D-Phenyl­glycinium nitrate

In the title compound, C₈H₁₀NO₂⁺·NO₃⁻, there are two crystallographically independent cations and two anions, the pairs being related by a pseudo-inversion centre at approx­imately (0, , ). The phenyl­glycinium cations and nitrate anions are linked to each other through strong N—H...O and O—H...O hydrogen bonds, forming a three-dimensional complex network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.056
• wR factor = 0.138
• Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given .          ?
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       9.29 Ratio

Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.44 Ratio

Alert level C
PLAT024_ALERT_4_C Merging of Friedel Data Preferred for Z<=Si ....          !
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.72 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.08 Ratio
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        N2A
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.04
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N1B    -   H120     =       1.01 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O5A    ..  C2A      =       2.93 Ang.

Alert level G
REFLT03_ALERT_4_G  ALERT: MoKa measured Friedel data cannot be used to
                   determine absolute structure in a light-atom
                   study EXCEPT under VERY special conditions.
                   It is preferred that Friedel data is merged in such cases.
           From the CIF: _diffrn_reflns_theta_max           26.30
           From the CIF: _reflns_number_total               3752
           Count of symmetry unique reflns         2200
           Completeness (_total/calc)            170.55%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1552
           Fraction of Friedel pairs measured     0.705
           Are heavy atom types Z>Si present           no

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

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

---

Computing details

Data collection: KappaCCD Reference Manual (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 1990); software used to prepare material for publication: WinGX (Farrugia, 1999).

D-Phenylglycinium nitrate

Crystal data

C8H10NO2^+·NO3^−	F(000) = 448
Mr = 214.18	Dx = 1.445 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3980 reflections
a = 10.4320 (3) Å	θ = 2.0–26.3°
b = 5.6450 (2) Å	µ = 0.12 mm^−1
c = 16.7830 (2) Å	T = 293 K
β = 94.943 (3)°	Prism, colourless
V = 984.65 (5) Å^3	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	2831 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
Graphite monochromator	θmax = 26.3°, θmin = 2.0°
φ scans	h = −12→12
7185 measured reflections	k = −6→6
3752 independent reflections	l = −20→20

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0724P)^2] where P = (Fo^2 + 2Fc^2)/3
3752 reflections	(Δ/σ)max = 0.004
328 parameters	Δρmax = 0.25 e Å^−3
1 restraint	Δρmin = −0.27 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
C1A	0.1469 (4)	0.4257 (8)	0.4835 (2)	0.0249 (9)
C1B	0.1415 (4)	0.7185 (7)	−0.0142 (2)	0.0263 (10)
C2A	0.1714 (4)	0.2955 (8)	0.5622 (2)	0.0245 (9)
H2	0.1462	0.1248	0.5531	0.014 (9)*
C2B	0.1869 (3)	0.5997 (7)	0.0639 (2)	0.0213 (9)
H22	0.1759	0.4347	0.0539	0.032 (12)*
C3A	0.3143 (4)	0.2959 (8)	0.5912 (3)	0.0285 (10)
C3B	0.3260 (4)	0.6582 (8)	0.0902 (2)	0.0251 (9)
C4A	0.3722 (5)	0.4762 (9)	0.6352 (3)	0.0482 (14)
H4	0.3345	0.6174	0.6443	0.048 (14)*
C4B	0.3981 (4)	0.4990 (10)	0.1380 (3)	0.0455 (13)
H44	0.3606	0.3541	0.1508	0.032 (12)*
C5A	0.5039 (5)	0.4687 (13)	0.6568 (4)	0.0649 (18)
H5	0.5389	0.6080	0.6802	0.061 (17)*
C5B	0.5256 (5)	0.5495 (12)	0.1627 (4)	0.0654 (19)
H55	0.5668	0.4342	0.1966	0.069 (18)*
C6A	0.5762 (5)	0.2815 (14)	0.6332 (4)	0.0659 (17)
H6	0.6636	0.2574	0.6490	0.13 (3)*
C6B	0.5817 (5)	0.7518 (12)	0.1387 (4)	0.0565 (15)
H66	0.6694	0.7846	0.1531	0.070 (18)*
C7A	0.5185 (5)	0.1051 (12)	0.5888 (4)	0.0664 (18)
H7	0.5581	−0.0329	0.5690	0.059 (17)*
C7B	0.5107 (5)	0.9092 (12)	0.0901 (4)	0.0589 (16)
H77	0.5451	1.0546	0.0721	0.071 (19)*
C8A	0.3882 (5)	0.1093 (10)	0.5671 (3)	0.0500 (14)
H8	0.3462	−0.0228	0.5437	0.049 (15)*
C8B	0.3828 (4)	0.8655 (9)	0.0671 (3)	0.0432 (13)
H88	0.3309	0.9665	0.0323	0.046 (14)*
N1A	0.0896 (3)	0.3989 (7)	0.6226 (2)	0.0291 (9)
H10	−0.0042	0.3649	0.6087	0.050 (15)*
H11	0.1036	0.5605	0.6336	0.053 (17)*
H12	0.1105	0.3164	0.6637	0.07 (2)*
N1B	0.0990 (3)	0.6691 (6)	0.12531 (19)	0.0245 (8)
H100	0.0989	0.8453	0.1335	0.018 (11)*
H110	0.0160	0.6233	0.1050	0.034 (12)*
H120	0.1270	0.5971	0.1791	0.08 (2)*
N2A	0.8659 (3)	0.3989 (6)	0.2635 (2)	0.0284 (8)
N2B	0.1387 (3)	0.1677 (6)	0.2384 (2)	0.0277 (8)
O1A	0.1060 (3)	0.6267 (6)	0.47733 (18)	0.0381 (8)
O1B	0.0802 (3)	0.9000 (6)	−0.01840 (17)	0.0342 (8)
O2A	0.1759 (3)	0.2876 (7)	0.42532 (18)	0.0449 (9)
H	0.1607	0.3380	0.3724	0.039 (14)*
O2B	0.1820 (3)	0.6028 (6)	−0.07435 (19)	0.0474 (10)
H'	0.1647	0.6729	−0.1198	0.055 (16)*
O3A	0.8728 (3)	0.5946 (6)	0.2296 (2)	0.0452 (9)
O3B	0.1315 (3)	−0.0109 (6)	0.2801 (2)	0.0428 (9)
O4A	0.8454 (4)	0.2135 (6)	0.22480 (19)	0.0492 (10)
O4B	0.1270 (4)	0.1552 (6)	0.16386 (17)	0.0424 (9)
O5A	0.8820 (3)	0.3867 (6)	0.33787 (19)	0.0438 (9)
O5B	0.1552 (3)	0.3716 (5)	0.2692 (2)	0.0368 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.020 (2)	0.032 (2)	0.023 (2)	−0.0022 (17)	0.0011 (17)	0.0021 (17)
C1B	0.023 (2)	0.032 (2)	0.024 (2)	0.0016 (17)	0.0000 (17)	0.0002 (17)
C2A	0.023 (2)	0.030 (2)	0.020 (2)	−0.0011 (17)	0.0021 (17)	−0.0019 (17)
C2B	0.021 (2)	0.024 (2)	0.018 (2)	0.0022 (16)	0.0007 (16)	0.0021 (15)
C3A	0.032 (2)	0.032 (2)	0.021 (2)	0.0014 (18)	0.0028 (19)	0.0072 (18)
C3B	0.022 (2)	0.034 (2)	0.019 (2)	0.0014 (17)	0.0002 (16)	0.0013 (18)
C4A	0.039 (3)	0.044 (3)	0.060 (4)	0.006 (2)	−0.008 (2)	−0.019 (3)
C4B	0.030 (3)	0.052 (3)	0.052 (3)	−0.001 (2)	−0.005 (2)	0.023 (3)
C5A	0.047 (4)	0.074 (5)	0.071 (5)	−0.011 (3)	−0.013 (3)	−0.013 (4)
C5B	0.032 (3)	0.082 (4)	0.078 (5)	−0.002 (3)	−0.020 (3)	0.039 (4)
C6A	0.032 (3)	0.084 (4)	0.080 (5)	0.005 (3)	−0.006 (3)	0.005 (4)
C6B	0.022 (3)	0.077 (4)	0.070 (4)	−0.008 (3)	−0.003 (2)	0.010 (4)
C7A	0.035 (3)	0.069 (4)	0.096 (5)	0.016 (3)	0.010 (3)	−0.009 (4)
C7B	0.036 (3)	0.055 (3)	0.085 (5)	−0.017 (3)	0.002 (3)	0.019 (3)
C8A	0.044 (3)	0.043 (3)	0.064 (4)	0.007 (2)	0.005 (3)	−0.007 (3)
C8B	0.032 (3)	0.041 (3)	0.056 (4)	−0.003 (2)	−0.002 (2)	0.016 (2)
N1A	0.031 (2)	0.031 (2)	0.026 (2)	−0.0006 (16)	0.0073 (16)	0.0015 (18)
N1B	0.029 (2)	0.0260 (17)	0.0181 (19)	−0.0045 (15)	0.0009 (14)	0.0030 (15)
N2A	0.0297 (19)	0.033 (2)	0.023 (2)	0.0031 (16)	0.0021 (16)	−0.0003 (17)
N2B	0.035 (2)	0.0240 (17)	0.024 (2)	0.0007 (15)	0.0025 (15)	0.0012 (16)
O1A	0.0435 (19)	0.0393 (19)	0.0308 (19)	0.0074 (16)	−0.0007 (14)	0.0059 (15)
O1B	0.0377 (18)	0.0392 (18)	0.0248 (17)	0.0136 (14)	−0.0024 (13)	0.0070 (13)
O2A	0.066 (2)	0.051 (2)	0.0175 (18)	0.0122 (18)	0.0036 (15)	−0.0011 (15)
O2B	0.065 (2)	0.057 (2)	0.0213 (18)	0.0336 (19)	0.0078 (15)	0.0072 (15)
O3A	0.045 (2)	0.041 (2)	0.050 (2)	0.0010 (16)	0.0034 (16)	0.0170 (17)
O3B	0.068 (2)	0.0303 (19)	0.0308 (19)	0.0023 (15)	0.0082 (16)	0.0128 (14)
O4A	0.083 (3)	0.042 (2)	0.0228 (19)	−0.0085 (18)	0.0029 (17)	−0.0089 (15)
O4B	0.078 (3)	0.0325 (17)	0.0174 (17)	−0.0082 (17)	0.0063 (15)	−0.0003 (15)
O5A	0.076 (3)	0.0323 (18)	0.0239 (19)	−0.0014 (16)	0.0069 (16)	−0.0073 (15)
O5B	0.053 (2)	0.0312 (18)	0.0262 (19)	−0.0035 (15)	0.0041 (15)	−0.0047 (14)

Geometric parameters (Å, º)

C1A—O1A	1.213 (5)	C6A—C7A	1.354 (9)
C1A—O2A	1.306 (5)	C6A—H6	0.9372
C1A—C2A	1.514 (6)	C6B—C7B	1.378 (8)
C1B—O1B	1.207 (5)	C6B—H66	0.9440
C1B—O2B	1.303 (5)	C7A—C8A	1.377 (7)
C1B—C2B	1.512 (5)	C7A—H7	0.9547
C2A—N1A	1.499 (5)	C7B—C8B	1.379 (6)
C2A—C3A	1.528 (5)	C7B—H77	0.9553
C2A—H2	1.0072	C8A—H8	0.9344
C2B—N1B	1.489 (5)	C8B—H88	0.9511
C2B—C3B	1.516 (5)	N1A—H10	1.0044
C2B—H22	0.9512	N1A—H11	0.9397
C3A—C4A	1.367 (6)	N1A—H12	0.8441
C3A—C8A	1.385 (7)	N1B—H100	1.0040
C3B—C8B	1.382 (6)	N1B—H110	0.9396
C3B—C4B	1.384 (6)	N1B—H120	1.0105
C4A—C5A	1.391 (7)	N2A—O4A	1.241 (5)
C4A—H4	0.9076	N2A—O5A	1.246 (5)
C4B—C5B	1.388 (7)	N2A—O3A	1.248 (5)
C4B—H44	0.9392	N2B—O3B	1.234 (5)
C5A—C6A	1.376 (9)	N2B—O4B	1.248 (4)
C5A—H5	0.9386	N2B—O5B	1.268 (5)
C5B—C6B	1.361 (9)	O2A—H	0.9336
C5B—H55	0.9428	O2B—H'	0.8650
O1A—C1A—O2A	126.6 (4)	C7A—C6A—H6	115.1
O1A—C1A—C2A	124.1 (4)	C5A—C6A—H6	125.1
O2A—C1A—C2A	109.3 (4)	C5B—C6B—C7B	119.5 (5)
O1B—C1B—O2B	125.8 (4)	C5B—C6B—H66	121.4
O1B—C1B—C2B	123.6 (4)	C7B—C6B—H66	119.1
O2B—C1B—C2B	110.6 (3)	C6A—C7A—C8A	121.0 (5)
N1A—C2A—C1A	109.7 (3)	C6A—C7A—H7	127.4
N1A—C2A—C3A	112.4 (3)	C8A—C7A—H7	111.6
C1A—C2A—C3A	111.4 (3)	C6B—C7B—C8B	120.6 (5)
N1A—C2A—H2	108.7	C6B—C7B—H77	122.9
C1A—C2A—H2	108.0	C8B—C7B—H77	116.5
C3A—C2A—H2	106.5	C7A—C8A—C3A	119.8 (5)
N1B—C2B—C1B	108.5 (3)	C7A—C8A—H8	120.9
N1B—C2B—C3B	111.9 (3)	C3A—C8A—H8	118.5
C1B—C2B—C3B	112.1 (3)	C7B—C8B—C3B	120.1 (5)
N1B—C2B—H22	107.9	C7B—C8B—H88	123.4
C1B—C2B—H22	104.9	C3B—C8B—H88	116.4
C3B—C2B—H22	111.3	C2A—N1A—H10	111.6
C4A—C3A—C8A	119.5 (4)	C2A—N1A—H11	114.9
C4A—C3A—C2A	123.1 (4)	H10—N1A—H11	111.3
C8A—C3A—C2A	117.2 (4)	C2A—N1A—H12	102.4
C8B—C3B—C4B	119.2 (4)	H10—N1A—H12	105.2
C8B—C3B—C2B	121.7 (4)	H11—N1A—H12	110.6
C4B—C3B—C2B	119.1 (4)	C2B—N1B—H100	111.3
C3A—C4A—C5A	119.9 (5)	C2B—N1B—H110	106.2
C3A—C4A—H4	124.5	H100—N1B—H110	108.1
C5A—C4A—H4	114.6	C2B—N1B—H120	111.4
C3B—C4B—C5B	119.9 (5)	H100—N1B—H120	106.3
C3B—C4B—H44	118.8	H110—N1B—H120	113.6
C5B—C4B—H44	121.2	O4A—N2A—O5A	118.7 (4)
C6A—C5A—C4A	120.2 (6)	O4A—N2A—O3A	121.5 (4)
C6A—C5A—H5	124.1	O5A—N2A—O3A	119.8 (4)
C4A—C5A—H5	115.0	O3B—N2B—O4B	121.2 (3)
C6B—C5B—C4B	120.6 (5)	O3B—N2B—O5B	121.5 (4)
C6B—C5B—H55	124.9	O4B—N2B—O5B	117.3 (3)
C4B—C5B—H55	114.4	C1A—O2A—H	119.9
C7A—C6A—C5A	119.6 (5)	C1B—O2B—H'	113.5
O1A—C1A—C2A—N1A	24.1 (5)	C8A—C3A—C4A—C5A	−1.3 (7)
O2A—C1A—C2A—N1A	−155.8 (3)	C2A—C3A—C4A—C5A	−177.5 (4)
O1A—C1A—C2A—C3A	−101.2 (4)	C8B—C3B—C4B—C5B	0.6 (7)
O2A—C1A—C2A—C3A	78.9 (4)	C2B—C3B—C4B—C5B	179.9 (4)
O1B—C1B—C2B—N1B	25.4 (4)	C3A—C4A—C5A—C6A	1.0 (8)
O2B—C1B—C2B—N1B	−156.6 (3)	C3B—C4B—C5B—C6B	−1.7 (8)
O1B—C1B—C2B—C3B	−98.6 (4)	C4A—C5A—C6A—C7A	0.1 (9)
O2B—C1B—C2B—C3B	79.4 (4)	C4B—C5B—C6B—C7B	1.1 (9)
N1A—C2A—C3A—C4A	−37.6 (5)	C5A—C6A—C7A—C8A	−0.8 (9)
C1A—C2A—C3A—C4A	86.0 (4)	C5B—C6B—C7B—C8B	0.6 (9)
N1A—C2A—C3A—C8A	146.1 (4)	C6A—C7A—C8A—C3A	0.4 (8)
C1A—C2A—C3A—C8A	−90.3 (4)	C4A—C3A—C8A—C7A	0.7 (7)
N1B—C2B—C3B—C8B	−95.9 (4)	C2A—C3A—C8A—C7A	177.1 (4)
C1B—C2B—C3B—C8B	26.1 (5)	C4B—C3B—C8B—C7B	1.1 (7)
N1B—C2B—C3B—C4B	84.8 (4)	C2B—C3B—C8B—C7B	−178.2 (4)
C1B—C2B—C3B—C4B	−153.2 (4)	C6B—C7B—C8B—C3B	−1.7 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H···O3B	0.93	2.51	2.966 (5)	110
O2A—H···O5B	0.93	1.74	2.653 (5)	166
O2B—H′···O4A^i	0.87	1.77	2.593 (5)	158
N1A—H10···O1A^ii	1.01	2.18	2.958 (5)	133
N1A—H10···O3B^iii	1.01	2.48	2.982 (5)	110
N1A—H11···O4A^iv	0.94	2.54	3.142 (5)	122
N1A—H11···O5A^iv	0.94	1.91	2.842 (5)	174
N1A—H12···O3A^v	0.85	2.18	3.015 (5)	170
N1A—H12···O5A^v	0.85	2.43	2.976 (5)	123
N1B—H100···O3B^vi	1.00	2.59	3.158 (5)	116
N1B—H100···O4B^vi	1.00	1.84	2.829 (5)	168
N1B—H110···O1B^vii	0.94	2.11	2.906 (4)	142
N1B—H120···O4B	1.01	2.51	2.981 (5)	108
N1B—H120···O5B	1.01	1.98	2.958 (5)	163

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