4-Nitro-phthalamide.

In the title compound, C8H7N3O4 (systematic name: 4-nitro-benzene-1,2-dicarboxamide), each of the substituents is twisted out of the plane of the benzene ring to which it is attached [dihedral angles of 11.36 (2)° for the nitro group, and 60.89 (6) and 34.39 (6)° for the amide groups]. The amide groups are orientated to either side of the least-squares plane through the benzene ring with the amine groups being directed furthest apart. In the crystal, a three-dimensional architecture is established by a network of N-H⋯O hydrogen bonds.

Related literature

For background to the synthesis of functional phthalocyanines, see: Chin et al. (2012 ▶). For the structure of the 1,2-dicarboxamide derivative, see: Hamada et al. (2012 ▶). For the synthesis, see: Rasmussen et al. (1978 ▶).

Experimental

Crystal data

C8H7N3O4

M = 209.17

Monoclinic,

a = 7.7425 (2) Å

b = 9.6634 (2) Å

c = 12.1276 (3) Å

β = 106.008 (3)°

V = 872.19 (4) Å3

Z = 4

Cu Kα radiation

μ = 1.13 mm−1

T = 100 K

0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.668, T max = 1.000

7908 measured reflections

1821 independent reflections

1748 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.090

S = 1.03

1821 reflections

164 parameters

4 restraints

All H-atom parameters refined

Δρmax = 0.33 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S1600536814002955/hg5382sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002955/hg5382Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002955/hg5382Isup3.cml

CCDC reference: 985960

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H7N3O4	F(000) = 432
Mr = 209.17	Dx = 1.593 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 4480 reflections
a = 7.7425 (2) Å	θ = 3.8–76.2°
b = 9.6634 (2) Å	µ = 1.13 mm−1
c = 12.1276 (3) Å	T = 100 K
β = 106.008 (3)°	Prism, colourless
V = 872.19 (4) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	1821 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1748 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 10.4041 pixels mm-1	θmax = 76.4°, θmin = 6.0°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −11→12
Tmin = 0.668, Tmax = 1.000	l = −14→15
7908 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0552P)2 + 0.2944P] where P = (Fo2 + 2Fc2)/3
1821 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.33 e Å−3
4 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.61481 (11)	0.80745 (8)	0.55898 (7)	0.0202 (2)
O2	0.54207 (13)	0.79742 (9)	0.37347 (8)	0.0266 (2)
O3	1.04596 (10)	0.17952 (8)	0.51619 (7)	0.0160 (2)
O4	0.91323 (12)	0.23508 (8)	0.72189 (7)	0.0192 (2)
N1	0.60572 (12)	0.74606 (10)	0.46837 (8)	0.0177 (2)
N2	0.76591 (13)	0.09066 (10)	0.45344 (8)	0.0171 (2)
H21	0.6511 (13)	0.1037 (17)	0.4443 (14)	0.025 (4)*
H22	0.809 (2)	0.0070 (11)	0.4535 (14)	0.025 (4)*
N3	1.04060 (14)	0.44255 (10)	0.77908 (8)	0.0182 (2)
H31	1.096 (2)	0.4063 (17)	0.8462 (10)	0.027 (4)*
H32	1.050 (2)	0.5306 (10)	0.7667 (13)	0.025 (4)*
C1	0.67444 (14)	0.60364 (11)	0.47498 (10)	0.0154 (2)
C2	0.63660 (14)	0.52513 (12)	0.37619 (10)	0.0171 (2)
H2	0.566 (2)	0.5640 (18)	0.3011 (14)	0.030 (4)*
C3	0.70007 (15)	0.38986 (12)	0.38425 (10)	0.0164 (2)
H3	0.677 (2)	0.3367 (15)	0.3164 (13)	0.018 (3)*
C4	0.80132 (14)	0.33683 (11)	0.48911 (9)	0.0141 (2)
C5	0.83839 (14)	0.41940 (11)	0.58825 (9)	0.0137 (2)
C6	0.77318 (15)	0.55445 (11)	0.58101 (10)	0.0150 (2)
H6	0.795 (2)	0.6102 (16)	0.6473 (13)	0.019 (3)*
C7	0.88135 (15)	0.19421 (11)	0.49017 (9)	0.0137 (2)
C8	0.93594 (14)	0.35831 (11)	0.70270 (9)	0.0146 (2)

	U11	U22	U33	U12	U13	U23
O1	0.0180 (4)	0.0139 (4)	0.0287 (5)	0.0015 (3)	0.0063 (3)	−0.0027 (3)
O2	0.0284 (5)	0.0171 (4)	0.0269 (5)	0.0051 (3)	−0.0047 (4)	0.0061 (3)
O3	0.0152 (4)	0.0130 (4)	0.0202 (4)	0.0004 (3)	0.0053 (3)	−0.0006 (3)
O4	0.0283 (4)	0.0105 (4)	0.0193 (4)	0.0000 (3)	0.0076 (3)	0.0020 (3)
N1	0.0128 (4)	0.0128 (5)	0.0258 (5)	−0.0002 (3)	0.0024 (4)	0.0013 (4)
N2	0.0153 (5)	0.0111 (5)	0.0246 (5)	0.0009 (4)	0.0049 (4)	−0.0017 (4)
N3	0.0265 (5)	0.0115 (5)	0.0147 (5)	−0.0005 (4)	0.0021 (4)	0.0017 (3)
C1	0.0135 (5)	0.0105 (5)	0.0221 (6)	0.0003 (4)	0.0050 (4)	0.0024 (4)
C2	0.0148 (5)	0.0169 (5)	0.0187 (5)	0.0003 (4)	0.0032 (4)	0.0029 (4)
C3	0.0170 (5)	0.0149 (5)	0.0170 (5)	−0.0009 (4)	0.0045 (4)	−0.0012 (4)
C4	0.0136 (5)	0.0109 (5)	0.0185 (5)	−0.0012 (4)	0.0057 (4)	0.0003 (4)
C5	0.0138 (5)	0.0113 (5)	0.0167 (5)	−0.0008 (4)	0.0053 (4)	0.0012 (4)
C6	0.0157 (5)	0.0118 (5)	0.0180 (5)	−0.0017 (4)	0.0058 (4)	−0.0011 (4)
C7	0.0177 (5)	0.0118 (5)	0.0124 (5)	0.0002 (4)	0.0055 (4)	−0.0002 (4)
C8	0.0177 (5)	0.0112 (5)	0.0161 (5)	0.0018 (4)	0.0069 (4)	−0.0002 (4)

O1—N1	1.2336 (13)	C1—C2	1.3796 (16)
O2—N1	1.2252 (13)	C1—C6	1.3862 (15)
O3—C7	1.2338 (14)	C2—C3	1.3904 (16)
O4—C8	1.2351 (14)	C2—H2	0.997 (16)
N1—C1	1.4698 (14)	C3—C4	1.3945 (15)
N2—C7	1.3338 (14)	C3—H3	0.945 (15)
N2—H21	0.874 (9)	C4—C5	1.4050 (15)
N2—H22	0.875 (9)	C4—C7	1.5097 (14)
N3—C8	1.3280 (15)	C5—C6	1.3934 (15)
N3—H31	0.881 (9)	C5—C8	1.5058 (14)
N3—H32	0.870 (9)	C6—H6	0.943 (16)
O2—N1—O1	123.47 (10)	C4—C3—H3	121.1 (9)
O2—N1—C1	118.45 (10)	C3—C4—C5	120.16 (10)
O1—N1—C1	118.09 (9)	C3—C4—C7	118.00 (9)
C7—N2—H21	119.9 (11)	C5—C4—C7	121.64 (9)
C7—N2—H22	118.1 (11)	C6—C5—C4	119.54 (10)
H21—N2—H22	120.6 (15)	C6—C5—C8	120.41 (10)
C8—N3—H31	116.6 (11)	C4—C5—C8	119.89 (9)
C8—N3—H32	122.9 (10)	C1—C6—C5	118.50 (10)
H31—N3—H32	120.4 (15)	C1—C6—H6	121.1 (9)
C2—C1—C6	123.21 (10)	C5—C6—H6	120.4 (9)
C2—C1—N1	118.72 (10)	O3—C7—N2	123.29 (10)
C6—C1—N1	118.06 (10)	O3—C7—C4	119.99 (9)
C1—C2—C3	118.01 (10)	N2—C7—C4	116.51 (9)
C1—C2—H2	121.2 (10)	O4—C8—N3	123.42 (10)
C3—C2—H2	120.8 (10)	O4—C8—C5	119.37 (10)
C2—C3—C4	120.57 (10)	N3—C8—C5	117.20 (9)
C2—C3—H3	118.2 (9)
O2—N1—C1—C2	−11.31 (15)	C2—C1—C6—C5	0.37 (17)
O1—N1—C1—C2	168.48 (10)	N1—C1—C6—C5	179.78 (9)
O2—N1—C1—C6	169.25 (10)	C4—C5—C6—C1	−0.61 (16)
O1—N1—C1—C6	−10.96 (15)	C8—C5—C6—C1	−176.01 (10)
C6—C1—C2—C3	0.44 (17)	C3—C4—C7—O3	114.92 (12)
N1—C1—C2—C3	−178.96 (10)	C5—C4—C7—O3	−60.00 (14)
C1—C2—C3—C4	−1.02 (16)	C3—C4—C7—N2	−60.02 (13)
C2—C3—C4—C5	0.79 (16)	C5—C4—C7—N2	125.05 (11)
C2—C3—C4—C7	−174.21 (10)	C6—C5—C8—O4	142.80 (11)
C3—C4—C5—C6	0.05 (16)	C4—C5—C8—O4	−32.58 (15)
C7—C4—C5—C6	174.86 (9)	C6—C5—C8—N3	−35.96 (14)
C3—C4—C5—C8	175.47 (10)	C4—C5—C8—N3	148.66 (11)
C7—C4—C5—C8	−9.71 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O1i	0.87 (1)	2.22 (1)	3.0718 (13)	164 (2)
N2—H22···O3ii	0.88 (1)	2.10 (1)	2.9628 (12)	168 (2)
N3—H31···O1iii	0.88 (1)	2.42 (1)	3.1288 (13)	138 (1)
N3—H31···O3iv	0.88 (1)	2.35 (1)	3.0979 (12)	143 (1)
N3—H32···O4v	0.87 (1)	2.00 (1)	2.8498 (13)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O1i	0.87 (1)	2.22 (1)	3.0718 (13)	164 (2)
N2—H22⋯O3ii	0.88 (1)	2.10 (1)	2.9628 (12)	168 (2)
N3—H31⋯O1iii	0.88 (1)	2.42 (1)	3.1288 (13)	138 (1)
N3—H31⋯O3iv	0.88 (1)	2.35 (1)	3.0979 (12)	143 (1)
N3—H32⋯O4v	0.87 (1)	2.00 (1)	2.8498 (13)	167 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .