Three polymorphs of a new N,N′-di­propyl­ated isoindigo derivative

A newly synthesized N,N′-dipropyl-substituted isoindigo derivative, namely, 1-propyl-3-(1-propyl-1,2-di­hydro-2-oxo-3H-indol-3-yl­idene)-1,3-di­hydro-2H-in­dol-2-one, C₂₂H₂₂N₂O₂, was found to have three polymorphic forms (denoted Forms I, II and III) under various crystallization conditions. Crystal structure analysis indicated that Form III had a significantly different mol­ecular conformation from the other two polymorphs. Their different packing arrangements were correlated with differences in the inter­molecular inter­actions. Thermal measurements revealed that Forms I and II are enanti­otropically related, and Form II exhibits thermally dynamic behaviour.

Computing details

1-Propyl-3-(1-propyl-1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-2H-indol-2-one (Form_I)

Crystal data

C22H22N2O2	F(000) = 368
Mr = 346.41	Dx = 1.301 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 12.8456 (2) Å	Cell parameters from 3025 reflections
b = 5.5803 (1) Å	θ = 4.7–74.5°
c = 16.7446 (3) Å	µ = 0.67 mm^−1
β = 132.566 (1)°	T = 223 K
V = 884.01 (3) Å^3	Block, dull dark red
Z = 2	0.40 × 0.30 × 0.25 mm

Data collection

XtaLAB AFC12 (RINC) Kappa dual home/near diffractometer	1535 reflections with I > 2σ(I)
Radiation source: micro-focus sealed X-ray tube, Rigaku (Cu) X-ray Source	Rint = 0.069
Mirror monochromator	θmax = 75.1°, θmin = 4.7°
Detector resolution: 5.8140 pixels mm^-1	h = −15→14
ω scans	k = −6→6
4261 measured reflections	l = −20→19
1759 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.0893P)^2 + 0.062P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.159	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.19 e Å^−3
1759 reflections	Δρmin = −0.17 e Å^−3
120 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.011 (2)
Primary atom site location: dual

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.

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

	x	y	z	Uiso*/Ueq
O1	0.22087 (11)	0.0744 (2)	0.33166 (9)	0.0655 (4)
N1	0.29921 (13)	0.3704 (2)	0.45455 (10)	0.0508 (4)
C8	0.53039 (15)	0.2622 (2)	0.59591 (11)	0.0468 (4)
C3	0.42327 (16)	0.4276 (2)	0.55897 (12)	0.0480 (4)
C2	0.31708 (15)	0.1689 (3)	0.41834 (11)	0.0484 (4)
C1	0.47079 (14)	0.0931 (2)	0.50603 (11)	0.0452 (4)
C4	0.44401 (19)	0.6179 (3)	0.62170 (13)	0.0565 (4)
H4	0.371094	0.727811	0.594458	0.068*
C7	0.66029 (17)	0.2889 (3)	0.70122 (13)	0.0602 (5)
H7	0.733899	0.179727	0.729554	0.072*
C9	0.16559 (18)	0.4990 (3)	0.39196 (13)	0.0610 (5)
H9a	0.101931	0.444850	0.316426	0.073*
H9b	0.182921	0.670472	0.392998	0.073*
C5	0.5742 (2)	0.6412 (3)	0.72484 (14)	0.0631 (5)
H5	0.591110	0.768971	0.768911	0.076*
C10	0.09383 (17)	0.4630 (4)	0.43456 (14)	0.0675 (5)
H10a	0.154600	0.528010	0.508246	0.081*
H10b	0.005120	0.553621	0.389069	0.081*
C6	0.68017 (19)	0.4786 (4)	0.76408 (14)	0.0676 (5)
H6	0.768099	0.496358	0.835170	0.081*
C11	0.0625 (2)	0.2049 (4)	0.43661 (16)	0.0774 (6)
H11a	−0.001595	0.141334	0.363410	0.116*
H11b	0.019037	0.193115	0.466394	0.116*
H11c	0.149734	0.113673	0.481351	0.116*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0506 (6)	0.0680 (8)	0.0541 (7)	−0.0041 (5)	0.0260 (6)	−0.0160 (5)
N1	0.0541 (7)	0.0454 (7)	0.0507 (7)	−0.0022 (5)	0.0345 (6)	−0.0011 (5)
C8	0.0523 (8)	0.0481 (8)	0.0485 (8)	−0.0122 (6)	0.0375 (7)	−0.0076 (6)
C3	0.0583 (8)	0.0430 (7)	0.0505 (8)	−0.0095 (6)	0.0399 (7)	−0.0021 (6)
C2	0.0503 (7)	0.0489 (7)	0.0456 (8)	−0.0072 (6)	0.0323 (7)	−0.0045 (6)
C1	0.0470 (7)	0.0475 (7)	0.0438 (7)	−0.0108 (5)	0.0318 (6)	−0.0055 (5)
C4	0.0731 (10)	0.0441 (8)	0.0621 (10)	−0.0056 (7)	0.0496 (9)	−0.0047 (6)
C7	0.0535 (8)	0.0740 (11)	0.0523 (9)	−0.0095 (7)	0.0354 (8)	−0.0180 (7)
C9	0.0655 (10)	0.0515 (9)	0.0554 (9)	0.0098 (7)	0.0367 (8)	0.0088 (7)
C5	0.0798 (11)	0.0580 (9)	0.0645 (10)	−0.0177 (8)	0.0540 (10)	−0.0198 (8)
C10	0.0570 (9)	0.0762 (12)	0.0590 (10)	0.0139 (8)	0.0351 (9)	0.0023 (8)
C6	0.0619 (9)	0.0839 (12)	0.0547 (9)	−0.0176 (9)	0.0386 (8)	−0.0266 (9)
C11	0.0660 (10)	0.0950 (15)	0.0712 (12)	−0.0013 (10)	0.0464 (10)	0.0076 (10)

Geometric parameters (Å, º)

O1—C2	1.2186 (17)	C7—C6	1.389 (2)
N1—C3	1.3889 (18)	C9—H9a	0.9800
N1—C2	1.369 (2)	C9—H9b	0.9800
N1—C9	1.4579 (19)	C9—C10	1.513 (3)
C8—C3	1.406 (2)	C5—H5	0.9400
C8—C1	1.4775 (18)	C5—C6	1.377 (3)
C8—C7	1.391 (2)	C10—H10a	0.9800
C3—C4	1.387 (2)	C10—H10b	0.9800
C2—C1	1.5203 (19)	C10—C11	1.502 (3)
C1—C1^i	1.374 (3)	C6—H6	0.9400
C4—H4	0.9400	C11—H11a	0.9700
C4—C5	1.375 (2)	C11—H11b	0.9700
C7—H7	0.9400	C11—H11c	0.9700
C3—N1—C9	125.61 (13)	N1—C9—C10	113.10 (13)
C2—N1—C3	110.67 (12)	H9a—C9—H9b	107.8
C2—N1—C9	123.68 (13)	C10—C9—H9a	109.0
C3—C8—C1	107.02 (12)	C10—C9—H9b	109.0
C7—C8—C3	117.72 (13)	C4—C5—H5	119.8
C7—C8—C1	135.27 (14)	C4—C5—C6	120.46 (15)
N1—C3—C8	110.56 (12)	C6—C5—H5	119.8
C4—C3—N1	126.76 (15)	C9—C10—H10a	108.9
C4—C3—C8	122.69 (15)	C9—C10—H10b	108.9
O1—C2—N1	122.96 (14)	H10a—C10—H10b	107.7
O1—C2—C1	129.67 (14)	C11—C10—C9	113.36 (15)
N1—C2—C1	107.35 (12)	C11—C10—H10a	108.9
C8—C1—C2	104.23 (12)	C11—C10—H10b	108.9
C1^i—C1—C8	132.41 (16)	C7—C6—H6	119.2
C1^i—C1—C2	123.36 (15)	C5—C6—C7	121.64 (16)
C3—C4—H4	120.9	C5—C6—H6	119.2
C5—C4—C3	118.10 (16)	C10—C11—H11a	109.5
C5—C4—H4	120.9	C10—C11—H11b	109.5
C8—C7—H7	120.3	C10—C11—H11c	109.5
C6—C7—C8	119.36 (16)	H11a—C11—H11b	109.5
C6—C7—H7	120.3	H11a—C11—H11c	109.5
N1—C9—H9a	109.0	H11b—C11—H11c	109.5
N1—C9—H9b	109.0
O1—C2—C1—C8	−173.83 (15)	C2—N1—C3—C8	0.43 (16)
O1—C2—C1—C1^i	6.9 (3)	C2—N1—C3—C4	−179.26 (13)
N1—C3—C4—C5	178.34 (13)	C2—N1—C9—C10	106.74 (17)
N1—C2—C1—C8	4.26 (15)	C1—C8—C3—N1	2.40 (15)
N1—C2—C1—C1^i	−175.04 (15)	C1—C8—C3—C4	−177.90 (13)
N1—C9—C10—C11	−58.6 (2)	C1—C8—C7—C6	178.58 (16)
C8—C3—C4—C5	−1.3 (2)	C4—C5—C6—C7	0.8 (3)
C8—C7—C6—C5	0.1 (3)	C7—C8—C3—N1	−177.50 (12)
C3—N1—C2—O1	175.25 (13)	C7—C8—C3—C4	2.2 (2)
C3—N1—C2—C1	−3.00 (16)	C7—C8—C1—C2	175.91 (16)
C3—N1—C9—C10	−70.85 (19)	C7—C8—C1—C1^i	−4.9 (3)
C3—C8—C1—C2	−3.97 (14)	C9—N1—C3—C8	178.28 (13)
C3—C8—C1—C1^i	175.25 (18)	C9—N1—C3—C4	−1.4 (2)
C3—C8—C7—C6	−1.6 (2)	C9—N1—C2—O1	−2.7 (2)
C3—C4—C5—C6	−0.2 (2)	C9—N1—C2—C1	179.10 (12)

Symmetry code: (i) −x+1, −y, −z+1.

1-Propyl-3-(1-propyl-1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-2H-indol-2-one (Form_II)

Crystal data

C22H22N2O2	F(000) = 1472
Mr = 346.41	Dx = 1.308 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 35.4947 (9) Å	Cell parameters from 5948 reflections
b = 5.5238 (1) Å	θ = 4.8–74.3°
c = 18.9927 (4) Å	µ = 0.67 mm^−1
β = 109.151 (2)°	T = 223 K
V = 3517.73 (14) Å^3	Needle, dull dark red
Z = 8	1 × 0.11 × 0.06 mm

Data collection

XtaLAB AFC12 (RINC) Kappa dual offset/far diffractometer	3518 independent reflections
Radiation source: micro-focus sealed X-ray tube, Rigaku (Cu) X-ray Source	3113 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 5.8140 pixels mm^-1	θmax = 75.2°, θmin = 4.8°
ω scans	h = −43→44
Absorption correction: multi-scan CrysAlis PRO; Rigaku OD, 2019)	k = −6→6
Tmin = 0.817, Tmax = 1.000	l = −23→23
9278 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.1061P)^2 + 0.5262P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.152	(Δ/σ)max = 0.002
S = 1.05	Δρmax = 0.25 e Å^−3
3518 reflections	Δρmin = −0.23 e Å^−3
238 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00101 (15)
Primary atom site location: dual

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.

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

	x	y	z	Uiso*/Ueq
O1	0.63730 (3)	0.27171 (19)	0.83154 (5)	0.0592 (3)
O2	0.61174 (3)	0.3533 (2)	0.53628 (5)	0.0612 (3)
N1	0.59659 (3)	−0.03824 (19)	0.77483 (5)	0.0443 (3)
N2	0.65393 (3)	0.65684 (19)	0.59344 (6)	0.0464 (3)
C1	0.61464 (3)	0.2200 (2)	0.69428 (6)	0.0399 (3)
C3	0.57628 (3)	−0.1136 (2)	0.70218 (6)	0.0409 (3)
C12	0.63529 (3)	0.4009 (2)	0.67389 (6)	0.0404 (3)
C8	0.58551 (3)	0.0398 (2)	0.65104 (6)	0.0408 (3)
C19	0.66452 (3)	0.5806 (2)	0.71726 (6)	0.0425 (3)
C2	0.61876 (3)	0.1628 (2)	0.77486 (6)	0.0427 (3)
C14	0.67413 (3)	0.7322 (2)	0.66610 (7)	0.0428 (3)
C13	0.63096 (3)	0.4584 (2)	0.59320 (6)	0.0441 (3)
C4	0.55074 (4)	−0.3089 (2)	0.68118 (7)	0.0498 (3)
H4	0.545783	−0.410194	0.716932	0.060*
C15	0.69986 (4)	0.9271 (2)	0.68733 (8)	0.0524 (3)
H15	0.705352	1.026099	0.651616	0.063*
C9	0.59376 (4)	−0.1501 (2)	0.84255 (7)	0.0533 (3)
H9a	0.614651	−0.082747	0.885665	0.064*
H9b	0.598716	−0.324246	0.840964	0.064*
C5	0.53267 (4)	−0.3505 (3)	0.60557 (8)	0.0567 (4)
H5	0.515196	−0.482301	0.589425	0.068*
C20	0.65649 (4)	0.7721 (3)	0.52599 (8)	0.0553 (3)
H20a	0.653714	0.947611	0.530119	0.066*
H20b	0.634229	0.715933	0.483179	0.066*
C18	0.68318 (4)	0.6282 (3)	0.79280 (7)	0.0562 (4)
H18	0.678186	0.528895	0.828967	0.067*
C21	0.69528 (4)	0.7197 (3)	0.51183 (8)	0.0599 (4)
H21a	0.695629	0.808848	0.467433	0.072*
H21b	0.717537	0.778549	0.554199	0.072*
C16	0.71731 (4)	0.9719 (3)	0.76299 (9)	0.0573 (4)
H16	0.734693	1.104116	0.779136	0.069*
C7	0.56636 (4)	−0.0063 (3)	0.57552 (7)	0.0583 (4)
H7	0.571152	0.093440	0.539268	0.070*
C17	0.70924 (4)	0.8234 (3)	0.81446 (8)	0.0620 (4)
H17	0.721639	0.854567	0.865511	0.074*
C6	0.54018 (4)	−0.2000 (3)	0.55412 (8)	0.0643 (4)
H6	0.527256	−0.229012	0.503099	0.077*
C10	0.55374 (5)	−0.1129 (3)	0.85314 (8)	0.0595 (4)
H10a	0.533327	−0.198164	0.813272	0.071*
H10b	0.554550	−0.186347	0.900585	0.071*
C22	0.70128 (5)	0.4536 (3)	0.50062 (9)	0.0657 (4)
H22a	0.678971	0.393025	0.459609	0.099*
H22b	0.702922	0.365674	0.545738	0.099*
H22c	0.725787	0.431252	0.489311	0.099*
C11	0.54160 (6)	0.1482 (3)	0.85300 (10)	0.0745 (5)
H11a	0.540499	0.222691	0.806111	0.112*
H11b	0.560937	0.232889	0.893774	0.112*
H11c	0.515533	0.157367	0.859010	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0704 (6)	0.0688 (6)	0.0370 (5)	−0.0232 (5)	0.0155 (4)	−0.0157 (4)
O2	0.0734 (6)	0.0706 (6)	0.0389 (5)	−0.0244 (5)	0.0175 (4)	−0.0125 (4)
N1	0.0477 (5)	0.0472 (6)	0.0369 (5)	−0.0041 (4)	0.0121 (4)	−0.0052 (4)
N2	0.0477 (6)	0.0458 (6)	0.0428 (5)	−0.0025 (4)	0.0109 (4)	−0.0008 (4)
C1	0.0353 (5)	0.0495 (6)	0.0360 (5)	−0.0022 (4)	0.0133 (4)	−0.0120 (4)
C3	0.0367 (5)	0.0431 (6)	0.0418 (6)	0.0019 (4)	0.0116 (5)	−0.0101 (5)
C12	0.0357 (5)	0.0492 (6)	0.0368 (5)	−0.0018 (4)	0.0127 (4)	−0.0119 (4)
C8	0.0353 (5)	0.0495 (6)	0.0392 (6)	−0.0031 (4)	0.0145 (4)	−0.0123 (5)
C19	0.0339 (5)	0.0488 (6)	0.0458 (6)	−0.0018 (4)	0.0146 (5)	−0.0129 (5)
C2	0.0413 (6)	0.0492 (6)	0.0381 (6)	−0.0026 (5)	0.0135 (5)	−0.0097 (5)
C14	0.0366 (5)	0.0406 (6)	0.0490 (6)	0.0040 (4)	0.0110 (5)	−0.0061 (5)
C13	0.0435 (6)	0.0487 (6)	0.0407 (6)	−0.0020 (5)	0.0147 (5)	−0.0065 (5)
C4	0.0509 (7)	0.0448 (6)	0.0528 (7)	−0.0048 (5)	0.0155 (6)	−0.0076 (5)
C15	0.0483 (7)	0.0410 (6)	0.0633 (8)	−0.0017 (5)	0.0121 (6)	−0.0028 (5)
C9	0.0627 (8)	0.0504 (7)	0.0414 (6)	−0.0034 (6)	0.0097 (5)	0.0033 (5)
C5	0.0521 (7)	0.0577 (8)	0.0586 (8)	−0.0152 (6)	0.0161 (6)	−0.0209 (6)
C20	0.0611 (8)	0.0486 (7)	0.0498 (7)	−0.0004 (6)	0.0096 (6)	0.0095 (5)
C18	0.0485 (7)	0.0756 (9)	0.0454 (7)	−0.0186 (6)	0.0167 (5)	−0.0175 (6)
C21	0.0626 (8)	0.0685 (9)	0.0475 (7)	−0.0128 (7)	0.0166 (6)	0.0108 (6)
C16	0.0461 (7)	0.0512 (7)	0.0699 (9)	−0.0088 (5)	0.0125 (6)	−0.0165 (6)
C7	0.0562 (7)	0.0798 (10)	0.0390 (6)	−0.0240 (7)	0.0159 (5)	−0.0161 (6)
C17	0.0510 (7)	0.0780 (10)	0.0540 (7)	−0.0191 (7)	0.0130 (6)	−0.0240 (7)
C6	0.0608 (8)	0.0847 (10)	0.0450 (7)	−0.0269 (7)	0.0144 (6)	−0.0250 (7)
C10	0.0691 (9)	0.0686 (9)	0.0432 (6)	−0.0131 (7)	0.0219 (6)	0.0024 (6)
C22	0.0649 (8)	0.0777 (10)	0.0577 (8)	0.0049 (7)	0.0245 (7)	0.0069 (7)
C11	0.0768 (10)	0.0855 (11)	0.0705 (10)	0.0061 (9)	0.0368 (8)	−0.0027 (8)

Geometric parameters (Å, º)

O1—C2	1.2201 (14)	C5—H5	0.9400
O2—C13	1.2196 (15)	C5—C6	1.374 (2)
N1—C3	1.3944 (14)	C20—H20a	0.9800
N1—C2	1.3608 (16)	C20—H20b	0.9800
N1—C9	1.4599 (16)	C20—C21	1.515 (2)
N2—C14	1.3938 (15)	C18—H18	0.9400
N2—C13	1.3651 (16)	C18—C17	1.3923 (19)
N2—C20	1.4599 (17)	C21—H21a	0.9800
C1—C12	1.3679 (18)	C21—H21b	0.9800
C1—C8	1.4757 (15)	C21—C22	1.510 (2)
C1—C2	1.5222 (15)	C16—H16	0.9400
C3—C8	1.4064 (17)	C16—C17	1.376 (2)
C3—C4	1.3810 (17)	C7—H7	0.9400
C12—C19	1.4763 (15)	C7—C6	1.3876 (19)
C12—C13	1.5226 (16)	C17—H17	0.9400
C8—C7	1.3944 (16)	C6—H6	0.9400
C19—C14	1.4068 (18)	C10—H10a	0.9800
C19—C18	1.3938 (16)	C10—H10b	0.9800
C14—C15	1.3839 (17)	C10—C11	1.505 (2)
C4—H4	0.9400	C22—H22a	0.9700
C4—C5	1.3864 (18)	C22—H22b	0.9700
C15—H15	0.9400	C22—H22c	0.9700
C15—C16	1.388 (2)	C11—H11a	0.9700
C9—H9a	0.9800	C11—H11b	0.9700
C9—H9b	0.9800	C11—H11c	0.9700
C9—C10	1.513 (2)
C3—N1—C9	125.64 (10)	N2—C20—H20a	108.9
C2—N1—C3	110.82 (10)	N2—C20—H20b	108.9
C2—N1—C9	123.50 (10)	N2—C20—C21	113.22 (11)
C14—N2—C20	125.36 (11)	H20a—C20—H20b	107.7
C13—N2—C14	110.82 (10)	C21—C20—H20a	108.9
C13—N2—C20	123.81 (10)	C21—C20—H20b	108.9
C12—C1—C8	132.67 (10)	C19—C18—H18	120.1
C12—C1—C2	123.55 (10)	C17—C18—C19	119.70 (13)
C8—C1—C2	103.77 (10)	C17—C18—H18	120.1
N1—C3—C8	109.96 (10)	C20—C21—H21a	109.0
C4—C3—N1	126.62 (12)	C20—C21—H21b	109.0
C4—C3—C8	123.41 (11)	H21a—C21—H21b	107.8
C1—C12—C19	132.58 (10)	C22—C21—C20	112.92 (12)
C1—C12—C13	123.42 (10)	C22—C21—H21a	109.0
C19—C12—C13	103.99 (10)	C22—C21—H21b	109.0
C3—C8—C1	107.56 (9)	C15—C16—H16	119.9
C7—C8—C1	135.38 (11)	C17—C16—C15	120.19 (12)
C7—C8—C3	117.06 (11)	C17—C16—H16	119.9
C14—C19—C12	107.46 (10)	C8—C7—H7	120.1
C18—C19—C12	135.31 (12)	C6—C7—C8	119.72 (13)
C18—C19—C14	117.24 (11)	C6—C7—H7	120.1
O1—C2—N1	123.17 (11)	C18—C17—H17	119.2
O1—C2—C1	129.10 (12)	C16—C17—C18	121.66 (13)
N1—C2—C1	107.71 (9)	C16—C17—H17	119.2
N2—C14—C19	110.11 (10)	C5—C6—C7	121.72 (13)
C15—C14—N2	126.63 (12)	C5—C6—H6	119.1
C15—C14—C19	123.26 (12)	C7—C6—H6	119.1
O2—C13—N2	123.02 (11)	C9—C10—H10a	108.7
O2—C13—C12	129.43 (12)	C9—C10—H10b	108.7
N2—C13—C12	107.54 (9)	H10a—C10—H10b	107.6
C3—C4—H4	121.1	C11—C10—C9	114.26 (13)
C3—C4—C5	117.75 (13)	C11—C10—H10a	108.7
C5—C4—H4	121.1	C11—C10—H10b	108.7
C14—C15—H15	121.0	C21—C22—H22a	109.5
C14—C15—C16	117.91 (13)	C21—C22—H22b	109.5
C16—C15—H15	121.0	C21—C22—H22c	109.5
N1—C9—H9a	108.9	H22a—C22—H22b	109.5
N1—C9—H9b	108.9	H22a—C22—H22c	109.5
N1—C9—C10	113.50 (11)	H22b—C22—H22c	109.5
H9a—C9—H9b	107.7	C10—C11—H11a	109.5
C10—C9—H9a	108.9	C10—C11—H11b	109.5
C10—C9—H9b	108.9	C10—C11—H11c	109.5
C4—C5—H5	119.9	H11a—C11—H11b	109.5
C6—C5—C4	120.29 (12)	H11a—C11—H11c	109.5
C6—C5—H5	119.9	H11b—C11—H11c	109.5
N1—C3—C8—C1	1.87 (13)	C19—C18—C17—C16	−0.2 (2)
N1—C3—C8—C7	−177.73 (10)	C2—N1—C3—C8	0.99 (13)
N1—C3—C4—C5	178.52 (11)	C2—N1—C3—C4	−179.19 (11)
N1—C9—C10—C11	−55.90 (16)	C2—N1—C9—C10	108.04 (14)
N2—C14—C15—C16	−179.64 (11)	C2—C1—C12—C19	−0.6 (2)
N2—C20—C21—C22	61.62 (16)	C2—C1—C12—C13	−179.70 (10)
C1—C12—C19—C14	−176.47 (12)	C2—C1—C8—C3	−3.63 (12)
C1—C12—C19—C18	3.4 (2)	C2—C1—C8—C7	175.86 (14)
C1—C12—C13—O2	−4.8 (2)	C14—N2—C13—O2	−176.90 (12)
C1—C12—C13—N2	176.40 (11)	C14—N2—C13—C12	2.01 (13)
C1—C8—C7—C6	179.22 (13)	C14—N2—C20—C21	74.72 (16)
C3—N1—C2—O1	175.40 (11)	C14—C19—C18—C17	1.68 (19)
C3—N1—C2—C1	−3.32 (13)	C14—C15—C16—C17	0.7 (2)
C3—N1—C9—C10	−69.30 (16)	C13—N2—C14—C19	−0.23 (13)
C3—C8—C7—C6	−1.3 (2)	C13—N2—C14—C15	−179.78 (11)
C3—C4—C5—C6	−0.2 (2)	C13—N2—C20—C21	−105.42 (14)
C12—C1—C8—C3	175.66 (12)	C13—C12—C19—C14	2.74 (12)
C12—C1—C8—C7	−4.8 (2)	C13—C12—C19—C18	−177.36 (14)
C12—C1—C2—O1	6.3 (2)	C4—C3—C8—C1	−177.96 (10)
C12—C1—C2—N1	−175.13 (11)	C4—C3—C8—C7	2.44 (18)
C12—C19—C14—N2	−1.71 (12)	C4—C5—C6—C7	1.3 (2)
C12—C19—C14—C15	177.86 (10)	C15—C16—C17—C18	−1.1 (2)
C12—C19—C18—C17	−178.21 (13)	C9—N1—C3—C8	178.61 (11)
C8—C1—C12—C19	−179.78 (11)	C9—N1—C3—C4	−1.56 (19)
C8—C1—C12—C13	1.1 (2)	C9—N1—C2—O1	−2.29 (19)
C8—C1—C2—O1	−174.38 (12)	C9—N1—C2—C1	178.99 (11)
C8—C1—C2—N1	4.25 (12)	C20—N2—C14—C19	179.65 (11)
C8—C3—C4—C5	−1.68 (19)	C20—N2—C14—C15	0.10 (19)
C8—C7—C6—C5	−0.5 (2)	C20—N2—C13—O2	3.22 (19)
C19—C12—C13—O2	175.91 (13)	C20—N2—C13—C12	−177.87 (11)
C19—C12—C13—N2	−2.91 (12)	C18—C19—C14—N2	178.38 (10)
C19—C14—C15—C16	0.87 (18)	C18—C19—C14—C15	−2.06 (17)

1-Propyl-3-(1-propyl-1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-2H-indol-2-one (Form_III)

Crystal data

C22H22N2O2	F(000) = 736
Mr = 346.41	Dx = 1.304 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 15.0486 (2) Å	Cell parameters from 6130 reflections
b = 9.1347 (1) Å	θ = 4.8–74.8°
c = 18.5227 (2) Å	µ = 0.67 mm^−1
β = 136.112 (1)°	T = 223 K
V = 1765.16 (4) Å^3	Block, dull light red
Z = 4	0.20 × 0.17 × 0.13 mm

Data collection

XtaLAB AFC12 (RINC) Kappa dual home/near diffractometer	3541 independent reflections
Radiation source: micro-focus sealed X-ray tube, Rigaku (Cu) X-ray Source	3072 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 5.8140 pixels mm^-1	θmax = 75.2°, θmin = 4.2°
ω scans	h = −18→18
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	k = −11→5
Tmin = 0.270, Tmax = 1.000	l = −23→23
11608 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.048	w = 1/[σ^2(Fo^2) + (0.0642P)^2 + 0.5231P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.136	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.60 e Å^−3
3541 reflections	Δρmin = −0.43 e Å^−3
266 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0030 (4)
Primary atom site location: dual

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.23797 (11)	0.83302 (14)	0.20951 (9)	0.0484 (3)
N2	0.44626 (12)	0.89716 (14)	0.35540 (10)	0.0393 (3)
O1	0.33942 (14)	0.65392 (19)	0.53117 (10)	0.0677 (4)
C8	0.14714 (14)	0.57916 (16)	0.26462 (12)	0.0368 (3)
C12	0.35609 (14)	0.73178 (16)	0.38287 (11)	0.0351 (3)
N1	0.16264 (16)	0.5227 (2)	0.39373 (12)	0.0625 (5)
C13	0.33529 (14)	0.82124 (17)	0.30243 (12)	0.0367 (3)
C7	0.09157 (15)	0.56846 (19)	0.16416 (12)	0.0424 (4)
H7	0.125079	0.621893	0.144730	0.051*
C14	0.53824 (14)	0.86304 (17)	0.46145 (12)	0.0378 (3)
C19	0.48756 (14)	0.76297 (17)	0.48174 (11)	0.0364 (3)
C1	0.26442 (14)	0.64715 (17)	0.36099 (11)	0.0369 (3)
C3	0.09339 (16)	0.4978 (2)	0.28983 (13)	0.0469 (4)
C18	0.56864 (16)	0.70665 (19)	0.58220 (12)	0.0446 (4)
H18	0.538450	0.635999	0.597272	0.053*
C20	0.46824 (16)	0.99641 (18)	0.30784 (13)	0.0437 (4)
H20a	0.509764	1.085523	0.350064	0.052*
H20b	0.385449	1.024448	0.238538	0.052*
C15	0.66253 (16)	0.91414 (19)	0.53859 (13)	0.0463 (4)
H15	0.693892	0.983553	0.523914	0.056*
C17	0.69373 (17)	0.7556 (2)	0.65941 (13)	0.0509 (4)
H17	0.748607	0.717774	0.727208	0.061*
C21	0.55149 (18)	0.92896 (19)	0.29769 (14)	0.0470 (4)
H21a	0.627135	0.883807	0.364082	0.056*
H21b	0.503011	0.851881	0.244634	0.056*
C6	−0.01393 (16)	0.4781 (2)	0.09277 (14)	0.0492 (4)
H6	−0.051994	0.471295	0.024608	0.059*
C2	0.26739 (17)	0.6085 (2)	0.44193 (13)	0.0502 (4)
C5	−0.06388 (17)	0.3982 (2)	0.11984 (15)	0.0511 (4)
H5	−0.134876	0.337005	0.070232	0.061*
C16	0.73933 (16)	0.8598 (2)	0.63815 (14)	0.0518 (4)
H16	0.823886	0.894024	0.692341	0.062*
C4	−0.01076 (18)	0.4070 (2)	0.21950 (15)	0.0550 (5)
H4	−0.044649	0.352837	0.238359	0.066*
C22	0.5941 (2)	1.0418 (2)	0.26803 (16)	0.0547 (5)
H22a	0.519561	1.082888	0.200501	0.082*
H22b	0.649266	0.995890	0.264799	0.082*
H22c	0.640785	1.119231	0.319753	0.082*
C11A	0.1301 (6)	0.3169 (6)	0.5520 (5)	0.0550 (12)	0.7275
H11Aa	0.038093	0.301503	0.499288	0.082*	0.7275
H11Ab	0.151957	0.399504	0.595360	0.082*	0.7275
H11Ac	0.173286	0.229872	0.594796	0.082*	0.7275
C9A	0.1175 (2)	0.4927 (3)	0.4413 (2)	0.0439 (5)	0.7275
H9Aa	0.023635	0.488604	0.386875	0.053*	0.7275
H9Ab	0.144626	0.572028	0.489367	0.053*	0.7275
C10A	0.1717 (2)	0.3479 (3)	0.5002 (2)	0.0457 (5)	0.7275
H10Aa	0.142531	0.268421	0.451592	0.055*	0.7275
H10Ab	0.265477	0.351115	0.553044	0.055*	0.7275
C9B	0.1753 (8)	0.3899 (10)	0.4603 (7)	0.0623 (18)	0.2725
H9Ba	0.139070	0.297641	0.421392	0.075*	0.2725
H9Bb	0.263954	0.374566	0.528039	0.075*	0.2725
C11B	0.0968 (17)	0.3611 (17)	0.5390 (14)	0.063 (4)	0.2725
H11Ba	0.112163	0.259522	0.535379	0.094*	0.2725
H11Bb	0.014179	0.369729	0.514252	0.094*	0.2725
H11Bc	0.163616	0.394731	0.610530	0.094*	0.2725
C10B	0.0975 (10)	0.4561 (11)	0.4698 (8)	0.074 (2)	0.2725
H10Ba	0.009619	0.467213	0.400451	0.089*	0.2725
H10Bb	0.130901	0.553734	0.500562	0.089*	0.2725

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0432 (6)	0.0516 (7)	0.0412 (6)	0.0008 (5)	0.0273 (5)	0.0099 (5)
N2	0.0395 (7)	0.0402 (7)	0.0426 (7)	0.0012 (5)	0.0311 (6)	0.0057 (5)
O1	0.0655 (8)	0.0988 (11)	0.0477 (7)	−0.0218 (8)	0.0438 (7)	−0.0090 (7)
C8	0.0367 (7)	0.0354 (7)	0.0430 (8)	0.0036 (6)	0.0303 (7)	0.0036 (6)
C12	0.0379 (7)	0.0344 (7)	0.0384 (7)	0.0061 (6)	0.0293 (7)	0.0045 (6)
N1	0.0636 (10)	0.0812 (12)	0.0517 (9)	−0.0219 (9)	0.0445 (8)	−0.0012 (8)
C13	0.0373 (7)	0.0363 (7)	0.0409 (8)	0.0037 (6)	0.0296 (7)	0.0048 (6)
C7	0.0409 (8)	0.0456 (9)	0.0443 (8)	0.0008 (7)	0.0319 (7)	0.0007 (7)
C14	0.0388 (8)	0.0364 (8)	0.0416 (8)	0.0039 (6)	0.0301 (7)	0.0009 (6)
C19	0.0381 (7)	0.0349 (7)	0.0397 (8)	0.0040 (6)	0.0292 (7)	0.0017 (6)
C1	0.0402 (8)	0.0360 (8)	0.0400 (8)	0.0042 (6)	0.0307 (7)	0.0044 (6)
C3	0.0471 (9)	0.0492 (9)	0.0495 (9)	−0.0037 (7)	0.0366 (8)	0.0020 (7)
C18	0.0470 (9)	0.0446 (9)	0.0425 (8)	0.0063 (7)	0.0324 (8)	0.0058 (7)
C20	0.0473 (9)	0.0399 (8)	0.0518 (9)	0.0013 (7)	0.0383 (8)	0.0079 (7)
C15	0.0416 (8)	0.0463 (9)	0.0512 (9)	−0.0034 (7)	0.0336 (8)	−0.0032 (7)
C17	0.0457 (9)	0.0560 (10)	0.0392 (8)	0.0091 (8)	0.0267 (8)	0.0036 (7)
C21	0.0589 (10)	0.0384 (8)	0.0584 (10)	−0.0009 (7)	0.0471 (9)	0.0009 (7)
C6	0.0438 (9)	0.0552 (10)	0.0470 (9)	−0.0029 (8)	0.0322 (8)	−0.0070 (8)
C2	0.0505 (9)	0.0609 (11)	0.0447 (9)	−0.0073 (8)	0.0361 (8)	0.0019 (8)
C5	0.0425 (9)	0.0467 (9)	0.0581 (10)	−0.0046 (7)	0.0343 (8)	−0.0070 (8)
C16	0.0378 (8)	0.0585 (11)	0.0467 (9)	−0.0019 (8)	0.0263 (8)	−0.0076 (8)
C4	0.0529 (10)	0.0533 (10)	0.0633 (11)	−0.0095 (8)	0.0433 (10)	0.0015 (8)
C22	0.0659 (11)	0.0499 (10)	0.0714 (12)	−0.0060 (9)	0.0572 (11)	−0.0021 (9)
C11A	0.068 (3)	0.054 (3)	0.0531 (18)	−0.0091 (18)	0.047 (2)	0.0009 (18)
C9A	0.0483 (12)	0.0481 (14)	0.0536 (13)	0.0058 (11)	0.0428 (12)	0.0124 (11)
C10A	0.0528 (13)	0.0421 (13)	0.0495 (13)	−0.0008 (10)	0.0393 (12)	0.0083 (10)
C9B	0.058 (4)	0.060 (5)	0.064 (5)	0.000 (4)	0.042 (4)	0.008 (4)
C11B	0.090 (10)	0.067 (10)	0.078 (8)	−0.012 (6)	0.076 (9)	−0.004 (7)
C10B	0.087 (6)	0.071 (6)	0.082 (6)	0.011 (5)	0.067 (5)	0.010 (5)

Geometric parameters (Å, º)

O2—C13	1.2188 (18)	C21—H21a	0.9800
N2—C13	1.368 (2)	C21—H21b	0.9800
N2—C14	1.3973 (19)	C21—C22	1.511 (2)
N2—C20	1.4586 (19)	C6—H6	0.9400
O1—C2	1.223 (2)	C6—C5	1.375 (3)
C8—C7	1.389 (2)	C5—H5	0.9400
C8—C1	1.465 (2)	C5—C4	1.388 (3)
C8—C3	1.403 (2)	C16—H16	0.9400
C12—C13	1.521 (2)	C4—H4	0.9400
C12—C19	1.458 (2)	C22—H22a	0.9700
C12—C1	1.364 (2)	C22—H22b	0.9700
N1—C3	1.397 (2)	C22—H22c	0.9700
N1—C2	1.366 (2)	C11A—H11Aa	0.9700
N1—C9A	1.476 (3)	C11A—H11Ab	0.9700
N1—C9B	1.641 (9)	C11A—H11Ac	0.9700
C7—H7	0.9400	C11A—C10A	1.503 (7)
C7—C6	1.387 (2)	C9A—H9Aa	0.9800
C14—C19	1.404 (2)	C9A—H9Ab	0.9800
C14—C15	1.381 (2)	C9A—C10A	1.524 (3)
C19—C18	1.394 (2)	C10A—H10Aa	0.9800
C1—C2	1.509 (2)	C10A—H10Ab	0.9800
C3—C4	1.378 (2)	C9B—H9Ba	0.9800
C18—H18	0.9400	C9B—H9Bb	0.9800
C18—C17	1.381 (2)	C9B—C10B	1.436 (12)
C20—H20a	0.9800	C11B—H11Ba	0.9700
C20—H20b	0.9800	C11B—H11Bb	0.9700
C20—C21	1.525 (2)	C11B—H11Bc	0.9700
C15—H15	0.9400	C11B—C10B	1.555 (19)
C15—C16	1.382 (2)	C10B—H10Ba	0.9800
C17—H17	0.9400	C10B—H10Bb	0.9800
C17—C16	1.386 (3)
C13—N2—C14	110.83 (12)	C5—C6—H6	119.4
C13—N2—C20	124.96 (13)	O1—C2—N1	123.97 (16)
C14—N2—C20	124.17 (13)	O1—C2—C1	128.76 (16)
C7—C8—C1	134.09 (14)	N1—C2—C1	106.90 (14)
C7—C8—C3	118.27 (15)	C6—C5—H5	119.6
C3—C8—C1	107.24 (13)	C6—C5—C4	120.81 (16)
C19—C12—C13	105.09 (13)	C4—C5—H5	119.6
C1—C12—C13	124.30 (13)	C15—C16—C17	121.10 (16)
C1—C12—C19	130.57 (14)	C15—C16—H16	119.4
C3—N1—C9A	125.81 (17)	C17—C16—H16	119.4
C3—N1—C9B	118.8 (3)	C3—C4—C5	117.68 (17)
C2—N1—C3	110.97 (14)	C3—C4—H4	121.2
C2—N1—C9A	121.83 (17)	C5—C4—H4	121.2
C2—N1—C9B	118.6 (3)	C21—C22—H22a	109.5
O2—C13—N2	124.85 (14)	C21—C22—H22b	109.5
O2—C13—C12	128.34 (14)	C21—C22—H22c	109.5
N2—C13—C12	106.67 (12)	H22a—C22—H22b	109.5
C8—C7—H7	120.4	H22a—C22—H22c	109.5
C6—C7—C8	119.30 (15)	H22b—C22—H22c	109.5
C6—C7—H7	120.4	H11Aa—C11A—H11Ab	109.5
N2—C14—C19	110.04 (13)	H11Aa—C11A—H11Ac	109.5
C15—C14—N2	127.60 (15)	H11Ab—C11A—H11Ac	109.5
C15—C14—C19	122.36 (15)	C10A—C11A—H11Aa	109.5
C14—C19—C12	107.34 (13)	C10A—C11A—H11Ab	109.5
C18—C19—C12	133.97 (15)	C10A—C11A—H11Ac	109.5
C18—C19—C14	118.42 (14)	N1—C9A—H9Aa	109.6
C8—C1—C2	104.98 (13)	N1—C9A—H9Ab	109.6
C12—C1—C8	132.45 (14)	N1—C9A—C10A	110.5 (2)
C12—C1—C2	122.55 (14)	H9Aa—C9A—H9Ab	108.1
N1—C3—C8	109.58 (15)	C10A—C9A—H9Aa	109.6
C4—C3—C8	122.68 (16)	C10A—C9A—H9Ab	109.6
C4—C3—N1	127.72 (16)	C11A—C10A—C9A	111.5 (3)
C19—C18—H18	120.3	C11A—C10A—H10Aa	109.3
C17—C18—C19	119.41 (16)	C11A—C10A—H10Ab	109.3
C17—C18—H18	120.3	C9A—C10A—H10Aa	109.3
N2—C20—H20a	109.0	C9A—C10A—H10Ab	109.3
N2—C20—H20b	109.0	H10Aa—C10A—H10Ab	108.0
N2—C20—C21	112.80 (13)	N1—C9B—H9Ba	112.4
H20a—C20—H20b	107.8	N1—C9B—H9Bb	112.4
C21—C20—H20a	109.0	H9Ba—C9B—H9Bb	110.0
C21—C20—H20b	109.0	C10B—C9B—N1	96.7 (7)
C14—C15—H15	121.1	C10B—C9B—H9Ba	112.4
C14—C15—C16	117.76 (16)	C10B—C9B—H9Bb	112.4
C16—C15—H15	121.1	H11Ba—C11B—H11Bb	109.5
C18—C17—H17	119.6	H11Ba—C11B—H11Bc	109.5
C18—C17—C16	120.83 (16)	H11Bb—C11B—H11Bc	109.5
C16—C17—H17	119.6	C10B—C11B—H11Ba	109.5
C20—C21—H21a	109.3	C10B—C11B—H11Bb	109.5
C20—C21—H21b	109.3	C10B—C11B—H11Bc	109.5
H21a—C21—H21b	107.9	C9B—C10B—C11B	110.9 (9)
C22—C21—C20	111.76 (14)	C9B—C10B—H10Ba	109.5
C22—C21—H21a	109.3	C9B—C10B—H10Bb	109.5
C22—C21—H21b	109.3	C11B—C10B—H10Ba	109.5
C7—C6—H6	119.4	C11B—C10B—H10Bb	109.5
C5—C6—C7	121.25 (16)	H10Ba—C10B—H10Bb	108.1
N2—C14—C19—C12	0.10 (17)	C19—C18—C17—C16	0.0 (3)
N2—C14—C19—C18	174.91 (13)	C1—C8—C7—C6	171.43 (16)
N2—C14—C15—C16	−176.81 (16)	C1—C8—C3—N1	6.02 (19)
N2—C20—C21—C22	−168.95 (15)	C1—C8—C3—C4	−172.98 (17)
C8—C7—C6—C5	−0.4 (3)	C1—C12—C13—O2	0.5 (3)
C8—C1—C2—O1	−171.2 (2)	C1—C12—C13—N2	176.38 (14)
C8—C1—C2—N1	1.87 (19)	C1—C12—C19—C14	−176.90 (15)
C8—C3—C4—C5	−0.6 (3)	C1—C12—C19—C18	9.4 (3)
C12—C19—C18—C17	176.12 (17)	C3—C8—C7—C6	−0.3 (2)
C12—C1—C2—O1	7.2 (3)	C3—C8—C1—C12	176.99 (16)
C12—C1—C2—N1	−179.66 (16)	C3—C8—C1—C2	−4.75 (17)
N1—C3—C4—C5	−179.38 (19)	C3—N1—C2—O1	175.3 (2)
N1—C9A—C10A—C11A	178.3 (3)	C3—N1—C2—C1	1.8 (2)
N1—C9B—C10B—C11B	−175.5 (10)	C3—N1—C9A—C10A	99.3 (3)
C13—N2—C14—C19	−1.20 (18)	C3—N1—C9B—C10B	−111.3 (6)
C13—N2—C14—C15	177.82 (15)	C18—C17—C16—C15	−2.2 (3)
C13—N2—C20—C21	−103.14 (18)	C20—N2—C13—O2	−4.4 (2)
C13—C12—C19—C14	0.89 (16)	C20—N2—C13—C12	179.61 (14)
C13—C12—C19—C18	−172.76 (17)	C20—N2—C14—C19	−179.12 (14)
C13—C12—C1—C8	22.6 (3)	C20—N2—C14—C15	−0.1 (3)
C13—C12—C1—C2	−155.44 (15)	C15—C14—C19—C12	−178.97 (14)
C7—C8—C1—C12	4.7 (3)	C15—C14—C19—C18	−4.2 (2)
C7—C8—C1—C2	−177.09 (18)	C6—C5—C4—C3	−0.2 (3)
C7—C8—C3—N1	179.79 (16)	C2—N1—C3—C8	−5.0 (2)
C7—C8—C3—C4	0.8 (3)	C2—N1—C3—C4	174.0 (2)
C7—C6—C5—C4	0.7 (3)	C2—N1—C9A—C10A	−95.4 (3)
C14—N2—C13—O2	177.74 (15)	C2—N1—C9B—C10B	108.8 (6)
C14—N2—C13—C12	1.71 (16)	C9A—N1—C3—C8	161.66 (19)
C14—N2—C20—C21	74.5 (2)	C9A—N1—C3—C4	−19.4 (3)
C14—C19—C18—C17	3.0 (2)	C9A—N1—C2—O1	8.0 (3)
C14—C15—C16—C17	1.1 (3)	C9A—N1—C2—C1	−165.48 (18)
C19—C12—C13—O2	−177.43 (16)	C9B—N1—C3—C8	−147.7 (4)
C19—C12—C13—N2	−1.59 (15)	C9B—N1—C3—C4	31.2 (4)
C19—C12—C1—C8	−160.02 (16)	C9B—N1—C2—O1	−41.9 (5)
C19—C12—C1—C2	22.0 (3)	C9B—N1—C2—C1	144.6 (4)
C19—C14—C15—C16	2.1 (2)