1-(2,4-Dihydroxy­phen­yl)ethanone [(1H-indol-3-yl)acet­yl]hydrazone–2-(1H-indol-3-yl)acetohydrazide (1/1)

The two components of the title cocrystal, C₁₀H₁₀N₃O·C₁₈H₁₈N₃O₃, are linked by a hydrazine–hydr­oxy N—H...O hydrogen bond; an inter­molecular amide–amide N—H...O inter­action that involves only the hydrazide component leads to the formation of a linear chain structure. Further inter­molecular O—H...O and N—H...O hydrogen bonds form a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.047
• wR factor = 0.147
• Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H3N1   ..  H4O     ..       2.01 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.45
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.27
PLAT414_ALERT_2_C Short Intra D-H..H-X       H5N    ..  H22A    ..       1.94 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N3     -   H3N1   ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1N    ...          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

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           27.50
           From the CIF: _reflns_number_total               2770
           Count of symmetry unique reflns         2790
           Completeness (_total/calc)             99.28%
           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
   1 ALERT level B = Potentially serious problem
   8 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
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

1-(2,4-Dihydroxyphenyl)ethanone [(1H-indol-3-yl)acetyl]hydrazone– 2-(1H-indol-3-yl)acetohydrazide (1/1)

Crystal data

C10H10N3O·C18H18N3O3	F(000) = 1080
Mr = 512.56	Dx = 1.412 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 7984 reflections
a = 49.2086 (6) Å	θ = 2.5–34.2°
b = 5.0292 (1) Å	µ = 0.10 mm^−1
c = 9.8401 (1) Å	T = 173 K
β = 98.186 (1)°	Block, yellow
V = 2410.41 (6) Å^3	0.50 × 0.50 × 0.50 mm
Z = 4

Data collection

Bruker APEXII diffractometer	2726 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 27.5°, θmin = 0.8°
φ and ω scans	h = −63→61
16582 measured reflections	k = −6→6
2770 independent reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1185P)^2 + 1.5332P] where P = (Fo^2 + 2Fc^2)/3
2770 reflections	(Δ/σ)max = 0.001
344 parameters	Δρmax = 0.49 e Å^−3
2 restraints	Δρmin = −0.44 e Å^−3

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

	x	y	z	Uiso*/Ueq
O1	0.49998 (5)	0.5710 (5)	0.7500 (3)	0.0281 (5)
O2	0.29683 (5)	0.2106 (4)	0.1002 (2)	0.0238 (5)
O3	0.36512 (5)	0.0810 (4)	0.3027 (2)	0.0238 (5)
H3O	0.3504	0.0437	0.2522	0.029*
O4	0.45568 (5)	−0.2371 (5)	0.4311 (3)	0.0287 (5)
H4o	0.4623	−0.3909	0.4411	0.034*
N1	0.58376 (6)	0.5642 (5)	1.0190 (3)	0.0243 (5)
H1N	0.5933	0.6853	1.0698	0.029*
N2	0.49390 (6)	0.1523 (5)	0.6672 (3)	0.0250 (5)
H2N	0.4986	−0.0160	0.6783	0.030*
N3	0.47616 (6)	0.2295 (6)	0.5467 (3)	0.0270 (6)
H3n	0.4662	0.0923	0.5143	0.032*
H3n1	0.4860	0.2856	0.4845	0.032*
N4	0.25631 (6)	0.4740 (5)	−0.2940 (3)	0.0234 (5)
H4N	0.2632	0.5988	−0.3417	0.028*
N5	0.30807 (5)	−0.2086 (5)	0.0457 (3)	0.0201 (5)
H5n	0.3035	−0.3546	−0.0015	0.024*
N6	0.33380 (5)	−0.1793 (5)	0.1220 (3)	0.0206 (5)
C1	0.59425 (7)	0.3896 (6)	0.9322 (3)	0.0225 (6)
C2	0.62102 (7)	0.3586 (7)	0.9048 (3)	0.0266 (6)
H2	0.6354	0.4710	0.9455	0.032*
C3	0.62568 (7)	0.1558 (7)	0.8153 (4)	0.0287 (7)
H3	0.6437	0.1287	0.7938	0.034*
C4	0.60430 (8)	−0.0102 (7)	0.7558 (3)	0.0289 (7)
H4	0.6082	−0.1488	0.6960	0.035*
C5	0.57759 (7)	0.0233 (6)	0.7823 (3)	0.0239 (6)
H5	0.5632	−0.0892	0.7409	0.029*
C6	0.57232 (6)	0.2280 (6)	0.8719 (3)	0.0202 (6)
C7	0.54807 (6)	0.3167 (6)	0.9259 (3)	0.0214 (6)
C8	0.55625 (7)	0.5205 (6)	1.0141 (3)	0.0231 (6)
H8	0.5445	0.6176	1.0647	0.028*
C9	0.51969 (7)	0.2063 (6)	0.8930 (3)	0.0240 (6)
H9A	0.5096	0.2382	0.9717	0.029*
H9B	0.5208	0.0116	0.8800	0.029*
C10	0.50367 (6)	0.3291 (6)	0.7645 (3)	0.0221 (6)
C11	0.22908 (7)	0.4071 (6)	−0.3044 (3)	0.0215 (6)
C12	0.20624 (7)	0.5057 (6)	−0.3907 (3)	0.0262 (6)
H12	0.2080	0.6443	−0.4545	0.031*
C13	0.18113 (7)	0.3932 (7)	−0.3795 (4)	0.0290 (7)
H13	0.1652	0.4583	−0.4358	0.035*
C14	0.17834 (7)	0.1840 (7)	−0.2866 (4)	0.0272 (7)
H14	0.1607	0.1101	−0.2824	0.033*
C15	0.20086 (6)	0.0855 (6)	−0.2019 (3)	0.0237 (6)
H15	0.1989	−0.0552	−0.1396	0.028*
C16	0.22670 (6)	0.1981 (6)	−0.2100 (3)	0.0199 (6)
C17	0.25395 (6)	0.1454 (6)	−0.1408 (3)	0.0207 (6)
C18	0.27114 (7)	0.3144 (6)	−0.1969 (3)	0.0220 (6)
H18	0.2905	0.3205	−0.1723	0.026*
C19	0.26151 (6)	−0.0561 (6)	−0.0286 (3)	0.0205 (6)
H19A	0.2607	−0.2368	−0.0689	0.025*
H19B	0.2481	−0.0474	0.0374	0.025*
C20	0.29013 (6)	−0.0049 (6)	0.0463 (3)	0.0195 (6)
C21	0.35351 (6)	−0.3331 (5)	0.0933 (3)	0.0183 (5)
C22	0.35021 (6)	−0.5367 (6)	−0.0187 (3)	0.0218 (6)
H22A	0.3340	−0.4939	−0.0851	0.033*
H22B	0.3479	−0.7128	0.0207	0.033*
H22C	0.3666	−0.5367	−0.0651	0.033*
C23	0.38022 (6)	−0.2960 (6)	0.1788 (3)	0.0183 (5)
C24	0.38470 (6)	−0.0927 (6)	0.2794 (3)	0.0200 (6)
C25	0.41000 (7)	−0.0682 (6)	0.3625 (3)	0.0227 (6)
H25	0.4129	0.0704	0.4286	0.027*
C26	0.43099 (6)	−0.2475 (6)	0.3484 (4)	0.0230 (6)
C27	0.42697 (6)	−0.4506 (6)	0.2506 (3)	0.0227 (6)
H27	0.4413	−0.5729	0.2413	0.027*
C28	0.40207 (6)	−0.4719 (6)	0.1679 (3)	0.0211 (6)
H28	0.3995	−0.6097	0.1012	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0298 (12)	0.0107 (10)	0.0417 (13)	0.0001 (8)	−0.0028 (9)	0.0000 (9)
O2	0.0214 (10)	0.0105 (9)	0.0392 (12)	0.0005 (8)	0.0030 (8)	−0.0044 (8)
O3	0.0222 (10)	0.0123 (10)	0.0367 (12)	0.0024 (8)	0.0035 (8)	−0.0027 (8)
O4	0.0224 (11)	0.0150 (11)	0.0462 (14)	0.0008 (9)	−0.0032 (9)	0.0003 (10)
N1	0.0261 (13)	0.0142 (12)	0.0316 (13)	−0.0008 (10)	−0.0002 (10)	−0.0035 (10)
N2	0.0266 (13)	0.0117 (11)	0.0353 (14)	0.0021 (10)	−0.0001 (10)	−0.0002 (10)
N3	0.0287 (14)	0.0159 (12)	0.0343 (14)	0.0015 (10)	−0.0031 (11)	−0.0006 (10)
N4	0.0265 (13)	0.0136 (11)	0.0304 (13)	−0.0023 (10)	0.0048 (10)	−0.0014 (10)
N5	0.0196 (12)	0.0117 (11)	0.0287 (12)	0.0007 (9)	0.0023 (9)	−0.0023 (9)
N6	0.0177 (11)	0.0131 (11)	0.0305 (13)	0.0010 (9)	0.0018 (9)	−0.0004 (10)
C1	0.0271 (15)	0.0128 (13)	0.0265 (14)	0.0005 (11)	−0.0003 (11)	0.0006 (11)
C2	0.0264 (16)	0.0192 (15)	0.0336 (16)	0.0018 (12)	0.0022 (12)	0.0044 (12)
C3	0.0305 (16)	0.0234 (16)	0.0331 (17)	0.0075 (13)	0.0073 (12)	0.0066 (13)
C4	0.0425 (19)	0.0180 (14)	0.0267 (15)	0.0099 (13)	0.0066 (13)	0.0008 (12)
C5	0.0326 (16)	0.0135 (13)	0.0243 (13)	0.0020 (12)	−0.0004 (11)	0.0015 (11)
C6	0.0240 (14)	0.0121 (12)	0.0238 (13)	0.0012 (11)	0.0009 (10)	0.0019 (11)
C7	0.0240 (14)	0.0121 (13)	0.0276 (14)	0.0010 (11)	0.0017 (11)	0.0012 (11)
C8	0.0267 (15)	0.0165 (13)	0.0258 (14)	0.0008 (11)	0.0023 (11)	0.0000 (11)
C9	0.0231 (14)	0.0150 (14)	0.0334 (16)	−0.0013 (11)	0.0021 (11)	0.0028 (11)
C10	0.0180 (13)	0.0133 (13)	0.0350 (16)	−0.0003 (10)	0.0041 (11)	0.0023 (11)
C11	0.0253 (14)	0.0122 (12)	0.0273 (14)	−0.0015 (10)	0.0049 (11)	−0.0031 (10)
C12	0.0308 (16)	0.0157 (14)	0.0321 (15)	0.0037 (12)	0.0049 (12)	−0.0007 (12)
C13	0.0258 (15)	0.0254 (16)	0.0348 (16)	0.0056 (12)	0.0011 (12)	−0.0021 (13)
C14	0.0217 (14)	0.0212 (15)	0.0388 (18)	−0.0003 (11)	0.0050 (12)	−0.0041 (13)
C15	0.0202 (13)	0.0180 (14)	0.0335 (15)	−0.0002 (11)	0.0059 (11)	0.0003 (11)
C16	0.0228 (14)	0.0100 (12)	0.0270 (14)	0.0027 (10)	0.0036 (11)	−0.0033 (10)
C17	0.0187 (13)	0.0114 (12)	0.0322 (15)	0.0009 (10)	0.0040 (10)	−0.0033 (11)
C18	0.0241 (14)	0.0154 (13)	0.0269 (14)	−0.0021 (11)	0.0046 (11)	−0.0028 (10)
C19	0.0178 (13)	0.0124 (13)	0.0312 (15)	−0.0002 (9)	0.0029 (11)	−0.0006 (10)
C20	0.0191 (13)	0.0116 (13)	0.0279 (14)	0.0016 (10)	0.0039 (10)	0.0017 (10)
C21	0.0214 (13)	0.0072 (12)	0.0272 (14)	−0.0003 (10)	0.0061 (10)	0.0019 (10)
C22	0.0232 (14)	0.0127 (12)	0.0301 (15)	0.0005 (10)	0.0059 (11)	−0.0014 (10)
C23	0.0199 (13)	0.0088 (12)	0.0266 (13)	−0.0006 (9)	0.0045 (10)	0.0010 (10)
C24	0.0203 (13)	0.0112 (12)	0.0293 (14)	−0.0020 (10)	0.0066 (11)	0.0008 (11)
C25	0.0247 (14)	0.0116 (12)	0.0317 (14)	−0.0021 (11)	0.0037 (11)	0.0002 (11)
C26	0.0214 (14)	0.0119 (13)	0.0356 (16)	−0.0019 (11)	0.0037 (11)	0.0028 (11)
C27	0.0192 (13)	0.0129 (13)	0.0365 (16)	0.0023 (10)	0.0059 (11)	0.0002 (11)
C28	0.0219 (13)	0.0122 (13)	0.0299 (15)	−0.0011 (10)	0.0057 (11)	−0.0021 (10)

Geometric parameters (Å, º)

O1—C10	1.236 (4)	C9—C10	1.522 (4)
O2—C20	1.231 (4)	C9—H9A	0.9900
O3—C24	1.344 (4)	C9—H9B	0.9900
O3—H3O	0.8400	C11—C12	1.400 (5)
O4—C26	1.364 (4)	C11—C16	1.418 (4)
O4—H4O	0.8400	C12—C13	1.378 (5)
N1—C8	1.366 (4)	C12—H12	0.9500
N1—C1	1.376 (4)	C13—C14	1.413 (5)
N1—H1N	0.8800	C13—H13	0.9500
N2—C10	1.345 (4)	C14—C15	1.380 (5)
N2—N3	1.422 (4)	C14—H14	0.9500
N2—H2N	0.8800	C15—C16	1.404 (4)
N3—H3n	0.8800	C15—H15	0.9500
N3—H3n1	0.8800	C16—C17	1.439 (4)
N4—C11	1.371 (4)	C17—C18	1.370 (4)
N4—C18	1.375 (4)	C17—C19	1.505 (4)
N4—H4N	0.8800	C18—H18	0.9500
N5—C20	1.353 (4)	C19—C20	1.516 (4)
N5—N6	1.385 (3)	C19—H19A	0.9900
N5—H5n	0.8800	C19—H19B	0.9900
N6—C21	1.303 (4)	C21—C23	1.468 (4)
C1—C2	1.390 (5)	C21—C22	1.496 (4)
C1—C6	1.412 (4)	C22—H22A	0.9800
C2—C3	1.388 (5)	C22—H22B	0.9800
C2—H2	0.9500	C22—H22C	0.9800
C3—C4	1.404 (5)	C23—C28	1.408 (4)
C3—H3	0.9500	C23—C24	1.418 (4)
C4—C5	1.386 (5)	C24—C25	1.394 (4)
C4—H4	0.9500	C25—C26	1.393 (4)
C5—C6	1.404 (4)	C25—H25	0.9500
C5—H5	0.9500	C26—C27	1.398 (4)
C6—C7	1.444 (4)	C27—C28	1.375 (4)
C7—C8	1.366 (4)	C27—H27	0.9500
C7—C9	1.495 (4)	C28—H28	0.9500
C8—H8	0.9500
C24—O3—H3O	109.5	C11—C12—H12	121.4
C26—O4—H4O	109.5	C12—C13—C14	121.9 (3)
C8—N1—C1	109.5 (3)	C12—C13—H13	119.0
C8—N1—H1N	125.3	C14—C13—H13	119.0
C1—N1—H1N	125.3	C15—C14—C13	120.9 (3)
C10—N2—N3	121.9 (3)	C15—C14—H14	119.5
C10—N2—H2N	119.1	C13—C14—H14	119.5
N3—N2—H2N	119.1	C14—C15—C16	118.5 (3)
N2—N3—H3n	109.5	C14—C15—H15	120.8
N2—N3—H3n1	109.5	C16—C15—H15	120.8
H3n—N3—H3n1	109.5	C15—C16—C11	119.7 (3)
C11—N4—C18	109.0 (3)	C15—C16—C17	133.5 (3)
C11—N4—H4N	125.5	C11—C16—C17	106.7 (3)
C18—N4—H4N	125.5	C18—C17—C16	106.4 (3)
C20—N5—N6	117.6 (2)	C18—C17—C19	127.6 (3)
C20—N5—H5	121.2	C16—C17—C19	126.0 (3)
N6—N5—H5n	121.2	C17—C18—N4	110.2 (3)
C21—N6—N5	118.1 (3)	C17—C18—H18	124.9
N1—C1—C2	129.9 (3)	N4—C18—H18	124.9
N1—C1—C6	107.2 (3)	C17—C19—C20	111.0 (2)
C2—C1—C6	122.8 (3)	C17—C19—H19A	109.4
C3—C2—C1	116.9 (3)	C20—C19—H19A	109.4
C3—C2—H2	121.5	C17—C19—H19B	109.4
C1—C2—H2	121.5	C20—C19—H19B	109.4
C2—C3—C4	121.3 (3)	H19A—C19—H19B	108.0
C2—C3—H3	119.4	O2—C20—N5	122.3 (3)
C4—C3—H3	119.4	O2—C20—C19	122.2 (3)
C5—C4—C3	121.6 (3)	N5—C20—C19	115.5 (3)
C5—C4—H4	119.2	N6—C21—C23	115.7 (3)
C3—C4—H4	119.2	N6—C21—C22	124.1 (3)
C4—C5—C6	118.2 (3)	C23—C21—C22	120.2 (2)
C4—C5—H5	120.9	C21—C22—H22A	109.5
C6—C5—H5	120.9	C21—C22—H22B	109.5
C5—C6—C1	119.2 (3)	H22A—C22—H22B	109.5
C5—C6—C7	133.9 (3)	C21—C22—H22C	109.5
C1—C6—C7	106.8 (3)	H22A—C22—H22C	109.5
C8—C7—C6	106.3 (3)	H22B—C22—H22C	109.5
C8—C7—C9	126.7 (3)	C28—C23—C24	117.5 (3)
C6—C7—C9	127.0 (3)	C28—C23—C21	120.5 (3)
N1—C8—C7	110.1 (3)	C24—C23—C21	121.9 (3)
N1—C8—H8	124.9	O3—C24—C25	116.4 (3)
C7—C8—H8	124.9	O3—C24—C23	122.9 (3)
C7—C9—C10	112.7 (3)	C25—C24—C23	120.7 (3)
C7—C9—H9A	109.0	C26—C25—C24	119.8 (3)
C10—C9—H9A	109.0	C26—C25—H25	120.1
C7—C9—H9B	109.0	C24—C25—H25	120.1
C10—C9—H9B	109.0	O4—C26—C25	121.7 (3)
H9A—C9—H9B	107.8	O4—C26—C27	117.8 (3)
O1—C10—N2	122.5 (3)	C25—C26—C27	120.5 (3)
O1—C10—C9	123.1 (3)	C28—C27—C26	119.4 (3)
N2—C10—C9	114.4 (3)	C28—C27—H27	120.3
N4—C11—C12	130.5 (3)	C26—C27—H27	120.3
N4—C11—C16	107.7 (3)	C27—C28—C23	122.1 (3)
C12—C11—C16	121.8 (3)	C27—C28—H28	119.0
C13—C12—C11	117.2 (3)	C23—C28—H28	119.0
C13—C12—H12	121.4
C20—N5—N6—C21	−160.9 (3)	N4—C11—C16—C15	−178.3 (3)
C8—N1—C1—C2	−179.3 (3)	C12—C11—C16—C15	0.0 (4)
C8—N1—C1—C6	−0.7 (4)	N4—C11—C16—C17	0.8 (3)
N1—C1—C2—C3	177.5 (3)	C12—C11—C16—C17	179.0 (3)
C6—C1—C2—C3	−0.9 (5)	C15—C16—C17—C18	177.4 (3)
C1—C2—C3—C4	−0.2 (5)	C11—C16—C17—C18	−1.5 (3)
C2—C3—C4—C5	0.9 (5)	C15—C16—C17—C19	−2.8 (5)
C3—C4—C5—C6	−0.5 (5)	C11—C16—C17—C19	178.3 (3)
C4—C5—C6—C1	−0.5 (4)	C16—C17—C18—N4	1.6 (3)
C4—C5—C6—C7	−177.9 (3)	C19—C17—C18—N4	−178.1 (3)
N1—C1—C6—C5	−177.4 (3)	C11—N4—C18—C17	−1.1 (3)
C2—C1—C6—C5	1.3 (5)	C18—C17—C19—C20	15.5 (4)
N1—C1—C6—C7	0.6 (3)	C16—C17—C19—C20	−164.1 (3)
C2—C1—C6—C7	179.3 (3)	N6—N5—C20—O2	7.4 (4)
C5—C6—C7—C8	177.3 (3)	N6—N5—C20—C19	−175.0 (2)
C1—C6—C7—C8	−0.3 (3)	C17—C19—C20—O2	55.8 (4)
C5—C6—C7—C9	−2.2 (6)	C17—C19—C20—N5	−121.9 (3)
C1—C6—C7—C9	−179.8 (3)	N5—N6—C21—C23	−179.1 (2)
C1—N1—C8—C7	0.5 (4)	N5—N6—C21—C22	1.1 (4)
C6—C7—C8—N1	−0.1 (3)	N6—C21—C23—C28	172.4 (3)
C9—C7—C8—N1	179.4 (3)	C22—C21—C23—C28	−7.8 (4)
C8—C7—C9—C10	94.9 (4)	N6—C21—C23—C24	−4.4 (4)
C6—C7—C9—C10	−85.7 (4)	C22—C21—C23—C24	175.4 (3)
N3—N2—C10—O1	−6.8 (5)	C28—C23—C24—O3	−177.6 (3)
N3—N2—C10—C9	173.5 (3)	C21—C23—C24—O3	−0.7 (4)
C7—C9—C10—O1	−55.8 (4)	C28—C23—C24—C25	0.8 (4)
C7—C9—C10—N2	123.9 (3)	C21—C23—C24—C25	177.7 (3)
C18—N4—C11—C12	−177.9 (3)	O3—C24—C25—C26	177.5 (3)
C18—N4—C11—C16	0.2 (3)	C23—C24—C25—C26	−1.0 (4)
N4—C11—C12—C13	178.5 (3)	C24—C25—C26—O4	−177.4 (3)
C16—C11—C12—C13	0.7 (5)	C24—C25—C26—C27	0.6 (5)
C11—C12—C13—C14	−1.0 (5)	O4—C26—C27—C28	178.2 (3)
C12—C13—C14—C15	0.7 (5)	C25—C26—C27—C28	0.2 (5)
C13—C14—C15—C16	0.0 (5)	C26—C27—C28—C23	−0.4 (5)
C14—C15—C16—C11	−0.3 (4)	C24—C23—C28—C27	0.0 (4)
C14—C15—C16—C17	−179.1 (3)	C21—C23—C28—C27	−177.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···N6	0.84	1.81	2.544 (3)	145
O4—H4o···N3^i	0.84	2.23	3.030 (4)	158
N2—H2n···O1^i	0.88	2.19	3.038 (4)	161
N3—H3n···O4	0.88	1.89	2.737 (4)	162
N4—H4n···O2^ii	0.88	2.06	2.858 (4)	150
N5—H5n···O2^i	0.88	2.45	3.034 (4)	125

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