1,10-Phenanthrolin-1-ium 2-carboxy-4-nitro­benzoate

Guo, M.-L.

doi:10.1107/S1600536805001765

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1,10-Phenanthrolin-1-ium 2-carboxy-4-nitrobenzoate

M.-L. Guo

The cation of the title salt, C₁₂H₉N ${}_{2}^{\,\,+}$ ·C₈H₄NO ${}_{6}^{\,\,- }$ , is a monoprotonated 1,10-phenanthroline molecule, whereas its anion is a monodeprotonated 4-nitrophthalic acid molecule. There is a strong, almost symmetrical, intramolecular hydrogen bond linking the O atoms of neighbouring carboxylate groups within the anion [O—H = 1.13 (4) Å, H

O = 1.27 (4) Å, O

O = 2.395 (3) Å and O—H

O = 173 (4)°]. An N—H

O bond [N—H = 1.00 (3) Å, H

O = 1.70 (3) Å, N

O = 2.668 (3) Å and N—H

O = 160 (3)°] is responsible for formation of ion pairs, which are further loosely aggregated into a three-dimensional framework via C—H

O and π–π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001765/ya6232sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001765/ya6232Isup2.hkl Contains datablock I

CCDC reference: 264074

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.056
wR factor = 0.146
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.115
            Value of mu given      =     0.110
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C13    -   C19    ...       1.53 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C14    -   C20    ...       1.53 Ang.

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

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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,10-Phenanthrolin-1-ium 2-carboxy-4-nitrobenzoate top

Crystal data top

C₁₂H₉N₂⁺·C₈H₄NO₆⁻	F(000) = 808
M_r = 391.33	D_x = 1.519 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 784 reflections
a = 6.328 (2) Å	θ = 2.9–25.4°
b = 7.696 (3) Å	µ = 0.11 mm⁻¹
c = 35.175 (12) Å	T = 293 K
β = 92.678 (6)°	Needle, yellow
V = 1711.0 (11) Å³	0.26 × 0.12 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3486 independent reflections
Radiation source: fine-focus sealed tube	2198 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 26.4°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
T_min = 0.959, T_max = 0.989	k = −9→8
9498 measured reflections	l = −42→43

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0557P)² + 0.6995P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.002
3486 reflections	Δρ_max = 0.17 e Å⁻³
271 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0069 (12)

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	0.9692 (3)	0.7252 (3)	0.67233 (6)	0.0624 (6)
O2	0.7437 (4)	0.8819 (3)	0.70247 (5)	0.0645 (6)
O3	0.4187 (3)	1.0346 (3)	0.68927 (6)	0.0636 (6)
O4	0.1939 (3)	1.0839 (3)	0.64140 (6)	0.0688 (7)
O5	0.8092 (4)	0.8279 (5)	0.50201 (7)	0.1144 (12)
O6	1.0503 (4)	0.7306 (4)	0.54086 (7)	0.0870 (8)
N1	0.9149 (3)	0.2866 (3)	0.67473 (6)	0.0403 (5)
N2	0.8519 (3)	0.3116 (3)	0.59753 (6)	0.0478 (6)
N3	0.8793 (4)	0.7990 (4)	0.53417 (7)	0.0648 (7)
C1	0.9590 (4)	0.2785 (4)	0.71194 (8)	0.0513 (7)
H1	1.0830	0.2246	0.7210	0.062*
C2	0.8235 (5)	0.3492 (4)	0.73748 (8)	0.0574 (8)
H2	0.8553	0.3440	0.7635	0.069*
C3	0.6413 (5)	0.4269 (4)	0.72356 (8)	0.0556 (8)
H3	0.5486	0.4749	0.7404	0.067*
C4	0.5923 (4)	0.4354 (3)	0.68474 (7)	0.0415 (6)
C5	0.4015 (4)	0.5100 (4)	0.66857 (9)	0.0509 (7)
H5	0.3049	0.5596	0.6845	0.061*
C6	0.3593 (4)	0.5097 (4)	0.63071 (9)	0.0534 (8)
H6	0.2315	0.5548	0.6210	0.064*
C7	0.5063 (4)	0.4419 (3)	0.60526 (8)	0.0448 (7)
C8	0.4724 (5)	0.4416 (4)	0.56567 (9)	0.0610 (8)
H8	0.3459	0.4835	0.5547	0.073*
C9	0.6245 (6)	0.3801 (4)	0.54332 (8)	0.0664 (9)
H9	0.6036	0.3798	0.5170	0.080*
C10	0.8120 (5)	0.3175 (4)	0.56034 (8)	0.0600 (8)
H10	0.9156	0.2775	0.5446	0.072*
C11	0.6985 (4)	0.3730 (3)	0.61955 (7)	0.0379 (6)
C12	0.7374 (4)	0.3650 (3)	0.66002 (7)	0.0352 (6)
C13	0.7109 (4)	0.8707 (3)	0.63332 (7)	0.0358 (6)
C14	0.5124 (4)	0.9515 (3)	0.62581 (7)	0.0363 (6)
C15	0.4403 (4)	0.9711 (4)	0.58807 (7)	0.0466 (7)
H15	0.3081	1.0209	0.5831	0.056*
C16	0.5548 (4)	0.9205 (4)	0.55810 (7)	0.0511 (7)
H16	0.5017	0.9335	0.5332	0.061*
C17	0.7508 (4)	0.8498 (4)	0.56597 (7)	0.0460 (7)
C18	0.8279 (4)	0.8228 (3)	0.60234 (7)	0.0419 (6)
H18	0.9601	0.7718	0.6065	0.050*
C19	0.8178 (4)	0.8210 (4)	0.67157 (7)	0.0436 (6)
C20	0.3635 (4)	1.0274 (3)	0.65441 (8)	0.0440 (7)
H1A	1.009 (5)	0.225 (4)	0.6571 (9)	0.071 (9)*
H2A	0.596 (7)	0.962 (5)	0.6970 (11)	0.107 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0528 (12)	0.0721 (14)	0.0613 (13)	0.0184 (11)	−0.0071 (10)	0.0093 (11)
O2	0.0679 (14)	0.0885 (16)	0.0366 (11)	0.0158 (12)	−0.0018 (10)	−0.0033 (11)
O3	0.0626 (14)	0.0841 (16)	0.0451 (12)	0.0159 (12)	0.0127 (10)	−0.0078 (11)
O4	0.0519 (13)	0.0837 (16)	0.0715 (14)	0.0280 (12)	0.0097 (11)	−0.0039 (12)
O5	0.094 (2)	0.208 (4)	0.0423 (13)	0.039 (2)	0.0084 (13)	−0.0166 (17)
O6	0.0648 (16)	0.126 (2)	0.0714 (15)	0.0301 (15)	0.0157 (13)	−0.0147 (15)
N1	0.0355 (12)	0.0474 (13)	0.0381 (12)	0.0032 (10)	0.0021 (10)	−0.0005 (10)
N2	0.0500 (14)	0.0564 (15)	0.0374 (12)	0.0089 (11)	0.0073 (10)	−0.0010 (11)
N3	0.0564 (16)	0.092 (2)	0.0467 (15)	0.0072 (15)	0.0093 (13)	−0.0131 (14)
C1	0.0462 (16)	0.0629 (19)	0.0438 (16)	0.0001 (14)	−0.0070 (13)	0.0038 (14)
C2	0.064 (2)	0.075 (2)	0.0343 (15)	−0.0102 (17)	0.0032 (14)	−0.0019 (14)
C3	0.0558 (18)	0.063 (2)	0.0489 (17)	−0.0049 (16)	0.0161 (14)	−0.0123 (15)
C4	0.0386 (14)	0.0403 (15)	0.0464 (15)	−0.0047 (12)	0.0112 (12)	−0.0060 (12)
C5	0.0360 (15)	0.0483 (17)	0.070 (2)	0.0050 (13)	0.0162 (14)	−0.0058 (15)
C6	0.0367 (15)	0.0516 (18)	0.071 (2)	0.0075 (13)	−0.0033 (14)	0.0037 (15)
C7	0.0426 (15)	0.0397 (15)	0.0515 (16)	0.0027 (12)	−0.0037 (13)	0.0040 (13)
C8	0.066 (2)	0.059 (2)	0.0560 (19)	0.0045 (16)	−0.0165 (16)	0.0102 (16)
C9	0.089 (3)	0.071 (2)	0.0376 (16)	0.0051 (19)	−0.0070 (17)	0.0053 (16)
C10	0.075 (2)	0.066 (2)	0.0399 (16)	0.0078 (17)	0.0118 (15)	0.0022 (15)
C11	0.0397 (14)	0.0358 (14)	0.0384 (14)	0.0004 (11)	0.0043 (11)	0.0020 (11)
C12	0.0312 (13)	0.0364 (14)	0.0382 (13)	0.0002 (11)	0.0038 (10)	−0.0005 (11)
C13	0.0360 (13)	0.0335 (13)	0.0377 (14)	−0.0016 (11)	0.0012 (11)	−0.0001 (11)
C14	0.0361 (14)	0.0325 (13)	0.0406 (14)	−0.0011 (11)	0.0031 (11)	0.0002 (11)
C15	0.0389 (15)	0.0548 (17)	0.0458 (16)	0.0090 (13)	−0.0008 (12)	0.0027 (13)
C16	0.0534 (17)	0.0664 (19)	0.0333 (14)	0.0063 (15)	−0.0003 (12)	−0.0001 (14)
C17	0.0452 (16)	0.0512 (17)	0.0421 (15)	0.0012 (13)	0.0079 (12)	−0.0077 (13)
C18	0.0337 (13)	0.0454 (16)	0.0467 (15)	0.0066 (12)	0.0015 (11)	−0.0043 (13)
C19	0.0415 (15)	0.0468 (16)	0.0420 (15)	−0.0024 (13)	−0.0014 (12)	0.0015 (13)
C20	0.0431 (16)	0.0404 (16)	0.0494 (17)	0.0031 (13)	0.0125 (13)	−0.0010 (13)

Geometric parameters (Å, º) top

O1—C19	1.208 (3)	C5—H5	0.9300
O2—C19	1.292 (3)	C6—C7	1.420 (4)
O2—H2A	1.13 (4)	C6—H6	0.9300
O3—C20	1.260 (3)	C7—C11	1.398 (3)
O3—H2A	1.27 (4)	C7—C8	1.399 (4)
O4—C20	1.226 (3)	C8—C9	1.356 (4)
O5—N3	1.216 (3)	C8—H8	0.9300
O6—N3	1.216 (3)	C9—C10	1.390 (4)
N1—C1	1.327 (3)	C9—H9	0.9300
N1—C12	1.356 (3)	C10—H10	0.9300
N1—H1A	1.00 (3)	C11—C12	1.435 (3)
N2—C10	1.322 (3)	C13—C18	1.395 (3)
N2—C11	1.355 (3)	C13—C14	1.416 (3)
N3—C17	1.466 (3)	C13—C19	1.526 (3)
C1—C2	1.382 (4)	C14—C15	1.391 (3)
C1—H1	0.9300	C14—C20	1.526 (4)
C2—C3	1.369 (4)	C15—C16	1.364 (4)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.388 (4)	C16—C17	1.370 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C12	1.403 (3)	C17—C18	1.364 (4)
C4—C5	1.431 (4)	C18—H18	0.9300
C5—C6	1.346 (4)

C19—O2—H2A	112.6 (19)	C10—C9—H9	120.5
C20—O3—H2A	112.9 (17)	N2—C10—C9	123.9 (3)
C1—N1—C12	122.0 (2)	N2—C10—H10	118.0
C1—N1—H1A	119.0 (17)	C9—C10—H10	118.0
C12—N1—H1A	118.8 (17)	N2—C11—C7	124.1 (2)
C10—N2—C11	116.4 (2)	N2—C11—C12	117.2 (2)
O5—N3—O6	122.8 (3)	C7—C11—C12	118.6 (2)
O5—N3—C17	118.0 (3)	N1—C12—C4	119.3 (2)
O6—N3—C17	119.2 (3)	N1—C12—C11	119.9 (2)
N1—C1—C2	121.0 (3)	C4—C12—C11	120.8 (2)
N1—C1—H1	119.5	C18—C13—C14	117.9 (2)
C2—C1—H1	119.5	C18—C13—C19	113.2 (2)
C3—C2—C1	118.5 (3)	C14—C13—C19	128.9 (2)
C3—C2—H2	120.7	C15—C14—C13	118.3 (2)
C1—C2—H2	120.7	C15—C14—C20	113.7 (2)
C2—C3—C4	121.2 (3)	C13—C14—C20	127.9 (2)
C2—C3—H3	119.4	C16—C15—C14	123.0 (3)
C4—C3—H3	119.4	C16—C15—H15	118.5
C3—C4—C12	118.0 (2)	C14—C15—H15	118.5
C3—C4—C5	123.7 (3)	C15—C16—C17	117.7 (2)
C12—C4—C5	118.3 (2)	C15—C16—H16	121.1
C6—C5—C4	121.1 (3)	C17—C16—H16	121.1
C6—C5—H5	119.4	C18—C17—C16	122.1 (2)
C4—C5—H5	119.4	C18—C17—N3	119.2 (2)
C5—C6—C7	121.3 (3)	C16—C17—N3	118.7 (2)
C5—C6—H6	119.4	C17—C18—C13	120.9 (2)
C7—C6—H6	119.4	C17—C18—H18	119.6
C11—C7—C8	116.6 (3)	C13—C18—H18	119.6
C11—C7—C6	119.8 (2)	O1—C19—O2	121.4 (3)
C8—C7—C6	123.6 (3)	O1—C19—C13	119.4 (2)
C9—C8—C7	119.8 (3)	O2—C19—C13	119.2 (2)
C9—C8—H8	120.1	O4—C20—O3	123.0 (3)
C7—C8—H8	120.1	O4—C20—C14	116.5 (2)
C8—C9—C10	119.1 (3)	O3—C20—C14	120.4 (2)
C8—C9—H9	120.5

C12—N1—C1—C2	0.6 (4)	C7—C11—C12—N1	174.9 (2)
N1—C1—C2—C3	0.4 (5)	N2—C11—C12—C4	176.1 (2)
C1—C2—C3—C4	0.0 (5)	C7—C11—C12—C4	−4.2 (4)
C2—C3—C4—C12	−1.3 (4)	C18—C13—C14—C15	3.1 (4)
C2—C3—C4—C5	178.0 (3)	C19—C13—C14—C15	−174.8 (2)
C3—C4—C5—C6	−177.9 (3)	C18—C13—C14—C20	−175.1 (2)
C12—C4—C5—C6	1.4 (4)	C19—C13—C14—C20	7.1 (4)
C4—C5—C6—C7	−2.6 (4)	C13—C14—C15—C16	−1.9 (4)
C5—C6—C7—C11	0.4 (4)	C20—C14—C15—C16	176.5 (3)
C5—C6—C7—C8	−178.6 (3)	C14—C15—C16—C17	−1.0 (4)
C11—C7—C8—C9	−1.5 (4)	C15—C16—C17—C18	2.8 (4)
C6—C7—C8—C9	177.6 (3)	C15—C16—C17—N3	−178.3 (3)
C7—C8—C9—C10	0.2 (5)	O5—N3—C17—C18	−178.4 (3)
C11—N2—C10—C9	−0.8 (5)	O6—N3—C17—C18	1.5 (4)
C8—C9—C10—N2	1.0 (5)	O5—N3—C17—C16	2.7 (5)
C10—N2—C11—C7	−0.6 (4)	O6—N3—C17—C16	−177.5 (3)
C10—N2—C11—C12	179.0 (2)	C16—C17—C18—C13	−1.6 (4)
C8—C7—C11—N2	1.7 (4)	N3—C17—C18—C13	179.5 (2)
C6—C7—C11—N2	−177.3 (3)	C14—C13—C18—C17	−1.4 (4)
C8—C7—C11—C12	−177.9 (2)	C19—C13—C18—C17	176.8 (2)
C6—C7—C11—C12	3.0 (4)	C18—C13—C19—O1	−11.2 (4)
C1—N1—C12—C4	−2.0 (4)	C14—C13—C19—O1	166.7 (3)
C1—N1—C12—C11	178.9 (2)	C18—C13—C19—O2	169.0 (2)
C3—C4—C12—N1	2.3 (4)	C14—C13—C19—O2	−13.1 (4)
C5—C4—C12—N1	−177.0 (2)	C15—C14—C20—O4	5.2 (4)
C3—C4—C12—C11	−178.6 (2)	C13—C14—C20—O4	−176.6 (3)
C5—C4—C12—C11	2.1 (4)	C15—C14—C20—O3	−172.8 (3)
N2—C11—C12—N1	−4.8 (4)	C13—C14—C20—O3	5.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O5ⁱ	0.93	2.58	3.507 (4)	177
C5—H5···O1ⁱⁱ	0.93	2.50	3.206 (3)	133
C3—H3···O3ⁱⁱⁱ	0.93	2.51	3.216 (4)	132
O2—H2A···O3	1.13 (4)	1.27 (4)	2.395 (3)	173 (4)
N1—H1A···O4^iv	1.00 (3)	1.70 (3)	2.668 (3)	160 (3)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+3/2; (iv) x+1, y−1, z.

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