Crystal structure, Hirshfeld surface and frontier mol­ecular orbital analysis of 10-benzyl-9-(3-eth­oxy-4-hy­droxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,6,7,9,10-hexa­hydro­acridine-1,8(2H,5H)-dione

In the acridinedione moiety of the title compound, the central ring adopts a flattened-boat conformation, whereas the cyclo­hexenone rings adopt envelope conformations.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.049
• wR factor = 0.139
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.
DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Alert level C
PLAT220_ALERT_2_C NonSolvent Resd 1  C   Ueq(max) / Ueq(min) Range        3.6 Ratio
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        4.2 Ratio
PLAT241_ALERT_2_C High   MainMol Ueq as Compared to Neighbors of         O2 Check
PLAT242_ALERT_2_C Low    MainMol Ueq as Compared to Neighbors of        C21 Check
PLAT410_ALERT_2_C Short Intra H...H Contact  H20A     ..H26B     .       1.98 Ang.
                                                      x,y,z  =      1_555 Check
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.197 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          5 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          4 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3 Note
PLAT230_ALERT_2_G Hirshfeld Test Diff for    O2       --C7'      .        7.7 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         5% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          5 Note
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         39 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        43% Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 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
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX3 (Bruker, 2004); cell refinement: APEX3 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015).

10-Benzyl-9-(3-ethoxy-4-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione

Crystal data

C32H37NO4	F(000) = 1072
Mr = 499.62	Dx = 1.250 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.5780 (2) Å	Cell parameters from 5176 reflections
b = 18.4190 (5) Å	θ = 2.1–23.3°
c = 14.3980 (3) Å	µ = 0.08 mm^−1
β = 108.791 (1)°	T = 296 K
V = 2655.73 (10) Å^3	Block, yellow
Z = 4	0.35 × 0.30 × 0.30 mm

Data collection

Bruker Kappa APEXII diffractometer	4681 independent reflections
Radiation source: fine-focus sealed tube	3374 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω and φ scan	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.674, Tmax = 0.746	k = −21→21
23101 measured reflections	l = −17→17

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0564P)^2 + 1.304P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.139	(Δ/σ)max = 0.003
S = 1.02	Δρmax = 0.37 e Å^−3
4681 reflections	Δρmin = −0.24 e Å^−3
364 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
39 restraints	Extinction coefficient: 0.0066 (9)

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)
C1	0.7372 (2)	0.07235 (11)	1.19469 (15)	0.0471 (5)
C2	0.7273 (2)	0.10618 (12)	1.10816 (15)	0.0488 (5)
H2	0.777437	0.089182	1.070203	0.059*
C3	0.6443 (2)	0.16503 (12)	1.07625 (15)	0.0461 (5)
H3	0.640119	0.187332	1.017378	0.055*
C4	0.5675 (2)	0.19150 (11)	1.12980 (14)	0.0407 (5)
C5	0.5779 (2)	0.15710 (12)	1.21800 (15)	0.0485 (5)
H5	0.527092	0.173864	1.255627	0.058*
C6	0.6615 (2)	0.09894 (13)	1.25058 (15)	0.0525 (6)
C9	0.7670 (2)	0.33092 (16)	0.9497 (2)	0.0704 (7)
H9A	0.754428	0.297468	0.997122	0.106*
H9B	0.841043	0.362289	0.980882	0.106*
H9C	0.785001	0.304417	0.897943	0.106*
C10	0.6623 (3)	0.42747 (15)	0.8297 (2)	0.0741 (8)
H10A	0.676549	0.399414	0.777748	0.111*
H10B	0.738811	0.457558	0.859168	0.111*
H10C	0.584716	0.457489	0.803512	0.111*
C11	0.6411 (2)	0.37629 (12)	0.90727 (17)	0.0524 (6)
C12	0.6105 (3)	0.41915 (12)	0.98762 (19)	0.0604 (6)
H12A	0.687205	0.448978	1.021231	0.072*
H12B	0.535806	0.451328	0.957972	0.072*
C13	0.5775 (2)	0.37160 (11)	1.06128 (16)	0.0465 (5)
C14	0.5053 (2)	0.30484 (10)	1.02566 (15)	0.0416 (5)
C15	0.46639 (19)	0.28917 (10)	0.92851 (14)	0.0397 (5)
C16	0.5213 (2)	0.32806 (12)	0.85821 (16)	0.0492 (5)
H16A	0.451065	0.357700	0.814830	0.059*
H16B	0.547020	0.292318	0.818172	0.059*
C17	0.4695 (2)	0.25444 (11)	1.09529 (14)	0.0426 (5)
H17	0.468205	0.282359	1.152911	0.051*
C18	0.3300 (2)	0.22705 (11)	1.04337 (15)	0.0432 (5)
C19	0.29089 (19)	0.21317 (11)	0.94584 (15)	0.0399 (5)
C20	0.1604 (2)	0.17691 (12)	0.89287 (16)	0.0473 (5)
H20A	0.176648	0.138375	0.852218	0.057*
H20B	0.102079	0.212117	0.849634	0.057*
C21	0.0881 (2)	0.14485 (12)	0.95949 (17)	0.0509 (5)
C22	0.0967 (2)	0.19754 (14)	1.04238 (19)	0.0624 (7)
H22A	0.047079	0.241160	1.015377	0.075*
H22B	0.055315	0.175713	1.086706	0.075*
C23	0.2381 (2)	0.21791 (13)	1.09917 (18)	0.0548 (6)
C26	0.3491 (2)	0.20767 (12)	0.79067 (14)	0.0455 (5)
H26A	0.357805	0.246910	0.748202	0.055*
H26B	0.259352	0.188286	0.764455	0.055*
C27	0.4480 (2)	0.14911 (12)	0.79111 (14)	0.0457 (5)
C28	0.5291 (3)	0.15385 (17)	0.73326 (18)	0.0697 (7)
H28	0.522216	0.193597	0.692092	0.084*
C29	0.6213 (3)	0.0992 (2)	0.7363 (2)	0.0898 (10)
H29	0.676908	0.102922	0.697950	0.108*
C30	0.6304 (3)	0.0403 (2)	0.7953 (2)	0.0856 (9)
H30	0.691243	0.003581	0.796294	0.103*
C31	0.5509 (3)	0.03490 (15)	0.8525 (2)	0.0720 (7)
H31	0.557448	−0.005257	0.892928	0.086*
C32	0.4609 (2)	0.08898 (13)	0.85044 (18)	0.0568 (6)
H32	0.407100	0.084969	0.890121	0.068*
N1	0.37004 (16)	0.23636 (9)	0.89039 (11)	0.0398 (4)
O1	0.82089 (18)	0.01441 (9)	1.22322 (14)	0.0647 (5)
O3	0.60779 (17)	0.39009 (9)	1.14761 (12)	0.0612 (5)
O4	0.27281 (18)	0.22766 (12)	1.18772 (13)	0.0788 (6)
O2	0.6794 (2)	0.06291 (12)	1.33650 (13)	0.0898 (7)
C7	0.5937 (8)	0.0989 (5)	1.3972 (5)	0.079 (2)	0.572 (11)
H7A	0.611903	0.150541	1.405357	0.095*	0.572 (11)
H7B	0.499043	0.092146	1.363367	0.095*	0.572 (11)
C8	0.6318 (9)	0.0638 (6)	1.4895 (5)	0.131 (4)	0.572 (11)
H8A	0.580043	0.082713	1.527912	0.197*	0.572 (11)
H8B	0.724873	0.072391	1.523026	0.197*	0.572 (11)
H8C	0.616247	0.012594	1.480136	0.197*	0.572 (11)
C7'	0.5829 (9)	0.0565 (6)	1.3908 (6)	0.082 (3)	0.428 (11)
H7'1	0.493748	0.073595	1.354927	0.099*	0.428 (11)
H7'2	0.580760	0.009096	1.419461	0.099*	0.428 (11)
C8'	0.6622 (12)	0.1071 (5)	1.4551 (10)	0.142 (6)	0.428 (11)
H8'1	0.621787	0.119635	1.503820	0.213*	0.428 (11)
H8'2	0.670497	0.149885	1.419379	0.213*	0.428 (11)
H8'3	0.749065	0.086785	1.486481	0.213*	0.428 (11)
C24	0.1545 (3)	0.07364 (14)	1.0030 (2)	0.0769 (8)
H24A	0.247265	0.082123	1.037911	0.115*
H24B	0.146600	0.039373	0.951142	0.115*
H24C	0.111638	0.054559	1.047206	0.115*
C25	−0.0558 (3)	0.13003 (19)	0.8986 (2)	0.0835 (9)
H25A	−0.102569	0.109844	0.939704	0.125*
H25B	−0.058132	0.096260	0.847274	0.125*
H25C	−0.097909	0.174597	0.870218	0.125*
H1	0.814 (3)	−0.0069 (19)	1.274 (2)	0.107 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0481 (12)	0.0434 (12)	0.0435 (12)	−0.0042 (10)	0.0057 (10)	0.0027 (9)
C2	0.0544 (13)	0.0500 (13)	0.0443 (12)	0.0038 (10)	0.0191 (10)	0.0019 (10)
C3	0.0534 (13)	0.0499 (12)	0.0357 (11)	0.0010 (10)	0.0152 (10)	0.0048 (9)
C4	0.0436 (11)	0.0414 (11)	0.0349 (10)	−0.0094 (9)	0.0095 (9)	−0.0062 (8)
C5	0.0573 (13)	0.0536 (13)	0.0368 (11)	−0.0063 (11)	0.0182 (10)	−0.0047 (10)
C6	0.0629 (14)	0.0573 (14)	0.0346 (11)	−0.0069 (11)	0.0117 (10)	0.0063 (10)
C9	0.0469 (14)	0.0768 (18)	0.0881 (19)	0.0009 (13)	0.0225 (13)	0.0029 (15)
C10	0.0785 (18)	0.0664 (17)	0.0857 (19)	−0.0175 (14)	0.0380 (16)	0.0090 (14)
C11	0.0513 (13)	0.0459 (12)	0.0629 (14)	−0.0066 (10)	0.0225 (11)	0.0020 (11)
C12	0.0676 (16)	0.0403 (12)	0.0767 (16)	−0.0118 (11)	0.0279 (13)	−0.0050 (11)
C13	0.0421 (12)	0.0409 (11)	0.0535 (13)	0.0006 (9)	0.0112 (10)	−0.0068 (10)
C14	0.0402 (11)	0.0378 (11)	0.0467 (12)	0.0005 (9)	0.0140 (9)	−0.0024 (9)
C15	0.0364 (10)	0.0361 (10)	0.0446 (11)	0.0019 (8)	0.0103 (9)	0.0011 (9)
C16	0.0499 (13)	0.0480 (12)	0.0483 (12)	−0.0032 (10)	0.0140 (10)	0.0068 (10)
C17	0.0466 (12)	0.0435 (11)	0.0382 (11)	−0.0045 (9)	0.0143 (9)	−0.0085 (9)
C18	0.0434 (11)	0.0431 (12)	0.0443 (12)	−0.0004 (9)	0.0155 (9)	−0.0025 (9)
C19	0.0362 (11)	0.0382 (11)	0.0456 (11)	0.0011 (8)	0.0135 (9)	0.0010 (9)
C20	0.0399 (11)	0.0487 (12)	0.0500 (12)	−0.0035 (10)	0.0097 (10)	0.0016 (10)
C21	0.0437 (12)	0.0470 (12)	0.0629 (14)	−0.0055 (10)	0.0184 (11)	0.0014 (11)
C22	0.0540 (14)	0.0650 (16)	0.0768 (17)	−0.0006 (12)	0.0329 (13)	0.0002 (13)
C23	0.0576 (14)	0.0559 (14)	0.0565 (14)	−0.0013 (11)	0.0263 (12)	−0.0049 (11)
C26	0.0463 (12)	0.0533 (13)	0.0338 (10)	−0.0077 (10)	0.0085 (9)	0.0000 (9)
C27	0.0403 (11)	0.0582 (13)	0.0357 (11)	−0.0093 (10)	0.0084 (9)	−0.0125 (10)
C28	0.0666 (16)	0.096 (2)	0.0527 (14)	−0.0061 (15)	0.0276 (13)	−0.0071 (14)
C29	0.0633 (18)	0.141 (3)	0.073 (2)	0.006 (2)	0.0337 (16)	−0.026 (2)
C30	0.0634 (18)	0.103 (2)	0.083 (2)	0.0173 (17)	0.0123 (16)	−0.0294 (19)
C31	0.0641 (16)	0.0656 (17)	0.0790 (19)	0.0055 (13)	0.0127 (15)	−0.0123 (14)
C32	0.0535 (14)	0.0560 (14)	0.0615 (15)	−0.0020 (11)	0.0191 (12)	−0.0089 (12)
N1	0.0391 (9)	0.0421 (9)	0.0372 (9)	−0.0040 (7)	0.0108 (7)	−0.0021 (7)
O1	0.0711 (11)	0.0564 (10)	0.0623 (11)	0.0109 (9)	0.0154 (9)	0.0187 (9)
O3	0.0687 (11)	0.0526 (10)	0.0549 (10)	−0.0101 (8)	0.0097 (8)	−0.0138 (8)
O4	0.0754 (12)	0.1155 (16)	0.0554 (11)	−0.0146 (11)	0.0348 (9)	−0.0161 (10)
O2	0.1117 (16)	0.1106 (16)	0.0534 (11)	0.0161 (13)	0.0353 (11)	0.0358 (11)
C7	0.091 (5)	0.082 (5)	0.070 (4)	0.018 (5)	0.036 (3)	0.029 (4)
C8	0.182 (7)	0.154 (8)	0.090 (5)	0.087 (6)	0.091 (5)	0.041 (4)
C7'	0.084 (5)	0.059 (5)	0.084 (6)	−0.018 (4)	−0.002 (4)	0.027 (5)
C8'	0.138 (9)	0.073 (6)	0.136 (9)	−0.032 (6)	−0.066 (7)	0.034 (6)
C24	0.091 (2)	0.0520 (15)	0.090 (2)	−0.0023 (14)	0.0310 (17)	0.0113 (14)
C25	0.0545 (16)	0.103 (2)	0.091 (2)	−0.0266 (15)	0.0210 (15)	−0.0013 (18)

Geometric parameters (Å, º)

C1—O1	1.363 (3)	C21—C22	1.518 (3)
C1—C2	1.367 (3)	C21—C24	1.524 (3)
C1—C6	1.394 (3)	C22—C23	1.503 (3)
C2—C3	1.377 (3)	C22—H22A	0.9700
C2—H2	0.9300	C22—H22B	0.9700
C3—C4	1.377 (3)	C23—O4	1.221 (3)
C3—H3	0.9300	C26—N1	1.478 (2)
C4—C5	1.391 (3)	C26—C27	1.501 (3)
C4—C17	1.527 (3)	C26—H26A	0.9700
C5—C6	1.372 (3)	C26—H26B	0.9700
C5—H5	0.9300	C27—C28	1.377 (3)
C6—O2	1.362 (3)	C27—C32	1.378 (3)
C9—C11	1.524 (3)	C28—C29	1.393 (4)
C9—H9A	0.9600	C28—H28	0.9300
C9—H9B	0.9600	C29—C30	1.362 (5)
C9—H9C	0.9600	C29—H29	0.9300
C10—C11	1.532 (3)	C30—C31	1.357 (4)
C10—H10A	0.9600	C30—H30	0.9300
C10—H10B	0.9600	C31—C32	1.372 (3)
C10—H10C	0.9600	C31—H31	0.9300
C11—C12	1.519 (3)	C32—H32	0.9300
C11—C16	1.522 (3)	O1—H1	0.85 (3)
C12—C13	1.501 (3)	O2—C7'	1.476 (9)
C12—H12A	0.9700	O2—C7	1.592 (6)
C12—H12B	0.9700	C7—C8	1.414 (10)
C13—O3	1.228 (3)	C7—H7A	0.9700
C13—C14	1.451 (3)	C7—H7B	0.9700
C14—C15	1.356 (3)	C8—H8A	0.9600
C14—C17	1.502 (3)	C8—H8B	0.9600
C15—N1	1.388 (2)	C8—H8C	0.9600
C15—C16	1.501 (3)	C7'—C8'	1.389 (12)
C16—H16A	0.9700	C7'—H7'1	0.9700
C16—H16B	0.9700	C7'—H7'2	0.9700
C17—C18	1.510 (3)	C8'—H8'1	0.9600
C17—H17	0.9800	C8'—H8'2	0.9600
C18—C19	1.354 (3)	C8'—H8'3	0.9600
C18—C23	1.456 (3)	C24—H24A	0.9600
C19—N1	1.397 (2)	C24—H24B	0.9600
C19—C20	1.502 (3)	C24—H24C	0.9600
C20—C21	1.525 (3)	C25—H25A	0.9600
C20—H20A	0.9700	C25—H25B	0.9600
C20—H20B	0.9700	C25—H25C	0.9600
C21—C25	1.517 (3)
O1—C1—C2	118.9 (2)	C25—C21—C20	108.6 (2)
O1—C1—C6	122.6 (2)	C22—C21—C20	109.37 (18)
C2—C1—C6	118.5 (2)	C24—C21—C20	109.46 (19)
C1—C2—C3	121.1 (2)	C23—C22—C21	112.62 (19)
C1—C2—H2	119.5	C23—C22—H22A	109.1
C3—C2—H2	119.5	C21—C22—H22A	109.1
C2—C3—C4	121.29 (19)	C23—C22—H22B	109.1
C2—C3—H3	119.4	C21—C22—H22B	109.1
C4—C3—H3	119.4	H22A—C22—H22B	107.8
C3—C4—C5	117.5 (2)	O4—C23—C18	122.0 (2)
C3—C4—C17	123.20 (18)	O4—C23—C22	121.1 (2)
C5—C4—C17	119.22 (18)	C18—C23—C22	116.9 (2)
C6—C5—C4	121.3 (2)	N1—C26—C27	111.52 (16)
C6—C5—H5	119.3	N1—C26—H26A	109.3
C4—C5—H5	119.3	C27—C26—H26A	109.3
O2—C6—C5	125.2 (2)	N1—C26—H26B	109.3
O2—C6—C1	114.6 (2)	C27—C26—H26B	109.3
C5—C6—C1	120.26 (19)	H26A—C26—H26B	108.0
C11—C9—H9A	109.5	C28—C27—C32	118.0 (2)
C11—C9—H9B	109.5	C28—C27—C26	121.4 (2)
H9A—C9—H9B	109.5	C32—C27—C26	120.63 (19)
C11—C9—H9C	109.5	C27—C28—C29	120.1 (3)
H9A—C9—H9C	109.5	C27—C28—H28	120.0
H9B—C9—H9C	109.5	C29—C28—H28	120.0
C11—C10—H10A	109.5	C30—C29—C28	120.2 (3)
C11—C10—H10B	109.5	C30—C29—H29	119.9
H10A—C10—H10B	109.5	C28—C29—H29	119.9
C11—C10—H10C	109.5	C31—C30—C29	120.2 (3)
H10A—C10—H10C	109.5	C31—C30—H30	119.9
H10B—C10—H10C	109.5	C29—C30—H30	119.9
C12—C11—C16	107.89 (18)	C30—C31—C32	119.7 (3)
C12—C11—C9	110.6 (2)	C30—C31—H31	120.1
C16—C11—C9	110.84 (19)	C32—C31—H31	120.1
C12—C11—C10	110.6 (2)	C31—C32—C27	121.7 (2)
C16—C11—C10	108.4 (2)	C31—C32—H32	119.1
C9—C11—C10	108.4 (2)	C27—C32—H32	119.1
C13—C12—C11	112.95 (18)	C15—N1—C19	119.16 (16)
C13—C12—H12A	109.0	C15—N1—C26	119.72 (16)
C11—C12—H12A	109.0	C19—N1—C26	121.07 (16)
C13—C12—H12B	109.0	C1—O1—H1	113 (2)
C11—C12—H12B	109.0	C6—O2—C7'	127.0 (4)
H12A—C12—H12B	107.8	C6—O2—C7	111.0 (3)
O3—C13—C14	121.9 (2)	C8—C7—O2	106.6 (5)
O3—C13—C12	120.6 (2)	C8—C7—H7A	110.4
C14—C13—C12	117.41 (19)	O2—C7—H7A	110.4
C15—C14—C13	119.70 (19)	C8—C7—H7B	110.4
C15—C14—C17	119.93 (18)	O2—C7—H7B	110.4
C13—C14—C17	120.33 (18)	H7A—C7—H7B	108.6
C14—C15—N1	119.84 (18)	C7—C8—H8A	109.5
C14—C15—C16	122.63 (18)	C7—C8—H8B	109.5
N1—C15—C16	117.52 (17)	H8A—C8—H8B	109.5
C15—C16—C11	114.24 (18)	C7—C8—H8C	109.5
C15—C16—H16A	108.7	H8A—C8—H8C	109.5
C11—C16—H16A	108.7	H8B—C8—H8C	109.5
C15—C16—H16B	108.7	C8'—C7'—O2	85.9 (9)
C11—C16—H16B	108.7	C8'—C7'—H7'1	114.3
H16A—C16—H16B	107.6	O2—C7'—H7'1	114.3
C14—C17—C18	107.01 (16)	C8'—C7'—H7'2	114.3
C14—C17—C4	113.31 (16)	O2—C7'—H7'2	114.3
C18—C17—C4	111.10 (16)	H7'1—C7'—H7'2	111.5
C14—C17—H17	108.4	C7'—C8'—H8'1	109.5
C18—C17—H17	108.4	C7'—C8'—H8'2	109.5
C4—C17—H17	108.4	H8'1—C8'—H8'2	109.5
C19—C18—C23	121.0 (2)	C7'—C8'—H8'3	109.5
C19—C18—C17	119.97 (18)	H8'1—C8'—H8'3	109.5
C23—C18—C17	119.00 (18)	H8'2—C8'—H8'3	109.5
C18—C19—N1	119.73 (18)	C21—C24—H24A	109.5
C18—C19—C20	122.28 (18)	C21—C24—H24B	109.5
N1—C19—C20	117.90 (17)	H24A—C24—H24B	109.5
C19—C20—C21	114.70 (18)	C21—C24—H24C	109.5
C19—C20—H20A	108.6	H24A—C24—H24C	109.5
C21—C20—H20A	108.6	H24B—C24—H24C	109.5
C19—C20—H20B	108.6	C21—C25—H25A	109.5
C21—C20—H20B	108.6	C21—C25—H25B	109.5
H20A—C20—H20B	107.6	H25A—C25—H25B	109.5
C25—C21—C22	111.4 (2)	C21—C25—H25C	109.5
C25—C21—C24	109.1 (2)	H25A—C25—H25C	109.5
C22—C21—C24	108.9 (2)	H25B—C25—H25C	109.5
O1—C1—C2—C3	−179.9 (2)	C17—C18—C19—N1	−11.6 (3)
C6—C1—C2—C3	−0.3 (3)	C23—C18—C19—C20	−9.8 (3)
C1—C2—C3—C4	−0.6 (3)	C17—C18—C19—C20	171.90 (18)
C2—C3—C4—C5	0.7 (3)	C18—C19—C20—C21	−10.6 (3)
C2—C3—C4—C17	−177.22 (19)	N1—C19—C20—C21	172.77 (18)
C3—C4—C5—C6	0.0 (3)	C19—C20—C21—C25	164.0 (2)
C17—C4—C5—C6	178.02 (19)	C19—C20—C21—C22	42.2 (3)
C4—C5—C6—O2	178.9 (2)	C19—C20—C21—C24	−77.1 (2)
C4—C5—C6—C1	−0.9 (3)	C25—C21—C22—C23	−175.4 (2)
O1—C1—C6—O2	0.8 (3)	C24—C21—C22—C23	64.2 (3)
C2—C1—C6—O2	−178.8 (2)	C20—C21—C22—C23	−55.4 (3)
O1—C1—C6—C5	−179.5 (2)	C19—C18—C23—O4	177.4 (2)
C2—C1—C6—C5	1.0 (3)	C17—C18—C23—O4	−4.3 (3)
C16—C11—C12—C13	56.7 (3)	C19—C18—C23—C22	−4.1 (3)
C9—C11—C12—C13	−64.7 (3)	C17—C18—C23—C22	174.2 (2)
C10—C11—C12—C13	175.2 (2)	C21—C22—C23—O4	−143.8 (2)
C11—C12—C13—O3	147.3 (2)	C21—C22—C23—C18	37.6 (3)
C11—C12—C13—C14	−34.7 (3)	N1—C26—C27—C28	−124.2 (2)
O3—C13—C14—C15	175.6 (2)	N1—C26—C27—C32	55.3 (3)
C12—C13—C14—C15	−2.4 (3)	C32—C27—C28—C29	−0.5 (4)
O3—C13—C14—C17	−2.3 (3)	C26—C27—C28—C29	179.0 (2)
C12—C13—C14—C17	179.70 (19)	C27—C28—C29—C30	1.0 (4)
C13—C14—C15—N1	−163.65 (18)	C28—C29—C30—C31	−0.9 (5)
C17—C14—C15—N1	14.2 (3)	C29—C30—C31—C32	0.3 (4)
C13—C14—C15—C16	14.9 (3)	C30—C31—C32—C27	0.3 (4)
C17—C14—C15—C16	−167.17 (18)	C28—C27—C32—C31	−0.2 (3)
C14—C15—C16—C11	10.5 (3)	C26—C27—C32—C31	−179.7 (2)
N1—C15—C16—C11	−170.87 (18)	C14—C15—N1—C19	16.0 (3)
C12—C11—C16—C15	−44.9 (2)	C16—C15—N1—C19	−162.68 (18)
C9—C11—C16—C15	76.4 (2)	C14—C15—N1—C26	−166.38 (18)
C10—C11—C16—C15	−164.7 (2)	C16—C15—N1—C26	15.0 (3)
C15—C14—C17—C18	−38.2 (2)	C18—C19—N1—C15	−17.3 (3)
C13—C14—C17—C18	139.68 (18)	C20—C19—N1—C15	159.41 (18)
C15—C14—C17—C4	84.6 (2)	C18—C19—N1—C26	165.12 (18)
C13—C14—C17—C4	−97.5 (2)	C20—C19—N1—C26	−18.2 (3)
C3—C4—C17—C14	−25.6 (3)	C27—C26—N1—C15	82.8 (2)
C5—C4—C17—C14	156.47 (18)	C27—C26—N1—C19	−99.7 (2)
C3—C4—C17—C18	94.9 (2)	C5—C6—O2—C7'	26.6 (6)
C5—C4—C17—C18	−83.0 (2)	C1—C6—O2—C7'	−153.6 (5)
C14—C17—C18—C19	36.8 (2)	C5—C6—O2—C7	−2.0 (5)
C4—C17—C18—C19	−87.4 (2)	C1—C6—O2—C7	177.7 (4)
C14—C17—C18—C23	−141.50 (19)	C6—O2—C7—C8	−172.7 (8)
C4—C17—C18—C23	94.3 (2)	C6—O2—C7'—C8'	−104.5 (6)
C23—C18—C19—N1	166.72 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3^i	0.85 (3)	2.23 (4)	2.893 (2)	135 (3)
C26—H26B···O3^ii	0.97	2.40	3.258 (3)	148

Symmetry codes: (i) −x+3/2, y−1/2, −z+5/2; (ii) x−1/2, −y+1/2, z−1/2.