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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 5| May 2016| Pages 639-642

Crystal structure of the co-crystal of 5-amino­isophthalic acid and 1,2-bis­(pyridin-4-yl)ethene

CROSSMARK_Color_square_no_text.svg

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

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 23 January 2016; accepted 28 March 2016; online 8 April 2016)

In the title 1:1 co-crystal, C12H10N2·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 co-crystal of 5-amino-isophthalic acid and the shorter 4,4′-bipryidine is presented.

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[Zeng, M.-H., Hu, S., Chen, Q., Xie, G., Shuai, Q., Gao, S.-L. & Tang, L.-Y. (2009). Inorg. Chem. 48, 7070-7079.]; Wang et al., 2011[Wang, H.-N., Meng, X., Yang, G.-S., Wang, X.-L., Shao, K.-Z., Su, Z.-M. & Wang, C.-G. (2011). Chem. Commun. 47, 7128-7130.]; Cox et al., 2015[Cox, J. M., Walton, I. M., Benson, C. A., Chen, Y.-S. & Benedict, J. B. (2015). J. Appl. Cryst. 48, 578-581.]) 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[Brown, J. W., Henderson, B. L., Kiesz, M. D., Whalley, A. C., Morris, W., Grunder, S., Deng, H., Furukawa, H., Zink, J. I., Stoddart, J. F. & Yaghi, O. M. (2013). Chem. Sci. 4, 2858-2864.]; Castellanos et al., 2016[Castellanos, S., Goulet-Hanssens, A., Zhao, F., Dikhtiarenko, A., Pustovarenko, A., Hecht, S., Gascon, J., Kapteijn, F. & Bléger, D. (2016). Chem. Eur. J. 22, 746-752.]; Walton et al., 2013[Walton, I. M., Cox, J. M., Coppin, J. A., Linderman, C. M., Patel, D. G. (D.) & Benedict, J. B. (2013). Chem. Commun. 49, 8012-8014.]; Patel et al., 2014[Patel, D. G. (D.), Walton, I. M., Cox, J. M., Gleason, C. J., Butzer, D. R. & Benedict, J. B. (2014). Chem. Commun. 50, 2653-2656.]). Similarly, 1,2-bis(pyridin-4-yl)ethene (BE) is also commonly used in MOF synthesis; however, it is routinely used in co-crystal engineering as well (Kongshaug & Fjellvag, 2003[Kongshaug, K. O. & Fjellvåg, H. (2003). J. Solid State Chem. 175, 182-187.]; MacGillivray et al., 2008[MacGillivray, L. R., Papaefstathiou, G. S., Friščić, T., Hamilton, T. D., Bučar, D.-K., Chu, Q., Varshney, D. B. & Georgiev, I. G. (2008). Acc. Chem. Res. 41, 280-291.]; Desiraju, 1995[Desiraju, G. R. (1995). Angew. Chem. Int. Ed. Engl. 34, 2311-2327.]) The 5AIA–BE co-crystal presented herein was produced as part of an undergraduate physical chemistry laboratory experiment developed by Jason Benedict.

[Scheme 1]

Recently, the co-crystal structure of 5AIA and 4,4′-bi­pyridine (BP), a shorter analogue of BE, was reported (Zhang et al., 2009[Zhang, X., Zhu, B. & Guo, F. (2009). Asian J. Chem. 21, 7072-7076.]). Unlike many MOFs in which different length linkers lead to isorecticular structures (Eddaoudi et al., 2002[Eddaoudi, M., Kim, J., Rosi, N., Vodak, D., Wachter, J., O'Keeffe, M. & Yaghi, O. M. (2002). Science, 295, 469-472.]), the 5AIA–BP co-crystal 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.

2. Structural commentary

The 5AIA–BE co-crystal crystallizes with one mol­ecule of 5AIA and one mol­ecule of BE in the asymmetric unit (Fig. 1[link]). 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.

[Figure 1]
Figure 1
The asymmetric unit of the title compound, showing the numbering scheme. Displacement ellipsoids are shown at the 50% probability level.

3. Supra­molecular features

In this structure, the 5AIA mol­ecule forms hydrogen bonds to both itself and the BE moiety, forming extended sheets (Table 1[link] and Fig. 2[link]). 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[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+1, -y+2, -z+1; (iv) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].
[Figure 2]
Figure 2
Diagram illustrating the hydrogen-bonding inter­actions present in the two-dimensional sheets found in the 5AIA–BE co-crystal.
[Figure 3]
Figure 3
View down [001] showing the (100) sheets in the extended structure of the title compound.

4. Database survey

Recently, the co-crystal structure of 5AIA and 4,4′-bi­pyridine (BP), a shorter analogue of BE, was reported (Zhang et al., 2009[Zhang, X., Zhu, B. & Guo, F. (2009). Asian J. Chem. 21, 7072-7076.]). Unlike many MOFs in which different length linkers lead to isorecticular structures (Eddaoudi et al., 2002[Eddaoudi, M., Kim, J., Rosi, N., Vodak, D., Wachter, J., O'Keeffe, M. & Yaghi, O. M. (2002). Science, 295, 469-472.]), the 5AIA–BP co-crystal exhibits several notable similarites and differences when compared to 5AIA–BE. As shown in Figs. 4[link], 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.

[Figure 4]
Figure 4
Diagram illustrating the hydrogen bonding inter­actions present in the previously reported 5AIA–BP co-crystal.

5. 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 refinement details are summarized in Table 2[link]. 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.

Table 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)
V3) 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[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
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−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 and SAINT (Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]b) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Supporting information


Chemical context top

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 co-crystal engineering as well (Kongshaug & Fjellvag, 2003; MacGillivray et al., 2008; Desiraju, 1995) The 5AIA–BE co-crystal presented herein was produced as part of an undergraduate physical chemistry laboratory experiment developed by Jason Benedict.

Recently, the co-crystal 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 co-crystal 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.

Structural commentary top

The 5AIA–BE co-crystal crystallizes with one molecule of 5AIA and one molecule of BE in the asymmetric unit (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.

Supra­molecular features top

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).

Database survey top

Recently, the co-crystal 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 co-crystal 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.

Experimental top

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.

Refinement top

Crystal data, data collection and structure refinement 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.

Structure description top

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 co-crystal engineering as well (Kongshaug & Fjellvag, 2003; MacGillivray et al., 2008; Desiraju, 1995) The 5AIA–BE co-crystal presented herein was produced as part of an undergraduate physical chemistry laboratory experiment developed by Jason Benedict.

Recently, the co-crystal 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 co-crystal 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 co-crystal crystallizes with one molecule of 5AIA and one molecule of BE in the asymmetric unit (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 co-crystal 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 co-crystal 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.

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing the numbering scheme. Displacement ellipsoids are shown at the 50% probability level.
[Figure 2] Fig. 2. Diagram illustrating the hydrogen-bonding interactions present in the two-dimensional sheets found in the 5AIA–BE co-crystal.
[Figure 3] Fig. 3. View down [001] showing the (100) sheets in the extended structure of the title compound.
[Figure 4] Fig. 4. Diagram illustrating the hydrogen bonding interactions present in the previously reported 5AIA–BP co-crystal.
5-Aminoisophthalic acid–1,2-bis(pyridin-4-yl)ethene (1/1) top
Crystal data top
C12H10N2·C8H7NO4F(000) = 760
Mr = 363.36Dx = 1.405 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.1614 (10) ÅCell parameters from 428 reflections
b = 12.0782 (12) Åθ = 2.8–22.0°
c = 14.0537 (14) ŵ = 0.10 mm1
β = 95.027 (2)°T = 90 K
V = 1718.2 (3) Å3Block, yellow
Z = 40.22 × 0.2 × 0.18 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
6546 independent reflections
Radiation source: microfocus rotating anode, Incoatec Iµs4519 reflections with I > 2σ(I)
Mirror optics monochromatorRint = 0.033
Detector resolution: 7.9 pixels mm-1θmax = 33.2°, θmin = 2.2°
ω scansh = 1515
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
k = 1618
Tmin = 0.683, Tmax = 0.747l = 1921
24372 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047H 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 reflectionsΔρmax = 0.40 e Å3
378 parametersΔρmin = 0.24 e Å3
Crystal data top
C12H10N2·C8H7NO4V = 1718.2 (3) Å3
Mr = 363.36Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.1614 (10) ŵ = 0.10 mm1
b = 12.0782 (12) ÅT = 90 K
c = 14.0537 (14) Å0.22 × 0.2 × 0.18 mm
β = 95.027 (2)°
Data collection top
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 = 0.747Rint = 0.033
24372 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.40 e Å3
6546 reflectionsΔρmin = 0.24 e Å3
378 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.21821 (10)0.91797 (6)0.42759 (6)0.0299 (2)
O20.18838 (9)0.81890 (6)0.55840 (5)0.02654 (18)
H20.1646 (19)0.8932 (16)0.5810 (13)0.058 (5)*
O30.35542 (10)0.33662 (6)0.42624 (6)0.0309 (2)
O40.35891 (9)0.43117 (6)0.56369 (5)0.02640 (18)
H40.388 (2)0.3606 (16)0.5933 (14)0.064 (6)*
N10.27113 (12)0.63283 (8)0.17186 (7)0.0291 (2)
H1A0.2656 (17)0.5692 (14)0.1385 (12)0.043 (4)*
H1B0.2351 (16)0.6925 (14)0.1424 (11)0.040 (4)*
C10.27076 (11)0.62966 (8)0.26981 (7)0.02010 (19)
C20.29909 (11)0.53166 (8)0.32097 (7)0.02032 (19)
H2A0.31640.46570.28740.024*
C30.30223 (10)0.52951 (8)0.42012 (7)0.01921 (19)
C40.27368 (11)0.62462 (8)0.47130 (7)0.01990 (19)
H4A0.27280.62260.53880.024*
C50.24644 (10)0.72289 (8)0.42033 (7)0.01881 (19)
C60.24657 (10)0.72561 (8)0.32144 (7)0.01947 (19)
H60.23000.79350.28840.023*
C70.21669 (11)0.82903 (8)0.46877 (7)0.0211 (2)
C80.34070 (11)0.42315 (8)0.46985 (7)0.0215 (2)
C180.89056 (13)0.89912 (9)0.43551 (9)0.0306 (3)
H180.88310.90910.50190.037*0.588 (3)
H18A0.88650.91670.50110.037*0.412 (3)
N20.9309 (8)0.2578 (6)0.1571 (3)0.0206 (8)0.588 (3)
N30.8888 (10)0.9864 (5)0.3724 (9)0.0203 (11)0.588 (3)
C90.9283 (3)0.3491 (2)0.1046 (2)0.0259 (5)0.588 (3)
H90.91950.34260.03700.031*0.588 (3)
C100.9382 (2)0.45426 (16)0.1453 (2)0.0246 (4)0.588 (3)
H100.93930.51810.10580.029*0.588 (3)
C110.94634 (18)0.46501 (16)0.24375 (18)0.0202 (4)0.588 (3)
C120.9527 (2)0.36771 (18)0.29764 (18)0.0260 (5)0.588 (3)
H120.96240.37090.36540.031*0.588 (3)
C130.9446 (4)0.2666 (3)0.2511 (2)0.0240 (6)0.588 (3)
H130.94910.20080.28830.029*0.588 (3)
C140.9425 (2)0.57258 (15)0.29274 (13)0.0245 (5)0.588 (3)
H140.95380.57240.36060.029*0.588 (3)
C150.9246 (2)0.66976 (15)0.24941 (15)0.0241 (4)0.588 (3)
H150.91700.66920.18160.029*0.588 (3)
C160.9152 (3)0.7790 (2)0.2963 (2)0.0182 (5)0.588 (3)
C170.9045 (7)0.7916 (5)0.3934 (2)0.0242 (8)0.588 (3)
H170.90640.72780.43300.029*0.588 (3)
C190.9010 (9)0.9740 (6)0.2814 (5)0.0214 (8)0.588 (3)
H190.89971.03810.24220.026*0.588 (3)
C200.9153 (4)0.8733 (3)0.2402 (3)0.0244 (6)0.588 (3)
H200.92540.86780.17380.029*0.588 (3)
C17A0.9027 (10)0.7907 (7)0.4220 (4)0.0258 (10)0.412 (3)
H17A0.90260.73880.47280.031*0.412 (3)
C9A0.9486 (4)0.3433 (3)0.0717 (3)0.0219 (7)0.412 (3)
H9A0.95500.32590.00640.026*0.412 (3)
C20A0.9161 (6)0.8429 (4)0.2607 (4)0.0260 (11)0.412 (3)
H20A0.92750.82650.19580.031*0.412 (3)
N2A0.9319 (11)0.2579 (10)0.1328 (4)0.0202 (10)0.412 (3)
N3A0.8830 (15)0.9861 (9)0.3829 (13)0.025 (2)0.412 (3)
C19A0.8995 (15)0.9532 (9)0.2902 (9)0.034 (2)0.412 (3)
H19A0.89961.00940.24280.040*0.412 (3)
C10A0.9569 (3)0.4532 (2)0.0982 (3)0.0243 (6)0.412 (3)
H10A0.96630.50870.05140.029*0.412 (3)
C11A0.9515 (3)0.4826 (2)0.1934 (3)0.0195 (6)0.412 (3)
C12A0.9434 (3)0.3974 (3)0.2586 (3)0.0250 (6)0.412 (3)
H12A0.94480.41250.32500.030*0.412 (3)
C13A0.9330 (6)0.2880 (4)0.2245 (4)0.0293 (10)0.412 (3)
H13A0.92620.23090.27030.035*0.412 (3)
C14A0.9493 (3)0.6007 (2)0.21878 (19)0.0235 (6)0.412 (3)
H14A0.96760.65260.17090.028*0.412 (3)
C15A0.9237 (3)0.6405 (2)0.3033 (2)0.0226 (6)0.412 (3)
H15A0.90950.58840.35210.027*0.412 (3)
C16A0.9155 (4)0.7585 (4)0.3276 (3)0.0186 (7)0.412 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0508 (6)0.0126 (3)0.0286 (4)0.0008 (3)0.0170 (4)0.0002 (3)
O20.0459 (5)0.0155 (3)0.0195 (3)0.0059 (3)0.0096 (3)0.0016 (3)
O30.0510 (6)0.0143 (3)0.0270 (4)0.0041 (3)0.0012 (4)0.0046 (3)
O40.0438 (5)0.0149 (3)0.0201 (3)0.0063 (3)0.0006 (3)0.0003 (3)
N10.0510 (7)0.0180 (4)0.0186 (4)0.0067 (4)0.0058 (4)0.0018 (3)
C10.0246 (5)0.0175 (4)0.0187 (4)0.0010 (4)0.0046 (4)0.0022 (3)
C20.0255 (5)0.0148 (4)0.0210 (4)0.0017 (4)0.0039 (4)0.0038 (3)
C30.0242 (5)0.0130 (4)0.0206 (4)0.0003 (3)0.0030 (4)0.0012 (3)
C40.0269 (5)0.0142 (4)0.0191 (4)0.0002 (4)0.0047 (4)0.0016 (3)
C50.0235 (5)0.0130 (4)0.0206 (4)0.0001 (3)0.0056 (4)0.0026 (3)
C60.0236 (5)0.0140 (4)0.0213 (4)0.0010 (3)0.0050 (4)0.0006 (3)
C70.0285 (5)0.0142 (4)0.0214 (4)0.0004 (4)0.0069 (4)0.0025 (3)
C80.0285 (5)0.0145 (4)0.0217 (5)0.0002 (4)0.0025 (4)0.0023 (3)
C180.0394 (7)0.0178 (5)0.0360 (6)0.0017 (4)0.0118 (5)0.0001 (4)
N20.0261 (11)0.0147 (9)0.021 (2)0.0007 (7)0.0014 (18)0.0088 (18)
N30.0306 (19)0.0099 (16)0.022 (3)0.0050 (11)0.0112 (14)0.0001 (12)
C90.0351 (14)0.0194 (9)0.0238 (13)0.0024 (8)0.0066 (10)0.0027 (10)
C100.0400 (12)0.0158 (8)0.0182 (11)0.0012 (7)0.0044 (9)0.0006 (8)
C110.0232 (9)0.0158 (10)0.0219 (11)0.0012 (6)0.0037 (7)0.0024 (7)
C120.0388 (12)0.0170 (9)0.0225 (10)0.0016 (8)0.0038 (9)0.0012 (8)
C130.0341 (13)0.0160 (13)0.0225 (15)0.0007 (10)0.0055 (12)0.0034 (9)
C140.0348 (11)0.0173 (9)0.0218 (8)0.0012 (7)0.0053 (7)0.0064 (6)
C150.0325 (10)0.0176 (8)0.0223 (9)0.0004 (7)0.0021 (7)0.0056 (7)
C160.0226 (9)0.0109 (14)0.0211 (13)0.0001 (8)0.0021 (10)0.0004 (10)
C170.0346 (13)0.0133 (9)0.026 (2)0.0011 (8)0.0086 (18)0.0038 (17)
C190.0301 (15)0.0192 (19)0.0155 (15)0.0019 (14)0.0054 (11)0.0047 (15)
C200.0324 (12)0.0204 (16)0.0205 (14)0.0012 (12)0.0019 (10)0.0034 (10)
C17A0.0330 (18)0.0195 (15)0.027 (3)0.0003 (12)0.011 (3)0.005 (2)
C9A0.0281 (17)0.0136 (11)0.0247 (18)0.0015 (10)0.0065 (14)0.0010 (13)
C20A0.0378 (18)0.019 (3)0.021 (2)0.0028 (19)0.0022 (17)0.0085 (17)
N2A0.0234 (15)0.0201 (13)0.017 (3)0.0010 (10)0.001 (2)0.010 (2)
N3A0.026 (3)0.033 (4)0.016 (3)0.001 (2)0.008 (2)0.011 (2)
C19A0.039 (3)0.029 (4)0.032 (3)0.002 (3)0.0015 (19)0.006 (2)
C10A0.0320 (15)0.0166 (11)0.0243 (15)0.0019 (10)0.0035 (12)0.0024 (10)
C11A0.0250 (13)0.0163 (11)0.0170 (15)0.0012 (9)0.0008 (10)0.0038 (11)
C12A0.0386 (17)0.0155 (16)0.0209 (15)0.0010 (11)0.0017 (12)0.0020 (11)
C13A0.041 (2)0.019 (2)0.027 (3)0.0004 (15)0.0012 (19)0.0024 (15)
C14A0.0299 (14)0.0125 (10)0.0283 (13)0.0003 (9)0.0033 (10)0.0035 (9)
C15A0.0308 (14)0.0119 (12)0.0251 (14)0.0007 (9)0.0020 (10)0.0013 (9)
C16A0.0207 (13)0.0107 (14)0.024 (2)0.0002 (10)0.0012 (14)0.0033 (15)
Geometric parameters (Å, º) top
O1—C71.2209 (12)C12—H120.9500
O2—H20.990 (19)C12—C131.385 (4)
O2—C71.3222 (12)C13—H130.9500
O3—C81.2274 (12)C14—H140.9500
O4—H40.98 (2)C14—C151.327 (3)
O4—C81.3191 (12)C15—H150.9500
N1—H1A0.899 (17)C15—C161.482 (3)
N1—H1B0.894 (17)C16—C171.387 (4)
N1—C11.3775 (13)C16—C201.385 (3)
C1—C21.4017 (14)C17—H170.9500
C1—C61.4005 (13)C19—H190.9500
C2—H2A0.9500C19—C201.360 (7)
C2—C31.3912 (14)C20—H200.9500
C3—C41.3991 (13)C17A—H17A0.9500
C3—C81.4979 (14)C17A—C16A1.399 (6)
C4—H4A0.9500C9A—H9A0.9500
C4—C51.4014 (13)C9A—N2A1.361 (10)
C5—C61.3902 (14)C9A—C10A1.379 (4)
C5—C71.4948 (13)C20A—H20A0.9500
C6—H60.9500C20A—C19A1.410 (11)
C18—H180.9500C20A—C16A1.388 (5)
C18—H18A0.9500N2A—C13A1.338 (7)
C18—N31.376 (9)N3A—C19A1.39 (2)
C18—C171.439 (5)C19A—H19A0.9500
C18—C17A1.331 (9)C10A—H10A0.9500
C18—N3A1.283 (13)C10A—C11A1.390 (5)
N2—C91.326 (7)C11A—C12A1.385 (4)
N2—C131.320 (5)C11A—C14A1.472 (4)
N3—C191.305 (13)C12A—H12A0.9500
C9—H90.9500C12A—C13A1.406 (6)
C9—C101.392 (3)C13A—H13A0.9500
C10—H100.9500C14A—H14A0.9500
C10—C111.386 (3)C14A—C15A1.329 (4)
C11—C121.397 (3)C15A—H15A0.9500
C11—C141.472 (2)C15A—C16A1.469 (5)
C7—O2—H2107.5 (11)C15—C14—C11125.02 (18)
C8—O4—H4111.7 (11)C15—C14—H14117.5
H1A—N1—H1B116.4 (15)C14—C15—H15116.7
C1—N1—H1A119.4 (11)C14—C15—C16126.5 (2)
C1—N1—H1B116.6 (10)C16—C15—H15116.7
N1—C1—C2121.17 (9)C17—C16—C15123.3 (3)
N1—C1—C6120.72 (9)C20—C16—C15118.4 (3)
C6—C1—C2118.07 (9)C20—C16—C17118.3 (4)
C1—C2—H2A119.5C18—C17—H17119.2
C3—C2—C1121.01 (9)C16—C17—C18121.5 (4)
C3—C2—H2A119.5C16—C17—H17119.2
C2—C3—C4120.80 (9)N3—C19—H19118.6
C2—C3—C8117.74 (8)N3—C19—C20122.9 (6)
C4—C3—C8121.44 (9)C20—C19—H19118.6
C3—C4—H4A120.9C16—C20—H20120.4
C3—C4—C5118.24 (9)C19—C20—C16119.2 (4)
C5—C4—H4A120.9C19—C20—H20120.4
C4—C5—C7122.17 (9)C18—C17A—H17A122.4
C6—C5—C4120.90 (9)C18—C17A—C16A115.3 (5)
C6—C5—C7116.93 (8)C16A—C17A—H17A122.4
C1—C6—H6119.5N2A—C9A—H9A117.7
C5—C6—C1120.93 (9)N2A—C9A—C10A124.5 (5)
C5—C6—H6119.5C10A—C9A—H9A117.7
O1—C7—O2123.09 (9)C19A—C20A—H20A120.4
O1—C7—C5121.82 (9)C16A—C20A—H20A120.4
O2—C7—C5115.09 (8)C16A—C20A—C19A119.2 (6)
O3—C8—O4123.31 (9)C13A—N2A—C9A114.3 (9)
O3—C8—C3122.38 (9)C18—N3A—C19A107.5 (10)
O4—C8—C3114.30 (8)C20A—C19A—H19A117.5
N3—C18—H18122.5N3A—C19A—C20A125.0 (9)
N3—C18—C17115.0 (5)N3A—C19A—H19A117.5
C17—C18—H18122.5C9A—C10A—H10A120.1
C17A—C18—H18A111.8C9A—C10A—C11A119.9 (3)
N3A—C18—H18A111.8C11A—C10A—H10A120.1
N3A—C18—C17A136.5 (8)C10A—C11A—C14A118.9 (3)
C13—N2—C9119.0 (5)C12A—C11A—C10A117.2 (2)
C19—N3—C18123.1 (6)C12A—C11A—C14A123.8 (3)
N2—C9—H9118.9C11A—C12A—H12A120.7
N2—C9—C10122.3 (3)C11A—C12A—C13A118.6 (3)
C10—C9—H9118.9C13A—C12A—H12A120.7
C9—C10—H10120.3N2A—C13A—C12A125.3 (6)
C11—C10—C9119.4 (2)N2A—C13A—H13A117.4
C11—C10—H10120.3C12A—C13A—H13A117.4
C10—C11—C12117.31 (16)C11A—C14A—H14A117.4
C10—C11—C14123.2 (2)C15A—C14A—C11A125.2 (3)
C12—C11—C14119.4 (2)C15A—C14A—H14A117.4
C11—C12—H12120.4C14A—C15A—H15A117.3
C13—C12—C11119.2 (2)C14A—C15A—C16A125.3 (3)
C13—C12—H12120.4C16A—C15A—H15A117.3
N2—C13—C12122.7 (4)C17A—C16A—C15A120.1 (5)
N2—C13—H13118.6C20A—C16A—C17A116.4 (5)
C12—C13—H13118.6C20A—C16A—C15A123.5 (4)
C11—C14—H14117.5
N1—C1—C2—C3178.19 (10)C11—C14—C15—C16177.6 (2)
N1—C1—C6—C5179.82 (10)C12—C11—C14—C15173.6 (2)
C1—C2—C3—C41.71 (16)C13—N2—C9—C100.7 (9)
C1—C2—C3—C8176.64 (10)C14—C11—C12—C13174.4 (3)
C2—C1—C6—C52.05 (16)C14—C15—C16—C1710.0 (5)
C2—C3—C4—C52.20 (16)C14—C15—C16—C20170.8 (3)
C2—C3—C8—O37.84 (17)C15—C16—C17—C18177.6 (3)
C2—C3—C8—O4171.27 (10)C15—C16—C20—C19177.1 (5)
C3—C4—C5—C60.59 (16)C17—C18—N3—C191.1 (12)
C3—C4—C5—C7179.15 (10)C17—C18—C17A—C16A1.4 (17)
C4—C3—C8—O3173.81 (11)C17—C18—N3A—C19A3.8 (15)
C4—C3—C8—O47.07 (15)C17—C16—C20—C192.0 (7)
C4—C5—C6—C11.56 (16)C20—C16—C17—C181.5 (7)
C4—C5—C7—O1165.59 (11)C17A—C18—N3—C190.5 (14)
C4—C5—C7—O214.70 (15)C17A—C18—C17—C16179 (3)
C6—C1—C2—C30.43 (16)C17A—C18—N3A—C19A4.3 (18)
C6—C5—C7—O114.15 (16)C9A—N2A—C13A—C12A3.1 (13)
C6—C5—C7—O2165.55 (10)C9A—C10A—C11A—C12A2.7 (4)
C7—C5—C6—C1178.69 (10)C9A—C10A—C11A—C14A174.9 (3)
C8—C3—C4—C5176.09 (10)N2A—C9A—C10A—C11A1.6 (8)
C18—N3—C19—C200.6 (15)N3A—C18—N3—C19159 (11)
C18—C17A—C16A—C20A0.9 (9)N3A—C18—C17—C162.5 (10)
C18—C17A—C16A—C15A177.3 (5)N3A—C18—C17A—C16A2.8 (15)
C18—N3A—C19A—C20A2 (2)C19A—C20A—C16A—C17A2.1 (11)
N2—C9—C10—C112.3 (6)C19A—C20A—C16A—C15A176.0 (8)
N3—C18—C17—C160.0 (8)C10A—C9A—N2A—C13A4.4 (12)
N3—C18—C17A—C16A0.3 (12)C10A—C11A—C12A—C13A3.8 (5)
N3—C18—N3A—C19A19 (9)C10A—C11A—C14A—C15A168.9 (3)
N3—C19—C20—C161.0 (12)C11A—C12A—C13A—N2A0.9 (9)
C9—N2—C13—C121.9 (9)C11A—C14A—C15A—C16A177.1 (3)
C9—C10—C11—C124.0 (3)C12A—C11A—C14A—C15A8.5 (5)
C9—C10—C11—C14173.2 (2)C14A—C11A—C12A—C13A173.6 (4)
C10—C11—C12—C132.9 (3)C14A—C15A—C16A—C17A172.8 (5)
C10—C11—C14—C153.5 (3)C14A—C15A—C16A—C20A9.1 (6)
C11—C12—C13—N20.1 (6)C16A—C20A—C19A—N3A0.5 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.899 (17)2.062 (17)2.9540 (13)171.0 (15)
N1—H1B···O3ii0.894 (17)2.157 (17)3.0500 (13)178.6 (13)
O2—H2···N3iii0.989 (19)1.70 (2)2.688 (8)173.4 (18)
O2—H2···N3Aiii0.989 (19)1.63 (2)2.619 (12)177 (2)
O4—H4···N2iv0.98 (2)1.72 (2)2.702 (7)173.2 (19)
O4—H4···N2Aiv0.98 (2)1.59 (2)2.566 (11)175 (2)
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y+2, z+1; (iv) x1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.899 (17)2.062 (17)2.9540 (13)171.0 (15)
N1—H1B···O3ii0.894 (17)2.157 (17)3.0500 (13)178.6 (13)
O2—H2···N3iii0.989 (19)1.70 (2)2.688 (8)173.4 (18)
O2—H2···N3Aiii0.989 (19)1.63 (2)2.619 (12)177 (2)
O4—H4···N2iv0.98 (2)1.72 (2)2.702 (7)173.2 (19)
O4—H4···N2Aiv0.98 (2)1.59 (2)2.566 (11)175 (2)
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+1/2, y+1/2, z+1/2; (iii) x+1, y+2, z+1; (iv) x1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC12H10N2·C8H7NO4
Mr363.36
Crystal system, space groupMonoclinic, P21/n
Temperature (K)90
a, b, c (Å)10.1614 (10), 12.0782 (12), 14.0537 (14)
β (°) 95.027 (2)
V3)1718.2 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.22 × 0.2 × 0.18
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2014)
Tmin, Tmax0.683, 0.747
No. of measured, independent and
observed [I > 2σ(I)] reflections
24372, 6546, 4519
Rint0.033
(sin θ/λ)max1)0.771
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.143, 1.02
No. of reflections6546
No. of parameters378
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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.

References

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Volume 72| Part 5| May 2016| Pages 639-642
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