Structure of a push–pull olefin prepared by ynamine hydro­boration with a borandiol ester

The title compound is a demonstration of hydro­boration of ynamines with borandiol ester. The bond lengths of the resulting push–pull olefin are discussed.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.086
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack parameter is too small
           From the CIF: _refine_ls_abs_structure_Flack   -0.700
           From the CIF: _refine_ls_abs_structure_Flack_su    0.400
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          6 Note

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.400 Report
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1A            105.5 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O2A            105.5 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O1B            105.3 Degree
PLAT395_ALERT_2_G Deviating  X-O-Y    Angle From 120 for O2B            105.4 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         12 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         26 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          8 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

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

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

---

Computing details

Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); 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).

N-[(Z)-2-(2H-1,3,2-Benzodioxaborol-2-yl)-2-phenylethenyl]-N-(propan-2-yl)aniline

Crystal data

C23H22BNO2	Dx = 1.236 Mg m^−3
Mr = 355.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 9981 reflections
a = 17.8540 (11) Å	θ = 2.5–26.8°
b = 11.5361 (6) Å	µ = 0.08 mm^−1
c = 18.5366 (12) Å	T = 100 K
V = 3817.9 (4) Å^3	Plate, clear light yellow
Z = 8	0.38 × 0.2 × 0.07 mm
F(000) = 1504

Data collection

Bruker–Nonius Kappa APEXII diffractometer	8781 independent reflections
Radiation source: sealed tube	7379 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 8.33 pixels mm^-1	θmax = 27.6°, θmin = 2.8°
ω and φ scans	h = −23→23
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −14→14
Tmin = 0.703, Tmax = 0.733	l = −24→24
60829 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0401P)^2 + 0.7053P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.086	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.25 e Å^−3
8781 reflections	Δρmin = −0.24 e Å^−3
491 parameters	Absolute structure: Flack x determined using 3185 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: −0.7 (4)
Primary atom site location: structure-invariant direct methods

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. 8 reflections were omitted (some are equivalents). These were checked visually and are all results of high background around the beamstop (beginning ice formation or crystalline powder covering the sample). 0 1 0 is clearly shadowed by the beamstop. Absolute structure is not claimed due to unreliable Flack and Hooft parameters.

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

	x	y	z	Uiso*/Ueq
O1B	0.18188 (9)	0.59842 (13)	0.60028 (9)	0.0155 (4)
O2B	0.30086 (9)	0.67252 (13)	0.61169 (9)	0.0158 (4)
N1B	0.23745 (11)	0.25154 (16)	0.65127 (11)	0.0159 (4)
C1B	0.10503 (15)	0.2002 (2)	0.62440 (14)	0.0210 (6)
H1BA	0.0874	0.2806	0.6251	0.032*
H1BB	0.0642	0.1485	0.6390	0.032*
H1BC	0.1215	0.1800	0.5756	0.032*
C2B	0.14877 (15)	0.2209 (2)	0.75303 (14)	0.0205 (6)
H2BA	0.1928	0.2152	0.7844	0.031*
H2BB	0.1096	0.1686	0.7707	0.031*
H2BC	0.1301	0.3008	0.7533	0.031*
C3B	0.17032 (14)	0.1869 (2)	0.67659 (13)	0.0160 (5)
H3B	0.1840	0.1028	0.6776	0.019*
C4B	0.30570 (13)	0.18933 (19)	0.64199 (14)	0.0147 (5)
C5B	0.32986 (14)	0.1121 (2)	0.69452 (14)	0.0189 (5)
H5B	0.3009	0.1007	0.7369	0.023*
C6B	0.39606 (14)	0.0518 (2)	0.68521 (16)	0.0230 (6)
H6B	0.4126	−0.0006	0.7214	0.028*
C7B	0.43822 (15)	0.0673 (2)	0.62365 (16)	0.0275 (6)
H7B	0.4841	0.0267	0.6177	0.033*
C8B	0.41341 (15)	0.1423 (2)	0.57066 (15)	0.0238 (6)
H8B	0.4420	0.1522	0.5279	0.029*
C9B	0.34704 (14)	0.2033 (2)	0.57938 (14)	0.0191 (5)
H9B	0.3301	0.2543	0.5426	0.023*
C10B	0.23179 (13)	0.36795 (19)	0.63924 (13)	0.0151 (5)
H10B	0.1820	0.3949	0.6321	0.018*
C11B	0.28538 (13)	0.4526 (2)	0.63563 (13)	0.0156 (5)
C12B	0.36555 (13)	0.4370 (2)	0.65557 (13)	0.0142 (5)
C13B	0.38562 (14)	0.3878 (2)	0.72178 (13)	0.0172 (5)
H13B	0.3476	0.3630	0.7541	0.021*
C14B	0.46041 (15)	0.3748 (2)	0.74087 (14)	0.0209 (5)
H14B	0.4731	0.3410	0.7860	0.025*
C15B	0.51658 (14)	0.4110 (2)	0.69433 (14)	0.0210 (6)
H15B	0.5677	0.4012	0.7071	0.025*
C16B	0.49740 (14)	0.4614 (2)	0.62906 (14)	0.0188 (5)
H16B	0.5356	0.4869	0.5972	0.023*
C17B	0.42288 (14)	0.4749 (2)	0.60995 (14)	0.0169 (5)
H17B	0.4106	0.5103	0.5652	0.020*
C18B	0.18063 (14)	0.71629 (19)	0.58605 (13)	0.0140 (5)
C19B	0.12056 (14)	0.7829 (2)	0.56544 (13)	0.0178 (5)
H19B	0.0715	0.7518	0.5614	0.021*
C20B	0.13606 (15)	0.8997 (2)	0.55079 (14)	0.0198 (5)
H20B	0.0966	0.9492	0.5356	0.024*
C21B	0.20801 (15)	0.9445 (2)	0.55794 (13)	0.0192 (5)
H21B	0.2165	1.0242	0.5478	0.023*
C22B	0.26793 (14)	0.8754 (2)	0.57958 (13)	0.0179 (5)
H22B	0.3171	0.9059	0.5849	0.022*
C23B	0.25211 (13)	0.76087 (19)	0.59287 (13)	0.0151 (5)
B1B	0.25681 (15)	0.5724 (2)	0.61526 (14)	0.0149 (6)
O1A	0.59813 (9)	−0.09865 (13)	0.40292 (10)	0.0176 (4)
O2A	0.71747 (9)	−0.17253 (13)	0.39845 (9)	0.0174 (4)
N1A	0.65302 (11)	0.24387 (17)	0.34366 (11)	0.0161 (4)
C1A	0.52189 (14)	0.2942 (2)	0.37802 (15)	0.0228 (6)
H1AA	0.5416	0.3104	0.4263	0.034*
H1AB	0.5027	0.2146	0.3764	0.034*
H1AC	0.4813	0.3485	0.3671	0.034*
C2A	0.58421 (14)	0.3081 (2)	0.32256 (14)	0.0177 (5)
H2A	0.5976	0.3923	0.3213	0.021*
C3A	0.55869 (14)	0.2754 (2)	0.24731 (15)	0.0227 (6)
H3AA	0.5407	0.1952	0.2473	0.034*
H3AB	0.6008	0.2829	0.2137	0.034*
H3AC	0.5180	0.3272	0.2323	0.034*
C4A	0.72025 (13)	0.3083 (2)	0.35237 (13)	0.0139 (5)
C5A	0.76423 (13)	0.2910 (2)	0.41332 (13)	0.0150 (5)
H5A	0.7496	0.2358	0.4487	0.018*
C6A	0.82952 (14)	0.3543 (2)	0.42245 (14)	0.0199 (5)
H6A	0.8596	0.3423	0.4640	0.024*
C7A	0.85112 (15)	0.4353 (2)	0.37098 (15)	0.0233 (6)
H7A	0.8964	0.4776	0.3768	0.028*
C8A	0.80630 (14)	0.4541 (2)	0.31124 (16)	0.0227 (6)
H8A	0.8204	0.5105	0.2765	0.027*
C9A	0.74113 (14)	0.3912 (2)	0.30178 (14)	0.0182 (5)
H9A	0.7106	0.4047	0.2607	0.022*
C10A	0.64818 (14)	0.1276 (2)	0.35658 (13)	0.0157 (5)
H10A	0.5984	0.1001	0.3624	0.019*
C11A	0.70180 (13)	0.0433 (2)	0.36266 (12)	0.0136 (5)
C12A	0.78275 (13)	0.0582 (2)	0.34518 (13)	0.0143 (5)
C13A	0.83799 (13)	0.0207 (2)	0.39292 (13)	0.0159 (5)
H13A	0.8239	−0.0154	0.4369	0.019*
C14A	0.91359 (14)	0.0353 (2)	0.37700 (15)	0.0184 (5)
H14A	0.9505	0.0104	0.4105	0.022*
C15A	0.93517 (15)	0.0860 (2)	0.31277 (14)	0.0209 (6)
H15A	0.9868	0.0967	0.3021	0.025*
C16A	0.88076 (14)	0.1212 (2)	0.26390 (14)	0.0209 (6)
H16A	0.8952	0.1549	0.2193	0.025*
C17A	0.80555 (14)	0.1074 (2)	0.27994 (13)	0.0166 (5)
H17A	0.7689	0.1317	0.2460	0.020*
C18A	0.59638 (14)	−0.2147 (2)	0.42114 (13)	0.0155 (5)
C19A	0.53579 (14)	−0.2820 (2)	0.43916 (14)	0.0196 (5)
H19A	0.4864	−0.2514	0.4402	0.024*
C20A	0.55064 (15)	−0.3974 (2)	0.45574 (14)	0.0212 (6)
H20A	0.5102	−0.4469	0.4685	0.025*
C21A	0.62240 (15)	−0.4420 (2)	0.45425 (14)	0.0221 (6)
H21A	0.6302	−0.5212	0.4661	0.027*
C22A	0.68384 (15)	−0.3727 (2)	0.43561 (14)	0.0215 (6)
H22A	0.7335	−0.4024	0.4346	0.026*
C23A	0.66814 (14)	−0.2591 (2)	0.41882 (13)	0.0159 (5)
B1A	0.67343 (15)	−0.0740 (2)	0.38806 (15)	0.0149 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1B	0.0139 (8)	0.0119 (8)	0.0206 (9)	0.0005 (7)	0.0001 (7)	0.0023 (7)
O2B	0.0137 (8)	0.0144 (8)	0.0194 (9)	−0.0010 (6)	−0.0018 (7)	0.0016 (7)
N1B	0.0115 (10)	0.0142 (9)	0.0218 (11)	0.0004 (8)	0.0030 (8)	0.0028 (8)
C1B	0.0183 (13)	0.0203 (12)	0.0245 (15)	−0.0017 (10)	−0.0016 (11)	−0.0009 (11)
C2B	0.0194 (14)	0.0215 (13)	0.0206 (13)	−0.0021 (11)	0.0031 (11)	0.0012 (10)
C3B	0.0142 (13)	0.0135 (11)	0.0205 (13)	−0.0017 (10)	0.0030 (10)	0.0013 (10)
C4B	0.0115 (12)	0.0112 (10)	0.0213 (13)	−0.0010 (9)	−0.0012 (10)	−0.0023 (10)
C5B	0.0187 (13)	0.0162 (12)	0.0218 (14)	−0.0021 (10)	−0.0029 (10)	0.0006 (10)
C6B	0.0174 (13)	0.0157 (12)	0.0360 (16)	0.0007 (10)	−0.0082 (12)	0.0023 (11)
C7B	0.0144 (13)	0.0196 (12)	0.0487 (19)	0.0027 (11)	0.0015 (13)	−0.0046 (12)
C8B	0.0196 (14)	0.0191 (13)	0.0328 (16)	−0.0020 (11)	0.0108 (11)	−0.0065 (11)
C9B	0.0173 (13)	0.0168 (12)	0.0232 (13)	−0.0015 (10)	0.0015 (10)	−0.0014 (10)
C10B	0.0132 (12)	0.0174 (11)	0.0147 (11)	0.0022 (9)	0.0007 (9)	0.0013 (10)
C11B	0.0146 (12)	0.0169 (11)	0.0152 (12)	0.0014 (10)	0.0027 (10)	0.0006 (10)
C12B	0.0133 (12)	0.0120 (11)	0.0173 (12)	0.0018 (9)	0.0002 (10)	−0.0012 (10)
C13B	0.0182 (13)	0.0161 (12)	0.0172 (13)	0.0000 (10)	0.0021 (10)	−0.0014 (10)
C14B	0.0217 (14)	0.0217 (13)	0.0195 (13)	0.0023 (11)	−0.0053 (11)	0.0007 (11)
C15B	0.0143 (13)	0.0208 (12)	0.0281 (15)	0.0023 (10)	−0.0057 (11)	−0.0022 (11)
C16B	0.0144 (12)	0.0178 (12)	0.0244 (14)	−0.0007 (10)	0.0032 (10)	−0.0005 (10)
C17B	0.0177 (12)	0.0163 (11)	0.0169 (12)	0.0007 (10)	0.0008 (10)	0.0008 (10)
C18B	0.0171 (12)	0.0124 (11)	0.0124 (11)	−0.0024 (10)	0.0031 (9)	0.0000 (9)
C19B	0.0140 (13)	0.0202 (13)	0.0191 (13)	0.0031 (10)	0.0011 (10)	0.0001 (10)
C20B	0.0236 (14)	0.0186 (12)	0.0171 (13)	0.0061 (11)	0.0014 (11)	0.0014 (10)
C21B	0.0277 (14)	0.0125 (11)	0.0172 (13)	0.0003 (11)	0.0044 (11)	−0.0002 (10)
C22B	0.0217 (13)	0.0174 (11)	0.0147 (12)	−0.0032 (10)	0.0000 (10)	−0.0025 (9)
C23B	0.0158 (12)	0.0167 (11)	0.0127 (11)	0.0028 (10)	−0.0025 (9)	−0.0023 (10)
B1B	0.0128 (13)	0.0191 (13)	0.0129 (13)	−0.0004 (11)	0.0016 (11)	−0.0006 (11)
O1A	0.0134 (9)	0.0138 (8)	0.0258 (10)	−0.0012 (7)	0.0003 (7)	0.0027 (7)
O2A	0.0139 (9)	0.0146 (8)	0.0237 (10)	−0.0005 (7)	0.0028 (7)	0.0023 (7)
N1A	0.0116 (10)	0.0147 (10)	0.0220 (11)	0.0002 (8)	−0.0036 (8)	0.0030 (8)
C1A	0.0161 (13)	0.0221 (13)	0.0304 (15)	0.0042 (11)	0.0001 (11)	0.0005 (12)
C2A	0.0128 (12)	0.0150 (11)	0.0251 (14)	0.0015 (10)	−0.0032 (10)	0.0033 (10)
C3A	0.0154 (14)	0.0273 (14)	0.0254 (14)	0.0027 (11)	−0.0061 (11)	0.0047 (11)
C4A	0.0121 (12)	0.0119 (11)	0.0175 (12)	0.0009 (9)	0.0005 (10)	−0.0018 (9)
C5A	0.0157 (12)	0.0142 (10)	0.0151 (12)	0.0010 (9)	0.0010 (10)	−0.0004 (9)
C6A	0.0160 (12)	0.0214 (12)	0.0223 (14)	0.0021 (10)	−0.0038 (10)	−0.0035 (11)
C7A	0.0155 (13)	0.0179 (12)	0.0366 (16)	−0.0054 (11)	0.0001 (12)	−0.0006 (11)
C8A	0.0198 (14)	0.0182 (12)	0.0300 (15)	−0.0014 (11)	0.0034 (11)	0.0066 (11)
C9A	0.0175 (13)	0.0173 (12)	0.0198 (13)	0.0018 (10)	−0.0009 (10)	0.0033 (10)
C10A	0.0129 (12)	0.0171 (12)	0.0172 (12)	−0.0036 (10)	−0.0012 (9)	0.0010 (10)
C11A	0.0125 (12)	0.0146 (11)	0.0138 (12)	0.0000 (9)	−0.0014 (9)	0.0005 (9)
C12A	0.0143 (12)	0.0123 (11)	0.0164 (12)	−0.0009 (9)	0.0007 (10)	−0.0042 (10)
C13A	0.0162 (12)	0.0143 (11)	0.0170 (13)	0.0002 (10)	0.0011 (10)	0.0002 (10)
C14A	0.0140 (12)	0.0166 (12)	0.0247 (14)	0.0000 (10)	−0.0032 (10)	−0.0033 (10)
C15A	0.0152 (13)	0.0220 (12)	0.0255 (14)	−0.0017 (10)	0.0056 (11)	−0.0028 (11)
C16A	0.0229 (14)	0.0215 (13)	0.0182 (13)	−0.0034 (11)	0.0064 (11)	0.0000 (11)
C17A	0.0165 (12)	0.0167 (12)	0.0166 (12)	−0.0003 (10)	−0.0014 (10)	−0.0008 (10)
C18A	0.0185 (13)	0.0154 (11)	0.0127 (12)	−0.0018 (10)	−0.0012 (9)	0.0004 (9)
C19A	0.0151 (13)	0.0228 (13)	0.0211 (13)	−0.0022 (11)	−0.0002 (10)	0.0028 (11)
C20A	0.0236 (14)	0.0209 (13)	0.0190 (13)	−0.0103 (11)	−0.0021 (11)	0.0036 (10)
C21A	0.0294 (15)	0.0155 (12)	0.0215 (13)	−0.0025 (11)	−0.0005 (11)	0.0047 (10)
C22A	0.0216 (14)	0.0191 (12)	0.0237 (14)	0.0030 (11)	−0.0002 (11)	0.0019 (11)
C23A	0.0137 (12)	0.0178 (12)	0.0164 (12)	−0.0037 (10)	0.0009 (10)	0.0009 (10)
B1A	0.0126 (13)	0.0177 (13)	0.0143 (13)	−0.0006 (11)	0.0002 (11)	−0.0026 (11)

Geometric parameters (Å, º)

O1B—C18B	1.385 (3)	O1A—C18A	1.382 (3)
O1B—B1B	1.399 (3)	O1A—B1A	1.402 (3)
O2B—C23B	1.385 (3)	O2A—C23A	1.384 (3)
O2B—B1B	1.398 (3)	O2A—B1A	1.396 (3)
N1B—C3B	1.488 (3)	N1A—C2A	1.487 (3)
N1B—C4B	1.425 (3)	N1A—C4A	1.421 (3)
N1B—C10B	1.365 (3)	N1A—C10A	1.365 (3)
C1B—H1BA	0.9800	C1A—H1AA	0.9800
C1B—H1BB	0.9800	C1A—H1AB	0.9800
C1B—H1BC	0.9800	C1A—H1AC	0.9800
C1B—C3B	1.523 (4)	C1A—C2A	1.523 (4)
C2B—H2BA	0.9800	C2A—H2A	1.0000
C2B—H2BB	0.9800	C2A—C3A	1.515 (4)
C2B—H2BC	0.9800	C3A—H3AA	0.9800
C2B—C3B	1.520 (3)	C3A—H3AB	0.9800
C3B—H3B	1.0000	C3A—H3AC	0.9800
C4B—C5B	1.389 (3)	C4A—C5A	1.390 (3)
C4B—C9B	1.385 (4)	C4A—C9A	1.390 (3)
C5B—H5B	0.9500	C5A—H5A	0.9500
C5B—C6B	1.382 (3)	C5A—C6A	1.386 (3)
C6B—H6B	0.9500	C6A—H6A	0.9500
C6B—C7B	1.379 (4)	C6A—C7A	1.390 (4)
C7B—H7B	0.9500	C7A—H7A	0.9500
C7B—C8B	1.382 (4)	C7A—C8A	1.383 (4)
C8B—H8B	0.9500	C8A—H8A	0.9500
C8B—C9B	1.387 (4)	C8A—C9A	1.382 (4)
C9B—H9B	0.9500	C9A—H9A	0.9500
C10B—H10B	0.9500	C10A—H10A	0.9500
C10B—C11B	1.369 (3)	C10A—C11A	1.370 (3)
C11B—C12B	1.489 (3)	C11A—C12A	1.491 (3)
C11B—B1B	1.521 (4)	C11A—B1A	1.519 (3)
C12B—C13B	1.399 (3)	C12A—C13A	1.394 (3)
C12B—C17B	1.398 (3)	C12A—C17A	1.397 (3)
C13B—H13B	0.9500	C13A—H13A	0.9500
C13B—C14B	1.389 (4)	C13A—C14A	1.392 (3)
C14B—H14B	0.9500	C14A—H14A	0.9500
C14B—C15B	1.387 (4)	C14A—C15A	1.381 (4)
C15B—H15B	0.9500	C15A—H15A	0.9500
C15B—C16B	1.385 (4)	C15A—C16A	1.389 (4)
C16B—H16B	0.9500	C16A—H16A	0.9500
C16B—C17B	1.386 (3)	C16A—C17A	1.385 (3)
C17B—H17B	0.9500	C17A—H17A	0.9500
C18B—C19B	1.374 (3)	C18A—C19A	1.372 (3)
C18B—C23B	1.382 (3)	C18A—C23A	1.381 (3)
C19B—H19B	0.9500	C19A—H19A	0.9500
C19B—C20B	1.401 (3)	C20A—H20A	0.9500
C20B—H20B	0.9500	C20A—C21A	1.381 (4)
C20B—C21B	1.391 (4)	C21A—H21A	0.9500
C21B—H21B	0.9500	C21A—C22A	1.401 (4)
C21B—C22B	1.393 (4)	C22A—H22A	0.9500
C22B—H22B	0.9500	C22A—C23A	1.375 (3)
C22B—C23B	1.374 (3)
C18B—O1B—B1B	105.28 (18)	C18A—O1A—B1A	105.46 (18)
C23B—O2B—B1B	105.43 (18)	C23A—O2A—B1A	105.50 (18)
C4B—N1B—C3B	118.34 (18)	C4A—N1A—C2A	117.83 (18)
C10B—N1B—C3B	119.02 (19)	C10A—N1A—C2A	118.9 (2)
C10B—N1B—C4B	122.6 (2)	C10A—N1A—C4A	123.2 (2)
H1BA—C1B—H1BB	109.5	H1AA—C1A—H1AB	109.5
H1BA—C1B—H1BC	109.5	H1AA—C1A—H1AC	109.5
H1BB—C1B—H1BC	109.5	H1AB—C1A—H1AC	109.5
C3B—C1B—H1BA	109.5	C2A—C1A—H1AA	109.5
C3B—C1B—H1BB	109.5	C2A—C1A—H1AB	109.5
C3B—C1B—H1BC	109.5	C2A—C1A—H1AC	109.5
H2BA—C2B—H2BB	109.5	N1A—C2A—C1A	111.9 (2)
H2BA—C2B—H2BC	109.5	N1A—C2A—H2A	107.0
H2BB—C2B—H2BC	109.5	N1A—C2A—C3A	111.5 (2)
C3B—C2B—H2BA	109.5	C1A—C2A—H2A	107.0
C3B—C2B—H2BB	109.5	C3A—C2A—C1A	112.1 (2)
C3B—C2B—H2BC	109.5	C3A—C2A—H2A	107.0
N1B—C3B—C1B	111.5 (2)	C2A—C3A—H3AA	109.5
N1B—C3B—C2B	111.6 (2)	C2A—C3A—H3AB	109.5
N1B—C3B—H3B	107.2	C2A—C3A—H3AC	109.5
C1B—C3B—H3B	107.2	H3AA—C3A—H3AB	109.5
C2B—C3B—C1B	111.9 (2)	H3AA—C3A—H3AC	109.5
C2B—C3B—H3B	107.2	H3AB—C3A—H3AC	109.5
C5B—C4B—N1B	120.3 (2)	C5A—C4A—N1A	119.6 (2)
C9B—C4B—N1B	119.9 (2)	C5A—C4A—C9A	119.7 (2)
C9B—C4B—C5B	119.8 (2)	C9A—C4A—N1A	120.6 (2)
C4B—C5B—H5B	120.0	C4A—C5A—H5A	120.1
C6B—C5B—C4B	120.1 (2)	C6A—C5A—C4A	119.9 (2)
C6B—C5B—H5B	120.0	C6A—C5A—H5A	120.1
C5B—C6B—H6B	119.8	C5A—C6A—H6A	119.9
C7B—C6B—C5B	120.3 (2)	C5A—C6A—C7A	120.3 (2)
C7B—C6B—H6B	119.8	C7A—C6A—H6A	119.9
C6B—C7B—H7B	120.2	C6A—C7A—H7A	120.2
C6B—C7B—C8B	119.7 (2)	C8A—C7A—C6A	119.6 (2)
C8B—C7B—H7B	120.2	C8A—C7A—H7A	120.2
C7B—C8B—H8B	119.7	C7A—C8A—H8A	119.8
C7B—C8B—C9B	120.5 (2)	C9A—C8A—C7A	120.4 (2)
C9B—C8B—H8B	119.7	C9A—C8A—H8A	119.8
C4B—C9B—C8B	119.6 (2)	C4A—C9A—H9A	120.0
C4B—C9B—H9B	120.2	C8A—C9A—C4A	120.1 (2)
C8B—C9B—H9B	120.2	C8A—C9A—H9A	120.0
N1B—C10B—H10B	114.4	N1A—C10A—H10A	114.0
N1B—C10B—C11B	131.2 (2)	N1A—C10A—C11A	131.9 (2)
C11B—C10B—H10B	114.4	C11A—C10A—H10A	114.0
C10B—C11B—C12B	125.0 (2)	C10A—C11A—C12A	125.3 (2)
C10B—C11B—B1B	115.2 (2)	C10A—C11A—B1A	115.1 (2)
C12B—C11B—B1B	119.6 (2)	C12A—C11A—B1A	119.5 (2)
C13B—C12B—C11B	120.9 (2)	C13A—C12A—C11A	120.8 (2)
C17B—C12B—C11B	121.1 (2)	C13A—C12A—C17A	118.0 (2)
C17B—C12B—C13B	118.0 (2)	C17A—C12A—C11A	121.2 (2)
C12B—C13B—H13B	119.6	C12A—C13A—H13A	119.5
C14B—C13B—C12B	120.9 (2)	C14A—C13A—C12A	120.9 (2)
C14B—C13B—H13B	119.6	C14A—C13A—H13A	119.5
C13B—C14B—H14B	119.9	C13A—C14A—H14A	119.8
C15B—C14B—C13B	120.3 (2)	C15A—C14A—C13A	120.3 (2)
C15B—C14B—H14B	119.9	C15A—C14A—H14A	119.8
C14B—C15B—H15B	120.3	C14A—C15A—H15A	120.3
C16B—C15B—C14B	119.4 (2)	C14A—C15A—C16A	119.4 (2)
C16B—C15B—H15B	120.3	C16A—C15A—H15A	120.3
C15B—C16B—H16B	119.7	C15A—C16A—H16A	119.9
C15B—C16B—C17B	120.5 (2)	C17A—C16A—C15A	120.3 (2)
C17B—C16B—H16B	119.7	C17A—C16A—H16A	119.9
C12B—C17B—H17B	119.5	C12A—C17A—H17A	119.5
C16B—C17B—C12B	120.9 (2)	C16A—C17A—C12A	121.0 (2)
C16B—C17B—H17B	119.5	C16A—C17A—H17A	119.5
C19B—C18B—O1B	127.9 (2)	C19A—C18A—O1A	128.7 (2)
C19B—C18B—C23B	122.6 (2)	C19A—C18A—C23A	122.0 (2)
C23B—C18B—O1B	109.4 (2)	C23A—C18A—O1A	109.3 (2)
C18B—C19B—H19B	122.0	C18A—C19A—H19A	121.8
C18B—C19B—C20B	115.9 (2)	C18A—C19A—C20A	116.4 (2)
C20B—C19B—H19B	122.0	C20A—C19A—H19A	121.8
C19B—C20B—H20B	119.3	C19A—C20A—H20A	119.0
C21B—C20B—C19B	121.4 (2)	C21A—C20A—C19A	121.9 (2)
C21B—C20B—H20B	119.3	C21A—C20A—H20A	119.0
C20B—C21B—H21B	119.2	C20A—C21A—H21A	119.4
C20B—C21B—C22B	121.6 (2)	C20A—C21A—C22A	121.3 (2)
C22B—C21B—H21B	119.2	C22A—C21A—H21A	119.4
C21B—C22B—H22B	121.8	C21A—C22A—H22A	122.0
C23B—C22B—C21B	116.4 (2)	C23A—C22A—C21A	116.1 (2)
C23B—C22B—H22B	121.8	C23A—C22A—H22A	122.0
C18B—C23B—O2B	109.24 (19)	C18A—C23A—O2A	109.3 (2)
C22B—C23B—O2B	128.6 (2)	C22A—C23A—O2A	128.3 (2)
C22B—C23B—C18B	122.1 (2)	C22A—C23A—C18A	122.4 (2)
O1B—B1B—C11B	124.4 (2)	O1A—B1A—C11A	124.2 (2)
O2B—B1B—O1B	110.6 (2)	O2A—B1A—O1A	110.4 (2)
O2B—B1B—C11B	125.0 (2)	O2A—B1A—C11A	125.5 (2)
O1B—C18B—C19B—C20B	−176.7 (2)	O1A—C18A—C19A—C20A	−179.5 (2)
O1B—C18B—C23B—O2B	0.0 (3)	O1A—C18A—C23A—O2A	−0.5 (3)
O1B—C18B—C23B—C22B	177.9 (2)	O1A—C18A—C23A—C22A	178.9 (2)
N1B—C4B—C5B—C6B	179.9 (2)	N1A—C4A—C5A—C6A	−179.4 (2)
N1B—C4B—C9B—C8B	−179.9 (2)	N1A—C4A—C9A—C8A	179.4 (2)
N1B—C10B—C11B—C12B	−9.7 (4)	N1A—C10A—C11A—C12A	−9.7 (4)
N1B—C10B—C11B—B1B	175.5 (2)	N1A—C10A—C11A—B1A	171.6 (2)
C3B—N1B—C4B—C5B	−45.6 (3)	C2A—N1A—C4A—C5A	132.7 (2)
C3B—N1B—C4B—C9B	132.5 (2)	C2A—N1A—C4A—C9A	−45.1 (3)
C3B—N1B—C10B—C11B	159.6 (3)	C2A—N1A—C10A—C11A	165.3 (2)
C4B—N1B—C3B—C1B	−123.7 (2)	C4A—N1A—C2A—C1A	−120.9 (2)
C4B—N1B—C3B—C2B	110.3 (2)	C4A—N1A—C2A—C3A	112.7 (2)
C4B—N1B—C10B—C11B	−19.1 (4)	C4A—N1A—C10A—C11A	−17.5 (4)
C4B—C5B—C6B—C7B	−0.4 (4)	C4A—C5A—C6A—C7A	0.1 (4)
C5B—C4B—C9B—C8B	−1.8 (4)	C5A—C4A—C9A—C8A	1.6 (4)
C5B—C6B—C7B—C8B	−1.0 (4)	C5A—C6A—C7A—C8A	1.3 (4)
C6B—C7B—C8B—C9B	1.0 (4)	C6A—C7A—C8A—C9A	−1.3 (4)
C7B—C8B—C9B—C4B	0.5 (4)	C7A—C8A—C9A—C4A	−0.1 (4)
C9B—C4B—C5B—C6B	1.8 (4)	C9A—C4A—C5A—C6A	−1.6 (4)
C10B—N1B—C3B—C1B	57.5 (3)	C10A—N1A—C2A—C1A	56.4 (3)
C10B—N1B—C3B—C2B	−68.4 (3)	C10A—N1A—C2A—C3A	−69.9 (3)
C10B—N1B—C4B—C5B	133.1 (2)	C10A—N1A—C4A—C5A	−44.5 (3)
C10B—N1B—C4B—C9B	−48.8 (3)	C10A—N1A—C4A—C9A	137.6 (2)
C10B—C11B—C12B—C13B	−50.5 (3)	C10A—C11A—C12A—C13A	132.2 (3)
C10B—C11B—C12B—C17B	131.9 (3)	C10A—C11A—C12A—C17A	−49.3 (3)
C10B—C11B—B1B—O1B	−0.5 (4)	C10A—C11A—B1A—O1A	1.7 (4)
C10B—C11B—B1B—O2B	176.9 (2)	C10A—C11A—B1A—O2A	−179.8 (2)
C11B—C12B—C13B—C14B	−179.0 (2)	C11A—C12A—C13A—C14A	−179.5 (2)
C11B—C12B—C17B—C16B	179.3 (2)	C11A—C12A—C17A—C16A	179.9 (2)
C12B—C11B—B1B—O1B	−175.6 (2)	C12A—C11A—B1A—O1A	−177.2 (2)
C12B—C11B—B1B—O2B	1.7 (4)	C12A—C11A—B1A—O2A	1.4 (4)
C12B—C13B—C14B—C15B	0.2 (4)	C12A—C13A—C14A—C15A	−1.0 (4)
C13B—C12B—C17B—C16B	1.6 (3)	C13A—C12A—C17A—C16A	−1.6 (3)
C13B—C14B—C15B—C16B	0.8 (4)	C13A—C14A—C15A—C16A	−0.6 (4)
C14B—C15B—C16B—C17B	−0.5 (4)	C14A—C15A—C16A—C17A	1.1 (4)
C15B—C16B—C17B—C12B	−0.6 (4)	C15A—C16A—C17A—C12A	0.1 (4)
C17B—C12B—C13B—C14B	−1.3 (3)	C17A—C12A—C13A—C14A	2.0 (3)
C18B—O1B—B1B—O2B	1.1 (3)	C18A—O1A—B1A—O2A	−1.2 (3)
C18B—O1B—B1B—C11B	178.7 (2)	C18A—O1A—B1A—C11A	177.5 (2)
C18B—C19B—C20B—C21B	−0.9 (4)	C18A—C19A—C20A—C21A	0.1 (4)
C19B—C18B—C23B—O2B	−177.8 (2)	C19A—C18A—C23A—O2A	179.4 (2)
C19B—C18B—C23B—C22B	0.1 (4)	C19A—C18A—C23A—C22A	−1.2 (4)
C19B—C20B—C21B—C22B	0.3 (4)	C19A—C20A—C21A—C22A	−0.2 (4)
C20B—C21B—C22B—C23B	0.5 (4)	C20A—C21A—C22A—C23A	−0.3 (4)
C21B—C22B—C23B—O2B	176.8 (2)	C21A—C22A—C23A—O2A	−179.7 (2)
C21B—C22B—C23B—C18B	−0.7 (4)	C21A—C22A—C23A—C18A	1.0 (4)
C23B—O2B—B1B—O1B	−1.1 (3)	C23A—O2A—B1A—O1A	1.0 (3)
C23B—O2B—B1B—C11B	−178.7 (2)	C23A—O2A—B1A—C11A	−177.8 (2)
C23B—C18B—C19B—C20B	0.7 (4)	C23A—C18A—C19A—C20A	0.6 (4)
B1B—O1B—C18B—C19B	177.0 (2)	B1A—O1A—C18A—C19A	−178.8 (3)
B1B—O1B—C18B—C23B	−0.6 (3)	B1A—O1A—C18A—C23A	1.0 (3)
B1B—O2B—C23B—C18B	0.7 (3)	B1A—O2A—C23A—C18A	−0.3 (3)
B1B—O2B—C23B—C22B	−177.1 (2)	B1A—O2A—C23A—C22A	−179.7 (3)
B1B—C11B—C12B—C13B	124.1 (3)	B1A—C11A—C12A—C13A	−49.1 (3)
B1B—C11B—C12B—C17B	−53.5 (3)	B1A—C11A—C12A—C17A	129.4 (2)