The 1:1 adduct of 3,5-dinitro­benzoic acid and quinoline

In the crystal structure of the title adduct, C₇H₄N₂O₆·C₉H₇N, the 3,5-dinitro­benzoic acid and quinoline mol­ecules are linked into a chain along the b axis by inter­molecular O—H...N and C—H...O hydrogen bonds. Adjacent chains are linked via C—H...O hydrogen bonds into layers parallel to the ab plane. A three-dimensional network is formed via π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.038
• wR factor = 0.111
• Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.17 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C7 H4 N2 O6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

3,5-dinitrobenzoic acid–quinoline (1/1)

Crystal data

C7H4N2O6·C9H7N	F(000) = 704
Mr = 341.28	Dx = 1.533 Mg m^−3
Monoclinic, P21/c	Melting point = 419–421 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.0358 (1) Å	Cell parameters from 5352 reflections
b = 14.3980 (3) Å	θ = 2.0–32.5°
c = 14.6002 (2) Å	µ = 0.12 mm^−1
β = 90.175 (1)°	T = 100 K
V = 1479.01 (4) Å^3	Block, colourless
Z = 4	0.52 × 0.42 × 0.39 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	5352 independent reflections
Radiation source: fine-focus sealed tube	4753 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.33 pixels mm^-1	θmax = 32.5°, θmin = 2.0°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −21→21
Tmin = 0.852, Tmax = 0.955	l = −22→21
31914 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0664P)^2 + 0.323P] where P = (Fo^2 + 2Fc^2)/3
5352 reflections	(Δ/σ)max = 0.001
270 parameters	Δρmax = 0.50 e Å^−3
1 restraint	Δρmin = −0.25 e Å^−3

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.31401 (11)	0.98505 (5)	0.08177 (5)	0.02949 (16)
O2	−0.03232 (11)	0.95559 (5)	0.13448 (7)	0.03518 (19)
O3	0.17857 (9)	0.63718 (4)	0.18772 (4)	0.01820 (12)
O4	−0.00812 (9)	0.52130 (4)	0.13711 (5)	0.01981 (13)
H1O4	0.088 (2)	0.4878 (13)	0.1509 (15)	0.073 (6)*
O5	−0.62653 (9)	0.59072 (5)	0.00605 (5)	0.02298 (14)
O6	−0.73098 (9)	0.73275 (5)	0.00127 (5)	0.02306 (14)
N1	−0.18889 (11)	0.93127 (5)	0.10641 (5)	0.02049 (15)
N2	−0.60903 (10)	0.67429 (5)	0.01951 (5)	0.01696 (13)
N3	0.28155 (10)	0.41459 (5)	0.17217 (5)	0.01526 (13)
C1	−0.22832 (11)	0.83093 (5)	0.10228 (5)	0.01514 (14)
C2	−0.08846 (11)	0.76953 (5)	0.13057 (5)	0.01478 (14)
H2	0.0313 (19)	0.7926 (9)	0.1531 (9)	0.023 (3)*
C3	−0.12201 (10)	0.67437 (5)	0.12261 (5)	0.01347 (13)
C4	−0.29261 (11)	0.64236 (5)	0.08534 (5)	0.01447 (14)
H4	−0.3143 (19)	0.5772 (10)	0.0760 (9)	0.027 (3)*
C5	−0.42896 (10)	0.70729 (6)	0.05966 (5)	0.01425 (13)
C6	−0.40238 (11)	0.80229 (6)	0.06743 (5)	0.01534 (14)
H6	−0.493 (2)	0.8460 (10)	0.0469 (9)	0.026 (3)*
C7	0.03170 (11)	0.60863 (5)	0.15275 (5)	0.01434 (14)
C8	0.44142 (12)	0.45415 (6)	0.19947 (6)	0.01717 (15)
H8	0.4366 (19)	0.5226 (10)	0.2050 (9)	0.028 (3)*
C9	0.60862 (11)	0.40396 (6)	0.22022 (6)	0.01785 (15)
H9	0.721 (2)	0.4395 (10)	0.2403 (10)	0.031 (3)*
C10	0.60637 (11)	0.30920 (6)	0.21134 (5)	0.01632 (14)
H10	0.718 (2)	0.2733 (10)	0.2241 (10)	0.032 (4)*
C11	0.43814 (11)	0.26431 (5)	0.18115 (5)	0.01360 (13)
C12	0.42687 (12)	0.16698 (6)	0.16800 (6)	0.01703 (15)
H12	0.540 (2)	0.1292 (9)	0.1786 (10)	0.026 (3)*
C13	0.25987 (13)	0.12703 (6)	0.13892 (6)	0.01879 (15)
H13	0.253 (2)	0.0602 (10)	0.1280 (10)	0.029 (3)*
C14	0.09811 (12)	0.18285 (6)	0.12081 (6)	0.01827 (15)
H14	−0.016 (2)	0.1548 (10)	0.1007 (10)	0.031 (3)*
C15	0.10584 (11)	0.27759 (6)	0.13095 (5)	0.01623 (14)
H15	−0.0030 (19)	0.3159 (9)	0.1163 (9)	0.025 (3)*
C16	0.27623 (10)	0.31990 (5)	0.16185 (5)	0.01327 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0333 (4)	0.0162 (3)	0.0389 (4)	0.0077 (3)	−0.0062 (3)	0.0001 (3)
O2	0.0265 (4)	0.0186 (3)	0.0603 (5)	−0.0058 (3)	−0.0087 (3)	−0.0012 (3)
O3	0.0147 (3)	0.0178 (3)	0.0221 (3)	0.0006 (2)	−0.0054 (2)	−0.0017 (2)
O4	0.0154 (3)	0.0125 (3)	0.0314 (3)	0.0005 (2)	−0.0050 (2)	−0.0003 (2)
O5	0.0192 (3)	0.0237 (3)	0.0260 (3)	−0.0036 (2)	−0.0036 (2)	−0.0053 (2)
O6	0.0136 (3)	0.0301 (3)	0.0254 (3)	0.0039 (2)	−0.0040 (2)	0.0044 (2)
N1	0.0228 (3)	0.0138 (3)	0.0248 (3)	0.0008 (3)	−0.0003 (3)	−0.0005 (2)
N2	0.0125 (3)	0.0227 (3)	0.0156 (3)	−0.0001 (2)	−0.0015 (2)	−0.0001 (2)
N3	0.0144 (3)	0.0137 (3)	0.0177 (3)	0.0010 (2)	−0.0010 (2)	−0.0001 (2)
C1	0.0166 (3)	0.0126 (3)	0.0162 (3)	0.0004 (2)	0.0002 (2)	−0.0002 (2)
C2	0.0139 (3)	0.0147 (3)	0.0157 (3)	−0.0003 (2)	−0.0009 (2)	−0.0008 (2)
C3	0.0125 (3)	0.0137 (3)	0.0142 (3)	0.0008 (2)	−0.0009 (2)	0.0002 (2)
C4	0.0135 (3)	0.0150 (3)	0.0149 (3)	0.0000 (2)	−0.0008 (2)	−0.0001 (2)
C5	0.0112 (3)	0.0178 (3)	0.0137 (3)	−0.0005 (2)	−0.0011 (2)	−0.0001 (2)
C6	0.0144 (3)	0.0170 (3)	0.0146 (3)	0.0025 (3)	0.0003 (2)	0.0005 (2)
C7	0.0136 (3)	0.0138 (3)	0.0156 (3)	0.0007 (2)	−0.0006 (2)	−0.0001 (2)
C8	0.0168 (3)	0.0154 (3)	0.0192 (3)	−0.0012 (3)	−0.0013 (3)	−0.0002 (3)
C9	0.0140 (3)	0.0190 (4)	0.0205 (3)	−0.0023 (3)	−0.0027 (3)	−0.0001 (3)
C10	0.0127 (3)	0.0189 (3)	0.0174 (3)	0.0008 (3)	−0.0021 (2)	0.0021 (3)
C11	0.0131 (3)	0.0143 (3)	0.0134 (3)	0.0007 (2)	−0.0009 (2)	0.0017 (2)
C12	0.0190 (3)	0.0146 (3)	0.0175 (3)	0.0020 (3)	−0.0007 (3)	0.0019 (3)
C13	0.0233 (4)	0.0143 (3)	0.0187 (3)	−0.0022 (3)	−0.0007 (3)	0.0008 (3)
C14	0.0171 (3)	0.0197 (4)	0.0181 (3)	−0.0042 (3)	−0.0015 (3)	−0.0004 (3)
C15	0.0132 (3)	0.0187 (3)	0.0168 (3)	−0.0007 (3)	−0.0017 (2)	−0.0001 (3)
C16	0.0123 (3)	0.0142 (3)	0.0133 (3)	0.0004 (2)	−0.0006 (2)	0.0005 (2)

Geometric parameters (Å, º)

O1—N1	1.2255 (10)	C5—C6	1.3852 (11)
O2—N1	1.2252 (11)	C6—H6	0.944 (14)
O3—C7	1.2225 (9)	C8—C9	1.4127 (11)
O4—C7	1.3081 (10)	C8—H8	0.989 (14)
O4—H1O4	0.853 (9)	C9—C10	1.3705 (12)
O5—N2	1.2252 (10)	C9—H9	0.987 (14)
O6—N2	1.2305 (9)	C10—C11	1.4177 (11)
N1—C1	1.4723 (10)	C10—H10	0.960 (15)
N2—C5	1.4731 (10)	C11—C12	1.4166 (11)
N3—C8	1.3213 (10)	C11—C16	1.4198 (10)
N3—C16	1.3722 (10)	C12—C13	1.3743 (12)
C1—C2	1.3850 (11)	C12—H12	0.978 (14)
C1—C6	1.3874 (11)	C13—C14	1.4175 (12)
C2—C3	1.3951 (11)	C13—H13	0.977 (14)
C2—H2	0.963 (13)	C14—C15	1.3732 (12)
C3—C4	1.3947 (10)	C14—H14	0.947 (15)
C3—C7	1.5021 (11)	C15—C16	1.4172 (11)
C4—C5	1.3901 (11)	C15—H15	0.967 (13)
C4—H4	0.960 (14)
C7—O4—H1O4	109.5 (15)	O4—C7—C3	113.63 (7)
O2—N1—O1	124.19 (8)	N3—C8—C9	123.48 (8)
O2—N1—C1	117.59 (7)	N3—C8—H8	115.1 (8)
O1—N1—C1	118.22 (7)	C9—C8—H8	121.4 (8)
O5—N2—O6	124.57 (7)	C10—C9—C8	118.66 (7)
O5—N2—C5	117.80 (7)	C10—C9—H9	123.6 (8)
O6—N2—C5	117.63 (7)	C8—C9—H9	117.8 (8)
C8—N3—C16	118.97 (7)	C9—C10—C11	119.51 (7)
C2—C1—C6	123.04 (7)	C9—C10—H10	120.6 (9)
C2—C1—N1	118.72 (7)	C11—C10—H10	119.9 (9)
C6—C1—N1	118.21 (7)	C12—C11—C10	122.65 (7)
C1—C2—C3	118.83 (7)	C12—C11—C16	119.09 (7)
C1—C2—H2	120.1 (8)	C10—C11—C16	118.25 (7)
C3—C2—H2	121.0 (8)	C13—C12—C11	120.22 (7)
C4—C3—C2	120.14 (7)	C13—C12—H12	120.9 (8)
C4—C3—C7	121.61 (7)	C11—C12—H12	118.9 (8)
C2—C3—C7	118.23 (7)	C12—C13—C14	120.37 (8)
C5—C4—C3	118.39 (7)	C12—C13—H13	120.3 (8)
C5—C4—H4	120.6 (8)	C14—C13—H13	119.3 (8)
C3—C4—H4	121.0 (8)	C15—C14—C13	120.77 (7)
C6—C5—C4	123.30 (7)	C15—C14—H14	119.4 (9)
C6—C5—N2	117.83 (7)	C13—C14—H14	119.8 (9)
C4—C5—N2	118.84 (7)	C14—C15—C16	119.63 (7)
C5—C6—C1	116.25 (7)	C14—C15—H15	120.8 (8)
C5—C6—H6	122.8 (8)	C16—C15—H15	119.6 (8)
C1—C6—H6	120.9 (8)	N3—C16—C15	119.00 (7)
O3—C7—O4	125.21 (7)	N3—C16—C11	121.11 (7)
O3—C7—C3	121.16 (7)	C15—C16—C11	119.89 (7)
O2—N1—C1—C2	0.41 (12)	C2—C3—C7—O3	3.71 (11)
O1—N1—C1—C2	−179.54 (8)	C4—C3—C7—O4	2.58 (11)
O2—N1—C1—C6	−177.64 (8)	C2—C3—C7—O4	−175.80 (7)
O1—N1—C1—C6	2.41 (12)	C16—N3—C8—C9	−0.96 (12)
C6—C1—C2—C3	0.99 (12)	N3—C8—C9—C10	0.31 (12)
N1—C1—C2—C3	−176.95 (7)	C8—C9—C10—C11	0.47 (12)
C1—C2—C3—C4	1.03 (11)	C9—C10—C11—C12	178.24 (8)
C1—C2—C3—C7	179.44 (7)	C9—C10—C11—C16	−0.55 (11)
C2—C3—C4—C5	−2.16 (11)	C10—C11—C12—C13	179.77 (7)
C7—C3—C4—C5	179.49 (7)	C16—C11—C12—C13	−1.45 (12)
C3—C4—C5—C6	1.40 (12)	C11—C12—C13—C14	0.73 (12)
C3—C4—C5—N2	179.50 (7)	C12—C13—C14—C15	0.74 (13)
O5—N2—C5—C6	174.43 (7)	C13—C14—C15—C16	−1.42 (12)
O6—N2—C5—C6	−5.10 (10)	C8—N3—C16—C15	−178.85 (7)
O5—N2—C5—C4	−3.77 (11)	C8—N3—C16—C11	0.84 (11)
O6—N2—C5—C4	176.70 (7)	C14—C15—C16—N3	−179.63 (7)
C4—C5—C6—C1	0.50 (11)	C14—C15—C16—C11	0.67 (11)
N2—C5—C6—C1	−177.61 (6)	C12—C11—C16—N3	−178.94 (7)
C2—C1—C6—C5	−1.73 (11)	C10—C11—C16—N3	−0.10 (11)
N1—C1—C6—C5	176.23 (7)	C12—C11—C16—C15	0.76 (11)
C4—C3—C7—O3	−177.91 (7)	C10—C11—C16—C15	179.59 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···N3	0.85 (2)	1.75 (2)	2.6019 (9)	176 (2)
C8—H8···O3	0.989 (14)	2.465 (14)	3.2237 (10)	133 (1)
C10—H10···O3^i	0.958 (14)	2.454 (14)	3.2530 (10)	141 (1)
C13—H13···O2^ii	0.977 (14)	2.512 (14)	3.2129 (12)	129 (1)

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