A cation-anion complex: 1,10-phenanthrolin-1-ium 5-sulfonatosalicylic acid

The title compound, C₁₂H₉N₂⁺·C₇H₅O₆S^-, consists of a 1,10-phenanthrolin-1-ium cation and a 5-sulfosalicyl­ate anion. Hydro­gen bonds link the anions into a one-dimensional chain. Furthermore, hydrogen bonds between the NH groups of 1,10-phenanthrolin-1-ium cations and the sulfonate O atoms attach the cations to the one-dimensional chain.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.043
• wR factor = 0.106
• Data-to-parameter ratio = 11.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   O4      ..       5.55 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   O6      ..       5.22 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C12 H9 N2

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.15
           From the CIF: _reflns_number_total               2938
           Count of symmetry unique reflns         1626
           Completeness (_total/calc)            180.69%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1312
           Fraction of Friedel pairs measured     0.807
           Are heavy atom types Z>Si present          yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT and? SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1,10-phenanthrolin-1-ium 5-sulfosalicylate

Crystal data

C12H9N2^+·C7H5O6S^−	F(000) = 412
Mr = 398.38	Dx = 1.539 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5405 reflections
a = 7.0492 (9) Å	θ = 0.9–28.3°
b = 10.6716 (14) Å	µ = 0.23 mm^−1
c = 11.7464 (15) Å	T = 295 K
β = 103.426 (2)°	Block, colorless
V = 859.49 (19) Å^3	0.34 × 0.31 × 0.15 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	2938 independent reflections
Radiation source: fine-focus sealed tube	2910 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
φ and ω scans	θmax = 25.2°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→8
Tmin = 0.926, Tmax = 0.964	k = −12→12
4555 measured reflections	l = −14→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0565P)^2 + 0.1823P] where P = (Fo^2 + 2Fc^2)/3
S = 1.18	(Δ/σ)max < 0.001
2938 reflections	Δρmax = 0.26 e Å^−3
262 parameters	Δρmin = −0.33 e Å^−3
4 restraints	Absolute structure: Flack (1983), 1312 Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (9)

Special details

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
S1	0.69901 (10)	0.84471 (7)	0.22996 (5)	0.03425 (18)
O1	0.9358 (4)	0.5001 (2)	0.54499 (18)	0.0535 (6)
O2	0.9153 (4)	0.3121 (2)	0.4606 (2)	0.0592 (7)
O3	0.8106 (4)	0.2968 (2)	0.2349 (2)	0.0567 (7)
O4	0.5887 (3)	0.8750 (2)	0.11248 (18)	0.0466 (6)
O5	0.8936 (3)	0.9012 (2)	0.25274 (19)	0.0473 (6)
O6	0.5978 (4)	0.8708 (2)	0.32056 (19)	0.0552 (6)
C1	0.8951 (4)	0.4252 (3)	0.4547 (3)	0.0388 (7)
C2	0.8235 (4)	0.4901 (3)	0.3418 (2)	0.0342 (6)
C3	0.7858 (5)	0.4216 (3)	0.2368 (3)	0.0389 (7)
C4	0.7206 (4)	0.4844 (3)	0.1305 (3)	0.0415 (7)
H4	0.6937	0.4394	0.0609	0.050*
C5	0.6958 (4)	0.6124 (3)	0.1280 (2)	0.0353 (6)
H5	0.6537	0.6535	0.0568	0.042*
C6	0.7336 (4)	0.6798 (3)	0.2315 (2)	0.0305 (6)
C7	0.7984 (4)	0.6201 (3)	0.3376 (2)	0.0328 (6)
H7	0.8254	0.6665	0.4065	0.039*
N1	0.7714 (4)	0.9974 (3)	−0.0418 (2)	0.0411 (6)
N2	0.6916 (4)	0.7683 (3)	−0.1463 (2)	0.0487 (7)
C8	0.8217 (5)	1.1032 (3)	0.0171 (3)	0.0525 (9)
H8	0.8386	1.1050	0.0980	0.063*
C9	0.8484 (5)	1.2098 (3)	−0.0425 (4)	0.0550 (9)
H9	0.8898	1.2833	−0.0017	0.066*
C10	0.8145 (5)	1.2079 (3)	−0.1612 (3)	0.0511 (9)
H10	0.8267	1.2813	−0.2017	0.061*
C11	0.7615 (4)	1.0965 (3)	−0.2228 (3)	0.0416 (7)
C12	0.7238 (5)	1.0863 (4)	−0.3486 (3)	0.0524 (10)
H12	0.7328	1.1573	−0.3930	0.063*
C13	0.6761 (5)	0.9762 (4)	−0.4023 (3)	0.0538 (10)
H13	0.6511	0.9723	−0.4835	0.065*
C14	0.6626 (4)	0.8643 (4)	−0.3373 (3)	0.0462 (8)
C15	0.6202 (6)	0.7476 (5)	−0.3887 (3)	0.0615 (11)
H15	0.5965	0.7395	−0.4696	0.074*
C16	0.6133 (6)	0.6455 (5)	−0.3216 (4)	0.0704 (12)
H16	0.5851	0.5669	−0.3554	0.084*
C17	0.6494 (6)	0.6608 (4)	−0.1999 (4)	0.0636 (10)
H17	0.6431	0.5903	−0.1545	0.076*
C18	0.7442 (4)	0.9884 (3)	−0.1589 (2)	0.0356 (6)
C19	0.6969 (4)	0.8694 (3)	−0.2147 (3)	0.0400 (7)
H1	0.997 (6)	0.461 (4)	0.605 (3)	0.080*
H2	0.751 (7)	0.935 (3)	−0.006 (4)	0.080*
H3	0.861 (6)	0.269 (5)	0.303 (2)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0470 (4)	0.0323 (3)	0.0220 (3)	0.0063 (3)	0.0052 (2)	0.0012 (3)
O1	0.0820 (17)	0.0438 (13)	0.0286 (11)	0.0175 (12)	0.0006 (11)	0.0067 (10)
O2	0.0834 (18)	0.0345 (13)	0.0509 (14)	0.0020 (12)	−0.0022 (13)	0.0081 (10)
O3	0.0787 (19)	0.0362 (13)	0.0490 (15)	0.0031 (12)	0.0019 (13)	−0.0064 (11)
O4	0.0604 (13)	0.0406 (13)	0.0340 (11)	0.0052 (10)	0.0013 (9)	0.0045 (9)
O5	0.0604 (14)	0.0413 (12)	0.0369 (12)	−0.0035 (10)	0.0046 (10)	−0.0028 (10)
O6	0.0821 (16)	0.0447 (15)	0.0433 (12)	0.0176 (12)	0.0242 (11)	0.0021 (10)
C1	0.0410 (17)	0.0347 (16)	0.0394 (17)	0.0007 (13)	0.0068 (13)	0.0029 (14)
C2	0.0322 (14)	0.0396 (15)	0.0300 (14)	−0.0018 (12)	0.0057 (11)	−0.0012 (13)
C3	0.0374 (16)	0.0321 (16)	0.0465 (18)	−0.0020 (13)	0.0079 (14)	−0.0046 (14)
C4	0.0454 (17)	0.0483 (18)	0.0271 (14)	−0.0001 (14)	0.0012 (12)	−0.0080 (14)
C5	0.0406 (16)	0.0400 (17)	0.0239 (14)	0.0009 (13)	0.0046 (12)	−0.0016 (12)
C6	0.0310 (13)	0.0297 (14)	0.0304 (14)	−0.0003 (11)	0.0060 (11)	−0.0025 (11)
C7	0.0356 (15)	0.0341 (15)	0.0274 (14)	−0.0017 (12)	0.0047 (11)	−0.0004 (12)
N1	0.0552 (16)	0.0357 (14)	0.0323 (13)	−0.0031 (12)	0.0097 (11)	−0.0030 (12)
N2	0.0666 (19)	0.0406 (15)	0.0392 (15)	−0.0052 (14)	0.0125 (13)	−0.0049 (12)
C8	0.058 (2)	0.055 (2)	0.0453 (18)	−0.0014 (17)	0.0122 (16)	−0.0108 (17)
C9	0.062 (2)	0.0372 (18)	0.068 (2)	−0.0033 (16)	0.0198 (18)	−0.0079 (17)
C10	0.0453 (18)	0.0377 (18)	0.074 (3)	0.0027 (15)	0.0217 (17)	0.0114 (17)
C11	0.0314 (15)	0.0470 (19)	0.0482 (18)	0.0054 (14)	0.0129 (13)	0.0106 (15)
C12	0.0410 (18)	0.072 (3)	0.0473 (19)	0.0103 (17)	0.0165 (15)	0.0253 (19)
C13	0.0441 (19)	0.086 (3)	0.0321 (17)	0.0050 (18)	0.0108 (14)	0.0026 (19)
C14	0.0324 (14)	0.071 (2)	0.0356 (15)	−0.0010 (16)	0.0093 (11)	−0.0043 (16)
C15	0.059 (2)	0.088 (3)	0.040 (2)	−0.020 (2)	0.0163 (17)	−0.026 (2)
C16	0.076 (3)	0.071 (3)	0.068 (3)	−0.024 (2)	0.024 (2)	−0.034 (2)
C17	0.085 (3)	0.050 (2)	0.060 (2)	−0.017 (2)	0.025 (2)	−0.0078 (19)
C18	0.0308 (14)	0.0409 (16)	0.0360 (15)	0.0010 (13)	0.0095 (12)	−0.0001 (14)
C19	0.0372 (15)	0.049 (2)	0.0336 (15)	−0.0014 (13)	0.0072 (11)	−0.0036 (14)

Geometric parameters (Å, º)

S1—O6	1.439 (2)	N2—C17	1.309 (5)
S1—O4	1.454 (2)	N2—C19	1.351 (4)
S1—O5	1.465 (2)	C8—C9	1.371 (5)
S1—C6	1.777 (3)	C8—H8	0.9300
O1—C1	1.306 (4)	C9—C10	1.360 (5)
O1—H1	0.85 (4)	C9—H9	0.9300
O2—C1	1.216 (4)	C10—C11	1.397 (5)
O3—C3	1.344 (4)	C10—H10	0.9300
O3—H3	0.85 (3)	C11—C18	1.397 (5)
C1—C2	1.477 (4)	C11—C12	1.443 (5)
C2—C7	1.398 (4)	C12—C13	1.339 (6)
C2—C3	1.406 (4)	C12—H12	0.9300
C3—C4	1.397 (5)	C13—C14	1.432 (6)
C4—C5	1.376 (5)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.385 (6)
C5—C6	1.384 (4)	C14—C19	1.405 (4)
C5—H5	0.9300	C15—C16	1.353 (7)
C6—C7	1.379 (4)	C15—H15	0.9300
C7—H7	0.9300	C16—C17	1.402 (6)
N1—C8	1.328 (4)	C16—H16	0.9300
N1—C18	1.348 (4)	C17—H17	0.9300
N1—H2	0.82 (4)	C18—C19	1.433 (5)
O6—S1—O4	114.28 (14)	C9—C8—H8	120.3
O6—S1—O5	112.90 (14)	C10—C9—C8	119.9 (3)
O4—S1—O5	110.69 (14)	C10—C9—H9	120.0
O6—S1—C6	105.93 (13)	C8—C9—H9	120.0
O4—S1—C6	105.79 (13)	C9—C10—C11	120.4 (3)
O5—S1—C6	106.57 (13)	C9—C10—H10	119.8
C1—O1—H1	110 (3)	C11—C10—H10	119.8
C3—O3—H3	111 (4)	C10—C11—C18	118.1 (3)
O2—C1—O1	124.1 (3)	C10—C11—C12	123.9 (3)
O2—C1—C2	121.9 (3)	C18—C11—C12	118.0 (3)
O1—C1—C2	114.0 (3)	C13—C12—C11	121.0 (3)
C7—C2—C3	119.3 (3)	C13—C12—H12	119.5
C7—C2—C1	120.8 (3)	C11—C12—H12	119.5
C3—C2—C1	119.9 (3)	C12—C13—C14	121.4 (3)
O3—C3—C4	118.6 (3)	C12—C13—H13	119.3
O3—C3—C2	122.1 (3)	C14—C13—H13	119.3
C4—C3—C2	119.3 (3)	C15—C14—C19	116.7 (4)
C5—C4—C3	120.6 (3)	C15—C14—C13	123.5 (3)
C5—C4—H4	119.7	C19—C14—C13	119.8 (4)
C3—C4—H4	119.7	C16—C15—C14	120.2 (3)
C4—C5—C6	119.9 (3)	C16—C15—H15	119.9
C4—C5—H5	120.0	C14—C15—H15	119.9
C6—C5—H5	120.0	C15—C16—C17	118.5 (4)
C7—C6—C5	120.7 (3)	C15—C16—H16	120.7
C7—C6—S1	118.8 (2)	C17—C16—H16	120.7
C5—C6—S1	120.5 (2)	N2—C17—C16	124.1 (4)
C6—C7—C2	120.2 (3)	N2—C17—H17	118.0
C6—C7—H7	119.9	C16—C17—H17	118.0
C2—C7—H7	119.9	N1—C18—C11	118.7 (3)
C8—N1—C18	123.3 (3)	N1—C18—C19	119.5 (3)
C8—N1—H2	119 (3)	C11—C18—C19	121.8 (3)
C18—N1—H2	118 (3)	N2—C19—C14	123.8 (3)
C17—N2—C19	116.6 (3)	N2—C19—C18	118.2 (3)
N1—C8—C9	119.4 (3)	C14—C19—C18	118.0 (3)
N1—C8—H8	120.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5^i	0.85 (4)	1.79 (4)	2.623 (3)	168 (5)
O3—H3···O2	0.85 (3)	1.86 (3)	2.587 (4)	142 (5)
N1—H2···O4	0.82 (4)	2.10 (3)	2.780 (4)	141 (4)

Symmetry code: (i) −x+2, y−1/2, −z+1.