The structure of 9-(3-bromo-6-chloro-2-hy­droxy­phen­yl)-10-(2-hy­droxy­ethyl)-3,6-diphenyl-3,4,5,6,7,9-hexa­hydro-2H-acridine-1,8-dione

The structure of a deca­ahydro­acridine derivative with phenyl substituents at the 3- and 5-positions of the cyclo­hexenone rings is reported. An extensive range of O—H...O, C—H...O hydrogen bonds augmented by C—H...π(ring) hydrogen bonds an O...Br halogen bond and an unusual Br...π(ring) contact stabilizes the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.040
• wR factor = 0.101
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for   C61      --C66       .       12.0 s.u.
PLAT410_ALERT_2_B Short Intra H...H Contact  H15A     ..H5C              1.87 Ang.
                                                      x,y,z  =      1_555 Check
PLAT410_ALERT_2_B Short Intra H...H Contact  H15B     ..H4D              1.89 Ang.
                                                      x,y,z  =      1_555 Check
PLAT410_ALERT_2_B Short Intra H...H Contact  H32      ..H3B              1.86 Ang.
                                                      x,y,z  =      1_555 Check

Alert level C
PLAT213_ALERT_2_C Atom C31             has ADP max/min Ratio .....        3.2 prolat
PLAT220_ALERT_2_C Non-Solvent  Resd 1  C   Ueq(max)/Ueq(min) Range        3.7 Ratio
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         C7 Check
PLAT410_ALERT_2_C Short Intra H...H Contact  H4A      ..H15B             1.93 Ang.
                                                      x,y,z  =      1_555 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15A     ..O16              2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A      ..O8               2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A      ..O2'              2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H34      ..CL5'             2.87 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.361 Check
PLAT977_ALERT_2_C Check Negative Difference Density on H2A1             -0.37 eA-3
PLAT977_ALERT_2_C Check Negative Difference Density on H7A              -0.40 eA-3

Alert level G
PLAT164_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct.          2 Note
PLAT230_ALERT_2_G Hirshfeld Test Diff for   C6A      --C7        .        7.5 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         8% Note
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          5 Note
PLAT793_ALERT_4_G Model has Chirality at C9          (Centro SPGR)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         48 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  13 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
   8 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) and TITAN (Hunter & Simpson, 1999); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), enCIFer (Allen et al., 2004), PLATON (Spek, 2009), publCIF (Westrip 2010) and WinGX (Farrugia 2012).

9-(3-Bromo-6-chloro-2-hydroxyphenyl)-10-(2-hydroxyethyl)-3,6-diphenyl-3,4,5,6,7,9-hexahydro-2H-acridine-1,8-dione

Crystal data

C33H29BrClNO4	F(000) = 1272
Mr = 618.93	Dx = 1.416 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 14.5669 (2) Å	Cell parameters from 16242 reflections
b = 15.4643 (2) Å	θ = 4.2–76.6°
c = 13.4979 (2) Å	µ = 3.09 mm^−1
β = 107.280 (1)°	T = 100 K
V = 2903.39 (7) Å^3	Rectangular plate, pale yellow
Z = 4	0.37 × 0.14 × 0.12 mm

Data collection

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer	6076 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	5714 reflections with I > 2σ(I)
Detector resolution: 5.1725 pixels mm^-1	Rint = 0.045
ω scans	θmax = 76.7°, θmin = 4.3°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −18→18
Tmin = 0.618, Tmax = 1.000	k = −19→14
23967 measured reflections	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0434P)^2 + 3.2091P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
6076 reflections	Δρmax = 0.66 e Å^−3
402 parameters	Δρmin = −0.57 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.

Refinement. One reflection with Fo >>> Fc was omitted from the final refinement cycles.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.75525 (13)	0.16790 (13)	0.44418 (13)	0.0361 (4)
C1	0.75604 (17)	0.20511 (17)	0.36498 (18)	0.0309 (5)
C2A	0.8507 (4)	0.2118 (5)	0.3297 (4)	0.0302 (15)	0.521 (10)
H2A1	0.9018	0.2366	0.3886	0.036*	0.521 (10)
H2A2	0.8706	0.1521	0.3196	0.036*	0.521 (10)
C3A	0.8503 (3)	0.2523 (4)	0.2536 (4)	0.0197 (12)	0.521 (10)
H3A	0.8850	0.3059	0.2857	0.024*	0.521 (10)
C2B	0.8203 (4)	0.1718 (4)	0.3031 (5)	0.0198 (12)	0.479 (10)
H2B1	0.8869	0.1711	0.3503	0.024*	0.479 (10)
H2B2	0.8021	0.1109	0.2847	0.024*	0.479 (10)
C3B	0.8224 (4)	0.2130 (4)	0.2140 (5)	0.0240 (15)	0.479 (10)
H3B	0.7874	0.1693	0.1618	0.029*	0.479 (10)
C31	0.9137 (2)	0.2237 (2)	0.1795 (3)	0.0519 (9)
C32	0.9205 (2)	0.1493 (2)	0.1268 (3)	0.0525 (9)
H32	0.8802	0.1016	0.1290	0.063*
C33	0.9860 (3)	0.1432 (2)	0.0700 (3)	0.0552 (8)
H33	0.9902	0.0916	0.0334	0.066*
C34	1.0447 (2)	0.2126 (2)	0.0674 (3)	0.0573 (9)
H34	1.0896	0.2086	0.0289	0.069*
C35	1.0389 (2)	0.2863 (2)	0.1194 (3)	0.0546 (9)
H35	1.0792	0.3341	0.1170	0.065*
C36	0.9734 (2)	0.2917 (2)	0.1762 (3)	0.0499 (8)
H36A	0.9700	0.3432	0.2132	0.060*	0.521 (10)
H36B	0.9700	0.3432	0.2132	0.060*	0.479 (10)
C4	0.75926 (14)	0.29215 (14)	0.17397 (16)	0.0201 (4)
H4A	0.7760	0.3489	0.1500	0.024*	0.521 (10)
H4B	0.7374	0.2537	0.1128	0.024*	0.521 (10)
H4C	0.8002	0.3445	0.1879	0.024*	0.479 (10)
H4D	0.7311	0.2870	0.0978	0.024*	0.479 (10)
C5	0.42495 (14)	0.37594 (13)	0.10511 (15)	0.0178 (4)
H5A	0.4165	0.3450	0.0388	0.021*	0.746 (9)
H5B	0.4335	0.4381	0.0929	0.021*	0.746 (9)
H5C	0.433 (7)	0.370 (7)	0.025 (8)	0.021*	0.254 (9)
H5D	0.422 (8)	0.437 (7)	0.117 (8)	0.021*	0.254 (9)
C6A	0.33431 (18)	0.3641 (2)	0.1396 (2)	0.0195 (9)	0.746 (9)
H6A	0.3356	0.4086	0.1938	0.023*	0.746 (9)
C6B	0.3349 (5)	0.3168 (5)	0.0936 (6)	0.015 (2)	0.254 (9)
H6B	0.3341	0.2706	0.0415	0.019*	0.254 (9)
C61	0.24605 (17)	0.3823 (2)	0.0451 (2)	0.0420 (7)
C62	0.20200 (18)	0.4592 (2)	0.0484 (2)	0.0396 (6)
H62	0.2246	0.4951	0.1078	0.047*
C63	0.12511 (18)	0.48598 (19)	−0.0327 (2)	0.0359 (5)
H63	0.0953	0.5399	−0.0281	0.043*
C64	0.09078 (17)	0.43614 (17)	−0.1202 (2)	0.0347 (6)
H64	0.0377	0.4554	−0.1757	0.042*
C65	0.13441 (19)	0.35737 (19)	−0.1267 (2)	0.0406 (6)
H65	0.1118	0.3221	−0.1866	0.049*
C66	0.21263 (19)	0.33072 (19)	−0.0430 (3)	0.0483 (8)
H66A	0.2430	0.2770	−0.0466	0.058*	0.746 (9)
H66	0.2430	0.2770	−0.0466	0.058*	0.254 (9)
C7	0.33159 (18)	0.2777 (2)	0.1859 (2)	0.0424 (7)
H7A	0.3299	0.2323	0.1337	0.051*	0.746 (9)
H7B	0.2729	0.2722	0.2081	0.051*	0.746 (9)
H7C	0.3036	0.2195	0.1671	0.051*	0.254 (9)
H7D	0.2846	0.3109	0.2107	0.051*	0.254 (9)
C8	0.41893 (15)	0.26609 (14)	0.27755 (16)	0.0217 (4)
O8	0.41215 (11)	0.22515 (11)	0.35542 (12)	0.0253 (3)
C9	0.59971 (14)	0.28147 (13)	0.35948 (15)	0.0164 (4)
H9	0.5898	0.2278	0.3964	0.020*
C11	0.67923 (14)	0.26478 (13)	0.31174 (15)	0.0169 (4)
C12	0.67918 (13)	0.30368 (13)	0.22213 (15)	0.0165 (4)
C13	0.51346 (14)	0.34248 (12)	0.18453 (15)	0.0156 (4)
C14	0.50871 (14)	0.29899 (12)	0.27191 (15)	0.0162 (4)
N10	0.60071 (11)	0.35389 (11)	0.16665 (13)	0.0159 (3)
C15	0.61313 (14)	0.41375 (14)	0.08619 (15)	0.0186 (4)
H15A	0.5504	0.4225	0.0328	0.022*
H15B	0.6580	0.3879	0.0519	0.022*
C16	0.65185 (15)	0.49977 (14)	0.13240 (17)	0.0236 (4)
H16A	0.7049	0.4910	0.1973	0.028*
H16B	0.6770	0.5327	0.0832	0.028*
O16	0.57556 (13)	0.54592 (12)	0.15339 (15)	0.0336 (4)
H16O	0.592 (3)	0.598 (3)	0.156 (3)	0.050*
C1'	0.62288 (14)	0.35601 (13)	0.43787 (15)	0.0168 (4)
C2'	0.57556 (14)	0.36228 (13)	0.51490 (15)	0.0179 (4)
O2'	0.51146 (11)	0.30269 (10)	0.52679 (12)	0.0222 (3)
H2'O	0.485 (2)	0.274 (2)	0.472 (3)	0.033*
C3'	0.59615 (15)	0.43193 (14)	0.58369 (17)	0.0223 (4)
Br3'	0.53322 (2)	0.44056 (2)	0.68754 (2)	0.02632 (9)
C4'	0.66042 (17)	0.49627 (15)	0.57727 (18)	0.0278 (5)
H4'	0.6733	0.5436	0.6243	0.033*
C5'	0.70526 (16)	0.48948 (15)	0.50025 (19)	0.0275 (5)
Cl5'	0.78601 (5)	0.56959 (4)	0.48926 (6)	0.04541 (18)
C6'	0.68789 (15)	0.42062 (15)	0.43232 (17)	0.0227 (4)
H6'	0.7206	0.4172	0.3811	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0387 (9)	0.0496 (11)	0.0255 (8)	0.0246 (8)	0.0179 (7)	0.0171 (8)
C1	0.0314 (12)	0.0418 (14)	0.0240 (11)	0.0176 (10)	0.0152 (9)	0.0099 (10)
C2A	0.023 (2)	0.042 (4)	0.029 (3)	0.017 (3)	0.012 (2)	0.013 (3)
C3A	0.0135 (19)	0.023 (3)	0.024 (2)	0.0011 (18)	0.0071 (17)	0.003 (2)
C2B	0.016 (2)	0.017 (3)	0.030 (3)	0.006 (2)	0.012 (2)	0.007 (2)
C3B	0.018 (2)	0.030 (3)	0.027 (3)	0.006 (2)	0.010 (2)	0.003 (2)
C31	0.0293 (13)	0.075 (2)	0.0634 (19)	0.0323 (14)	0.0320 (13)	0.0481 (17)
C32	0.0248 (12)	0.069 (2)	0.065 (2)	0.0031 (13)	0.0155 (13)	0.0302 (17)
C33	0.0555 (19)	0.060 (2)	0.059 (2)	0.0050 (16)	0.0308 (16)	0.0077 (16)
C34	0.0530 (18)	0.061 (2)	0.080 (2)	0.0205 (16)	0.0544 (18)	0.0245 (18)
C35	0.0339 (14)	0.0482 (17)	0.095 (3)	0.0124 (13)	0.0398 (16)	0.0261 (17)
C36	0.0411 (15)	0.0537 (18)	0.065 (2)	0.0271 (14)	0.0314 (15)	0.0204 (15)
C4	0.0152 (9)	0.0253 (10)	0.0218 (9)	0.0037 (8)	0.0087 (7)	0.0042 (8)
C5	0.0143 (8)	0.0203 (10)	0.0206 (9)	0.0000 (7)	0.0080 (7)	0.0028 (8)
C6A	0.0144 (12)	0.0235 (17)	0.0212 (15)	−0.0021 (10)	0.0062 (10)	0.0004 (13)
C6B	0.012 (3)	0.018 (5)	0.014 (4)	−0.007 (3)	0.000 (3)	−0.003 (3)
C61	0.0148 (10)	0.0588 (18)	0.0492 (16)	−0.0086 (11)	0.0047 (10)	0.0285 (14)
C62	0.0242 (11)	0.0598 (18)	0.0315 (13)	−0.0115 (12)	0.0034 (10)	0.0088 (12)
C63	0.0263 (11)	0.0403 (14)	0.0400 (14)	−0.0004 (10)	0.0083 (10)	0.0025 (11)
C64	0.0193 (10)	0.0414 (14)	0.0371 (13)	−0.0018 (10)	−0.0013 (9)	0.0055 (11)
C65	0.0288 (12)	0.0386 (14)	0.0549 (17)	−0.0125 (11)	0.0134 (12)	−0.0066 (12)
C66	0.0269 (12)	0.0332 (14)	0.093 (2)	0.0073 (11)	0.0301 (15)	0.0277 (15)
C7	0.0212 (11)	0.0646 (19)	0.0358 (13)	−0.0164 (12)	−0.0001 (10)	0.0226 (13)
C8	0.0201 (9)	0.0249 (10)	0.0208 (10)	−0.0044 (8)	0.0074 (8)	0.0022 (8)
O8	0.0240 (7)	0.0309 (8)	0.0232 (7)	−0.0077 (6)	0.0103 (6)	0.0049 (6)
C9	0.0170 (9)	0.0177 (9)	0.0170 (9)	0.0011 (7)	0.0088 (7)	0.0015 (7)
C11	0.0151 (8)	0.0192 (9)	0.0174 (9)	0.0023 (7)	0.0065 (7)	−0.0006 (7)
C12	0.0130 (8)	0.0186 (9)	0.0187 (9)	0.0015 (7)	0.0058 (7)	0.0004 (7)
C13	0.0154 (8)	0.0148 (9)	0.0185 (9)	−0.0001 (7)	0.0081 (7)	−0.0020 (7)
C14	0.0155 (8)	0.0170 (9)	0.0179 (9)	0.0007 (7)	0.0077 (7)	0.0004 (7)
N10	0.0138 (7)	0.0189 (8)	0.0168 (8)	0.0013 (6)	0.0073 (6)	0.0028 (6)
C15	0.0157 (8)	0.0253 (10)	0.0171 (9)	0.0025 (8)	0.0086 (7)	0.0050 (8)
C16	0.0208 (9)	0.0250 (10)	0.0267 (10)	−0.0020 (8)	0.0095 (8)	0.0062 (8)
O16	0.0374 (9)	0.0255 (8)	0.0458 (10)	−0.0031 (7)	0.0247 (8)	−0.0060 (8)
C1'	0.0166 (8)	0.0179 (9)	0.0164 (9)	0.0027 (7)	0.0057 (7)	0.0008 (7)
C2'	0.0176 (9)	0.0191 (9)	0.0178 (9)	0.0036 (7)	0.0067 (7)	0.0025 (7)
O2'	0.0257 (7)	0.0235 (7)	0.0217 (7)	−0.0039 (6)	0.0135 (6)	−0.0014 (6)
C3'	0.0227 (10)	0.0237 (10)	0.0224 (10)	0.0037 (8)	0.0096 (8)	0.0000 (8)
Br3'	0.03193 (14)	0.02757 (14)	0.02364 (13)	0.00358 (9)	0.01467 (9)	−0.00484 (8)
C4'	0.0295 (11)	0.0245 (11)	0.0296 (11)	−0.0018 (9)	0.0093 (9)	−0.0075 (9)
C5'	0.0247 (10)	0.0250 (11)	0.0354 (12)	−0.0065 (9)	0.0131 (9)	−0.0031 (9)
Cl5'	0.0475 (4)	0.0350 (3)	0.0624 (4)	−0.0218 (3)	0.0296 (3)	−0.0141 (3)
C6'	0.0211 (9)	0.0255 (10)	0.0245 (10)	−0.0003 (8)	0.0110 (8)	−0.0004 (8)

Geometric parameters (Å, º)

O1—C1	1.217 (3)	C61—C66	1.394 (5)
C1—C11	1.464 (3)	C62—C63	1.377 (4)
C1—C2B	1.518 (5)	C62—H62	0.9500
C1—C2A	1.590 (6)	C63—C64	1.374 (4)
C2A—C3A	1.202 (7)	C63—H63	0.9500
C2A—H2A1	0.9900	C64—C65	1.389 (4)
C2A—H2A2	0.9900	C64—H64	0.9500
C3A—C4	1.564 (5)	C65—C66	1.407 (4)
C3A—C31	1.612 (5)	C65—H65	0.9500
C3A—H3A	1.0000	C66—H66A	0.9500
C2B—C3B	1.369 (7)	C66—H66	0.9500
C2B—H2B1	0.9900	C7—C8	1.499 (3)
C2B—H2B2	0.9900	C7—H7A	0.9900
C3B—C4	1.531 (5)	C7—H7B	0.9900
C3B—C31	1.543 (5)	C7—H7C	0.9900
C3B—H3B	1.0000	C7—H7D	0.9900
C31—C32	1.372 (6)	C8—O8	1.256 (3)
C31—C36	1.373 (5)	C8—C14	1.426 (3)
C32—C33	1.393 (4)	C9—C11	1.506 (2)
C32—H32	0.9500	C9—C14	1.516 (3)
C33—C34	1.379 (5)	C9—C1'	1.533 (3)
C33—H33	0.9500	C9—H9	1.0000
C34—C35	1.355 (5)	C11—C12	1.351 (3)
C34—H34	0.9500	C12—N10	1.401 (2)
C35—C36	1.393 (4)	C13—N10	1.374 (2)
C35—H35	0.9500	C13—C14	1.377 (3)
C36—H36A	0.9500	N10—C15	1.478 (2)
C36—H36B	0.9500	C15—C16	1.506 (3)
C4—C12	1.505 (3)	C15—H15A	0.9900
C4—H4A	0.9900	C15—H15B	0.9900
C4—H4B	0.9900	C16—O16	1.418 (3)
C4—H4C	0.9900	C16—H16A	0.9900
C4—H4D	0.9900	C16—H16B	0.9900
C5—C13	1.503 (3)	O16—Br3'^i	3.0308 (18)
C5—C6A	1.536 (3)	O16—H16O	0.84 (4)
C5—C6B	1.568 (7)	C1'—C6'	1.394 (3)
C5—H5A	0.9900	C1'—C2'	1.411 (3)
C5—H5B	0.9900	C2'—O2'	1.355 (3)
C5—H5C	1.12 (11)	C2'—C3'	1.395 (3)
C5—H5D	0.96 (10)	O2'—H2'O	0.85 (3)
C6A—C7	1.481 (4)	C3'—C4'	1.386 (3)
C6A—C61	1.544 (3)	C3'—Br3'	1.894 (2)
C6A—H6A	1.0000	C4'—C5'	1.386 (3)
C6B—C7	1.398 (8)	C4'—H4'	0.9500
C6B—C61	1.620 (8)	C5'—C6'	1.379 (3)
C6B—H6B	1.0000	C5'—Cl5'	1.745 (2)
C61—C62	1.358 (5)	C6'—H6'	0.9500
O1—C1—C11	121.6 (2)	C62—C61—C6B	149.5 (4)
O1—C1—C2B	119.4 (3)	C66—C61—C6B	91.3 (4)
C11—C1—C2B	116.8 (2)	C61—C62—C63	121.2 (3)
O1—C1—C2A	122.0 (2)	C61—C62—H62	119.4
C11—C1—C2A	114.6 (3)	C63—C62—H62	119.4
C3A—C2A—C1	120.4 (4)	C64—C63—C62	121.1 (3)
C3A—C2A—H2A1	107.2	C64—C63—H63	119.4
C1—C2A—H2A1	107.2	C62—C63—H63	119.4
C3A—C2A—H2A2	107.2	C63—C64—C65	119.3 (2)
C1—C2A—H2A2	107.2	C63—C64—H64	120.3
H2A1—C2A—H2A2	106.9	C65—C64—H64	120.3
C2A—C3A—C4	125.5 (4)	C64—C65—C66	118.9 (3)
C2A—C3A—C31	122.0 (4)	C64—C65—H65	120.6
C4—C3A—C31	101.9 (3)	C66—C65—H65	120.6
C2A—C3A—H3A	100.8	C61—C66—C65	120.8 (3)
C4—C3A—H3A	100.8	C61—C66—H66A	119.6
C31—C3A—H3A	100.8	C65—C66—H66A	119.6
C3B—C2B—C1	120.3 (4)	C61—C66—H66	119.6
C3B—C2B—H2B1	107.3	C65—C66—H66	119.6
C1—C2B—H2B1	107.3	C6B—C7—C8	122.8 (3)
C3B—C2B—H2B2	107.3	C6A—C7—C8	109.5 (2)
C1—C2B—H2B2	107.3	C6A—C7—H7A	109.8
H2B1—C2B—H2B2	106.9	C8—C7—H7A	109.8
C2B—C3B—C4	120.9 (4)	C6A—C7—H7B	109.8
C2B—C3B—C31	124.2 (4)	C8—C7—H7B	109.8
C4—C3B—C31	106.8 (3)	H7A—C7—H7B	108.2
C2B—C3B—H3B	99.5	C6B—C7—H7C	106.6
C4—C3B—H3B	99.5	C8—C7—H7C	106.6
C31—C3B—H3B	99.5	C6B—C7—H7D	106.6
C32—C31—C36	118.7 (3)	C8—C7—H7D	106.6
C32—C31—C3B	105.5 (4)	H7C—C7—H7D	106.6
C36—C31—C3B	134.7 (4)	O8—C8—C14	121.73 (19)
C32—C31—C3A	134.0 (3)	O8—C8—C7	119.51 (19)
C36—C31—C3A	107.2 (4)	C14—C8—C7	118.70 (19)
C31—C32—C33	120.6 (3)	C11—C9—C14	107.62 (15)
C31—C32—H32	119.7	C11—C9—C1'	112.62 (16)
C33—C32—H32	119.7	C14—C9—C1'	111.48 (16)
C34—C33—C32	119.4 (3)	C11—C9—H9	108.3
C34—C33—H33	120.3	C14—C9—H9	108.3
C32—C33—H33	120.3	C1'—C9—H9	108.3
C35—C34—C33	120.5 (3)	C12—C11—C1	121.16 (18)
C35—C34—H34	119.7	C12—C11—C9	120.74 (17)
C33—C34—H34	119.7	C1—C11—C9	118.10 (17)
C34—C35—C36	119.6 (3)	C11—C12—N10	120.59 (17)
C34—C35—H35	120.2	C11—C12—C4	122.66 (18)
C36—C35—H35	120.2	N10—C12—C4	116.67 (17)
C31—C36—C35	121.1 (3)	N10—C13—C14	119.85 (18)
C31—C36—H36A	119.5	N10—C13—C5	118.23 (17)
C35—C36—H36A	119.5	C14—C13—C5	121.89 (17)
C31—C36—H36B	119.5	C13—C14—C8	120.01 (18)
C35—C36—H36B	119.5	C13—C14—C9	120.03 (17)
C12—C4—C3B	113.8 (2)	C8—C14—C9	119.87 (17)
C12—C4—C3A	111.0 (2)	C13—N10—C12	119.05 (16)
C12—C4—H4A	109.4	C13—N10—C15	122.07 (16)
C3A—C4—H4A	109.4	C12—N10—C15	118.77 (15)
C12—C4—H4B	109.4	N10—C15—C16	111.18 (16)
C3A—C4—H4B	109.4	N10—C15—H15A	109.4
H4A—C4—H4B	108.0	C16—C15—H15A	109.4
C12—C4—H4C	108.8	N10—C15—H15B	109.4
C3B—C4—H4C	108.8	C16—C15—H15B	109.4
C12—C4—H4D	108.8	H15A—C15—H15B	108.0
C3B—C4—H4D	108.8	O16—C16—C15	107.94 (17)
H4C—C4—H4D	107.7	O16—C16—H16A	110.1
C13—C5—C6A	112.05 (17)	C15—C16—H16A	110.1
C13—C5—C6B	112.7 (3)	O16—C16—H16B	110.1
C13—C5—H5A	109.2	C15—C16—H16B	110.1
C6A—C5—H5A	109.2	H16A—C16—H16B	108.4
C13—C5—H5B	109.2	C16—O16—Br3'^i	141.43 (14)
C6A—C5—H5B	109.2	C16—O16—H16O	105 (3)
H5A—C5—H5B	107.9	Br3'^i—O16—H16O	96 (3)
C13—C5—H5C	110 (5)	C6'—C1'—C2'	118.60 (19)
C6B—C5—H5C	100 (5)	C6'—C1'—C9	121.04 (18)
C13—C5—H5D	107 (6)	C2'—C1'—C9	120.31 (17)
C6B—C5—H5D	120 (6)	O2'—C2'—C3'	117.75 (18)
H5C—C5—H5D	106 (8)	O2'—C2'—C1'	123.03 (18)
C7—C6A—C5	111.7 (2)	C3'—C2'—C1'	119.20 (19)
C7—C6A—C61	113.1 (2)	C2'—O2'—H2'O	114 (2)
C5—C6A—C61	107.9 (2)	C4'—C3'—C2'	121.9 (2)
C7—C6A—H6A	108.0	C4'—C3'—Br3'	118.69 (16)
C5—C6A—H6A	108.0	C2'—C3'—Br3'	119.43 (16)
C61—C6A—H6A	108.0	C5'—C4'—C3'	118.0 (2)
C7—C6B—C5	114.4 (5)	C5'—C4'—H4'	121.0
C7—C6B—C61	113.3 (5)	C3'—C4'—H4'	121.0
C5—C6B—C61	102.7 (5)	C6'—C5'—C4'	121.5 (2)
C7—C6B—H6B	108.7	C6'—C5'—Cl5'	119.15 (18)
C5—C6B—H6B	108.7	C4'—C5'—Cl5'	119.32 (18)
C61—C6B—H6B	108.7	C5'—C6'—C1'	120.7 (2)
C62—C61—C66	118.7 (2)	C5'—C6'—H6'	119.6
C62—C61—C6A	114.7 (3)	C1'—C6'—H6'	119.6
C66—C61—C6A	126.5 (3)
O1—C1—C2A—C3A	−176.6 (5)	O1—C1—C11—C9	1.9 (4)
C11—C1—C2A—C3A	−11.9 (8)	C2B—C1—C11—C9	164.9 (4)
C1—C2A—C3A—C4	−8.1 (10)	C2A—C1—C11—C9	−162.9 (4)
C1—C2A—C3A—C31	−146.2 (6)	C14—C9—C11—C12	31.2 (3)
O1—C1—C2B—C3B	−179.8 (5)	C1'—C9—C11—C12	−92.0 (2)
C11—C1—C2B—C3B	16.9 (7)	C14—C9—C11—C1	−148.5 (2)
C1—C2B—C3B—C4	−1.0 (9)	C1'—C9—C11—C1	88.2 (2)
C1—C2B—C3B—C31	143.5 (6)	C1—C11—C12—N10	173.7 (2)
C2B—C3B—C31—C32	85.6 (7)	C9—C11—C12—N10	−6.1 (3)
C4—C3B—C31—C32	−125.8 (4)	C1—C11—C12—C4	−3.0 (3)
C2B—C3B—C31—C36	−106.7 (6)	C9—C11—C12—C4	177.19 (18)
C4—C3B—C31—C36	41.9 (7)	C3B—C4—C12—C11	18.4 (4)
C2A—C3A—C31—C32	55.6 (8)	C3A—C4—C12—C11	−15.3 (4)
C4—C3A—C31—C32	−90.6 (4)	C3B—C4—C12—N10	−158.5 (4)
C2A—C3A—C31—C36	−121.9 (6)	C3A—C4—C12—N10	167.9 (3)
C4—C3A—C31—C36	91.9 (4)	C6A—C5—C13—N10	−176.0 (2)
C36—C31—C32—C33	−0.7 (5)	C6B—C5—C13—N10	145.0 (4)
C3B—C31—C32—C33	169.3 (3)	C6A—C5—C13—C14	6.0 (3)
C3A—C31—C32—C33	−178.0 (3)	C6B—C5—C13—C14	−33.0 (4)
C31—C32—C33—C34	0.3 (5)	N10—C13—C14—C8	−162.73 (19)
C32—C33—C34—C35	−0.1 (6)	C5—C13—C14—C8	15.3 (3)
C33—C34—C35—C36	0.3 (6)	N10—C13—C14—C9	13.7 (3)
C32—C31—C36—C35	0.9 (5)	C5—C13—C14—C9	−168.33 (17)
C3B—C31—C36—C35	−165.5 (4)	O8—C8—C14—C13	179.0 (2)
C3A—C31—C36—C35	178.9 (3)	C7—C8—C14—C13	1.7 (3)
C34—C35—C36—C31	−0.8 (5)	O8—C8—C14—C9	2.6 (3)
C2B—C3B—C4—C12	−15.9 (7)	C7—C8—C14—C9	−174.7 (2)
C31—C3B—C4—C12	−165.8 (3)	C11—C9—C14—C13	−35.1 (2)
C2A—C3A—C4—C12	21.5 (7)	C1'—C9—C14—C13	88.9 (2)
C31—C3A—C4—C12	166.1 (3)	C11—C9—C14—C8	141.31 (19)
C13—C5—C6A—C7	−43.4 (3)	C1'—C9—C14—C8	−94.7 (2)
C13—C5—C6A—C61	−168.4 (2)	C14—C13—N10—C12	15.8 (3)
C13—C5—C6B—C7	34.3 (7)	C5—C13—N10—C12	−162.27 (17)
C13—C5—C6B—C61	157.5 (3)	C14—C13—N10—C15	−167.96 (18)
C7—C6A—C61—C62	130.3 (3)	C5—C13—N10—C15	14.0 (3)
C5—C6A—C61—C62	−105.7 (3)	C11—C12—N10—C13	−20.0 (3)
C7—C6A—C61—C66	−53.9 (4)	C4—C12—N10—C13	156.96 (18)
C5—C6A—C61—C66	70.1 (3)	C11—C12—N10—C15	163.66 (19)
C7—C6B—C61—C62	73.4 (8)	C4—C12—N10—C15	−19.4 (3)
C5—C6B—C61—C62	−50.6 (9)	C13—N10—C15—C16	97.4 (2)
C7—C6B—C61—C66	−116.4 (5)	C12—N10—C15—C16	−86.4 (2)
C5—C6B—C61—C66	119.6 (4)	N10—C15—C16—O16	−75.8 (2)
C66—C61—C62—C63	0.7 (4)	C15—C16—O16—Br3'^i	80.6 (3)
C6A—C61—C62—C63	176.9 (2)	C11—C9—C1'—C6'	24.5 (3)
C6B—C61—C62—C63	169.5 (6)	C14—C9—C1'—C6'	−96.6 (2)
C61—C62—C63—C64	−0.5 (4)	C11—C9—C1'—C2'	−158.07 (18)
C62—C63—C64—C65	0.1 (4)	C14—C9—C1'—C2'	80.8 (2)
C63—C64—C65—C66	0.2 (4)	C6'—C1'—C2'—O2'	−179.77 (18)
C62—C61—C66—C65	−0.4 (4)	C9—C1'—C2'—O2'	2.7 (3)
C6A—C61—C66—C65	−176.1 (2)	C6'—C1'—C2'—C3'	−0.9 (3)
C6B—C61—C66—C65	−174.8 (3)	C9—C1'—C2'—C3'	−178.40 (18)
C64—C65—C66—C61	0.0 (4)	O2'—C2'—C3'—C4'	−179.7 (2)
C5—C6B—C7—C8	−20.7 (8)	C1'—C2'—C3'—C4'	1.3 (3)
C61—C6B—C7—C8	−138.1 (4)	O2'—C2'—C3'—Br3'	−0.8 (3)
C5—C6A—C7—C8	58.8 (3)	C1'—C2'—C3'—Br3'	−179.80 (15)
C61—C6A—C7—C8	−179.2 (2)	C2'—C3'—C4'—C5'	−0.6 (3)
C6B—C7—C8—O8	−175.2 (5)	Br3'—C3'—C4'—C5'	−179.42 (18)
C6A—C7—C8—O8	143.9 (2)	C3'—C4'—C5'—C6'	−0.7 (4)
C6B—C7—C8—C14	2.2 (6)	C3'—C4'—C5'—Cl5'	179.59 (18)
C6A—C7—C8—C14	−38.7 (3)	C4'—C5'—C6'—C1'	1.2 (4)
O1—C1—C11—C12	−177.9 (2)	Cl5'—C5'—C6'—C1'	−179.13 (17)
C2B—C1—C11—C12	−14.9 (5)	C2'—C1'—C6'—C5'	−0.4 (3)
C2A—C1—C11—C12	17.3 (5)	C9—C1'—C6'—C5'	177.2 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

Cg7 and Cg8 are the centroids of the C31–C36 and C61–C66 phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2′—H2′O···O8	0.85 (3)	1.79 (3)	2.626 (2)	170 (3)
O16—H16O···O8^ii	0.84 (4)	1.97 (4)	2.782 (2)	163 (4)
C15—H15A···O16^iii	0.99	2.68	3.622 (3)	159
C5—H5A···O8^iv	0.99	2.69	3.669 (3)	172
C5—H5A···O2′^iv	0.99	2.70	3.336 (3)	122
C15—H15B···O1^iv	0.99	2.47	3.451 (3)	172
C34—H34···Cl5′^v	0.95	2.87	3.560 (3)	131
C16—H16B···Cg8^iii	0.99	2.66	3.529 (3)	147
C65—H65···Cg7^vi	0.95	2.78	3.648 (4)	152

Symmetry codes: (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, −y+1, −z; (iv) x, −y+1/2, z−1/2; (v) −x+2, y−1/2, −z+1/2; (vi) x−1, −y−1/2, z−3/2.