1,10-Phenanthrolinium perchlorate

The proton-transfer title compound, C₁₂H₉N₂⁺·ClO₄⁻, has been obtained from 1,10-phenanthroline and HClO₄. In the crystal structure, the mol­ecules stack along the a axis via hydrogen-bond inter­actions and van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 288 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.127
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        Cl1

Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C12 H9 N2

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 133
              The proton-transfer title compound, C~12~H9~N~2~^+^.ClO~4~^-^, has been
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1,10-Phenanthrolinium perchlorate

Crystal data

C12H9N2^+·ClO4^−	Z = 2
Mr = 280.66	F(000) = 288
Triclinic, P1	Dx = 1.598 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8054 (12) Å	Cell parameters from 3837 reflections
b = 9.778 (2) Å	θ = 2.0–28.3°
c = 10.628 (2) Å	µ = 0.34 mm^−1
α = 93.16 (3)°	T = 288 K
β = 101.41 (3)°	Block, pink
γ = 98.08 (3)°	0.30 × 0.25 × 0.20 mm
V = 583.4 (2) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2767 independent reflections
Radiation source: fine-focus sealed tube	2345 reflections with I > 2σI
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.900, Tmax = 0.938	k = −12→12
5890 measured reflections	l = −13→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0799P)^2 + 0.1598P] where P = (Fo^2 + 2Fc^2)/3
2767 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.43 e Å^−3

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 > 2σ(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
Cl1	0.31908 (7)	0.82627 (4)	0.26251 (4)	0.04399 (16)
N2	−0.3268 (3)	0.41582 (15)	0.36117 (14)	0.0434 (3)
N1	−0.6980 (3)	0.26945 (15)	0.44488 (14)	0.0415 (3)
C12	−0.5063 (3)	0.33998 (16)	0.27218 (16)	0.0377 (3)
C11	−0.7008 (3)	0.26530 (15)	0.31678 (15)	0.0374 (3)
C10	−0.5126 (3)	0.32988 (17)	0.13890 (17)	0.0419 (4)
C9	−0.8950 (3)	0.18057 (19)	0.09582 (18)	0.0485 (4)
H9A	−1.0227	0.1293	0.0375	0.058*
C8	−0.8953 (3)	0.18658 (17)	0.23081 (17)	0.0409 (4)
C7	−1.0822 (3)	0.11925 (18)	0.2824 (2)	0.0480 (4)
H7A	−1.2133	0.0665	0.2276	0.058*
C6	−0.3192 (4)	0.4030 (2)	0.09733 (19)	0.0505 (4)
H6A	−0.3148	0.3996	0.0102	0.061*
C5	−0.1489 (3)	0.48243 (18)	0.3166 (2)	0.0485 (4)
H5A	−0.0234	0.5346	0.3757	0.058*
C4	−0.7121 (3)	0.2482 (2)	0.05258 (17)	0.0490 (4)
H4A	−0.7149	0.2420	−0.0354	0.059*
C3	−0.1374 (4)	0.47946 (19)	0.1863 (2)	0.0531 (5)
H3A	−0.0081	0.5287	0.1605	0.064*
C2	−0.8734 (3)	0.20594 (19)	0.49363 (18)	0.0472 (4)
H2B	−0.8628	0.2119	0.5823	0.057*
C1	−1.0727 (3)	0.13066 (19)	0.4123 (2)	0.0494 (4)
H1B	−1.1986	0.0884	0.4457	0.059*
O4	0.0667 (2)	0.81643 (17)	0.23368 (15)	0.0649 (4)
O3	0.4198 (3)	0.92981 (17)	0.36559 (15)	0.0687 (4)
O2	0.3823 (4)	0.69603 (18)	0.2983 (2)	0.0963 (7)
O1	0.4066 (4)	0.8645 (3)	0.15122 (18)	0.0974 (7)
H1A	−0.574 (2)	0.3160 (19)	0.4901 (18)	0.053 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0380 (2)	0.0517 (3)	0.0365 (2)	−0.00053 (16)	0.00126 (15)	−0.00410 (17)
N2	0.0414 (7)	0.0389 (7)	0.0448 (8)	0.0002 (5)	0.0019 (6)	−0.0008 (6)
N1	0.0390 (7)	0.0426 (7)	0.0390 (7)	0.0015 (6)	0.0018 (6)	0.0042 (6)
C12	0.0377 (8)	0.0335 (7)	0.0398 (8)	0.0056 (6)	0.0029 (6)	0.0028 (6)
C11	0.0365 (8)	0.0337 (7)	0.0389 (8)	0.0057 (6)	0.0005 (6)	0.0021 (6)
C10	0.0446 (9)	0.0395 (8)	0.0412 (8)	0.0101 (7)	0.0057 (7)	0.0034 (7)
C9	0.0448 (9)	0.0483 (9)	0.0443 (9)	0.0058 (7)	−0.0056 (7)	−0.0079 (7)
C8	0.0377 (8)	0.0355 (7)	0.0450 (9)	0.0056 (6)	−0.0008 (6)	−0.0001 (7)
C7	0.0369 (8)	0.0383 (8)	0.0624 (11)	0.0014 (6)	−0.0007 (7)	0.0009 (8)
C6	0.0586 (11)	0.0499 (10)	0.0479 (10)	0.0132 (8)	0.0174 (8)	0.0101 (8)
C5	0.0443 (9)	0.0379 (8)	0.0592 (11)	−0.0007 (7)	0.0070 (8)	0.0000 (8)
C4	0.0537 (10)	0.0547 (10)	0.0360 (8)	0.0132 (8)	0.0017 (7)	−0.0025 (7)
C3	0.0512 (10)	0.0434 (9)	0.0667 (12)	0.0008 (7)	0.0200 (9)	0.0090 (9)
C2	0.0472 (9)	0.0490 (9)	0.0469 (9)	0.0088 (7)	0.0111 (7)	0.0106 (8)
C1	0.0404 (9)	0.0425 (9)	0.0658 (12)	0.0041 (7)	0.0121 (8)	0.0108 (8)
O4	0.0402 (7)	0.0789 (10)	0.0670 (9)	0.0000 (6)	−0.0003 (6)	−0.0033 (8)
O3	0.0638 (9)	0.0687 (9)	0.0587 (9)	−0.0067 (7)	−0.0045 (7)	−0.0203 (8)
O2	0.0850 (12)	0.0578 (10)	0.1188 (17)	0.0091 (9)	−0.0398 (11)	−0.0032 (10)
O1	0.0787 (12)	0.157 (2)	0.0564 (10)	−0.0027 (12)	0.0292 (9)	0.0020 (12)

Geometric parameters (Å, º)

Cl1—O3	1.4230 (15)	C9—C8	1.433 (3)
Cl1—O4	1.4244 (14)	C9—H9A	0.9300
Cl1—O2	1.4251 (18)	C8—C7	1.409 (3)
Cl1—O1	1.4249 (19)	C7—C1	1.369 (3)
N2—C5	1.325 (2)	C7—H7A	0.9300
N2—C12	1.359 (2)	C6—C3	1.369 (3)
N1—C2	1.326 (2)	C6—H6A	0.9300
N1—C11	1.357 (2)	C5—C3	1.398 (3)
N1—H1A	0.839 (16)	C5—H5A	0.9300
C12—C10	1.407 (2)	C4—H4A	0.9300
C12—C11	1.432 (2)	C3—H3A	0.9300
C11—C8	1.404 (2)	C2—C1	1.387 (3)
C10—C6	1.404 (3)	C2—H2B	0.9300
C10—C4	1.435 (2)	C1—H1B	0.9300
C9—C4	1.343 (3)
O3—Cl1—O4	110.13 (10)	C11—C8—C9	118.52 (16)
O3—Cl1—O2	109.38 (11)	C7—C8—C9	123.58 (16)
O4—Cl1—O2	109.44 (12)	C1—C7—C8	120.63 (16)
O3—Cl1—O1	108.78 (12)	C1—C7—H7A	119.7
O4—Cl1—O1	108.57 (11)	C8—C7—H7A	119.7
O2—Cl1—O1	110.53 (15)	C3—C6—C10	119.32 (17)
C5—N2—C12	116.31 (16)	C3—C6—H6A	120.3
C2—N1—C11	123.35 (16)	C10—C6—H6A	120.3
C2—N1—H1A	123.4 (15)	N2—C5—C3	124.26 (17)
C11—N1—H1A	113.3 (15)	N2—C5—H5A	117.9
N2—C12—C10	124.07 (16)	C3—C5—H5A	117.9
N2—C12—C11	117.99 (15)	C9—C4—C10	121.55 (17)
C10—C12—C11	117.95 (15)	C9—C4—H4A	119.2
N1—C11—C8	118.83 (15)	C10—C4—H4A	119.2
N1—C11—C12	119.66 (14)	C6—C3—C5	119.01 (17)
C8—C11—C12	121.51 (15)	C6—C3—H3A	120.5
C12—C10—C6	117.02 (16)	C5—C3—H3A	120.5
C12—C10—C4	119.75 (16)	N1—C2—C1	119.92 (17)
C6—C10—C4	123.22 (17)	N1—C2—H2B	120.0
C4—C9—C8	120.72 (16)	C1—C2—H2B	120.0
C4—C9—H9A	119.6	C7—C1—C2	119.31 (17)
C8—C9—H9A	119.6	C7—C1—H1B	120.3
C11—C8—C7	117.90 (16)	C2—C1—H1B	120.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2^i	0.84 (2)	2.32 (2)	2.944 (2)	132 (2)
N1—H1A···N2	0.84 (2)	2.33 (2)	2.741 (2)	111 (2)

Symmetry code: (i) −x, −y+1, −z+1.