Bis(1,10-phenanthroline-5,6-dione) diamino­glyoxime

In the crystal structure of the title cocrystal, 2C₁₂H₆N₂O₂·C₂H₆N₄O₂, the diamino­glyoxime mol­ecules are located on inversion centres, while the 1,10-phenanthroline-5,6-dione mol­ecules are located in general positions. Both mol­ecules are connected through inter­molecular N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 220 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.136
• Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT432_ALERT_2_B Short Inter X...Y Contact  O3     ..  C1      ..       2.78 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C12    ...       1.53 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C12     ..       2.93 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

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

   4 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
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: IPDS Program Package (Stoe & Cie, 1998); cell refinement: IPDS Program Package; data reduction: IPDS Program Package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL.

Bis(1,10-phenanthroline-5,6-dione) diaminoglyoxime

Crystal data

2C12H6N2O2·C2H6N4O2	Z = 1
Mr = 538.48	F(000) = 278
Triclinic, P1	Dx = 1.528 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1513 (8) Å	Cell parameters from 2741 reflections
b = 9.3637 (14) Å	θ = 3.5–28°
c = 9.6271 (12) Å	µ = 0.11 mm^−1
α = 78.712 (16)°	T = 220 K
β = 81.427 (15)°	Block, red
γ = 68.269 (15)°	0.30 × 0.15 × 0.15 mm
V = 585.18 (13) Å^3

Data collection

Stoe IPDS-1 diffractometer	1395 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
Graphite monochromator	θmax = 25.0°, θmin = 3.2°
φ scans	h = −8→8
3472 measured reflections	k = −11→11
1991 independent reflections	l = −11→11

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0876P)^2] where P = (Fo^2 + 2Fc^2)/3
1991 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.0596 (2)	0.39276 (18)	0.77530 (17)	0.0469 (5)
O2	0.1168 (3)	0.1953 (2)	0.58301 (16)	0.0538 (5)
N1	0.2401 (3)	−0.0160 (2)	1.14428 (18)	0.0369 (5)
N2	0.4397 (3)	−0.2012 (2)	0.95105 (18)	0.0349 (4)
C1	0.0466 (3)	0.2604 (2)	0.8161 (2)	0.0330 (5)
C2	0.0791 (3)	0.1982 (2)	0.9673 (2)	0.0296 (5)
C3	−0.0183 (4)	0.2898 (3)	1.0729 (3)	0.0414 (6)
H3	−0.1058	0.3928	1.0491	0.050*
C4	0.0155 (4)	0.2272 (3)	1.2118 (3)	0.0484 (6)
H4	−0.0483	0.2866	1.2851	0.058*
C5	0.1447 (4)	0.0757 (3)	1.2424 (2)	0.0464 (6)
H5	0.1671	0.0343	1.3381	0.056*
C6	0.2083 (3)	0.0460 (2)	1.0079 (2)	0.0274 (5)
C7	0.3172 (3)	−0.0578 (2)	0.9010 (2)	0.0277 (5)
C8	0.5392 (4)	−0.2962 (3)	0.8578 (3)	0.0451 (6)
H8	0.6241	−0.3970	0.8925	0.054*
C9	0.5255 (4)	−0.2559 (3)	0.7116 (3)	0.0464 (6)
H9	0.6011	−0.3265	0.6492	0.056*
C10	0.3983 (4)	−0.1099 (3)	0.6613 (2)	0.0406 (6)
H10	0.3832	−0.0794	0.5634	0.049*
C11	0.2917 (3)	−0.0071 (2)	0.7566 (2)	0.0303 (5)
C12	0.1518 (3)	0.1506 (2)	0.7064 (2)	0.0343 (5)
O3	0.4122 (3)	0.3105 (2)	0.75937 (17)	0.0543 (5)
H1O1	0.4965	0.2558	0.8165	0.081*
N3	0.5422 (3)	0.3635 (2)	0.65360 (19)	0.0427 (5)
H1N3	0.1713	0.4667	0.6103	0.064*
H2N3	0.1855	0.5876	0.4807	0.064*
N4	0.2380 (3)	0.5176 (2)	0.55172 (19)	0.0421 (5)
C13	0.4401 (3)	0.4660 (2)	0.5576 (2)	0.0315 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0374 (9)	0.0316 (9)	0.0574 (10)	−0.0008 (7)	−0.0109 (7)	0.0086 (7)
O2	0.0679 (13)	0.0519 (10)	0.0327 (9)	−0.0121 (9)	−0.0220 (8)	0.0091 (7)
N1	0.0401 (11)	0.0429 (11)	0.0288 (9)	−0.0176 (9)	−0.0101 (7)	0.0031 (8)
N2	0.0303 (10)	0.0268 (9)	0.0419 (10)	−0.0042 (8)	−0.0099 (8)	0.0013 (7)
C1	0.0247 (11)	0.0285 (11)	0.0425 (12)	−0.0076 (9)	−0.0101 (9)	0.0044 (9)
C2	0.0252 (10)	0.0291 (10)	0.0351 (11)	−0.0106 (9)	−0.0041 (8)	−0.0026 (8)
C3	0.0317 (12)	0.0372 (12)	0.0566 (14)	−0.0114 (10)	0.0000 (10)	−0.0146 (10)
C4	0.0464 (15)	0.0648 (17)	0.0454 (13)	−0.0279 (14)	0.0075 (11)	−0.0262 (12)
C5	0.0529 (15)	0.0677 (17)	0.0284 (11)	−0.0320 (14)	−0.0037 (10)	−0.0083 (11)
C6	0.0252 (10)	0.0300 (10)	0.0282 (10)	−0.0113 (9)	−0.0082 (8)	0.0008 (8)
C7	0.0225 (10)	0.0260 (10)	0.0335 (10)	−0.0079 (8)	−0.0077 (8)	0.0007 (8)
C8	0.0341 (13)	0.0302 (12)	0.0644 (15)	−0.0017 (10)	−0.0099 (11)	−0.0070 (11)
C9	0.0360 (13)	0.0452 (14)	0.0594 (15)	−0.0088 (11)	−0.0012 (11)	−0.0243 (11)
C10	0.0400 (13)	0.0500 (14)	0.0355 (11)	−0.0180 (12)	−0.0033 (9)	−0.0103 (10)
C11	0.0293 (11)	0.0313 (11)	0.0308 (10)	−0.0114 (9)	−0.0072 (8)	−0.0007 (8)
C12	0.0342 (12)	0.0350 (12)	0.0319 (11)	−0.0124 (10)	−0.0118 (9)	0.0065 (9)
O3	0.0429 (10)	0.0670 (12)	0.0475 (9)	−0.0269 (9)	−0.0218 (8)	0.0324 (8)
N3	0.0425 (11)	0.0449 (11)	0.0385 (10)	−0.0198 (10)	−0.0149 (8)	0.0161 (8)
N4	0.0357 (11)	0.0432 (11)	0.0370 (10)	−0.0085 (9)	−0.0091 (8)	0.0113 (8)
C13	0.0347 (11)	0.0265 (10)	0.0318 (10)	−0.0086 (9)	−0.0108 (8)	0.0004 (8)

Geometric parameters (Å, º)

O1—C1	1.212 (3)	C7—C11	1.395 (3)
O2—C12	1.211 (2)	C8—C9	1.393 (3)
N1—C5	1.336 (3)	C8—H8	0.9400
N1—C6	1.343 (2)	C9—C10	1.372 (3)
N2—C8	1.326 (3)	C9—H9	0.9400
N2—C7	1.343 (3)	C10—C11	1.394 (3)
C1—C2	1.476 (3)	C10—H10	0.9400
C1—C12	1.534 (3)	C11—C12	1.478 (3)
C2—C3	1.394 (3)	O3—N3	1.417 (3)
C2—C6	1.397 (3)	O3—H1O1	0.8300
C3—C4	1.370 (3)	N3—C13	1.283 (3)
C3—H3	0.9400	N4—C13	1.350 (3)
C4—C5	1.379 (4)	N4—H1N3	0.8701
C4—H4	0.9400	N4—H2N3	0.8701
C5—H5	0.9400	C13—C13^i	1.487 (4)
C6—C7	1.484 (3)
C5—N1—C6	117.1 (2)	N2—C8—C9	124.0 (2)
C8—N2—C7	117.77 (18)	N2—C8—H8	118.0
O1—C1—C2	123.2 (2)	C9—C8—H8	118.0
O1—C1—C12	118.90 (19)	C10—C9—C8	117.9 (2)
C2—C1—C12	117.86 (17)	C10—C9—H9	121.0
C3—C2—C6	118.37 (19)	C8—C9—H9	121.0
C3—C2—C1	120.82 (19)	C9—C10—C11	119.4 (2)
C6—C2—C1	120.81 (18)	C9—C10—H10	120.3
C4—C3—C2	118.9 (2)	C11—C10—H10	120.3
C4—C3—H3	120.5	C10—C11—C7	118.33 (19)
C2—C3—H3	120.5	C10—C11—C12	120.93 (18)
C3—C4—C5	118.8 (2)	C7—C11—C12	120.73 (18)
C3—C4—H4	120.6	O2—C12—C11	122.6 (2)
C5—C4—H4	120.6	O2—C12—C1	119.19 (18)
N1—C5—C4	124.0 (2)	C11—C12—C1	118.25 (17)
N1—C5—H5	118.0	N3—O3—H1O1	98.7
C4—C5—H5	118.0	C13—N3—O3	110.48 (19)
N1—C6—C2	122.77 (19)	C13—N4—H1N3	117.3
N1—C6—C7	115.99 (17)	C13—N4—H2N3	118.4
C2—C6—C7	121.23 (17)	H1N3—N4—H2N3	123.3
N2—C7—C11	122.50 (18)	N3—C13—N4	126.7 (2)
N2—C7—C6	116.53 (17)	N3—C13—C13^i	115.5 (2)
C11—C7—C6	120.97 (17)	N4—C13—C13^i	117.8 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O1···N2^ii	0.83	2.27	2.984 (2)	144
O3—H1O1···N1^ii	0.83	2.34	3.043 (3)	143
N4—H1N3···O1	0.87	2.32	3.166 (3)	166
N4—H2N3···O2^iii	0.87	2.42	3.149 (3)	142

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