
C1—C2 | 1.4017 (14) | C17—H17 | 0.9500 |
C1—C6 | 1.4005 (13) | C19—H19 | 0.9500 |
C2—H2A | 0.9500 | C19—C20 | 1.360 (7) |
C2—C3 | 1.3912 (14) | C20—H20 | 0.9500 |
C3—C4 | 1.3991 (13) | C17A—H17A | 0.9500 |
C3—C8 | 1.4979 (14) | C17A—C16A | 1.399 (6) |
C4—H4A | 0.9500 | C9A—H9A | 0.9500 |
C4—C5 | 1.4014 (13) | C9A—N2A | 1.361 (10) |
C5—C6 | 1.3902 (14) | C9A—C10A | 1.379 (4) |
C5—C7 | 1.4948 (13) | C20A—H20A | 0.9500 |
C6—H6 | 0.9500 | C20A—C19A | 1.410 (11) |
C18—H18 | 0.9500 | C20A—C16A | 1.388 (5) |
C18—H18A | 0.9500 | N2A—C13A | 1.338 (7) |
C18—N3 | 1.376 (9) | N3A—C19A | 1.39 (2) |
C18—C17 | 1.439 (5) | C19A—H19A | 0.9500 |
C18—C17A | 1.331 (9) | C10A—H10A | 0.9500 |
C18—N3A | 1.283 (13) | C10A—C11A | 1.390 (5) |
N2—C9 | 1.326 (7) | C11A—C12A | 1.385 (4) |
N2—C13 | 1.320 (5) | C11A—C14A | 1.472 (4) |
N3—C19 | 1.305 (13) | C12A—H12A | 0.9500 |
C9—H9 | 0.9500 | C12A—C13A | 1.406 (6) |
C9—C10 | 1.392 (3) | C13A—H13A | 0.9500 |
C10—H10 | 0.9500 | C14A—H14A | 0.9500 |
C10—C11 | 1.386 (3) | C14A—C15A | 1.329 (4) |
C11—C12 | 1.397 (3) | C15A—H15A | 0.9500 |
C11—C14 | 1.472 (2) | C15A—C16A | 1.469 (5) |
C7—O2—H2 | 107.5 (11) | C15—C14—C11 | 125.02 (18) |
C8—O4—H4 | 111.7 (11) | C15—C14—H14 | 117.5 |
H1A—N1—H1B | 116.4 (15) | C14—C15—H15 | 116.7 |
C1—N1—H1A | 119.4 (11) | C14—C15—C16 | 126.5 (2) |
C1—N1—H1B | 116.6 (10) | C16—C15—H15 | 116.7 |
N1—C1—C2 | 121.17 (9) | C17—C16—C15 | 123.3 (3) |
N1—C1—C6 | 120.72 (9) | C20—C16—C15 | 118.4 (3) |
C6—C1—C2 | 118.07 (9) | C20—C16—C17 | 118.3 (4) |
C1—C2—H2A | 119.5 | C18—C17—H17 | 119.2 |
C3—C2—C1 | 121.01 (9) | C16—C17—C18 | 121.5 (4) |
C3—C2—H2A | 119.5 | C16—C17—H17 | 119.2 |
C2—C3—C4 | 120.80 (9) | N3—C19—H19 | 118.6 |
C2—C3—C8 | 117.74 (8) | N3—C19—C20 | 122.9 (6) |
C4—C3—C8 | 121.44 (9) | C20—C19—H19 | 118.6 |
C3—C4—H4A | 120.9 | C16—C20—H20 | 120.4 |
C3—C4—C5 | 118.24 (9) | C19—C20—C16 | 119.2 (4) |
C5—C4—H4A | 120.9 | C19—C20—H20 | 120.4 |
C4—C5—C7 | 122.17 (9) | C18—C17A—H17A | 122.4 |
C6—C5—C4 | 120.90 (9) | C18—C17A—C16A | 115.3 (5) |
C6—C5—C7 | 116.93 (8) | C16A—C17A—H17A | 122.4 |
C1—C6—H6 | 119.5 | N2A—C9A—H9A | 117.7 |
C5—C6—C1 | 120.93 (9) | N2A—C9A—C10A | 124.5 (5) |
C5—C6—H6 | 119.5 | C10A—C9A—H9A | 117.7 |
O1—C7—O2 | 123.09 (9) | C19A—C20A—H20A | 120.4 |
O1—C7—C5 | 121.82 (9) | C16A—C20A—H20A | 120.4 |
O2—C7—C5 | 115.09 (8) | C16A—C20A—C19A | 119.2 (6) |
O3—C8—O4 | 123.31 (9) | C13A—N2A—C9A | 114.3 (9) |
O3—C8—C3 | 122.38 (9) | C18—N3A—C19A | 107.5 (10) |
O4—C8—C3 | 114.30 (8) | C20A—C19A—H19A | 117.5 |
N3—C18—H18 | 122.5 | N3A—C19A—C20A | 125.0 (9) |
N3—C18—C17 | 115.0 (5) | N3A—C19A—H19A | 117.5 |
C17—C18—H18 | 122.5 | C9A—C10A—H10A | 120.1 |
C17A—C18—H18A | 111.8 | C9A—C10A—C11A | 119.9 (3) |
N3A—C18—H18A | 111.8 | C11A—C10A—H10A | 120.1 |
N3A—C18—C17A | 136.5 (8) | C10A—C11A—C14A | 118.9 (3) |
C13—N2—C9 | 119.0 (5) | C12A—C11A—C10A | 117.2 (2) |
C19—N3—C18 | 123.1 (6) | C12A—C11A—C14A | 123.8 (3) |
N2—C9—H9 | 118.9 | C11A—C12A—H12A | 120.7 |
N2—C9—C10 | 122.3 (3) | C11A—C12A—C13A | 118.6 (3) |
C10—C9—H9 | 118.9 | C13A—C12A—H12A | 120.7 |
C9—C10—H10 | 120.3 | N2A—C13A—C12A | 125.3 (6) |
C11—C10—C9 | 119.4 (2) | N2A—C13A—H13A | 117.4 |
C11—C10—H10 | 120.3 | C12A—C13A—H13A | 117.4 |
C10—C11—C12 | 117.31 (16) | C11A—C14A—H14A | 117.4 |
C10—C11—C14 | 123.2 (2) | C15A—C14A—C11A | 125.2 (3) |
C12—C11—C14 | 119.4 (2) | C15A—C14A—H14A | 117.4 |
C11—C12—H12 | 120.4 | C14A—C15A—H15A | 117.3 |
C13—C12—C11 | 119.2 (2) | C14A—C15A—C16A | 125.3 (3) |
C13—C12—H12 | 120.4 | C16A—C15A—H15A | 117.3 |
N2—C13—C12 | 122.7 (4) | C17A—C16A—C15A | 120.1 (5) |
N2—C13—H13 | 118.6 | C20A—C16A—C17A | 116.4 (5) |
C12—C13—H13 | 118.6 | C20A—C16A—C15A | 123.5 (4) |
C11—C14—H14 | 117.5 | ||
N1—C1—C2—C3 | 178.19 (10) | C11—C14—C15—C16 | 177.6 (2) |
N1—C1—C6—C5 | −179.82 (10) | C12—C11—C14—C15 | −173.6 (2) |
C1—C2—C3—C4 | 1.71 (16) | C13—N2—C9—C10 | −0.7 (9) |
C1—C2—C3—C8 | −176.64 (10) | C14—C11—C12—C13 | 174.4 (3) |
C2—C1—C6—C5 | −2.05 (16) | C14—C15—C16—C17 | −10.0 (5) |
C2—C3—C4—C5 | −2.20 (16) | C14—C15—C16—C20 | 170.8 (3) |
C2—C3—C8—O3 | −7.84 (17) | C15—C16—C17—C18 | −177.6 (3) |
C2—C3—C8—O4 | 171.27 (10) | C15—C16—C20—C19 | 177.1 (5) |
C3—C4—C5—C6 | 0.59 (16) | C17—C18—N3—C19 | −1.1 (12) |
C3—C4—C5—C7 | −179.15 (10) | C17—C18—C17A—C16A | 1.4 (17) |
C4—C3—C8—O3 | 173.81 (11) | C17—C18—N3A—C19A | −3.8 (15) |
C4—C3—C8—O4 | −7.07 (15) | C17—C16—C20—C19 | −2.0 (7) |
C4—C5—C6—C1 | 1.56 (16) | C20—C16—C17—C18 | 1.5 (7) |
C4—C5—C7—O1 | 165.59 (11) | C17A—C18—N3—C19 | −0.5 (14) |
C4—C5—C7—O2 | −14.70 (15) | C17A—C18—C17—C16 | −179 (3) |
C6—C1—C2—C3 | 0.43 (16) | C17A—C18—N3A—C19A | −4.3 (18) |
C6—C5—C7—O1 | −14.15 (16) | C9A—N2A—C13A—C12A | 3.1 (13) |
C6—C5—C7—O2 | 165.55 (10) | C9A—C10A—C11A—C12A | 2.7 (4) |
C7—C5—C6—C1 | −178.69 (10) | C9A—C10A—C11A—C14A | −174.9 (3) |
C8—C3—C4—C5 | 176.09 (10) | N2A—C9A—C10A—C11A | 1.6 (8) |
C18—N3—C19—C20 | 0.6 (15) | N3A—C18—N3—C19 | −159 (11) |
C18—C17A—C16A—C20A | 0.9 (9) | N3A—C18—C17—C16 | 2.5 (10) |
C18—C17A—C16A—C15A | −177.3 (5) | N3A—C18—C17A—C16A | 2.8 (15) |
C18—N3A—C19A—C20A | 2 (2) | C19A—C20A—C16A—C17A | −2.1 (11) |
N2—C9—C10—C11 | −2.3 (6) | C19A—C20A—C16A—C15A | 176.0 (8) |
N3—C18—C17—C16 | 0.0 (8) | C10A—C9A—N2A—C13A | −4.4 (12) |
N3—C18—C17A—C16A | −0.3 (12) | C10A—C11A—C12A—C13A | −3.8 (5) |
N3—C18—N3A—C19A | 19 (9) | C10A—C11A—C14A—C15A | 168.9 (3) |
N3—C19—C20—C16 | 1.0 (12) | C11A—C12A—C13A—N2A | 0.9 (9) |
C9—N2—C13—C12 | 1.9 (9) | C11A—C14A—C15A—C16A | −177.1 (3) |
C9—C10—C11—C12 | 4.0 (3) | C12A—C11A—C14A—C15A | −8.5 (5) |
C9—C10—C11—C14 | −173.2 (2) | C14A—C11A—C12A—C13A | 173.6 (4) |
C10—C11—C12—C13 | −2.9 (3) | C14A—C15A—C16A—C17A | −172.8 (5) |
C10—C11—C14—C15 | 3.5 (3) | C14A—C15A—C16A—C20A | 9.1 (6) |
C11—C12—C13—N2 | −0.1 (6) | C16A—C20A—C19A—N3A | 0.5 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.899 (17) | 2.062 (17) | 2.9540 (13) | 171.0 (15) |
N1—H1B···O3ii | 0.894 (17) | 2.157 (17) | 3.0500 (13) | 178.6 (13) |
O2—H2···N3iii | 0.989 (19) | 1.70 (2) | 2.688 (8) | 173.4 (18) |
O2—H2···N3Aiii | 0.989 (19) | 1.63 (2) | 2.619 (12) | 177 (2) |
O4—H4···N2iv | 0.98 (2) | 1.72 (2) | 2.702 (7) | 173.2 (19) |
O4—H4···N2Aiv | 0.98 (2) | 1.59 (2) | 2.566 (11) | 175 (2) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1, −y+2, −z+1; (iv) x−1/2, −y+1/2, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.899 (17) | 2.062 (17) | 2.9540 (13) | 171.0 (15) |
N1—H1B···O3ii | 0.894 (17) | 2.157 (17) | 3.0500 (13) | 178.6 (13) |
O2—H2···N3iii | 0.989 (19) | 1.70 (2) | 2.688 (8) | 173.4 (18) |
O2—H2···N3Aiii | 0.989 (19) | 1.63 (2) | 2.619 (12) | 177 (2) |
O4—H4···N2iv | 0.98 (2) | 1.72 (2) | 2.702 (7) | 173.2 (19) |
O4—H4···N2Aiv | 0.98 (2) | 1.59 (2) | 2.566 (11) | 175 (2) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1, −y+2, −z+1; (iv) x−1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C12H10N2·C8H7NO4 |
Mr | 363.36 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 90 |
a, b, c (Å) | 10.1614 (10), 12.0782 (12), 14.0537 (14) |
β (°) | 95.027 (2) |
V (Å3) | 1718.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.22 × 0.2 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2014) |
Tmin, Tmax | 0.683, 0.747 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24372, 6546, 4519 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.771 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.143, 1.02 |
No. of reflections | 6546 |
No. of parameters | 378 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.40, −0.24 |
Computer programs: APEX2 (Bruker, 2014), SAINT (Bruker, 2014), SHELXT (Sheldrick, 2015), SHELXL2014 (Sheldrick, 2015b), OLEX2 (Dolomanov et al., 2009).
Acknowledgements
This material is based upon work supported by the National Science Foundation under grant No. DMR-1455039.
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