Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, 2C7H7NO2·C6H5NO2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046812/ci2206sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046812/ci2206Isup2.hkl
Contains datablock I

CCDC reference: 629523

Key indicators

  • Single-crystal X-ray study
  • T = 303 K
  • Mean [sigma](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

Computing details top

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·C6H5NO2F(000) = 832
Mr = 397.38Dx = 1.395 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 25 reflections
a = 10.1803 (4) Åθ = 2–25°
b = 13.8050 (7) ŵ = 0.11 mm1
c = 13.6530 (8) ÅT = 303 K
β = 99.680 (4)°Block, yellow
V = 1891.46 (16) Å30.4 × 0.25 × 0.2 mm
Z = 4
Data collection top
Nonius MACH3 sealed-tube
diffractometer
Rint = 0.043
ω–2θ scansθmax = 25.0°, θmin = 2.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 112
Tmin = 0.969, Tmax = 0.979k = 1616
3471 measured reflectionsl = 1616
1614 independent reflections3 standard reflections every 60 min
1281 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullH-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 = 1.05Δρmax = 0.33 e Å3
1614 reflectionsΔρmin = 0.30 e Å3
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
xyzUiso*/Ueq
N30.0741 (5)0.0502 (5)0.5822 (4)0.0359 (14)
C150.0776 (7)0.0052 (4)0.4932 (5)0.0316 (13)
H150.07720.06210.49020.038*
C160.0817 (5)0.0572 (5)0.4095 (5)0.0308 (13)
C180.0796 (10)0.2018 (4)0.5030 (6)0.0461 (13)
H180.08290.2690.50660.055*
O60.0641 (5)0.0605 (4)0.2301 (4)0.0518 (14)
H6A0.0650.02610.18130.078*
O50.0965 (6)0.0814 (5)0.3082 (4)0.0600 (16)
C170.0811 (6)0.1555 (5)0.4146 (5)0.0350 (14)
H170.08170.19180.35730.042*
C190.0731 (7)0.1476 (5)0.5861 (6)0.0404 (16)
H190.0680.17840.64590.048*
C200.0803 (6)0.0069 (5)0.3100 (4)0.0352 (13)
C70.3693 (7)0.1199 (6)0.2157 (5)0.0410 (16)
C110.2596 (6)0.4724 (5)0.3332 (6)0.0393 (16)
C130.2321 (8)0.5841 (7)0.4654 (6)0.0502 (18)
H130.22920.59470.53230.06*
O40.2878 (6)0.3610 (4)0.2089 (4)0.0524 (15)
H40.30460.30410.19930.079*
C30.4027 (7)0.0005 (6)0.0868 (5)0.0424 (17)
H30.39570.05020.04020.051*
C90.2200 (9)0.6408 (6)0.2976 (7)0.055 (2)
H90.21030.6910.25160.066*
C40.3942 (6)0.0209 (5)0.1861 (5)0.0330 (14)
O10.3699 (6)0.1345 (4)0.3106 (4)0.0516 (14)
H10.35570.1920.32010.077*
C100.2400 (7)0.5486 (6)0.2672 (6)0.0427 (18)
H100.24040.5370.20020.051*
N20.1954 (8)0.7515 (6)0.4311 (7)0.079 (3)
H2A0.19480.76230.4930.095*
H2B0.18420.79870.38930.095*
O30.3144 (6)0.3077 (4)0.3655 (4)0.0566 (14)
C50.4063 (7)0.0544 (5)0.2549 (6)0.0427 (17)
H50.40020.04180.32090.051*
C80.2139 (7)0.6611 (6)0.3995 (6)0.052 (2)
O20.3485 (6)0.1874 (4)0.1532 (4)0.0576 (15)
C140.2875 (6)0.3747 (5)0.3016 (5)0.0373 (15)
C10.4334 (8)0.1696 (6)0.1271 (6)0.0486 (19)
C20.4216 (8)0.0933 (7)0.0589 (6)0.053 (2)
H20.42670.10650.00720.064*
C120.2544 (7)0.4927 (6)0.4333 (6)0.0442 (17)
H120.26660.44230.47920.053*
N10.4504 (10)0.2647 (6)0.0985 (7)0.084 (3)
H1A0.45730.31040.14190.101*
H1B0.45410.27790.03750.101*
C60.4275 (8)0.1487 (5)0.2246 (7)0.052 (2)
H60.43790.19830.27130.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N30.029 (2)0.048 (3)0.032 (3)0.003 (2)0.008 (2)0.005 (2)
C150.030 (2)0.035 (3)0.033 (3)0.000 (3)0.013 (2)0.004 (3)
C160.025 (3)0.036 (3)0.032 (3)0.001 (2)0.008 (2)0.005 (3)
C180.066 (3)0.037 (3)0.036 (3)0.004 (4)0.008 (3)0.001 (3)
O60.061 (3)0.050 (3)0.045 (3)0.005 (2)0.010 (2)0.008 (2)
O50.071 (3)0.054 (3)0.055 (3)0.016 (3)0.011 (3)0.020 (3)
C170.035 (3)0.043 (4)0.026 (3)0.001 (3)0.002 (2)0.009 (3)
C190.052 (4)0.039 (4)0.030 (3)0.003 (3)0.008 (3)0.001 (3)
C200.035 (3)0.041 (3)0.030 (3)0.007 (3)0.006 (2)0.010 (3)
C70.044 (4)0.043 (4)0.036 (3)0.005 (3)0.005 (3)0.007 (3)
C110.025 (3)0.038 (4)0.049 (4)0.000 (3)0.010 (3)0.002 (3)
C130.040 (4)0.052 (5)0.054 (4)0.012 (4)0.005 (3)0.010 (4)
O40.071 (4)0.046 (3)0.036 (3)0.006 (2)0.003 (2)0.006 (2)
C30.044 (4)0.042 (4)0.041 (4)0.002 (3)0.008 (3)0.003 (3)
C90.063 (5)0.042 (4)0.049 (5)0.012 (4)0.018 (4)0.004 (3)
C40.032 (3)0.029 (3)0.036 (3)0.004 (3)0.001 (2)0.005 (3)
O10.072 (4)0.046 (3)0.036 (3)0.003 (3)0.004 (2)0.006 (2)
C100.038 (4)0.044 (4)0.042 (4)0.006 (3)0.008 (3)0.006 (3)
N20.109 (7)0.055 (5)0.067 (5)0.043 (4)0.005 (4)0.010 (4)
O30.085 (4)0.040 (3)0.049 (3)0.003 (3)0.021 (3)0.000 (2)
C50.047 (4)0.041 (4)0.037 (3)0.006 (3)0.003 (3)0.003 (3)
C80.043 (4)0.050 (5)0.056 (5)0.014 (3)0.015 (3)0.010 (4)
O20.091 (4)0.039 (3)0.043 (3)0.005 (3)0.013 (3)0.006 (2)
C140.033 (3)0.037 (4)0.039 (4)0.006 (3)0.005 (3)0.003 (3)
C10.051 (4)0.038 (4)0.052 (4)0.016 (3)0.006 (3)0.007 (4)
C20.054 (4)0.058 (5)0.049 (4)0.006 (4)0.011 (4)0.018 (4)
C120.035 (3)0.055 (5)0.038 (4)0.004 (3)0.006 (3)0.003 (3)
N10.128 (8)0.044 (4)0.072 (5)0.023 (4)0.007 (5)0.011 (4)
C60.060 (5)0.033 (4)0.055 (5)0.014 (3)0.015 (4)0.003 (3)
Geometric parameters (Å, º) top
N3—C191.345 (9)O4—H40.82
N3—C151.370 (9)C3—C21.373 (12)
C15—C161.357 (9)C3—C41.402 (10)
C15—H150.93C3—H30.93
C16—C171.358 (9)C9—C101.364 (11)
C16—C201.523 (9)C9—C81.430 (14)
C18—C191.370 (11)C9—H90.93
C18—C171.368 (11)C4—C51.393 (10)
C18—H180.93O1—H10.82
O6—C201.306 (8)C10—H100.93
O6—H6A0.82N2—C81.345 (12)
O5—C201.230 (8)N2—H2A0.86
C17—H170.93N2—H2B0.86
C19—H190.93O3—C141.269 (9)
C7—O21.257 (10)C5—C61.393 (10)
C7—O11.310 (9)C5—H50.93
C7—C41.460 (10)C1—C61.374 (13)
C11—C101.378 (11)C1—N11.388 (11)
C11—C121.404 (11)C1—C21.398 (13)
C11—C141.458 (10)C2—H20.93
C13—C121.367 (12)C12—H120.93
C13—C81.385 (13)N1—H1A0.86
C13—H130.93N1—H1B0.86
O4—C141.280 (9)C6—H60.93
C19—N3—C15119.3 (6)C8—C9—H9119.6
C16—C15—N3121.1 (5)C5—C4—C3119.3 (6)
C16—C15—H15119.5C5—C4—C7120.8 (6)
N3—C15—H15119.5C3—C4—C7119.9 (7)
C15—C16—C17119.0 (6)C7—O1—H1109.5
C15—C16—C20120.8 (5)C11—C10—C9121.8 (8)
C17—C16—C20120.1 (6)C11—C10—H10119.1
C19—C18—C17119.0 (6)C9—C10—H10119.1
C19—C18—H18120.5C8—N2—H2A120
C17—C18—H18120.5C8—N2—H2B120
C20—O6—H6A109.5H2A—N2—H2B120
C16—C17—C18120.8 (7)C4—C5—C6119.9 (7)
C16—C17—H17119.6C4—C5—H5120.1
C18—C17—H17119.6C6—C5—H5120.1
N3—C19—C18120.7 (7)N2—C8—C13121.0 (8)
N3—C19—H19119.6N2—C8—C9121.7 (9)
C18—C19—H19119.6C13—C8—C9117.3 (7)
O5—C20—O6122.9 (6)O3—C14—O4122.4 (7)
O5—C20—C16119.2 (6)O3—C14—C11120.0 (7)
O6—C20—C16117.8 (6)O4—C14—C11117.5 (6)
O2—C7—O1122.0 (7)C6—C1—N1120.0 (8)
O2—C7—C4121.5 (6)C6—C1—C2118.3 (7)
O1—C7—C4116.5 (7)N1—C1—C2121.7 (8)
C10—C11—C12117.3 (7)C3—C2—C1121.8 (7)
C10—C11—C14121.8 (7)C3—C2—H2119.1
C12—C11—C14120.9 (7)C1—C2—H2119.1
C12—C13—C8120.7 (8)C13—C12—C11122.1 (8)
C12—C13—H13119.6C13—C12—H12118.9
C8—C13—H13119.6C11—C12—H12118.9
C14—O4—H4109.5C1—N1—H1A120
C2—C3—C4119.5 (7)C1—N1—H1B120
C2—C3—H3120.2H1A—N1—H1B120
C4—C3—H3120.2C1—C6—C5121.2 (8)
C10—C9—C8120.8 (8)C1—C6—H6119.4
C10—C9—H9119.6C5—C6—H6119.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6A···N3i0.821.732.549 (7)177
N2—H2A···O2ii0.862.563.278 (10)141
N2—H2B···O5iii0.862.112.930 (11)160
N1—H1A···O6iv0.862.323.113 (10)154
N1—H1B···O3i0.862.573.303 (11)144
O4—H4···O20.821.812.620 (8)168
O1—H1···O30.821.792.596 (8)167
Symmetry codes: (i) x, y, z1/2; (ii) x, y+1, z+1/2; (iii) x, y+1, z; (iv) x+1/2, y1/2, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds