1,5-Dianilinopentane-1,3,5-trione: a crystal structure containing two polymorphic domains

Single crystals of the title compound, C₁₇H₁₆N₂O₃, were obtained by gas diffusion. The observed diffraction pattern is compatible with a superposition of reflections from two monoclinic unit cells with the space group C2/c. The two cells share the a and b axes but not the c axis. Both structures contain layers parallel to (001), with mol­ecules connected by inter­molecular N—H...O=C hydrogen bonds. The bonding between adjacent layers is weak. Layer displacements result in a crystal structure containing two closely related polymorphic domains. The structure of one polymorph can be derived from the structure of the other if subsequent layers are displaced by (a/4, b/4, 0) for odd-numbered layers and by (a/4, −b/4, 0) for even-numbered layers. Three different crystals were analysed and their observed diffraction patterns were similar, showing all three crystals to contain the polymorphic domain structure.

Computing details

For both compounds, data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

(Ia) 1,5-dianilinopentane-1,3,5-trione

Crystal data

C17H16N2O3	F(000) = 2496
Mr = 296.32	Dx = 1.382 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6859 reflections
a = 17.6547 (5) Å	θ = 2–30°
b = 9.8640 (3) Å	µ = 0.10 mm^−1
c = 33.3982 (8) Å	T = 167 K
β = 101.560 (1)°	Rod, colourless
V = 5698.2 (3) Å^3	0.60 × 0.16 × 0.16 mm
Z = 16

Data collection

Siemens SMART 1K CCD area-detector diffractometer	8099 independent reflections
Radiation source: normal-focus sealed tube	1972 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.141
ω scans	θmax = 30.3°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −24→24
Tmin = 0.924, Tmax = 0.985	k = −13→13
41943 measured reflections	l = −45→46

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 0.81	w = 1/[σ^2(Fo^2) + (0.02P)^2] where P = (Fo^2 + 2Fc^2)/3
8099 reflections	(Δ/σ)max = 0.001
399 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.21641 (17)	0.7450 (3)	0.32204 (8)	0.0294 (8)
O2	0.24719 (16)	0.9561 (4)	0.24934 (8)	0.0362 (10)
O3	0.28291 (16)	0.7381 (3)	0.17972 (8)	0.0267 (8)
O4	0.03306 (17)	0.4879 (3)	0.17941 (8)	0.0267 (8)
O5	0.0000	0.7064 (5)	0.2500	0.0401 (14)
O6	0.03276 (17)	−0.0039 (3)	0.17832 (9)	0.0329 (9)
O7	0.0000	0.2074 (5)	0.2500	0.0436 (14)
N1	0.3286 (2)	0.6244 (4)	0.34101 (11)	0.0225 (9)
H1A	0.3693	0.5949	0.3322	0.027*
N2	0.1693 (2)	0.6213 (4)	0.15975 (10)	0.0221 (9)
H2B	0.1282	0.5930	0.1685	0.027*
N3	−0.0801 (2)	0.3718 (4)	0.15989 (10)	0.0204 (9)
H3B	−0.1206	0.3415	0.1688	0.024*
N4	−0.0777 (2)	−0.1256 (4)	0.15923 (11)	0.0226 (9)
H4B	−0.1181	−0.1566	0.1681	0.027*
C1	0.3203 (3)	0.5815 (5)	0.38029 (13)	0.0201 (11)
C2	0.2928 (2)	0.6685 (4)	0.40690 (11)	0.0250 (9)
H2A	0.2747	0.7563	0.3980	0.030*
C3	0.2920 (2)	0.6265 (4)	0.44667 (11)	0.0280 (10)
H3A	0.2738	0.6862	0.4650	0.034*
C4	0.3177 (3)	0.4979 (5)	0.45959 (13)	0.0290 (12)
H4A	0.3171	0.4696	0.4867	0.035*
C5	0.3440 (2)	0.4110 (4)	0.43300 (11)	0.0266 (10)
H5A	0.3610	0.3225	0.4417	0.032*
C6	0.3455 (2)	0.4534 (4)	0.39343 (11)	0.0242 (10)
H6A	0.3641	0.3937	0.3753	0.029*
C7	0.2804 (2)	0.7052 (4)	0.31631 (12)	0.0181 (10)
C8	0.3105 (3)	0.7590 (4)	0.27905 (12)	0.0241 (11)
H8A	0.3540	0.8223	0.2884	0.029*
H8B	0.3302	0.6823	0.2649	0.029*
C9	0.2480 (2)	0.8304 (6)	0.24989 (13)	0.0277 (13)
C10	0.1872 (2)	0.7520 (4)	0.22182 (12)	0.0203 (11)
H10A	0.1417	0.8106	0.2123	0.024*
H10B	0.1706	0.6742	0.2367	0.024*
C11	0.2185 (2)	0.7001 (4)	0.18480 (12)	0.0178 (10)
C12	0.1771 (3)	0.5783 (4)	0.12001 (13)	0.0209 (11)
C13	0.2486 (2)	0.5500 (4)	0.11017 (11)	0.0234 (9)
H13A	0.2949	0.5567	0.1303	0.028*
C14	0.2511 (2)	0.5117 (4)	0.07036 (11)	0.0262 (9)
H14A	0.2995	0.4941	0.0631	0.031*
C15	0.1835 (3)	0.4990 (5)	0.04112 (14)	0.0316 (13)
H15A	0.1857	0.4717	0.0141	0.038*
C16	0.1130 (2)	0.5262 (4)	0.05121 (12)	0.0278 (10)
H16A	0.0668	0.5184	0.0311	0.033*
C17	0.1096 (2)	0.5648 (4)	0.09077 (11)	0.0254 (9)
H17A	0.0609	0.5821	0.0978	0.031*
C18	−0.0726 (3)	0.3286 (5)	0.12000 (14)	0.0217 (11)
C19	−0.0021 (2)	0.2994 (4)	0.10977 (11)	0.0238 (9)
H19A	0.0444	0.3062	0.1297	0.029*
C20	−0.0002 (2)	0.2599 (4)	0.07002 (12)	0.0281 (10)
H20A	0.0480	0.2393	0.0630	0.034*
C21	−0.0672 (3)	0.2501 (5)	0.04049 (14)	0.0282 (12)
H21A	−0.0652	0.2251	0.0133	0.034*
C22	−0.1369 (2)	0.2771 (4)	0.05136 (12)	0.0303 (10)
H22A	−0.1834	0.2685	0.0315	0.036*
C23	−0.1404 (2)	0.3167 (4)	0.09076 (12)	0.0271 (10)
H23A	−0.1889	0.3356	0.0978	0.032*
C24	−0.0310 (3)	0.4553 (4)	0.18581 (14)	0.0231 (11)
C25	−0.0616 (2)	0.5029 (4)	0.22170 (12)	0.0216 (11)
H25A	−0.0769	0.4240	0.2366	0.026*
H25B	−0.1080	0.5597	0.2124	0.026*
C26	0.0000	0.5849 (7)	0.2500	0.0180 (15)
C27	−0.0699 (2)	−0.1705 (5)	0.11971 (13)	0.0193 (11)
C28	−0.0426 (2)	−0.0820 (4)	0.09313 (11)	0.0255 (10)
H28A	−0.0250	0.0061	0.1020	0.031*
C29	−0.0416 (2)	−0.1244 (4)	0.05369 (12)	0.0290 (10)
H29A	−0.0230	−0.0645	0.0356	0.035*
C30	−0.0671 (3)	−0.2513 (5)	0.04024 (13)	0.0275 (12)
H30A	−0.0661	−0.2790	0.0131	0.033*
C31	−0.0941 (2)	−0.3382 (4)	0.06674 (12)	0.0301 (10)
H31A	−0.1118	−0.4260	0.0576	0.036*
C32	−0.0957 (2)	−0.2987 (4)	0.10653 (12)	0.0252 (10)
H32A	−0.1144	−0.3590	0.1245	0.030*
C33	−0.0300 (3)	−0.0403 (4)	0.18496 (14)	0.0248 (11)
C34	−0.0612 (2)	0.0050 (4)	0.22110 (12)	0.0230 (11)
H34A	−0.0761	−0.0750	0.2357	0.028*
H34B	−0.1078	0.0613	0.2119	0.028*
C35	0.0000	0.0871 (7)	0.2500	0.0169 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0227 (19)	0.042 (2)	0.0263 (18)	0.0105 (16)	0.0105 (14)	0.0027 (16)
O2	0.048 (3)	0.021 (2)	0.036 (2)	0.0008 (16)	−0.0004 (18)	−0.0033 (14)
O3	0.0193 (18)	0.034 (2)	0.0283 (18)	−0.0077 (15)	0.0085 (14)	−0.0027 (15)
O4	0.0204 (18)	0.034 (2)	0.0269 (18)	−0.0107 (16)	0.0068 (14)	−0.0025 (15)
O5	0.055 (4)	0.020 (3)	0.045 (3)	0.000	0.009 (3)	0.000
O6	0.0212 (19)	0.048 (2)	0.0321 (19)	−0.0155 (17)	0.0099 (15)	−0.0087 (17)
O7	0.061 (4)	0.018 (3)	0.051 (3)	0.000	0.008 (3)	0.000
N1	0.014 (2)	0.028 (2)	0.026 (2)	0.0061 (18)	0.0042 (18)	0.0030 (19)
N2	0.018 (2)	0.027 (2)	0.023 (2)	−0.0050 (18)	0.0070 (18)	−0.0030 (19)
N3	0.022 (2)	0.023 (2)	0.018 (2)	−0.0070 (18)	0.0087 (17)	0.0003 (18)
N4	0.017 (2)	0.029 (2)	0.024 (2)	−0.0063 (18)	0.0100 (18)	0.0037 (19)
C1	0.021 (3)	0.021 (3)	0.018 (2)	0.000 (2)	0.002 (2)	0.000 (2)
C2	0.026 (2)	0.025 (2)	0.024 (2)	0.0081 (19)	0.0061 (18)	0.0021 (19)
C3	0.029 (2)	0.035 (3)	0.023 (2)	0.007 (2)	0.0099 (19)	−0.002 (2)
C4	0.034 (3)	0.034 (3)	0.019 (3)	0.001 (3)	0.005 (2)	0.004 (2)
C5	0.029 (2)	0.025 (3)	0.023 (2)	0.000 (2)	0.0005 (19)	0.002 (2)
C6	0.021 (2)	0.031 (3)	0.019 (2)	0.0000 (19)	0.0017 (18)	−0.004 (2)
C7	0.021 (2)	0.024 (3)	0.014 (2)	−0.007 (2)	0.0127 (18)	−0.0001 (19)
C8	0.027 (3)	0.022 (3)	0.026 (3)	−0.006 (2)	0.012 (2)	−0.003 (2)
C9	0.040 (3)	0.021 (3)	0.030 (3)	0.005 (2)	0.024 (2)	0.003 (2)
C10	0.021 (3)	0.024 (3)	0.017 (2)	0.001 (2)	0.0055 (19)	−0.001 (2)
C11	0.020 (2)	0.021 (2)	0.016 (2)	0.0089 (19)	0.0109 (19)	0.0062 (19)
C12	0.019 (3)	0.021 (3)	0.024 (3)	−0.004 (2)	0.007 (2)	0.004 (2)
C13	0.023 (2)	0.024 (2)	0.023 (2)	−0.0051 (18)	0.0027 (18)	0.0013 (19)
C14	0.028 (2)	0.030 (2)	0.023 (2)	−0.002 (2)	0.0089 (19)	−0.0013 (19)
C15	0.039 (3)	0.030 (3)	0.026 (3)	−0.003 (3)	0.007 (2)	−0.007 (2)
C16	0.033 (3)	0.029 (2)	0.020 (2)	−0.008 (2)	0.0002 (19)	−0.0011 (19)
C17	0.020 (2)	0.028 (2)	0.027 (2)	−0.0046 (18)	0.0028 (18)	0.001 (2)
C18	0.017 (2)	0.022 (3)	0.026 (3)	−0.006 (2)	0.005 (2)	0.000 (2)
C19	0.019 (2)	0.025 (2)	0.026 (2)	0.0006 (18)	0.0035 (18)	0.0048 (19)
C20	0.028 (2)	0.028 (2)	0.031 (3)	−0.002 (2)	0.013 (2)	−0.001 (2)
C21	0.031 (3)	0.030 (3)	0.023 (3)	−0.004 (2)	0.003 (2)	0.001 (2)
C22	0.025 (2)	0.036 (3)	0.026 (2)	−0.006 (2)	−0.0044 (19)	−0.002 (2)
C23	0.022 (2)	0.032 (3)	0.028 (2)	−0.0039 (19)	0.0079 (19)	−0.001 (2)
C24	0.017 (2)	0.016 (2)	0.032 (3)	−0.0096 (19)	−0.007 (2)	0.008 (2)
C25	0.015 (2)	0.026 (3)	0.024 (3)	−0.001 (2)	0.005 (2)	−0.001 (2)
C26	0.015 (3)	0.026 (4)	0.013 (3)	0.000	0.001 (3)	0.000
C27	0.017 (2)	0.024 (3)	0.015 (2)	−0.001 (2)	−0.0013 (19)	0.001 (2)
C28	0.027 (2)	0.027 (2)	0.023 (2)	−0.004 (2)	0.0067 (18)	0.002 (2)
C29	0.026 (2)	0.039 (3)	0.024 (2)	−0.001 (2)	0.0076 (19)	0.008 (2)
C30	0.026 (3)	0.035 (3)	0.022 (3)	−0.001 (2)	0.007 (2)	0.000 (2)
C31	0.032 (3)	0.027 (3)	0.030 (3)	−0.002 (2)	0.002 (2)	−0.006 (2)
C32	0.023 (2)	0.022 (2)	0.031 (3)	−0.0051 (19)	0.0048 (19)	0.002 (2)
C33	0.023 (3)	0.019 (3)	0.028 (3)	−0.008 (2)	−0.006 (2)	0.001 (2)
C34	0.015 (2)	0.027 (3)	0.027 (3)	−0.003 (2)	0.004 (2)	0.001 (2)
C35	0.012 (3)	0.021 (4)	0.016 (3)	0.000	0.000 (2)	0.000

Geometric parameters (Å, º)

O1—C7	1.246 (5)	C13—H13A	0.9500
O2—C9	1.239 (5)	C14—C15	1.389 (6)
O3—C11	1.240 (4)	C14—H14A	0.9500
O4—C24	1.235 (5)	C15—C16	1.378 (6)
O5—C26	1.198 (7)	C15—H15A	0.9500
O6—C33	1.227 (5)	C16—C17	1.388 (5)
O7—C35	1.186 (7)	C16—H16A	0.9500
N1—C7	1.327 (5)	C17—H17A	0.9500
N1—C1	1.414 (5)	C18—C19	1.385 (5)
N1—H1A	0.8800	C18—C23	1.390 (5)
N2—C11	1.330 (5)	C19—C20	1.390 (5)
N2—C12	1.426 (5)	C19—H19A	0.9500
N2—H2B	0.8800	C20—C21	1.383 (6)
N3—C24	1.370 (5)	C20—H20A	0.9500
N3—C18	1.430 (5)	C21—C22	1.378 (5)
N3—H3B	0.8800	C21—H21A	0.9500
N4—C33	1.366 (5)	C22—C23	1.386 (5)
N4—C27	1.425 (5)	C22—H22A	0.9500
N4—H4B	0.8800	C23—H23A	0.9500
C1—C6	1.382 (5)	C24—C25	1.487 (6)
C1—C2	1.390 (5)	C25—C26	1.523 (5)
C2—C3	1.394 (5)	C25—H25A	0.9900
C2—H2A	0.9500	C25—H25B	0.9900
C3—C4	1.387 (5)	C26—C25^i	1.523 (5)
C3—H3A	0.9500	C27—C32	1.386 (5)
C4—C5	1.380 (6)	C27—C28	1.397 (5)
C4—H4A	0.9500	C28—C29	1.385 (5)
C5—C6	1.392 (5)	C28—H28A	0.9500
C5—H5A	0.9500	C29—C30	1.375 (5)
C6—H6A	0.9500	C29—H29A	0.9500
C7—C8	1.542 (5)	C30—C31	1.384 (6)
C8—C9	1.495 (6)	C30—H30A	0.9500
C8—H8A	0.9900	C31—C32	1.391 (5)
C8—H8B	0.9900	C31—H31A	0.9500
C9—C10	1.492 (6)	C32—H32A	0.9500
C10—C11	1.539 (5)	C33—C34	1.491 (6)
C10—H10A	0.9900	C34—C35	1.529 (5)
C10—H10B	0.9900	C34—H34A	0.9900
C12—C17	1.388 (5)	C34—H34B	0.9900
C12—C13	1.396 (5)	C35—C34^i	1.529 (5)
C13—C14	1.391 (5)
C7—N1—C1	125.7 (4)	C17—C16—H16A	120.0
C7—N1—H1A	117.1	C12—C17—C16	120.0 (4)
C1—N1—H1A	117.1	C12—C17—H17A	120.0
C11—N2—C12	125.9 (4)	C16—C17—H17A	120.0
C11—N2—H2B	117.0	C19—C18—C23	119.9 (4)
C12—N2—H2B	117.0	C19—C18—N3	123.2 (4)
C24—N3—C18	127.1 (4)	C23—C18—N3	116.9 (4)
C24—N3—H3B	116.5	C18—C19—C20	119.2 (4)
C18—N3—H3B	116.5	C18—C19—H19A	120.4
C33—N4—C27	127.7 (4)	C20—C19—H19A	120.4
C33—N4—H4B	116.1	C21—C20—C19	121.3 (4)
C27—N4—H4B	116.1	C21—C20—H20A	119.3
C6—C1—C2	119.5 (4)	C19—C20—H20A	119.3
C6—C1—N1	118.7 (4)	C22—C21—C20	118.7 (4)
C2—C1—N1	121.5 (4)	C22—C21—H21A	120.7
C1—C2—C3	119.8 (4)	C20—C21—H21A	120.7
C1—C2—H2A	120.1	C21—C22—C23	121.1 (4)
C3—C2—H2A	120.1	C21—C22—H22A	119.5
C4—C3—C2	120.2 (4)	C23—C22—H22A	119.5
C4—C3—H3A	119.9	C22—C23—C18	119.7 (4)
C2—C3—H3A	119.9	C22—C23—H23A	120.1
C5—C4—C3	119.9 (4)	C18—C23—H23A	120.1
C5—C4—H4A	120.0	O4—C24—N3	122.2 (4)
C3—C4—H4A	120.0	O4—C24—C25	123.4 (4)
C4—C5—C6	119.9 (4)	N3—C24—C25	114.4 (4)
C4—C5—H5A	120.1	C24—C25—C26	109.8 (3)
C6—C5—H5A	120.1	C24—C25—H25A	109.7
C1—C6—C5	120.6 (4)	C26—C25—H25A	109.7
C1—C6—H6A	119.7	C24—C25—H25B	109.7
C5—C6—H6A	119.7	C26—C25—H25B	109.7
O1—C7—N1	125.6 (4)	H25A—C25—H25B	108.2
O1—C7—C8	119.1 (4)	O5—C26—C25	122.1 (3)
N1—C7—C8	115.2 (4)	O5—C26—C25^i	122.1 (3)
C9—C8—C7	111.0 (4)	C25—C26—C25^i	115.8 (6)
C9—C8—H8A	109.4	C32—C27—C28	120.1 (4)
C7—C8—H8A	109.4	C32—C27—N4	119.4 (4)
C9—C8—H8B	109.4	C28—C27—N4	120.3 (4)
C7—C8—H8B	109.4	C29—C28—C27	119.2 (4)
H8A—C8—H8B	108.0	C29—C28—H28A	120.4
O2—C9—C10	120.3 (5)	C27—C28—H28A	120.4
O2—C9—C8	119.1 (4)	C30—C29—C28	121.3 (4)
C10—C9—C8	120.6 (5)	C30—C29—H29A	119.3
C9—C10—C11	110.4 (3)	C28—C29—H29A	119.3
C9—C10—H10A	109.6	C29—C30—C31	119.1 (4)
C11—C10—H10A	109.6	C29—C30—H30A	120.4
C9—C10—H10B	109.6	C31—C30—H30A	120.4
C11—C10—H10B	109.6	C30—C31—C32	120.9 (4)
H10A—C10—H10B	108.1	C30—C31—H31A	119.6
O3—C11—N2	126.3 (4)	C32—C31—H31A	119.6
O3—C11—C10	119.7 (4)	C27—C32—C31	119.4 (4)
N2—C11—C10	113.9 (4)	C27—C32—H32A	120.3
C17—C12—C13	120.4 (4)	C31—C32—H32A	120.3
C17—C12—N2	117.0 (4)	O6—C33—N4	122.1 (4)
C13—C12—N2	122.6 (4)	O6—C33—C34	123.5 (4)
C14—C13—C12	118.8 (4)	N4—C33—C34	114.4 (4)
C14—C13—H13A	120.6	C33—C34—C35	109.9 (3)
C12—C13—H13A	120.6	C33—C34—H34A	109.7
C15—C14—C13	120.6 (4)	C35—C34—H34A	109.7
C15—C14—H14A	119.7	C33—C34—H34B	109.7
C13—C14—H14A	119.7	C35—C34—H34B	109.7
C16—C15—C14	120.1 (4)	H34A—C34—H34B	108.2
C16—C15—H15A	119.9	O7—C35—C34^i	122.0 (3)
C14—C15—H15A	119.9	O7—C35—C34	122.0 (3)
C15—C16—C17	120.0 (4)	C34^i—C35—C34	116.0 (5)
C15—C16—H16A	120.0
C7—N1—C1—C6	146.3 (4)	C24—N3—C18—C19	36.8 (6)
C7—N1—C1—C2	−38.6 (7)	C24—N3—C18—C23	−143.0 (4)
C6—C1—C2—C3	0.8 (6)	C23—C18—C19—C20	0.8 (6)
N1—C1—C2—C3	−174.2 (4)	N3—C18—C19—C20	−179.1 (4)
C1—C2—C3—C4	−0.7 (6)	C18—C19—C20—C21	0.4 (6)
C2—C3—C4—C5	−0.1 (6)	C19—C20—C21—C22	−1.5 (6)
C3—C4—C5—C6	0.8 (6)	C20—C21—C22—C23	1.6 (6)
C2—C1—C6—C5	−0.2 (6)	C21—C22—C23—C18	−0.4 (6)
N1—C1—C6—C5	175.0 (4)	C19—C18—C23—C22	−0.8 (6)
C4—C5—C6—C1	−0.6 (6)	N3—C18—C23—C22	179.1 (3)
C1—N1—C7—O1	−7.6 (7)	C18—N3—C24—O4	−10.8 (7)
C1—N1—C7—C8	168.5 (4)	C18—N3—C24—C25	168.9 (4)
O1—C7—C8—C9	−12.6 (5)	O4—C24—C25—C26	−4.9 (6)
N1—C7—C8—C9	171.1 (4)	N3—C24—C25—C26	175.4 (4)
C7—C8—C9—O2	102.5 (4)	C24—C25—C26—O5	99.8 (3)
C7—C8—C9—C10	−77.5 (4)	C24—C25—C26—C25^i	−80.2 (3)
O2—C9—C10—C11	100.6 (4)	C33—N4—C27—C32	147.9 (4)
C8—C9—C10—C11	−79.4 (4)	C33—N4—C27—C28	−37.6 (6)
C12—N2—C11—O3	−7.9 (7)	C32—C27—C28—C29	−0.2 (6)
C12—N2—C11—C10	168.6 (4)	N4—C27—C28—C29	−174.6 (4)
C9—C10—C11—O3	−7.6 (5)	C27—C28—C29—C30	0.2 (6)
C9—C10—C11—N2	175.6 (4)	C28—C29—C30—C31	−0.1 (6)
C11—N2—C12—C17	−145.3 (4)	C29—C30—C31—C32	0.0 (6)
C11—N2—C12—C13	34.9 (6)	C28—C27—C32—C31	0.1 (6)
C17—C12—C13—C14	1.7 (6)	N4—C27—C32—C31	174.6 (4)
N2—C12—C13—C14	−178.5 (4)	C30—C31—C32—C27	0.0 (6)
C12—C13—C14—C15	−1.4 (6)	C27—N4—C33—O6	−9.1 (7)
C13—C14—C15—C16	0.9 (7)	C27—N4—C33—C34	170.3 (4)
C14—C15—C16—C17	−0.7 (6)	O6—C33—C34—C35	−6.6 (6)
C13—C12—C17—C16	−1.5 (6)	N4—C33—C34—C35	174.0 (4)
N2—C12—C17—C16	178.6 (3)	C33—C34—C35—O7	98.6 (3)
C15—C16—C17—C12	1.0 (6)	C33—C34—C35—C34^i	−81.4 (3)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6^ii	0.88	2.08	2.940 (5)	168
N2—H2B···O4	0.88	2.07	2.929 (5)	166
N3—H3B···O3^iii	0.88	2.08	2.944 (5)	167
N4—H4B···O1^iv	0.88	2.07	2.938 (5)	168
C8—H8B···O2^v	0.99	2.61	3.237 (6)	121
C10—H10B···O2^v	0.99	2.58	3.216 (5)	122
C25—H25A···O7	0.99	2.52	3.188 (6)	124
C34—H34A···O5^vi	0.99	2.53	3.218 (6)	126
C2—H2A···Cg(C12–C17)^ii	0.95	2.94	3.691 (4)	137
C5—H5A···Cg(C12–C17)^v	0.95	2.95	3.719 (4)	138
C28—H28A···Cg(C18–C23)	0.95	2.95	3.701 (4)	137
C31—H31A···Cg(C18–C23)^vi	0.95	2.97	3.723 (4)	137

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

(Ib) 1,5-dianilinopentane-1,3,5-trione

Crystal data

C17H16N2O3	F(000) = 2496
Mr = 296.32	Dx = 1.382 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6859 reflections
a = 17.6547 (5) Å	θ = 2–30°
b = 9.8640 (3) Å	µ = 0.10 mm^−1
c = 32.7904 (8) Å	T = 167 K
β = 93.733 (1)°	Rod, colourless
V = 5698.2 (3) Å^3	0.60 × 0.16 × 0.16 mm
Z = 16

Data collection

Siemens SMART 1K CCD area-detector diffractometer	8093 independent reflections
Radiation source: normal-focus sealed tube	1858 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.176
ω scans	θmax = 30.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −24→24
Tmin = 0.924, Tmax = 0.985	k = −13→13
41837 measured reflections	l = −42→46

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 0.83	w = 1/[σ^2(Fo^2) + (0.02P)^2] where P = (Fo^2 + 2Fc^2)/3
8093 reflections	(Δ/σ)max = 0.001
399 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.18104 (19)	0.1294 (4)	0.17803 (10)	0.0313 (10)
O2	0.2478 (2)	−0.0809 (4)	0.25092 (11)	0.0386 (11)
O3	0.31778 (18)	0.1368 (4)	0.32028 (10)	0.0282 (9)
O4	0.06879 (18)	0.3876 (4)	0.32047 (10)	0.0266 (9)
O5	0.0000	0.1690 (5)	0.2500	0.0374 (15)
O6	0.06905 (18)	0.8792 (4)	0.32184 (10)	0.0297 (10)
O7	0.0000	0.6668 (6)	0.2500	0.0414 (16)
N1	0.2828 (2)	0.2507 (4)	0.15923 (11)	0.0218 (11)
H1A	0.3276	0.2820	0.1681	0.026*
N2	0.2143 (2)	0.2539 (4)	0.34016 (11)	0.0210 (11)
H2B	0.1692	0.2842	0.3315	0.025*
N3	−0.0352 (2)	0.5021 (4)	0.34030 (12)	0.0222 (11)
H3B	−0.0811	0.5284	0.3317	0.027*
N4	−0.0324 (2)	1.0015 (4)	0.34093 (12)	0.0230 (11)
H4B	−0.0771	1.0323	0.3318	0.028*
C1	0.2547 (3)	0.2951 (5)	0.11969 (14)	0.0169 (12)
C2	0.2148 (2)	0.2062 (5)	0.09324 (13)	0.0246 (11)
H2A	0.2021	0.1179	0.1021	0.030*
C3	0.1936 (3)	0.2484 (5)	0.05352 (14)	0.0291 (12)
H3A	0.1656	0.1889	0.0354	0.035*
C4	0.2131 (3)	0.3765 (6)	0.04026 (16)	0.0315 (15)
H4A	0.1996	0.4041	0.0130	0.038*
C5	0.2524 (3)	0.4637 (5)	0.06689 (13)	0.0275 (12)
H5A	0.2646	0.5524	0.0581	0.033*
C6	0.2739 (2)	0.4225 (5)	0.10632 (13)	0.0233 (12)
H6A	0.3020	0.4823	0.1243	0.028*
C7	0.2478 (3)	0.1651 (5)	0.18476 (15)	0.0218 (12)
C8	0.2961 (3)	0.1178 (5)	0.22095 (14)	0.0222 (13)
H8A	0.3210	0.1965	0.2349	0.027*
H8B	0.3361	0.0565	0.2120	0.027*
C9	0.2476 (3)	0.0438 (5)	0.25018 (17)	0.0260 (13)
C10	0.2011 (3)	0.1238 (5)	0.27832 (14)	0.0218 (13)
H10A	0.1781	0.2029	0.2636	0.026*
H10B	0.1597	0.0667	0.2878	0.026*
C11	0.2507 (3)	0.1707 (5)	0.31391 (15)	0.0212 (12)
C12	0.2422 (3)	0.2952 (5)	0.37942 (16)	0.0225 (13)
C13	0.3181 (3)	0.3247 (4)	0.38994 (13)	0.0251 (12)
H13A	0.3545	0.3185	0.3699	0.030*
C14	0.3406 (3)	0.3634 (5)	0.42967 (13)	0.0265 (12)
H14A	0.3926	0.3821	0.4367	0.032*
C15	0.2885 (3)	0.3749 (6)	0.45892 (16)	0.0282 (14)
H15A	0.3046	0.4013	0.4860	0.034*
C16	0.2129 (3)	0.3483 (5)	0.44904 (13)	0.0292 (12)
H16A	0.1770	0.3564	0.4692	0.035*
C17	0.1891 (3)	0.3092 (5)	0.40921 (13)	0.0263 (12)
H17A	0.1369	0.2921	0.4023	0.032*
C18	−0.0080 (3)	0.5469 (5)	0.37983 (16)	0.0215 (13)
C19	0.0686 (2)	0.5758 (4)	0.39018 (13)	0.0223 (11)
H19A	0.1051	0.5688	0.3703	0.027*
C20	0.0902 (3)	0.6149 (5)	0.42996 (13)	0.0280 (12)
H20A	0.1421	0.6348	0.4371	0.034*
C21	0.0378 (3)	0.6254 (5)	0.45938 (16)	0.0287 (14)
H21A	0.0533	0.6506	0.4866	0.034*
C22	−0.0380 (3)	0.5984 (5)	0.44835 (14)	0.0290 (12)
H22A	−0.0746	0.6071	0.4682	0.035*
C23	−0.0608 (3)	0.5592 (4)	0.40924 (13)	0.0264 (12)
H23A	−0.1128	0.5405	0.4023	0.032*
C24	0.0019 (3)	0.4242 (5)	0.31506 (14)	0.0198 (12)
C25	−0.0480 (3)	0.3715 (5)	0.27813 (14)	0.0203 (13)
H25A	−0.0886	0.3127	0.2877	0.024*
H25B	−0.0721	0.4488	0.2631	0.024*
C26	0.0000	0.2919 (8)	0.2500	0.0197 (17)
C27	−0.0048 (3)	1.0446 (6)	0.38087 (15)	0.0221 (13)
C28	0.0363 (2)	0.9575 (5)	0.40708 (13)	0.0260 (12)
H28A	0.0503	0.8700	0.3981	0.031*
C29	0.0565 (2)	0.9994 (5)	0.44643 (13)	0.0284 (12)
H29A	0.0840	0.9396	0.4647	0.034*
C30	0.0373 (3)	1.1274 (6)	0.45974 (16)	0.0283 (14)
H30A	0.0516	1.1556	0.4869	0.034*
C31	−0.0026 (3)	1.2133 (5)	0.43318 (14)	0.0294 (12)
H31A	−0.0158	1.3013	0.4421	0.035*
C32	−0.0240 (2)	1.1728 (5)	0.39322 (13)	0.0264 (12)
H32A	−0.0512	1.2327	0.3749	0.032*
C33	0.0028 (3)	0.9201 (5)	0.31649 (14)	0.0205 (12)
C34	−0.0460 (3)	0.8681 (6)	0.27890 (15)	0.0251 (13)
H34A	−0.0873	0.8104	0.2883	0.030*
H34B	−0.0695	0.9464	0.2641	0.030*
C35	0.0000	0.7874 (8)	0.2500	0.0193 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.023 (2)	0.045 (3)	0.026 (2)	−0.0125 (19)	−0.0022 (17)	0.0052 (19)
O2	0.054 (3)	0.024 (2)	0.038 (2)	0.000 (2)	0.009 (2)	−0.001 (2)
O3	0.018 (2)	0.035 (2)	0.031 (2)	0.0071 (18)	0.0030 (17)	−0.0018 (18)
O4	0.017 (2)	0.033 (2)	0.029 (2)	0.0099 (17)	−0.0029 (16)	−0.0031 (18)
O5	0.053 (4)	0.015 (3)	0.044 (4)	0.000	0.007 (3)	0.000
O6	0.018 (2)	0.044 (3)	0.027 (2)	0.0108 (19)	−0.0037 (16)	−0.0057 (19)
O7	0.063 (4)	0.016 (3)	0.046 (4)	0.000	0.005 (3)	0.000
N1	0.012 (2)	0.029 (3)	0.024 (3)	−0.008 (2)	−0.0011 (19)	−0.002 (2)
N2	0.021 (3)	0.024 (3)	0.017 (2)	0.008 (2)	−0.0059 (19)	−0.001 (2)
N3	0.016 (3)	0.027 (3)	0.022 (3)	0.005 (2)	−0.0026 (19)	−0.004 (2)
N4	0.013 (2)	0.028 (3)	0.028 (3)	0.003 (2)	0.003 (2)	0.000 (2)
C1	0.017 (3)	0.023 (3)	0.010 (3)	0.000 (2)	0.000 (2)	0.002 (2)
C2	0.025 (3)	0.026 (3)	0.021 (3)	0.001 (2)	−0.001 (2)	0.006 (2)
C3	0.026 (3)	0.031 (3)	0.030 (3)	−0.005 (2)	−0.004 (2)	−0.001 (2)
C4	0.033 (4)	0.041 (4)	0.020 (3)	−0.006 (3)	0.001 (3)	−0.006 (3)
C5	0.037 (3)	0.023 (3)	0.024 (3)	0.003 (2)	0.007 (2)	0.007 (2)
C6	0.025 (3)	0.020 (3)	0.026 (3)	−0.005 (2)	0.005 (2)	−0.008 (2)
C7	0.024 (3)	0.013 (3)	0.030 (3)	−0.008 (2)	0.011 (2)	−0.002 (2)
C8	0.018 (3)	0.023 (3)	0.026 (3)	−0.004 (2)	−0.001 (2)	−0.002 (2)
C9	0.026 (3)	0.019 (3)	0.030 (3)	−0.011 (3)	−0.018 (2)	0.005 (3)
C10	0.015 (3)	0.026 (3)	0.025 (3)	0.005 (2)	0.006 (2)	−0.004 (2)
C11	0.021 (3)	0.013 (3)	0.031 (3)	0.007 (2)	0.012 (2)	0.008 (2)
C12	0.011 (3)	0.022 (3)	0.035 (3)	0.004 (2)	0.007 (2)	0.005 (3)
C13	0.032 (3)	0.023 (3)	0.021 (3)	0.004 (2)	0.005 (2)	0.002 (2)
C14	0.023 (3)	0.030 (3)	0.026 (3)	−0.003 (2)	0.000 (2)	0.003 (2)
C15	0.033 (4)	0.031 (4)	0.021 (3)	0.002 (3)	−0.001 (3)	0.001 (3)
C16	0.040 (3)	0.032 (3)	0.017 (3)	0.005 (3)	0.010 (2)	−0.001 (2)
C17	0.019 (3)	0.031 (3)	0.029 (3)	0.008 (2)	0.003 (2)	−0.003 (2)
C18	0.017 (3)	0.019 (3)	0.028 (3)	0.006 (2)	0.001 (2)	0.008 (3)
C19	0.014 (2)	0.026 (3)	0.027 (3)	0.002 (2)	0.003 (2)	0.004 (2)
C20	0.028 (3)	0.027 (3)	0.028 (3)	0.005 (2)	−0.007 (2)	−0.005 (2)
C21	0.033 (4)	0.028 (3)	0.025 (3)	0.001 (3)	0.000 (3)	−0.010 (3)
C22	0.027 (3)	0.031 (3)	0.030 (3)	0.008 (2)	0.008 (2)	−0.003 (3)
C23	0.023 (3)	0.029 (3)	0.027 (3)	0.001 (2)	0.002 (2)	0.003 (2)
C24	0.018 (3)	0.027 (3)	0.014 (3)	−0.003 (2)	0.001 (2)	0.004 (2)
C25	0.018 (3)	0.023 (3)	0.019 (3)	−0.008 (2)	−0.004 (2)	0.002 (2)
C26	0.019 (4)	0.023 (5)	0.017 (4)	0.000	−0.002 (3)	0.000
C27	0.030 (3)	0.024 (3)	0.012 (3)	0.001 (3)	0.002 (2)	−0.005 (2)
C28	0.026 (3)	0.026 (3)	0.026 (3)	0.014 (2)	0.004 (2)	0.005 (2)
C29	0.023 (3)	0.044 (3)	0.018 (3)	0.006 (3)	−0.002 (2)	0.008 (2)
C30	0.029 (3)	0.032 (4)	0.024 (3)	−0.002 (3)	0.002 (3)	−0.006 (3)
C31	0.029 (3)	0.030 (3)	0.030 (3)	0.003 (2)	0.006 (2)	−0.001 (3)
C32	0.023 (3)	0.033 (3)	0.023 (3)	0.002 (2)	0.002 (2)	−0.001 (2)
C33	0.019 (3)	0.028 (3)	0.013 (2)	−0.009 (2)	−0.013 (2)	0.001 (2)
C34	0.022 (3)	0.028 (3)	0.025 (3)	−0.003 (2)	−0.003 (2)	0.002 (3)
C35	0.017 (4)	0.029 (5)	0.012 (4)	0.000	0.012 (3)	0.000

Geometric parameters (Å, º)

O1—C7	1.237 (5)	C13—H13A	0.9500
O2—C9	1.230 (6)	C14—C15	1.376 (6)
O3—C11	1.235 (5)	C14—H14A	0.9500
O4—C24	1.237 (5)	C15—C16	1.378 (6)
O5—C26	1.212 (8)	C15—H15A	0.9500
O6—C33	1.240 (5)	C16—C17	1.400 (6)
O7—C35	1.190 (8)	C16—H16A	0.9500
N1—C7	1.365 (6)	C17—H17A	0.9500
N1—C1	1.426 (6)	C18—C23	1.389 (6)
N1—H1A	0.8800	C18—C19	1.402 (6)
N2—C11	1.378 (5)	C19—C20	1.390 (6)
N2—C12	1.408 (6)	C19—H19A	0.9500
N2—H2B	0.8800	C20—C21	1.384 (6)
N3—C24	1.332 (6)	C20—H20A	0.9500
N3—C18	1.423 (6)	C21—C22	1.389 (6)
N3—H3B	0.8800	C21—H21A	0.9500
N4—C33	1.317 (6)	C22—C23	1.374 (6)
N4—C27	1.432 (6)	C22—H22A	0.9500
N4—H4B	0.8800	C23—H23A	0.9500
C1—C6	1.380 (6)	C24—C25	1.540 (6)
C1—C2	1.393 (6)	C25—C26	1.512 (6)
C2—C3	1.395 (6)	C25—H25A	0.9900
C2—H2A	0.9500	C25—H25B	0.9900
C3—C4	1.388 (7)	C26—C25^i	1.512 (6)
C3—H3A	0.9500	C27—C32	1.377 (6)
C4—C5	1.380 (7)	C27—C28	1.386 (6)
C4—H4A	0.9500	C28—C29	1.380 (6)
C5—C6	1.385 (5)	C28—H28A	0.9500
C5—H5A	0.9500	C29—C30	1.386 (7)
C6—H6A	0.9500	C29—H29A	0.9500
C7—C8	1.490 (6)	C30—C31	1.376 (7)
C8—C9	1.514 (7)	C30—H30A	0.9500
C8—H8A	0.9900	C31—C32	1.398 (6)
C8—H8B	0.9900	C31—H31A	0.9500
C9—C10	1.498 (7)	C32—H32A	0.9500
C10—C11	1.486 (6)	C33—C34	1.544 (6)
C10—H10A	0.9900	C34—C35	1.514 (6)
C10—H10B	0.9900	C34—H34A	0.9900
C12—C13	1.391 (6)	C34—H34B	0.9900
C12—C17	1.404 (6)	C35—C34^i	1.514 (6)
C13—C14	1.391 (6)
C7—N1—C1	127.1 (4)	C17—C16—H16A	120.0
C7—N1—H1A	116.4	C16—C17—C12	120.2 (4)
C1—N1—H1A	116.4	C16—C17—H17A	119.9
C11—N2—C12	126.4 (4)	C12—C17—H17A	119.9
C11—N2—H2B	116.8	C23—C18—C19	119.6 (5)
C12—N2—H2B	116.8	C23—C18—N3	117.2 (4)
C24—N3—C18	126.5 (4)	C19—C18—N3	123.1 (4)
C24—N3—H3B	116.8	C20—C19—C18	119.1 (4)
C18—N3—H3B	116.8	C20—C19—H19A	120.5
C33—N4—C27	126.3 (4)	C18—C19—H19A	120.5
C33—N4—H4B	116.8	C21—C20—C19	121.3 (4)
C27—N4—H4B	116.8	C21—C20—H20A	119.4
C6—C1—C2	120.0 (4)	C19—C20—H20A	119.4
C6—C1—N1	119.4 (4)	C20—C21—C22	118.8 (5)
C2—C1—N1	120.3 (4)	C20—C21—H21A	120.6
C1—C2—C3	119.2 (4)	C22—C21—H21A	120.6
C1—C2—H2A	120.4	C23—C22—C21	121.0 (5)
C3—C2—H2A	120.4	C23—C22—H22A	119.5
C4—C3—C2	120.5 (4)	C21—C22—H22A	119.5
C4—C3—H3A	119.8	C22—C23—C18	120.2 (4)
C2—C3—H3A	119.8	C22—C23—H23A	119.9
C5—C4—C3	119.6 (5)	C18—C23—H23A	119.9
C5—C4—H4A	120.2	O4—C24—N3	125.7 (5)
C3—C4—H4A	120.2	O4—C24—C25	120.4 (5)
C4—C5—C6	120.3 (5)	N3—C24—C25	113.8 (4)
C4—C5—H5A	119.9	C26—C25—C24	109.9 (4)
C6—C5—H5A	119.9	C26—C25—H25A	109.7
C1—C6—C5	120.4 (4)	C24—C25—H25A	109.7
C1—C6—H6A	119.8	C26—C25—H25B	109.7
C5—C6—H6A	119.8	C24—C25—H25B	109.7
O1—C7—N1	122.1 (5)	H25A—C25—H25B	108.2
O1—C7—C8	122.8 (5)	O5—C26—C25^i	121.3 (3)
N1—C7—C8	115.1 (4)	O5—C26—C25	121.3 (3)
C7—C8—C9	109.7 (4)	C25^i—C26—C25	117.5 (7)
C7—C8—H8A	109.7	C32—C27—C28	121.0 (4)
C9—C8—H8A	109.7	C32—C27—N4	117.8 (4)
C7—C8—H8B	109.7	C28—C27—N4	121.1 (5)
C9—C8—H8B	109.7	C29—C28—C27	119.2 (4)
H8A—C8—H8B	108.2	C29—C28—H28A	120.4
O2—C9—C10	121.1 (6)	C27—C28—H28A	120.4
O2—C9—C8	119.5 (6)	C28—C29—C30	120.9 (4)
C10—C9—C8	119.4 (5)	C28—C29—H29A	119.6
C11—C10—C9	109.2 (4)	C30—C29—H29A	119.6
C11—C10—H10A	109.8	C31—C30—C29	119.2 (5)
C9—C10—H10A	109.8	C31—C30—H30A	120.4
C11—C10—H10B	109.8	C29—C30—H30A	120.4
C9—C10—H10B	109.8	C30—C31—C32	120.9 (5)
H10A—C10—H10B	108.3	C30—C31—H31A	119.6
O3—C11—N2	122.4 (5)	C32—C31—H31A	119.6
O3—C11—C10	123.9 (5)	C27—C32—C31	118.8 (4)
N2—C11—C10	113.6 (4)	C27—C32—H32A	120.6
C13—C12—C17	118.8 (5)	C31—C32—H32A	120.6
C13—C12—N2	124.1 (4)	O6—C33—N4	126.1 (4)
C17—C12—N2	117.0 (4)	O6—C33—C34	118.4 (5)
C14—C13—C12	120.1 (4)	N4—C33—C34	115.4 (4)
C14—C13—H13A	119.9	C35—C34—C33	112.4 (4)
C12—C13—H13A	119.9	C35—C34—H34A	109.1
C15—C14—C13	120.8 (4)	C33—C34—H34A	109.1
C15—C14—H14A	119.6	C35—C34—H34B	109.1
C13—C14—H14A	119.6	C33—C34—H34B	109.1
C14—C15—C16	120.1 (5)	H34A—C34—H34B	107.9
C14—C15—H15A	120.0	O7—C35—C34	121.7 (3)
C16—C15—H15A	120.0	O7—C35—C34^i	121.7 (3)
C15—C16—C17	119.9 (4)	C34—C35—C34^i	116.5 (7)
C15—C16—H16A	120.0
C7—N1—C1—C6	148.4 (5)	C24—N3—C18—C23	−145.4 (5)
C7—N1—C1—C2	−37.9 (7)	C24—N3—C18—C19	33.2 (7)
C6—C1—C2—C3	−0.9 (7)	C23—C18—C19—C20	0.7 (7)
N1—C1—C2—C3	−174.5 (4)	N3—C18—C19—C20	−177.9 (4)
C1—C2—C3—C4	1.0 (7)	C18—C19—C20—C21	0.2 (7)
C2—C3—C4—C5	−1.4 (7)	C19—C20—C21—C22	−1.1 (8)
C3—C4—C5—C6	1.7 (8)	C20—C21—C22—C23	1.3 (8)
C2—C1—C6—C5	1.2 (7)	C21—C22—C23—C18	−0.4 (7)
N1—C1—C6—C5	174.9 (4)	C19—C18—C23—C22	−0.6 (7)
C4—C5—C6—C1	−1.6 (7)	N3—C18—C23—C22	178.2 (4)
C1—N1—C7—O1	−9.9 (8)	C18—N3—C24—O4	−6.6 (8)
C1—N1—C7—C8	169.8 (5)	C18—N3—C24—C25	169.1 (4)
O1—C7—C8—C9	−9.8 (7)	O4—C24—C25—C26	−7.6 (7)
N1—C7—C8—C9	170.5 (4)	N3—C24—C25—C26	176.4 (4)
C7—C8—C9—O2	101.5 (5)	C24—C25—C26—O5	101.5 (4)
C7—C8—C9—C10	−79.7 (5)	C24—C25—C26—C25^i	−78.5 (4)
O2—C9—C10—C11	98.8 (5)	C33—N4—C27—C32	146.8 (5)
C8—C9—C10—C11	−80.0 (5)	C33—N4—C27—C28	−36.7 (7)
C12—N2—C11—O3	−9.9 (8)	C32—C27—C28—C29	1.5 (7)
C12—N2—C11—C10	168.7 (5)	N4—C27—C28—C29	−174.8 (4)
C9—C10—C11—O3	−6.0 (7)	C27—C28—C29—C30	−0.9 (7)
C9—C10—C11—N2	175.5 (4)	C28—C29—C30—C31	0.1 (7)
C11—N2—C12—C13	36.8 (8)	C29—C30—C31—C32	0.1 (8)
C11—N2—C12—C17	−144.4 (5)	C28—C27—C32—C31	−1.3 (7)
C17—C12—C13—C14	1.9 (7)	N4—C27—C32—C31	175.2 (4)
N2—C12—C13—C14	−179.3 (4)	C30—C31—C32—C27	0.5 (7)
C12—C13—C14—C15	−0.9 (7)	C27—N4—C33—O6	−8.7 (8)
C13—C14—C15—C16	−0.1 (8)	C27—N4—C33—C34	168.6 (5)
C14—C15—C16—C17	0.1 (8)	O6—C33—C34—C35	−8.5 (7)
C15—C16—C17—C12	0.9 (7)	N4—C33—C34—C35	174.1 (5)
C13—C12—C17—C16	−1.9 (7)	C33—C34—C35—O7	99.7 (4)
N2—C12—C17—C16	179.2 (4)	C33—C34—C35—C34^i	−80.3 (4)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6^ii	0.88	2.07	2.936 (5)	168
N2—H2B···O4	0.88	2.06	2.922 (5)	168
N3—H3B···O3^iii	0.88	2.09	2.952 (5)	165
N4—H4B···O1^iv	0.88	2.08	2.942 (5)	167
C8—H8A···O2^v	0.99	2.57	3.221 (6)	124
C10—H10A···O2^v	0.99	2.56	3.214 (6)	123
C25—H25B···O7	0.99	2.55	3.187 (7)	122
C34—H34B···O5^vi	0.99	2.57	3.235 (7)	124
C2—H2A···Cg1(C12–C17)^ii	0.95	2.93	3.694 (5)	138
C5—H5A···Cg1(C12–C17)^v	0.95	2.95	3.715 (5)	139
C28—H28A···Cg2(C18–C23)	0.95	2.96	3.701 (5)	136
C31—H31A···Cg2(C18–C23)^vi	0.95	2.97	3.727 (5)	137

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