Glycinium 3-nitro­phthalate

In the title compound, C₂H₆NO₂⁺·C₈H₄NO₆⁻, the cations and anions are self-assembled into chains by N—H...O and O—H...O hydrogen bonds, respectively. The two chains are held together by further N—H...O hydrogen bonds, resulting in a two-dimensional sheet.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.131
• Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.33
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

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

   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1994); 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.

Glycinium 3-nitrophthalate

Crystal data

C2H6NO2^+·C8H4NO6^−	F(000) = 592
Mr = 286.20	Dx = 1.616 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2221 reflections
a = 12.965 (3) Å	θ = 2.5–25.0°
b = 10.966 (2) Å	µ = 0.14 mm^−1
c = 8.6833 (17) Å	T = 298 K
β = 107.61 (3)°	Block, colourless
V = 1176.7 (4) Å^3	0.25 × 0.18 × 0.12 mm
Z = 4

Data collection

Siemens SMART CCD 1000 area-detector diffractometer	1735 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 25.0°, θmin = 2.5°
ω scans	h = −15→14
2221 measured reflections	k = −13→0
2072 independent reflections	l = 0→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	All H-atom parameters refined
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0739P)^2 + 0.2988P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2072 reflections	Δρmax = 0.44 e Å^−3
222 parameters	Δρmin = −0.29 e Å^−3
5 restraints	Extinction correction: SHELXTL (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.055 (6)

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
O3	0.29846 (13)	0.74895 (15)	0.7915 (2)	0.0491 (5)
O4	0.15453 (11)	0.66768 (14)	0.61099 (18)	0.0406 (4)
O5	0.16894 (11)	0.57529 (12)	0.29973 (16)	0.0342 (4)
O6	0.11624 (11)	0.41404 (13)	0.41336 (17)	0.0373 (4)
O7	0.37504 (19)	0.20317 (17)	0.4319 (3)	0.0760 (7)
O8	0.28117 (15)	0.33386 (17)	0.2649 (2)	0.0601 (5)
N2	0.34027 (15)	0.30613 (17)	0.3975 (2)	0.0417 (5)
C3	0.32670 (16)	0.57116 (16)	0.6604 (2)	0.0299 (5)
C4	0.29398 (15)	0.48759 (17)	0.5314 (2)	0.0282 (4)
C5	0.36946 (16)	0.39861 (18)	0.5261 (2)	0.0331 (5)
C6	0.47164 (18)	0.3917 (2)	0.6331 (3)	0.0404 (5)
C7	0.50302 (18)	0.4755 (2)	0.7562 (3)	0.0428 (5)
C8	0.43001 (18)	0.5633 (2)	0.7701 (3)	0.0392 (5)
C9	0.25008 (16)	0.66649 (17)	0.6827 (2)	0.0312 (5)
C10	0.18297 (15)	0.49108 (17)	0.4060 (2)	0.0276 (4)
O1	0.16865 (16)	−0.02697 (17)	0.4917 (2)	0.0563 (5)
O2	0.05918 (14)	0.12486 (14)	0.50862 (18)	0.0446 (4)
N1	0.02564 (18)	0.19864 (19)	0.2079 (2)	0.0456 (5)
C1	0.1004 (2)	0.0964 (2)	0.2636 (3)	0.0415 (5)
C2	0.10678 (17)	0.06733 (18)	0.4345 (2)	0.0352 (5)
H7A	0.576 (2)	0.473 (3)	0.831 (3)	0.057 (7)*
H8A	0.4499 (19)	0.619 (2)	0.852 (3)	0.048 (7)*
H6A	0.516 (2)	0.334 (3)	0.622 (3)	0.058 (8)*
H1B	0.170 (3)	0.111 (3)	0.251 (4)	0.064 (8)*
H5	0.250 (2)	0.803 (2)	0.787 (4)	0.076 (10)*
H1A	0.080 (2)	0.024 (3)	0.198 (4)	0.061 (8)*
H3	−0.0393 (17)	0.179 (3)	0.206 (4)	0.068 (9)*
H2	0.049 (2)	0.263 (2)	0.266 (3)	0.056 (8)*
H1	0.014 (3)	0.224 (3)	0.111 (3)	0.090 (11)*
H4	0.167 (3)	−0.041 (4)	0.589 (3)	0.111 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0400 (9)	0.0389 (9)	0.0586 (11)	0.0022 (7)	0.0003 (8)	−0.0240 (8)
O4	0.0358 (8)	0.0371 (9)	0.0417 (8)	0.0031 (6)	0.0008 (6)	−0.0099 (7)
O5	0.0434 (8)	0.0293 (8)	0.0256 (7)	0.0003 (6)	0.0042 (6)	0.0038 (6)
O6	0.0408 (8)	0.0352 (8)	0.0322 (8)	−0.0108 (6)	0.0055 (6)	−0.0006 (6)
O7	0.0938 (15)	0.0433 (11)	0.0722 (13)	0.0280 (10)	−0.0030 (11)	−0.0173 (10)
O8	0.0740 (12)	0.0583 (11)	0.0381 (10)	0.0141 (9)	0.0020 (9)	−0.0120 (8)
N2	0.0446 (10)	0.0365 (10)	0.0425 (11)	0.0100 (8)	0.0107 (9)	−0.0061 (8)
C3	0.0332 (10)	0.0231 (9)	0.0295 (10)	−0.0015 (8)	0.0034 (8)	0.0003 (8)
C4	0.0331 (10)	0.0238 (9)	0.0265 (10)	−0.0004 (7)	0.0072 (8)	0.0035 (7)
C5	0.0392 (11)	0.0258 (10)	0.0339 (11)	0.0018 (8)	0.0105 (9)	0.0010 (8)
C6	0.0395 (12)	0.0338 (11)	0.0460 (13)	0.0075 (10)	0.0100 (10)	0.0042 (10)
C7	0.0327 (11)	0.0413 (12)	0.0456 (12)	0.0001 (9)	−0.0013 (9)	0.0061 (10)
C8	0.0411 (12)	0.0310 (11)	0.0374 (12)	−0.0022 (9)	−0.0002 (9)	−0.0030 (9)
C9	0.0370 (11)	0.0254 (10)	0.0278 (10)	−0.0030 (8)	0.0046 (8)	−0.0014 (8)
C10	0.0359 (10)	0.0231 (9)	0.0230 (9)	−0.0010 (8)	0.0076 (8)	−0.0027 (7)
O1	0.0774 (12)	0.0523 (11)	0.0423 (10)	0.0246 (9)	0.0230 (9)	0.0096 (8)
O2	0.0686 (11)	0.0383 (9)	0.0286 (8)	0.0080 (7)	0.0174 (7)	−0.0016 (6)
N1	0.0561 (13)	0.0439 (12)	0.0294 (10)	−0.0160 (10)	0.0019 (9)	0.0080 (9)
C1	0.0553 (14)	0.0401 (12)	0.0307 (11)	−0.0086 (10)	0.0154 (10)	−0.0022 (9)
C2	0.0467 (12)	0.0302 (11)	0.0272 (10)	−0.0035 (9)	0.0089 (9)	−0.0017 (8)

Geometric parameters (Å, º)

C9—O3	1.321 (2)	C6—H6A	0.88 (3)
O3—H5	0.858 (18)	C7—C8	1.381 (3)
C9—O4	1.206 (2)	C7—H7A	0.97 (3)
C10—O5	1.279 (2)	C8—H8A	0.91 (3)
C10—O6	1.225 (2)	C2—O1	1.311 (3)
N2—O7	1.219 (3)	O1—H4	0.863 (19)
N2—O8	1.213 (3)	C2—O2	1.197 (3)
N2—C5	1.471 (3)	N1—C1	1.465 (3)
C3—C8	1.392 (3)	N1—H3	0.862 (18)
C3—C4	1.410 (3)	N1—H2	0.864 (18)
C3—C9	1.494 (3)	N1—H1	0.853 (19)
C4—C5	1.393 (3)	C1—C2	1.496 (3)
C4—C10	1.520 (3)	C1—H1B	0.96 (3)
C5—C6	1.371 (3)	C1—H1A	0.96 (3)
C6—C7	1.374 (3)
C9—O3—H5	105 (2)	O4—C9—O3	123.56 (18)
O8—N2—O7	123.1 (2)	O4—C9—C3	124.05 (17)
O8—N2—C5	119.41 (18)	O3—C9—C3	112.39 (17)
O7—N2—C5	117.49 (19)	O6—C10—O5	125.96 (18)
C8—C3—C4	119.96 (19)	O6—C10—C4	118.42 (16)
C8—C3—C9	119.66 (18)	O5—C10—C4	115.61 (16)
C4—C3—C9	120.36 (17)	C2—O1—H4	109 (3)
C5—C4—C3	115.87 (18)	C1—N1—H3	111 (2)
C5—C4—C10	121.10 (17)	C1—N1—H2	110.5 (19)
C3—C4—C10	123.02 (17)	H3—N1—H2	113 (3)
C6—C5—C4	124.10 (19)	C1—N1—H1	118 (2)
C6—C5—N2	116.79 (18)	H3—N1—H1	100 (3)
C4—C5—N2	119.10 (18)	H2—N1—H1	103 (3)
C5—C6—C7	119.2 (2)	N1—C1—C2	108.83 (19)
C5—C6—H6A	119.7 (19)	N1—C1—H1B	112.7 (18)
C7—C6—H6A	121.1 (19)	C2—C1—H1B	112.3 (18)
C6—C7—C8	119.0 (2)	N1—C1—H1A	113.4 (17)
C6—C7—H7A	120.1 (16)	C2—C1—H1A	109.7 (17)
C8—C7—H7A	120.9 (16)	H1B—C1—H1A	100 (2)
C7—C8—C3	121.8 (2)	O2—C2—O1	124.6 (2)
C7—C8—H8A	119.6 (16)	O2—C2—C1	122.6 (2)
C3—C8—H8A	118.6 (16)	O1—C2—C1	112.84 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···O6	0.86 (2)	2.12 (2)	2.979 (3)	176 (3)
N1—H3···O5^i	0.86 (2)	2.02 (2)	2.845 (3)	160 (3)
N1—H1···O2^ii	0.85 (2)	2.05 (3)	2.717 (2)	135 (3)
O1—H4···O5^iii	0.86 (2)	1.86 (2)	2.725 (2)	178 (4)
O3—H5···O5^iv	0.86 (2)	1.72 (2)	2.571 (2)	170 (3)

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