(R*)-1-Benzyl-3-(2-hy­droxy­phen­yl)indoline-2-one

The title compound, C₂₁H₁₇NO₂, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The indoline ring system is almost planar in both mol­ecules (r.m.s. deviations = 0.020 and 0.024 Å for mol­ecules A and B, respectively). The benzyl and phenol rings are inclined to the indole ring system by 80.39 (12) and 68.39 (12)° in mol­ecule A, and by 79.90 (13) and 74.88 (10)° in mol­ecule B. The aryl rings are inclined to one another by 33.30 (14) and 30.62 (14)° in mol­ecules A and B, respectively. In the crystal, A mol­ecules are linked by pairs of O—H...O hydrogen bonds, forming inversion dimers. The same situation is observed for the B mol­ecules and both sets of inversion dimers enclose R₂²(14) ring motifs. These dimers stack along the a-axis direction and are linked by offset π–π inter­actions [inter­centroid distance = 3.6802 (13) Å] involving A and B indole ring systems, forming layers parallel to the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.197
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C31 Check
PLAT331_ALERT_2_C Small Average Phenyl   C-C Dist. C31    -C36           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00414 Ang.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -6.426 Report
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.177 Report
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595         16 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.12 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT793_ALERT_4_G The Model has Chirality at C7      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C28     (Centro SPGR)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           3 Note

   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
   7 ALERT level G = General information/check it is not something unexpected

   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek,2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(R*)-1-Benzyl-3-(2-hydroxyphenyl)indoline-2-one

Crystal data

C21H17NO2	Z = 4
Mr = 315.36	F(000) = 664
Triclinic, P1	Dx = 1.278 Mg m^−3
a = 11.1344 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.0889 (5) Å	Cell parameters from 8113 reflections
c = 12.4679 (6) Å	θ = 2.4–25.7°
α = 89.171 (3)°	µ = 0.08 mm^−1
β = 79.125 (3)°	T = 296 K
γ = 84.202 (3)°	Block, colourless
V = 1639.62 (14) Å^3	0.35 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	3525 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.035
ω and φ scan	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→13
Tmin = 0.972, Tmax = 0.984	k = −14→14
26691 measured reflections	l = −14→14
5763 independent reflections

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.197	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1204P)^2 + 0.1554P] where P = (Fo^2 + 2Fc^2)/3
5763 reflections	(Δ/σ)max < 0.001
433 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.20 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.

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

	x	y	z	Uiso*/Ueq
O4	0.46387 (17)	0.61250 (15)	0.44690 (15)	0.0685 (5)
H4	0.492150	0.577156	0.390610	0.103*
N2	0.38028 (18)	0.69335 (16)	0.82332 (15)	0.0503 (5)
O3	0.43219 (19)	0.54674 (15)	0.70547 (15)	0.0718 (6)
C26	0.3491 (2)	0.80907 (19)	0.8179 (2)	0.0484 (6)
C37	0.5165 (2)	0.74505 (18)	0.56209 (18)	0.0456 (6)
C28	0.3937 (2)	0.73869 (19)	0.63812 (19)	0.0494 (6)
H28	0.330556	0.724990	0.596145	0.059*
C27	0.3521 (2)	0.8390 (2)	0.7102 (2)	0.0501 (6)
C42	0.5483 (2)	0.67851 (19)	0.46908 (19)	0.0489 (6)
C29	0.4045 (2)	0.6465 (2)	0.7224 (2)	0.0522 (6)
C31	0.4977 (2)	0.65051 (19)	0.97035 (19)	0.0486 (6)
C41	0.6625 (3)	0.6816 (2)	0.4024 (2)	0.0590 (7)
H41	0.684161	0.636726	0.340486	0.071*
C5	0.0533 (2)	0.7082 (2)	0.8208 (3)	0.0636 (7)
O1	0.0392 (2)	0.80217 (16)	0.5609 (2)	0.0898 (7)
O2	−0.00597 (18)	1.06347 (16)	0.61019 (19)	0.0867 (7)
H2	−0.016343	1.115971	0.569435	0.130*
C30	0.3871 (2)	0.6317 (2)	0.9235 (2)	0.0550 (6)
H30A	0.388706	0.552929	0.908650	0.066*
H30B	0.313738	0.653266	0.977235	0.066*
C10	−0.0150 (2)	0.5262 (2)	0.6615 (2)	0.0570 (7)
C16	−0.1160 (2)	0.9517 (2)	0.7407 (2)	0.0609 (7)
N1	0.0688 (2)	0.69565 (18)	0.7074 (2)	0.0666 (6)
C25	0.3207 (2)	0.8848 (2)	0.9022 (2)	0.0591 (7)
H25	0.319239	0.862822	0.974243	0.071*
C21	−0.1169 (3)	1.0392 (2)	0.6678 (2)	0.0667 (8)
C38	0.6004 (2)	0.8135 (2)	0.5845 (2)	0.0580 (7)
H38	0.579726	0.858638	0.646359	0.070*
C8	0.0386 (2)	0.7933 (2)	0.6585 (3)	0.0689 (8)
C40	0.7439 (3)	0.7510 (2)	0.4276 (2)	0.0677 (8)
H40	0.820268	0.752820	0.382363	0.081*
C7	0.0038 (2)	0.8830 (2)	0.7478 (2)	0.0648 (7)
H7	0.068746	0.933263	0.737248	0.078*
C22	0.3256 (2)	0.9492 (2)	0.6852 (2)	0.0632 (7)
H22	0.327328	0.971179	0.613131	0.076*
C24	0.2945 (3)	0.9949 (2)	0.8759 (3)	0.0694 (8)
H24	0.275422	1.048307	0.931109	0.083*
C11	−0.0165 (3)	0.4223 (2)	0.7062 (2)	0.0683 (8)
H11	0.051960	0.390760	0.732365	0.082*
C17	−0.2264 (3)	0.9277 (2)	0.8038 (2)	0.0690 (8)
H17	−0.227202	0.869856	0.853875	0.083*
C6	0.0122 (2)	0.8185 (2)	0.8486 (3)	0.0643 (7)
C39	0.7136 (3)	0.8171 (2)	0.5184 (2)	0.0672 (8)
H39	0.768729	0.864014	0.535308	0.081*
C13	−0.2193 (3)	0.4095 (3)	0.6766 (2)	0.0700 (8)
H13	−0.287695	0.370238	0.681014	0.084*
C18	−0.3357 (3)	0.9886 (3)	0.7934 (3)	0.0802 (9)
H18	−0.409399	0.972573	0.836734	0.096*
C1	−0.0093 (3)	0.8493 (3)	0.9580 (3)	0.0779 (9)
H1	−0.038062	0.922200	0.978999	0.093*
C36	0.4861 (3)	0.6869 (2)	1.0755 (2)	0.0718 (8)
H36	0.408038	0.702398	1.117624	0.086*
C2	0.0125 (3)	0.7706 (3)	1.0350 (3)	0.0879 (10)
H2A	−0.001137	0.790974	1.108236	0.106*
C20	−0.2257 (3)	1.0979 (2)	0.6558 (3)	0.0780 (9)
H20	−0.225973	1.154959	0.605021	0.094*
C23	0.2962 (3)	1.0267 (2)	0.7696 (3)	0.0726 (8)
H23	0.277373	1.101192	0.753898	0.087*
C4	0.0742 (3)	0.6298 (3)	0.8971 (3)	0.0727 (8)
H4A	0.101207	0.556516	0.876558	0.087*
C9	0.0963 (3)	0.5902 (2)	0.6491 (3)	0.0709 (8)
H9A	0.161286	0.545878	0.676735	0.085*
H9B	0.125575	0.603928	0.572233	0.085*
C3	0.0542 (3)	0.6621 (3)	1.0051 (3)	0.0835 (9)
H3	0.068983	0.610288	1.058122	0.100*
C19	−0.3343 (3)	1.0721 (3)	0.7191 (3)	0.0841 (10)
H19	−0.407784	1.112389	0.710997	0.101*
C32	0.6145 (3)	0.6286 (3)	0.9098 (3)	0.0751 (8)
H32	0.625252	0.603469	0.838144	0.090*
C15	−0.1186 (3)	0.5711 (2)	0.6259 (2)	0.0710 (8)
H15	−0.120036	0.642028	0.595998	0.085*
C12	−0.1174 (3)	0.3632 (2)	0.7134 (3)	0.0777 (9)
H12	−0.116115	0.292220	0.743091	0.093*
C14	−0.2197 (3)	0.5139 (3)	0.6335 (2)	0.0761 (8)
H14	−0.289045	0.546281	0.609107	0.091*
C35	0.5864 (4)	0.7011 (3)	1.1198 (3)	0.0973 (12)
H35	0.575943	0.725624	1.191677	0.117*
C33	0.7156 (3)	0.6440 (3)	0.9551 (4)	0.0982 (12)
H33	0.794259	0.629754	0.913735	0.118*
C34	0.7003 (4)	0.6798 (3)	1.0604 (5)	0.1030 (14)
H34	0.768506	0.689614	1.091063	0.124*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0774 (13)	0.0655 (12)	0.0685 (12)	−0.0134 (10)	−0.0242 (10)	−0.0221 (9)
N2	0.0550 (12)	0.0461 (12)	0.0513 (12)	−0.0111 (9)	−0.0102 (10)	−0.0048 (9)
O3	0.1073 (16)	0.0436 (11)	0.0650 (12)	−0.0164 (10)	−0.0124 (10)	−0.0084 (8)
C26	0.0399 (13)	0.0483 (14)	0.0569 (15)	−0.0079 (10)	−0.0066 (11)	−0.0065 (11)
C37	0.0500 (14)	0.0419 (13)	0.0478 (13)	−0.0053 (10)	−0.0160 (11)	−0.0022 (10)
C28	0.0519 (14)	0.0496 (14)	0.0507 (14)	−0.0110 (11)	−0.0163 (11)	−0.0057 (11)
C27	0.0426 (13)	0.0500 (14)	0.0578 (15)	−0.0070 (10)	−0.0085 (11)	−0.0049 (11)
C42	0.0603 (16)	0.0421 (13)	0.0485 (14)	−0.0038 (11)	−0.0213 (12)	−0.0005 (11)
C29	0.0508 (15)	0.0493 (16)	0.0590 (15)	−0.0145 (11)	−0.0112 (12)	−0.0076 (12)
C31	0.0512 (15)	0.0418 (13)	0.0524 (14)	−0.0096 (10)	−0.0069 (12)	0.0047 (11)
C41	0.0724 (19)	0.0532 (15)	0.0485 (14)	0.0038 (13)	−0.0090 (13)	−0.0042 (11)
C5	0.0380 (14)	0.0608 (18)	0.092 (2)	−0.0133 (12)	−0.0069 (14)	−0.0085 (16)
O1	0.1099 (18)	0.0655 (13)	0.0787 (15)	−0.0053 (12)	0.0197 (13)	−0.0025 (11)
O2	0.0701 (14)	0.0613 (12)	0.1211 (18)	−0.0184 (10)	0.0067 (12)	0.0114 (12)
C30	0.0575 (15)	0.0558 (15)	0.0528 (14)	−0.0174 (12)	−0.0069 (12)	0.0029 (12)
C10	0.0591 (17)	0.0497 (15)	0.0562 (15)	0.0016 (12)	0.0018 (12)	−0.0111 (12)
C16	0.0520 (16)	0.0478 (15)	0.0802 (18)	−0.0153 (12)	0.0007 (13)	−0.0177 (13)
N1	0.0558 (14)	0.0536 (14)	0.0845 (17)	−0.0089 (10)	0.0041 (12)	−0.0108 (12)
C25	0.0572 (16)	0.0581 (16)	0.0578 (15)	−0.0057 (12)	0.0004 (12)	−0.0115 (12)
C21	0.0587 (18)	0.0454 (15)	0.092 (2)	−0.0123 (13)	0.0007 (15)	−0.0161 (14)
C38	0.0582 (16)	0.0567 (15)	0.0610 (16)	−0.0092 (12)	−0.0134 (13)	−0.0141 (12)
C8	0.0509 (17)	0.0581 (18)	0.088 (2)	−0.0095 (13)	0.0134 (15)	−0.0064 (16)
C40	0.0599 (17)	0.0609 (17)	0.0768 (19)	−0.0066 (14)	0.0011 (14)	0.0045 (15)
C7	0.0474 (15)	0.0502 (15)	0.093 (2)	−0.0155 (12)	0.0027 (14)	−0.0117 (15)
C22	0.0614 (17)	0.0571 (17)	0.0697 (17)	−0.0020 (13)	−0.0109 (14)	0.0022 (14)
C24	0.0649 (18)	0.0572 (17)	0.079 (2)	0.0022 (13)	0.0011 (15)	−0.0188 (15)
C11	0.0670 (18)	0.0516 (16)	0.088 (2)	0.0033 (13)	−0.0225 (16)	−0.0061 (14)
C17	0.0569 (18)	0.0725 (19)	0.0762 (19)	−0.0184 (15)	−0.0010 (15)	−0.0185 (15)
C6	0.0453 (15)	0.0583 (17)	0.088 (2)	−0.0143 (12)	−0.0031 (14)	−0.0142 (15)
C39	0.0580 (17)	0.0588 (17)	0.086 (2)	−0.0161 (13)	−0.0110 (15)	−0.0076 (15)
C13	0.073 (2)	0.075 (2)	0.0657 (17)	−0.0189 (16)	−0.0169 (15)	−0.0033 (15)
C18	0.0542 (19)	0.091 (2)	0.092 (2)	−0.0155 (17)	0.0013 (16)	−0.031 (2)
C1	0.0603 (19)	0.071 (2)	0.103 (3)	−0.0149 (15)	−0.0110 (17)	−0.0228 (19)
C36	0.073 (2)	0.079 (2)	0.0649 (18)	0.0019 (15)	−0.0204 (15)	−0.0119 (15)
C2	0.074 (2)	0.106 (3)	0.089 (2)	−0.0201 (19)	−0.0206 (18)	−0.012 (2)
C20	0.077 (2)	0.0543 (17)	0.102 (2)	−0.0088 (15)	−0.0115 (18)	−0.0159 (16)
C23	0.0681 (19)	0.0467 (16)	0.097 (2)	0.0043 (13)	−0.0051 (16)	−0.0072 (16)
C4	0.0515 (17)	0.0682 (19)	0.099 (2)	−0.0089 (14)	−0.0147 (16)	−0.0056 (18)
C9	0.0577 (17)	0.0554 (16)	0.090 (2)	−0.0020 (13)	0.0099 (15)	−0.0146 (15)
C3	0.063 (2)	0.091 (3)	0.101 (3)	−0.0152 (17)	−0.0232 (18)	0.001 (2)
C19	0.061 (2)	0.080 (2)	0.111 (3)	0.0014 (16)	−0.0157 (19)	−0.033 (2)
C32	0.0594 (19)	0.088 (2)	0.0713 (19)	−0.0060 (15)	0.0015 (15)	0.0098 (16)
C15	0.081 (2)	0.0563 (16)	0.0761 (19)	−0.0048 (15)	−0.0175 (16)	0.0079 (14)
C12	0.093 (2)	0.0561 (17)	0.092 (2)	−0.0187 (16)	−0.0321 (19)	0.0075 (16)
C14	0.074 (2)	0.082 (2)	0.0760 (19)	−0.0005 (16)	−0.0275 (16)	0.0025 (16)
C35	0.118 (3)	0.083 (2)	0.106 (3)	−0.001 (2)	−0.063 (3)	−0.015 (2)
C33	0.050 (2)	0.110 (3)	0.132 (3)	−0.0178 (18)	−0.008 (2)	0.042 (3)
C34	0.095 (3)	0.076 (2)	0.160 (4)	−0.031 (2)	−0.070 (3)	0.031 (3)

Geometric parameters (Å, º)

O4—C42	1.361 (3)	C40—H40	0.9300
O4—H4	0.8200	C7—C6	1.483 (4)
N2—C29	1.355 (3)	C7—H7	0.9800
N2—C26	1.411 (3)	C22—C23	1.390 (4)
N2—C30	1.456 (3)	C22—H22	0.9300
O3—C29	1.226 (3)	C24—C23	1.371 (4)
C26—C25	1.374 (3)	C24—H24	0.9300
C26—C27	1.382 (3)	C11—C12	1.379 (4)
C37—C38	1.377 (3)	C11—H11	0.9300
C37—C42	1.390 (3)	C17—C18	1.385 (4)
C37—C28	1.518 (3)	C17—H17	0.9300
C28—C27	1.502 (3)	C6—C1	1.389 (4)
C28—C29	1.532 (3)	C39—H39	0.9300
C28—H28	0.9800	C13—C14	1.364 (4)
C27—C22	1.379 (3)	C13—C12	1.368 (4)
C42—C41	1.385 (4)	C13—H13	0.9300
C31—C36	1.367 (4)	C18—C19	1.359 (5)
C31—C32	1.377 (4)	C18—H18	0.9300
C31—C30	1.497 (3)	C1—C2	1.379 (5)
C41—C40	1.375 (4)	C1—H1	0.9300
C41—H41	0.9300	C36—C35	1.362 (5)
C5—C4	1.366 (4)	C36—H36	0.9300
C5—C6	1.392 (4)	C2—C3	1.379 (5)
C5—N1	1.401 (4)	C2—H2A	0.9300
O1—C8	1.220 (4)	C20—C19	1.375 (4)
O2—C21	1.364 (3)	C20—H20	0.9300
O2—H2	0.8200	C23—H23	0.9300
C30—H30A	0.9700	C4—C3	1.378 (5)
C30—H30B	0.9700	C4—H4A	0.9300
C10—C11	1.367 (4)	C9—H9A	0.9700
C10—C15	1.372 (4)	C9—H9B	0.9700
C10—C9	1.508 (4)	C3—H3	0.9300
C16—C17	1.384 (4)	C19—H19	0.9300
C16—C21	1.386 (4)	C32—C33	1.381 (5)
C16—C7	1.514 (4)	C32—H32	0.9300
N1—C8	1.362 (4)	C15—C14	1.368 (4)
N1—C9	1.452 (4)	C15—H15	0.9300
C25—C24	1.382 (4)	C12—H12	0.9300
C25—H25	0.9300	C14—H14	0.9300
C21—C20	1.373 (4)	C35—C34	1.346 (6)
C38—C39	1.374 (4)	C35—H35	0.9300
C38—H38	0.9300	C33—C34	1.363 (6)
C8—C7	1.533 (4)	C33—H33	0.9300
C40—C39	1.365 (4)	C34—H34	0.9300
C42—O4—H4	109.5	C23—C22—H22	120.6
C29—N2—C26	111.12 (19)	C23—C24—C25	121.0 (3)
C29—N2—C30	124.0 (2)	C23—C24—H24	119.5
C26—N2—C30	124.8 (2)	C25—C24—H24	119.5
C25—C26—C27	122.7 (2)	C10—C11—C12	121.5 (3)
C25—C26—N2	128.2 (2)	C10—C11—H11	119.3
C27—C26—N2	109.1 (2)	C12—C11—H11	119.3
C38—C37—C42	118.4 (2)	C18—C17—C16	120.9 (3)
C38—C37—C28	121.5 (2)	C18—C17—H17	119.6
C42—C37—C28	120.2 (2)	C16—C17—H17	119.6
C27—C28—C37	114.06 (18)	C1—C6—C5	118.6 (3)
C27—C28—C29	101.62 (19)	C1—C6—C7	132.1 (3)
C37—C28—C29	110.23 (19)	C5—C6—C7	109.3 (3)
C27—C28—H28	110.2	C40—C39—C38	119.0 (2)
C37—C28—H28	110.2	C40—C39—H39	120.5
C29—C28—H28	110.2	C38—C39—H39	120.5
C22—C27—C26	119.3 (2)	C14—C13—C12	119.4 (3)
C22—C27—C28	131.1 (2)	C14—C13—H13	120.3
C26—C27—C28	109.5 (2)	C12—C13—H13	120.3
O4—C42—C41	122.4 (2)	C19—C18—C17	119.4 (3)
O4—C42—C37	117.8 (2)	C19—C18—H18	120.3
C41—C42—C37	119.8 (2)	C17—C18—H18	120.3
O3—C29—N2	123.7 (2)	C2—C1—C6	119.1 (3)
O3—C29—C28	127.8 (2)	C2—C1—H1	120.4
N2—C29—C28	108.5 (2)	C6—C1—H1	120.4
C36—C31—C32	117.9 (3)	C35—C36—C31	121.5 (3)
C36—C31—C30	121.1 (2)	C35—C36—H36	119.2
C32—C31—C30	120.9 (2)	C31—C36—H36	119.2
C40—C41—C42	120.2 (3)	C3—C2—C1	121.1 (3)
C40—C41—H41	119.9	C3—C2—H2A	119.5
C42—C41—H41	119.9	C1—C2—H2A	119.5
C4—C5—C6	122.4 (3)	C21—C20—C19	119.9 (3)
C4—C5—N1	128.6 (3)	C21—C20—H20	120.1
C6—C5—N1	109.0 (3)	C19—C20—H20	120.1
C21—O2—H2	109.5	C24—C23—C22	120.9 (3)
N2—C30—C31	113.23 (18)	C24—C23—H23	119.5
N2—C30—H30A	108.9	C22—C23—H23	119.5
C31—C30—H30A	108.9	C5—C4—C3	118.4 (3)
N2—C30—H30B	108.9	C5—C4—H4A	120.8
C31—C30—H30B	108.9	C3—C4—H4A	120.8
H30A—C30—H30B	107.7	N1—C9—C10	111.9 (2)
C11—C10—C15	117.7 (3)	N1—C9—H9A	109.2
C11—C10—C9	122.2 (3)	C10—C9—H9A	109.2
C15—C10—C9	120.1 (3)	N1—C9—H9B	109.2
C17—C16—C21	118.5 (3)	C10—C9—H9B	109.2
C17—C16—C7	121.6 (3)	H9A—C9—H9B	107.9
C21—C16—C7	119.9 (2)	C4—C3—C2	120.5 (3)
C8—N1—C5	111.4 (2)	C4—C3—H3	119.8
C8—N1—C9	122.9 (3)	C2—C3—H3	119.8
C5—N1—C9	125.1 (2)	C18—C19—C20	120.8 (3)
C26—C25—C24	117.4 (2)	C18—C19—H19	119.6
C26—C25—H25	121.3	C20—C19—H19	119.6
C24—C25—H25	121.3	C31—C32—C33	120.2 (3)
O2—C21—C20	122.5 (3)	C31—C32—H32	119.9
O2—C21—C16	117.0 (3)	C33—C32—H32	119.9
C20—C21—C16	120.5 (3)	C14—C15—C10	121.5 (3)
C39—C38—C37	122.0 (2)	C14—C15—H15	119.3
C39—C38—H38	119.0	C10—C15—H15	119.3
C37—C38—H38	119.0	C13—C12—C11	119.7 (3)
O1—C8—N1	123.5 (3)	C13—C12—H12	120.1
O1—C8—C7	128.8 (3)	C11—C12—H12	120.1
N1—C8—C7	107.6 (3)	C13—C14—C15	120.2 (3)
C39—C40—C41	120.6 (3)	C13—C14—H14	119.9
C39—C40—H40	119.7	C15—C14—H14	119.9
C41—C40—H40	119.7	C34—C35—C36	120.4 (4)
C6—C7—C16	118.5 (2)	C34—C35—H35	119.8
C6—C7—C8	102.5 (2)	C36—C35—H35	119.8
C16—C7—C8	112.2 (2)	C34—C33—C32	120.2 (3)
C6—C7—H7	107.7	C34—C33—H33	119.9
C16—C7—H7	107.7	C32—C33—H33	119.9
C8—C7—H7	107.7	C35—C34—C33	119.8 (3)
C27—C22—C23	118.7 (3)	C35—C34—H34	120.1
C27—C22—H22	120.6	C33—C34—H34	120.1
C29—N2—C26—C25	−178.9 (2)	C21—C16—C7—C8	−82.0 (3)
C30—N2—C26—C25	0.5 (4)	O1—C8—C7—C6	175.7 (3)
C29—N2—C26—C27	0.5 (3)	N1—C8—C7—C6	−3.4 (3)
C30—N2—C26—C27	179.8 (2)	O1—C8—C7—C16	47.4 (4)
C38—C37—C28—C27	22.5 (3)	N1—C8—C7—C16	−131.7 (2)
C42—C37—C28—C27	−159.4 (2)	C26—C27—C22—C23	−0.3 (4)
C38—C37—C28—C29	−91.0 (3)	C28—C27—C22—C23	−175.8 (2)
C42—C37—C28—C29	87.0 (2)	C26—C25—C24—C23	0.4 (4)
C25—C26—C27—C22	0.0 (4)	C15—C10—C11—C12	1.4 (4)
N2—C26—C27—C22	−179.4 (2)	C9—C10—C11—C12	−177.7 (3)
C25—C26—C27—C28	176.4 (2)	C21—C16—C17—C18	0.9 (4)
N2—C26—C27—C28	−3.0 (3)	C7—C16—C17—C18	−177.5 (3)
C37—C28—C27—C22	61.3 (3)	C4—C5—C6—C1	−0.6 (4)
C29—C28—C27—C22	179.9 (2)	N1—C5—C6—C1	180.0 (2)
C37—C28—C27—C26	−114.6 (2)	C4—C5—C6—C7	177.6 (2)
C29—C28—C27—C26	4.0 (2)	N1—C5—C6—C7	−1.8 (3)
C38—C37—C42—O4	−179.0 (2)	C16—C7—C6—C1	−54.8 (4)
C28—C37—C42—O4	2.9 (3)	C8—C7—C6—C1	−179.0 (3)
C38—C37—C42—C41	0.6 (3)	C16—C7—C6—C5	127.3 (2)
C28—C37—C42—C41	−177.5 (2)	C8—C7—C6—C5	3.1 (3)
C26—N2—C29—O3	−179.0 (2)	C41—C40—C39—C38	0.0 (4)
C30—N2—C29—O3	1.6 (4)	C37—C38—C39—C40	0.1 (4)
C26—N2—C29—C28	2.1 (2)	C16—C17—C18—C19	0.8 (4)
C30—N2—C29—C28	−177.21 (19)	C5—C6—C1—C2	1.0 (4)
C27—C28—C29—O3	177.6 (2)	C7—C6—C1—C2	−176.7 (3)
C37—C28—C29—O3	−61.2 (3)	C32—C31—C36—C35	−0.2 (4)
C27—C28—C29—N2	−3.7 (2)	C30—C31—C36—C35	178.0 (3)
C37—C28—C29—N2	117.6 (2)	C6—C1—C2—C3	−0.5 (5)
O4—C42—C41—C40	179.1 (2)	O2—C21—C20—C19	−177.6 (3)
C37—C42—C41—C40	−0.5 (3)	C16—C21—C20—C19	2.1 (4)
C29—N2—C30—C31	105.8 (3)	C25—C24—C23—C22	−0.7 (4)
C26—N2—C30—C31	−73.5 (3)	C27—C22—C23—C24	0.6 (4)
C36—C31—C30—N2	124.5 (3)	C6—C5—C4—C3	−0.4 (4)
C32—C31—C30—N2	−57.3 (3)	N1—C5—C4—C3	178.9 (3)
C4—C5—N1—C8	−179.9 (2)	C8—N1—C9—C10	−95.5 (3)
C6—C5—N1—C8	−0.5 (3)	C5—N1—C9—C10	75.2 (3)
C4—C5—N1—C9	8.5 (4)	C11—C10—C9—N1	−120.7 (3)
C6—C5—N1—C9	−172.2 (2)	C15—C10—C9—N1	60.2 (4)
C27—C26—C25—C24	0.0 (4)	C5—C4—C3—C2	0.9 (4)
N2—C26—C25—C24	179.2 (2)	C1—C2—C3—C4	−0.5 (5)
C17—C16—C21—O2	177.4 (2)	C17—C18—C19—C20	−1.1 (5)
C7—C16—C21—O2	−4.2 (4)	C21—C20—C19—C18	−0.3 (5)
C17—C16—C21—C20	−2.3 (4)	C36—C31—C32—C33	−0.3 (4)
C7—C16—C21—C20	176.1 (3)	C30—C31—C32—C33	−178.5 (2)
C42—C37—C38—C39	−0.4 (4)	C11—C10—C15—C14	−0.8 (4)
C28—C37—C38—C39	177.7 (2)	C9—C10—C15—C14	178.3 (3)
C5—N1—C8—O1	−176.6 (3)	C14—C13—C12—C11	−0.1 (5)
C9—N1—C8—O1	−4.7 (4)	C10—C11—C12—C13	−1.0 (5)
C5—N1—C8—C7	2.6 (3)	C12—C13—C14—C15	0.8 (5)
C9—N1—C8—C7	174.4 (2)	C10—C15—C14—C13	−0.3 (5)
C42—C41—C40—C39	0.2 (4)	C31—C36—C35—C34	0.3 (5)
C17—C16—C7—C6	−22.9 (4)	C31—C32—C33—C34	0.6 (5)
C21—C16—C7—C6	158.8 (2)	C36—C35—C34—C33	0.0 (5)
C17—C16—C7—C8	96.4 (3)	C32—C33—C34—C35	−0.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.82	1.93	2.721 (3)	160
O4—H4···O3^ii	0.82	1.95	2.735 (3)	160

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