A second ortho­rhom­bic polymorph of 5-nitro­isophthalic acid monohydrate

In the title compound, C₈H₅NO₆·H₂O, the benzene ring and one of the two carboxylic acid groups are nearly coplanar, whereas the other carboxylic acid group and the nitro group are slightly twisted away from the benzene ring. The mol­ecules are connected by C—H...O inter­actions involving the nitro groups and by O—H...O hydrogen bonds between the water mol­ecules and the carboxylic acid groups, forming a two-dimensional network parallel to the (001) plane.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.042
• wR factor = 0.114
• Data-to-parameter ratio = 30.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O1     -   N1      ..       5.08 su
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1A    ..  H4B     ..       2.14 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       H1B    ..  H4B     ..       2.10 Ang.
PLAT430_ALERT_2_C Short Inter D...A Contact  O1     ..  O2      ..       2.86 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C8      ..       2.97 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O1     ..  C7      ..       3.00 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O6     ..  C7      ..       2.97 Ang.

   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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: H.K. Fun is supervisor of Shea-Lin Ng whereas Muhammad I. Saleh is supervisor of Weng-Thim Tham, Rohana Adnan and Eny Kusrini in this collaborative publication. School of Chemical Sciences, Universiti Sains Malaysia is involved in the extraction and synthesis of the title compound and X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia is involved in the structure determination. All parties are involved in writing up the manuscript.

   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: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

5-Nitroisophthalic acid hydrate

Crystal data

C8H5NO6·H2O	F(000) = 944
Mr = 229.15	Dx = 1.728 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5535 reflections
a = 9.6139 (2) Å	θ = 2.3–37.7°
b = 10.5459 (2) Å	µ = 0.16 mm^−1
c = 17.3756 (3) Å	T = 100 K
V = 1761.66 (6) Å^3	Needle, colourless
Z = 8	0.56 × 0.10 × 0.09 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	4660 independent reflections
Radiation source: fine-focus sealed tube	3900 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 8.33 pixels mm^-1	θmax = 37.7°, θmin = 2.3°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→18
Tmin = 0.880, Tmax = 0.986	l = −29→29
63168 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0608P)^2 + 0.5268P] where P = (Fo^2 + 2Fc^2)/3
4660 reflections	(Δ/σ)max = 0.001
153 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.44 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	0.93320 (6)	−0.10724 (6)	0.75273 (4)	0.01585 (12)
O2	0.71912 (7)	−0.07803 (8)	0.78799 (4)	0.02422 (16)
O3	1.15779 (6)	0.21996 (6)	0.59401 (3)	0.01342 (11)
O4	1.03011 (6)	0.39021 (6)	0.56306 (4)	0.01558 (12)
H4B	1.1195	0.4280	0.5544	0.019*
O5	0.42088 (6)	0.18694 (6)	0.64015 (4)	0.01609 (12)
H5A	0.3403	0.2171	0.6262	0.019*
O6	0.50600 (6)	0.34083 (6)	0.56404 (4)	0.01548 (12)
N1	0.82111 (7)	−0.05200 (7)	0.74845 (4)	0.01279 (12)
C1	0.80825 (7)	0.05317 (7)	0.69356 (4)	0.01080 (12)
C2	0.92809 (7)	0.10723 (7)	0.66384 (4)	0.01101 (12)
H2A	1.0151	0.0730	0.6745	0.013*
C3	0.91446 (7)	0.21437 (7)	0.61749 (4)	0.01041 (12)
C4	0.78272 (7)	0.26234 (7)	0.59947 (4)	0.01087 (12)
H4A	0.7743	0.3346	0.5692	0.013*
C5	0.66397 (7)	0.20118 (7)	0.62716 (4)	0.01086 (12)
C6	0.67599 (7)	0.09610 (8)	0.67532 (4)	0.01151 (12)
H6A	0.5974	0.0558	0.6947	0.014*
C7	1.04540 (7)	0.27556 (7)	0.59011 (4)	0.01114 (12)
C8	0.52314 (7)	0.25059 (8)	0.60688 (4)	0.01181 (12)
O1W	0.76800 (6)	0.01661 (6)	0.47226 (4)	0.01509 (11)
H1A	0.7949 (19)	−0.0529 (19)	0.4523 (11)	0.041 (5)*
H1B	0.8351 (19)	0.0648 (18)	0.4629 (11)	0.038 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0117 (2)	0.0166 (3)	0.0192 (2)	0.0036 (2)	−0.00034 (18)	0.0038 (2)
O2	0.0125 (3)	0.0317 (4)	0.0285 (3)	0.0014 (3)	0.0054 (2)	0.0171 (3)
O3	0.0088 (2)	0.0133 (2)	0.0181 (2)	0.00025 (18)	0.00003 (17)	−0.00026 (19)
O4	0.0117 (2)	0.0121 (3)	0.0230 (3)	−0.00048 (19)	0.00191 (19)	0.0040 (2)
O5	0.0073 (2)	0.0177 (3)	0.0232 (3)	0.00018 (19)	−0.00015 (18)	0.0047 (2)
O6	0.0123 (2)	0.0161 (3)	0.0180 (2)	0.0029 (2)	−0.00033 (19)	0.0035 (2)
N1	0.0105 (2)	0.0138 (3)	0.0141 (2)	−0.0001 (2)	−0.00079 (19)	0.0027 (2)
C1	0.0091 (3)	0.0116 (3)	0.0118 (2)	−0.0001 (2)	−0.00005 (19)	0.0017 (2)
C2	0.0085 (2)	0.0119 (3)	0.0126 (3)	0.0002 (2)	−0.0004 (2)	0.0006 (2)
C3	0.0082 (2)	0.0110 (3)	0.0120 (2)	−0.0006 (2)	0.0002 (2)	0.0004 (2)
C4	0.0086 (2)	0.0118 (3)	0.0122 (3)	0.0005 (2)	−0.00004 (19)	0.0006 (2)
C5	0.0080 (2)	0.0123 (3)	0.0123 (3)	0.0008 (2)	−0.00029 (19)	0.0000 (2)
C6	0.0082 (2)	0.0132 (3)	0.0131 (3)	0.0001 (2)	0.0000 (2)	0.0014 (2)
C7	0.0096 (3)	0.0115 (3)	0.0123 (3)	−0.0006 (2)	0.0001 (2)	−0.0005 (2)
C8	0.0088 (3)	0.0134 (3)	0.0132 (3)	0.0007 (2)	−0.0007 (2)	−0.0007 (2)
O1W	0.0120 (2)	0.0121 (3)	0.0212 (3)	0.00134 (19)	0.00082 (19)	0.0013 (2)

Geometric parameters (Å, º)

O1—N1	1.2273 (9)	C2—C3	1.3937 (11)
O2—N1	1.2283 (9)	C2—H2A	0.9300
O3—C7	1.2313 (9)	C3—C4	1.3993 (10)
O4—C7	1.3056 (10)	C3—C7	1.4924 (10)
O4—H4B	0.9596	C4—C5	1.3967 (10)
O5—C8	1.3233 (10)	C4—H4A	0.9300
O5—H5A	0.8720	C5—C6	1.3935 (11)
O6—C8	1.2194 (10)	C5—C8	1.4929 (10)
N1—C1	1.4680 (10)	C6—H6A	0.9300
C1—C2	1.3854 (10)	O1W—H1A	0.85 (2)
C1—C6	1.3864 (10)	O1W—H1B	0.838 (19)
C7—O4—H4B	109.9	C5—C4—H4A	120.1
C8—O5—H5A	110.7	C3—C4—H4A	120.1
O1—N1—O2	124.12 (7)	C6—C5—C4	120.42 (7)
O1—N1—C1	118.16 (6)	C6—C5—C8	119.64 (7)
O2—N1—C1	117.71 (7)	C4—C5—C8	119.93 (7)
C2—C1—C6	122.90 (7)	C1—C6—C5	118.23 (7)
C2—C1—N1	118.88 (6)	C1—C6—H6A	120.9
C6—C1—N1	118.19 (6)	C5—C6—H6A	120.9
C1—C2—C3	118.09 (7)	O3—C7—O4	124.03 (7)
C1—C2—H2A	121.0	O3—C7—C3	121.12 (7)
C3—C2—H2A	121.0	O4—C7—C3	114.85 (6)
C2—C3—C4	120.49 (6)	O6—C8—O5	124.21 (7)
C2—C3—C7	117.09 (6)	O6—C8—C5	122.62 (7)
C4—C3—C7	122.40 (7)	O5—C8—C5	113.18 (7)
C5—C4—C3	119.73 (7)	H1A—O1W—H1B	102.1 (17)
O1—N1—C1—C2	−16.45 (11)	C2—C1—C6—C5	−2.40 (11)
O2—N1—C1—C2	162.61 (8)	N1—C1—C6—C5	175.89 (7)
O1—N1—C1—C6	165.19 (7)	C4—C5—C6—C1	−1.16 (11)
O2—N1—C1—C6	−15.75 (11)	C8—C5—C6—C1	−179.49 (7)
C6—C1—C2—C3	4.15 (11)	C2—C3—C7—O3	15.14 (11)
N1—C1—C2—C3	−174.12 (7)	C4—C3—C7—O3	−166.18 (7)
C1—C2—C3—C4	−2.37 (11)	C2—C3—C7—O4	−164.40 (7)
C1—C2—C3—C7	176.35 (7)	C4—C3—C7—O4	14.29 (10)
C2—C3—C4—C5	−1.01 (11)	C6—C5—C8—O6	−178.77 (8)
C7—C3—C4—C5	−179.66 (7)	C4—C5—C8—O6	2.90 (12)
C3—C4—C5—C6	2.82 (11)	C6—C5—C8—O5	1.43 (10)
C3—C4—C5—C8	−178.86 (7)	C4—C5—C8—O5	−176.91 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O3^i	0.85 (2)	1.99 (2)	2.839 (1)	176 (2)
O1W—H1B···O6^ii	0.84 (2)	1.98 (2)	2.810 (1)	173 (2)
O4—H4B···O1W^ii	0.96	1.61	2.564 (1)	172
O5—H5A···O3^iii	0.87	1.84	2.676 (1)	160
C4—H4A···O1W^iv	0.93	2.59	3.509 (1)	172
C6—H6A···O1^v	0.93	2.51	3.407 (1)	163

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