7-{3-Eth­oxy-4-[2-(2-meth­oxy­eth­oxy)eth­oxy]phen­yl}-5,6,8,9-tetra­hydro­dibenzo[c,h]acridine

In the title compound, C₃₄H₃₅NO₄, the dihedral angle between the pyridine ring and attached benzene ring is 79.17 (8)°. The meth­oxy­eth­oxy–eth­oxy side chain is disordered over two orientations in a 0.732 (7):0.268 (7) ratio. In the crystal, very weak C—H...N and C—H...O inter­actions link the mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.051
• wR factor = 0.150
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.6 Ratio
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C31 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H27      ..N1       .       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H29C     ..O4       .       2.69 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.097 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         11 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          2 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        13% Note
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O4A            107.8 Degree
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         54 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        502 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
   6 ALERT level G = General information/check it is not something unexpected

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

---

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

7-{3-Ethoxy-4-[2-(2-methoxyethoxy)ethoxy]phenyl}-5,6,8,9-tetrahydrodibenzo[c,h]acridine

Crystal data

C34H35NO4	F(000) = 1112
Mr = 521.63	Dx = 1.216 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.1797 (13) Å	Cell parameters from 7039 reflections
b = 30.203 (4) Å	θ = 2.4–23.8°
c = 11.0131 (16) Å	µ = 0.08 mm^−1
β = 111.056 (2)°	T = 296 K
V = 2849.6 (7) Å^3	Block, colourless
Z = 4	0.12 × 0.11 × 0.1 mm

Data collection

Bruker APEXII CCD area detector diffractometer	4199 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
phi and ω scans	θmax = 27.4°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.538, Tmax = 0.746	k = −38→38
22024 measured reflections	l = −14→13
5934 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.0721P)^2 + 0.4744P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
5934 reflections	Δρmax = 0.19 e Å^−3
401 parameters	Δρmin = −0.21 e Å^−3
54 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	Occ. (<1)
O1	0.71434 (16)	0.39493 (4)	0.20577 (13)	0.0743 (4)
O2	0.63910 (14)	0.42204 (4)	0.39754 (11)	0.0635 (3)
O3	0.6825 (5)	0.47955 (14)	0.6935 (4)	0.0755 (11)	0.732 (7)
O3A	0.695 (2)	0.4900 (6)	0.6688 (17)	0.173 (8)	0.268 (7)
O4	0.7326 (5)	0.49775 (11)	0.9670 (3)	0.1180 (16)	0.732 (7)
O4A	0.8197 (10)	0.5302 (3)	0.9932 (7)	0.119 (4)	0.268 (7)
N1	0.10451 (15)	0.22075 (4)	−0.09581 (13)	0.0510 (3)
C1	0.08312 (18)	0.26320 (5)	−0.13215 (15)	0.0485 (4)
C2	−0.03102 (18)	0.27262 (5)	−0.26405 (15)	0.0509 (4)
C3	−0.0832 (2)	0.23947 (6)	−0.35734 (17)	0.0633 (5)
H3	−0.047216	0.210658	−0.336395	0.076*
C4	−0.1871 (2)	0.24872 (7)	−0.48007 (19)	0.0749 (6)
H4	−0.222315	0.226179	−0.541210	0.090*
C5	−0.2390 (2)	0.29134 (7)	−0.5123 (2)	0.0754 (6)
H5	−0.308762	0.297781	−0.595388	0.090*
C6	−0.1874 (2)	0.32435 (7)	−0.42118 (19)	0.0692 (5)
H6	−0.222341	0.353155	−0.443849	0.083*
C7	−0.08478 (19)	0.31579 (6)	−0.29667 (16)	0.0563 (4)
C8	−0.0320 (2)	0.35105 (6)	−0.19438 (19)	0.0708 (5)
H8A	−0.099077	0.350812	−0.143513	0.085*
H8B	−0.042310	0.379743	−0.236200	0.085*
C9	0.1352 (2)	0.34464 (5)	−0.10467 (17)	0.0605 (4)
H9A	0.204076	0.351483	−0.151368	0.073*
H9B	0.158504	0.365084	−0.032218	0.073*
C10	0.16608 (18)	0.29796 (5)	−0.05304 (15)	0.0491 (4)
C11	0.27751 (18)	0.28769 (5)	0.06836 (15)	0.0504 (4)
C12	0.30031 (19)	0.24333 (5)	0.10727 (15)	0.0518 (4)
C13	0.4164 (2)	0.22877 (6)	0.23686 (18)	0.0672 (5)
H13A	0.364811	0.226732	0.299653	0.081*
H13B	0.498975	0.250599	0.268064	0.081*
C14	0.4863 (2)	0.18407 (7)	0.2251 (2)	0.0758 (6)
H14A	0.553373	0.187471	0.174858	0.091*
H14B	0.550046	0.173689	0.311146	0.091*
C15	0.3636 (2)	0.15035 (6)	0.16108 (17)	0.0638 (5)
C16	0.3808 (3)	0.10565 (7)	0.1952 (2)	0.0820 (6)
H16	0.470504	0.096199	0.261970	0.098*
C17	0.2674 (4)	0.07543 (7)	0.1317 (2)	0.0920 (8)
H17	0.281080	0.045700	0.155037	0.110*
C18	0.1336 (3)	0.08896 (7)	0.0336 (2)	0.0856 (7)
H18	0.056637	0.068414	−0.008815	0.103*
C19	0.1130 (2)	0.13319 (6)	−0.00238 (19)	0.0674 (5)
H19	0.022252	0.142257	−0.068636	0.081*
C20	0.2281 (2)	0.16406 (5)	0.06058 (16)	0.0559 (4)
C21	0.20972 (18)	0.21123 (5)	0.02191 (15)	0.0502 (4)
C22	0.37005 (19)	0.32369 (5)	0.15619 (15)	0.0512 (4)
C23	0.4972 (2)	0.34257 (6)	0.13558 (16)	0.0556 (4)
H23	0.523515	0.333000	0.065869	0.067*
C24	0.58527 (19)	0.37532 (5)	0.21675 (16)	0.0532 (4)
C25	0.54418 (19)	0.39013 (5)	0.32045 (15)	0.0512 (4)
C26	0.4170 (2)	0.37195 (6)	0.33955 (16)	0.0580 (4)
H26	0.388129	0.382072	0.407437	0.070*
C27	0.3310 (2)	0.33861 (6)	0.25851 (16)	0.0575 (4)
H27	0.246238	0.326250	0.273544	0.069*
C28	0.7627 (2)	0.38215 (8)	0.1035 (2)	0.0782 (6)
H28A	0.685289	0.390937	0.020748	0.094*
H28B	0.774643	0.350245	0.103402	0.094*
C29	0.9141 (3)	0.40407 (9)	0.1224 (2)	0.0933 (7)
H29A	0.943418	0.398295	0.048609	0.140*
H29B	0.992816	0.392671	0.199593	0.140*
H29C	0.903879	0.435423	0.131365	0.140*
C30	0.6000 (2)	0.43698 (7)	0.50509 (18)	0.0688 (5)
H30A	0.588985	0.411929	0.556253	0.083*
H30B	0.501933	0.453036	0.474177	0.083*
C31	0.7281 (3)	0.46647 (7)	0.58576 (19)	0.0746 (5)
H31A	0.826874	0.450774	0.616634	0.090*	0.732 (7)
H31B	0.737913	0.492118	0.536238	0.090*	0.732 (7)
H31C	0.818457	0.448388	0.631757	0.090*	0.268 (7)
H31D	0.756965	0.486084	0.528369	0.090*	0.268 (7)
C32	0.7863 (7)	0.50939 (18)	0.7776 (6)	0.0878 (14)	0.732 (7)
H32A	0.803993	0.533688	0.726962	0.105*	0.732 (7)
H32B	0.885443	0.494623	0.820207	0.105*	0.732 (7)
C32A	0.790 (4)	0.4894 (10)	0.783 (2)	0.176 (11)	0.268 (7)
H32C	0.879303	0.507911	0.790106	0.211*	0.268 (7)
H32D	0.826563	0.459474	0.807728	0.211*	0.268 (7)
C33	0.7328 (8)	0.52691 (19)	0.8746 (6)	0.0969 (16)	0.732 (7)
H33A	0.798537	0.551803	0.916278	0.116*	0.732 (7)
H33B	0.627543	0.538043	0.832187	0.116*	0.732 (7)
C33A	0.697 (3)	0.5091 (6)	0.8795 (19)	0.123 (6)	0.268 (7)
H33C	0.617954	0.530617	0.833003	0.148*	0.268 (7)
H33D	0.646248	0.485121	0.908089	0.148*	0.268 (7)
C34	0.7022 (11)	0.5171 (3)	1.0730 (7)	0.156 (3)	0.732 (7)
H34A	0.611157	0.535544	1.040400	0.233*	0.732 (7)
H34B	0.790132	0.534744	1.123588	0.233*	0.732 (7)
H34C	0.684890	0.494192	1.126604	0.233*	0.732 (7)
C34A	0.752 (3)	0.5412 (6)	1.0832 (17)	0.138 (7)	0.268 (7)
H34D	0.781137	0.519691	1.152001	0.207*	0.268 (7)
H34E	0.640465	0.541513	1.041264	0.207*	0.268 (7)
H34F	0.787465	0.569941	1.118587	0.207*	0.268 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0755 (9)	0.0878 (9)	0.0700 (8)	−0.0311 (7)	0.0387 (7)	−0.0266 (7)
O2	0.0689 (8)	0.0666 (7)	0.0561 (7)	−0.0144 (6)	0.0239 (6)	−0.0193 (6)
O3	0.0841 (19)	0.0845 (17)	0.061 (2)	−0.0294 (16)	0.0303 (17)	−0.0267 (13)
O3A	0.212 (15)	0.171 (13)	0.089 (7)	0.098 (10)	−0.004 (7)	−0.065 (8)
O4	0.177 (4)	0.103 (2)	0.085 (2)	0.020 (2)	0.061 (2)	−0.0026 (17)
O4A	0.139 (7)	0.143 (8)	0.080 (5)	−0.042 (5)	0.045 (4)	−0.031 (4)
N1	0.0477 (7)	0.0540 (8)	0.0490 (8)	−0.0020 (6)	0.0145 (6)	−0.0028 (6)
C1	0.0430 (8)	0.0529 (9)	0.0479 (9)	−0.0019 (7)	0.0144 (7)	−0.0030 (7)
C2	0.0416 (8)	0.0586 (9)	0.0484 (9)	−0.0029 (7)	0.0114 (7)	−0.0020 (7)
C3	0.0562 (10)	0.0633 (10)	0.0580 (11)	−0.0026 (8)	0.0057 (9)	−0.0061 (8)
C4	0.0663 (12)	0.0814 (13)	0.0590 (12)	−0.0065 (10)	0.0006 (10)	−0.0115 (10)
C5	0.0631 (12)	0.0880 (14)	0.0553 (11)	−0.0015 (10)	−0.0025 (9)	0.0048 (10)
C6	0.0603 (11)	0.0702 (11)	0.0639 (12)	0.0052 (9)	0.0065 (9)	0.0074 (9)
C7	0.0489 (9)	0.0625 (10)	0.0533 (10)	0.0015 (7)	0.0133 (8)	0.0006 (8)
C8	0.0764 (13)	0.0598 (10)	0.0646 (12)	0.0092 (9)	0.0112 (10)	−0.0032 (8)
C9	0.0667 (11)	0.0550 (9)	0.0542 (10)	−0.0060 (8)	0.0149 (9)	−0.0042 (7)
C10	0.0461 (9)	0.0546 (9)	0.0458 (9)	−0.0034 (7)	0.0155 (7)	−0.0036 (7)
C11	0.0442 (9)	0.0603 (9)	0.0459 (9)	−0.0062 (7)	0.0152 (7)	−0.0059 (7)
C12	0.0464 (9)	0.0617 (10)	0.0453 (9)	−0.0011 (7)	0.0140 (7)	−0.0010 (7)
C13	0.0639 (11)	0.0733 (11)	0.0524 (10)	0.0006 (9)	0.0065 (9)	0.0021 (8)
C14	0.0665 (12)	0.0902 (14)	0.0617 (12)	0.0174 (10)	0.0121 (10)	0.0117 (10)
C15	0.0763 (12)	0.0697 (11)	0.0507 (10)	0.0180 (9)	0.0293 (9)	0.0071 (8)
C16	0.1162 (18)	0.0777 (14)	0.0589 (12)	0.0320 (13)	0.0396 (12)	0.0154 (10)
C17	0.155 (2)	0.0610 (12)	0.0754 (14)	0.0155 (14)	0.0597 (16)	0.0114 (11)
C18	0.123 (2)	0.0607 (11)	0.0880 (16)	−0.0111 (12)	0.0561 (15)	−0.0023 (11)
C19	0.0811 (13)	0.0600 (10)	0.0682 (12)	−0.0038 (9)	0.0355 (10)	−0.0017 (9)
C20	0.0655 (11)	0.0565 (9)	0.0527 (9)	0.0047 (8)	0.0295 (9)	0.0014 (7)
C21	0.0461 (9)	0.0572 (9)	0.0476 (9)	0.0000 (7)	0.0171 (7)	−0.0010 (7)
C22	0.0479 (9)	0.0588 (9)	0.0428 (8)	−0.0044 (7)	0.0113 (7)	−0.0033 (7)
C23	0.0557 (10)	0.0670 (10)	0.0460 (9)	−0.0088 (8)	0.0204 (8)	−0.0108 (7)
C24	0.0502 (9)	0.0605 (9)	0.0490 (9)	−0.0092 (7)	0.0180 (7)	−0.0056 (7)
C25	0.0518 (9)	0.0542 (9)	0.0434 (8)	−0.0032 (7)	0.0120 (7)	−0.0057 (7)
C26	0.0572 (10)	0.0709 (10)	0.0487 (9)	−0.0030 (8)	0.0225 (8)	−0.0087 (8)
C27	0.0509 (10)	0.0715 (11)	0.0512 (10)	−0.0092 (8)	0.0199 (8)	−0.0059 (8)
C28	0.0731 (13)	0.0934 (14)	0.0782 (13)	−0.0149 (11)	0.0395 (11)	−0.0201 (11)
C29	0.0768 (14)	0.1173 (18)	0.0985 (17)	−0.0265 (13)	0.0469 (13)	−0.0220 (14)
C30	0.0715 (12)	0.0710 (11)	0.0622 (11)	−0.0002 (9)	0.0219 (10)	−0.0207 (9)
C31	0.0886 (14)	0.0694 (11)	0.0621 (12)	−0.0079 (10)	0.0225 (11)	−0.0175 (9)
C32	0.097 (3)	0.093 (3)	0.072 (2)	−0.032 (2)	0.029 (2)	−0.040 (2)
C32A	0.224 (19)	0.22 (3)	0.062 (7)	0.017 (19)	0.030 (9)	−0.023 (13)
C33	0.132 (4)	0.088 (4)	0.069 (3)	−0.017 (3)	0.034 (2)	−0.024 (2)
C33A	0.184 (15)	0.096 (12)	0.068 (8)	−0.023 (10)	0.019 (8)	−0.010 (8)
C34	0.215 (8)	0.166 (6)	0.122 (4)	0.000 (6)	0.105 (5)	−0.032 (5)
C34A	0.23 (2)	0.118 (12)	0.100 (9)	−0.051 (12)	0.103 (11)	−0.037 (9)

Geometric parameters (Å, º)

O1—C24	1.368 (2)	C16—C17	1.373 (3)
O1—C28	1.405 (2)	C17—H17	0.9300
O2—C25	1.3701 (19)	C17—C18	1.375 (4)
O2—C30	1.429 (2)	C18—H18	0.9300
O3—C31	1.448 (4)	C18—C19	1.387 (3)
O3—C32	1.394 (6)	C19—H19	0.9300
O3A—C31	1.278 (14)	C19—C20	1.393 (3)
O3A—C32A	1.24 (3)	C20—C21	1.479 (2)
O4—C33	1.346 (8)	C22—C23	1.389 (2)
O4—C34	1.420 (6)	C22—C27	1.375 (2)
O4A—C33A	1.50 (2)	C23—H23	0.9300
O4A—C34A	1.386 (18)	C23—C24	1.383 (2)
N1—C1	1.336 (2)	C24—C25	1.399 (2)
N1—C21	1.340 (2)	C25—C26	1.373 (2)
C1—C2	1.482 (2)	C26—H26	0.9300
C1—C10	1.402 (2)	C26—C27	1.388 (2)
C2—C3	1.391 (2)	C27—H27	0.9300
C2—C7	1.395 (2)	C28—H28A	0.9700
C3—H3	0.9300	C28—H28B	0.9700
C3—C4	1.374 (3)	C28—C29	1.485 (3)
C4—H4	0.9300	C29—H29A	0.9600
C4—C5	1.374 (3)	C29—H29B	0.9600
C5—H5	0.9300	C29—H29C	0.9600
C5—C6	1.372 (3)	C30—H30A	0.9700
C6—H6	0.9300	C30—H30B	0.9700
C6—C7	1.381 (2)	C30—C31	1.488 (3)
C7—C8	1.499 (2)	C31—H31A	0.9700
C8—H8A	0.9700	C31—H31B	0.9700
C8—H8B	0.9700	C31—H31C	0.9700
C8—C9	1.510 (3)	C31—H31D	0.9700
C9—H9A	0.9700	C32—H32A	0.9700
C9—H9B	0.9700	C32—H32B	0.9700
C9—C10	1.508 (2)	C32—C33	1.428 (9)
C10—C11	1.396 (2)	C32A—H32C	0.9700
C11—C12	1.399 (2)	C32A—H32D	0.9700
C11—C22	1.500 (2)	C32A—C33A	1.70 (3)
C12—C13	1.508 (2)	C33—H33A	0.9700
C12—C21	1.398 (2)	C33—H33B	0.9700
C13—H13A	0.9700	C33A—H33C	0.9700
C13—H13B	0.9700	C33A—H33D	0.9700
C13—C14	1.520 (3)	C34—H34A	0.9600
C14—H14A	0.9700	C34—H34B	0.9600
C14—H14B	0.9700	C34—H34C	0.9600
C14—C15	1.494 (3)	C34A—H34D	0.9600
C15—C16	1.395 (3)	C34A—H34E	0.9600
C15—C20	1.398 (3)	C34A—H34F	0.9600
C16—H16	0.9300
C24—O1—C28	119.02 (14)	C27—C22—C11	120.80 (15)
C25—O2—C30	116.26 (14)	C27—C22—C23	118.75 (15)
C32—O3—C31	113.0 (3)	C22—C23—H23	119.4
C32A—O3A—C31	116.7 (19)	C24—C23—C22	121.25 (15)
C33—O4—C34	113.9 (4)	C24—C23—H23	119.4
C34A—O4A—C33A	107.6 (14)	O1—C24—C23	125.20 (15)
C1—N1—C21	118.22 (13)	O1—C24—C25	115.46 (14)
N1—C1—C2	117.00 (14)	C23—C24—C25	119.33 (15)
N1—C1—C10	122.95 (14)	O2—C25—C24	115.65 (14)
C10—C1—C2	120.02 (14)	O2—C25—C26	124.95 (15)
C3—C2—C1	121.36 (15)	C26—C25—C24	119.39 (14)
C3—C2—C7	119.13 (15)	C25—C26—H26	119.7
C7—C2—C1	119.49 (14)	C25—C26—C27	120.65 (15)
C2—C3—H3	119.6	C27—C26—H26	119.7
C4—C3—C2	120.89 (17)	C22—C27—C26	120.61 (15)
C4—C3—H3	119.6	C22—C27—H27	119.7
C3—C4—H4	120.1	C26—C27—H27	119.7
C5—C4—C3	119.86 (18)	O1—C28—H28A	110.0
C5—C4—H4	120.1	O1—C28—H28B	110.0
C4—C5—H5	120.2	O1—C28—C29	108.33 (17)
C6—C5—C4	119.70 (18)	H28A—C28—H28B	108.4
C6—C5—H5	120.2	C29—C28—H28A	110.0
C5—C6—H6	119.2	C29—C28—H28B	110.0
C5—C6—C7	121.54 (18)	C28—C29—H29A	109.5
C7—C6—H6	119.2	C28—C29—H29B	109.5
C2—C7—C8	118.81 (15)	C28—C29—H29C	109.5
C6—C7—C2	118.87 (16)	H29A—C29—H29B	109.5
C6—C7—C8	122.31 (16)	H29A—C29—H29C	109.5
C7—C8—H8A	109.2	H29B—C29—H29C	109.5
C7—C8—H8B	109.2	O2—C30—H30A	110.2
C7—C8—C9	112.27 (15)	O2—C30—H30B	110.2
H8A—C8—H8B	107.9	O2—C30—C31	107.68 (16)
C9—C8—H8A	109.2	H30A—C30—H30B	108.5
C9—C8—H8B	109.1	C31—C30—H30A	110.2
C8—C9—H9A	109.2	C31—C30—H30B	110.2
C8—C9—H9B	109.2	O3—C31—C30	104.7 (2)
H9A—C9—H9B	107.9	O3—C31—H31A	110.8
C10—C9—C8	112.07 (14)	O3—C31—H31B	110.8
C10—C9—H9A	109.2	O3A—C31—C30	114.7 (9)
C10—C9—H9B	109.2	O3A—C31—H31C	108.6
C1—C10—C9	118.64 (14)	O3A—C31—H31D	108.6
C11—C10—C1	118.45 (15)	C30—C31—H31A	110.8
C11—C10—C9	122.87 (14)	C30—C31—H31B	110.8
C10—C11—C12	118.93 (14)	C30—C31—H31C	108.6
C10—C11—C22	120.48 (14)	C30—C31—H31D	108.6
C12—C11—C22	120.59 (14)	H31A—C31—H31B	108.9
C11—C12—C13	123.11 (15)	H31C—C31—H31D	107.6
C21—C12—C11	118.08 (14)	O3—C32—H32A	108.9
C21—C12—C13	118.80 (15)	O3—C32—H32B	108.9
C12—C13—H13A	109.5	O3—C32—C33	113.6 (5)
C12—C13—H13B	109.5	H32A—C32—H32B	107.7
C12—C13—C14	110.77 (15)	C33—C32—H32A	108.9
H13A—C13—H13B	108.1	C33—C32—H32B	108.9
C14—C13—H13A	109.5	O3A—C32A—H32C	110.3
C14—C13—H13B	109.5	O3A—C32A—H32D	110.3
C13—C14—H14A	109.2	O3A—C32A—C33A	107 (2)
C13—C14—H14B	109.2	H32C—C32A—H32D	108.5
H14A—C14—H14B	107.9	C33A—C32A—H32C	110.3
C15—C14—C13	112.08 (16)	C33A—C32A—H32D	110.3
C15—C14—H14A	109.2	O4—C33—C32	114.7 (5)
C15—C14—H14B	109.2	O4—C33—H33A	108.6
C16—C15—C14	122.63 (19)	O4—C33—H33B	108.6
C16—C15—C20	118.9 (2)	C32—C33—H33A	108.6
C20—C15—C14	118.49 (16)	C32—C33—H33B	108.6
C15—C16—H16	119.5	H33A—C33—H33B	107.6
C17—C16—C15	121.0 (2)	O4A—C33A—C32A	106.0 (18)
C17—C16—H16	119.5	O4A—C33A—H33C	110.5
C16—C17—H17	119.9	O4A—C33A—H33D	110.5
C16—C17—C18	120.2 (2)	C32A—C33A—H33C	110.5
C18—C17—H17	119.9	C32A—C33A—H33D	110.5
C17—C18—H18	119.9	H33C—C33A—H33D	108.7
C17—C18—C19	120.2 (2)	O4—C34—H34A	109.5
C19—C18—H18	119.9	O4—C34—H34B	109.5
C18—C19—H19	119.9	O4—C34—H34C	109.5
C18—C19—C20	120.1 (2)	H34A—C34—H34B	109.5
C20—C19—H19	119.9	H34A—C34—H34C	109.5
C15—C20—C21	119.37 (16)	H34B—C34—H34C	109.5
C19—C20—C15	119.72 (17)	O4A—C34A—H34D	109.5
C19—C20—C21	120.91 (16)	O4A—C34A—H34E	109.5
N1—C21—C12	123.34 (15)	O4A—C34A—H34F	109.5
N1—C21—C20	116.95 (14)	H34D—C34A—H34E	109.5
C12—C21—C20	119.71 (15)	H34D—C34A—H34F	109.5
C23—C22—C11	120.45 (14)	H34E—C34A—H34F	109.5
O1—C24—C25—O2	−0.4 (2)	C12—C11—C22—C27	−78.8 (2)
O1—C24—C25—C26	−179.39 (15)	C12—C13—C14—C15	−51.7 (2)
O2—C25—C26—C27	−177.74 (16)	C13—C12—C21—N1	−179.38 (16)
O2—C30—C31—O3	−178.9 (3)	C13—C12—C21—C20	0.6 (2)
O2—C30—C31—O3A	165.3 (10)	C13—C14—C15—C16	−145.65 (18)
O3—C32—C33—O4	70.8 (8)	C13—C14—C15—C20	36.2 (2)
O3A—C32A—C33A—O4A	−151 (3)	C14—C15—C16—C17	−178.1 (2)
N1—C1—C2—C3	−16.0 (2)	C14—C15—C20—C19	178.86 (17)
N1—C1—C2—C7	165.48 (15)	C14—C15—C20—C21	−0.7 (2)
N1—C1—C10—C9	178.78 (15)	C15—C16—C17—C18	−0.6 (3)
N1—C1—C10—C11	0.9 (2)	C15—C20—C21—N1	160.90 (15)
C1—N1—C21—C12	−1.4 (2)	C15—C20—C21—C12	−19.1 (2)
C1—N1—C21—C20	178.62 (14)	C16—C15—C20—C19	0.6 (3)
C1—C2—C3—C4	−178.93 (18)	C16—C15—C20—C21	−178.91 (16)
C1—C2—C7—C6	178.00 (16)	C16—C17—C18—C19	0.5 (3)
C1—C2—C7—C8	−3.4 (2)	C17—C18—C19—C20	0.2 (3)
C1—C10—C11—C12	−1.0 (2)	C18—C19—C20—C15	−0.7 (3)
C1—C10—C11—C22	179.60 (14)	C18—C19—C20—C21	178.80 (17)
C2—C1—C10—C9	0.6 (2)	C19—C20—C21—N1	−18.6 (2)
C2—C1—C10—C11	−177.26 (14)	C19—C20—C21—C12	161.38 (16)
C2—C3—C4—C5	0.9 (3)	C20—C15—C16—C17	0.0 (3)
C2—C7—C8—C9	36.3 (2)	C21—N1—C1—C2	178.51 (14)
C3—C2—C7—C6	−0.5 (3)	C21—N1—C1—C10	0.3 (2)
C3—C2—C7—C8	178.09 (17)	C21—C12—C13—C14	34.3 (2)
C3—C4—C5—C6	−0.5 (3)	C22—C11—C12—C13	0.0 (2)
C4—C5—C6—C7	−0.5 (3)	C22—C11—C12—C21	179.41 (14)
C5—C6—C7—C2	1.0 (3)	C22—C23—C24—O1	178.26 (16)
C5—C6—C7—C8	−177.6 (2)	C22—C23—C24—C25	−0.9 (3)
C6—C7—C8—C9	−145.14 (18)	C23—C22—C27—C26	0.1 (3)
C7—C2—C3—C4	−0.4 (3)	C23—C24—C25—O2	178.85 (15)
C7—C8—C9—C10	−49.5 (2)	C23—C24—C25—C26	−0.1 (3)
C8—C9—C10—C1	32.2 (2)	C24—O1—C28—C29	−173.35 (18)
C8—C9—C10—C11	−150.05 (16)	C24—C25—C26—C27	1.1 (3)
C9—C10—C11—C12	−178.80 (15)	C25—O2—C30—C31	172.29 (15)
C9—C10—C11—C22	1.8 (2)	C25—C26—C27—C22	−1.1 (3)
C10—C1—C2—C3	162.25 (16)	C27—C22—C23—C24	0.9 (3)
C10—C1—C2—C7	−16.2 (2)	C28—O1—C24—C23	1.3 (3)
C10—C11—C12—C13	−179.33 (16)	C28—O1—C24—C25	−179.51 (17)
C10—C11—C12—C21	0.0 (2)	C30—O2—C25—C24	−179.04 (15)
C10—C11—C22—C23	−79.5 (2)	C30—O2—C25—C26	−0.1 (2)
C10—C11—C22—C27	100.53 (19)	C31—O3—C32—C33	172.4 (5)
C11—C12—C13—C14	−146.32 (18)	C31—O3A—C32A—C33A	−162.8 (15)
C11—C12—C21—N1	1.2 (2)	C32—O3—C31—C30	−177.1 (4)
C11—C12—C21—C20	−178.78 (14)	C32A—O3A—C31—C30	130 (2)
C11—C22—C23—C24	−179.01 (15)	C34—O4—C33—C32	170.9 (6)
C11—C22—C27—C26	−179.98 (16)	C34A—O4A—C33A—C32A	−171.9 (15)
C12—C11—C22—C23	101.14 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···N1^i	0.93	2.67	3.537 (2)	156
C29—H29c···O4^ii	0.96	2.69	3.415 (6)	132

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