N-(3,4-Dimethyl-phen-yl)-4-methyl-benzamide.

The title compound, C(16)H(17)NO, crystallizes with two mol-ecules in the asymmetric unit. The conformation of the N-H bond is anti to the meta-methyl substituent in the aniline ring in the first mol-ecule and syn in the second mol-ecule. The dihedral angles between the two benzene rings are 52.6 (1) and 10.5 (1)° in the first and second mol-ecules, respectively. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains running along the b axis of the crystal.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ▶). For related structures, see: Bowes et al. (2003 ▶); n class="Chemical">Gowda et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C16H17NO

M = 239.31

Triclinic,

a = 9.4186 (3) Å

b = 9.55915 (18) Å

c = 15.8813 (4) Å

α = 74.361 (2)°

β = 79.696 (2)°

γ = 88.1582 (18)°

V = 1354.51 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 295 K

0.51 × 0.41 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.943, T max = 0.981

24655 measured reflections

5130 independent reflections

3880 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.126

S = 1.09

5130 reflections

332 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809041257/bt5089sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041257/bt5089Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H17NO	Z = 4
Mr = 239.31	F(000) = 512
Triclinic, P1	Dx = 1.173 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4186 (3) Å	Cell parameters from 13000 reflections
b = 9.55915 (18) Å	θ = 2.2–29.3°
c = 15.8813 (4) Å	µ = 0.07 mm−1
α = 74.361 (2)°	T = 295 K
β = 79.696 (2)°	Block, colourless
γ = 88.1582 (18)°	0.51 × 0.41 × 0.22 mm
V = 1354.51 (6) Å3

Oxford Diffraction Xcalibur with a Ruby Gemini detector diffractometer	5130 independent reflections
graphite	3880 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.016
ω scans	θmax = 25.7°, θmin = 2.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −11→11
Tmin = 0.943, Tmax = 0.981	k = −11→11
24655 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0705P)2 + 0.0954P] where P = (Fo2 + 2Fc2)/3
5130 reflections	(Δ/σ)max < 0.001
332 parameters	Δρmax = 0.19 e Å−3
2 restraints	Δρmin = −0.13 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.10346 (14)	0.30182 (13)	0.21469 (9)	0.0465 (3)
C2	0.11199 (14)	0.43910 (14)	0.15658 (9)	0.0488 (3)
H2	0.1996	0.4899	0.1399	0.059*
C3	−0.00845 (15)	0.50305 (14)	0.12241 (9)	0.0502 (3)
C4	−0.13954 (15)	0.42676 (15)	0.14676 (10)	0.0536 (4)
C5	−0.14410 (15)	0.28750 (16)	0.20304 (10)	0.0571 (4)
H5	−0.2303	0.2345	0.2184	0.069*
C6	−0.02543 (15)	0.22486 (15)	0.23707 (10)	0.0538 (4)
H6	−0.0322	0.1313	0.2749	0.065*
C7	0.32980 (14)	0.30304 (13)	0.27355 (9)	0.0483 (3)
C8	0.43956 (14)	0.20801 (13)	0.31706 (9)	0.0464 (3)
C9	0.51877 (16)	0.26395 (15)	0.36612 (10)	0.0569 (4)
H9	0.5038	0.3591	0.3695	0.068*
C10	0.61908 (16)	0.18210 (16)	0.40995 (10)	0.0601 (4)
H10	0.6691	0.2219	0.4437	0.072*
C11	0.64706 (15)	0.04163 (15)	0.40481 (10)	0.0549 (4)
C12	0.57052 (16)	−0.01379 (15)	0.35434 (11)	0.0603 (4)
H12	0.5887	−0.1076	0.3491	0.072*
C13	0.46711 (16)	0.06721 (14)	0.31119 (10)	0.0554 (4)
H13	0.416	0.027	0.2782	0.067*
C14	0.00537 (19)	0.65361 (16)	0.06181 (11)	0.0678 (4)
H14A	0.1056	0.6805	0.0424	0.102*
H14B	−0.0423	0.7201	0.0929	0.102*
H14C	−0.0384	0.6569	0.0112	0.102*
C15	−0.27382 (18)	0.4940 (2)	0.11380 (14)	0.0790 (5)
H15A	−0.287	0.5882	0.1243	0.118*
H15B	−0.3562	0.433	0.1449	0.118*
H15C	−0.2636	0.5034	0.0513	0.118*
C16	0.75981 (18)	−0.04604 (19)	0.45196 (12)	0.0738 (5)
H16A	0.819	0.0174	0.4694	0.111*	0.5
H16B	0.819	−0.094	0.4127	0.111*	0.5
H16C	0.7132	−0.1173	0.5038	0.111*	0.5
H16D	0.7484	−0.1466	0.4546	0.111*	0.5
H16E	0.7484	−0.0353	0.5112	0.111*	0.5
H16F	0.8542	−0.012	0.4201	0.111*	0.5
N1	0.22333 (12)	0.23479 (11)	0.25316 (8)	0.0522 (3)
H1N	0.2277	0.1417	0.2643	0.063*
O1	0.33726 (11)	0.43667 (9)	0.25845 (7)	0.0638 (3)
C21	0.74411 (15)	0.18251 (13)	0.82751 (10)	0.0510 (3)
C22	0.64037 (16)	0.22586 (15)	0.88897 (10)	0.0549 (4)
H22	0.5795	0.3012	0.8688	0.066*
C23	0.62458 (16)	0.16037 (16)	0.97944 (10)	0.0585 (4)
C24	0.71696 (18)	0.04716 (15)	1.00955 (10)	0.0626 (4)
C25	0.81944 (19)	0.00514 (16)	0.94732 (11)	0.0651 (4)
H25	0.8804	−0.0704	0.9671	0.078*
C26	0.83512 (17)	0.07014 (15)	0.85765 (11)	0.0605 (4)
H26	0.9056	0.0393	0.8178	0.073*
C27	0.81041 (15)	0.21391 (14)	0.66478 (10)	0.0513 (3)
C28	0.81065 (15)	0.32107 (14)	0.57693 (9)	0.0490 (3)
C29	0.91799 (16)	0.31421 (16)	0.50555 (11)	0.0575 (4)
H29	0.987	0.2423	0.5134	0.069*
C30	0.92379 (17)	0.41186 (17)	0.42359 (11)	0.0621 (4)
H30	0.9981	0.4065	0.3774	0.074*
C31	0.82068 (18)	0.51821 (16)	0.40875 (10)	0.0598 (4)
C32	0.71185 (18)	0.52273 (16)	0.47904 (10)	0.0612 (4)
H32	0.6403	0.5918	0.4703	0.073*
C33	0.70702 (16)	0.42699 (15)	0.56190 (10)	0.0567 (4)
H33	0.6334	0.4335	0.6082	0.068*
C34	0.5104 (2)	0.2114 (2)	1.04295 (12)	0.0811 (5)
H34A	0.5544	0.2391	1.0863	0.122*
H34B	0.4413	0.1343	1.0724	0.122*
H34C	0.4627	0.2934	1.0108	0.122*
C35	0.7065 (2)	−0.0265 (2)	1.10752 (12)	0.0877 (6)
H35A	0.7735	−0.1047	1.1154	0.132*
H35B	0.6102	−0.0641	1.1319	0.132*
H35C	0.729	0.0427	1.1374	0.132*
C36	0.8276 (2)	0.6250 (2)	0.31868 (12)	0.0885 (6)
H36A	0.9105	0.6056	0.2788	0.133*	0.5
H36B	0.8349	0.722	0.324	0.133*	0.5
H36C	0.7418	0.6152	0.2959	0.133*	0.5
H36D	0.7476	0.6896	0.3203	0.133*	0.5
H36E	0.8232	0.5732	0.2751	0.133*	0.5
H36F	0.9164	0.68	0.3033	0.133*	0.5
N2	0.75630 (13)	0.26110 (11)	0.73672 (8)	0.0549 (3)
H2N	0.7257	0.3488	0.7264	0.066*
O2	0.85769 (12)	0.09069 (10)	0.67005 (7)	0.0667 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0471 (7)	0.0423 (7)	0.0512 (8)	0.0065 (6)	−0.0090 (6)	−0.0149 (6)
C2	0.0438 (7)	0.0467 (7)	0.0571 (8)	−0.0020 (6)	−0.0106 (6)	−0.0144 (6)
C3	0.0564 (8)	0.0446 (7)	0.0529 (8)	0.0033 (6)	−0.0142 (7)	−0.0158 (6)
C4	0.0478 (8)	0.0568 (8)	0.0618 (9)	0.0048 (6)	−0.0153 (7)	−0.0223 (7)
C5	0.0457 (8)	0.0577 (8)	0.0681 (10)	−0.0055 (7)	−0.0070 (7)	−0.0183 (7)
C6	0.0537 (8)	0.0452 (7)	0.0590 (9)	−0.0006 (6)	−0.0042 (7)	−0.0115 (6)
C7	0.0518 (8)	0.0403 (6)	0.0518 (8)	0.0060 (6)	−0.0073 (6)	−0.0123 (6)
C8	0.0447 (7)	0.0406 (7)	0.0491 (8)	0.0056 (6)	−0.0035 (6)	−0.0078 (6)
C9	0.0590 (9)	0.0468 (7)	0.0689 (10)	0.0088 (7)	−0.0138 (7)	−0.0215 (7)
C10	0.0569 (9)	0.0615 (9)	0.0638 (10)	0.0040 (7)	−0.0158 (7)	−0.0171 (7)
C11	0.0454 (8)	0.0547 (8)	0.0542 (8)	0.0054 (6)	−0.0045 (6)	−0.0004 (7)
C12	0.0628 (9)	0.0410 (7)	0.0742 (10)	0.0126 (7)	−0.0124 (8)	−0.0114 (7)
C13	0.0561 (8)	0.0461 (7)	0.0661 (9)	0.0083 (6)	−0.0155 (7)	−0.0162 (7)
C14	0.0778 (11)	0.0526 (8)	0.0736 (11)	0.0044 (8)	−0.0314 (9)	−0.0069 (8)
C15	0.0593 (10)	0.0817 (11)	0.1008 (14)	0.0088 (9)	−0.0308 (9)	−0.0226 (10)
C16	0.0613 (10)	0.0733 (10)	0.0743 (11)	0.0121 (8)	−0.0174 (8)	0.0035 (9)
N1	0.0549 (7)	0.0350 (5)	0.0658 (8)	0.0044 (5)	−0.0144 (6)	−0.0101 (5)
O1	0.0730 (7)	0.0377 (4)	0.0875 (8)	0.0087 (5)	−0.0319 (6)	−0.0175 (5)
C21	0.0560 (8)	0.0375 (6)	0.0605 (9)	−0.0002 (6)	−0.0165 (7)	−0.0106 (6)
C22	0.0542 (8)	0.0464 (7)	0.0659 (10)	0.0028 (6)	−0.0163 (7)	−0.0148 (7)
C23	0.0608 (9)	0.0524 (8)	0.0644 (10)	−0.0087 (7)	−0.0128 (7)	−0.0168 (7)
C24	0.0765 (10)	0.0475 (8)	0.0630 (10)	−0.0104 (7)	−0.0211 (8)	−0.0063 (7)
C25	0.0776 (11)	0.0451 (8)	0.0720 (11)	0.0081 (7)	−0.0262 (9)	−0.0072 (7)
C26	0.0673 (10)	0.0451 (7)	0.0689 (10)	0.0092 (7)	−0.0175 (8)	−0.0124 (7)
C27	0.0501 (8)	0.0401 (7)	0.0668 (9)	0.0054 (6)	−0.0163 (7)	−0.0163 (6)
C28	0.0500 (8)	0.0417 (7)	0.0604 (9)	0.0033 (6)	−0.0162 (7)	−0.0185 (6)
C29	0.0523 (8)	0.0555 (8)	0.0726 (10)	0.0107 (7)	−0.0161 (7)	−0.0287 (8)
C30	0.0642 (10)	0.0676 (9)	0.0596 (9)	−0.0015 (8)	−0.0054 (8)	−0.0291 (8)
C31	0.0743 (10)	0.0550 (8)	0.0552 (9)	0.0011 (7)	−0.0147 (8)	−0.0215 (7)
C32	0.0705 (10)	0.0540 (8)	0.0600 (9)	0.0164 (7)	−0.0172 (8)	−0.0152 (7)
C33	0.0595 (9)	0.0520 (8)	0.0577 (9)	0.0122 (7)	−0.0082 (7)	−0.0157 (7)
C34	0.0821 (12)	0.0884 (12)	0.0752 (12)	−0.0012 (10)	−0.0092 (9)	−0.0289 (10)
C35	0.1162 (16)	0.0751 (11)	0.0675 (11)	−0.0026 (11)	−0.0260 (11)	−0.0052 (9)
C36	0.1194 (16)	0.0842 (12)	0.0585 (11)	0.0085 (11)	−0.0133 (10)	−0.0158 (9)
N2	0.0663 (8)	0.0392 (6)	0.0596 (7)	0.0121 (5)	−0.0157 (6)	−0.0123 (5)
O2	0.0815 (7)	0.0407 (5)	0.0802 (7)	0.0160 (5)	−0.0193 (6)	−0.0187 (5)

C1—C6	1.3796 (19)	C21—C26	1.3885 (19)
C1—C2	1.3812 (18)	C21—C22	1.389 (2)
C1—N1	1.4309 (16)	C21—N2	1.4209 (18)
C2—C3	1.3970 (18)	C22—C23	1.387 (2)
C2—H2	0.93	C22—H22	0.93
C3—C4	1.393 (2)	C23—C24	1.402 (2)
C3—C14	1.495 (2)	C23—C34	1.501 (2)
C4—C5	1.386 (2)	C24—C25	1.385 (2)
C4—C15	1.513 (2)	C24—C35	1.512 (2)
C5—C6	1.378 (2)	C25—C26	1.375 (2)
C5—H5	0.93	C25—H25	0.93
C6—H6	0.93	C26—H26	0.93
C7—O1	1.2364 (15)	C27—O2	1.2326 (15)
C7—N1	1.3448 (17)	C27—N2	1.3502 (18)
C7—C8	1.4927 (18)	C27—C28	1.491 (2)
C8—C9	1.3812 (19)	C28—C33	1.3872 (19)
C8—C13	1.3871 (18)	C28—C29	1.392 (2)
C9—C10	1.372 (2)	C29—C30	1.375 (2)
C9—H9	0.93	C29—H29	0.93
C10—C11	1.381 (2)	C30—C31	1.386 (2)
C10—H10	0.93	C30—H30	0.93
C11—C12	1.380 (2)	C31—C32	1.383 (2)
C11—C16	1.510 (2)	C31—C36	1.508 (2)
C12—C13	1.3863 (19)	C32—C33	1.380 (2)
C12—H12	0.93	C32—H32	0.93
C13—H13	0.93	C33—H33	0.93
C14—H14A	0.96	C34—H34A	0.96
C14—H14B	0.96	C34—H34B	0.96
C14—H14C	0.96	C34—H34C	0.96
C15—H15A	0.96	C35—H35A	0.96
C15—H15B	0.96	C35—H35B	0.96
C15—H15C	0.96	C35—H35C	0.96
C16—H16A	0.96	C36—H36A	0.96
C16—H16B	0.96	C36—H36B	0.96
C16—H16C	0.96	C36—H36C	0.96
C16—H16D	0.96	C36—H36D	0.96
C16—H16E	0.96	C36—H36E	0.96
C16—H16F	0.96	C36—H36F	0.96
N1—H1N	0.86	N2—H2N	0.86
C6—C1—C2	119.20 (12)	C26—C21—C22	118.95 (14)
C6—C1—N1	118.01 (11)	C26—C21—N2	123.14 (13)
C2—C1—N1	122.79 (12)	C22—C21—N2	117.83 (12)
C1—C2—C3	121.25 (12)	C23—C22—C21	122.13 (13)
C1—C2—H2	119.4	C23—C22—H22	118.9
C3—C2—H2	119.4	C21—C22—H22	118.9
C4—C3—C2	119.52 (12)	C22—C23—C24	118.70 (14)
C4—C3—C14	121.29 (13)	C22—C23—C34	119.93 (14)
C2—C3—C14	119.17 (13)	C24—C23—C34	121.37 (15)
C5—C4—C3	118.06 (12)	C25—C24—C23	118.36 (14)
C5—C4—C15	120.72 (14)	C25—C24—C35	120.60 (15)
C3—C4—C15	121.22 (13)	C23—C24—C35	121.03 (16)
C6—C5—C4	122.34 (13)	C26—C25—C24	122.92 (14)
C6—C5—H5	118.8	C26—C25—H25	118.5
C4—C5—H5	118.8	C24—C25—H25	118.5
C5—C6—C1	119.57 (13)	C25—C26—C21	118.94 (15)
C5—C6—H6	120.2	C25—C26—H26	120.5
C1—C6—H6	120.2	C21—C26—H26	120.5
O1—C7—N1	122.74 (12)	O2—C27—N2	122.99 (13)
O1—C7—C8	121.06 (12)	O2—C27—C28	121.21 (13)
N1—C7—C8	116.20 (11)	N2—C27—C28	115.80 (11)
C9—C8—C13	117.98 (12)	C33—C28—C29	117.72 (13)
C9—C8—C7	117.90 (11)	C33—C28—C27	123.19 (13)
C13—C8—C7	124.11 (12)	C29—C28—C27	119.08 (12)
C10—C9—C8	121.37 (13)	C30—C29—C28	121.18 (13)
C10—C9—H9	119.3	C30—C29—H29	119.4
C8—C9—H9	119.3	C28—C29—H29	119.4
C9—C10—C11	121.13 (14)	C29—C30—C31	121.05 (14)
C9—C10—H10	119.4	C29—C30—H30	119.5
C11—C10—H10	119.4	C31—C30—H30	119.5
C12—C11—C10	117.77 (13)	C32—C31—C30	117.79 (14)
C12—C11—C16	121.72 (14)	C32—C31—C36	121.41 (15)
C10—C11—C16	120.50 (15)	C30—C31—C36	120.79 (15)
C11—C12—C13	121.47 (13)	C33—C32—C31	121.46 (14)
C11—C12—H12	119.3	C33—C32—H32	119.3
C13—C12—H12	119.3	C31—C32—H32	119.3
C12—C13—C8	120.26 (13)	C32—C33—C28	120.77 (14)
C12—C13—H13	119.9	C32—C33—H33	119.6
C8—C13—H13	119.9	C28—C33—H33	119.6
C3—C14—H14A	109.5	C23—C34—H34A	109.5
C3—C14—H14B	109.5	C23—C34—H34B	109.5
H14A—C14—H14B	109.5	H34A—C34—H34B	109.5
C3—C14—H14C	109.5	C23—C34—H34C	109.5
H14A—C14—H14C	109.5	H34A—C34—H34C	109.5
H14B—C14—H14C	109.5	H34B—C34—H34C	109.5
C4—C15—H15A	109.5	C24—C35—H35A	109.5
C4—C15—H15B	109.5	C24—C35—H35B	109.5
H15A—C15—H15B	109.5	H35A—C35—H35B	109.5
C4—C15—H15C	109.5	C24—C35—H35C	109.5
H15A—C15—H15C	109.5	H35A—C35—H35C	109.5
H15B—C15—H15C	109.5	H35B—C35—H35C	109.5
C11—C16—H16A	109.5	C31—C36—H36A	109.5
C11—C16—H16B	109.5	C31—C36—H36B	109.5
H16A—C16—H16B	109.5	H36A—C36—H36B	109.5
C11—C16—H16C	109.5	C31—C36—H36C	109.5
H16A—C16—H16C	109.5	H36A—C36—H36C	109.5
H16B—C16—H16C	109.5	H36B—C36—H36C	109.5
C11—C16—H16D	109.5	C31—C36—H36D	109.5
H16A—C16—H16D	141.1	H36A—C36—H36D	141.1
H16B—C16—H16D	56.3	H36B—C36—H36D	56.3
H16C—C16—H16D	56.3	H36C—C36—H36D	56.3
C11—C16—H16E	109.5	C31—C36—H36E	109.5
H16A—C16—H16E	56.3	H36A—C36—H36E	56.3
H16B—C16—H16E	141.1	H36B—C36—H36E	141.1
H16C—C16—H16E	56.3	H36C—C36—H36E	56.3
H16D—C16—H16E	109.5	H36D—C36—H36E	109.5
C11—C16—H16F	109.5	C31—C36—H36F	109.5
H16A—C16—H16F	56.3	H36A—C36—H36F	56.3
H16B—C16—H16F	56.3	H36B—C36—H36F	56.3
H16C—C16—H16F	141.1	H36C—C36—H36F	141.1
H16D—C16—H16F	109.5	H36D—C36—H36F	109.5
H16E—C16—H16F	109.5	H36E—C36—H36F	109.5
C7—N1—C1	126.38 (10)	C27—N2—C21	127.45 (11)
C7—N1—H1N	116.8	C27—N2—H2N	116.3
C1—N1—H1N	116.8	C21—N2—H2N	116.3
C6—C1—C2—C3	2.1 (2)	C26—C21—C22—C23	−0.1 (2)
N1—C1—C2—C3	−177.99 (11)	N2—C21—C22—C23	−177.00 (12)
C1—C2—C3—C4	−0.5 (2)	C21—C22—C23—C24	0.3 (2)
C1—C2—C3—C14	178.23 (13)	C21—C22—C23—C34	−179.90 (14)
C2—C3—C4—C5	−1.4 (2)	C22—C23—C24—C25	−0.4 (2)
C14—C3—C4—C5	179.87 (14)	C34—C23—C24—C25	179.74 (15)
C2—C3—C4—C15	177.87 (14)	C22—C23—C24—C35	178.91 (14)
C14—C3—C4—C15	−0.8 (2)	C34—C23—C24—C35	−0.9 (2)
C3—C4—C5—C6	1.8 (2)	C23—C24—C25—C26	0.5 (2)
C15—C4—C5—C6	−177.47 (14)	C35—C24—C25—C26	−178.86 (15)
C4—C5—C6—C1	−0.3 (2)	C24—C25—C26—C21	−0.3 (2)
C2—C1—C6—C5	−1.7 (2)	C22—C21—C26—C25	0.2 (2)
N1—C1—C6—C5	178.37 (12)	N2—C21—C26—C25	176.86 (13)
O1—C7—C8—C9	21.3 (2)	O2—C27—C28—C33	148.70 (14)
N1—C7—C8—C9	−157.96 (13)	N2—C27—C28—C33	−31.60 (19)
O1—C7—C8—C13	−158.56 (14)	O2—C27—C28—C29	−30.15 (19)
N1—C7—C8—C13	22.2 (2)	N2—C27—C28—C29	149.55 (13)
C13—C8—C9—C10	−1.8 (2)	C33—C28—C29—C30	2.0 (2)
C7—C8—C9—C10	178.34 (13)	C27—C28—C29—C30	−179.12 (13)
C8—C9—C10—C11	1.6 (2)	C28—C29—C30—C31	−1.6 (2)
C9—C10—C11—C12	−0.2 (2)	C29—C30—C31—C32	0.0 (2)
C9—C10—C11—C16	178.81 (14)	C29—C30—C31—C36	−179.97 (14)
C10—C11—C12—C13	−1.0 (2)	C30—C31—C32—C33	1.4 (2)
C16—C11—C12—C13	180.00 (14)	C36—C31—C32—C33	−178.70 (16)
C11—C12—C13—C8	0.8 (2)	C31—C32—C33—C28	−1.0 (2)
C9—C8—C13—C12	0.6 (2)	C29—C28—C33—C32	−0.6 (2)
C7—C8—C13—C12	−179.55 (13)	C27—C28—C33—C32	−179.50 (13)
O1—C7—N1—C1	−1.9 (2)	O2—C27—N2—C21	0.1 (2)
C8—C7—N1—C1	177.33 (12)	C28—C27—N2—C21	−179.59 (12)
C6—C1—N1—C7	−148.38 (14)	C26—C21—N2—C27	27.1 (2)
C2—C1—N1—C7	31.7 (2)	C22—C21—N2—C27	−156.12 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86	2.29	3.0860 (14)	154
N2—H2N···O1ii	0.86	2.18	3.0101 (14)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86	2.29	3.0860 (14)	154
N2—H2N⋯O1ii	0.86	2.18	3.0101 (14)	162

Symmetry codes: (i) ; (ii) .