Crystal structure and Hirshfeld surface analysis of 4-{[(anthracen-9-yl)meth­yl]amino}­benzoic acid

Ahmed, A.; Faizi, M.S.H.; Ahmad, A.; Ahmad, M.; Fritsky, I.O.

doi:10.1107/S2056989019016207

Crystal structure and Hirshfeld surface analysis of 4-{[(anthracen-9-yl)methyl]amino}benzoic acid

A. Ahmed, M. S. H. Faizi, A. Ahmad, M. Ahmad and I. O. Fritsky

In molecule of the title compound, the benzene ring is inclined to the mean plane of the anthracene ring system (r.m.s. deviation = 0.024 Å) by 75.21 (9)°. In the crystal, a classical carboxylic acid inversion dimer is formed enclosing an $R_{2}^{2}$ (8) ring motif.

Keywords: crystal structure; 4-aminobenzoic acid (PABA); 9-anthraldehyde; hydrogen bonding; C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019016207/su5532sup1.cif Contains datablocks Global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989019016207/su5532Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989019016207/su5532Isup5.cml Supplementary material
	Portable Document Format (PDF) file https://doi.org/10.1107/S2056989019016207/su5532sup3.pdf CSD search S1
	Portable Document Format (PDF) file https://doi.org/10.1107/S2056989019016207/su5532sup4.pdf CSD search S2

CCDC reference: 1969448

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R factor = 0.048
wR factor = 0.141
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT355_ALERT_3_C Long   O-H (X0.82,N0.98A)  O1       - H1       .       1.05 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H8A      ..H11      .       1.99 Ang.
                                                      x,y,z  =      1_555 Check
PLAT420_ALERT_2_C D-H Without Acceptor       N1       --H1A      .     Please Check
PLAT715_ALERT_1_C D-H     Unknown or Inconsistent Label ..........        *N1 Check
PLAT741_ALERT_1_C Bond    Calc    0.930(3), Rep     0.93000 ......    Missing s.u.
              C3       -H3              1.555   1.555 ........     #   10 Check
PLAT741_ALERT_1_C Bond    Calc    0.930(4), Rep     0.93000 ......    Missing s.u.
              C4       -H4              1.555   1.555 ........     #   12 Check
PLAT741_ALERT_1_C Bond    Calc    0.931(3), Rep     0.93000 ......    Missing s.u.
              C6       -H6              1.555   1.555 ........     #   15 Check
PLAT741_ALERT_1_C Bond    Calc    0.930(3), Rep     0.93000 ......    Missing s.u.
              C7       -H7              1.555   1.555 ........     #   17 Check
PLAT741_ALERT_1_C Bond    Calc    0.970(4), Rep     0.97000 ......    Missing s.u.
              C8       -H8A             1.555   1.555 ........     #   18 Check
PLAT741_ALERT_1_C Bond    Calc    0.970(4), Rep     0.97000 ......    Missing s.u.
              C8       -H8B             1.555   1.555 ........     #   19 Check
PLAT741_ALERT_1_C Bond    Calc    0.930(4), Rep     0.93000 ......    Missing s.u.
              C11      -H11             1.555   1.555 ........     #   25 Check
PLAT741_ALERT_1_C Bond    Calc    0.930(4), Rep     0.93000 ......    Missing s.u.
              C12      -H12             1.555   1.555 ........     #   27 Check
PLAT741_ALERT_1_C Bond    Calc    0.930(4), Rep     0.93000 ......    Missing s.u.
              C13      -H13             1.555   1.555 ........     #   29 Check
PLAT741_ALERT_1_C Bond    Calc    0.930(4), Rep     0.93000 ......    Missing s.u.
              C14      -H14             1.555   1.555 ........     #   31 Check
PLAT741_ALERT_1_C Bond    Calc    0.930(3), Rep     0.93000 ......    Missing s.u.
              C16      -H16             1.555   1.555 ........     #   34 Check
PLAT741_ALERT_1_C Bond    Calc    0.930(3), Rep     0.93000 ......    Missing s.u.
              C18      -H18             1.555   1.555 ........     #   38 Check
PLAT741_ALERT_1_C Bond    Calc    0.930(4), Rep     0.93000 ......    Missing s.u.
              C19      -H19             1.555   1.555 ........     #   40 Check
PLAT741_ALERT_1_C Bond    Calc    0.930(4), Rep     0.93000 ......    Missing s.u.
              C20      -H20             1.555   1.555 ........     #   42 Check
PLAT741_ALERT_1_C Bond    Calc    0.930(4), Rep     0.93000 ......    Missing s.u.
              C21      -H21             1.555   1.555 ........     #   44 Check
PLAT742_ALERT_1_C Angle   Calc    108.1(3), Rep      108.00 ......    Missing s.u.
              H8B     -C8      -H8A        1.555  1.555  1.555     #   28 Check
PLAT745_ALERT_1_C D-H     Calc    0.930(4), Rep     0.93000 ......    Missing s.u.
              C4       -H4              1.555   1.555 ........     #   45 Check
PLAT745_ALERT_1_C D-H     Calc    0.931(3), Rep     0.93000 ......    Missing s.u.
              C6       -H6              1.555   1.555 ........     #   45 Check
PLAT745_ALERT_1_C D-H     Calc    0.930(3), Rep     0.93000 ......    Missing s.u.
              C16      -H16             1.555   1.555 ........     #   45 Check
PLAT745_ALERT_1_C D-H     Calc    0.930(3), Rep     0.93000 ......    Missing s.u.
              C18      -H18             1.555   1.555 ........     #   45 Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -2.531 Report
PLAT926_ALERT_1_C Reported and Calculated   R1 Differ by .........    -0.0014 Check
PLAT927_ALERT_1_C Reported and Calculated  wR2 Differ by .........    -0.0012 Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        39% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...         33 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
  27 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

  23 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
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: olex2.refine (Bourhis et al., 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

4-{[(Anthracen-9-yl)methyl]amino}benzoic acid top

Crystal data top

C₂₂H₁₇NO₂	F(000) = 688.3239
M_r = 327.39	D_x = 1.320 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.985 (2) Å	Cell parameters from 3139 reflections
b = 6.0116 (9) Å	θ = 3.1–28.2°
c = 19.106 (3) Å	µ = 0.09 mm⁻¹
β = 106.796 (5)°	T = 100 K
V = 1647.7 (4) Å³	Block, pale-yellow
Z = 4	0.4 × 0.27 × 0.18 mm

Data collection top

Bruker APEXII CCD diffractometer	1975 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.118
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 25.1°, θ_min = 2.8°
T_min = 0.629, T_max = 0.746	h = −20→20
25595 measured reflections	k = −8→8
2913 independent reflections	l = −25→25

Refinement top

Refinement on F²	29 constraints
Least-squares matrix: full	Primary atom site location: iterative
R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.0452P)² + 0.9105P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.0003
2913 reflections	Δρ_max = 0.38 e Å⁻³
235 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.47155 (12)	0.7404 (3)	0.95012 (10)	0.0304 (5)
O2	0.57543 (12)	1.0125 (3)	0.95315 (10)	0.0317 (5)
N1	0.66609 (14)	0.3342 (4)	0.72544 (12)	0.0252 (5)
C1	0.54000 (17)	0.8318 (4)	0.92904 (14)	0.0238 (6)
C2	0.57055 (16)	0.7035 (4)	0.87497 (13)	0.0212 (6)
C3	0.63813 (16)	0.7902 (4)	0.84570 (14)	0.0230 (6)
H3	0.66266 (16)	0.9303 (4)	0.86054 (14)	0.0276 (7)*
C4	0.66973 (17)	0.6741 (4)	0.79531 (13)	0.0222 (6)
H4	0.71436 (17)	0.7367 (4)	0.77612 (13)	0.0266 (7)*
C5	0.63421 (16)	0.4606 (4)	0.77302 (13)	0.0209 (6)
C6	0.56515 (17)	0.3731 (4)	0.80193 (13)	0.0224 (6)
H6	0.53997 (17)	0.2335 (4)	0.78701 (13)	0.0269 (7)*
C7	0.53463 (16)	0.4920 (4)	0.85202 (13)	0.0215 (6)
H7	0.48944 (16)	0.4312 (4)	0.87096 (13)	0.0258 (7)*
C8	0.74688 (17)	0.3903 (4)	0.70105 (14)	0.0243 (6)
H8a	0.72642 (17)	0.4653 (4)	0.65418 (14)	0.0291 (7)*
H8b	0.78696 (17)	0.4913 (4)	0.73586 (14)	0.0291 (7)*
C9	0.80133 (16)	0.1835 (4)	0.69386 (13)	0.0208 (6)
C10	0.80253 (16)	0.1014 (4)	0.62496 (13)	0.0204 (6)
C11	0.75646 (17)	0.2083 (4)	0.55691 (14)	0.0257 (6)
H11	0.72308 (17)	0.3384 (4)	0.55740 (14)	0.0308 (7)*
C12	0.76034 (18)	0.1242 (5)	0.49175 (14)	0.0294 (7)
H12	0.72945 (18)	0.1972 (5)	0.44864 (14)	0.0353 (8)*
C13	0.81084 (18)	−0.0732 (5)	0.48869 (15)	0.0310 (7)
H13	0.81360 (18)	−0.1278 (5)	0.44382 (15)	0.0372 (8)*
C14	0.85503 (17)	−0.1822 (4)	0.55102 (14)	0.0269 (6)
H14	0.88740 (17)	−0.3124 (4)	0.54841 (14)	0.0322 (7)*
C15	0.85289 (16)	−0.1007 (4)	0.62098 (14)	0.0216 (6)
C16	0.89943 (16)	−0.2114 (4)	0.68500 (14)	0.0225 (6)
H16	0.93082 (16)	−0.3429 (4)	0.68203 (14)	0.0270 (7)*
C17	0.90025 (16)	−0.1302 (4)	0.75358 (13)	0.0202 (6)
C18	0.94936 (16)	−0.2430 (4)	0.81929 (14)	0.0255 (6)
H18	0.98095 (16)	−0.3741 (4)	0.81619 (14)	0.0307 (7)*
C19	0.95099 (18)	−0.1630 (4)	0.88627 (15)	0.0289 (7)
H19	0.98374 (18)	−0.2383 (4)	0.92840 (15)	0.0347 (8)*
C20	0.90250 (17)	0.0354 (4)	0.89133 (15)	0.0287 (6)
H20	0.90346 (17)	0.0897 (4)	0.93712 (15)	0.0344 (8)*
C21	0.85437 (17)	0.1482 (4)	0.83019 (14)	0.0243 (6)
H21	0.82321 (17)	0.2784 (4)	0.83510 (14)	0.0291 (7)*
C22	0.85075 (16)	0.0706 (4)	0.75862 (14)	0.0204 (6)
H1	0.457 (2)	0.850 (6)	0.9884 (19)	0.074 (11)*
H1a	0.635 (2)	0.201 (5)	0.7113 (15)	0.042 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0321 (10)	0.0298 (10)	0.0357 (12)	−0.0061 (8)	0.0198 (9)	−0.0083 (9)
O2	0.0368 (11)	0.0274 (10)	0.0352 (12)	−0.0070 (9)	0.0172 (9)	−0.0115 (9)
N1	0.0215 (12)	0.0251 (12)	0.0322 (14)	−0.0041 (10)	0.0127 (10)	−0.0071 (10)
C1	0.0234 (14)	0.0238 (14)	0.0239 (15)	0.0007 (11)	0.0065 (11)	0.0001 (11)
C2	0.0200 (13)	0.0223 (13)	0.0209 (14)	0.0021 (11)	0.0053 (11)	−0.0011 (11)
C3	0.0204 (13)	0.0206 (13)	0.0275 (15)	0.0013 (11)	0.0059 (11)	−0.0024 (11)
C4	0.0197 (13)	0.0236 (13)	0.0242 (14)	−0.0003 (11)	0.0078 (11)	0.0018 (11)
C5	0.0195 (13)	0.0207 (13)	0.0219 (14)	0.0026 (10)	0.0051 (11)	0.0004 (11)
C6	0.0215 (13)	0.0194 (13)	0.0251 (15)	0.0012 (11)	0.0050 (11)	−0.0012 (11)
C7	0.0185 (13)	0.0229 (13)	0.0230 (14)	0.0015 (11)	0.0058 (11)	0.0036 (11)
C8	0.0234 (13)	0.0218 (13)	0.0295 (16)	−0.0009 (11)	0.0105 (12)	−0.0011 (11)
C9	0.0193 (13)	0.0202 (13)	0.0241 (14)	−0.0013 (10)	0.0081 (11)	−0.0007 (11)
C10	0.0147 (12)	0.0227 (13)	0.0242 (15)	−0.0019 (10)	0.0063 (11)	−0.0005 (11)
C11	0.0216 (13)	0.0277 (14)	0.0279 (15)	0.0013 (11)	0.0076 (11)	0.0009 (12)
C12	0.0250 (14)	0.0397 (16)	0.0215 (15)	0.0021 (12)	0.0037 (12)	0.0020 (12)
C13	0.0267 (14)	0.0393 (16)	0.0258 (16)	0.0018 (13)	0.0057 (12)	−0.0067 (13)
C14	0.0238 (13)	0.0287 (14)	0.0276 (15)	0.0006 (12)	0.0066 (12)	−0.0089 (12)
C15	0.0170 (12)	0.0235 (13)	0.0239 (15)	−0.0030 (10)	0.0054 (11)	−0.0043 (11)
C16	0.0202 (13)	0.0190 (13)	0.0297 (15)	0.0000 (11)	0.0094 (11)	−0.0029 (11)
C17	0.0171 (12)	0.0212 (13)	0.0235 (14)	−0.0022 (10)	0.0076 (11)	0.0009 (11)
C18	0.0195 (13)	0.0249 (14)	0.0318 (16)	−0.0010 (11)	0.0066 (11)	0.0024 (12)
C19	0.0234 (14)	0.0345 (16)	0.0272 (16)	−0.0043 (12)	0.0047 (11)	0.0064 (12)
C20	0.0285 (15)	0.0338 (15)	0.0245 (16)	−0.0051 (12)	0.0087 (12)	−0.0032 (12)
C21	0.0216 (13)	0.0261 (14)	0.0268 (15)	−0.0023 (11)	0.0096 (11)	−0.0029 (12)
C22	0.0181 (12)	0.0203 (13)	0.0242 (14)	−0.0054 (10)	0.0085 (11)	−0.0030 (11)

Geometric parameters (Å, º) top

O1—C1	1.325 (3)	C10—C15	1.443 (3)
O1—H1	1.05 (4)	C11—H11	0.9300
O2—C1	1.238 (3)	C11—C12	1.360 (3)
N1—C5	1.372 (3)	C12—H12	0.9300
N1—C8	1.457 (3)	C12—C13	1.418 (4)
N1—H1a	0.92 (3)	C13—H13	0.9300
C1—C2	1.465 (3)	C13—C14	1.353 (4)
C2—C3	1.392 (3)	C14—H14	0.9300
C2—C7	1.401 (3)	C14—C15	1.433 (3)
C3—H3	0.9300	C15—C16	1.390 (3)
C3—C4	1.379 (3)	C16—H16	0.9300
C4—H4	0.9300	C16—C17	1.395 (3)
C4—C5	1.408 (3)	C17—C18	1.429 (3)
C5—C6	1.408 (3)	C17—C22	1.435 (3)
C6—H6	0.9300	C18—H18	0.9300
C6—C7	1.375 (3)	C18—C19	1.360 (4)
C7—H7	0.9300	C19—H19	0.9300
C8—H8a	0.9700	C19—C20	1.414 (4)
C8—H8b	0.9700	C20—H20	0.9300
C8—C9	1.515 (3)	C20—C21	1.363 (3)
C9—C10	1.411 (3)	C21—H21	0.9300
C9—C22	1.418 (3)	C21—C22	1.431 (3)
C10—C11	1.436 (3)

H1—O1—C1	106.6 (18)	H11—C11—C10	119.13 (14)
C8—N1—C5	124.4 (2)	C12—C11—C10	121.7 (2)
H1a—N1—C5	115.7 (18)	C12—C11—H11	119.13 (16)
H1a—N1—C8	119.8 (18)	H12—C12—C11	119.57 (16)
O2—C1—O1	122.5 (2)	C13—C12—C11	120.9 (3)
C2—C1—O1	115.1 (2)	C13—C12—H12	119.57 (16)
C2—C1—O2	122.5 (2)	H13—C13—C12	119.99 (16)
C3—C2—C1	119.9 (2)	C14—C13—C12	120.0 (3)
C7—C2—C1	121.9 (2)	C14—C13—H13	119.99 (16)
C7—C2—C3	118.2 (2)	H14—C14—C13	119.39 (16)
H3—C3—C2	119.07 (15)	C15—C14—C13	121.2 (2)
C4—C3—C2	121.9 (2)	C15—C14—H14	119.39 (15)
C4—C3—H3	119.07 (15)	C14—C15—C10	119.3 (2)
H4—C4—C3	120.11 (15)	C16—C15—C10	119.6 (2)
C5—C4—C3	119.8 (2)	C16—C15—C14	121.1 (2)
C5—C4—H4	120.11 (14)	H16—C16—C15	119.16 (14)
C4—C5—N1	122.1 (2)	C17—C16—C15	121.7 (2)
C6—C5—N1	119.3 (2)	C17—C16—H16	119.16 (14)
C6—C5—C4	118.6 (2)	C18—C17—C16	121.5 (2)
H6—C6—C5	119.71 (14)	C22—C17—C16	119.5 (2)
C7—C6—C5	120.6 (2)	C22—C17—C18	119.0 (2)
C7—C6—H6	119.71 (15)	H18—C18—C17	119.22 (15)
C6—C7—C2	121.0 (2)	C19—C18—C17	121.6 (2)
H7—C7—C2	119.49 (14)	C19—C18—H18	119.22 (16)
H7—C7—C6	119.49 (15)	H19—C19—C18	120.26 (16)
H8a—C8—N1	109.44 (13)	C20—C19—C18	119.5 (3)
H8b—C8—N1	109.44 (13)	C20—C19—H19	120.26 (16)
H8b—C8—H8a	108.0	H20—C20—C19	119.47 (16)
C9—C8—N1	111.0 (2)	C21—C20—C19	121.1 (3)
C9—C8—H8a	109.44 (14)	C21—C20—H20	119.47 (16)
C9—C8—H8b	109.44 (13)	H21—C21—C20	119.29 (16)
C10—C9—C8	121.6 (2)	C22—C21—C20	121.4 (2)
C22—C9—C8	118.2 (2)	C22—C21—H21	119.29 (14)
C22—C9—C10	120.2 (2)	C17—C22—C9	119.6 (2)
C11—C10—C9	123.8 (2)	C21—C22—C9	123.0 (2)
C15—C10—C9	119.4 (2)	C21—C22—C17	117.4 (2)
C15—C10—C11	116.8 (2)

C8—N1—C5—C4	8.8 (4)	C9—C10—C11—C12	179.3 (3)
C8—N1—C5—C6	−169.8 (2)	C15—C10—C11—C12	−0.3 (4)
C5—N1—C8—C9	142.6 (2)	C9—C10—C15—C14	−179.2 (2)
O1—C1—C2—C3	176.1 (2)	C9—C10—C15—C16	0.0 (4)
O1—C1—C2—C7	−4.8 (4)	C11—C10—C15—C14	0.4 (3)
O2—C1—C2—C3	−3.8 (4)	C11—C10—C15—C16	179.6 (2)
O2—C1—C2—C7	175.3 (2)	C10—C11—C12—C13	−0.3 (4)
C1—C2—C3—C4	179.2 (2)	C11—C12—C13—C14	0.8 (4)
C7—C2—C3—C4	0.1 (4)	C12—C13—C14—C15	−0.7 (4)
C1—C2—C7—C6	−179.1 (2)	C13—C14—C15—C10	0.1 (4)
C3—C2—C7—C6	0.0 (4)	C13—C14—C15—C16	−179.1 (3)
C2—C3—C4—C5	−0.8 (4)	C10—C15—C16—C17	−1.1 (4)
C3—C4—C5—N1	−177.2 (2)	C14—C15—C16—C17	178.0 (2)
C3—C4—C5—C6	1.4 (4)	C15—C16—C17—C18	−179.1 (2)
N1—C5—C6—C7	177.3 (2)	C15—C16—C17—C22	1.0 (4)
C4—C5—C6—C7	−1.4 (4)	C16—C17—C18—C19	179.4 (2)
C5—C6—C7—C2	0.7 (4)	C22—C17—C18—C19	−0.7 (4)
N1—C8—C9—C10	109.5 (3)	C16—C17—C22—C9	0.3 (4)
N1—C8—C9—C22	−69.6 (3)	C16—C17—C22—C21	−179.5 (2)
C8—C9—C10—C11	2.5 (4)	C18—C17—C22—C9	−179.7 (2)
C8—C9—C10—C15	−177.9 (2)	C18—C17—C22—C21	0.6 (4)
C22—C9—C10—C11	−178.4 (2)	C17—C18—C19—C20	0.5 (4)
C22—C9—C10—C15	1.3 (4)	C18—C19—C20—C21	−0.2 (4)
C8—C9—C22—C17	177.8 (2)	C19—C20—C21—C22	0.1 (4)
C8—C9—C22—C21	−2.5 (4)	C20—C21—C22—C9	179.9 (3)
C10—C9—C22—C17	−1.4 (4)	C20—C21—C22—C17	−0.4 (4)
C10—C9—C22—C21	178.3 (2)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, and Cg4 are the centroids of the C2–C7, C9/C10/C15–C17/C22 and C17–C22 rings, respectively. Approximative geometrical parameters are given for the weak N—H..π interaction.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	1.05 (4)	1.58 (3)	2.621 (3)	172 (3)
N1—H1A···Cg1ⁱⁱ	0.93 (3)	3.49	4.140	129
C4—H4···Cg4ⁱⁱⁱ	0.93	2.98 (1)	3.752 (3)	141 (1)
C6—H6···Cg1ⁱⁱ	0.93	2.69 (1)	3.410 (3)	135 (1)
C16—H16···Cg4^iv	0.93	2.83 (1)	3.644 (3)	147 (1)
C18—H18···Cg2^iv	0.93	2.69 (1)	3.452 (3)	140 (1)

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

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Crystal structure and Hirshfeld surface analysis of 4-{[(anthracen-9-yl)meth­yl]amino}­benzoic acid

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Crystal structure and Hirshfeld surface analysis of 4-{[(anthracen-9-yl)methyl]amino}benzoic acid