4,4′-Methyl­enebis[N-(2-hy­droxy-3-meth­oxy­benzyl­idene)-2,6-diiso­propyl­aniline]

In the V-shaped title Schiff base, C₄₁H₅₀N₂O₄, the planes of the benzene rings of the central di­phenyl­methane unit make a dihedral angle of 70.40 (5)°, whereas the planes of the neighbouring benzene and ortho-vanilin rings are twisted with respect to one another by dihedral angles of 75.76 (5) and 73.89 (6)°. The Schiff base displays intra­molecular O—H...N hydrogen bonds and weak inter­molecular C—H...O contacts.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.126
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         C7 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          2 Note

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2017); cell refinement: CrysAlis PRO (Rigaku OD, 2017); data reduction: CrysAlis PRO (Rigaku OD, 2017); program(s) used to solve structure: SHELXT2015 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

4,4'-Methylenebis[N-(2-hydroxy-3-methoxybenzylidene)-2,6-diisopropylaniline]

Crystal data

C41H50N2O4	Z = 2
Mr = 634.83	F(000) = 684
Triclinic, P1	Dx = 1.135 Mg m^−3
a = 6.0155 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 16.5935 (3) Å	Cell parameters from 9193 reflections
c = 19.2093 (3) Å	θ = 2.3–31.1°
α = 101.541 (2)°	µ = 0.07 mm^−1
β = 97.341 (2)°	T = 150 K
γ = 92.928 (2)°	Needle, yellow
V = 1857.47 (6) Å^3	0.45 × 0.14 × 0.1 mm

Data collection

Rigaku Saturn 724+ diffractometer	6528 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	5207 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2017)	h = −7→7
Tmin = 0.701, Tmax = 1.000	k = −19→15
14358 measured reflections	l = −21→22

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0537P)^2 + 0.623P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
6528 reflections	Δρmax = 0.36 e Å^−3
440 parameters	Δρmin = −0.17 e Å^−3
2 restraints

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
O3	1.0025 (2)	0.74747 (8)	0.94420 (6)	0.0440 (3)
H3	0.951 (3)	0.7684 (12)	0.9080 (9)	0.053*
O1	0.7058 (2)	0.60969 (8)	0.22598 (7)	0.0516 (4)
H1	0.681 (4)	0.6413 (12)	0.2656 (9)	0.062*
N2	0.7464 (2)	0.82044 (8)	0.86122 (7)	0.0331 (3)
O4	1.0694 (3)	0.68864 (8)	1.06103 (7)	0.0578 (4)
N1	0.5193 (3)	0.67089 (8)	0.33770 (7)	0.0382 (3)
O2	0.6886 (3)	0.49933 (10)	0.10588 (8)	0.0728 (5)
C11	0.6910 (3)	0.84537 (10)	0.79454 (8)	0.0319 (4)
C1	0.5145 (3)	0.73131 (10)	0.40200 (8)	0.0359 (4)
C40	0.8509 (3)	0.76246 (9)	0.99044 (8)	0.0354 (4)
C12	0.8185 (3)	0.91305 (10)	0.78247 (9)	0.0365 (4)
C10	0.5268 (3)	0.79864 (10)	0.74104 (8)	0.0355 (4)
C34	0.6145 (3)	0.83185 (10)	0.90880 (8)	0.0371 (4)
H34	0.481609	0.858880	0.899791	0.044*
C6	0.6688 (3)	0.72676 (10)	0.46248 (8)	0.0373 (4)
C35	0.6612 (3)	0.80476 (10)	0.97640 (8)	0.0368 (4)
C39	0.8850 (3)	0.73198 (10)	1.05412 (9)	0.0419 (4)
C2	0.3717 (3)	0.79565 (10)	0.40243 (9)	0.0389 (4)
C26	0.3601 (3)	0.61353 (10)	0.31618 (9)	0.0406 (4)
H26	0.240549	0.611575	0.343812	0.049*
C20	0.4027 (3)	0.72003 (11)	0.74959 (9)	0.0415 (4)
H20	0.465958	0.708075	0.796857	0.050*
C27	0.3567 (3)	0.55148 (10)	0.25099 (9)	0.0437 (5)
C17	0.8142 (3)	0.65446 (11)	0.46037 (9)	0.0429 (4)
H17	0.850517	0.638445	0.410326	0.052*
C13	0.7696 (3)	0.93566 (10)	0.71661 (9)	0.0443 (5)
H13	0.854035	0.981442	0.707478	0.053*
C9	0.4843 (3)	0.82531 (11)	0.67685 (9)	0.0440 (4)
H9	0.370611	0.795636	0.640563	0.053*
C32	0.5288 (3)	0.55181 (10)	0.20858 (9)	0.0450 (5)
C5	0.6753 (3)	0.78841 (11)	0.52375 (9)	0.0445 (5)
H5	0.778531	0.786489	0.565046	0.053*
C8	0.6012 (4)	0.89338 (10)	0.66378 (9)	0.0479 (5)
C14	0.2141 (3)	0.80248 (11)	0.33507 (9)	0.0455 (5)
H14	0.156626	0.745187	0.309572	0.055*
C23	1.0007 (3)	0.96050 (11)	0.84052 (10)	0.0430 (4)
H23	1.060884	0.920571	0.869481	0.052*
C4	0.5351 (4)	0.85284 (10)	0.52639 (9)	0.0484 (5)
C38	0.7348 (4)	0.74707 (12)	1.10290 (10)	0.0541 (5)
H38	0.757654	0.726711	1.145902	0.065*
C3	0.3853 (4)	0.85535 (11)	0.46560 (9)	0.0461 (5)
H3A	0.289154	0.899146	0.467117	0.055*
C22	0.4396 (3)	0.64662 (11)	0.69073 (10)	0.0492 (5)
H22A	0.375698	0.656181	0.643808	0.074*
H22B	0.365593	0.596154	0.699171	0.074*
H22C	0.601106	0.640609	0.691609	0.074*
C25	0.9011 (4)	1.02789 (12)	0.89148 (11)	0.0559 (5)
H25A	0.837631	1.067768	0.864671	0.084*
H25B	1.019478	1.056175	0.929668	0.084*
H25C	0.782346	1.002839	0.912677	0.084*
C15	0.3467 (4)	0.83974 (13)	0.28492 (9)	0.0506 (5)
H15A	0.414913	0.894536	0.309715	0.076*
H15B	0.245340	0.844596	0.242036	0.076*
H15C	0.465146	0.804004	0.270828	0.076*
C36	0.5113 (4)	0.81944 (14)	1.02708 (10)	0.0561 (5)
H36	0.382589	0.848622	1.017936	0.067*
C19	1.0370 (3)	0.67380 (14)	0.51052 (11)	0.0572 (5)
H19A	1.115965	0.723219	0.501878	0.086*
H19B	1.130050	0.627070	0.501414	0.086*
H19C	1.008032	0.683539	0.560462	0.086*
C18	0.6850 (4)	0.57976 (12)	0.47611 (12)	0.0582 (5)
H18A	0.649514	0.592890	0.525320	0.087*
H18B	0.777577	0.532586	0.470693	0.087*
H18C	0.545238	0.565974	0.442407	0.087*
C31	0.5186 (4)	0.49171 (12)	0.14498 (10)	0.0564 (6)
C30	0.3394 (5)	0.43240 (13)	0.12604 (12)	0.0692 (7)
H30	0.333160	0.391143	0.083543	0.083*
C16	0.0106 (4)	0.85078 (14)	0.35006 (12)	0.0578 (5)
H16A	−0.068439	0.827835	0.384144	0.087*
H16B	−0.091097	0.846769	0.305168	0.087*
H16C	0.060441	0.908807	0.370516	0.087*
C24	1.1994 (4)	0.99674 (13)	0.81108 (13)	0.0617 (6)
H24A	1.256611	0.953185	0.777110	0.093*
H24B	1.319035	1.019800	0.850773	0.093*
H24C	1.149822	1.040428	0.786503	0.093*
C41	1.1111 (5)	0.65391 (13)	1.12360 (10)	0.0706 (7)
H41A	1.248975	0.624954	1.122168	0.106*
H41B	0.984325	0.614930	1.124753	0.106*
H41C	1.128626	0.698107	1.166670	0.106*
C37	0.5509 (4)	0.79164 (15)	1.08980 (11)	0.0638 (6)
H37	0.451395	0.803020	1.124549	0.077*
C28	0.1750 (4)	0.49100 (12)	0.22983 (12)	0.0594 (6)
H28	0.056929	0.490900	0.258265	0.071*
C29	0.1685 (5)	0.43223 (13)	0.16819 (14)	0.0733 (7)
H29	0.046251	0.391143	0.154217	0.088*
C7	0.5468 (5)	0.92094 (12)	0.59319 (10)	0.0707 (7)
H7A	0.662509	0.964598	0.590916	0.085*
H7B	0.400484	0.945705	0.592621	0.085*
C21	0.1526 (4)	0.73049 (15)	0.75052 (13)	0.0664 (6)
H21A	0.132640	0.773893	0.791564	0.100*
H21B	0.076116	0.678439	0.754658	0.100*
H21C	0.088405	0.745873	0.705952	0.100*
C33	0.6978 (6)	0.43475 (17)	0.04340 (12)	0.0931 (10)
H33A	0.562963	0.433193	0.008493	0.140*
H33B	0.705075	0.381452	0.057866	0.140*
H33C	0.831693	0.445924	0.021586	0.140*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3	0.0572 (8)	0.0496 (7)	0.0265 (6)	0.0123 (6)	0.0014 (6)	0.0118 (5)
O1	0.0671 (9)	0.0487 (8)	0.0317 (7)	−0.0023 (7)	0.0012 (6)	−0.0034 (6)
N2	0.0405 (8)	0.0335 (7)	0.0220 (7)	0.0002 (6)	−0.0033 (6)	0.0037 (5)
O4	0.0913 (11)	0.0533 (8)	0.0309 (7)	0.0170 (8)	−0.0017 (7)	0.0175 (6)
N1	0.0505 (9)	0.0356 (8)	0.0252 (7)	−0.0078 (7)	−0.0046 (6)	0.0073 (6)
O2	0.1026 (13)	0.0644 (10)	0.0392 (8)	0.0231 (9)	−0.0028 (9)	−0.0140 (7)
C11	0.0403 (10)	0.0314 (8)	0.0231 (8)	0.0068 (7)	0.0005 (7)	0.0048 (6)
C1	0.0474 (10)	0.0339 (9)	0.0238 (8)	−0.0136 (8)	−0.0004 (7)	0.0074 (7)
C40	0.0528 (11)	0.0272 (8)	0.0206 (8)	−0.0070 (7)	−0.0016 (7)	−0.0014 (6)
C12	0.0456 (10)	0.0312 (8)	0.0308 (9)	0.0059 (7)	0.0013 (8)	0.0039 (7)
C10	0.0440 (10)	0.0347 (9)	0.0253 (8)	0.0049 (7)	−0.0012 (7)	0.0035 (7)
C34	0.0405 (10)	0.0394 (9)	0.0271 (8)	0.0012 (8)	−0.0028 (8)	0.0021 (7)
C6	0.0467 (10)	0.0373 (9)	0.0269 (8)	−0.0122 (8)	−0.0015 (7)	0.0123 (7)
C35	0.0463 (10)	0.0367 (9)	0.0227 (8)	−0.0068 (8)	−0.0007 (7)	0.0010 (7)
C39	0.0659 (13)	0.0292 (9)	0.0247 (8)	−0.0065 (8)	−0.0062 (8)	0.0023 (7)
C2	0.0539 (11)	0.0337 (9)	0.0279 (9)	−0.0103 (8)	−0.0018 (8)	0.0118 (7)
C26	0.0509 (11)	0.0346 (9)	0.0340 (9)	−0.0047 (8)	−0.0066 (8)	0.0120 (7)
C20	0.0504 (11)	0.0399 (10)	0.0304 (9)	−0.0043 (8)	−0.0043 (8)	0.0068 (7)
C27	0.0602 (12)	0.0292 (9)	0.0358 (9)	−0.0024 (8)	−0.0153 (9)	0.0084 (7)
C17	0.0464 (11)	0.0505 (11)	0.0301 (9)	−0.0055 (8)	−0.0015 (8)	0.0109 (8)
C13	0.0710 (13)	0.0282 (9)	0.0331 (9)	0.0016 (8)	0.0050 (9)	0.0069 (7)
C9	0.0633 (12)	0.0355 (9)	0.0264 (9)	0.0033 (8)	−0.0115 (8)	0.0015 (7)
C32	0.0642 (13)	0.0312 (9)	0.0330 (9)	0.0043 (9)	−0.0162 (9)	0.0055 (7)
C5	0.0675 (13)	0.0390 (10)	0.0237 (8)	−0.0121 (9)	−0.0084 (8)	0.0124 (7)
C8	0.0873 (15)	0.0297 (9)	0.0239 (9)	0.0063 (9)	−0.0018 (9)	0.0045 (7)
C14	0.0637 (13)	0.0357 (9)	0.0329 (9)	−0.0065 (9)	−0.0103 (9)	0.0108 (7)
C23	0.0467 (11)	0.0372 (9)	0.0414 (10)	−0.0026 (8)	−0.0061 (8)	0.0086 (8)
C4	0.0871 (15)	0.0305 (9)	0.0255 (9)	−0.0078 (9)	−0.0034 (9)	0.0113 (7)
C38	0.0837 (16)	0.0504 (11)	0.0261 (9)	−0.0100 (11)	0.0034 (10)	0.0096 (8)
C3	0.0752 (14)	0.0320 (9)	0.0307 (9)	−0.0014 (9)	−0.0002 (9)	0.0118 (7)
C22	0.0581 (12)	0.0363 (10)	0.0476 (11)	−0.0005 (9)	−0.0047 (9)	0.0046 (8)
C25	0.0630 (14)	0.0471 (11)	0.0463 (11)	−0.0044 (10)	−0.0065 (10)	−0.0063 (9)
C15	0.0654 (13)	0.0596 (12)	0.0289 (9)	0.0106 (10)	0.0017 (9)	0.0161 (8)
C36	0.0599 (13)	0.0714 (14)	0.0363 (10)	0.0052 (11)	0.0093 (10)	0.0082 (10)
C19	0.0514 (12)	0.0735 (14)	0.0452 (11)	−0.0060 (10)	−0.0057 (9)	0.0193 (10)
C18	0.0619 (14)	0.0443 (11)	0.0690 (14)	−0.0009 (10)	−0.0026 (11)	0.0222 (10)
C31	0.0854 (16)	0.0401 (11)	0.0355 (10)	0.0170 (11)	−0.0143 (11)	0.0001 (8)
C30	0.108 (2)	0.0358 (11)	0.0472 (12)	0.0088 (12)	−0.0302 (14)	−0.0061 (9)
C16	0.0529 (13)	0.0660 (13)	0.0571 (13)	−0.0065 (10)	0.0005 (10)	0.0264 (11)
C24	0.0530 (13)	0.0530 (12)	0.0765 (15)	−0.0077 (10)	0.0031 (11)	0.0139 (11)
C41	0.129 (2)	0.0532 (12)	0.0291 (10)	0.0189 (13)	−0.0073 (12)	0.0165 (9)
C37	0.0763 (16)	0.0821 (16)	0.0348 (11)	−0.0007 (13)	0.0162 (11)	0.0128 (10)
C28	0.0726 (15)	0.0379 (10)	0.0572 (13)	−0.0126 (10)	−0.0186 (11)	0.0069 (9)
C29	0.097 (2)	0.0386 (12)	0.0668 (15)	−0.0155 (12)	−0.0330 (15)	0.0029 (11)
C7	0.144 (2)	0.0361 (10)	0.0273 (10)	0.0050 (12)	−0.0084 (12)	0.0081 (8)
C21	0.0582 (14)	0.0677 (14)	0.0706 (15)	−0.0051 (11)	0.0169 (12)	0.0056 (12)
C33	0.141 (3)	0.0810 (18)	0.0415 (13)	0.0436 (18)	−0.0069 (15)	−0.0201 (12)

Geometric parameters (Å, º)

O3—H3	0.867 (15)	C14—C16	1.524 (3)
O3—C40	1.351 (2)	C23—H23	1.0000
O1—H1	0.867 (15)	C23—C25	1.532 (3)
O1—C32	1.358 (2)	C23—C24	1.532 (3)
N2—C11	1.4283 (19)	C4—C3	1.390 (3)
N2—C34	1.278 (2)	C4—C7	1.522 (2)
O4—C39	1.359 (2)	C38—H38	0.9500
O4—C41	1.433 (2)	C38—C37	1.386 (3)
N1—C1	1.431 (2)	C3—H3A	0.9500
N1—C26	1.281 (2)	C22—H22A	0.9800
O2—C31	1.359 (3)	C22—H22B	0.9800
O2—C33	1.449 (2)	C22—H22C	0.9800
C11—C12	1.402 (2)	C25—H25A	0.9800
C11—C10	1.406 (2)	C25—H25B	0.9800
C1—C6	1.408 (2)	C25—H25C	0.9800
C1—C2	1.404 (3)	C15—H15A	0.9800
C40—C35	1.395 (3)	C15—H15B	0.9800
C40—C39	1.410 (2)	C15—H15C	0.9800
C12—C13	1.391 (2)	C36—H36	0.9500
C12—C23	1.521 (2)	C36—C37	1.372 (3)
C10—C20	1.518 (2)	C19—H19A	0.9800
C10—C9	1.390 (2)	C19—H19B	0.9800
C34—H34	0.9500	C19—H19C	0.9800
C34—C35	1.456 (2)	C18—H18A	0.9800
C6—C17	1.517 (3)	C18—H18B	0.9800
C6—C5	1.391 (2)	C18—H18C	0.9800
C35—C36	1.405 (3)	C31—C30	1.382 (3)
C39—C38	1.379 (3)	C30—H30	0.9500
C2—C14	1.530 (2)	C30—C29	1.388 (4)
C2—C3	1.395 (2)	C16—H16A	0.9800
C26—H26	0.9500	C16—H16B	0.9800
C26—C27	1.450 (2)	C16—H16C	0.9800
C20—H20	1.0000	C24—H24A	0.9800
C20—C22	1.534 (2)	C24—H24B	0.9800
C20—C21	1.525 (3)	C24—H24C	0.9800
C27—C32	1.397 (3)	C41—H41A	0.9800
C27—C28	1.406 (3)	C41—H41B	0.9800
C17—H17	1.0000	C41—H41C	0.9800
C17—C19	1.527 (3)	C37—H37	0.9500
C17—C18	1.531 (3)	C28—H28	0.9500
C13—H13	0.9500	C28—C29	1.370 (3)
C13—C8	1.388 (3)	C29—H29	0.9500
C9—H9	0.9500	C7—H7A	0.9900
C9—C8	1.382 (3)	C7—H7B	0.9900
C32—C31	1.406 (3)	C21—H21A	0.9800
C5—H5	0.9500	C21—H21B	0.9800
C5—C4	1.392 (3)	C21—H21C	0.9800
C8—C7	1.518 (2)	C33—H33A	0.9800
C14—H14	1.0000	C33—H33B	0.9800
C14—C15	1.527 (3)	C33—H33C	0.9800
C40—O3—H3	105.0 (13)	C2—C3—H3A	118.9
C32—O1—H1	104.8 (15)	C4—C3—C2	122.13 (18)
C34—N2—C11	120.48 (14)	C4—C3—H3A	118.9
C39—O4—C41	117.77 (17)	C20—C22—H22A	109.5
C26—N1—C1	120.19 (15)	C20—C22—H22B	109.5
C31—O2—C33	117.5 (2)	C20—C22—H22C	109.5
C12—C11—N2	117.70 (14)	H22A—C22—H22B	109.5
C12—C11—C10	121.75 (14)	H22A—C22—H22C	109.5
C10—C11—N2	120.32 (14)	H22B—C22—H22C	109.5
C6—C1—N1	117.43 (16)	C23—C25—H25A	109.5
C2—C1—N1	120.55 (15)	C23—C25—H25B	109.5
C2—C1—C6	121.87 (15)	C23—C25—H25C	109.5
O3—C40—C35	122.38 (14)	H25A—C25—H25B	109.5
O3—C40—C39	118.06 (16)	H25A—C25—H25C	109.5
C35—C40—C39	119.54 (16)	H25B—C25—H25C	109.5
C11—C12—C23	120.51 (15)	C14—C15—H15A	109.5
C13—C12—C11	117.75 (16)	C14—C15—H15B	109.5
C13—C12—C23	121.73 (16)	C14—C15—H15C	109.5
C11—C10—C20	123.08 (14)	H15A—C15—H15B	109.5
C9—C10—C11	117.40 (16)	H15A—C15—H15C	109.5
C9—C10—C20	119.48 (15)	H15B—C15—H15C	109.5
N2—C34—H34	118.9	C35—C36—H36	120.0
N2—C34—C35	122.13 (16)	C37—C36—C35	120.0 (2)
C35—C34—H34	118.9	C37—C36—H36	120.0
C1—C6—C17	120.00 (15)	C17—C19—H19A	109.5
C5—C6—C1	117.76 (16)	C17—C19—H19B	109.5
C5—C6—C17	122.20 (15)	C17—C19—H19C	109.5
C40—C35—C34	120.49 (15)	H19A—C19—H19B	109.5
C40—C35—C36	119.71 (16)	H19A—C19—H19C	109.5
C36—C35—C34	119.78 (17)	H19B—C19—H19C	109.5
O4—C39—C40	114.75 (16)	C17—C18—H18A	109.5
O4—C39—C38	125.72 (16)	C17—C18—H18B	109.5
C38—C39—C40	119.53 (18)	C17—C18—H18C	109.5
C1—C2—C14	121.32 (15)	H18A—C18—H18B	109.5
C3—C2—C1	117.64 (16)	H18A—C18—H18C	109.5
C3—C2—C14	120.98 (16)	H18B—C18—H18C	109.5
N1—C26—H26	118.9	O2—C31—C32	115.3 (2)
N1—C26—C27	122.13 (18)	O2—C31—C30	125.46 (19)
C27—C26—H26	118.9	C30—C31—C32	119.3 (2)
C10—C20—H20	107.8	C31—C30—H30	119.5
C10—C20—C22	111.11 (15)	C31—C30—C29	121.0 (2)
C10—C20—C21	111.23 (16)	C29—C30—H30	119.5
C22—C20—H20	107.8	C14—C16—H16A	109.5
C21—C20—H20	107.8	C14—C16—H16B	109.5
C21—C20—C22	110.92 (16)	C14—C16—H16C	109.5
C32—C27—C26	121.01 (16)	H16A—C16—H16B	109.5
C32—C27—C28	119.76 (18)	H16A—C16—H16C	109.5
C28—C27—C26	119.21 (19)	H16B—C16—H16C	109.5
C6—C17—H17	107.3	C23—C24—H24A	109.5
C6—C17—C19	114.19 (16)	C23—C24—H24B	109.5
C6—C17—C18	110.88 (15)	C23—C24—H24C	109.5
C19—C17—H17	107.3	H24A—C24—H24B	109.5
C19—C17—C18	109.68 (16)	H24A—C24—H24C	109.5
C18—C17—H17	107.3	H24B—C24—H24C	109.5
C12—C13—H13	119.0	O4—C41—H41A	109.5
C8—C13—C12	122.04 (17)	O4—C41—H41B	109.5
C8—C13—H13	119.0	O4—C41—H41C	109.5
C10—C9—H9	118.8	H41A—C41—H41B	109.5
C8—C9—C10	122.50 (17)	H41A—C41—H41C	109.5
C8—C9—H9	118.8	H41B—C41—H41C	109.5
O1—C32—C27	122.06 (16)	C38—C37—H37	119.7
O1—C32—C31	118.3 (2)	C36—C37—C38	120.5 (2)
C27—C32—C31	119.67 (19)	C36—C37—H37	119.7
C6—C5—H5	119.0	C27—C28—H28	120.0
C6—C5—C4	122.02 (16)	C29—C28—C27	120.0 (2)
C4—C5—H5	119.0	C29—C28—H28	120.0
C13—C8—C7	120.93 (18)	C30—C29—H29	119.8
C9—C8—C13	118.42 (16)	C28—C29—C30	120.4 (2)
C9—C8—C7	120.65 (18)	C28—C29—H29	119.8
C2—C14—H14	107.4	C8—C7—C4	114.93 (15)
C15—C14—C2	109.56 (16)	C8—C7—H7A	108.5
C15—C14—H14	107.4	C8—C7—H7B	108.5
C16—C14—C2	114.26 (16)	C4—C7—H7A	108.5
C16—C14—H14	107.4	C4—C7—H7B	108.5
C16—C14—C15	110.48 (15)	H7A—C7—H7B	107.5
C12—C23—H23	107.2	C20—C21—H21A	109.5
C12—C23—C25	110.64 (15)	C20—C21—H21B	109.5
C12—C23—C24	113.66 (16)	C20—C21—H21C	109.5
C25—C23—H23	107.2	H21A—C21—H21B	109.5
C24—C23—H23	107.2	H21A—C21—H21C	109.5
C24—C23—C25	110.75 (16)	H21B—C21—H21C	109.5
C5—C4—C7	121.60 (17)	O2—C33—H33A	109.5
C3—C4—C5	118.58 (16)	O2—C33—H33B	109.5
C3—C4—C7	119.80 (18)	O2—C33—H33C	109.5
C39—C38—H38	119.7	H33A—C33—H33B	109.5
C39—C38—C37	120.64 (18)	H33A—C33—H33C	109.5
C37—C38—H38	119.7	H33B—C33—H33C	109.5
O3—C40—C35—C34	2.5 (2)	C6—C1—C2—C14	176.57 (15)
O3—C40—C35—C36	−179.12 (16)	C6—C1—C2—C3	−0.7 (2)
O3—C40—C39—O4	−1.1 (2)	C6—C5—C4—C3	−0.3 (3)
O3—C40—C39—C38	179.22 (16)	C6—C5—C4—C7	−178.75 (18)
O1—C32—C31—O2	−1.5 (2)	C35—C40—C39—O4	177.23 (15)
O1—C32—C31—C30	−179.72 (17)	C35—C40—C39—C38	−2.4 (2)
N2—C11—C12—C13	177.89 (15)	C35—C36—C37—C38	−1.8 (3)
N2—C11—C12—C23	−3.2 (2)	C39—C40—C35—C34	−175.79 (15)
N2—C11—C10—C20	−0.9 (2)	C39—C40—C35—C36	2.6 (3)
N2—C11—C10—C9	−178.65 (15)	C39—C38—C37—C36	1.9 (3)
N2—C34—C35—C40	−2.1 (3)	C2—C1—C6—C17	177.89 (15)
N2—C34—C35—C36	179.51 (17)	C2—C1—C6—C5	0.3 (2)
O4—C39—C38—C37	−179.43 (19)	C26—N1—C1—C6	108.15 (19)
N1—C1—C6—C17	−6.6 (2)	C26—N1—C1—C2	−76.2 (2)
N1—C1—C6—C5	175.87 (15)	C26—C27—C32—O1	−0.1 (3)
N1—C1—C2—C14	1.2 (2)	C26—C27—C32—C31	−178.83 (16)
N1—C1—C2—C3	−176.08 (15)	C26—C27—C28—C29	179.62 (18)
N1—C26—C27—C32	0.0 (3)	C20—C10—C9—C8	−175.86 (17)
N1—C26—C27—C28	−178.98 (17)	C27—C32—C31—O2	177.26 (16)
O2—C31—C30—C29	−177.0 (2)	C27—C32—C31—C30	−1.0 (3)
C11—N2—C34—C35	177.84 (15)	C27—C28—C29—C30	−0.6 (3)
C11—C12—C13—C8	−0.1 (3)	C17—C6—C5—C4	−177.33 (17)
C11—C12—C23—C25	−86.5 (2)	C13—C12—C23—C25	92.4 (2)
C11—C12—C23—C24	148.19 (17)	C13—C12—C23—C24	−33.0 (2)
C11—C10—C20—C22	−121.14 (18)	C13—C8—C7—C4	130.3 (2)
C11—C10—C20—C21	114.75 (19)	C9—C10—C20—C22	56.6 (2)
C11—C10—C9—C8	2.0 (3)	C9—C10—C20—C21	−67.5 (2)
C1—N1—C26—C27	179.37 (15)	C9—C8—C7—C4	−49.5 (3)
C1—C6—C17—C19	153.14 (16)	C32—C27—C28—C29	0.6 (3)
C1—C6—C17—C18	−82.3 (2)	C32—C31—C30—C29	1.1 (3)
C1—C6—C5—C4	0.2 (3)	C5—C6—C17—C19	−29.4 (2)
C1—C2—C14—C15	−79.1 (2)	C5—C6—C17—C18	95.1 (2)
C1—C2—C14—C16	156.29 (16)	C5—C4—C3—C2	−0.1 (3)
C1—C2—C3—C4	0.5 (3)	C5—C4—C7—C8	−34.7 (3)
C40—C35—C36—C37	−0.5 (3)	C14—C2—C3—C4	−176.71 (17)
C40—C39—C38—C37	0.2 (3)	C23—C12—C13—C8	−179.00 (17)
C12—C11—C10—C20	173.55 (15)	C3—C2—C14—C15	98.0 (2)
C12—C11—C10—C9	−4.2 (2)	C3—C2—C14—C16	−26.6 (2)
C12—C13—C8—C9	−2.0 (3)	C3—C4—C7—C8	146.9 (2)
C12—C13—C8—C7	178.19 (19)	C31—C30—C29—C28	−0.3 (3)
C10—C11—C12—C13	3.3 (2)	C41—O4—C39—C40	−178.36 (16)
C10—C11—C12—C23	−177.79 (15)	C41—O4—C39—C38	1.3 (3)
C10—C9—C8—C13	1.0 (3)	C28—C27—C32—O1	178.83 (16)
C10—C9—C8—C7	−179.16 (19)	C28—C27—C32—C31	0.1 (3)
C34—N2—C11—C12	109.56 (18)	C7—C4—C3—C2	178.41 (19)
C34—N2—C11—C10	−75.8 (2)	C33—O2—C31—C32	174.40 (18)
C34—C35—C36—C37	177.86 (19)	C33—O2—C31—C30	−7.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.87 (2)	1.79 (2)	2.5912 (17)	153 (2)
O1—H1···N1	0.87 (2)	1.80 (2)	2.5991 (19)	153 (2)
C41—H41B···O2^i	0.98	2.49	3.452 (3)	168

Symmetry code: (i) x, y, z+1.