7β-Chloro-6,14-endo-etheno-6,7,8,14-tetra­hydro­thebaine

In the crystal structure of the title compound, C₂₁H₂₄ClNO₃, there are two independent mol­ecules in the asymmetric unit. The compound is the product of a new procedure for preparing Diels–Alder adducts of thebaine with 7β substit­uents.

Key indicators

• Single-crystal X-ray study
• T = 103 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.121
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.97 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.48 Ratio

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.66 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    Cl7'   -   C7'     ..       5.18 su
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         21

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.35
           From the CIF: _reflns_number_total               8828
           Count of symmetry unique reflns         5073
           Completeness (_total/calc)            174.02%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3755
           Fraction of Friedel pairs measured     0.740
           Are heavy atom types Z>Si present          yes

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

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

---

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2000) and XPREP (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(3)

Crystal data

C21H24ClNO3	F(000) = 1584
Mr = 373.86	Dx = 1.372 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7584 reflections
a = 7.7262 (4) Å	θ = 2.7–26.7°
b = 19.8316 (10) Å	µ = 0.23 mm^−1
c = 23.6182 (13) Å	T = 103 K
V = 3618.8 (3) Å^3	Plate, colorless
Z = 8	0.35 × 0.23 × 0.02 mm

Data collection

Bruker SMART 1000 CCD diffractometer	8828 independent reflections
Radiation source: sealed tube	5974 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
φ and ω scans	θmax = 28.4°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.839, Tmax = 0.995	k = −26→26
29542 measured reflections	l = −28→30

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0274P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.23	(Δ/σ)max < 0.001
8828 reflections	Δρmax = 0.29 e Å^−3
475 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Absolute structure: Flack (1983), 3864 Friedels
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (6)

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
C1	0.3453 (4)	1.01205 (14)	0.26310 (13)	0.0214 (7)
H1A	0.2312	1.0298	0.2636	0.026*
C2	0.4820 (4)	1.05050 (14)	0.28520 (14)	0.0217 (7)
H2A	0.4597	1.0949	0.2985	0.026*
C3	0.6508 (4)	1.02479 (14)	0.28800 (13)	0.0209 (7)
O3	0.7894 (3)	1.05602 (10)	0.31354 (10)	0.0306 (6)
C3A	0.7517 (5)	1.11304 (17)	0.34922 (17)	0.0433 (11)
H3AA	0.8564	1.1263	0.3698	0.065*
H3AB	0.6609	1.1008	0.3763	0.065*
H3AC	0.7120	1.1508	0.3258	0.065*
C4	0.6787 (4)	0.96135 (14)	0.26409 (13)	0.0192 (7)
O5	0.8276 (3)	0.92333 (9)	0.26977 (9)	0.0229 (5)
C5	0.7845 (4)	0.85433 (13)	0.25050 (13)	0.0185 (7)
H5A	0.8728	0.8385	0.2225	0.022*
C6	0.7776 (4)	0.80540 (14)	0.30144 (13)	0.0187 (7)
O6	0.9451 (3)	0.80787 (10)	0.32591 (9)	0.0249 (5)
C6A	0.9752 (5)	0.76387 (17)	0.37266 (15)	0.0343 (9)
H6AA	1.0825	0.7770	0.3919	0.051*
H6AB	0.9856	0.7174	0.3590	0.051*
H6AC	0.8782	0.7670	0.3993	0.051*
C19	0.6274 (4)	0.82582 (14)	0.33952 (14)	0.0232 (7)
H19A	0.6426	0.8368	0.3784	0.028*
C18	0.4740 (4)	0.82718 (14)	0.31447 (14)	0.0203 (7)
H18A	0.3710	0.8384	0.3343	0.024*
C9	0.2992 (4)	0.82124 (14)	0.22128 (13)	0.0197 (7)
H9A	0.2121	0.7905	0.2390	0.024*
C10	0.2325 (4)	0.89536 (14)	0.22914 (14)	0.0228 (7)
H10A	0.1683	0.9088	0.1947	0.027*
H10B	0.1500	0.8963	0.2612	0.027*
C11	0.3751 (4)	0.94744 (14)	0.24025 (13)	0.0178 (7)
C12	0.5450 (4)	0.92669 (14)	0.23801 (14)	0.0187 (7)
C13	0.6061 (4)	0.85717 (13)	0.22250 (12)	0.0163 (7)
C14	0.4740 (4)	0.80950 (14)	0.25175 (13)	0.0168 (7)
C15	0.6159 (4)	0.84450 (14)	0.15829 (13)	0.0196 (7)
H15A	0.6887	0.8798	0.1407	0.024*
H15B	0.6724	0.8004	0.1515	0.024*
C16	0.4401 (4)	0.84459 (15)	0.13038 (14)	0.0231 (8)
H16A	0.3937	0.8911	0.1296	0.028*
H16B	0.4511	0.8286	0.0908	0.028*
N17	0.3200 (3)	0.80043 (12)	0.16154 (10)	0.0201 (6)
C17A	0.1547 (4)	0.79408 (16)	0.13129 (14)	0.0289 (8)
H17A	0.0756	0.7657	0.1533	0.043*
H17B	0.1748	0.7734	0.0942	0.043*
H17C	0.1034	0.8389	0.1262	0.043*
C8	0.5457 (4)	0.73639 (14)	0.24799 (14)	0.0195 (7)
H8A	0.5626	0.7235	0.2079	0.023*
H8B	0.4626	0.7044	0.2653	0.023*
C7	0.7217 (4)	0.73363 (15)	0.28017 (13)	0.0231 (7)
H7A	0.7046	0.7047	0.3144	0.028*
Cl7	0.88774 (11)	0.69438 (4)	0.23736 (4)	0.0290 (2)
C1'	0.3035 (4)	0.63333 (15)	−0.01950 (13)	0.0264 (8)
H1'A	0.1898	0.6513	−0.0221	0.032*
C2'	0.4351 (4)	0.67291 (16)	0.00153 (14)	0.0276 (8)
H2'A	0.4113	0.7186	0.0109	0.033*
C3'	0.6031 (4)	0.64793 (14)	0.00964 (13)	0.0242 (8)
O3'	0.7286 (3)	0.68907 (11)	0.03239 (11)	0.0386 (6)
C3A'	0.7855 (7)	0.6719 (2)	0.0850 (2)	0.0688 (15)
H3AD	0.8723	0.7047	0.0976	0.103*
H3AE	0.8373	0.6269	0.0837	0.103*
H3AF	0.6877	0.6719	0.1114	0.103*
C4'	0.6345 (4)	0.58206 (14)	−0.00769 (13)	0.0205 (7)
O5'	0.7801 (3)	0.54427 (9)	0.00406 (10)	0.0250 (5)
C5'	0.7397 (4)	0.47374 (14)	−0.01115 (13)	0.0217 (7)
H5'A	0.8336	0.4553	−0.0358	0.026*
C6'	0.7163 (4)	0.42760 (15)	0.04121 (14)	0.0230 (7)
O6'	0.8677 (3)	0.41683 (11)	0.07436 (10)	0.0343 (6)
C6A'	0.9321 (4)	0.47280 (17)	0.10669 (16)	0.0352 (9)
H6AD	1.0174	0.4566	0.1342	0.053*
H6AE	0.8359	0.4945	0.1267	0.053*
H6AF	0.9869	0.5054	0.0812	0.053*
C19'	0.5581 (4)	0.45030 (14)	0.07372 (14)	0.0226 (8)
H19C	0.5637	0.4629	0.1125	0.027*
C18'	0.4121 (4)	0.45151 (14)	0.04488 (13)	0.0189 (7)
H18B	0.3052	0.4649	0.0613	0.023*
C9'	0.2611 (4)	0.43979 (15)	−0.05240 (13)	0.0225 (8)
H9'A	0.1690	0.4106	−0.0355	0.027*
C10'	0.1956 (4)	0.51514 (15)	−0.04908 (14)	0.0238 (8)
H10C	0.1390	0.5267	−0.0854	0.029*
H10D	0.1067	0.5183	−0.0190	0.029*
C11'	0.3350 (4)	0.56691 (14)	−0.03721 (13)	0.0200 (7)
C12'	0.5054 (4)	0.54565 (13)	−0.03430 (13)	0.0173 (7)
C13'	0.5671 (4)	0.47506 (14)	−0.04456 (13)	0.0184 (7)
C14'	0.4275 (4)	0.42980 (14)	−0.01690 (13)	0.0186 (7)
C15'	0.5923 (4)	0.45809 (15)	−0.10842 (13)	0.0233 (7)
H15C	0.6702	0.4920	−0.1257	0.028*
H15D	0.6484	0.4134	−0.1119	0.028*
C16'	0.4218 (4)	0.45723 (16)	−0.14062 (14)	0.0281 (8)
H16C	0.3760	0.5037	−0.1439	0.034*
H16D	0.4406	0.4394	−0.1793	0.034*
N17'	0.2960 (4)	0.41443 (12)	−0.11032 (11)	0.0266 (7)
C17'	0.1367 (5)	0.40576 (18)	−0.14414 (16)	0.0414 (10)
H17D	0.0565	0.3761	−0.1239	0.062*
H17E	0.1660	0.3857	−0.1808	0.062*
H17F	0.0821	0.4498	−0.1501	0.062*
C8'	0.4950 (4)	0.35635 (14)	−0.01481 (14)	0.0248 (8)
H8'A	0.5152	0.3394	−0.0537	0.030*
H8'B	0.4087	0.3268	0.0038	0.030*
C7'	0.6662 (4)	0.35612 (14)	0.01909 (14)	0.0251 (8)
H7'A	0.6492	0.3264	0.0528	0.030*
Cl7'	0.84244 (12)	0.32010 (4)	−0.02329 (4)	0.0355 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0193 (17)	0.0215 (15)	0.0233 (18)	0.0049 (13)	0.0011 (16)	0.0035 (14)
C2	0.0305 (18)	0.0113 (14)	0.0232 (19)	0.0021 (14)	−0.0019 (16)	0.0001 (13)
C3	0.0262 (18)	0.0142 (14)	0.0224 (17)	−0.0049 (14)	−0.0040 (16)	0.0006 (12)
O3	0.0307 (13)	0.0185 (11)	0.0425 (16)	0.0009 (10)	−0.0122 (12)	−0.0070 (10)
C3A	0.048 (2)	0.0250 (19)	0.057 (3)	0.0056 (17)	−0.019 (2)	−0.0190 (17)
C4	0.0155 (15)	0.0192 (15)	0.0229 (18)	−0.0005 (13)	0.0031 (15)	0.0050 (13)
O5	0.0189 (11)	0.0153 (10)	0.0346 (14)	0.0016 (9)	−0.0063 (11)	−0.0027 (9)
C5	0.0208 (16)	0.0123 (13)	0.0224 (18)	−0.0022 (12)	−0.0015 (15)	−0.0006 (12)
C6	0.0204 (16)	0.0194 (15)	0.0164 (17)	−0.0003 (14)	−0.0031 (14)	−0.0008 (13)
O6	0.0242 (12)	0.0244 (12)	0.0259 (13)	0.0002 (10)	−0.0072 (10)	0.0071 (10)
C6A	0.036 (2)	0.0329 (19)	0.034 (2)	0.0056 (17)	−0.0052 (19)	0.0088 (16)
C19	0.0332 (19)	0.0181 (15)	0.0181 (17)	−0.0010 (15)	0.0014 (17)	0.0022 (13)
C18	0.0243 (17)	0.0147 (15)	0.0220 (19)	−0.0035 (13)	0.0057 (16)	0.0008 (13)
C9	0.0201 (16)	0.0207 (15)	0.0183 (17)	−0.0045 (14)	0.0008 (14)	−0.0014 (13)
C10	0.0196 (16)	0.0222 (16)	0.027 (2)	0.0006 (13)	0.0023 (16)	−0.0008 (14)
C11	0.0176 (15)	0.0181 (14)	0.0177 (17)	−0.0021 (13)	0.0005 (15)	0.0016 (13)
C12	0.0222 (17)	0.0147 (14)	0.0191 (17)	0.0003 (13)	−0.0003 (15)	0.0001 (13)
C13	0.0187 (15)	0.0144 (13)	0.0159 (17)	0.0005 (13)	−0.0009 (15)	−0.0010 (12)
C14	0.0197 (16)	0.0128 (14)	0.0180 (18)	−0.0005 (12)	0.0010 (14)	−0.0002 (12)
C15	0.0243 (17)	0.0166 (15)	0.0179 (17)	−0.0041 (13)	0.0025 (16)	0.0017 (12)
C16	0.0271 (18)	0.0212 (16)	0.0210 (18)	−0.0032 (14)	−0.0042 (16)	0.0019 (13)
N17	0.0203 (14)	0.0232 (13)	0.0167 (14)	−0.0068 (12)	−0.0023 (12)	0.0007 (11)
C17A	0.0276 (18)	0.0307 (18)	0.029 (2)	−0.0068 (16)	−0.0056 (17)	−0.0015 (15)
C8	0.0238 (17)	0.0151 (14)	0.0196 (18)	−0.0011 (13)	−0.0020 (15)	0.0044 (12)
C7	0.0303 (18)	0.0162 (15)	0.0227 (19)	0.0014 (14)	0.0025 (16)	0.0024 (13)
Cl7	0.0315 (5)	0.0209 (4)	0.0348 (5)	0.0048 (4)	0.0053 (4)	−0.0031 (4)
C1'	0.0321 (19)	0.0255 (16)	0.0215 (19)	0.0111 (15)	−0.0051 (17)	−0.0009 (14)
C2'	0.043 (2)	0.0183 (15)	0.0212 (19)	0.0049 (15)	−0.0039 (17)	0.0006 (14)
C3'	0.035 (2)	0.0168 (15)	0.0206 (18)	−0.0106 (15)	−0.0038 (17)	0.0023 (13)
O3'	0.0510 (16)	0.0267 (12)	0.0382 (16)	−0.0178 (12)	−0.0134 (14)	−0.0017 (11)
C3A'	0.097 (4)	0.039 (2)	0.070 (3)	−0.026 (2)	−0.047 (3)	−0.002 (2)
C4'	0.0242 (18)	0.0184 (14)	0.0190 (17)	−0.0003 (14)	−0.0019 (15)	0.0047 (13)
O5'	0.0206 (12)	0.0189 (10)	0.0354 (14)	−0.0017 (9)	−0.0039 (11)	−0.0034 (9)
C5'	0.0200 (17)	0.0168 (14)	0.0281 (19)	−0.0001 (13)	−0.0034 (16)	−0.0027 (14)
C6'	0.0234 (18)	0.0190 (15)	0.0266 (19)	0.0013 (14)	−0.0074 (16)	−0.0022 (14)
O6'	0.0370 (15)	0.0299 (13)	0.0358 (15)	0.0076 (11)	−0.0192 (13)	−0.0053 (11)
C6A'	0.029 (2)	0.039 (2)	0.037 (2)	0.0002 (16)	−0.0091 (18)	−0.0084 (17)
C19'	0.036 (2)	0.0147 (15)	0.0174 (18)	−0.0008 (14)	−0.0026 (16)	0.0005 (13)
C18'	0.0249 (18)	0.0163 (15)	0.0155 (17)	−0.0005 (13)	0.0002 (15)	0.0002 (12)
C9'	0.0217 (18)	0.0222 (16)	0.0235 (19)	−0.0061 (13)	−0.0042 (15)	0.0023 (13)
C10'	0.0197 (18)	0.0232 (16)	0.029 (2)	−0.0003 (14)	−0.0054 (16)	0.0041 (14)
C11'	0.0259 (18)	0.0218 (15)	0.0121 (17)	0.0031 (14)	−0.0042 (15)	0.0016 (13)
C12'	0.0233 (17)	0.0121 (14)	0.0164 (18)	−0.0010 (13)	−0.0005 (14)	0.0056 (12)
C13'	0.0226 (17)	0.0159 (15)	0.0167 (17)	−0.0022 (13)	−0.0034 (15)	−0.0002 (13)
C14'	0.0229 (17)	0.0144 (14)	0.0184 (18)	0.0010 (12)	−0.0025 (15)	0.0017 (12)
C15'	0.0264 (18)	0.0241 (16)	0.0195 (18)	−0.0013 (14)	0.0030 (16)	0.0018 (13)
C16'	0.040 (2)	0.0250 (17)	0.0194 (19)	0.0009 (16)	−0.0024 (17)	−0.0002 (14)
N17'	0.0327 (16)	0.0257 (14)	0.0214 (16)	−0.0090 (12)	−0.0105 (14)	0.0003 (11)
C17'	0.050 (3)	0.038 (2)	0.036 (2)	−0.0157 (19)	−0.017 (2)	−0.0013 (17)
C8'	0.036 (2)	0.0160 (15)	0.0220 (19)	−0.0033 (15)	−0.0030 (17)	0.0004 (13)
C7'	0.0332 (19)	0.0167 (14)	0.0255 (19)	0.0070 (14)	0.0031 (17)	−0.0005 (13)
Cl7'	0.0429 (5)	0.0234 (4)	0.0401 (6)	0.0115 (4)	−0.0003 (5)	−0.0041 (4)

Geometric parameters (Å, º)

C1—C2	1.403 (4)	C1'—C2'	1.377 (4)
C1—C11	1.409 (4)	C1'—C11'	1.403 (4)
C1—H1A	0.9500	C1'—H1'A	0.9500
C2—C3	1.402 (4)	C2'—C3'	1.403 (4)
C2—H2A	0.9500	C2'—H2'A	0.9500
C3—O3	1.376 (4)	C3'—O3'	1.376 (4)
C3—C4	1.396 (4)	C3'—C4'	1.390 (4)
O3—C3A	1.440 (4)	O3'—C3A'	1.360 (5)
C3A—H3AA	0.9800	C3A'—H3AD	0.9800
C3A—H3AB	0.9800	C3A'—H3AE	0.9800
C3A—H3AC	0.9800	C3A'—H3AF	0.9800
C4—C12	1.386 (4)	C4'—O5'	1.380 (4)
C4—O5	1.382 (3)	C4'—C12'	1.382 (4)
O5—C5	1.480 (3)	O5'—C5'	1.478 (3)
C5—C13	1.530 (4)	C5'—C6'	1.549 (4)
C5—C6	1.547 (4)	C5'—C13'	1.549 (4)
C5—H5A	1.0000	C5'—H5'A	1.0000
C6—O6	1.419 (3)	C6'—O6'	1.424 (4)
C6—C19	1.523 (4)	C6'—C19'	1.511 (4)
C6—C7	1.570 (4)	C6'—C7'	1.560 (4)
O6—C6A	1.426 (4)	O6'—C6A'	1.436 (4)
C6A—H6AA	0.9800	C6A'—H6AD	0.9800
C6A—H6AB	0.9800	C6A'—H6AE	0.9800
C6A—H6AC	0.9800	C6A'—H6AF	0.9800
C19—C18	1.325 (4)	C19'—C18'	1.318 (4)
C19—H19A	0.9500	C19'—H19C	0.9500
C18—C14	1.522 (4)	C18'—C14'	1.526 (4)
C18—H18A	0.9500	C18'—H18B	0.9500
C9—N17	1.479 (4)	C9'—N17'	1.482 (4)
C9—C14	1.548 (4)	C9'—C14'	1.548 (4)
C9—C10	1.569 (4)	C9'—C10'	1.579 (4)
C9—H9A	1.0000	C9'—H9'A	1.0000
C10—C11	1.533 (4)	C10'—C11'	1.514 (4)
C10—H10A	0.9900	C10'—H10C	0.9900
C10—H10B	0.9900	C10'—H10D	0.9900
C11—C12	1.377 (4)	C11'—C12'	1.384 (4)
C12—C13	1.503 (4)	C12'—C13'	1.499 (4)
C13—C15	1.539 (4)	C13'—C14'	1.548 (4)
C13—C14	1.554 (4)	C13'—C15'	1.557 (4)
C14—C8	1.555 (4)	C14'—C8'	1.548 (4)
C15—C16	1.510 (4)	C15'—C16'	1.521 (4)
C15—H15A	0.9900	C15'—H15C	0.9900
C15—H15B	0.9900	C15'—H15D	0.9900
C16—N17	1.473 (4)	C16'—N17'	1.476 (4)
C16—H16A	0.9900	C16'—H16C	0.9900
C16—H16B	0.9900	C16'—H16D	0.9900
N17—C17A	1.469 (4)	N17'—C17'	1.477 (4)
C17A—H17A	0.9800	C17'—H17D	0.9800
C17A—H17B	0.9800	C17'—H17E	0.9800
C17A—H17C	0.9800	C17'—H17F	0.9800
C8—C7	1.559 (4)	C8'—C7'	1.546 (4)
C8—H8A	0.9900	C8'—H8'A	0.9900
C8—H8B	0.9900	C8'—H8'B	0.9900
C7—Cl7	1.809 (3)	C7'—Cl7'	1.835 (3)
C7—H7A	1.0000	C7'—H7'A	1.0000
C2—C1—C11	120.9 (3)	C2'—C1'—C11'	121.0 (3)
C2—C1—H1A	119.5	C2'—C1'—H1'A	119.5
C11—C1—H1A	119.5	C11'—C1'—H1'A	119.5
C3—C2—C1	121.3 (3)	C1'—C2'—C3'	122.1 (3)
C3—C2—H2A	119.3	C1'—C2'—H2'A	119.0
C1—C2—H2A	119.3	C3'—C2'—H2'A	119.0
O3—C3—C4	117.6 (3)	O3'—C3'—C4'	123.3 (3)
O3—C3—C2	125.5 (3)	O3'—C3'—C2'	119.7 (3)
C4—C3—C2	116.9 (3)	C4'—C3'—C2'	116.9 (3)
C3—O3—C3A	116.9 (2)	C3A'—O3'—C3'	115.8 (3)
O3—C3A—H3AA	109.5	O3'—C3A'—H3AD	109.5
O3—C3A—H3AB	109.5	O3'—C3A'—H3AE	109.5
H3AA—C3A—H3AB	109.5	H3AD—C3A'—H3AE	109.5
O3—C3A—H3AC	109.5	O3'—C3A'—H3AF	109.5
H3AA—C3A—H3AC	109.5	H3AD—C3A'—H3AF	109.5
H3AB—C3A—H3AC	109.5	H3AE—C3A'—H3AF	109.5
C12—C4—O5	113.2 (2)	O5'—C4'—C12'	113.3 (2)
C12—C4—C3	120.8 (3)	O5'—C4'—C3'	126.4 (3)
O5—C4—C3	125.5 (3)	C12'—C4'—C3'	119.9 (3)
C4—O5—C5	106.7 (2)	C4'—O5'—C5'	107.0 (2)
O5—C5—C13	107.5 (2)	O5'—C5'—C6'	112.9 (2)
O5—C5—C6	110.4 (2)	O5'—C5'—C13'	106.8 (2)
C13—C5—C6	109.2 (2)	C6'—C5'—C13'	108.4 (2)
O5—C5—H5A	109.9	O5'—C5'—H5'A	109.5
C13—C5—H5A	109.9	C6'—C5'—H5'A	109.5
C6—C5—H5A	109.9	C13'—C5'—H5'A	109.5
O6—C6—C19	116.4 (2)	O6'—C6'—C19'	115.4 (3)
O6—C6—C5	105.3 (2)	O6'—C6'—C5'	115.6 (3)
C19—C6—C5	108.6 (2)	C19'—C6'—C5'	108.9 (2)
O6—C6—C7	114.4 (2)	O6'—C6'—C7'	104.6 (2)
C19—C6—C7	102.8 (2)	C19'—C6'—C7'	103.9 (2)
C5—C6—C7	109.2 (2)	C5'—C6'—C7'	107.4 (3)
C6—O6—C6A	116.3 (2)	C6'—O6'—C6A'	117.4 (2)
O6—C6A—H6AA	109.5	O6'—C6A'—H6AD	109.5
O6—C6A—H6AB	109.5	O6'—C6A'—H6AE	109.5
H6AA—C6A—H6AB	109.5	H6AD—C6A'—H6AE	109.5
O6—C6A—H6AC	109.5	O6'—C6A'—H6AF	109.5
H6AA—C6A—H6AC	109.5	H6AD—C6A'—H6AF	109.5
H6AB—C6A—H6AC	109.5	H6AE—C6A'—H6AF	109.5
C18—C19—C6	115.0 (3)	C18'—C19'—C6'	115.8 (3)
C18—C19—H19A	122.5	C18'—C19'—H19C	122.1
C6—C19—H19A	122.5	C6'—C19'—H19C	122.1
C19—C18—C14	115.5 (3)	C19'—C18'—C14'	115.0 (3)
C19—C18—H18A	122.3	C19'—C18'—H18B	122.5
C14—C18—H18A	122.3	C14'—C18'—H18B	122.5
N17—C9—C14	107.9 (2)	N17'—C9'—C14'	107.8 (3)
N17—C9—C10	114.2 (2)	N17'—C9'—C10'	115.2 (3)
C14—C9—C10	111.9 (2)	C14'—C9'—C10'	111.1 (2)
N17—C9—H9A	107.5	N17'—C9'—H9'A	107.5
C14—C9—H9A	107.5	C14'—C9'—H9'A	107.5
C10—C9—H9A	107.5	C10'—C9'—H9'A	107.5
C11—C10—C9	114.5 (2)	C11'—C10'—C9'	115.0 (2)
C11—C10—H10A	108.6	C11'—C10'—H10C	108.5
C9—C10—H10A	108.6	C9'—C10'—H10C	108.5
C11—C10—H10B	108.6	C11'—C10'—H10D	108.5
C9—C10—H10B	108.6	C9'—C10'—H10D	108.5
H10A—C10—H10B	107.6	H10C—C10'—H10D	107.5
C12—C11—C1	116.2 (3)	C12'—C11'—C1'	115.9 (3)
C12—C11—C10	118.5 (3)	C12'—C11'—C10'	118.6 (3)
C1—C11—C10	124.1 (3)	C1'—C11'—C10'	124.6 (3)
C11—C12—C4	123.1 (3)	C4'—C12'—C11'	123.3 (3)
C11—C12—C13	125.7 (3)	C4'—C12'—C13'	109.4 (3)
C4—C12—C13	109.2 (2)	C11'—C12'—C13'	125.4 (3)
C12—C13—C5	102.2 (2)	C12'—C13'—C5'	102.0 (2)
C12—C13—C15	113.9 (2)	C12'—C13'—C14'	104.6 (2)
C5—C13—C15	112.1 (2)	C5'—C13'—C14'	112.0 (2)
C12—C13—C14	104.1 (2)	C12'—C13'—C15'	113.5 (2)
C5—C13—C14	112.2 (2)	C5'—C13'—C15'	112.5 (3)
C15—C13—C14	111.8 (2)	C14'—C13'—C15'	111.7 (2)
C18—C14—C9	114.7 (3)	C18'—C14'—C9'	114.6 (3)
C18—C14—C13	107.0 (2)	C18'—C14'—C8'	105.2 (2)
C9—C14—C13	106.0 (2)	C9'—C14'—C8'	114.7 (2)
C18—C14—C8	105.7 (2)	C18'—C14'—C13'	107.1 (2)
C9—C14—C8	115.1 (2)	C9'—C14'—C13'	106.0 (2)
C13—C14—C8	107.9 (2)	C8'—C14'—C13'	108.9 (2)
C16—C15—C13	112.7 (3)	C16'—C15'—C13'	112.3 (3)
C16—C15—H15A	109.0	C16'—C15'—H15C	109.2
C13—C15—H15A	109.0	C13'—C15'—H15C	109.2
C16—C15—H15B	109.0	C16'—C15'—H15D	109.2
C13—C15—H15B	109.0	C13'—C15'—H15D	109.2
H15A—C15—H15B	107.8	H15C—C15'—H15D	107.9
N17—C16—C15	110.4 (2)	N17'—C16'—C15'	109.5 (3)
N17—C16—H16A	109.6	N17'—C16'—H16C	109.8
C15—C16—H16A	109.6	C15'—C16'—H16C	109.8
N17—C16—H16B	109.6	N17'—C16'—H16D	109.8
C15—C16—H16B	109.6	C15'—C16'—H16D	109.8
H16A—C16—H16B	108.1	H16C—C16'—H16D	108.2
C17A—N17—C16	110.8 (2)	C17'—N17'—C16'	110.7 (3)
C17A—N17—C9	113.2 (2)	C17'—N17'—C9'	112.8 (3)
C16—N17—C9	112.3 (2)	C16'—N17'—C9'	111.9 (2)
N17—C17A—H17A	109.5	N17'—C17'—H17D	109.5
N17—C17A—H17B	109.5	N17'—C17'—H17E	109.5
H17A—C17A—H17B	109.5	H17D—C17'—H17E	109.5
N17—C17A—H17C	109.5	N17'—C17'—H17F	109.5
H17A—C17A—H17C	109.5	H17D—C17'—H17F	109.5
H17B—C17A—H17C	109.5	H17E—C17'—H17F	109.5
C14—C8—C7	108.4 (2)	C14'—C8'—C7'	107.9 (2)
C14—C8—H8A	110.0	C14'—C8'—H8'A	110.1
C7—C8—H8A	110.0	C7'—C8'—H8'A	110.1
C14—C8—H8B	110.0	C14'—C8'—H8'B	110.1
C7—C8—H8B	110.0	C7'—C8'—H8'B	110.1
H8A—C8—H8B	108.4	H8'A—C8'—H8'B	108.4
C8—C7—C6	111.3 (2)	C8'—C7'—C6'	112.5 (2)
C8—C7—Cl7	111.2 (2)	C8'—C7'—Cl7'	110.7 (2)
C6—C7—Cl7	112.0 (2)	C6'—C7'—Cl7'	110.6 (2)
C8—C7—H7A	107.4	C8'—C7'—H7'A	107.6
C6—C7—H7A	107.4	C6'—C7'—H7'A	107.6
Cl7—C7—H7A	107.4	Cl7'—C7'—H7'A	107.6
C11—C1—C2—C3	−3.3 (5)	C11'—C1'—C2'—C3'	−4.1 (5)
C1—C2—C3—O3	−173.7 (3)	C1'—C2'—C3'—O3'	−178.1 (3)
C1—C2—C3—C4	4.5 (5)	C1'—C2'—C3'—C4'	3.7 (5)
C4—C3—O3—C3A	−165.8 (3)	C4'—C3'—O3'—C3A'	−69.6 (5)
C2—C3—O3—C3A	12.4 (5)	C2'—C3'—O3'—C3A'	112.2 (4)
O3—C3—C4—C12	179.5 (3)	O3'—C3'—C4'—O5'	12.6 (5)
C2—C3—C4—C12	1.2 (5)	C2'—C3'—C4'—O5'	−169.2 (3)
O3—C3—C4—O5	8.5 (5)	O3'—C3'—C4'—C12'	−174.8 (3)
C2—C3—C4—O5	−169.9 (3)	C2'—C3'—C4'—C12'	3.3 (5)
C12—C4—O5—C5	−5.7 (3)	C12'—C4'—O5'—C5'	−5.8 (3)
C3—C4—O5—C5	165.9 (3)	C3'—C4'—O5'—C5'	167.2 (3)
C4—O5—C5—C13	10.2 (3)	C4'—O5'—C5'—C6'	−108.0 (3)
C4—O5—C5—C6	−108.8 (3)	C4'—O5'—C5'—C13'	11.1 (3)
O5—C5—C6—O6	−59.8 (3)	O5'—C5'—C6'—O6'	−66.3 (3)
C13—C5—C6—O6	−177.9 (2)	C13'—C5'—C6'—O6'	175.5 (2)
O5—C5—C6—C19	65.5 (3)	O5'—C5'—C6'—C19'	65.5 (3)
C13—C5—C6—C19	−52.5 (3)	C13'—C5'—C6'—C19'	−52.7 (3)
O5—C5—C6—C7	176.9 (2)	O5'—C5'—C6'—C7'	177.4 (2)
C13—C5—C6—C7	58.9 (3)	C13'—C5'—C6'—C7'	59.2 (3)
C19—C6—O6—C6A	62.7 (3)	C19'—C6'—O6'—C6A'	−58.5 (4)
C5—C6—O6—C6A	−176.9 (3)	C5'—C6'—O6'—C6A'	70.2 (4)
C7—C6—O6—C6A	−57.0 (3)	C7'—C6'—O6'—C6A'	−172.0 (3)
O6—C6—C19—C18	175.8 (3)	O6'—C6'—C19'—C18'	−171.1 (2)
C5—C6—C19—C18	57.3 (3)	C5'—C6'—C19'—C18'	57.0 (3)
C7—C6—C19—C18	−58.4 (3)	C7'—C6'—C19'—C18'	−57.2 (3)
C6—C19—C18—C14	−1.1 (4)	C6'—C19'—C18'—C14'	−0.1 (4)
N17—C9—C10—C11	−97.1 (3)	N17'—C9'—C10'—C11'	−96.4 (3)
C14—C9—C10—C11	25.8 (4)	C14'—C9'—C10'—C11'	26.4 (4)
C2—C1—C11—C12	−3.7 (4)	C2'—C1'—C11'—C12'	−2.6 (5)
C2—C1—C11—C10	164.0 (3)	C2'—C1'—C11'—C10'	166.5 (3)
C9—C10—C11—C12	5.0 (4)	C9'—C10'—C11'—C12'	4.5 (4)
C9—C10—C11—C1	−162.4 (3)	C9'—C10'—C11'—C1'	−164.4 (3)
C1—C11—C12—C4	9.7 (5)	O5'—C4'—C12'—C11'	162.9 (3)
C10—C11—C12—C4	−158.7 (3)	C3'—C4'—C12'—C11'	−10.6 (5)
C1—C11—C12—C13	171.7 (3)	O5'—C4'—C12'—C13'	−2.2 (4)
C10—C11—C12—C13	3.4 (5)	C3'—C4'—C12'—C13'	−175.7 (3)
O5—C4—C12—C11	163.4 (3)	C1'—C11'—C12'—C4'	10.0 (5)
C3—C4—C12—C11	−8.7 (5)	C10'—C11'—C12'—C4'	−159.8 (3)
O5—C4—C12—C13	−1.2 (4)	C1'—C11'—C12'—C13'	172.7 (3)
C3—C4—C12—C13	−173.3 (3)	C10'—C11'—C12'—C13'	2.9 (5)
C11—C12—C13—C5	−156.9 (3)	C4'—C12'—C13'—C5'	8.7 (3)
C4—C12—C13—C5	7.3 (3)	C11'—C12'—C13'—C5'	−156.0 (3)
C11—C12—C13—C15	82.0 (4)	C4'—C12'—C13'—C14'	125.5 (3)
C4—C12—C13—C15	−113.8 (3)	C11'—C12'—C13'—C14'	−39.2 (4)
C11—C12—C13—C14	−40.0 (4)	C4'—C12'—C13'—C15'	−112.5 (3)
C4—C12—C13—C14	124.2 (3)	C11'—C12'—C13'—C15'	82.8 (4)
O5—C5—C13—C12	−10.5 (3)	O5'—C5'—C13'—C12'	−11.8 (3)
C6—C5—C13—C12	109.3 (3)	C6'—C5'—C13'—C12'	110.2 (3)
O5—C5—C13—C15	111.9 (3)	O5'—C5'—C13'—C14'	−123.1 (3)
C6—C5—C13—C15	−128.3 (2)	C6'—C5'—C13'—C14'	−1.1 (3)
O5—C5—C13—C14	−121.4 (2)	O5'—C5'—C13'—C15'	110.0 (3)
C6—C5—C13—C14	−1.6 (3)	C6'—C5'—C13'—C15'	−128.0 (3)
C19—C18—C14—C9	−171.6 (3)	C19'—C18'—C14'—C9'	−172.7 (2)
C19—C18—C14—C13	−54.4 (3)	C19'—C18'—C14'—C8'	60.4 (3)
C19—C18—C14—C8	60.5 (3)	C19'—C18'—C14'—C13'	−55.4 (3)
N17—C9—C14—C18	−178.8 (2)	N17'—C9'—C14'—C18'	−178.2 (2)
C10—C9—C14—C18	54.7 (3)	C10'—C9'—C14'—C18'	54.7 (3)
N17—C9—C14—C13	63.3 (3)	N17'—C9'—C14'—C8'	−56.4 (3)
C10—C9—C14—C13	−63.1 (3)	C10'—C9'—C14'—C8'	176.6 (3)
N17—C9—C14—C8	−55.9 (3)	N17'—C9'—C14'—C13'	63.8 (3)
C10—C9—C14—C8	177.7 (2)	C10'—C9'—C14'—C13'	−63.2 (3)
C12—C13—C14—C18	−55.9 (3)	C12'—C13'—C14'—C18'	−56.0 (3)
C5—C13—C14—C18	53.8 (3)	C5'—C13'—C14'—C18'	53.6 (3)
C15—C13—C14—C18	−179.3 (2)	C15'—C13'—C14'—C18'	−179.1 (2)
C12—C13—C14—C9	66.9 (3)	C12'—C13'—C14'—C9'	66.8 (3)
C5—C13—C14—C9	176.6 (2)	C5'—C13'—C14'—C9'	176.5 (2)
C15—C13—C14—C9	−56.5 (3)	C15'—C13'—C14'—C9'	−56.3 (3)
C12—C13—C14—C8	−169.3 (2)	C12'—C13'—C14'—C8'	−169.3 (2)
C5—C13—C14—C8	−59.5 (3)	C5'—C13'—C14'—C8'	−59.6 (3)
C15—C13—C14—C8	67.3 (3)	C15'—C13'—C14'—C8'	67.6 (3)
C12—C13—C15—C16	−66.7 (3)	C12'—C13'—C15'—C16'	−66.8 (3)
C5—C13—C15—C16	177.9 (2)	C5'—C13'—C15'—C16'	178.2 (2)
C14—C13—C15—C16	51.0 (3)	C14'—C13'—C15'—C16'	51.2 (3)
C13—C15—C16—N17	−49.6 (3)	C13'—C15'—C16'—N17'	−50.6 (3)
C15—C16—N17—C17A	−173.6 (2)	C15'—C16'—N17'—C17'	−172.9 (3)
C15—C16—N17—C9	58.7 (3)	C15'—C16'—N17'—C9'	60.4 (3)
C14—C9—N17—C17A	166.6 (2)	C14'—C9'—N17'—C17'	166.0 (2)
C10—C9—N17—C17A	−68.4 (3)	C10'—C9'—N17'—C17'	−69.4 (3)
C14—C9—N17—C16	−67.0 (3)	C14'—C9'—N17'—C16'	−68.5 (3)
C10—C9—N17—C16	58.0 (3)	C10'—C9'—N17'—C16'	56.2 (3)
C18—C14—C8—C7	−52.8 (3)	C18'—C14'—C8'—C7'	−56.4 (3)
C9—C14—C8—C7	179.5 (2)	C9'—C14'—C8'—C7'	176.7 (2)
C13—C14—C8—C7	61.4 (3)	C13'—C14'—C8'—C7'	58.1 (3)
C14—C8—C7—C6	−4.7 (3)	C14'—C8'—C7'—C6'	1.0 (4)
C14—C8—C7—Cl7	−130.3 (2)	C14'—C8'—C7'—Cl7'	−123.4 (2)
O6—C6—C7—C8	−173.7 (2)	O6'—C6'—C7'—C8'	175.9 (3)
C19—C6—C7—C8	59.1 (3)	C19'—C6'—C7'—C8'	54.4 (3)
C5—C6—C7—C8	−56.1 (3)	C5'—C6'—C7'—C8'	−60.8 (3)
O6—C6—C7—Cl7	−48.6 (3)	O6'—C6'—C7'—Cl7'	−59.7 (3)
C19—C6—C7—Cl7	−175.7 (2)	C19'—C6'—C7'—Cl7'	178.9 (2)
C5—C6—C7—Cl7	69.1 (3)	C5'—C6'—C7'—Cl7'	63.6 (3)