1-[2-(Bi­phenyl-4-yl)-2-oxoethyl]-4-(N,N-di­methyl­amino)­pyridinium bromide hemihydrate

The title compound, C₂₁H₂₁N₂O⁺·Br⁻·0.5H₂O, crystallizes in a monoclinic unit cell with two cations, two anions and one water mol­ecule in the asymmetric unit. The conformations of the two independent cations are different. The crystal packing is stabilized by O—H...Br and C—H...Br interactions and weak intermolecular C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.056
• wR factor = 0.140
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A    ..  BR2     ..       2.98 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7B    ..  O1B     ..       2.76 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14A   ..  O1#     ..       2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21A   ..  O1#     ..       2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12B   ..  BR1     ..       2.99 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21B   ..  O1#     ..       2.85 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C21B   ..  O1#     ..       3.77 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

1-[2-(Biphenyl-4-yl)-2-oxoethyl]-4-(N,N-dimethylamino)pyridinium bromide hemihydrate

Crystal data

C21H21N2O^+·Br^−·0.5H2O	F(000) = 3344
Mr = 406.32	Dx = 1.384 Mg m^−3
Monoclinic, C2/c	Melting point: 534 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 21.077 (6) Å	Cell parameters from 911 reflections
b = 9.971 (3) Å	θ = 2.2–27.8°
c = 37.485 (12) Å	µ = 2.12 mm^−1
β = 98.121 (9)°	T = 298 K
V = 7799 (4) Å^3	Block, colourless
Z = 16	0.7 × 0.4 × 0.4 mm

Data collection

Bruker SMART CCD 1K diffractometer	7982 independent reflections
Radiation source: fine-focus sealed tube	4222 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
ω scans	θmax = 26.4°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −26→26
Tmin = 0.281, Tmax = 0.428	k = 0→12
31162 measured reflections	l = 0→46

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0565P)^2 + 4.0141P] where P = (Fo^2 + 2Fc^2)/3
7982 reflections	(Δ/σ)max = 0.001
471 parameters	Δρmax = 0.52 e Å^−3
2 restraints	Δρmin = −0.34 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1A	0.13559 (18)	0.9657 (4)	0.25693 (9)	0.0755 (10)
N1A	0.18824 (16)	0.7557 (3)	0.29593 (9)	0.0452 (9)
N2A	0.13303 (16)	0.7028 (3)	0.39680 (9)	0.0472 (9)
C1A	0.2048 (2)	0.7788 (4)	0.26010 (10)	0.0489 (11)
H1A	0.1949	0.6989	0.2456	0.059*
H1B	0.2506	0.7942	0.2620	0.059*
C2A	0.1575 (2)	0.6433 (4)	0.30396 (11)	0.0495 (11)
H2A	0.1483	0.5781	0.2862	0.059*
C3A	0.1396 (2)	0.6217 (4)	0.33656 (11)	0.0493 (11)
H3A	0.1186	0.5425	0.3408	0.059*
C4A	0.15230 (19)	0.7190 (4)	0.36463 (11)	0.0405 (10)
C5A	0.1870 (2)	0.8312 (4)	0.35571 (11)	0.0466 (11)
H5A	0.1988	0.8964	0.3731	0.056*
C6A	0.2038 (2)	0.8468 (4)	0.32267 (11)	0.0490 (11)
H6A	0.2269	0.9227	0.3179	0.059*
C7A	0.0993 (2)	0.5829 (5)	0.40611 (13)	0.0613 (13)
H7A	0.0649	0.5633	0.3872	0.092*
H7B	0.0822	0.5979	0.4282	0.092*
H7C	0.1285	0.5086	0.4091	0.092*
C8A	0.1473 (2)	0.8030 (5)	0.42517 (12)	0.0691 (15)
H8A	0.1916	0.8285	0.4270	0.104*
H8B	0.1390	0.7659	0.4477	0.104*
H8C	0.1207	0.8804	0.4194	0.104*
C9A	0.1700 (2)	0.8965 (5)	0.24121 (12)	0.0487 (11)
C10A	0.18073 (19)	0.9263 (4)	0.20380 (10)	0.0422 (10)
C11A	0.2017 (2)	0.8304 (4)	0.18136 (11)	0.0490 (11)
H11A	0.2103	0.7439	0.1900	0.059*
C12A	0.2099 (2)	0.8613 (4)	0.14657 (11)	0.0475 (11)
H12A	0.2237	0.7949	0.1320	0.057*
C13A	0.19800 (18)	0.9894 (4)	0.13255 (11)	0.0390 (10)
C14A	0.1774 (2)	1.0861 (4)	0.15552 (11)	0.0507 (12)
H14A	0.1700	1.1734	0.1472	0.061*
C15A	0.1679 (2)	1.0545 (4)	0.18996 (12)	0.0507 (12)
H15A	0.1527	1.1198	0.2043	0.061*
C16A	0.20660 (19)	1.0218 (4)	0.09463 (11)	0.0417 (10)
C17A	0.2404 (2)	0.9369 (5)	0.07455 (11)	0.0519 (12)
H17A	0.2592	0.8598	0.0853	0.062*
C18A	0.2469 (2)	0.9641 (5)	0.03914 (13)	0.0596 (13)
H18A	0.2697	0.9055	0.0264	0.072*
C19A	0.2201 (3)	1.0767 (5)	0.02285 (13)	0.0671 (14)
H19A	0.2242	1.0949	−0.0010	0.080*
C20A	0.1868 (3)	1.1632 (5)	0.04200 (14)	0.0736 (15)
H20A	0.1689	1.2409	0.0311	0.088*
C21A	0.1798 (2)	1.1350 (5)	0.07749 (12)	0.0614 (13)
H21A	0.1565	1.1935	0.0900	0.074*
O1B	−0.01892 (18)	0.2592 (5)	0.52468 (9)	0.1119 (17)
N1B	0.06795 (15)	0.1783 (4)	0.57855 (8)	0.0442 (9)
N2B	0.01245 (17)	0.1691 (4)	0.67933 (9)	0.0564 (10)
C1B	0.0864 (2)	0.1828 (5)	0.54266 (10)	0.0507 (12)
H1C	0.1002	0.0943	0.5362	0.061*
H1D	0.1222	0.2438	0.5426	0.061*
C2B	0.0396 (2)	0.0691 (5)	0.59020 (12)	0.0544 (12)
H2B	0.0328	−0.0049	0.5750	0.065*
C3B	0.0207 (2)	0.0630 (5)	0.62297 (12)	0.0561 (12)
H3B	0.0017	−0.0148	0.6301	0.067*
C4B	0.02954 (19)	0.1729 (4)	0.64659 (11)	0.0438 (11)
C5B	0.0579 (2)	0.2860 (4)	0.63336 (11)	0.0473 (11)
H5B	0.0643	0.3625	0.6476	0.057*
C6B	0.0761 (2)	0.2858 (4)	0.60028 (11)	0.0490 (11)
H6B	0.0948	0.3626	0.5923	0.059*
C7B	−0.0153 (3)	0.0508 (5)	0.69323 (13)	0.0812 (18)
H7D	−0.0484	0.0162	0.6754	0.122*
H7E	−0.0333	0.0738	0.7146	0.122*
H7F	0.0173	−0.0160	0.6990	0.122*
C8B	0.0231 (3)	0.2818 (6)	0.70407 (13)	0.0793 (17)
H8D	0.0593	0.3327	0.6988	0.119*
H8E	0.0312	0.2491	0.7284	0.119*
H8F	−0.0142	0.3381	0.7013	0.119*
C9B	0.0312 (2)	0.2286 (5)	0.51502 (11)	0.0562 (13)
C10B	0.0418 (2)	0.2351 (5)	0.47694 (11)	0.0491 (11)
C11B	0.0976 (2)	0.1906 (5)	0.46524 (11)	0.0537 (12)
H11B	0.1302	0.1548	0.4818	0.064*
C12B	0.1053 (2)	0.1985 (4)	0.42961 (11)	0.0518 (12)
H12B	0.1433	0.1679	0.4225	0.062*
C13B	0.0581 (2)	0.2511 (4)	0.40381 (11)	0.0404 (10)
C14B	0.0027 (2)	0.2965 (5)	0.41609 (11)	0.0513 (12)
H14B	−0.0299	0.3331	0.3997	0.062*
C15B	−0.0054 (2)	0.2887 (5)	0.45176 (12)	0.0563 (13)
H15B	−0.0431	0.3200	0.4590	0.068*
C16B	0.0662 (2)	0.2610 (4)	0.36521 (10)	0.0410 (10)
C17B	0.1226 (2)	0.2189 (5)	0.35321 (12)	0.0585 (13)
H17B	0.1557	0.1843	0.3697	0.070*
C18B	0.1299 (3)	0.2277 (5)	0.31726 (13)	0.0683 (15)
H18B	0.1677	0.1982	0.3097	0.082*
C19B	0.0820 (3)	0.2795 (5)	0.29278 (14)	0.0712 (15)
H19B	0.0872	0.2866	0.2686	0.085*
C20B	0.0261 (3)	0.3209 (5)	0.30408 (13)	0.0733 (15)
H20B	−0.0067	0.3559	0.2875	0.088*
C21B	0.0181 (2)	0.3112 (5)	0.33941 (12)	0.0595 (13)
H21B	−0.0204	0.3388	0.3465	0.071*
Br1	0.22209 (2)	0.56541 (5)	0.070795 (15)	0.06631 (19)
Br2	0.15039 (2)	0.46281 (5)	0.213027 (13)	0.06256 (18)
OW	0.13357 (18)	0.4124 (4)	0.12488 (11)	0.0674 (9)
H22	0.160	0.454	0.1134	0.08*
H23	0.139	0.438	0.1473	0.12*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.089 (3)	0.087 (3)	0.056 (2)	0.029 (2)	0.0285 (19)	0.0054 (19)
N1A	0.048 (2)	0.048 (2)	0.040 (2)	−0.0078 (18)	0.0068 (17)	0.0006 (18)
N2A	0.048 (2)	0.053 (2)	0.043 (2)	−0.0067 (18)	0.0118 (18)	−0.0027 (18)
C1A	0.049 (3)	0.059 (3)	0.040 (3)	−0.001 (2)	0.011 (2)	0.000 (2)
C2A	0.056 (3)	0.048 (3)	0.044 (3)	−0.005 (2)	0.003 (2)	−0.008 (2)
C3A	0.054 (3)	0.046 (3)	0.048 (3)	−0.014 (2)	0.007 (2)	−0.003 (2)
C4A	0.038 (3)	0.038 (2)	0.044 (3)	0.000 (2)	0.000 (2)	0.002 (2)
C5A	0.052 (3)	0.048 (3)	0.040 (3)	−0.013 (2)	0.006 (2)	−0.005 (2)
C6A	0.050 (3)	0.049 (3)	0.047 (3)	−0.014 (2)	0.003 (2)	−0.001 (2)
C7A	0.063 (3)	0.064 (3)	0.059 (3)	−0.012 (3)	0.018 (3)	0.005 (2)
C8A	0.079 (4)	0.076 (4)	0.054 (3)	−0.018 (3)	0.016 (3)	−0.014 (3)
C9A	0.048 (3)	0.052 (3)	0.046 (3)	−0.003 (2)	0.005 (2)	−0.001 (2)
C10A	0.039 (3)	0.050 (3)	0.036 (2)	−0.004 (2)	0.003 (2)	−0.003 (2)
C11A	0.055 (3)	0.046 (3)	0.047 (3)	0.008 (2)	0.011 (2)	0.010 (2)
C12A	0.053 (3)	0.043 (3)	0.048 (3)	0.009 (2)	0.016 (2)	0.000 (2)
C13A	0.035 (2)	0.042 (3)	0.040 (2)	−0.005 (2)	0.0052 (19)	−0.001 (2)
C14A	0.064 (3)	0.043 (3)	0.046 (3)	−0.001 (2)	0.008 (2)	0.000 (2)
C15A	0.059 (3)	0.049 (3)	0.045 (3)	0.002 (2)	0.008 (2)	−0.010 (2)
C16A	0.038 (2)	0.040 (3)	0.047 (3)	−0.008 (2)	0.004 (2)	−0.002 (2)
C17A	0.055 (3)	0.055 (3)	0.046 (3)	0.004 (2)	0.010 (2)	0.003 (2)
C18A	0.061 (3)	0.065 (3)	0.056 (3)	0.002 (3)	0.019 (3)	−0.003 (3)
C19A	0.086 (4)	0.069 (4)	0.050 (3)	−0.004 (3)	0.025 (3)	0.006 (3)
C20A	0.097 (4)	0.063 (3)	0.062 (3)	0.018 (3)	0.016 (3)	0.015 (3)
C21A	0.080 (4)	0.050 (3)	0.057 (3)	0.016 (3)	0.019 (3)	0.010 (2)
O1B	0.058 (2)	0.225 (5)	0.058 (2)	0.042 (3)	0.023 (2)	0.027 (3)
N1B	0.039 (2)	0.060 (2)	0.033 (2)	−0.0089 (18)	0.0041 (16)	0.0022 (18)
N2B	0.055 (2)	0.075 (3)	0.042 (2)	−0.024 (2)	0.0157 (19)	−0.006 (2)
C1B	0.042 (3)	0.070 (3)	0.040 (3)	0.000 (2)	0.008 (2)	0.005 (2)
C2B	0.068 (3)	0.052 (3)	0.042 (3)	−0.014 (3)	0.003 (2)	−0.008 (2)
C3B	0.063 (3)	0.059 (3)	0.047 (3)	−0.021 (3)	0.010 (2)	0.002 (2)
C4B	0.033 (2)	0.060 (3)	0.038 (3)	−0.011 (2)	0.004 (2)	0.001 (2)
C5B	0.053 (3)	0.050 (3)	0.041 (3)	−0.010 (2)	0.012 (2)	−0.004 (2)
C6B	0.052 (3)	0.052 (3)	0.044 (3)	−0.012 (2)	0.010 (2)	0.006 (2)
C7B	0.090 (4)	0.105 (5)	0.052 (3)	−0.044 (4)	0.021 (3)	0.003 (3)
C8B	0.084 (4)	0.104 (4)	0.055 (3)	−0.023 (3)	0.030 (3)	−0.022 (3)
C9B	0.045 (3)	0.085 (4)	0.039 (3)	−0.001 (3)	0.008 (2)	0.004 (2)
C10B	0.043 (3)	0.066 (3)	0.038 (3)	−0.006 (2)	0.007 (2)	0.004 (2)
C11B	0.043 (3)	0.079 (3)	0.039 (3)	0.009 (2)	0.007 (2)	0.012 (2)
C12B	0.049 (3)	0.066 (3)	0.043 (3)	0.008 (2)	0.015 (2)	0.010 (2)
C13B	0.041 (3)	0.041 (2)	0.040 (2)	−0.010 (2)	0.008 (2)	0.000 (2)
C14B	0.037 (3)	0.070 (3)	0.046 (3)	0.004 (2)	0.001 (2)	0.012 (2)
C15B	0.037 (3)	0.084 (4)	0.047 (3)	0.011 (2)	0.006 (2)	0.012 (3)
C16B	0.049 (3)	0.038 (2)	0.036 (2)	−0.010 (2)	0.008 (2)	−0.0006 (19)
C17B	0.054 (3)	0.077 (4)	0.045 (3)	−0.012 (3)	0.009 (2)	−0.004 (2)
C18B	0.059 (3)	0.096 (4)	0.052 (3)	−0.017 (3)	0.016 (3)	−0.009 (3)
C19B	0.086 (4)	0.085 (4)	0.044 (3)	−0.020 (3)	0.017 (3)	0.005 (3)
C20B	0.094 (4)	0.081 (4)	0.042 (3)	0.006 (3)	0.001 (3)	0.009 (3)
C21B	0.063 (3)	0.070 (3)	0.046 (3)	0.006 (3)	0.006 (3)	0.008 (2)
Br1	0.0635 (3)	0.0564 (3)	0.0828 (4)	0.0129 (3)	0.0236 (3)	0.0051 (3)
Br2	0.0712 (4)	0.0599 (3)	0.0589 (3)	0.0108 (3)	0.0173 (3)	−0.0009 (2)
OW	0.065 (2)	0.066 (2)	0.071 (3)	−0.004 (2)	0.006 (2)	0.002 (2)

Geometric parameters (Å, º)

O1A—C9A	1.212 (5)	N1B—C6B	1.343 (5)
N1A—C2A	1.350 (5)	N1B—C2B	1.345 (5)
N1A—C6A	1.358 (5)	N1B—C1B	1.453 (5)
N1A—C1A	1.453 (5)	N2B—C4B	1.327 (5)
N2A—C4A	1.336 (5)	N2B—C7B	1.445 (6)
N2A—C7A	1.458 (5)	N2B—C8B	1.455 (6)
N2A—C8A	1.459 (5)	C1B—C9B	1.514 (6)
C1A—C9A	1.507 (6)	C1B—H1C	0.9700
C1A—H1A	0.9700	C1B—H1D	0.9700
C1A—H1B	0.9700	C2B—C3B	1.345 (6)
C2A—C3A	1.347 (5)	C2B—H2B	0.9300
C2A—H2A	0.9300	C3B—C4B	1.405 (6)
C3A—C4A	1.428 (6)	C3B—H3B	0.9300
C3A—H3A	0.9300	C4B—C5B	1.399 (6)
C4A—C5A	1.403 (5)	C5B—C6B	1.349 (5)
C5A—C6A	1.345 (5)	C5B—H5B	0.9300
C5A—H5A	0.9300	C6B—H6B	0.9300
C6A—H6A	0.9300	C7B—H7D	0.9600
C7A—H7A	0.9600	C7B—H7E	0.9600
C7A—H7B	0.9600	C7B—H7F	0.9600
C7A—H7C	0.9600	C8B—H8D	0.9600
C8A—H8A	0.9600	C8B—H8E	0.9600
C8A—H8B	0.9600	C8B—H8F	0.9600
C8A—H8C	0.9600	C9B—C10B	1.477 (6)
C9A—C10A	1.481 (6)	C10B—C15B	1.378 (6)
C10A—C11A	1.386 (5)	C10B—C11B	1.384 (6)
C10A—C15A	1.392 (6)	C11B—C12B	1.371 (5)
C11A—C12A	1.375 (5)	C11B—H11B	0.9300
C11A—H11A	0.9300	C12B—C13B	1.389 (6)
C12A—C13A	1.390 (5)	C12B—H12B	0.9300
C12A—H12A	0.9300	C13B—C14B	1.391 (5)
C13A—C14A	1.403 (6)	C13B—C16B	1.484 (5)
C13A—C16A	1.493 (6)	C14B—C15B	1.374 (6)
C14A—C15A	1.370 (6)	C14B—H14B	0.9300
C14A—H14A	0.9300	C15B—H15B	0.9300
C15A—H15A	0.9300	C16B—C21B	1.391 (6)
C16A—C21A	1.380 (6)	C16B—C17B	1.393 (6)
C16A—C17A	1.394 (6)	C17B—C18B	1.381 (6)
C17A—C18A	1.380 (6)	C17B—H17B	0.9300
C17A—H17A	0.9300	C18B—C19B	1.367 (7)
C18A—C19A	1.362 (6)	C18B—H18B	0.9300
C18A—H18A	0.9300	C19B—C20B	1.371 (7)
C19A—C20A	1.376 (6)	C19B—H19B	0.9300
C19A—H19A	0.9300	C20B—C21B	1.362 (6)
C20A—C21A	1.388 (6)	C20B—H20B	0.9300
C20A—H20A	0.9300	C21B—H21B	0.9300
C21A—H21A	0.9300	OW—H22	0.86
O1B—C9B	1.204 (5)	OW—H23	0.87
C2A—N1A—C6A	117.7 (4)	C6B—N1B—C1B	120.6 (4)
C2A—N1A—C1A	121.6 (4)	C2B—N1B—C1B	121.0 (4)
C6A—N1A—C1A	120.7 (4)	C4B—N2B—C7B	122.2 (4)
C4A—N2A—C7A	122.4 (4)	C4B—N2B—C8B	122.0 (4)
C4A—N2A—C8A	121.2 (4)	C7B—N2B—C8B	115.7 (4)
C7A—N2A—C8A	116.4 (3)	N1B—C1B—C9B	111.3 (3)
N1A—C1A—C9A	113.1 (3)	N1B—C1B—H1C	109.4
N1A—C1A—H1A	109.0	C9B—C1B—H1C	109.4
C9A—C1A—H1A	109.0	N1B—C1B—H1D	109.4
N1A—C1A—H1B	109.0	C9B—C1B—H1D	109.4
C9A—C1A—H1B	109.0	H1C—C1B—H1D	108.0
H1A—C1A—H1B	107.8	C3B—C2B—N1B	122.4 (4)
C3A—C2A—N1A	122.7 (4)	C3B—C2B—H2B	118.8
C3A—C2A—H2A	118.6	N1B—C2B—H2B	118.8
N1A—C2A—H2A	118.6	C2B—C3B—C4B	120.7 (4)
C2A—C3A—C4A	120.8 (4)	C2B—C3B—H3B	119.6
C2A—C3A—H3A	119.6	C4B—C3B—H3B	119.6
C4A—C3A—H3A	119.6	N2B—C4B—C5B	122.4 (4)
N2A—C4A—C5A	123.2 (4)	N2B—C4B—C3B	122.1 (4)
N2A—C4A—C3A	122.3 (4)	C5B—C4B—C3B	115.5 (4)
C5A—C4A—C3A	114.6 (4)	C6B—C5B—C4B	121.0 (4)
C6A—C5A—C4A	121.7 (4)	C6B—C5B—H5B	119.5
C6A—C5A—H5A	119.1	C4B—C5B—H5B	119.5
C4A—C5A—H5A	119.1	N1B—C6B—C5B	122.0 (4)
C5A—C6A—N1A	122.3 (4)	N1B—C6B—H6B	119.0
C5A—C6A—H6A	118.8	C5B—C6B—H6B	119.0
N1A—C6A—H6A	118.8	N2B—C7B—H7D	109.5
N2A—C7A—H7A	109.5	N2B—C7B—H7E	109.5
N2A—C7A—H7B	109.5	H7D—C7B—H7E	109.5
H7A—C7A—H7B	109.5	N2B—C7B—H7F	109.5
N2A—C7A—H7C	109.5	H7D—C7B—H7F	109.5
H7A—C7A—H7C	109.5	H7E—C7B—H7F	109.5
H7B—C7A—H7C	109.5	N2B—C8B—H8D	109.5
N2A—C8A—H8A	109.5	N2B—C8B—H8E	109.5
N2A—C8A—H8B	109.5	H8D—C8B—H8E	109.5
H8A—C8A—H8B	109.5	N2B—C8B—H8F	109.5
N2A—C8A—H8C	109.5	H8D—C8B—H8F	109.5
H8A—C8A—H8C	109.5	H8E—C8B—H8F	109.5
H8B—C8A—H8C	109.5	O1B—C9B—C10B	122.6 (4)
O1A—C9A—C10A	121.9 (4)	O1B—C9B—C1B	119.5 (4)
O1A—C9A—C1A	120.0 (4)	C10B—C9B—C1B	117.9 (4)
C10A—C9A—C1A	118.1 (4)	C15B—C10B—C11B	118.0 (4)
C11A—C10A—C15A	118.0 (4)	C15B—C10B—C9B	119.1 (4)
C11A—C10A—C9A	122.7 (4)	C11B—C10B—C9B	122.9 (4)
C15A—C10A—C9A	119.3 (4)	C12B—C11B—C10B	120.9 (4)
C12A—C11A—C10A	121.0 (4)	C12B—C11B—H11B	119.5
C12A—C11A—H11A	119.5	C10B—C11B—H11B	119.5
C10A—C11A—H11A	119.5	C11B—C12B—C13B	121.8 (4)
C11A—C12A—C13A	121.6 (4)	C11B—C12B—H12B	119.1
C11A—C12A—H12A	119.2	C13B—C12B—H12B	119.1
C13A—C12A—H12A	119.2	C12B—C13B—C14B	116.4 (4)
C12A—C13A—C14A	117.1 (4)	C12B—C13B—C16B	122.3 (4)
C12A—C13A—C16A	121.2 (4)	C14B—C13B—C16B	121.2 (4)
C14A—C13A—C16A	121.7 (4)	C15B—C14B—C13B	121.9 (4)
C15A—C14A—C13A	121.3 (4)	C15B—C14B—H14B	119.0
C15A—C14A—H14A	119.4	C13B—C14B—H14B	119.0
C13A—C14A—H14A	119.4	C14B—C15B—C10B	120.8 (4)
C14A—C15A—C10A	121.1 (4)	C14B—C15B—H15B	119.6
C14A—C15A—H15A	119.5	C10B—C15B—H15B	119.6
C10A—C15A—H15A	119.5	C21B—C16B—C17B	117.0 (4)
C21A—C16A—C17A	116.9 (4)	C21B—C16B—C13B	121.9 (4)
C21A—C16A—C13A	121.5 (4)	C17B—C16B—C13B	121.0 (4)
C17A—C16A—C13A	121.5 (4)	C18B—C17B—C16B	120.9 (5)
C18A—C17A—C16A	121.9 (4)	C18B—C17B—H17B	119.5
C18A—C17A—H17A	119.1	C16B—C17B—H17B	119.5
C16A—C17A—H17A	119.1	C19B—C18B—C17B	120.3 (5)
C19A—C18A—C17A	120.1 (4)	C19B—C18B—H18B	119.8
C19A—C18A—H18A	119.9	C17B—C18B—H18B	119.8
C17A—C18A—H18A	119.9	C18B—C19B—C20B	119.5 (5)
C18A—C19A—C20A	119.5 (5)	C18B—C19B—H19B	120.2
C18A—C19A—H19A	120.2	C20B—C19B—H19B	120.2
C20A—C19A—H19A	120.2	C21B—C20B—C19B	120.6 (5)
C19A—C20A—C21A	120.3 (5)	C21B—C20B—H20B	119.7
C19A—C20A—H20A	119.9	C19B—C20B—H20B	119.7
C21A—C20A—H20A	119.9	C20B—C21B—C16B	121.6 (5)
C16A—C21A—C20A	121.3 (4)	C20B—C21B—H21B	119.2
C16A—C21A—H21A	119.3	C16B—C21B—H21B	119.2
C20A—C21A—H21A	119.3	H22—OW—H23	110
C6B—N1B—C2B	118.3 (3)
C2A—N1A—C1A—C9A	114.8 (4)	C6B—N1B—C1B—C9B	−90.6 (5)
C6A—N1A—C1A—C9A	−65.8 (5)	C2B—N1B—C1B—C9B	86.2 (5)
C6A—N1A—C2A—C3A	3.0 (6)	C6B—N1B—C2B—C3B	−1.7 (7)
C1A—N1A—C2A—C3A	−177.5 (4)	C1B—N1B—C2B—C3B	−178.5 (4)
N1A—C2A—C3A—C4A	0.2 (7)	N1B—C2B—C3B—C4B	0.6 (7)
C7A—N2A—C4A—C5A	−177.4 (4)	C7B—N2B—C4B—C5B	−178.4 (4)
C8A—N2A—C4A—C5A	0.0 (6)	C8B—N2B—C4B—C5B	−1.1 (7)
C7A—N2A—C4A—C3A	1.9 (6)	C7B—N2B—C4B—C3B	1.2 (7)
C8A—N2A—C4A—C3A	179.3 (4)	C8B—N2B—C4B—C3B	178.4 (4)
C2A—C3A—C4A—N2A	177.5 (4)	C2B—C3B—C4B—N2B	−178.8 (4)
C2A—C3A—C4A—C5A	−3.2 (6)	C2B—C3B—C4B—C5B	0.8 (7)
N2A—C4A—C5A—C6A	−177.6 (4)	N2B—C4B—C5B—C6B	178.5 (4)
C3A—C4A—C5A—C6A	3.0 (6)	C3B—C4B—C5B—C6B	−1.1 (6)
C4A—C5A—C6A—N1A	0.1 (7)	C2B—N1B—C6B—C5B	1.3 (6)
C2A—N1A—C6A—C5A	−3.2 (6)	C1B—N1B—C6B—C5B	178.2 (4)
C1A—N1A—C6A—C5A	177.4 (4)	C4B—C5B—C6B—N1B	0.1 (7)
N1A—C1A—C9A—O1A	4.5 (6)	N1B—C1B—C9B—O1B	2.2 (7)
N1A—C1A—C9A—C10A	−177.3 (3)	N1B—C1B—C9B—C10B	−178.5 (4)
O1A—C9A—C10A—C11A	−158.7 (4)	O1B—C9B—C10B—C15B	5.6 (8)
C1A—C9A—C10A—C11A	23.1 (6)	C1B—C9B—C10B—C15B	−173.8 (4)
O1A—C9A—C10A—C15A	19.7 (7)	O1B—C9B—C10B—C11B	−175.0 (5)
C1A—C9A—C10A—C15A	−158.5 (4)	C1B—C9B—C10B—C11B	5.7 (7)
C15A—C10A—C11A—C12A	0.4 (6)	C15B—C10B—C11B—C12B	−0.6 (7)
C9A—C10A—C11A—C12A	178.7 (4)	C9B—C10B—C11B—C12B	180.0 (4)
C10A—C11A—C12A—C13A	0.4 (7)	C10B—C11B—C12B—C13B	0.0 (7)
C11A—C12A—C13A—C14A	0.2 (6)	C11B—C12B—C13B—C14B	0.6 (6)
C11A—C12A—C13A—C16A	−179.6 (4)	C11B—C12B—C13B—C16B	179.6 (4)
C12A—C13A—C14A—C15A	−1.6 (6)	C12B—C13B—C14B—C15B	−0.6 (7)
C16A—C13A—C14A—C15A	178.2 (4)	C16B—C13B—C14B—C15B	−179.6 (4)
C13A—C14A—C15A—C10A	2.4 (7)	C13B—C14B—C15B—C10B	0.0 (7)
C11A—C10A—C15A—C14A	−1.8 (6)	C11B—C10B—C15B—C14B	0.5 (7)
C9A—C10A—C15A—C14A	179.8 (4)	C9B—C10B—C15B—C14B	−180.0 (4)
C12A—C13A—C16A—C21A	162.8 (4)	C12B—C13B—C16B—C21B	178.6 (4)
C14A—C13A—C16A—C21A	−16.9 (6)	C14B—C13B—C16B—C21B	−2.4 (6)
C12A—C13A—C16A—C17A	−15.1 (6)	C12B—C13B—C16B—C17B	−0.8 (6)
C14A—C13A—C16A—C17A	165.1 (4)	C14B—C13B—C16B—C17B	178.2 (4)
C21A—C16A—C17A—C18A	−0.1 (6)	C21B—C16B—C17B—C18B	0.3 (7)
C13A—C16A—C17A—C18A	178.0 (4)	C13B—C16B—C17B—C18B	179.7 (4)
C16A—C17A—C18A—C19A	0.2 (7)	C16B—C17B—C18B—C19B	0.7 (8)
C17A—C18A—C19A—C20A	0.3 (8)	C17B—C18B—C19B—C20B	−0.9 (8)
C18A—C19A—C20A—C21A	−1.0 (8)	C18B—C19B—C20B—C21B	0.2 (8)
C17A—C16A—C21A—C20A	−0.6 (7)	C19B—C20B—C21B—C16B	0.8 (8)
C13A—C16A—C21A—C20A	−178.7 (4)	C17B—C16B—C21B—C20B	−1.0 (7)
C19A—C20A—C21A—C16A	1.1 (8)	C13B—C16B—C21B—C20B	179.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1A···Br2	0.97	2.76	3.713 (5)	170
C2A—H2A···Br2	0.93	2.98	3.839 (4)	154
OW—H22···Br1	0.86	2.47	3.314 (4)	170
OW—H23···Br2	0.87	2.45	3.311 (4)	169
C1A—H1B···Br2^i	0.97	2.74	3.581 (5)	146
C7A—H7B···O1B^ii	0.96	2.76	3.650 (6)	155
C14A—H14A···OW^iii	0.93	2.61	3.530 (6)	173
C21A—H21A···OW^iii	0.93	2.62	3.500 (6)	157
C1B—H1D···Br1^iv	0.97	2.92	3.840 (5)	158
C8B—H8D···Br2^iv	0.96	2.80	3.680 (5)	153
C12B—H12B···Br1^v	0.93	2.99	3.874 (5)	159
C14B—H14B···OW^vi	0.93	2.38	3.270 (6)	160
C21B—H21B···OW^vi	0.93	2.85	3.774 (6)	174

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