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In the title compound, 2C
7H
7NO
2·C
6H
5NO
2, the 4-aminobenzoic acid and the nicotinic acid molecules are approximately planar. The crystal structure is stabilized by an extensive network of N—H
O, O—H
O and O—H
N hydrogen bonds.
Supporting information
CCDC reference: 629523
Key indicators
- Single-crystal X-ray study
- T = 303 K
- Mean (C-C) = 0.011 Å
- R factor = 0.075
- wR factor = 0.234
- Data-to-parameter ratio = 6.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 96 PerFi
PLAT113_ALERT_2_B ADDSYM Suggests Possible Pseudo/New Spacegroup . C2/c
PLAT230_ALERT_2_B Hirshfeld Test Diff for O6 - C20 .. 7.11 su
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.16
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 24.99
From the CIF: _reflns_number_total 1614
Count of symmetry unique reflns 1668
Completeness (_total/calc) 96.76%
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
4 ALERT level B = Potentially serious problem
2 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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
4-Aminobenzoic acid–nicotinic acid (2/1)
top
Crystal data top
2C7H7NO2·C6H5NO2 | F(000) = 832 |
Mr = 397.38 | Dx = 1.395 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 25 reflections |
a = 10.1803 (4) Å | θ = 2–25° |
b = 13.8050 (7) Å | µ = 0.11 mm−1 |
c = 13.6530 (8) Å | T = 303 K |
β = 99.680 (4)° | Block, yellow |
V = 1891.46 (16) Å3 | 0.4 × 0.25 × 0.2 mm |
Z = 4 | |
Data collection top
Nonius MACH3 sealed-tube diffractometer | Rint = 0.043 |
ω–2θ scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: ψ scan (North et al., 1968) | h = −1→12 |
Tmin = 0.969, Tmax = 0.979 | k = −16→16 |
3471 measured reflections | l = −16→16 |
1614 independent reflections | 3 standard reflections every 60 min |
1281 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | 2 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.075 | w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.234 | (Δ/σ)max = 0.006 |
S = 1.05 | Δρmax = 0.33 e Å−3 |
1614 reflections | Δρmin = −0.30 e Å−3 |
262 parameters | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N3 | 0.0741 (5) | 0.0502 (5) | 0.5822 (4) | 0.0359 (14) | |
C15 | 0.0776 (7) | 0.0052 (4) | 0.4932 (5) | 0.0316 (13) | |
H15 | 0.0772 | −0.0621 | 0.4902 | 0.038* | |
C16 | 0.0817 (5) | 0.0572 (5) | 0.4095 (5) | 0.0308 (13) | |
C18 | 0.0796 (10) | 0.2018 (4) | 0.5030 (6) | 0.0461 (13) | |
H18 | 0.0829 | 0.269 | 0.5066 | 0.055* | |
O6 | 0.0641 (5) | 0.0605 (4) | 0.2301 (4) | 0.0518 (14) | |
H6A | 0.065 | 0.0261 | 0.1813 | 0.078* | |
O5 | 0.0965 (6) | −0.0814 (5) | 0.3082 (4) | 0.0600 (16) | |
C17 | 0.0811 (6) | 0.1555 (5) | 0.4146 (5) | 0.0350 (14) | |
H17 | 0.0817 | 0.1918 | 0.3573 | 0.042* | |
C19 | 0.0731 (7) | 0.1476 (5) | 0.5861 (6) | 0.0404 (16) | |
H19 | 0.068 | 0.1784 | 0.6459 | 0.048* | |
C20 | 0.0803 (6) | 0.0069 (5) | 0.3100 (4) | 0.0352 (13) | |
C7 | 0.3693 (7) | 0.1199 (6) | 0.2157 (5) | 0.0410 (16) | |
C11 | 0.2596 (6) | 0.4724 (5) | 0.3332 (6) | 0.0393 (16) | |
C13 | 0.2321 (8) | 0.5841 (7) | 0.4654 (6) | 0.0502 (18) | |
H13 | 0.2292 | 0.5947 | 0.5323 | 0.06* | |
O4 | 0.2878 (6) | 0.3610 (4) | 0.2089 (4) | 0.0524 (15) | |
H4 | 0.3046 | 0.3041 | 0.1993 | 0.079* | |
C3 | 0.4027 (7) | 0.0005 (6) | 0.0868 (5) | 0.0424 (17) | |
H3 | 0.3957 | 0.0502 | 0.0402 | 0.051* | |
C9 | 0.2200 (9) | 0.6408 (6) | 0.2976 (7) | 0.055 (2) | |
H9 | 0.2103 | 0.691 | 0.2516 | 0.066* | |
C4 | 0.3942 (6) | 0.0209 (5) | 0.1861 (5) | 0.0330 (14) | |
O1 | 0.3699 (6) | 0.1345 (4) | 0.3106 (4) | 0.0516 (14) | |
H1 | 0.3557 | 0.192 | 0.3201 | 0.077* | |
C10 | 0.2400 (7) | 0.5486 (6) | 0.2672 (6) | 0.0427 (18) | |
H10 | 0.2404 | 0.537 | 0.2002 | 0.051* | |
N2 | 0.1954 (8) | 0.7515 (6) | 0.4311 (7) | 0.079 (3) | |
H2A | 0.1948 | 0.7623 | 0.493 | 0.095* | |
H2B | 0.1842 | 0.7987 | 0.3893 | 0.095* | |
O3 | 0.3144 (6) | 0.3077 (4) | 0.3655 (4) | 0.0566 (14) | |
C5 | 0.4063 (7) | −0.0544 (5) | 0.2549 (6) | 0.0427 (17) | |
H5 | 0.4002 | −0.0418 | 0.3209 | 0.051* | |
C8 | 0.2139 (7) | 0.6611 (6) | 0.3995 (6) | 0.052 (2) | |
O2 | 0.3485 (6) | 0.1874 (4) | 0.1532 (4) | 0.0576 (15) | |
C14 | 0.2875 (6) | 0.3747 (5) | 0.3016 (5) | 0.0373 (15) | |
C1 | 0.4334 (8) | −0.1696 (6) | 0.1271 (6) | 0.0486 (19) | |
C2 | 0.4216 (8) | −0.0933 (7) | 0.0589 (6) | 0.053 (2) | |
H2 | 0.4267 | −0.1065 | −0.0072 | 0.064* | |
C12 | 0.2544 (7) | 0.4927 (6) | 0.4333 (6) | 0.0442 (17) | |
H12 | 0.2666 | 0.4423 | 0.4792 | 0.053* | |
N1 | 0.4504 (10) | −0.2647 (6) | 0.0985 (7) | 0.084 (3) | |
H1A | 0.4573 | −0.3104 | 0.1419 | 0.101* | |
H1B | 0.4541 | −0.2779 | 0.0375 | 0.101* | |
C6 | 0.4275 (8) | −0.1487 (5) | 0.2246 (7) | 0.052 (2) | |
H6 | 0.4379 | −0.1983 | 0.2713 | 0.063* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N3 | 0.029 (2) | 0.048 (3) | 0.032 (3) | 0.003 (2) | 0.008 (2) | 0.005 (2) |
C15 | 0.030 (2) | 0.035 (3) | 0.033 (3) | 0.000 (3) | 0.013 (2) | 0.004 (3) |
C16 | 0.025 (3) | 0.036 (3) | 0.032 (3) | −0.001 (2) | 0.008 (2) | −0.005 (3) |
C18 | 0.066 (3) | 0.037 (3) | 0.036 (3) | −0.004 (4) | 0.008 (3) | −0.001 (3) |
O6 | 0.061 (3) | 0.050 (3) | 0.045 (3) | 0.005 (2) | 0.010 (2) | −0.008 (2) |
O5 | 0.071 (3) | 0.054 (3) | 0.055 (3) | 0.016 (3) | 0.011 (3) | −0.020 (3) |
C17 | 0.035 (3) | 0.043 (4) | 0.026 (3) | −0.001 (3) | 0.002 (2) | 0.009 (3) |
C19 | 0.052 (4) | 0.039 (4) | 0.030 (3) | −0.003 (3) | 0.008 (3) | −0.001 (3) |
C20 | 0.035 (3) | 0.041 (3) | 0.030 (3) | 0.007 (3) | 0.006 (2) | 0.010 (3) |
C7 | 0.044 (4) | 0.043 (4) | 0.036 (3) | −0.005 (3) | 0.005 (3) | −0.007 (3) |
C11 | 0.025 (3) | 0.038 (4) | 0.049 (4) | 0.000 (3) | −0.010 (3) | −0.002 (3) |
C13 | 0.040 (4) | 0.052 (5) | 0.054 (4) | 0.012 (4) | −0.005 (3) | −0.010 (4) |
O4 | 0.071 (4) | 0.046 (3) | 0.036 (3) | 0.006 (2) | −0.003 (2) | −0.006 (2) |
C3 | 0.044 (4) | 0.042 (4) | 0.041 (4) | −0.002 (3) | 0.008 (3) | −0.003 (3) |
C9 | 0.063 (5) | 0.042 (4) | 0.049 (5) | 0.012 (4) | −0.018 (4) | 0.004 (3) |
C4 | 0.032 (3) | 0.029 (3) | 0.036 (3) | −0.004 (3) | −0.001 (2) | −0.005 (3) |
O1 | 0.072 (4) | 0.046 (3) | 0.036 (3) | −0.003 (3) | 0.004 (2) | −0.006 (2) |
C10 | 0.038 (4) | 0.044 (4) | 0.042 (4) | −0.006 (3) | −0.008 (3) | −0.006 (3) |
N2 | 0.109 (7) | 0.055 (5) | 0.067 (5) | 0.043 (4) | −0.005 (4) | −0.010 (4) |
O3 | 0.085 (4) | 0.040 (3) | 0.049 (3) | −0.003 (3) | 0.021 (3) | 0.000 (2) |
C5 | 0.047 (4) | 0.041 (4) | 0.037 (3) | 0.006 (3) | −0.003 (3) | 0.003 (3) |
C8 | 0.043 (4) | 0.050 (5) | 0.056 (5) | 0.014 (3) | −0.015 (3) | −0.010 (4) |
O2 | 0.091 (4) | 0.039 (3) | 0.043 (3) | 0.005 (3) | 0.013 (3) | 0.006 (2) |
C14 | 0.033 (3) | 0.037 (4) | 0.039 (4) | −0.006 (3) | −0.005 (3) | 0.003 (3) |
C1 | 0.051 (4) | 0.038 (4) | 0.052 (4) | 0.016 (3) | −0.006 (3) | −0.007 (4) |
C2 | 0.054 (4) | 0.058 (5) | 0.049 (4) | 0.006 (4) | 0.011 (4) | −0.018 (4) |
C12 | 0.035 (3) | 0.055 (5) | 0.038 (4) | −0.004 (3) | −0.006 (3) | −0.003 (3) |
N1 | 0.128 (8) | 0.044 (4) | 0.072 (5) | 0.023 (4) | −0.007 (5) | −0.011 (4) |
C6 | 0.060 (5) | 0.033 (4) | 0.055 (5) | 0.014 (3) | −0.015 (4) | −0.003 (3) |
Geometric parameters (Å, º) top
N3—C19 | 1.345 (9) | O4—H4 | 0.82 |
N3—C15 | 1.370 (9) | C3—C2 | 1.373 (12) |
C15—C16 | 1.357 (9) | C3—C4 | 1.402 (10) |
C15—H15 | 0.93 | C3—H3 | 0.93 |
C16—C17 | 1.358 (9) | C9—C10 | 1.364 (11) |
C16—C20 | 1.523 (9) | C9—C8 | 1.430 (14) |
C18—C19 | 1.370 (11) | C9—H9 | 0.93 |
C18—C17 | 1.368 (11) | C4—C5 | 1.393 (10) |
C18—H18 | 0.93 | O1—H1 | 0.82 |
O6—C20 | 1.306 (8) | C10—H10 | 0.93 |
O6—H6A | 0.82 | N2—C8 | 1.345 (12) |
O5—C20 | 1.230 (8) | N2—H2A | 0.86 |
C17—H17 | 0.93 | N2—H2B | 0.86 |
C19—H19 | 0.93 | O3—C14 | 1.269 (9) |
C7—O2 | 1.257 (10) | C5—C6 | 1.393 (10) |
C7—O1 | 1.310 (9) | C5—H5 | 0.93 |
C7—C4 | 1.460 (10) | C1—C6 | 1.374 (13) |
C11—C10 | 1.378 (11) | C1—N1 | 1.388 (11) |
C11—C12 | 1.404 (11) | C1—C2 | 1.398 (13) |
C11—C14 | 1.458 (10) | C2—H2 | 0.93 |
C13—C12 | 1.367 (12) | C12—H12 | 0.93 |
C13—C8 | 1.385 (13) | N1—H1A | 0.86 |
C13—H13 | 0.93 | N1—H1B | 0.86 |
O4—C14 | 1.280 (9) | C6—H6 | 0.93 |
| | | |
C19—N3—C15 | 119.3 (6) | C8—C9—H9 | 119.6 |
C16—C15—N3 | 121.1 (5) | C5—C4—C3 | 119.3 (6) |
C16—C15—H15 | 119.5 | C5—C4—C7 | 120.8 (6) |
N3—C15—H15 | 119.5 | C3—C4—C7 | 119.9 (7) |
C15—C16—C17 | 119.0 (6) | C7—O1—H1 | 109.5 |
C15—C16—C20 | 120.8 (5) | C11—C10—C9 | 121.8 (8) |
C17—C16—C20 | 120.1 (6) | C11—C10—H10 | 119.1 |
C19—C18—C17 | 119.0 (6) | C9—C10—H10 | 119.1 |
C19—C18—H18 | 120.5 | C8—N2—H2A | 120 |
C17—C18—H18 | 120.5 | C8—N2—H2B | 120 |
C20—O6—H6A | 109.5 | H2A—N2—H2B | 120 |
C16—C17—C18 | 120.8 (7) | C4—C5—C6 | 119.9 (7) |
C16—C17—H17 | 119.6 | C4—C5—H5 | 120.1 |
C18—C17—H17 | 119.6 | C6—C5—H5 | 120.1 |
N3—C19—C18 | 120.7 (7) | N2—C8—C13 | 121.0 (8) |
N3—C19—H19 | 119.6 | N2—C8—C9 | 121.7 (9) |
C18—C19—H19 | 119.6 | C13—C8—C9 | 117.3 (7) |
O5—C20—O6 | 122.9 (6) | O3—C14—O4 | 122.4 (7) |
O5—C20—C16 | 119.2 (6) | O3—C14—C11 | 120.0 (7) |
O6—C20—C16 | 117.8 (6) | O4—C14—C11 | 117.5 (6) |
O2—C7—O1 | 122.0 (7) | C6—C1—N1 | 120.0 (8) |
O2—C7—C4 | 121.5 (6) | C6—C1—C2 | 118.3 (7) |
O1—C7—C4 | 116.5 (7) | N1—C1—C2 | 121.7 (8) |
C10—C11—C12 | 117.3 (7) | C3—C2—C1 | 121.8 (7) |
C10—C11—C14 | 121.8 (7) | C3—C2—H2 | 119.1 |
C12—C11—C14 | 120.9 (7) | C1—C2—H2 | 119.1 |
C12—C13—C8 | 120.7 (8) | C13—C12—C11 | 122.1 (8) |
C12—C13—H13 | 119.6 | C13—C12—H12 | 118.9 |
C8—C13—H13 | 119.6 | C11—C12—H12 | 118.9 |
C14—O4—H4 | 109.5 | C1—N1—H1A | 120 |
C2—C3—C4 | 119.5 (7) | C1—N1—H1B | 120 |
C2—C3—H3 | 120.2 | H1A—N1—H1B | 120 |
C4—C3—H3 | 120.2 | C1—C6—C5 | 121.2 (8) |
C10—C9—C8 | 120.8 (8) | C1—C6—H6 | 119.4 |
C10—C9—H9 | 119.6 | C5—C6—H6 | 119.4 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6A···N3i | 0.82 | 1.73 | 2.549 (7) | 177 |
N2—H2A···O2ii | 0.86 | 2.56 | 3.278 (10) | 141 |
N2—H2B···O5iii | 0.86 | 2.11 | 2.930 (11) | 160 |
N1—H1A···O6iv | 0.86 | 2.32 | 3.113 (10) | 154 |
N1—H1B···O3i | 0.86 | 2.57 | 3.303 (11) | 144 |
O4—H4···O2 | 0.82 | 1.81 | 2.620 (8) | 168 |
O1—H1···O3 | 0.82 | 1.79 | 2.596 (8) | 167 |
Symmetry codes: (i) x, −y, z−1/2; (ii) x, −y+1, z+1/2; (iii) x, y+1, z; (iv) x+1/2, y−1/2, z. |
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