Crystal structure and Hirshfeld analysis of diethyl (2E,2′E)-3,3′-[1-(8-phenyl­isoquinolin-1-yl)-1H-indole-2,7-di­yl]diacrylate

In the mol­ecule of title compound, intra­molecular π–π inter­actions between the indole unit and benzene ring help to establish the clip-shaped conformation of the mol­ecule. In the crystal, the mol­ecules are assembled into two-dimensional layers via C—H...O hydrogen bonds, π–π and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.042
• wR factor = 0.118
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given (or Incomplete) ........     Please Check
PLAT125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given .....     Please Do !
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C27      --C28      .        5.5 s.u.
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C26 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10A     ..O1       .       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A      ..O4       .       2.65 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         20 Report

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          2 Report
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as      mixed Check
PLAT300_ALERT_4_G Atom Site Occupancy of C32        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C32'       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C33        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of C33'       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H32A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H32B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H32C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H32D       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H33A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H33B       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H33C       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H33D       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H33E       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H33F       Constrained at        0.5 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         5% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         12 Note
PLAT899_ALERT_4_G SHELXL97  is Deprecated and Succeeded by SHELXL/       2018 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        46% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
  18 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); 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: SHELXTL (Sheldrick, 2008).

Diethyl (2E,2'E)-3,3'-[1-(8-phenylisoquinolin-1-yl)-1H-indole-2,7-diyl]diacrylate

Crystal data

C33H28N2O4	Z = 2
Mr = 516.57	F(000) = 544
Triclinic, P1	Dx = 1.255 Mg m^−3
a = 7.6918 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.299 (2) Å	Cell parameters from 2873 reflections
c = 14.130 (2) Å	θ = 2.4–26.8°
α = 75.026 (2)°	µ = 0.08 mm^−1
β = 81.728 (3)°	T = 296 K
γ = 79.838 (2)°	Block, yellow
V = 1367.1 (4) Å^3	0.25 × 0.22 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer	4787 independent reflections
Radiation source: fine-focus sealed tube	3595 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −8→9
Tmin = 0.980, Tmax = 0.985	k = −15→15
7633 measured reflections	l = −16→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0501P)^2 + 0.2961P] where P = (Fo^2 + 2Fc^2)/3
4787 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 0.19 e Å^−3
12 restraints	Δρmin = −0.17 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
C1	−0.2667 (3)	0.12835 (16)	0.62659 (15)	0.0669 (5)
H1A	−0.2063	0.0785	0.5933	0.080*
C2	−0.3886 (3)	0.2076 (2)	0.58064 (17)	0.0805 (6)
H2A	−0.4085	0.2117	0.5163	0.097*
C3	−0.4814 (3)	0.28071 (18)	0.62914 (18)	0.0781 (6)
H3A	−0.5642	0.3342	0.5979	0.094*
C4	−0.4512 (3)	0.27430 (16)	0.72388 (17)	0.0714 (6)
H4A	−0.5149	0.3231	0.7573	0.086*
C5	−0.3266 (2)	0.19584 (14)	0.77003 (14)	0.0579 (5)
H5A	−0.3061	0.1929	0.8340	0.070*
C6	−0.2320 (2)	0.12148 (13)	0.72222 (13)	0.0492 (4)
C7	−0.1090 (2)	0.03181 (12)	0.77462 (12)	0.0486 (4)
C8	−0.1445 (3)	−0.06862 (14)	0.78380 (15)	0.0645 (5)
H8A	−0.2356	−0.0776	0.7514	0.077*
C9	−0.0479 (3)	−0.15732 (15)	0.84018 (17)	0.0737 (6)
H9A	−0.0704	−0.2240	0.8409	0.088*
C10	0.0779 (3)	−0.14745 (14)	0.89381 (15)	0.0668 (5)
H10A	0.1360	−0.2067	0.9343	0.080*
C11	0.1205 (2)	−0.04680 (13)	0.88805 (13)	0.0530 (4)
C12	0.0358 (2)	0.04292 (12)	0.82278 (11)	0.0439 (4)
C13	0.1124 (2)	0.13686 (12)	0.80938 (12)	0.0444 (4)
C14	0.2831 (3)	0.06566 (16)	0.93629 (15)	0.0661 (5)
H14A	0.3522	0.0754	0.9812	0.079*
C15	0.2454 (3)	−0.03174 (16)	0.94468 (14)	0.0644 (5)
H15A	0.3022	−0.0890	0.9880	0.077*
C16	0.1046 (2)	0.21406 (12)	0.62857 (12)	0.0475 (4)
C17	0.1905 (2)	0.13020 (13)	0.58706 (13)	0.0529 (4)
C18	0.1870 (3)	0.14647 (16)	0.48587 (14)	0.0706 (6)
H18A	0.2414	0.0930	0.4556	0.085*
C19	0.1055 (3)	0.23942 (17)	0.42822 (15)	0.0809 (7)
H19A	0.1028	0.2456	0.3614	0.097*
C20	0.0292 (3)	0.32200 (16)	0.46865 (15)	0.0734 (6)
H20A	−0.0221	0.3846	0.4294	0.088*
C21	0.0296 (2)	0.31074 (13)	0.57007 (13)	0.0556 (4)
C22	−0.0357 (3)	0.37794 (13)	0.63444 (14)	0.0596 (5)
H22A	−0.0906	0.4472	0.6159	0.072*
C23	−0.0048 (2)	0.32418 (12)	0.72834 (13)	0.0513 (4)
C24	−0.0523 (2)	0.35547 (13)	0.82037 (14)	0.0559 (4)
H24A	−0.0273	0.3047	0.8777	0.067*
C25	−0.1282 (3)	0.44978 (15)	0.83035 (15)	0.0655 (5)
H25A	−0.1514	0.5028	0.7743	0.079*
C26	−0.1769 (3)	0.47315 (14)	0.92742 (16)	0.0620 (5)
C27	−0.3135 (4)	0.60395 (19)	1.01189 (17)	0.0965 (8)
H27A	−0.3689	0.5494	1.0600	0.116*
H27B	−0.2107	0.6153	1.0382	0.116*
C28	−0.4373 (3)	0.69986 (18)	0.99332 (18)	0.0925 (8)
H28A	−0.4743	0.7218	1.0536	0.139*
H28B	−0.5390	0.6881	0.9677	0.139*
H28C	−0.3813	0.7537	0.9462	0.139*
C29	0.2884 (2)	0.03339 (13)	0.64329 (13)	0.0532 (4)
H29A	0.3565	0.0398	0.6901	0.064*
C30	0.2869 (3)	−0.06246 (14)	0.63238 (14)	0.0587 (5)
H30A	0.2193	−0.0711	0.5863	0.070*
C31	0.3893 (3)	−0.15528 (14)	0.69115 (14)	0.0594 (5)
C32	0.4348 (4)	−0.34173 (18)	0.7337 (2)	0.1125 (10)	0.50
H32A	0.4220	−0.3423	0.8031	0.135*	0.50
H32B	0.5603	−0.3516	0.7109	0.135*	0.50
C33	0.3476 (11)	−0.4261 (6)	0.7177 (6)	0.122 (3)	0.50
H33A	0.4013	−0.4931	0.7538	0.183*	0.50
H33B	0.3616	−0.4246	0.6488	0.183*	0.50
H33C	0.2235	−0.4150	0.7402	0.183*	0.50
C32'	0.4348 (4)	−0.34173 (18)	0.7337 (2)	0.1125 (10)	0.50
H32C	0.5485	−0.3315	0.7489	0.135*	0.50
H32D	0.3629	−0.3649	0.7952	0.135*	0.50
C33'	0.4613 (11)	−0.4205 (6)	0.6780 (6)	0.123 (3)	0.50
H33D	0.5198	−0.4853	0.7155	0.185*	0.50
H33E	0.5333	−0.3977	0.6174	0.185*	0.50
H33F	0.3484	−0.4312	0.6639	0.185*	0.50
N1	0.07802 (17)	0.22204 (9)	0.72568 (10)	0.0450 (3)
N2	0.22465 (19)	0.15007 (11)	0.86518 (11)	0.0565 (4)
O1	−0.1490 (2)	0.41273 (11)	1.00476 (11)	0.0842 (5)
O2	−0.2587 (2)	0.57132 (11)	0.92002 (10)	0.0829 (5)
O3	0.4949 (2)	−0.15455 (12)	0.74563 (12)	0.0822 (4)
O4	0.3472 (2)	−0.24346 (10)	0.67786 (11)	0.0831 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0716 (13)	0.0773 (13)	0.0607 (12)	−0.0157 (10)	−0.0119 (10)	−0.0266 (10)
C2	0.0833 (15)	0.0984 (17)	0.0651 (14)	−0.0211 (13)	−0.0271 (12)	−0.0129 (13)
C3	0.0634 (13)	0.0787 (15)	0.0846 (16)	−0.0108 (11)	−0.0249 (12)	0.0038 (12)
C4	0.0633 (12)	0.0652 (12)	0.0771 (15)	0.0021 (10)	−0.0026 (11)	−0.0120 (11)
C5	0.0602 (11)	0.0592 (11)	0.0508 (10)	−0.0031 (9)	−0.0021 (9)	−0.0124 (8)
C6	0.0483 (9)	0.0527 (10)	0.0500 (10)	−0.0156 (7)	−0.0014 (8)	−0.0147 (8)
C7	0.0525 (10)	0.0448 (9)	0.0491 (10)	−0.0095 (7)	0.0042 (8)	−0.0158 (7)
C8	0.0677 (12)	0.0551 (11)	0.0759 (13)	−0.0193 (9)	0.0030 (10)	−0.0234 (10)
C9	0.0843 (15)	0.0413 (10)	0.0905 (16)	−0.0173 (10)	0.0150 (13)	−0.0148 (10)
C10	0.0763 (13)	0.0437 (10)	0.0669 (13)	0.0004 (9)	0.0090 (11)	−0.0042 (9)
C11	0.0543 (10)	0.0480 (10)	0.0489 (10)	0.0021 (8)	0.0057 (8)	−0.0103 (8)
C12	0.0480 (9)	0.0402 (8)	0.0418 (9)	−0.0028 (7)	0.0040 (7)	−0.0136 (7)
C13	0.0468 (9)	0.0431 (9)	0.0437 (9)	−0.0007 (7)	−0.0024 (7)	−0.0164 (7)
C14	0.0640 (12)	0.0750 (14)	0.0611 (12)	0.0068 (10)	−0.0208 (10)	−0.0231 (10)
C15	0.0640 (12)	0.0625 (12)	0.0553 (11)	0.0132 (9)	−0.0079 (9)	−0.0077 (9)
C16	0.0547 (10)	0.0426 (9)	0.0473 (10)	−0.0154 (7)	−0.0011 (8)	−0.0113 (7)
C17	0.0621 (11)	0.0493 (10)	0.0500 (10)	−0.0155 (8)	0.0041 (8)	−0.0170 (8)
C18	0.1023 (16)	0.0597 (12)	0.0512 (12)	−0.0169 (11)	0.0054 (11)	−0.0193 (9)
C19	0.130 (2)	0.0674 (13)	0.0451 (11)	−0.0225 (13)	−0.0057 (12)	−0.0101 (10)
C20	0.1067 (17)	0.0536 (11)	0.0566 (12)	−0.0204 (11)	−0.0122 (11)	0.0007 (9)
C21	0.0686 (11)	0.0449 (9)	0.0539 (11)	−0.0169 (8)	−0.0061 (9)	−0.0073 (8)
C22	0.0717 (12)	0.0369 (9)	0.0686 (13)	−0.0089 (8)	−0.0076 (10)	−0.0090 (9)
C23	0.0579 (10)	0.0372 (9)	0.0603 (11)	−0.0068 (7)	−0.0038 (8)	−0.0156 (8)
C24	0.0626 (11)	0.0440 (9)	0.0637 (11)	−0.0046 (8)	−0.0060 (9)	−0.0198 (8)
C25	0.0793 (13)	0.0527 (11)	0.0630 (12)	0.0064 (9)	−0.0089 (10)	−0.0213 (9)
C26	0.0675 (12)	0.0489 (11)	0.0704 (13)	0.0050 (9)	−0.0107 (10)	−0.0226 (10)
C27	0.129 (2)	0.0874 (16)	0.0712 (15)	0.0354 (15)	−0.0210 (14)	−0.0450 (13)
C28	0.1016 (18)	0.0868 (16)	0.0880 (17)	0.0128 (13)	0.0026 (14)	−0.0434 (14)
C29	0.0549 (10)	0.0556 (10)	0.0498 (10)	−0.0072 (8)	0.0066 (8)	−0.0209 (8)
C30	0.0711 (12)	0.0542 (11)	0.0530 (11)	−0.0030 (9)	−0.0060 (9)	−0.0211 (8)
C31	0.0649 (12)	0.0581 (11)	0.0565 (11)	−0.0013 (9)	−0.0013 (9)	−0.0238 (9)
C32	0.169 (3)	0.0536 (14)	0.114 (2)	0.0120 (15)	−0.062 (2)	−0.0116 (14)
C33	0.171 (6)	0.063 (3)	0.126 (5)	−0.012 (4)	−0.035 (5)	−0.007 (3)
C32'	0.169 (3)	0.0536 (14)	0.114 (2)	0.0120 (15)	−0.062 (2)	−0.0116 (14)
C33'	0.151 (6)	0.068 (4)	0.152 (6)	0.019 (4)	−0.049 (5)	−0.035 (4)
N1	0.0526 (8)	0.0371 (7)	0.0476 (8)	−0.0073 (6)	−0.0034 (6)	−0.0147 (6)
N2	0.0544 (9)	0.0595 (9)	0.0605 (9)	−0.0024 (7)	−0.0134 (7)	−0.0229 (8)
O1	0.1208 (13)	0.0566 (8)	0.0690 (10)	0.0082 (8)	−0.0098 (9)	−0.0183 (7)
O2	0.1138 (12)	0.0630 (9)	0.0678 (9)	0.0313 (8)	−0.0199 (8)	−0.0324 (7)
O3	0.0754 (10)	0.0800 (10)	0.0964 (12)	−0.0037 (7)	−0.0272 (9)	−0.0254 (8)
O4	0.1246 (13)	0.0488 (8)	0.0808 (10)	0.0030 (8)	−0.0383 (9)	−0.0200 (7)

Geometric parameters (Å, º)

C1—C2	1.373 (3)	C19—H19A	0.9300
C1—C6	1.392 (2)	C20—C21	1.402 (3)
C1—H1A	0.9300	C20—H20A	0.9300
C2—C3	1.373 (3)	C21—C22	1.417 (3)
C2—H2A	0.9300	C22—C23	1.367 (2)
C3—C4	1.370 (3)	C22—H22A	0.9300
C3—H3A	0.9300	C23—N1	1.402 (2)
C4—C5	1.381 (3)	C23—C24	1.445 (2)
C4—H4A	0.9300	C24—C25	1.320 (2)
C5—C6	1.383 (2)	C24—H24A	0.9300
C5—H5A	0.9300	C25—C26	1.466 (3)
C6—C7	1.488 (2)	C25—H25A	0.9300
C7—C8	1.380 (2)	C26—O1	1.200 (2)
C7—C12	1.433 (2)	C26—O2	1.330 (2)
C8—C9	1.398 (3)	C27—C28	1.440 (3)
C8—H8A	0.9300	C27—O2	1.456 (2)
C9—C10	1.355 (3)	C27—H27A	0.9700
C9—H9A	0.9300	C27—H27B	0.9700
C10—C11	1.413 (3)	C28—H28A	0.9600
C10—H10A	0.9300	C28—H28B	0.9600
C11—C15	1.406 (3)	C28—H28C	0.9600
C11—C12	1.424 (2)	C29—C30	1.325 (2)
C12—C13	1.431 (2)	C29—H29A	0.9300
C13—N2	1.311 (2)	C30—C31	1.466 (3)
C13—N1	1.430 (2)	C30—H30A	0.9300
C14—C15	1.349 (3)	C31—O3	1.200 (2)
C14—N2	1.357 (2)	C31—O4	1.335 (2)
C14—H14A	0.9300	C32—O4	1.447 (3)
C15—H15A	0.9300	C32—C33	1.483 (8)
C16—N1	1.387 (2)	C32—H32A	0.9700
C16—C17	1.411 (2)	C32—H32B	0.9700
C16—C21	1.413 (2)	C33—H33A	0.9600
C17—C18	1.393 (3)	C33—H33B	0.9600
C17—C29	1.469 (2)	C33—H33C	0.9600
C18—C19	1.392 (3)	C33'—H33D	0.9600
C18—H18A	0.9300	C33'—H33E	0.9600
C19—C20	1.370 (3)	C33'—H33F	0.9600
C2—C1—C6	121.0 (2)	C20—C21—C16	119.45 (17)
C2—C1—H1A	119.5	C20—C21—C22	133.75 (18)
C6—C1—H1A	119.5	C16—C21—C22	106.78 (16)
C1—C2—C3	120.4 (2)	C23—C22—C21	108.75 (15)
C1—C2—H2A	119.8	C23—C22—H22A	125.6
C3—C2—H2A	119.8	C21—C22—H22A	125.6
C4—C3—C2	119.5 (2)	C22—C23—N1	108.15 (15)
C4—C3—H3A	120.3	C22—C23—C24	130.46 (16)
C2—C3—H3A	120.3	N1—C23—C24	121.29 (15)
C3—C4—C5	120.4 (2)	C25—C24—C23	125.78 (18)
C3—C4—H4A	119.8	C25—C24—H24A	117.1
C5—C4—H4A	119.8	C23—C24—H24A	117.1
C4—C5—C6	120.80 (18)	C24—C25—C26	121.80 (19)
C4—C5—H5A	119.6	C24—C25—H25A	119.1
C6—C5—H5A	119.6	C26—C25—H25A	119.1
C5—C6—C1	117.88 (17)	O1—C26—O2	123.11 (18)
C5—C6—C7	120.82 (16)	O1—C26—C25	125.45 (17)
C1—C6—C7	121.08 (16)	O2—C26—C25	111.44 (17)
C8—C7—C12	117.69 (16)	C28—C27—O2	109.01 (19)
C8—C7—C6	117.81 (16)	C28—C27—H27A	109.9
C12—C7—C6	124.32 (14)	O2—C27—H27A	109.9
C7—C8—C9	122.14 (19)	C28—C27—H27B	109.9
C7—C8—H8A	118.9	O2—C27—H27B	109.9
C9—C8—H8A	118.9	H27A—C27—H27B	108.3
C10—C9—C8	120.86 (18)	C27—C28—H28A	109.5
C10—C9—H9A	119.6	C27—C28—H28B	109.5
C8—C9—H9A	119.6	H28A—C28—H28B	109.5
C9—C10—C11	119.79 (18)	C27—C28—H28C	109.5
C9—C10—H10A	120.1	H28A—C28—H28C	109.5
C11—C10—H10A	120.1	H28B—C28—H28C	109.5
C15—C11—C10	122.10 (17)	C30—C29—C17	124.97 (17)
C15—C11—C12	118.29 (16)	C30—C29—H29A	117.5
C10—C11—C12	119.61 (18)	C17—C29—H29A	117.5
C11—C12—C13	114.52 (15)	C29—C30—C31	121.64 (18)
C11—C12—C7	119.21 (14)	C29—C30—H30A	119.2
C13—C12—C7	126.23 (14)	C31—C30—H30A	119.2
N2—C13—N1	115.16 (14)	O3—C31—O4	123.31 (18)
N2—C13—C12	125.01 (15)	O3—C31—C30	125.94 (18)
N1—C13—C12	119.66 (14)	O4—C31—C30	110.74 (17)
C15—C14—N2	122.84 (18)	O4—C32—C33	106.4 (4)
C15—C14—H14A	118.6	O4—C32—H32A	110.4
N2—C14—H14A	118.6	C33—C32—H32A	110.4
C14—C15—C11	120.14 (17)	O4—C32—H32B	110.4
C14—C15—H15A	119.9	C33—C32—H32B	110.4
C11—C15—H15A	119.9	H32A—C32—H32B	108.6
N1—C16—C17	130.45 (15)	C32—C33—H33A	109.5
N1—C16—C21	107.63 (14)	C32—C33—H33B	109.5
C17—C16—C21	121.91 (16)	H33A—C33—H33B	109.5
C18—C17—C16	115.80 (17)	C32—C33—H33C	109.5
C18—C17—C29	120.48 (16)	H33A—C33—H33C	109.5
C16—C17—C29	123.62 (16)	H33B—C33—H33C	109.5
C19—C18—C17	122.75 (18)	H33D—C33'—H33E	109.5
C19—C18—H18A	118.6	H33D—C33'—H33F	109.5
C17—C18—H18A	118.6	H33E—C33'—H33F	109.5
C20—C19—C18	120.90 (19)	C16—N1—C23	108.62 (13)
C20—C19—H19A	119.6	C16—N1—C13	125.19 (12)
C18—C19—H19A	119.6	C23—N1—C13	125.88 (13)
C19—C20—C21	119.03 (19)	C13—N2—C14	117.40 (16)
C19—C20—H20A	120.5	C26—O2—C27	116.55 (16)
C21—C20—H20A	120.5	C31—O4—C32	116.81 (18)
C6—C1—C2—C3	−1.2 (3)	C19—C20—C21—C16	−1.5 (3)
C1—C2—C3—C4	0.2 (3)	C19—C20—C21—C22	−179.9 (2)
C2—C3—C4—C5	0.9 (3)	N1—C16—C21—C20	−176.43 (16)
C3—C4—C5—C6	−0.9 (3)	C17—C16—C21—C20	4.4 (3)
C4—C5—C6—C1	−0.1 (3)	N1—C16—C21—C22	2.38 (19)
C4—C5—C6—C7	−174.84 (16)	C17—C16—C21—C22	−176.77 (16)
C2—C1—C6—C5	1.2 (3)	C20—C21—C22—C23	177.6 (2)
C2—C1—C6—C7	175.87 (17)	C16—C21—C22—C23	−1.0 (2)
C5—C6—C7—C8	118.61 (19)	C21—C22—C23—N1	−0.8 (2)
C1—C6—C7—C8	−56.0 (2)	C21—C22—C23—C24	−176.96 (18)
C5—C6—C7—C12	−56.3 (2)	C22—C23—C24—C25	−5.2 (3)
C1—C6—C7—C12	129.10 (18)	N1—C23—C24—C25	179.04 (18)
C12—C7—C8—C9	1.9 (3)	C23—C24—C25—C26	177.95 (18)
C6—C7—C8—C9	−173.33 (17)	C24—C25—C26—O1	2.5 (3)
C7—C8—C9—C10	4.4 (3)	C24—C25—C26—O2	−177.10 (18)
C8—C9—C10—C11	−4.1 (3)	C18—C17—C29—C30	−43.1 (3)
C9—C10—C11—C15	177.73 (18)	C16—C17—C29—C30	140.80 (19)
C9—C10—C11—C12	−2.6 (3)	C17—C29—C30—C31	179.64 (16)
C15—C11—C12—C13	10.8 (2)	C29—C30—C31—O3	−7.9 (3)
C10—C11—C12—C13	−168.87 (15)	C29—C30—C31—O4	170.90 (17)
C15—C11—C12—C7	−171.45 (15)	C17—C16—N1—C23	176.17 (17)
C10—C11—C12—C7	8.8 (2)	C21—C16—N1—C23	−2.89 (18)
C8—C7—C12—C11	−8.4 (2)	C17—C16—N1—C13	−9.9 (3)
C6—C7—C12—C11	166.54 (15)	C21—C16—N1—C13	171.01 (14)
C8—C7—C12—C13	169.00 (16)	C22—C23—N1—C16	2.29 (19)
C6—C7—C12—C13	−16.1 (2)	C24—C23—N1—C16	178.89 (15)
C11—C12—C13—N2	−14.1 (2)	C22—C23—N1—C13	−171.56 (15)
C7—C12—C13—N2	168.39 (15)	C24—C23—N1—C13	5.0 (2)
C11—C12—C13—N1	161.00 (13)	N2—C13—N1—C16	122.36 (16)
C7—C12—C13—N1	−16.5 (2)	C12—C13—N1—C16	−53.2 (2)
N2—C14—C15—C11	−9.5 (3)	N2—C13—N1—C23	−64.8 (2)
C10—C11—C15—C14	179.47 (17)	C12—C13—N1—C23	119.66 (17)
C12—C11—C15—C14	−0.2 (3)	N1—C13—N2—C14	−169.93 (14)
N1—C16—C17—C18	177.25 (17)	C12—C13—N2—C14	5.4 (2)
C21—C16—C17—C18	−3.8 (2)	C15—C14—N2—C13	7.0 (3)
N1—C16—C17—C29	−6.5 (3)	O1—C26—O2—C27	0.5 (3)
C21—C16—C17—C29	172.48 (16)	C25—C26—O2—C27	−179.9 (2)
C16—C17—C18—C19	0.4 (3)	C28—C27—O2—C26	−165.3 (2)
C29—C17—C18—C19	−175.98 (19)	O3—C31—O4—C32	0.5 (3)
C17—C18—C19—C20	2.4 (3)	C30—C31—O4—C32	−178.3 (2)
C18—C19—C20—C21	−1.8 (3)	C33—C32—O4—C31	171.9 (4)

Hydrogen-bond geometry (Å, º)

Cg3 is the centroid of the N2/C11–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O3^i	0.93	2.49	3.3404 (5)	152
C10—H10A···O1^ii	0.93	2.64	3.4252 (5)	143
C2—H2A···O4^iii	0.93	2.65	3.5339 (6)	159
C29—H29A···Cg3	0.93	2.86	3.370 (2)	116

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