2,9-Dimethyl-1,10-phenanthrolinium nitrate

The title compound, C₁₄H₁₃N₂⁺·NO₃⁻, is a protonated amine salt compound. A nitrate ion acts as hydrogen-bond acceptor of N—H...O and C—H...O hydrogen bonds, connecting the cations and anions into layers running parallel to the ab plane. The packing is additionally stabilized by π–π inter­actions between phenanthroline ring systems.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.127
• Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N3
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

2,9-Dimethyl-1,10-phenanthrolinium nitrate

Crystal data

C14H13N2^+·NO3^−	Z = 2
Mr = 271.27	F(000) = 284
Triclinic, P1	Dx = 1.448 Mg m^−3
a = 6.8971 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8366 (14) Å	Cell parameters from 1328 reflections
c = 10.1800 (14) Å	θ = 2.4–25.8°
α = 64.443 (2)°	µ = 0.11 mm^−1
β = 86.796 (2)°	T = 293 K
γ = 87.896 (2)°	Plate, pale yellow
V = 622.04 (15) Å^3	0.39 × 0.29 × 0.09 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2396 independent reflections
Radiation source: fine-focus sealed tube	1870 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 2.2°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→12
Tmin = 0.960, Tmax = 0.991	l = −9→12
3616 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	All H-atom parameters refined
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0703P)^2 + 0.0925P] where P = (Fo^2 + 2Fc^2)/3
2396 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.23 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 > 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	0.3978 (2)	0.15715 (18)	0.30079 (19)	0.0818 (5)
O2	0.2283 (3)	0.20327 (16)	0.11479 (14)	0.0748 (5)
O3	0.1038 (2)	0.23548 (15)	0.29714 (15)	0.0620 (4)
N1	0.26108 (18)	0.54812 (14)	0.24159 (13)	0.0363 (3)
N2	0.20949 (18)	0.32448 (14)	0.51710 (14)	0.0347 (3)
N3	0.2446 (2)	0.19900 (15)	0.23652 (16)	0.0471 (4)
C1	0.2657 (4)	0.6152 (3)	−0.0164 (2)	0.0546 (5)
C2	0.2827 (2)	0.65645 (18)	0.10747 (17)	0.0395 (4)
C3	0.3178 (3)	0.8069 (2)	0.0816 (2)	0.0466 (4)
C4	0.3276 (2)	0.8451 (2)	0.1939 (2)	0.0458 (4)
C5	0.3029 (2)	0.73240 (18)	0.33830 (18)	0.0378 (4)
C6	0.3104 (2)	0.7606 (2)	0.4643 (2)	0.0448 (4)
C7	0.2833 (2)	0.6488 (2)	0.5989 (2)	0.0445 (4)
C8	0.2471 (2)	0.49813 (18)	0.62129 (17)	0.0373 (4)
C9	0.2171 (2)	0.3772 (2)	0.75899 (18)	0.0443 (4)
C10	0.1880 (2)	0.2356 (2)	0.77153 (18)	0.0448 (4)
C11	0.1851 (2)	0.20789 (18)	0.64803 (17)	0.0401 (4)
C12	0.2421 (2)	0.46769 (16)	0.49858 (16)	0.0325 (3)
C13	0.2695 (2)	0.58573 (16)	0.35403 (16)	0.0329 (3)
C14	0.1591 (4)	0.0562 (2)	0.6545 (2)	0.0550 (5)
H4	0.351 (2)	0.947 (2)	0.1726 (19)	0.048 (5)*
H10	0.167 (3)	0.153 (2)	0.863 (2)	0.058 (5)*
H1N2	0.204 (3)	0.309 (2)	0.436 (2)	0.056 (5)*
H3	0.339 (3)	0.881 (2)	−0.014 (2)	0.059 (5)*
H6	0.337 (3)	0.863 (2)	0.451 (2)	0.059 (5)*
H9	0.215 (3)	0.395 (2)	0.847 (2)	0.056 (5)*
H14B	0.101 (4)	0.057 (3)	0.573 (3)	0.093 (8)*
H7	0.285 (3)	0.668 (2)	0.679 (2)	0.069 (6)*
H14A	0.083 (4)	−0.006 (3)	0.738 (3)	0.088 (8)*
H1A	0.156 (4)	0.660 (3)	−0.068 (3)	0.090 (8)*
H1C	0.245 (3)	0.506 (3)	0.017 (3)	0.080 (7)*
H14C	0.274 (4)	0.003 (3)	0.665 (3)	0.088 (8)*
H1B	0.367 (4)	0.651 (3)	−0.083 (3)	0.094 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0629 (10)	0.0824 (11)	0.0903 (12)	0.0023 (8)	−0.0171 (8)	−0.0264 (9)
O2	0.1237 (13)	0.0645 (9)	0.0416 (8)	0.0040 (8)	−0.0002 (8)	−0.0286 (7)
O3	0.0630 (9)	0.0703 (9)	0.0652 (9)	−0.0060 (7)	0.0093 (7)	−0.0420 (7)
N1	0.0404 (7)	0.0402 (7)	0.0296 (7)	0.0013 (5)	−0.0023 (5)	−0.0163 (6)
N2	0.0351 (7)	0.0398 (7)	0.0300 (7)	0.0001 (5)	−0.0013 (5)	−0.0159 (6)
N3	0.0621 (10)	0.0341 (7)	0.0429 (8)	−0.0084 (6)	0.0031 (7)	−0.0145 (6)
C1	0.0722 (14)	0.0588 (12)	0.0317 (10)	−0.0020 (11)	−0.0041 (10)	−0.0182 (9)
C2	0.0393 (9)	0.0441 (9)	0.0322 (8)	0.0031 (7)	−0.0010 (6)	−0.0139 (7)
C3	0.0496 (10)	0.0426 (9)	0.0365 (9)	0.0001 (7)	0.0009 (7)	−0.0071 (8)
C4	0.0456 (10)	0.0364 (9)	0.0514 (11)	−0.0009 (7)	0.0008 (7)	−0.0154 (8)
C5	0.0321 (8)	0.0406 (8)	0.0428 (9)	0.0010 (6)	−0.0003 (6)	−0.0203 (7)
C6	0.0433 (9)	0.0469 (10)	0.0548 (11)	−0.0009 (7)	−0.0026 (7)	−0.0319 (9)
C7	0.0434 (9)	0.0590 (11)	0.0452 (10)	0.0013 (8)	−0.0037 (7)	−0.0357 (9)
C8	0.0296 (8)	0.0530 (9)	0.0346 (8)	0.0022 (6)	−0.0023 (6)	−0.0240 (7)
C9	0.0391 (9)	0.0644 (11)	0.0319 (9)	0.0022 (7)	−0.0018 (7)	−0.0232 (8)
C10	0.0408 (9)	0.0550 (11)	0.0300 (9)	0.0012 (7)	−0.0012 (7)	−0.0103 (8)
C11	0.0344 (8)	0.0440 (9)	0.0358 (8)	0.0005 (6)	−0.0018 (6)	−0.0116 (7)
C12	0.0280 (8)	0.0390 (8)	0.0330 (8)	0.0018 (6)	−0.0025 (6)	−0.0179 (7)
C13	0.0290 (8)	0.0385 (8)	0.0326 (8)	0.0017 (6)	−0.0013 (6)	−0.0167 (7)
C14	0.0659 (13)	0.0421 (10)	0.0498 (12)	−0.0034 (9)	−0.0027 (10)	−0.0129 (9)

Geometric parameters (Å, º)

O1—N3	1.236 (2)	C5—C13	1.408 (2)
O2—N3	1.2330 (19)	C5—C6	1.429 (2)
O3—N3	1.2455 (19)	C6—C7	1.345 (3)
N1—C2	1.325 (2)	C6—H6	0.98 (2)
N1—C13	1.3509 (19)	C7—C8	1.428 (2)
N2—C11	1.338 (2)	C7—H7	0.91 (2)
N2—C12	1.364 (2)	C8—C9	1.403 (2)
N2—H1N2	0.90 (2)	C8—C12	1.407 (2)
C1—C2	1.493 (2)	C9—C10	1.364 (3)
C1—H1A	0.93 (3)	C9—H9	0.99 (2)
C1—H1C	0.99 (3)	C10—C11	1.398 (2)
C1—H1B	0.91 (3)	C10—H10	0.94 (2)
C2—C3	1.414 (2)	C11—C14	1.483 (3)
C3—C4	1.354 (3)	C12—C13	1.435 (2)
C3—H3	0.94 (2)	C14—H14B	0.94 (3)
C4—C5	1.414 (2)	C14—H14A	0.95 (3)
C4—H4	0.950 (19)	C14—H14C	0.92 (3)
C2—N1—C13	118.07 (13)	C6—C7—C8	121.51 (16)
C11—N2—C12	123.27 (14)	C6—C7—H7	120.5 (13)
C11—N2—H1N2	119.2 (12)	C8—C7—H7	118.0 (13)
C12—N2—H1N2	117.6 (12)	C9—C8—C12	117.52 (15)
O2—N3—O1	121.19 (18)	C9—C8—C7	123.99 (15)
O2—N3—O3	119.70 (16)	C12—C8—C7	118.49 (15)
O1—N3—O3	119.11 (16)	C10—C9—C8	120.49 (16)
C2—C1—H1A	110.7 (16)	C10—C9—H9	119.7 (11)
C2—C1—H1C	112.2 (14)	C8—C9—H9	119.8 (11)
H1A—C1—H1C	104 (2)	C9—C10—C11	120.96 (16)
C2—C1—H1B	111.8 (17)	C9—C10—H10	121.6 (12)
H1A—C1—H1B	105 (2)	C11—C10—H10	117.4 (12)
H1C—C1—H1B	113 (2)	N2—C11—C10	118.11 (15)
N1—C2—C3	121.42 (15)	N2—C11—C14	118.33 (16)
N1—C2—C1	117.80 (15)	C10—C11—C14	123.55 (16)
C3—C2—C1	120.78 (15)	N2—C12—C8	119.62 (14)
C4—C3—C2	120.76 (16)	N2—C12—C13	119.56 (13)
C4—C3—H3	119.0 (12)	C8—C12—C13	120.82 (14)
C2—C3—H3	120.2 (12)	N1—C13—C5	124.29 (14)
C3—C4—C5	119.22 (16)	N1—C13—C12	117.43 (13)
C3—C4—H4	118.6 (11)	C5—C13—C12	118.28 (14)
C5—C4—H4	122.2 (11)	C11—C14—H14B	114.4 (16)
C13—C5—C4	116.23 (15)	C11—C14—H14A	111.8 (15)
C13—C5—C6	120.07 (15)	H14B—C14—H14A	107 (2)
C4—C5—C6	123.70 (15)	C11—C14—H14C	112.4 (16)
C7—C6—C5	120.82 (16)	H14B—C14—H14C	107 (2)
C7—C6—H6	120.7 (11)	H14A—C14—H14C	103 (2)
C5—C6—H6	118.5 (12)
C13—N1—C2—C3	1.4 (2)	C9—C10—C11—C14	178.44 (17)
C13—N1—C2—C1	−177.71 (16)	C11—N2—C12—C8	−1.4 (2)
N1—C2—C3—C4	−1.0 (3)	C11—N2—C12—C13	179.10 (13)
C1—C2—C3—C4	178.09 (17)	C9—C8—C12—N2	−0.2 (2)
C2—C3—C4—C5	0.2 (3)	C7—C8—C12—N2	179.47 (13)
C3—C4—C5—C13	0.1 (2)	C9—C8—C12—C13	179.32 (13)
C3—C4—C5—C6	−179.96 (15)	C7—C8—C12—C13	−1.0 (2)
C13—C5—C6—C7	−0.9 (2)	C2—N1—C13—C5	−1.1 (2)
C4—C5—C6—C7	179.15 (15)	C2—N1—C13—C12	178.83 (12)
C5—C6—C7—C8	0.4 (3)	C4—C5—C13—N1	0.3 (2)
C6—C7—C8—C9	−179.76 (15)	C6—C5—C13—N1	−179.60 (14)
C6—C7—C8—C12	0.6 (2)	C4—C5—C13—C12	−179.57 (13)
C12—C8—C9—C10	1.2 (2)	C6—C5—C13—C12	0.5 (2)
C7—C8—C9—C10	−178.42 (15)	N2—C12—C13—N1	0.1 (2)
C8—C9—C10—C11	−0.8 (3)	C8—C12—C13—N1	−179.45 (13)
C12—N2—C11—C10	1.8 (2)	N2—C12—C13—C5	179.99 (12)
C12—N2—C11—C14	−177.38 (15)	C8—C12—C13—C5	0.5 (2)
C9—C10—C11—N2	−0.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O3	0.90 (2)	2.01 (2)	2.869 (2)	159 (2)
N2—H1N2···N1	0.90 (2)	2.36 (2)	2.730 (2)	104 (2)
C4—H4···O2^i	0.95 (2)	2.46 (2)	3.312 (3)	150 (2)
C9—H9···O2^ii	0.98 (2)	2.56 (2)	3.275 (2)	129 (2)
C14—H14B···O3	0.94 (3)	2.59 (3)	3.326 (2)	136 (2)

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