2-[4,5-Bis(4-bromo­phen­yl)-1-(4-tert-but­ylphen­yl)-1H-imidazol-2-yl]-4,6-di­chloro­phenol

In the title compound, C₃₁H₂₄Br₂Cl₂N₂O, the dihedral angles subtended by the tert-butyl-phenyl, 4,6-di­chloro­phenol and 4-bromo­phenyl (×2) rings are 70.7 (3), 8.1 (3), 28.1 (3) and 84.2 (3)°, respectively. The orientations of the pendant rings may be related to intra­molecular O—H...N and C—H...π inter­actions. One of the tert-butyl methyl groups is disordered over two sets of sites in a 0.54 (3):0.46 (3) ratio. In the crystal, a weak C—H...π inter­action generates inversion dimers.

Key indicators

• Single-crystal X-ray study
• T = 373 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in main residue
• R factor = 0.064
• wR factor = 0.239
• Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of .        200 Ang   3
PLAT920_ALERT_1_B Theta(Max)  in CIF and FCF Differ by ...........       3.00 Degree
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          3 Check

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.80 Report
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C10 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C29 Check
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C4       -C9              1.37 Ang.
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C26      -C31             1.36 Ang.
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00913 Ang.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H11F     ..H12C     .       1.87 Ang.
                                                      x,y,z  =      1_555 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H27      ..N2       .       2.68 Ang.
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          8 Check
PLAT939_ALERT_3_C Large Value of Not (SHELXL) Weight Optimized S .      18.95 Check
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  4.24A   From C12             2.02 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  4.24A   From C12             1.86 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  4.24A   From C12             1.86 eA-3

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.18 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       7.36 Why ?
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         3% Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        64% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Hmax Differ           3 Units
PLAT951_ALERT_5_G Calculated (ThMax) and CIF-Reported Kmax Differ           2 Units
PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ           4 Units
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           3 Units
PLAT957_ALERT_1_G Calculated (ThMax) and Actual (FCF) Kmax Differ           2 Units
PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ           4 Units
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

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

   5 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
   7 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   5 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXLT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: CAMERON (Watkin et al., 1996).

2-[4,5-Bis(4-bromophenyl)-1-(4-tert-butylphenyl)-1H-imidazol-2-yl]-4,6-dichlorophenol

Crystal data

C31H24Br2Cl2N2O	F(000) = 2688
Mr = 671.24	Dx = 1.430 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.7619 (5) Å	Cell parameters from 3839 reflections
b = 12.7435 (4) Å	θ = 2.0–22.0°
c = 28.2194 (8) Å	µ = 2.80 mm^−1
β = 102.478 (2)°	T = 373 K
V = 6236.5 (3) Å^3	Block, colorless
Z = 8	0.16 × 0.15 × 0.14 mm

Data collection

Bruker SMART APEX CCD diffractometer	3305 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −18→18
Tmin = 0.646, Tmax = 0.676	k = −13→13
38305 measured reflections	l = −29→29
3839 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.239	w = 1/[σ^2(Fo^2) + (0.1772P)^2 + 7.3582P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
3839 reflections	Δρmax = 2.03 e Å^−3
353 parameters	Δρmin = −0.53 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	Occ. (<1)
Br2	0.37961 (5)	0.94032 (8)	0.22600 (3)	0.0880 (4)
Br1	0.23913 (4)	0.66001 (7)	−0.09750 (3)	0.0874 (4)
Cl1	0.83979 (12)	0.86713 (16)	−0.08924 (7)	0.0808 (6)
Cl2	0.93419 (14)	1.0667 (2)	0.07944 (9)	0.1126 (10)
N1	0.6357 (3)	0.9183 (4)	0.07290 (16)	0.0441 (11)
C1	0.6612 (3)	0.8957 (4)	0.03174 (19)	0.0438 (13)
N2	0.6050 (3)	0.8543 (4)	−0.00143 (17)	0.0465 (12)
C2	0.5402 (3)	0.8518 (4)	0.0183 (2)	0.0459 (14)
C3	0.5576 (3)	0.8907 (4)	0.0646 (2)	0.0438 (13)
C4	0.6785 (3)	0.9547 (4)	0.11935 (19)	0.0431 (13)
C14	0.7370 (3)	0.9191 (4)	0.0217 (2)	0.0464 (14)
C21	0.4692 (4)	0.7306 (5)	−0.0446 (2)	0.0558 (15)
H21	0.516363	0.708611	−0.050285	0.067*
C26	0.5132 (3)	0.9005 (4)	0.10235 (19)	0.0426 (13)
C25	0.3960 (4)	0.8382 (5)	−0.0018 (2)	0.0555 (16)
H25	0.394035	0.889568	0.021273	0.067*
C29	0.4321 (3)	0.9217 (5)	0.1747 (2)	0.0520 (15)
C23	0.3317 (4)	0.7187 (5)	−0.0614 (2)	0.0586 (16)
C19	0.7511 (3)	0.8830 (4)	−0.0234 (2)	0.0467 (14)
C20	0.4676 (3)	0.8068 (5)	−0.0095 (2)	0.0472 (14)
C16	0.8641 (4)	0.9950 (5)	0.0397 (3)	0.0634 (18)
C31	0.5155 (4)	0.8252 (5)	0.1367 (2)	0.0586 (16)
H31	0.544710	0.764970	0.135677	0.070*
C18	0.8229 (3)	0.9081 (5)	−0.0342 (2)	0.0525 (15)
C15	0.7941 (4)	0.9753 (5)	0.0527 (2)	0.0556 (16)
H15	0.785674	0.999713	0.082200	0.067*
C7	0.7660 (4)	1.0275 (5)	0.2066 (2)	0.0523 (15)
C5	0.7312 (4)	0.8902 (5)	0.1474 (2)	0.0548 (15)
H5	0.737765	0.821949	0.137379	0.066*
C30	0.4755 (4)	0.8365 (5)	0.1730 (3)	0.0649 (18)
H30	0.478605	0.784616	0.196467	0.078*
C24	0.3288 (4)	0.7958 (5)	−0.0271 (2)	0.0578 (16)
H24	0.281729	0.818176	−0.021413	0.069*
C27	0.4672 (4)	0.9865 (5)	0.1043 (2)	0.0644 (17)
H27	0.463475	1.038139	0.080597	0.077*
C6	0.7747 (4)	0.9267 (5)	0.1906 (2)	0.0579 (16)
H6	0.810783	0.882507	0.209454	0.069*
C9	0.6670 (4)	1.0540 (5)	0.1352 (2)	0.0553 (16)
H9	0.629949	1.097589	0.116773	0.066*
C28	0.4262 (4)	0.9985 (6)	0.1405 (3)	0.0646 (17)
H28	0.395513	1.057269	0.141495	0.077*
C17	0.8784 (4)	0.9612 (5)	−0.0025 (2)	0.0573 (16)
H17	0.926012	0.974023	−0.009986	0.069*
C8	0.7105 (4)	1.0880 (5)	0.1781 (3)	0.0633 (18)
H8	0.702101	1.155354	0.188617	0.076*
C22	0.4018 (4)	0.6868 (5)	−0.0711 (2)	0.0605 (17)
H22	0.403347	0.636937	−0.094918	0.073*
C10	0.8204 (4)	1.0707 (6)	0.2521 (3)	0.074 (2)
C13	0.7885 (7)	1.1621 (8)	0.2744 (3)	0.105 (3)
H13A	0.783692	1.221159	0.252859	0.158*
H13B	0.822629	1.179705	0.304664	0.158*
H13C	0.738721	1.144285	0.280167	0.158*
C12	0.8438 (6)	0.9853 (10)	0.2916 (3)	0.114 (4)
H12A	0.798250	0.954386	0.298811	0.170*
H12B	0.874070	1.016495	0.320452	0.170*
H12C	0.873526	0.932020	0.279996	0.170*
C11	0.888 (2)	1.133 (3)	0.2282 (14)	0.099 (7)	0.46 (3)
H11A	0.863919	1.184217	0.204867	0.148*	0.46 (3)
H11B	0.915147	1.082875	0.212585	0.148*	0.46 (3)
H11C	0.924449	1.167696	0.253678	0.148*	0.46 (3)
C11'	0.8959 (19)	1.086 (3)	0.2423 (11)	0.099 (7)	0.54 (3)
H11D	0.926404	1.128018	0.267490	0.148*	0.54 (3)
H11E	0.891222	1.120856	0.211635	0.148*	0.54 (3)
H11F	0.920299	1.019054	0.241150	0.148*	0.54 (3)
O1	0.7002 (3)	0.8310 (3)	−0.05618 (15)	0.0588 (11)
H1	0.660977	0.821259	−0.045930	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br2	0.0757 (6)	0.1339 (8)	0.0630 (6)	0.0197 (5)	0.0340 (5)	0.0061 (4)
Br1	0.0554 (6)	0.1039 (7)	0.0923 (7)	−0.0211 (4)	−0.0076 (4)	−0.0165 (4)
Cl1	0.0874 (14)	0.0892 (12)	0.0797 (13)	−0.0099 (10)	0.0485 (11)	−0.0157 (10)
Cl2	0.0775 (14)	0.166 (2)	0.0940 (16)	−0.0665 (15)	0.0169 (12)	−0.0298 (15)
N1	0.041 (3)	0.054 (3)	0.035 (3)	−0.006 (2)	0.004 (2)	−0.001 (2)
C1	0.043 (3)	0.051 (3)	0.036 (3)	−0.001 (3)	0.004 (3)	0.000 (2)
N2	0.045 (3)	0.054 (3)	0.039 (3)	−0.006 (2)	0.006 (2)	0.005 (2)
C2	0.044 (3)	0.053 (3)	0.038 (3)	−0.001 (2)	0.004 (3)	0.005 (2)
C3	0.041 (3)	0.051 (3)	0.038 (3)	0.000 (3)	0.004 (2)	0.004 (2)
C4	0.042 (3)	0.052 (3)	0.035 (3)	−0.010 (3)	0.007 (3)	0.002 (2)
C14	0.044 (3)	0.050 (3)	0.044 (3)	−0.004 (3)	0.007 (3)	0.007 (3)
C21	0.052 (4)	0.059 (4)	0.056 (4)	0.000 (3)	0.009 (3)	−0.004 (3)
C26	0.037 (3)	0.051 (3)	0.038 (3)	−0.003 (3)	0.004 (2)	0.005 (3)
C25	0.051 (4)	0.067 (4)	0.047 (3)	−0.004 (3)	0.009 (3)	0.001 (3)
C29	0.043 (3)	0.071 (4)	0.041 (3)	0.001 (3)	0.008 (3)	0.003 (3)
C23	0.049 (4)	0.065 (4)	0.057 (4)	−0.012 (3)	0.000 (3)	0.005 (3)
C19	0.048 (3)	0.046 (3)	0.045 (3)	0.003 (3)	0.007 (3)	0.005 (3)
C20	0.041 (3)	0.058 (3)	0.040 (3)	−0.003 (3)	0.003 (3)	0.010 (3)
C16	0.047 (4)	0.072 (4)	0.068 (4)	−0.018 (3)	0.004 (3)	0.001 (4)
C31	0.052 (4)	0.061 (4)	0.065 (4)	0.011 (3)	0.017 (3)	0.005 (3)
C18	0.048 (4)	0.054 (3)	0.061 (4)	0.004 (3)	0.024 (3)	0.007 (3)
C15	0.052 (4)	0.064 (4)	0.050 (4)	−0.011 (3)	0.010 (3)	−0.003 (3)
C7	0.049 (4)	0.068 (4)	0.041 (3)	−0.016 (3)	0.012 (3)	−0.005 (3)
C5	0.060 (4)	0.048 (3)	0.052 (4)	−0.004 (3)	0.002 (3)	−0.003 (3)
C30	0.070 (5)	0.074 (4)	0.058 (4)	0.003 (4)	0.031 (4)	0.020 (3)
C24	0.040 (3)	0.076 (4)	0.057 (4)	−0.003 (3)	0.008 (3)	0.004 (3)
C27	0.076 (5)	0.065 (4)	0.054 (4)	0.007 (4)	0.017 (3)	0.012 (3)
C6	0.062 (4)	0.060 (4)	0.046 (4)	−0.007 (3)	−0.002 (3)	0.004 (3)
C9	0.060 (4)	0.051 (4)	0.053 (4)	0.005 (3)	0.008 (3)	0.000 (3)
C28	0.059 (4)	0.075 (4)	0.063 (4)	0.013 (3)	0.020 (3)	−0.004 (4)
C17	0.047 (4)	0.062 (4)	0.068 (4)	−0.006 (3)	0.023 (3)	0.005 (3)
C8	0.070 (4)	0.054 (4)	0.065 (4)	−0.006 (3)	0.012 (4)	−0.017 (3)
C22	0.053 (4)	0.066 (4)	0.059 (4)	−0.003 (3)	0.004 (3)	−0.009 (3)
C10	0.064 (4)	0.099 (5)	0.058 (4)	−0.028 (4)	0.010 (4)	−0.026 (4)
C13	0.117 (8)	0.107 (7)	0.081 (6)	−0.015 (5)	−0.001 (5)	−0.043 (5)
C12	0.110 (8)	0.145 (9)	0.065 (5)	0.013 (6)	−0.028 (5)	−0.028 (6)
C11	0.091 (10)	0.11 (2)	0.092 (16)	−0.072 (16)	0.019 (11)	−0.005 (12)
C11'	0.091 (10)	0.11 (2)	0.092 (16)	−0.072 (16)	0.019 (11)	−0.005 (12)
O1	0.057 (3)	0.071 (3)	0.048 (2)	−0.012 (2)	0.011 (2)	−0.008 (2)

Geometric parameters (Å, º)

Br2—C29	1.899 (6)	C18—C17	1.361 (9)
Br1—C23	1.891 (6)	C15—H15	0.9300
Cl1—C18	1.725 (6)	C7—C8	1.368 (10)
Cl2—C16	1.743 (6)	C7—C6	1.380 (9)
N1—C1	1.365 (7)	C7—C10	1.532 (9)
N1—C3	1.400 (7)	C5—C6	1.375 (9)
N1—C4	1.443 (7)	C5—H5	0.9300
C1—N2	1.321 (7)	C30—H30	0.9300
C1—C14	1.466 (8)	C24—H24	0.9300
N2—C2	1.383 (7)	C27—C28	1.386 (10)
C2—C3	1.369 (8)	C27—H27	0.9300
C2—C20	1.473 (8)	C6—H6	0.9300
C3—C26	1.462 (8)	C9—C8	1.359 (10)
C4—C5	1.364 (9)	C9—H9	0.9300
C4—C9	1.371 (8)	C28—H28	0.9300
C14—C15	1.388 (9)	C17—H17	0.9300
C14—C19	1.424 (8)	C8—H8	0.9300
C21—C22	1.385 (9)	C22—H22	0.9300
C21—C20	1.391 (9)	C10—C11'	1.44 (3)
C21—H21	0.9300	C10—C13	1.493 (12)
C26—C31	1.359 (9)	C10—C12	1.550 (14)
C26—C27	1.375 (9)	C10—C11	1.70 (3)
C25—C24	1.362 (9)	C13—H13A	0.9600
C25—C20	1.395 (9)	C13—H13B	0.9600
C25—H25	0.9300	C13—H13C	0.9600
C29—C30	1.338 (9)	C12—H12A	0.9600
C29—C28	1.362 (9)	C12—H12B	0.9600
C23—C24	1.387 (10)	C12—H12C	0.9600
C23—C22	1.393 (9)	C11—H11A	0.9600
C19—O1	1.323 (7)	C11—H11B	0.9600
C19—C18	1.410 (8)	C11—H11C	0.9600
C16—C17	1.339 (10)	C11'—H11D	0.9600
C16—C15	1.395 (9)	C11'—H11E	0.9600
C31—C30	1.373 (9)	C11'—H11F	0.9600
C31—H31	0.9300	O1—H1	0.8200
C1—N1—C3	107.6 (4)	C31—C30—H30	119.7
C1—N1—C4	129.4 (5)	C25—C24—C23	119.1 (6)
C3—N1—C4	122.8 (5)	C25—C24—H24	120.5
N2—C1—N1	110.4 (5)	C23—C24—H24	120.5
N2—C1—C14	121.9 (5)	C26—C27—C28	121.9 (6)
N1—C1—C14	127.5 (5)	C26—C27—H27	119.1
C1—N2—C2	106.9 (5)	C28—C27—H27	119.1
C3—C2—N2	109.9 (5)	C5—C6—C7	121.6 (6)
C3—C2—C20	129.8 (5)	C5—C6—H6	119.2
N2—C2—C20	120.2 (5)	C7—C6—H6	119.2
C2—C3—N1	105.2 (5)	C8—C9—C4	119.3 (6)
C2—C3—C26	132.9 (5)	C8—C9—H9	120.3
N1—C3—C26	121.9 (5)	C4—C9—H9	120.3
C5—C4—C9	119.9 (6)	C29—C28—C27	118.1 (6)
C5—C4—N1	119.6 (5)	C29—C28—H28	121.0
C9—C4—N1	120.5 (5)	C27—C28—H28	121.0
C15—C14—C19	119.0 (5)	C16—C17—C18	119.7 (6)
C15—C14—C1	124.0 (5)	C16—C17—H17	120.2
C19—C14—C1	117.0 (5)	C18—C17—H17	120.2
C22—C21—C20	121.2 (6)	C9—C8—C7	122.8 (6)
C22—C21—H21	119.4	C9—C8—H8	118.6
C20—C21—H21	119.4	C7—C8—H8	118.6
C31—C26—C27	117.5 (6)	C21—C22—C23	118.8 (6)
C31—C26—C3	121.4 (5)	C21—C22—H22	120.6
C27—C26—C3	121.1 (5)	C23—C22—H22	120.6
C24—C25—C20	122.0 (6)	C11'—C10—C13	115.5 (14)
C24—C25—H25	119.0	C11'—C10—C7	109.4 (13)
C20—C25—H25	119.0	C13—C10—C7	114.0 (7)
C30—C29—C28	120.9 (6)	C11'—C10—C12	96.7 (16)
C30—C29—Br2	120.8 (5)	C13—C10—C12	108.1 (7)
C28—C29—Br2	118.3 (5)	C7—C10—C12	111.9 (6)
C24—C23—C22	120.9 (6)	C13—C10—C11	99.7 (17)
C24—C23—Br1	119.8 (5)	C7—C10—C11	102.0 (13)
C22—C23—Br1	119.2 (5)	C12—C10—C11	120.7 (17)
O1—C19—C18	118.4 (5)	C10—C13—H13A	109.5
O1—C19—C14	124.1 (5)	C10—C13—H13B	109.5
C18—C19—C14	117.5 (5)	H13A—C13—H13B	109.5
C21—C20—C25	118.0 (5)	C10—C13—H13C	109.5
C21—C20—C2	120.1 (5)	H13A—C13—H13C	109.5
C25—C20—C2	121.9 (5)	H13B—C13—H13C	109.5
C17—C16—C15	121.8 (6)	C10—C12—H12A	109.5
C17—C16—Cl2	119.6 (5)	C10—C12—H12B	109.5
C15—C16—Cl2	118.5 (5)	H12A—C12—H12B	109.5
C26—C31—C30	121.1 (6)	C10—C12—H12C	109.5
C26—C31—H31	119.5	H12A—C12—H12C	109.5
C30—C31—H31	119.5	H12B—C12—H12C	109.5
C17—C18—C19	122.1 (6)	C10—C11—H11A	109.5
C17—C18—Cl1	120.1 (5)	C10—C11—H11B	109.5
C19—C18—Cl1	117.9 (5)	H11A—C11—H11B	109.5
C14—C15—C16	119.9 (6)	C10—C11—H11C	109.5
C14—C15—H15	120.1	H11A—C11—H11C	109.5
C16—C15—H15	120.1	H11B—C11—H11C	109.5
C8—C7—C6	116.7 (6)	C10—C11'—H11D	109.5
C8—C7—C10	122.2 (6)	C10—C11'—H11E	109.5
C6—C7—C10	121.0 (6)	H11D—C11'—H11E	109.5
C4—C5—C6	119.6 (6)	C10—C11'—H11F	109.5
C4—C5—H5	120.2	H11D—C11'—H11F	109.5
C6—C5—H5	120.2	H11E—C11'—H11F	109.5
C29—C30—C31	120.5 (6)	C19—O1—H1	109.5
C29—C30—H30	119.7
C3—N1—C1—N2	−1.0 (6)	C14—C19—C18—C17	2.4 (9)
C4—N1—C1—N2	173.7 (5)	O1—C19—C18—Cl1	−0.9 (7)
C3—N1—C1—C14	174.4 (5)	C14—C19—C18—Cl1	−178.7 (4)
C4—N1—C1—C14	−10.9 (9)	C19—C14—C15—C16	−0.4 (9)
N1—C1—N2—C2	1.3 (6)	C1—C14—C15—C16	−179.1 (6)
C14—C1—N2—C2	−174.4 (5)	C17—C16—C15—C14	0.1 (10)
C1—N2—C2—C3	−1.0 (6)	Cl2—C16—C15—C14	179.5 (5)
C1—N2—C2—C20	−178.2 (5)	C9—C4—C5—C6	−2.5 (9)
N2—C2—C3—N1	0.4 (6)	N1—C4—C5—C6	176.8 (5)
C20—C2—C3—N1	177.3 (5)	C28—C29—C30—C31	0.4 (11)
N2—C2—C3—C26	−176.0 (6)	Br2—C29—C30—C31	−177.7 (5)
C20—C2—C3—C26	0.8 (10)	C26—C31—C30—C29	1.1 (11)
C1—N1—C3—C2	0.4 (6)	C20—C25—C24—C23	0.3 (9)
C4—N1—C3—C2	−174.8 (5)	C22—C23—C24—C25	−1.8 (10)
C1—N1—C3—C26	177.3 (5)	Br1—C23—C24—C25	−179.2 (5)
C4—N1—C3—C26	2.1 (8)	C31—C26—C27—C28	1.8 (10)
C1—N1—C4—C5	−67.3 (8)	C3—C26—C27—C28	−178.3 (6)
C3—N1—C4—C5	106.7 (6)	C4—C5—C6—C7	0.4 (10)
C1—N1—C4—C9	112.0 (7)	C8—C7—C6—C5	2.0 (10)
C3—N1—C4—C9	−74.0 (7)	C10—C7—C6—C5	−173.7 (6)
N2—C1—C14—C15	170.8 (6)	C5—C4—C9—C8	2.2 (9)
N1—C1—C14—C15	−4.1 (9)	N1—C4—C9—C8	−177.2 (6)
N2—C1—C14—C19	−7.9 (8)	C30—C29—C28—C27	−0.8 (10)
N1—C1—C14—C19	177.2 (5)	Br2—C29—C28—C27	177.4 (5)
C2—C3—C26—C31	93.4 (8)	C26—C27—C28—C29	−0.4 (11)
N1—C3—C26—C31	−82.5 (7)	C15—C16—C17—C18	1.5 (10)
C2—C3—C26—C27	−86.5 (8)	Cl2—C16—C17—C18	−178.0 (5)
N1—C3—C26—C27	97.6 (7)	C19—C18—C17—C16	−2.8 (10)
C15—C14—C19—O1	−178.4 (5)	Cl1—C18—C17—C16	178.3 (5)
C1—C14—C19—O1	0.4 (8)	C4—C9—C8—C7	0.3 (10)
C15—C14—C19—C18	−0.8 (8)	C6—C7—C8—C9	−2.3 (10)
C1—C14—C19—C18	178.0 (5)	C10—C7—C8—C9	173.3 (7)
C22—C21—C20—C25	−0.1 (9)	C20—C21—C22—C23	−1.4 (10)
C22—C21—C20—C2	179.8 (6)	C24—C23—C22—C21	2.3 (10)
C24—C25—C20—C21	0.6 (9)	Br1—C23—C22—C21	179.7 (5)
C24—C25—C20—C2	−179.2 (5)	C8—C7—C10—C11'	−105.9 (17)
C3—C2—C20—C21	−150.0 (6)	C6—C7—C10—C11'	69.6 (17)
N2—C2—C20—C21	26.6 (8)	C8—C7—C10—C13	25.1 (10)
C3—C2—C20—C25	29.9 (9)	C6—C7—C10—C13	−159.5 (7)
N2—C2—C20—C25	−153.5 (5)	C8—C7—C10—C12	148.2 (7)
C27—C26—C31—C30	−2.2 (10)	C6—C7—C10—C12	−36.3 (9)
C3—C26—C31—C30	177.9 (6)	C8—C7—C10—C11	−81.4 (18)
O1—C19—C18—C17	−179.9 (6)	C6—C7—C10—C11	94.0 (18)

Hydrogen-bond geometry (Å, º)

Cg2 and Cg4 are the centroids of the C4–C9 and C20–C25 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.81	2.542 (7)	148
C27—H27···N2^i	0.93	2.68	3.547 (6)	156
C15—H15···Cg2	0.93	2.76	3.621 (7)	154
C9—H9···Cg4^ii	0.93	2.85	3.641 (6)	144

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