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

In the crystal structure of the title compound inter­molecular hydrogen-bonding inter­actions and weak C—H...π inter­actions between the constituents lead to the formation of a three-dimensional network. Hirshfeld surface analysis revealed that H...H inter­actions dominate the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.057
• wR factor = 0.184
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.139
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00408 Ang.
PLAT355_ALERT_3_C Long   O-H (X0.82,N0.98A)  O1       - H1       .       1.02 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H8B      ..H11      .       1.98 Ang.
                                                      x,y,z  =      1_555 Check
PLAT741_ALERT_1_C Bond    Calc    0.880(3), Rep     0.88000 ......    Missing s.u.
              N1       -H1A             1.555   1.555 ........     #    5 Check
PLAT741_ALERT_1_C Bond    Calc    0.949(3), Rep     0.95000 ......    Missing s.u.
              C3       -H3              1.555   1.555 ........     #   14 Check
PLAT741_ALERT_1_C Bond    Calc    0.950(4), Rep     0.95000 ......    Missing s.u.
              C4       -H4              1.555   1.555 ........     #   16 Check
PLAT741_ALERT_1_C Bond    Calc    0.949(3), Rep     0.95000 ......    Missing s.u.
              C6       -H6              1.555   1.555 ........     #   19 Check
PLAT741_ALERT_1_C Bond    Calc    0.950(4), Rep     0.95000 ......    Missing s.u.
              C7       -H7              1.555   1.555 ........     #   21 Check
PLAT741_ALERT_1_C Bond    Calc    0.990(4), Rep     0.99000 ......    Missing s.u.
              C8       -H8A             1.555   1.555 ........     #   22 Check
PLAT741_ALERT_1_C Bond    Calc    0.990(4), Rep     0.99000 ......    Missing s.u.
              C8       -H8B             1.555   1.555 ........     #   23 Check
PLAT741_ALERT_1_C Bond    Calc    0.950(4), Rep     0.95000 ......    Missing s.u.
              C11      -H11             1.555   1.555 ........     #   29 Check
PLAT741_ALERT_1_C Bond    Calc    0.950(5), Rep     0.95000 ......    Missing s.u.
              C12      -H12             1.555   1.555 ........     #   31 Check
PLAT741_ALERT_1_C Bond    Calc    0.950(5), Rep     0.95000 ......    Missing s.u.
              C13      -H13             1.555   1.555 ........     #   33 Check
PLAT741_ALERT_1_C Bond    Calc    0.950(5), Rep     0.95000 ......    Missing s.u.
              C14      -H14             1.555   1.555 ........     #   35 Check
PLAT741_ALERT_1_C Bond    Calc    0.950(4), Rep     0.95000 ......    Missing s.u.
              C16      -H16             1.555   1.555 ........     #   38 Check
PLAT741_ALERT_1_C Bond    Calc    0.950(4), Rep     0.95000 ......    Missing s.u.
              C18      -H18             1.555   1.555 ........     #   42 Check
PLAT741_ALERT_1_C Bond    Calc    0.950(4), Rep     0.95000 ......    Missing s.u.
              C19      -H19             1.555   1.555 ........     #   44 Check
PLAT741_ALERT_1_C Bond    Calc    0.950(4), Rep     0.95000 ......    Missing s.u.
              C20      -H20             1.555   1.555 ........     #   46 Check
PLAT741_ALERT_1_C Bond    Calc    0.950(4), Rep     0.95000 ......    Missing s.u.
              C21      -H21             1.555   1.555 ........     #   48 Check
PLAT741_ALERT_1_C Bond    Calc    0.950(4), Rep     0.95000 ......    Missing s.u.
              C23      -H23             1.555   1.555 ........     #   50 Check
PLAT741_ALERT_1_C Bond    Calc    0.980(5), Rep     0.98000 ......    Missing s.u.
              C24      -H24A            1.555   1.555 ........     #   51 Check
PLAT741_ALERT_1_C Bond    Calc   0.980(10), Rep     0.98000 ......    Missing s.u.
              C24      -H24B            1.555   1.555 ........     #   52 Check
PLAT741_ALERT_1_C Bond    Calc   0.980(15), Rep     0.98000 ......    Missing s.u.
              C24      -H24C            1.555   1.555 ........     #   53 Check
PLAT741_ALERT_1_C Bond    Calc    0.980(6), Rep     0.98000 ......    Missing s.u.
              C25      -H25A            1.555   1.555 ........     #   54 Check
PLAT741_ALERT_1_C Bond    Calc   0.980(13), Rep     0.98000 ......    Missing s.u.
              C25      -H25B            1.555   1.555 ........     #   55 Check
PLAT741_ALERT_1_C Bond    Calc   0.980(12), Rep     0.98000 ......    Missing s.u.
              C25      -H25C            1.555   1.555 ........     #   56 Check
PLAT742_ALERT_1_C Angle   Calc    108.3(3), Rep      108.30 ......    Missing s.u.
              H8B     -C8      -H8A        1.555  1.555  1.555     #   31 Check
PLAT742_ALERT_1_C Angle   Calc    109.5(4), Rep      109.50 ......    Missing s.u.
              H24A    -C24     -N2         1.555  1.555  1.555     #   80 Check
PLAT742_ALERT_1_C Angle   Calc    109.5(5), Rep      109.50 ......    Missing s.u.
              H24B    -C24     -N2         1.555  1.555  1.555     #   81 Check
PLAT742_ALERT_1_C Angle   Calc   109.4(13), Rep      109.50 ......    Missing s.u.
              H24B    -C24     -H24A       1.555  1.555  1.555     #   82 Check
PLAT742_ALERT_1_C Angle   Calc    109.5(6), Rep      109.50 ......    Missing s.u.
              H24C    -C24     -N2         1.555  1.555  1.555     #   83 Check
PLAT742_ALERT_1_C Angle   Calc   109.6(11), Rep      109.50 ......    Missing s.u.
              H24C    -C24     -H24A       1.555  1.555  1.555     #   84 Check
PLAT742_ALERT_1_C Angle   Calc   109.4(13), Rep      109.50 ......    Missing s.u.
              H24C    -C24     -H24B       1.555  1.555  1.555     #   85 Check
PLAT742_ALERT_1_C Angle   Calc    109.5(5), Rep      109.50 ......    Missing s.u.
              H25A    -C25     -N2         1.555  1.555  1.555     #   86 Check
PLAT742_ALERT_1_C Angle   Calc    109.5(4), Rep      109.50 ......    Missing s.u.
              H25B    -C25     -N2         1.555  1.555  1.555     #   87 Check
PLAT742_ALERT_1_C Angle   Calc   109.4(12), Rep      109.50 ......    Missing s.u.
              H25B    -C25     -H25A       1.555  1.555  1.555     #   88 Check
PLAT742_ALERT_1_C Angle   Calc    109.4(7), Rep      109.50 ......    Missing s.u.
              H25C    -C25     -N2         1.555  1.555  1.555     #   89 Check
PLAT742_ALERT_1_C Angle   Calc   109.7(11), Rep      109.50 ......    Missing s.u.
              H25C    -C25     -H25A       1.555  1.555  1.555     #   90 Check
PLAT742_ALERT_1_C Angle   Calc   109.5(12), Rep      109.50 ......    Missing s.u.
              H25C    -C25     -H25B       1.555  1.555  1.555     #   91 Check
PLAT745_ALERT_1_C D-H     Calc    0.949(3), Rep     0.95000 ......    Missing s.u.
              C6       -H6              1.555   1.555 ........     #   56 Check
PLAT745_ALERT_1_C D-H     Calc    0.950(4), Rep     0.95000 ......    Missing s.u.
              C7       -H7              1.555   1.555 ........     #   56 Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -3.192 Report
PLAT926_ALERT_1_C Reported and Calculated   R1 Differ by .........    -0.0012 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT020_ALERT_3_G The Value of Rint is Greater Than 0.12 .........      0.139 Report
PLAT432_ALERT_2_G Short Inter X...Y Contact  C23      ..C23              3.13 Ang.
                                                2-x,2-y,1-z  =      3_776 Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              C3 H7 N O
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).          4 Note
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...         47 Check

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

  39 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
   8 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

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); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

4-{[(Anthracen-9-yl)methyl]amino}benzoic acid dimethylformamide monosolvate#

Crystal data

C22H17NO2·C3H7NO	F(000) = 848.4030
Mr = 400.48	Dx = 1.289 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.6878 (9) Å	Cell parameters from 4326 reflections
b = 8.9088 (7) Å	θ = 3.2–28.1°
c = 21.9503 (19) Å	µ = 0.09 mm^−1
β = 99.049 (3)°	T = 100 K
V = 2064.0 (3) Å^3	Block, colourless
Z = 4	0.36 × 0.28 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer	2477 reflections with I ≥ 2u(I)
φ and ω scans	Rint = 0.139
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 25.1°, θmin = 3.0°
Tmin = 0.368, Tmax = 0.746	h = −14→14
31593 measured reflections	k = −11→11
3668 independent reflections	l = −29→29

Refinement

Refinement on F^2	41 constraints
Least-squares matrix: full	Primary atom site location: iterative
R[F^2 > 2σ(F^2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.184	w = 1/[σ^2(Fo^2) + (0.0846P)^2 + 0.3653P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
3668 reflections	Δρmax = 0.47 e Å^−3
278 parameters	Δρmin = −0.37 e Å^−3
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.73134 (18)	0.7445 (2)	0.43603 (9)	0.0355 (5)
O2	0.88916 (17)	0.7377 (2)	0.38033 (9)	0.0323 (5)
O3	0.83886 (19)	0.9615 (2)	0.50335 (9)	0.0400 (5)
N1	0.49557 (19)	0.2754 (2)	0.23347 (11)	0.0271 (5)
H1a	0.52980 (19)	0.2410 (2)	0.20230 (11)	0.0326 (7)*
N2	0.8603 (2)	1.1906 (2)	0.46049 (11)	0.0319 (6)
C1	0.7855 (2)	0.6922 (3)	0.39023 (13)	0.0271 (6)
C2	0.7105 (2)	0.5787 (3)	0.35193 (12)	0.0239 (6)
C3	0.7566 (2)	0.5171 (3)	0.30121 (12)	0.0262 (6)
H3	0.8380 (2)	0.5456 (3)	0.29315 (12)	0.0314 (7)*
C4	0.6864 (2)	0.4164 (3)	0.26299 (13)	0.0270 (6)
H4	0.7197 (2)	0.3763 (3)	0.22878 (13)	0.0324 (8)*
C5	0.5653 (2)	0.3715 (3)	0.27377 (12)	0.0242 (6)
C6	0.5206 (2)	0.4299 (3)	0.32576 (12)	0.0263 (6)
H6	0.4407 (2)	0.3988 (3)	0.33498 (12)	0.0316 (7)*
C7	0.5920 (2)	0.5320 (3)	0.36341 (12)	0.0251 (6)
H7	0.5597 (2)	0.5715 (3)	0.39801 (12)	0.0302 (7)*
C8	0.3682 (2)	0.2265 (3)	0.23901 (13)	0.0272 (6)
H8a	0.3697 (2)	0.1682 (3)	0.27751 (13)	0.0327 (8)*
H8b	0.3128 (2)	0.3149 (3)	0.24074 (13)	0.0327 (8)*
C9	0.3172 (2)	0.1300 (3)	0.18389 (12)	0.0234 (6)
C10	0.2375 (2)	0.1918 (3)	0.13285 (12)	0.0248 (6)
C11	0.1944 (3)	0.3436 (3)	0.13080 (14)	0.0344 (7)
H11	0.2224 (3)	0.4081 (3)	0.16466 (14)	0.0412 (9)*
C12	0.1145 (3)	0.3979 (4)	0.08172 (16)	0.0452 (8)
H12	0.0856 (3)	0.4987 (4)	0.08225 (16)	0.0543 (10)*
C13	0.0737 (3)	0.3074 (4)	0.03015 (16)	0.0456 (9)
H13	0.0174 (3)	0.3471 (4)	−0.00384 (16)	0.0548 (10)*
C14	0.1141 (3)	0.1640 (4)	0.02867 (14)	0.0372 (7)
H14	0.0880 (3)	0.1048 (4)	−0.00706 (14)	0.0447 (9)*
C15	0.1955 (2)	0.0998 (3)	0.07979 (12)	0.0282 (6)
C16	0.2339 (2)	−0.0494 (3)	0.07998 (13)	0.0289 (7)
H16	0.2064 (2)	−0.1097 (3)	0.04472 (13)	0.0347 (8)*
C17	0.3112 (2)	−0.1129 (3)	0.13030 (12)	0.0266 (6)
C18	0.3469 (3)	−0.2670 (3)	0.13064 (15)	0.0350 (7)
H18	0.3170 (3)	−0.3283 (3)	0.09599 (15)	0.0420 (9)*
C19	0.4230 (3)	−0.3272 (3)	0.17973 (16)	0.0407 (8)
H19	0.4447 (3)	−0.4306 (3)	0.17957 (16)	0.0489 (10)*
C20	0.4701 (3)	−0.2375 (3)	0.23099 (15)	0.0368 (7)
H20	0.5252 (3)	−0.2804 (3)	0.26469 (15)	0.0441 (9)*
C21	0.4378 (2)	−0.0896 (3)	0.23285 (13)	0.0306 (7)
H21	0.4707 (2)	−0.0312 (3)	0.26793 (13)	0.0367 (8)*
C22	0.3555 (2)	−0.0209 (3)	0.18322 (12)	0.0235 (6)
C23	0.8782 (3)	1.0922 (3)	0.50634 (14)	0.0318 (7)
H23	0.9249 (3)	1.1247 (3)	0.54448 (14)	0.0381 (8)*
C24	0.9129 (3)	1.3401 (3)	0.46883 (15)	0.0401 (8)
H24a	0.8440 (3)	1.4139 (3)	0.4638 (9)	0.0602 (12)*
H24b	0.9620 (16)	1.3491 (7)	0.5103 (3)	0.0602 (12)*
H24c	0.9684 (15)	1.3586 (9)	0.4381 (6)	0.0602 (12)*
C25	0.7882 (3)	1.1510 (4)	0.40096 (14)	0.0445 (8)
H25a	0.8462 (3)	1.136 (2)	0.3711 (3)	0.0668 (12)*
H25b	0.7411 (15)	1.0580 (13)	0.4049 (2)	0.0668 (12)*
H25c	0.7286 (14)	1.2320 (11)	0.3868 (5)	0.0668 (12)*
H1	0.776 (4)	0.836 (4)	0.4571 (18)	0.085 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0360 (12)	0.0387 (12)	0.0343 (12)	−0.0078 (9)	0.0132 (9)	−0.0087 (10)
O2	0.0293 (11)	0.0377 (11)	0.0307 (11)	−0.0076 (8)	0.0071 (9)	−0.0032 (9)
O3	0.0511 (13)	0.0329 (12)	0.0356 (13)	−0.0006 (9)	0.0058 (10)	−0.0041 (10)
N1	0.0206 (11)	0.0305 (12)	0.0311 (13)	−0.0044 (9)	0.0066 (10)	−0.0092 (10)
N2	0.0321 (13)	0.0264 (12)	0.0366 (15)	0.0015 (10)	0.0039 (11)	−0.0002 (11)
C1	0.0242 (15)	0.0293 (15)	0.0288 (16)	0.0008 (11)	0.0071 (12)	0.0040 (12)
C2	0.0220 (13)	0.0238 (13)	0.0260 (15)	0.0027 (10)	0.0043 (11)	0.0031 (11)
C3	0.0201 (13)	0.0254 (14)	0.0331 (16)	−0.0019 (10)	0.0045 (11)	0.0012 (12)
C4	0.0240 (14)	0.0272 (14)	0.0311 (16)	0.0007 (11)	0.0088 (11)	−0.0040 (12)
C5	0.0215 (13)	0.0230 (13)	0.0278 (15)	0.0016 (10)	0.0030 (11)	0.0018 (12)
C6	0.0199 (13)	0.0284 (14)	0.0316 (16)	0.0005 (11)	0.0070 (11)	0.0012 (12)
C7	0.0230 (14)	0.0275 (14)	0.0255 (15)	0.0017 (11)	0.0055 (11)	−0.0011 (12)
C8	0.0197 (14)	0.0317 (15)	0.0309 (16)	−0.0039 (11)	0.0060 (11)	−0.0039 (12)
C9	0.0166 (13)	0.0278 (14)	0.0267 (15)	−0.0037 (10)	0.0064 (11)	−0.0007 (12)
C10	0.0179 (13)	0.0265 (14)	0.0311 (16)	−0.0033 (10)	0.0075 (11)	0.0036 (12)
C11	0.0327 (16)	0.0330 (16)	0.0387 (18)	0.0027 (12)	0.0097 (13)	0.0042 (14)
C12	0.0374 (18)	0.0412 (18)	0.057 (2)	0.0063 (14)	0.0066 (16)	0.0160 (17)
C13	0.0301 (17)	0.058 (2)	0.047 (2)	0.0023 (15)	−0.0001 (15)	0.0250 (17)
C14	0.0266 (15)	0.0536 (19)	0.0307 (17)	−0.0107 (14)	0.0021 (13)	0.0099 (15)
C15	0.0212 (14)	0.0355 (15)	0.0284 (16)	−0.0060 (11)	0.0055 (11)	0.0037 (13)
C16	0.0240 (14)	0.0356 (16)	0.0281 (16)	−0.0089 (11)	0.0066 (12)	−0.0044 (13)
C17	0.0209 (13)	0.0284 (14)	0.0326 (16)	−0.0046 (11)	0.0106 (12)	−0.0013 (12)
C18	0.0336 (16)	0.0291 (15)	0.045 (2)	−0.0057 (12)	0.0159 (14)	−0.0033 (14)
C19	0.0361 (17)	0.0262 (15)	0.062 (2)	0.0008 (13)	0.0139 (16)	0.0051 (15)
C20	0.0260 (15)	0.0352 (16)	0.048 (2)	0.0010 (12)	0.0036 (14)	0.0132 (15)
C21	0.0217 (14)	0.0340 (15)	0.0358 (17)	−0.0047 (11)	0.0040 (12)	0.0039 (13)
C22	0.0168 (13)	0.0256 (13)	0.0290 (15)	−0.0029 (10)	0.0065 (11)	0.0027 (12)
C23	0.0307 (15)	0.0281 (15)	0.0360 (18)	0.0041 (12)	0.0036 (13)	−0.0066 (13)
C24	0.0380 (18)	0.0304 (16)	0.053 (2)	−0.0011 (13)	0.0099 (15)	0.0012 (15)
C25	0.047 (2)	0.049 (2)	0.0341 (18)	−0.0011 (15)	−0.0030 (15)	0.0005 (15)

Geometric parameters (Å, º)

O1—C1	1.322 (3)	C11—H11	0.9500
O1—H1	1.02 (4)	C11—C12	1.354 (4)
O2—C1	1.230 (3)	C12—H12	0.9500
O3—C23	1.236 (3)	C12—C13	1.402 (5)
N1—H1a	0.8800	C13—H13	0.9500
N1—C5	1.365 (3)	C13—C14	1.351 (4)
N1—C8	1.452 (3)	C14—H14	0.9500
N2—C23	1.326 (4)	C14—C15	1.427 (4)
N2—C24	1.446 (3)	C15—C16	1.391 (4)
N2—C25	1.452 (4)	C16—H16	0.9500
C1—C2	1.470 (4)	C16—C17	1.392 (4)
C2—C3	1.399 (4)	C17—C18	1.424 (4)
C2—C7	1.393 (3)	C17—C22	1.439 (4)
C3—H3	0.9500	C18—H18	0.9500
C3—C4	1.368 (4)	C18—C19	1.355 (4)
C4—H4	0.9500	C19—H19	0.9500
C4—C5	1.410 (3)	C19—C20	1.407 (4)
C5—C6	1.405 (4)	C20—H20	0.9500
C6—H6	0.9500	C20—C21	1.365 (4)
C6—C7	1.376 (4)	C21—H21	0.9500
C7—H7	0.9500	C21—C22	1.426 (4)
C8—H8a	0.9900	C23—H23	0.9500
C8—H8b	0.9900	C24—H24a	0.9800
C8—C9	1.514 (4)	C24—H24b	0.9800
C9—C10	1.408 (4)	C24—H24c	0.9800
C9—C22	1.406 (3)	C25—H25a	0.9800
C10—C11	1.427 (4)	C25—H25b	0.9800
C10—C15	1.437 (4)	C25—H25c	0.9800
H1—O1—C1	114 (2)	H13—C13—C12	119.91 (18)
C5—N1—H1a	118.07 (14)	C14—C13—C12	120.2 (3)
C8—N1—H1a	118.07 (14)	C14—C13—H13	119.91 (19)
C8—N1—C5	123.9 (2)	H14—C14—C13	119.40 (19)
C24—N2—C23	120.4 (2)	C15—C14—C13	121.2 (3)
C25—N2—C23	121.1 (2)	C15—C14—H14	119.40 (18)
C25—N2—C24	118.6 (2)	C14—C15—C10	118.9 (3)
O2—C1—O1	122.2 (3)	C16—C15—C10	119.2 (2)
C2—C1—O1	114.4 (2)	C16—C15—C14	121.9 (3)
C2—C1—O2	123.4 (2)	H16—C16—C15	119.03 (16)
C3—C2—C1	119.8 (2)	C17—C16—C15	121.9 (2)
C7—C2—C1	122.1 (2)	C17—C16—H16	119.03 (16)
C7—C2—C3	118.1 (2)	C18—C17—C16	121.4 (3)
H3—C3—C2	119.41 (15)	C22—C17—C16	119.2 (2)
C4—C3—C2	121.2 (2)	C22—C17—C18	119.4 (2)
C4—C3—H3	119.41 (16)	H18—C18—C17	119.59 (17)
H4—C4—C3	119.59 (16)	C19—C18—C17	120.8 (3)
C5—C4—C3	120.8 (2)	C19—C18—H18	119.59 (17)
C5—C4—H4	119.59 (15)	H19—C19—C18	119.81 (17)
C4—C5—N1	119.4 (2)	C20—C19—C18	120.4 (3)
C6—C5—N1	122.6 (2)	C20—C19—H19	119.81 (17)
C6—C5—C4	118.0 (2)	H20—C20—C19	119.60 (17)
H6—C6—C5	119.79 (15)	C21—C20—C19	120.8 (3)
C7—C6—C5	120.4 (2)	C21—C20—H20	119.60 (18)
C7—C6—H6	119.79 (15)	H21—C21—C20	119.32 (18)
C6—C7—C2	121.5 (2)	C22—C21—C20	121.4 (3)
H7—C7—C2	119.26 (15)	C22—C21—H21	119.32 (16)
H7—C7—C6	119.26 (15)	C17—C22—C9	119.6 (2)
H8a—C8—N1	109.85 (14)	C21—C22—C9	123.2 (2)
H8b—C8—N1	109.85 (14)	C21—C22—C17	117.2 (2)
H8b—C8—H8a	108.3	N2—C23—O3	125.1 (3)
C9—C8—N1	109.2 (2)	H23—C23—O3	117.46 (17)
C9—C8—H8a	109.85 (14)	H23—C23—N2	117.46 (16)
C9—C8—H8b	109.85 (14)	H24a—C24—N2	109.5
C10—C9—C8	120.7 (2)	H24b—C24—N2	109.5
C22—C9—C8	118.8 (2)	H24b—C24—H24a	109.5
C22—C9—C10	120.4 (2)	H24c—C24—N2	109.5
C11—C10—C9	123.2 (2)	H24c—C24—H24a	109.5
C15—C10—C9	119.7 (2)	H24c—C24—H24b	109.5
C15—C10—C11	117.2 (2)	H25a—C25—N2	109.5
H11—C11—C10	119.22 (16)	H25b—C25—N2	109.5
C12—C11—C10	121.6 (3)	H25b—C25—H25a	109.5
C12—C11—H11	119.22 (19)	H25c—C25—N2	109.5
H12—C12—C11	119.52 (19)	H25c—C25—H25a	109.5
C13—C12—C11	121.0 (3)	H25c—C25—H25b	109.5
C13—C12—H12	119.52 (18)

Hydrogen-bond geometry (Å, º)

Cg5 and Cg7 are the centroids of the 10-membered ring system C9–C22 and of the 14-membered anthracene moiety, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	1.02 (4)	1.59 (4)	2.590 (3)	167 (4)
N1—H1A···O2^i	0.88 (1)	2.13 (1)	2.973 (3)	160 (1)
C18—H18···O3^ii	0.95 (1)	2.40 (1)	3.277 (4)	154 (1)
C6—H6···Cg7^iii	0.95	2.80 (1)	3.552 (2)	137 (1)
C7—H7···Cg5^iii	0.95	2.99 (1)	3.646 (3)	138 (1)

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