6-Nitro-1,10-phenanthrolin-5-amine

In the title compound, C₁₂H₈N₄O₂, the dihedral angle between the phenanthroline ring system and the nitro group is 23.75 (14)°. The mol­ecule features intra­molecular N—H...O and C—H...O hydrogen bonds. In the crystal, N—H...(N,N), C—H...N and C—H...O hydrogen bonds link the mol­ecules into [100] chains.

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT414_ALERT_2_C Short Intra D-H..H-X       H3       ..H4A              1.92 Ang.
                                                      x,y,z  =      1_555 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.093 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          7 Note

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT333_ALERT_2_G Large Aver C6-Ring C-C Dist C4       -C12      .       1.43 Ang.
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          3 Info
PLAT882_ALERT_1_G No Datum for _diffrn_reflns_av_unetI/netI ......     Please Do !
PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary .     Please Do !
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         13 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          7 Note
PLAT955_ALERT_1_G Reported (CIF) and Actual (FCF) Lmax Differ by .          1 Units
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          6 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

6-Nitro-1,10-phenanthrolin-5-amine

Crystal data

C12H8N4O2	F(000) = 992
Mr = 240.22	Dx = 1.58 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1396 reflections
a = 14.265 (8) Å	θ = 3.7–23.4°
b = 8.060 (4) Å	µ = 0.11 mm^−1
c = 17.564 (9) Å	T = 100 K
V = 2019.4 (19) Å^3	Cuboid, yellow
Z = 8	0.37 × 0.12 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer	1204 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.093
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 28.0°, θmin = 4.0°
Tmin = 0.984, Tmax = 0.99	h = −18→18
13477 measured reflections	k = −7→10
2426 independent reflections	l = −22→23

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.058	w = 1/[σ^2(Fo^2) + (0.0669P)^2 + 0.4998P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.176	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.36 e Å^−3
2426 reflections	Δρmin = −0.39 e Å^−3
172 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2015)
0 restraints	Extinction coefficient: 0.0047 (14)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Aromatic H atoms were positioned geometrically with a C—H distance of 0.95 Å and constrained to ride on their parent atoms with U_iso (H) = 1.2 U_eq(C).

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

	x	y	z	Uiso*/Ueq
N1	0.40826 (14)	0.4435 (3)	0.33237 (13)	0.0383 (6)
C12	0.26583 (16)	0.3587 (3)	0.27163 (14)	0.0286 (6)
C6	0.15781 (17)	0.5134 (3)	0.38771 (14)	0.0309 (6)
C7	0.25963 (17)	0.5190 (3)	0.39240 (14)	0.0300 (6)
C11	0.31313 (17)	0.4415 (3)	0.33443 (15)	0.0305 (6)
C4	0.16718 (16)	0.3585 (3)	0.26734 (14)	0.0284 (6)
N2	0.32090 (15)	0.2864 (3)	0.21825 (13)	0.0356 (6)
N3	0.01725 (16)	0.4325 (3)	0.31972 (18)	0.0445 (7)
C5	0.11029 (17)	0.4399 (3)	0.32623 (15)	0.0311 (6)
O1	0.02003 (14)	0.6244 (3)	0.43663 (12)	0.0562 (7)
N4	0.10335 (16)	0.5857 (3)	0.44757 (14)	0.0421 (6)
C9	0.40771 (19)	0.6088 (4)	0.44486 (17)	0.0458 (8)
H7	0.442575	0.66799	0.482097	0.055*
C8	0.31192 (19)	0.6052 (4)	0.44809 (16)	0.0404 (7)
H6	0.280266	0.661066	0.488166	0.048*
C1	0.27861 (19)	0.2137 (4)	0.15956 (15)	0.0393 (7)
H1	0.316626	0.164069	0.121416	0.047*
C3	0.12573 (19)	0.2785 (3)	0.20499 (15)	0.0364 (7)
H3	0.059429	0.274357	0.200254	0.044*
C2	0.18162 (19)	0.2063 (4)	0.15100 (16)	0.0383 (7)
H2	0.154655	0.151906	0.108296	0.046*
C10	0.4533 (2)	0.5254 (4)	0.38678 (18)	0.0471 (8)
H8	0.51987	0.526878	0.385799	0.057*
O2	0.13845 (16)	0.6016 (4)	0.51179 (13)	0.0786 (9)
H4A	−0.009 (2)	0.385 (4)	0.2794 (19)	0.062 (11)*
H4B	−0.020 (3)	0.483 (5)	0.356 (2)	0.089 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0250 (12)	0.0449 (14)	0.0449 (15)	−0.0012 (10)	−0.0059 (10)	−0.0005 (11)
C12	0.0267 (13)	0.0276 (13)	0.0316 (15)	0.0004 (10)	−0.0020 (11)	0.0042 (11)
C6	0.0295 (14)	0.0318 (15)	0.0314 (16)	0.0029 (11)	0.0023 (11)	0.0023 (11)
C7	0.0311 (13)	0.0289 (13)	0.0299 (15)	0.0011 (10)	−0.0031 (11)	0.0039 (11)
C11	0.0241 (13)	0.0319 (14)	0.0357 (17)	−0.0018 (10)	−0.0045 (11)	0.0059 (12)
C4	0.0250 (13)	0.0297 (13)	0.0305 (15)	−0.0010 (11)	−0.0015 (11)	0.0049 (11)
N2	0.0286 (12)	0.0423 (14)	0.0359 (14)	0.0018 (10)	0.0011 (10)	−0.0001 (11)
N3	0.0244 (12)	0.0594 (17)	0.0496 (18)	0.0033 (11)	−0.0012 (12)	−0.0095 (14)
C5	0.0249 (13)	0.0335 (14)	0.0349 (16)	−0.0005 (10)	0.0005 (11)	0.0040 (12)
O1	0.0419 (12)	0.0726 (16)	0.0540 (15)	0.0196 (11)	0.0072 (10)	−0.0093 (11)
N4	0.0380 (14)	0.0534 (16)	0.0349 (15)	−0.0023 (12)	0.0047 (12)	−0.0033 (11)
C9	0.0395 (17)	0.0499 (19)	0.048 (2)	−0.0064 (14)	−0.0132 (14)	−0.0088 (15)
C8	0.0392 (16)	0.0405 (16)	0.0415 (18)	−0.0008 (13)	−0.0048 (13)	−0.0052 (13)
C1	0.0400 (16)	0.0447 (17)	0.0331 (17)	0.0039 (13)	0.0041 (13)	0.0003 (13)
C3	0.0293 (14)	0.0395 (16)	0.0405 (17)	−0.0023 (12)	−0.0049 (12)	0.0011 (13)
C2	0.0392 (15)	0.0423 (17)	0.0333 (17)	−0.0042 (13)	−0.0035 (12)	−0.0008 (13)
C10	0.0269 (14)	0.0532 (19)	0.061 (2)	−0.0059 (13)	−0.0116 (14)	−0.0047 (16)
O2	0.0519 (15)	0.142 (3)	0.0419 (15)	−0.0144 (15)	0.0048 (12)	−0.0285 (14)

Geometric parameters (Å, º)

N1—C10	1.327 (3)	N3—H4A	0.89 (3)
N1—C11	1.358 (3)	N3—H4B	0.93 (4)
C12—N2	1.355 (3)	O1—N4	1.244 (3)
C12—C4	1.409 (3)	N4—O2	1.241 (3)
C12—C11	1.455 (3)	C9—C8	1.368 (4)
C6—C5	1.406 (4)	C9—C10	1.384 (4)
C6—N4	1.431 (3)	C9—H7	0.95
C6—C7	1.456 (3)	C8—H6	0.95
C7—C8	1.413 (4)	C1—C2	1.393 (4)
C7—C11	1.418 (4)	C1—H1	0.95
C4—C3	1.402 (4)	C3—C2	1.369 (4)
C4—C5	1.469 (4)	C3—H3	0.95
N2—C1	1.331 (3)	C2—H2	0.95
N3—C5	1.333 (3)	C10—H8	0.95
C10—N1—C11	118.1 (2)	C6—C5—C4	117.5 (2)
N2—C12—C4	122.8 (2)	O2—N4—O1	120.0 (2)
N2—C12—C11	116.9 (2)	O2—N4—C6	119.4 (2)
C4—C12—C11	120.3 (2)	O1—N4—C6	120.5 (2)
C5—C6—N4	118.3 (2)	C8—C9—C10	119.3 (3)
C5—C6—C7	122.5 (2)	C8—C9—H7	120.4
N4—C6—C7	119.2 (2)	C10—C9—H7	120.4
C8—C7—C11	115.5 (2)	C9—C8—C7	120.6 (3)
C8—C7—C6	125.6 (2)	C9—C8—H6	119.7
C11—C7—C6	118.9 (2)	C7—C8—H6	119.7
N1—C11—C7	123.5 (2)	N2—C1—C2	123.6 (3)
N1—C11—C12	116.7 (2)	N2—C1—H1	118.2
C7—C11—C12	119.8 (2)	C2—C1—H1	118.2
C3—C4—C12	117.6 (2)	C2—C3—C4	119.4 (2)
C3—C4—C5	121.5 (2)	C2—C3—H3	120.3
C12—C4—C5	120.9 (2)	C4—C3—H3	120.3
C1—N2—C12	117.6 (2)	C3—C2—C1	119.1 (3)
C5—N3—H4A	121 (2)	C3—C2—H2	120.5
C5—N3—H4B	119 (2)	C1—C2—H2	120.5
H4A—N3—H4B	120 (3)	N1—C10—C9	123.0 (3)
N3—C5—C6	124.4 (3)	N1—C10—H8	118.5
N3—C5—C4	118.0 (3)	C9—C10—H8	118.5
C5—C6—C7—C8	173.1 (3)	C7—C6—C5—N3	−179.8 (2)
N4—C6—C7—C8	−6.7 (4)	N4—C6—C5—C4	−176.8 (2)
C5—C6—C7—C11	−2.7 (4)	C7—C6—C5—C4	3.4 (4)
N4—C6—C7—C11	177.5 (2)	C3—C4—C5—N3	1.4 (4)
C10—N1—C11—C7	−1.4 (4)	C12—C4—C5—N3	−178.7 (2)
C10—N1—C11—C12	176.6 (2)	C3—C4—C5—C6	178.4 (2)
C8—C7—C11—N1	1.9 (4)	C12—C4—C5—C6	−1.7 (4)
C6—C7—C11—N1	178.2 (2)	C5—C6—N4—O2	156.5 (3)
C8—C7—C11—C12	−176.0 (2)	C7—C6—N4—O2	−23.7 (4)
C6—C7—C11—C12	0.2 (3)	C5—C6—N4—O1	−19.7 (4)
N2—C12—C11—N1	2.2 (3)	C7—C6—N4—O1	160.1 (3)
C4—C12—C11—N1	−176.7 (2)	C10—C9—C8—C7	−0.7 (4)
N2—C12—C11—C7	−179.7 (2)	C11—C7—C8—C9	−0.8 (4)
C4—C12—C11—C7	1.4 (4)	C6—C7—C8—C9	−176.7 (3)
N2—C12—C4—C3	0.4 (4)	C12—N2—C1—C2	−1.0 (4)
C11—C12—C4—C3	179.2 (2)	C12—C4—C3—C2	−0.7 (4)
N2—C12—C4—C5	−179.4 (2)	C5—C4—C3—C2	179.1 (2)
C11—C12—C4—C5	−0.6 (4)	C4—C3—C2—C1	0.2 (4)
C4—C12—N2—C1	0.4 (4)	N2—C1—C2—C3	0.6 (4)
C11—C12—N2—C1	−178.4 (2)	C11—N1—C10—C9	−0.3 (4)
N4—C6—C5—N3	−0.1 (4)	C8—C9—C10—N1	1.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H4A···N1^i	0.89 (3)	2.34 (3)	3.092 (4)	143 (3)
N3—H4A···N2^i	0.89 (3)	2.55 (3)	3.111 (4)	122 (2)
N3—H4B···O1	0.93 (4)	1.90 (4)	2.571 (4)	127 (3)
C3—H3···N1^i	0.95	2.61	3.438 (4)	145
C8—H6···O2	0.95	2.12	2.716 (4)	119
C9—H7···O1^ii	0.95	2.46	3.395 (4)	167

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