N,N′-Bis(4-hy­droxy­phen­yl)pyridine-2,6-dicarboxamide di­methyl­formamide monosolvate

Waris, G.; Siddiqi, H.M.; Flörke, U.; Hussain, R.; Butt, M.S.

doi:10.1107/S1600536813013810

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o991

doi:10.1107/S1600536813013810

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N,N′-Bis(4-hydroxyphenyl)pyridine-2,6-dicarboxamide dimethylformamide monosolvate

Ghulam Waris,^a Humaira Masood Siddiqi,^a ^* Ulrich Flörke,^b Rizwan Hussain ^c and M. Saeed Butt ^a

^aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, ^bUniversität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany, and ^cNESCOM, PO Box 2216 Islamabad, Pakistan
^*Correspondence e-mail: Humaira_siddiqi@yahoo.com

(Received 15 May 2013; accepted 19 May 2013; online 31 May 2013)

The molecular structure of the pyridine derivative, C₁₉H₁₅N₃O₄·C₃H₇NO, shows almost planar geometry with dihedral angles of 6.9 (1) and 13.4 (1)° between the pyridine ring and the two benzene rings. This conformation is stabilized by two intramolecular N—H⋯N(pyridine) bonds. In the crystal, strong O—H⋯O(carboxamide) and N—H⋯O(hydroxyphenyl) hydrogen bonds link the molecules, forming a three-dimensional structure. The dimethylformamide solvent molecules are not involved in the hydrogen bonding. The structure shows pseudosymmetry, but refinement in the space group Pbcn leads to significantly worse results and a disordered dimethylformamide molecule.

Related literature

For applications of aromatic polyamides, see: Hamciuc et al., (2001 ); Yang et al. (1998 ); Diakoumakos & Mikroyannidis (1994 ); Ebadi & Mehdipour-Ataei (2010 ). For the structure of a related Co-complex, see: Ali et al. (2012 ).

Experimental

Crystal data

C₁₉H₁₅N₃O₄·C₃H₇NO
M_r = 422.44
Orthorhombic, P c a 2₁
a = 16.8124 (12) Å
b = 10.9545 (8) Å
c = 10.9331 (7) Å
V = 2013.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 130 K
0.47 × 0.41 × 0.39 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.954, T_max = 0.962
18386 measured reflections
2536 independent reflections
2434 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.099
S = 1.03
2536 reflections
284 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N1	0.88	2.20	2.661 (2)	113
N3—H3A⋯N1	0.88	2.22	2.675 (2)	112
O2—H2⋯O1ⁱ	0.84	1.92	2.7572 (19)	179
O4—H4⋯O3ⁱⁱ	0.84	1.91	2.7464 (19)	172
N2—H2B⋯O2ⁱⁱⁱ	0.88	2.44	3.125 (2)	135
N3—H3A⋯O4^iv	0.88	2.41	3.043 (2)	130
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+1, z]$ ; (ii) $[x+{\script{1\over 2}}, -y+2, z]$ ; (iii) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (iv) $[-x+1, -y+2, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813013810/bt6908sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013810/bt6908Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813013810/bt6908Isup3.cml

checkCIF report

Comment top

Aromatic polyamides' application in novel technologies has grown rapidly due to their usage as a beneficial alternative for metals and other goods (Yang, et al., 1998, Hamciuc et al., 2001). The company of amide linkages makes them strong applicant for semi-permeable membrane as they are hydrophilic polymers and water absorbent. In addition their high tech artificial fibre usage in the production of defensive attire of protective firemen, soldiers, race car drivers and gas filteration makes them prominent among others (Ebadi, et al., 2010, Diakoumakos et al., 1994). As part of our ongoing research in solubility of aromatic poly(amide-imide)s by structural modification, we are reporting a pyridine-based monomer having inbuilt amide functionality. It enhances the solubility of resulting poly(amid-imide)s without deteriorating the inherent properties of the polymer.

Related literature top

For applications of aromatic polyamides, see: Hamciuc et al., (2001); Yang et al. (1998); Diakoumakos & Mikroyannidis (1994); Ebadi & Mehdipour-Ataei (2010). For the structure of a related Co-complex, see: Ali et al. (2012).

Experimental top

This preparation was carried out by using reagent grade quality chemicals without their further purification. In a 100 ml, three necked, round bottomed flask, equipped with a condenser, a nitrogen gas inlet tube, a thermometer and a magnetic stirrer, 0.02mole (2.18 g m) of 4-hydroxyaniline in 30 mL of dry tetrahydrofuran(THF) stirred at 273–278 K for 30 minutes and 0.01 mol (2.04 g m) of pyridine -2,6-dicarbonyl dichloride in 35 mL of THF was added dropwise by dropping funnel and stirring was continued for further 1 h under same conditions. The temperature of reaction mixture was then raised to 308–313 K and stirring was continued for 30 minutes. The flask content was cooled to room temperature, poured into water and let it for 24 h. Resulting purplish precipitates were filtered, washed with hot water and 5% NaOH solution. Finally, product was washed with hot water and methanol, dried under vacuum at 80°C. The crude product was recrystallized from tetrahydrofuran and dimethylformamide(4:1).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

	Fig. 1. Molecular structure of the title compound with anisotropic displacement parameters drawn at the 50% probability level.
	Fig. 2. Crystal packing viewed along b axis with intermolecular hydrogen bonds as dotted lines. H-atoms not involved are omitted.

N,N'-Bis(4-hydroxyphenyl)pyridine-2,6-dicarboxamide dimethylformamide monosolvate top

Crystal data top

C₁₉H₁₅N₃O₄·C₃H₇NO	D_x = 1.393 Mg m⁻³
M_r = 422.44	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca2₁	Cell parameters from 8531 reflections
a = 16.8124 (12) Å	θ = 2.2–28.3°
b = 10.9545 (8) Å	µ = 0.10 mm⁻¹
c = 10.9331 (7) Å	T = 130 K
V = 2013.6 (2) Å³	Prism, pale-pink
Z = 4	0.47 × 0.41 × 0.39 mm
F(000) = 888

Data collection top

Bruker SMART APEX diffractometer	2536 independent reflections
Radiation source: sealed tube	2434 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 27.9°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −22→22
T_min = 0.954, T_max = 0.962	k = −14→14
18386 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: difference Fourier map
wR(F²) = 0.099	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0683P)² + 0.4544P] where P = (F_o² + 2F_c²)/3
2536 reflections	(Δ/σ)_max < 0.001
284 parameters	Δρ_max = 0.33 e Å⁻³
1 restraint	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₉H₁₅N₃O₄·C₃H₇NO	V = 2013.6 (2) Å³
M_r = 422.44	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 16.8124 (12) Å	µ = 0.10 mm⁻¹
b = 10.9545 (8) Å	T = 130 K
c = 10.9331 (7) Å	0.47 × 0.41 × 0.39 mm

Data collection top

Bruker SMART APEX diffractometer	2536 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2434 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.962	R_int = 0.022
18386 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.099	H-atom parameters constrained
S = 1.03	Δρ_max = 0.33 e Å⁻³
2536 reflections	Δρ_min = −0.32 e Å⁻³
284 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.22086 (7)	0.57263 (12)	0.50884 (13)	0.0191 (3)
O2	0.58528 (7)	0.39649 (13)	0.37035 (15)	0.0215 (3)
H2	0.6268	0.4049	0.4122	0.032*
O3	0.22824 (7)	0.93446 (12)	1.04434 (13)	0.0202 (3)
O4	0.59295 (8)	1.09650 (14)	1.18167 (15)	0.0242 (3)
H4	0.6353	1.0812	1.1440	0.036*
N1	0.25192 (7)	0.75080 (13)	0.77701 (18)	0.0152 (2)
N2	0.33363 (8)	0.62143 (14)	0.61383 (17)	0.0183 (3)
H2B	0.3500	0.6615	0.6789	0.022*
N3	0.33916 (8)	0.87656 (14)	0.93824 (16)	0.0180 (3)
H3A	0.3544	0.8341	0.8741	0.022*
C1	0.08639 (9)	0.7555 (2)	0.7806 (2)	0.0224 (3)
H1A	0.0299	0.7566	0.7819	0.027*
C2	0.12663 (10)	0.69108 (18)	0.69062 (19)	0.0189 (4)
H2A	0.0984	0.6479	0.6291	0.023*
C3	0.20912 (10)	0.69128 (16)	0.69270 (17)	0.0153 (3)
C4	0.12932 (10)	0.81813 (18)	0.8684 (2)	0.0193 (4)
H4A	0.1031	0.8635	0.9305	0.023*
C5	0.21208 (10)	0.81302 (15)	0.86329 (17)	0.0152 (3)
C6	0.25491 (11)	0.62261 (14)	0.59558 (19)	0.0152 (3)
C7	0.39446 (10)	0.56544 (16)	0.54420 (19)	0.0165 (4)
C8	0.38133 (10)	0.48237 (17)	0.44972 (19)	0.0188 (4)
H8A	0.3286	0.4630	0.4253	0.023*
C9	0.44580 (10)	0.42785 (18)	0.3914 (2)	0.0192 (4)
H9A	0.4369	0.3711	0.3271	0.023*
C10	0.52331 (10)	0.45623 (16)	0.42674 (19)	0.0170 (4)
C11	0.53648 (10)	0.54289 (17)	0.51766 (19)	0.0181 (4)
H11A	0.5892	0.5652	0.5395	0.022*
C12	0.47240 (10)	0.59636 (17)	0.57604 (19)	0.0180 (4)
H12A	0.4815	0.6549	0.6386	0.022*
C13	0.26050 (10)	0.88030 (15)	0.95796 (19)	0.0157 (4)
C14	0.40125 (10)	0.93161 (17)	1.00651 (19)	0.0165 (4)
C15	0.38915 (11)	1.02561 (18)	1.0904 (2)	0.0202 (4)
H15A	0.3369	1.0536	1.1075	0.024*
C16	0.45424 (12)	1.07814 (19)	1.1488 (2)	0.0214 (4)
H16A	0.4460	1.1425	1.2057	0.026*
C17	0.53075 (10)	1.03808 (18)	1.12533 (19)	0.0186 (4)
C18	0.54283 (11)	0.94174 (19)	1.0435 (2)	0.0204 (4)
H18A	0.5950	0.9121	1.0286	0.024*
C19	0.47829 (10)	0.88971 (17)	0.9842 (2)	0.0198 (4)
H19A	0.4866	0.8249	0.9278	0.024*
O100	0.33017 (10)	0.30965 (16)	0.17286 (19)	0.0424 (4)
N100	0.21891 (10)	0.2555 (2)	0.2759 (3)	0.0341 (4)
C100	0.25928 (14)	0.31580 (19)	0.1894 (3)	0.0342 (5)
H100	0.2297	0.3678	0.1368	0.041*
C101	0.2617 (2)	0.1731 (3)	0.3556 (4)	0.0661 (10)
H101	0.2472	0.0887	0.3361	0.099*
H102	0.2479	0.1907	0.4409	0.099*
H103	0.3191	0.1841	0.3438	0.099*
C102	0.13354 (17)	0.2626 (4)	0.2881 (5)	0.0805 (13)
H104	0.1127	0.3235	0.2308	0.121*
H105	0.1199	0.2864	0.3719	0.121*
H106	0.1101	0.1828	0.2699	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0161 (5)	0.0232 (6)	0.0180 (7)	0.0000 (5)	−0.0017 (5)	−0.0037 (6)
O2	0.0134 (6)	0.0297 (7)	0.0215 (7)	0.0051 (5)	0.0001 (6)	−0.0053 (6)
O3	0.0157 (6)	0.0250 (6)	0.0200 (7)	−0.0009 (5)	0.0019 (6)	−0.0036 (6)
O4	0.0147 (6)	0.0375 (8)	0.0204 (8)	−0.0070 (5)	0.0008 (6)	−0.0074 (7)
N1	0.0134 (5)	0.0171 (5)	0.0150 (6)	−0.0018 (8)	0.0006 (8)	0.0015 (4)
N2	0.0137 (7)	0.0237 (7)	0.0175 (8)	0.0013 (5)	−0.0002 (6)	−0.0057 (7)
N3	0.0144 (7)	0.0224 (7)	0.0171 (8)	−0.0006 (5)	0.0008 (7)	−0.0045 (7)
C1	0.0121 (6)	0.0301 (8)	0.0252 (8)	0.0008 (8)	0.0013 (9)	−0.0048 (7)
C2	0.0161 (8)	0.0226 (8)	0.0182 (10)	−0.0017 (6)	−0.0024 (7)	−0.0035 (8)
C3	0.0148 (7)	0.0169 (7)	0.0142 (9)	0.0005 (6)	0.0004 (7)	0.0006 (7)
C4	0.0145 (7)	0.0239 (9)	0.0195 (9)	0.0023 (6)	0.0010 (7)	−0.0025 (8)
C5	0.0148 (7)	0.0157 (7)	0.0151 (9)	−0.0001 (6)	−0.0006 (7)	0.0018 (7)
C6	0.0141 (7)	0.0159 (7)	0.0156 (9)	−0.0003 (6)	−0.0004 (7)	0.0023 (7)
C7	0.0131 (7)	0.0198 (8)	0.0167 (9)	0.0020 (6)	0.0002 (7)	0.0014 (8)
C8	0.0133 (7)	0.0232 (8)	0.0201 (10)	−0.0011 (6)	−0.0011 (7)	−0.0028 (8)
C9	0.0176 (8)	0.0226 (9)	0.0173 (8)	0.0008 (7)	−0.0021 (7)	−0.0025 (7)
C10	0.0146 (7)	0.0197 (8)	0.0167 (9)	0.0023 (6)	0.0005 (7)	0.0011 (8)
C11	0.0136 (7)	0.0213 (8)	0.0193 (9)	0.0008 (6)	−0.0022 (7)	−0.0001 (7)
C12	0.0167 (8)	0.0202 (8)	0.0172 (10)	−0.0002 (6)	−0.0015 (7)	−0.0023 (7)
C13	0.0145 (8)	0.0159 (7)	0.0167 (9)	−0.0007 (6)	−0.0015 (7)	0.0018 (7)
C14	0.0126 (7)	0.0205 (8)	0.0163 (9)	−0.0016 (6)	−0.0007 (7)	−0.0013 (7)
C15	0.0143 (7)	0.0245 (8)	0.0217 (9)	0.0006 (7)	0.0007 (7)	−0.0041 (8)
C16	0.0193 (8)	0.0250 (9)	0.0198 (10)	−0.0030 (7)	0.0002 (8)	−0.0063 (8)
C17	0.0161 (8)	0.0251 (9)	0.0148 (9)	−0.0052 (6)	−0.0002 (7)	0.0014 (8)
C18	0.0138 (7)	0.0245 (8)	0.0228 (9)	−0.0003 (6)	0.0013 (8)	−0.0009 (8)
C19	0.0168 (8)	0.0205 (8)	0.0220 (10)	−0.0002 (6)	0.0019 (7)	−0.0031 (7)
O100	0.0323 (8)	0.0469 (10)	0.0478 (11)	−0.0081 (7)	0.0065 (8)	0.0085 (9)
N100	0.0273 (8)	0.0307 (8)	0.0442 (10)	−0.0010 (8)	0.0072 (11)	−0.0014 (7)
C100	0.0339 (11)	0.0272 (9)	0.0415 (14)	0.0009 (9)	−0.0054 (11)	0.0063 (11)
C101	0.069 (2)	0.076 (2)	0.053 (2)	−0.0001 (18)	0.0106 (18)	0.0381 (19)
C102	0.0282 (13)	0.089 (3)	0.124 (4)	−0.0040 (15)	0.026 (2)	−0.037 (3)

Geometric parameters (Å, º) top

O1—C6	1.236 (2)	C9—C10	1.394 (2)
O2—C10	1.376 (2)	C9—H9A	0.9500
O2—H2	0.8400	C10—C11	1.392 (3)
O3—C13	1.240 (2)	C11—C12	1.382 (3)
O4—C17	1.372 (2)	C11—H11A	0.9500
O4—H4	0.8400	C12—H12A	0.9500
N1—C3	1.339 (2)	C14—C15	1.394 (3)
N1—C5	1.343 (2)	C14—C19	1.396 (2)
N2—C6	1.338 (2)	C15—C16	1.392 (3)
N2—C7	1.415 (2)	C15—H15A	0.9500
N2—H2B	0.8800	C16—C17	1.383 (3)
N3—C13	1.341 (2)	C16—H16A	0.9500
N3—C14	1.418 (2)	C17—C18	1.398 (3)
N3—H3A	0.8800	C18—C19	1.387 (3)
C1—C4	1.383 (3)	C18—H18A	0.9500
C1—C2	1.387 (3)	C19—H19A	0.9500
C1—H1A	0.9500	O100—C100	1.207 (3)
C2—C3	1.387 (2)	N100—C100	1.339 (3)
C2—H2A	0.9500	N100—C102	1.444 (3)
C3—C6	1.512 (3)	N100—C101	1.446 (4)
C4—C5	1.394 (2)	C100—H100	0.9500
C4—H4A	0.9500	C101—H101	0.9800
C5—C13	1.509 (2)	C101—H102	0.9800
C7—C8	1.394 (3)	C101—H103	0.9800
C7—C12	1.397 (2)	C102—H104	0.9800
C8—C9	1.392 (3)	C102—H105	0.9800
C8—H8A	0.9500	C102—H106	0.9800

C10—O2—H2	109.5	C11—C12—C7	120.87 (18)
C17—O4—H4	109.5	C11—C12—H12A	119.6
C3—N1—C5	117.56 (13)	C7—C12—H12A	119.6
C6—N2—C7	129.70 (17)	O3—C13—N3	124.65 (17)
C6—N2—H2B	115.2	O3—C13—C5	121.33 (15)
C7—N2—H2B	115.2	N3—C13—C5	114.01 (17)
C13—N3—C14	128.95 (17)	C15—C14—C19	119.57 (17)
C13—N3—H3A	115.5	C15—C14—N3	123.58 (16)
C14—N3—H3A	115.5	C19—C14—N3	116.83 (17)
C4—C1—C2	119.34 (15)	C16—C15—C14	119.53 (17)
C4—C1—H1A	120.3	C16—C15—H15A	120.2
C2—C1—H1A	120.3	C14—C15—H15A	120.2
C1—C2—C3	118.38 (18)	C17—C16—C15	120.99 (18)
C1—C2—H2A	120.8	C17—C16—H16A	119.5
C3—C2—H2A	120.8	C15—C16—H16A	119.5
N1—C3—C2	123.33 (17)	O4—C17—C16	118.52 (18)
N1—C3—C6	116.88 (15)	O4—C17—C18	121.91 (17)
C2—C3—C6	119.79 (17)	C16—C17—C18	119.55 (17)
C1—C4—C5	118.27 (19)	C19—C18—C17	119.72 (17)
C1—C4—H4A	120.9	C19—C18—H18A	120.1
C5—C4—H4A	120.9	C17—C18—H18A	120.1
N1—C5—C4	123.12 (18)	C18—C19—C14	120.62 (18)
N1—C5—C13	117.43 (15)	C18—C19—H19A	119.7
C4—C5—C13	119.45 (17)	C14—C19—H19A	119.7
O1—C6—N2	124.63 (18)	C100—N100—C102	122.9 (3)
O1—C6—C3	121.56 (16)	C100—N100—C101	118.78 (19)
N2—C6—C3	113.81 (17)	C102—N100—C101	118.2 (3)
C8—C7—C12	119.42 (17)	O100—C100—N100	125.4 (2)
C8—C7—N2	124.55 (16)	O100—C100—H100	117.3
C12—C7—N2	116.02 (17)	N100—C100—H100	117.3
C9—C8—C7	119.75 (16)	N100—C101—H101	109.5
C9—C8—H8A	120.1	N100—C101—H102	109.5
C7—C8—H8A	120.1	H101—C101—H102	109.5
C8—C9—C10	120.31 (18)	N100—C101—H103	109.5
C8—C9—H9A	119.8	H101—C101—H103	109.5
C10—C9—H9A	119.8	H102—C101—H103	109.5
O2—C10—C11	121.57 (16)	N100—C102—H104	109.5
O2—C10—C9	118.51 (17)	N100—C102—H105	109.5
C11—C10—C9	119.92 (17)	H104—C102—H105	109.5
C12—C11—C10	119.64 (17)	N100—C102—H106	109.5
C12—C11—H11A	120.2	H104—C102—H106	109.5
C10—C11—H11A	120.2	H105—C102—H106	109.5

C4—C1—C2—C3	0.5 (4)	C9—C10—C11—C12	2.8 (3)
C5—N1—C3—C2	0.0 (3)	C10—C11—C12—C7	−0.6 (3)
C5—N1—C3—C6	179.48 (14)	C8—C7—C12—C11	−2.0 (3)
C1—C2—C3—N1	−0.2 (3)	N2—C7—C12—C11	177.10 (18)
C1—C2—C3—C6	−179.65 (18)	C14—N3—C13—O3	−0.8 (3)
C2—C1—C4—C5	−0.5 (4)	C14—N3—C13—C5	178.39 (17)
C3—N1—C5—C4	−0.1 (3)	N1—C5—C13—O3	−176.12 (17)
C3—N1—C5—C13	−179.83 (14)	C4—C5—C13—O3	4.1 (3)
C1—C4—C5—N1	0.4 (3)	N1—C5—C13—N3	4.7 (2)
C1—C4—C5—C13	−179.91 (18)	C4—C5—C13—N3	−175.07 (18)
C7—N2—C6—O1	−0.7 (3)	C13—N3—C14—C15	−16.9 (3)
C7—N2—C6—C3	178.91 (17)	C13—N3—C14—C19	164.9 (2)
N1—C3—C6—O1	−174.51 (16)	C19—C14—C15—C16	1.3 (3)
C2—C3—C6—O1	5.0 (3)	N3—C14—C15—C16	−176.87 (19)
N1—C3—C6—N2	5.9 (2)	C14—C15—C16—C17	−0.3 (3)
C2—C3—C6—N2	−174.64 (18)	C15—C16—C17—O4	177.3 (2)
C6—N2—C7—C8	−10.6 (3)	C15—C16—C17—C18	−1.3 (3)
C6—N2—C7—C12	170.39 (19)	O4—C17—C18—C19	−176.8 (2)
C12—C7—C8—C9	2.4 (3)	C16—C17—C18—C19	1.8 (3)
N2—C7—C8—C9	−176.64 (18)	C17—C18—C19—C14	−0.8 (3)
C7—C8—C9—C10	−0.2 (3)	C15—C14—C19—C18	−0.8 (3)
C8—C9—C10—O2	177.25 (18)	N3—C14—C19—C18	177.52 (19)
C8—C9—C10—C11	−2.4 (3)	C102—N100—C100—O100	−177.4 (3)
O2—C10—C11—C12	−176.86 (19)	C101—N100—C100—O100	−1.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N1	0.88	2.20	2.661 (2)	113
N3—H3A···N1	0.88	2.22	2.675 (2)	112
O2—H2···O1ⁱ	0.84	1.92	2.7572 (19)	179
O4—H4···O3ⁱⁱ	0.84	1.91	2.7464 (19)	172
N2—H2B···O2ⁱⁱⁱ	0.88	2.44	3.125 (2)	135
N3—H3A···O4^iv	0.88	2.41	3.043 (2)	130

Symmetry codes: (i) x+1/2, −y+1, z; (ii) x+1/2, −y+2, z; (iii) −x+1, −y+1, z+1/2; (iv) −x+1, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅N₃O₄·C₃H₇NO
M_r	422.44
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	130
a, b, c (Å)	16.8124 (12), 10.9545 (8), 10.9331 (7)
V (Å³)	2013.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.47 × 0.41 × 0.39

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.954, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	18386, 2536, 2434
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.099, 1.03
No. of reflections	2536
No. of parameters	284
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.32

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N1	0.88	2.20	2.661 (2)	112.5
N3—H3A···N1	0.88	2.22	2.675 (2)	111.9
O2—H2···O1ⁱ	0.84	1.92	2.7572 (19)	178.8
O4—H4···O3ⁱⁱ	0.84	1.91	2.7464 (19)	172.0
N2—H2B···O2ⁱⁱⁱ	0.88	2.44	3.125 (2)	134.6
N3—H3A···O4^iv	0.88	2.41	3.043 (2)	129.6

Symmetry codes: (i) x+1/2, −y+1, z; (ii) x+1/2, −y+2, z; (iii) −x+1, −y+1, z+1/2; (iv) −x+1, −y+2, z−1/2.

Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for financial assistance and the Universität Paderborn, Germany, for carrying out XRD analysis.

References

Ali, A., Hundal, G. & Gupta, R. (2012). Cryst. Growth Des. 12, 1308–1319. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Diakoumakos, C. D. & Mikroyannidis, J. A. (1994). Polymer, 35, 1986–1990. CrossRef CAS Web of Science Google Scholar
Ebadi, H. & Mehdipour-Ataei, S. (2010). Chin. J. Polym. Sci. 28, 29–37. Web of Science CrossRef CAS Google Scholar
Hamciuc, E., Hamciuc, C., Sava, I. & Bruma, M. (2001). Eur. Polym. J. 37, 287–293. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, G., Jikei, M. & Kakimoto, M.-A. (1998). Macromolecules, 31, 5964–5966. Web of Science CrossRef CAS Google Scholar

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Volume 69| Part 6| June 2013| Page o991

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N,N′-Bis(4-hy­dr­oxy­phen­yl)pyridine-2,6-dicarboxamide di­methyl­formamide monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N,N′-Bis(4-hydroxyphenyl)pyridine-2,6-dicarboxamide dimethylformamide monosolvate