The cation of the title salt, C13H14N3+·C8H5O4-, adopts a conformation with one of the phenyl rings lying syn and the other anti with respect to the unsubstituted N atom. The anion features a strong intramolecular hydrogen bond, with the carboxyl groups twisted out of the ring plane. Intermolecular hydrogen-bonds link anions and cations, forming chains that run parallel to the c axis.
Supporting information
CCDC reference: 601254
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.038
- wR factor = 0.114
- Data-to-parameter ratio = 11.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C2 -C7 1.37 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C8 -C13 1.37 Ang.
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 30.10
From the CIF: _reflns_number_total 2999
Count of symmetry unique reflns 3004
Completeness (_total/calc) 99.83%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: SDP-Plus (Frenz, 1985); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
N,
N'-diphenylguanidinium phthalate
top
Crystal data top
C13H14N3+·C8H5O4− | F(000) = 396 |
Mr = 377.39 | Dx = 1.304 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 10.7714 (12) Å | θ = 8.2–12.0° |
b = 8.440 (2) Å | µ = 0.09 mm−1 |
c = 11.420 (3) Å | T = 293 K |
β = 112.172 (12)° | Prism, colourless |
V = 961.4 (4) Å3 | 0.34 × 0.27 × 0.15 mm |
Z = 2 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.031 |
Radiation source: fine-focus sealed tube | θmax = 30.1°, θmin = 3.1° |
Graphite monochromator | h = −15→15 |
profile data from ω–2θ scans | k = 0→11 |
5916 measured reflections | l = −16→16 |
2999 independent reflections | 3 standard reflections every 180 min |
1803 reflections with I > 2σ(I) | intensity decay: 3% |
Refinement top
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0647P)2] where P = (Fo2 + 2Fc2)/3 |
2999 reflections | (Δ/σ)max < 0.001 |
256 parameters | Δρmax = 0.16 e Å−3 |
1 restraint | Δρmin = −0.22 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.01506 (18) | 0.0035 (3) | 0.54850 (16) | 0.0669 (5) | |
H1 | −0.0607 | −0.0180 | 0.5538 | 0.080* | |
N2 | 0.10893 (19) | 0.0115 (3) | 0.76358 (17) | 0.0684 (6) | |
H2A | 0.1735 | 0.0367 | 0.8329 | 0.082* | |
H2B | 0.0389 | −0.0352 | 0.7658 | 0.082* | |
N3 | 0.22323 (17) | 0.1159 (3) | 0.64597 (16) | 0.0630 (5) | |
H3A | 0.2185 | 0.1431 | 0.5718 | 0.076* | |
C1 | 0.1173 (2) | 0.0442 (3) | 0.65443 (19) | 0.0574 (5) | |
C2 | 0.0239 (2) | −0.0064 (3) | 0.4280 (2) | 0.0622 (6) | |
C3 | 0.1140 (3) | −0.1055 (4) | 0.4077 (3) | 0.0873 (8) | |
H3 | 0.1738 | −0.1637 | 0.4743 | 0.105* | |
C4 | 0.1158 (4) | −0.1187 (5) | 0.2887 (3) | 0.1053 (11) | |
H4 | 0.1772 | −0.1866 | 0.2754 | 0.126* | |
C5 | 0.0316 (4) | −0.0364 (5) | 0.1915 (3) | 0.0970 (12) | |
H5 | 0.0336 | −0.0479 | 0.1112 | 0.116* | |
C6 | −0.0565 (3) | 0.0638 (6) | 0.2108 (3) | 0.1028 (12) | |
H6 | −0.1142 | 0.1226 | 0.1434 | 0.123* | |
C7 | −0.0628 (2) | 0.0809 (5) | 0.3294 (2) | 0.0795 (8) | |
H7 | −0.1241 | 0.1497 | 0.3419 | 0.095* | |
C8 | 0.3446 (2) | 0.1516 (3) | 0.75027 (18) | 0.0529 (5) | |
C9 | 0.3475 (2) | 0.2564 (3) | 0.8414 (2) | 0.0669 (6) | |
H9 | 0.2689 | 0.3053 | 0.8383 | 0.080* | |
C10 | 0.4681 (3) | 0.2902 (4) | 0.9391 (3) | 0.0823 (8) | |
H10 | 0.4702 | 0.3593 | 1.0032 | 0.099* | |
C11 | 0.5831 (3) | 0.2225 (4) | 0.9411 (3) | 0.0914 (9) | |
H11 | 0.6641 | 0.2468 | 1.0060 | 0.110* | |
C12 | 0.5807 (3) | 0.1193 (4) | 0.8488 (3) | 0.0919 (10) | |
H12 | 0.6601 | 0.0744 | 0.8503 | 0.110* | |
C13 | 0.4609 (2) | 0.0811 (4) | 0.7532 (3) | 0.0714 (6) | |
H13 | 0.4586 | 0.0083 | 0.6912 | 0.086* | |
O4 | 0.20405 (13) | 0.3301 (2) | 0.44567 (13) | 0.0607 (4) | |
O3 | 0.15213 (17) | 0.4138 (3) | 0.25175 (17) | 0.0775 (5) | |
O2 | 0.15715 (18) | 0.2810 (3) | 0.06339 (16) | 0.0867 (6) | |
H2 | 0.150 (3) | 0.345 (5) | 0.129 (3) | 0.104* | |
O1 | 0.25127 (19) | 0.0681 (3) | 0.02766 (15) | 0.0848 (6) | |
C14 | 0.34142 (18) | 0.2427 (3) | 0.33978 (17) | 0.0479 (4) | |
C15 | 0.44885 (19) | 0.2272 (3) | 0.45412 (19) | 0.0562 (5) | |
H15 | 0.4423 | 0.2701 | 0.5266 | 0.067* | |
C16 | 0.5650 (2) | 0.1502 (4) | 0.4635 (2) | 0.0662 (6) | |
H16 | 0.6357 | 0.1416 | 0.5414 | 0.079* | |
C17 | 0.5756 (2) | 0.0863 (4) | 0.3577 (2) | 0.0708 (6) | |
H17 | 0.6543 | 0.0360 | 0.3629 | 0.085* | |
C18 | 0.4697 (2) | 0.0968 (3) | 0.2439 (2) | 0.0641 (6) | |
H18 | 0.4767 | 0.0502 | 0.1728 | 0.077* | |
C19 | 0.35186 (19) | 0.1755 (3) | 0.23207 (18) | 0.0512 (5) | |
C20 | 0.22337 (19) | 0.3330 (3) | 0.34626 (19) | 0.0534 (5) | |
C21 | 0.2475 (2) | 0.1704 (4) | 0.0998 (2) | 0.0636 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0568 (9) | 0.0950 (15) | 0.0510 (9) | −0.0164 (11) | 0.0227 (8) | −0.0047 (11) |
N2 | 0.0634 (10) | 0.0959 (16) | 0.0484 (9) | −0.0227 (11) | 0.0239 (8) | −0.0031 (11) |
N3 | 0.0597 (10) | 0.0849 (15) | 0.0464 (8) | −0.0129 (10) | 0.0222 (7) | 0.0027 (10) |
C1 | 0.0575 (11) | 0.0688 (15) | 0.0488 (10) | −0.0054 (10) | 0.0234 (9) | −0.0007 (11) |
C2 | 0.0597 (11) | 0.0774 (15) | 0.0483 (10) | −0.0202 (12) | 0.0191 (9) | −0.0046 (12) |
C3 | 0.110 (2) | 0.087 (2) | 0.0742 (16) | 0.0139 (18) | 0.0445 (15) | 0.0062 (16) |
C4 | 0.136 (3) | 0.112 (3) | 0.088 (2) | −0.003 (2) | 0.065 (2) | −0.017 (2) |
C5 | 0.101 (2) | 0.141 (3) | 0.0548 (14) | −0.054 (2) | 0.0353 (15) | −0.027 (2) |
C6 | 0.0778 (17) | 0.163 (3) | 0.0501 (12) | −0.024 (2) | 0.0043 (12) | 0.010 (2) |
C7 | 0.0608 (12) | 0.111 (2) | 0.0577 (13) | −0.0097 (15) | 0.0118 (10) | 0.0013 (16) |
C8 | 0.0524 (10) | 0.0591 (12) | 0.0484 (9) | −0.0065 (10) | 0.0205 (8) | 0.0058 (10) |
C9 | 0.0707 (13) | 0.0683 (15) | 0.0671 (13) | −0.0056 (12) | 0.0323 (11) | −0.0008 (13) |
C10 | 0.102 (2) | 0.0753 (18) | 0.0650 (13) | −0.0248 (17) | 0.0257 (14) | −0.0075 (14) |
C11 | 0.0716 (16) | 0.088 (2) | 0.0889 (19) | −0.0148 (16) | 0.0005 (14) | 0.0157 (19) |
C12 | 0.0578 (13) | 0.086 (2) | 0.120 (2) | 0.0091 (14) | 0.0202 (15) | 0.013 (2) |
C13 | 0.0697 (14) | 0.0671 (15) | 0.0813 (16) | 0.0020 (13) | 0.0329 (12) | −0.0001 (15) |
O4 | 0.0511 (7) | 0.0807 (11) | 0.0545 (8) | 0.0014 (8) | 0.0246 (6) | −0.0007 (9) |
O3 | 0.0707 (9) | 0.0954 (12) | 0.0726 (10) | 0.0323 (10) | 0.0341 (9) | 0.0281 (11) |
O2 | 0.0799 (10) | 0.1203 (19) | 0.0518 (9) | 0.0268 (12) | 0.0155 (8) | 0.0191 (11) |
O1 | 0.0959 (12) | 0.1055 (15) | 0.0505 (9) | −0.0031 (12) | 0.0247 (8) | −0.0088 (11) |
C14 | 0.0458 (9) | 0.0521 (10) | 0.0465 (9) | −0.0018 (9) | 0.0181 (7) | 0.0057 (9) |
C15 | 0.0533 (10) | 0.0625 (13) | 0.0512 (10) | −0.0004 (10) | 0.0180 (8) | 0.0020 (11) |
C16 | 0.0493 (10) | 0.0792 (15) | 0.0608 (12) | 0.0056 (11) | 0.0101 (9) | 0.0080 (13) |
C17 | 0.0560 (11) | 0.0756 (15) | 0.0820 (15) | 0.0155 (12) | 0.0273 (11) | 0.0097 (15) |
C18 | 0.0670 (13) | 0.0666 (15) | 0.0651 (13) | 0.0077 (12) | 0.0323 (11) | 0.0006 (13) |
C19 | 0.0494 (9) | 0.0576 (12) | 0.0483 (9) | −0.0021 (9) | 0.0205 (8) | 0.0062 (10) |
C20 | 0.0448 (9) | 0.0615 (13) | 0.0553 (11) | −0.0004 (10) | 0.0203 (8) | 0.0036 (11) |
C21 | 0.0618 (11) | 0.0851 (17) | 0.0455 (10) | −0.0038 (13) | 0.0222 (9) | 0.0078 (13) |
Geometric parameters (Å, º) top
N1—C1 | 1.337 (3) | C10—C11 | 1.356 (4) |
N1—C2 | 1.417 (3) | C10—H10 | 0.9300 |
N1—H1 | 0.8600 | C11—C12 | 1.360 (5) |
N2—C1 | 1.313 (3) | C11—H11 | 0.9300 |
N2—H2A | 0.8600 | C12—C13 | 1.378 (4) |
N2—H2B | 0.8600 | C12—H12 | 0.9300 |
N3—C1 | 1.327 (3) | C13—H13 | 0.9300 |
N3—C8 | 1.429 (3) | O4—C20 | 1.229 (2) |
N3—H3A | 0.8600 | O3—C20 | 1.262 (3) |
C2—C3 | 1.365 (4) | O2—C21 | 1.299 (3) |
C2—C7 | 1.374 (4) | O2—H2 | 0.95 (4) |
C3—C4 | 1.372 (4) | O1—C21 | 1.205 (3) |
C3—H3 | 0.9300 | C14—C15 | 1.386 (3) |
C4—C5 | 1.333 (6) | C14—C19 | 1.397 (3) |
C4—H4 | 0.9300 | C14—C20 | 1.508 (3) |
C5—C6 | 1.351 (5) | C15—C16 | 1.377 (3) |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C6—C7 | 1.389 (4) | C16—C17 | 1.367 (3) |
C6—H6 | 0.9300 | C16—H16 | 0.9300 |
C7—H7 | 0.9300 | C17—C18 | 1.371 (3) |
C8—C9 | 1.357 (3) | C17—H17 | 0.9300 |
C8—C13 | 1.376 (3) | C18—C19 | 1.394 (3) |
C9—C10 | 1.386 (4) | C18—H18 | 0.9300 |
C9—H9 | 0.9300 | C19—C21 | 1.505 (3) |
| | | |
C1—N1—C2 | 123.99 (17) | C11—C10—H10 | 120.0 |
C1—N1—H1 | 118.0 | C9—C10—H10 | 120.0 |
C2—N1—H1 | 118.0 | C10—C11—C12 | 120.4 (3) |
C1—N2—H2A | 120.0 | C10—C11—H11 | 119.8 |
C1—N2—H2B | 120.0 | C12—C11—H11 | 119.8 |
H2A—N2—H2B | 120.0 | C11—C12—C13 | 120.2 (3) |
C1—N3—C8 | 125.21 (17) | C11—C12—H12 | 119.9 |
C1—N3—H3A | 117.4 | C13—C12—H12 | 119.9 |
C8—N3—H3A | 117.4 | C8—C13—C12 | 119.3 (3) |
N2—C1—N3 | 122.3 (2) | C8—C13—H13 | 120.3 |
N2—C1—N1 | 118.47 (18) | C12—C13—H13 | 120.3 |
N3—C1—N1 | 119.24 (18) | C21—O2—H2 | 116 (2) |
C3—C2—C7 | 119.7 (2) | C15—C14—C19 | 118.37 (18) |
C3—C2—N1 | 120.9 (2) | C15—C14—C20 | 114.91 (17) |
C7—C2—N1 | 119.3 (2) | C19—C14—C20 | 126.72 (17) |
C2—C3—C4 | 119.7 (3) | C16—C15—C14 | 121.9 (2) |
C2—C3—H3 | 120.2 | C16—C15—H15 | 119.0 |
C4—C3—H3 | 120.2 | C14—C15—H15 | 119.0 |
C5—C4—C3 | 121.6 (4) | C17—C16—C15 | 119.6 (2) |
C5—C4—H4 | 119.2 | C17—C16—H16 | 120.2 |
C3—C4—H4 | 119.2 | C15—C16—H16 | 120.2 |
C4—C5—C6 | 119.3 (3) | C16—C17—C18 | 119.7 (2) |
C4—C5—H5 | 120.3 | C16—C17—H17 | 120.1 |
C6—C5—H5 | 120.3 | C18—C17—H17 | 120.1 |
C5—C6—C7 | 121.3 (3) | C17—C18—C19 | 121.6 (2) |
C5—C6—H6 | 119.3 | C17—C18—H18 | 119.2 |
C7—C6—H6 | 119.3 | C19—C18—H18 | 119.2 |
C2—C7—C6 | 118.4 (3) | C18—C19—C14 | 118.79 (18) |
C2—C7—H7 | 120.8 | C18—C19—C21 | 113.05 (19) |
C6—C7—H7 | 120.8 | C14—C19—C21 | 128.12 (18) |
C9—C8—C13 | 120.4 (2) | O4—C20—O3 | 122.7 (2) |
C9—C8—N3 | 121.70 (19) | O4—C20—C14 | 118.35 (18) |
C13—C8—N3 | 117.8 (2) | O3—C20—C14 | 118.87 (17) |
C8—C9—C10 | 119.7 (2) | O1—C21—O2 | 120.7 (2) |
C8—C9—H9 | 120.2 | O1—C21—C19 | 120.1 (2) |
C10—C9—H9 | 120.2 | O2—C21—C19 | 119.1 (2) |
C11—C10—C9 | 120.0 (3) | | |
| | | |
C8—N3—C1—N2 | 6.7 (4) | N3—C8—C13—C12 | 176.6 (2) |
C8—N3—C1—N1 | −173.4 (2) | C11—C12—C13—C8 | 1.8 (4) |
C2—N1—C1—N2 | −163.0 (3) | C19—C14—C15—C16 | 1.0 (3) |
C2—N1—C1—N3 | 17.1 (4) | C20—C14—C15—C16 | −178.9 (2) |
C1—N1—C2—C3 | 58.5 (4) | C14—C15—C16—C17 | −0.2 (4) |
C1—N1—C2—C7 | −123.8 (3) | C15—C16—C17—C18 | −1.3 (4) |
C7—C2—C3—C4 | −1.0 (5) | C16—C17—C18—C19 | 2.0 (4) |
N1—C2—C3—C4 | 176.7 (3) | C17—C18—C19—C14 | −1.1 (4) |
C2—C3—C4—C5 | 0.2 (6) | C17—C18—C19—C21 | −178.9 (3) |
C3—C4—C5—C6 | 0.8 (6) | C15—C14—C19—C18 | −0.4 (3) |
C4—C5—C6—C7 | −1.1 (6) | C20—C14—C19—C18 | 179.5 (2) |
C3—C2—C7—C6 | 0.7 (4) | C15—C14—C19—C21 | 177.0 (2) |
N1—C2—C7—C6 | −177.0 (3) | C20—C14—C19—C21 | −3.0 (4) |
C5—C6—C7—C2 | 0.4 (5) | C15—C14—C20—O4 | −28.7 (3) |
C1—N3—C8—C9 | −65.4 (3) | C19—C14—C20—O4 | 151.3 (2) |
C1—N3—C8—C13 | 117.3 (3) | C15—C14—C20—O3 | 148.2 (2) |
C13—C8—C9—C10 | −1.2 (4) | C19—C14—C20—O3 | −31.7 (3) |
N3—C8—C9—C10 | −178.4 (2) | C18—C19—C21—O1 | 22.3 (3) |
C8—C9—C10—C11 | 2.1 (4) | C14—C19—C21—O1 | −155.3 (2) |
C9—C10—C11—C12 | −1.1 (5) | C18—C19—C21—O2 | −155.0 (2) |
C10—C11—C12—C13 | −0.9 (5) | C14—C19—C21—O2 | 27.5 (4) |
C9—C8—C13—C12 | −0.7 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O4i | 0.86 | 2.01 | 2.799 (2) | 152 |
N2—H2A···O1ii | 0.86 | 2.08 | 2.861 (3) | 151 |
N3—H3A···O4 | 0.86 | 2.10 | 2.861 (3) | 147 |
O2—H2···O3 | 0.95 (4) | 1.51 (4) | 2.444 (3) | 167 (4) |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) x, y, z+1. |