 
data_8esB

# Loop of author details

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
'Munro, Thomas A.'
;
McLean Hospital, 115 Mill St, Belmont MA, USA 02478-9106
;
.
'Duncan, Katharine K.'
;
McLean Hospital, 115 Mill St, Belmont MA, USA 02478-9106
;
.
'Staples, Richard J.'
;
Department of Chemistry and Chemical Biology,
Harvard University, Cambridge MA 02138, USA
;
.
'Xu, Wei'
;
Department of Pharmacology, Temple University, 3420 N. Broad Street,
Philadelphia, PA 19140, USA.
;
.
'Liu-Chen, Lee-Yuan'
;
Department of Pharmacology, Temple University, 3420 N. Broad Street,
Philadelphia, PA 19140, USA.
;
.
'Béguin, Cécile'
;
McLean Hospital, 115 Mill St, Belmont MA, USA 02478-9106
;
.
'Carlezon Jr, William A.'
;
McLean Hospital, 115 Mill St, Belmont MA, USA 02478-9106
;
.
'Cohen, Bruce M.'
;
McLean Hospital, 115 Mill St, Belmont MA, USA 02478-9106
;
.




# start Validation Reply Form
_vrf_REFLT_03_abp2t
;
PROBLEM: Alert B: < 90% complete (theta
max?)
RESPONSE: We collect and use all the data that the detector sees, including
the corners of the detector.  This results in a high 2theta value and a lower
percent complete.  If we cut the data to 50 degrees 2 theta we get  0.99 for 
the complete fraction.  We feel all the data should be used that is collected.
;

# end Validation Reply Form

_audit_update_record
;
2006-09-18 # Formatted by publCIF
;
_publ_requested_journal          
'Beilstein Journal of Organic Chemistry'

_publ_section_title
;
8-epi-Salvinorin B: crystal structure and affinity at the κ opioid receptor
;

_publ_section_abstract
;
There have been many reports of epimerization of salvinorins at C-8 under basic
conditions, but little evidence has been presented to establish the structure
of these compounds. We report here the first crystal structure of an
8-epi-salvinorin or derivative: the title compound, 2b. The
lactone adopts a boat conformation with the furan equatorial. Several lines of
evidence suggest that epimerization proceeds via enolization of the lactone
rather than a previously proposed indirect mechanism. Consistent with the
general trend in related compounds, the title compound showed lower affinity
at the kappa opioid receptor than the natural epimer salvinorin B (2a).
The related 8-epi-acid 4b showed no affinity.
;

_publ_contact_author_name        'Thomas Anthony Munro'
_publ_contact_author_address     
;
MRC 331, McLean Hospital,
115 Mill st, Belmont MA 02478-9106
;


_publ_contact_author_email       'tmunro@mclean.harvard.edu'
_publ_contact_author_phone       '+1 617 855 2095'
_publ_contact_author_fax         '+1 617 855 3479'

_audit_creation_method           SHELXL-97
_chemical_name_systematic
;        
(2S,4aS,6aR,7R,9S,10aS,10bR)-methyl
2-(3-furanyl)-dodecahydro-9-hydroxy-6a,10b-dimethyl-4,10-dioxo-
2H-naphtho[2,1-c]pyran-7-carboxylate
;
_chemical_name_common            '8-epi-salvinorin B'
_chemical_melting_point          467
_chemical_formula_moiety         'C21 H26 O7'
_chemical_formula_sum            'C21 H26 O7'
_chemical_formula_weight         390.42
_chemical_absolute_configuration syn
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    P21
_symmetry_space_group_name_Hall   P2yb
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
  
_cell_length_a                    10.5103(16) 
_cell_length_b                    7.5216(12) 
_cell_length_c                    24.079(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  93.496(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1900.0(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     193(2) 
_cell_measurement_reflns_used     991 
_cell_measurement_theta_min       2.16 
_cell_measurement_theta_max       27.75 
  
_exptl_crystal_description        needle 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.22 
_exptl_crystal_size_mid           0.08 
_exptl_crystal_size_min           0.08 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.365 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              832 
_exptl_absorpt_coefficient_mu     0.102 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
  
_exptl_special_details 
; 
Data was collected using a BRUKER SMART CCD (charge coupled device) based 
diffractometer equipped with an oxford low-temperature apparatus operating at 
193 K.  A suitable crystal was chosen and mounted on a glass fiber using 
grease. Data were measured using omega scans of 0.3° per frame for 30 s, 
such that a hemisphere was collected. A total of 1271 frames were collected 
with a final resolution of 0.76 Å.  The first 50 frames  were recollected 
at the end of data collection to monitor for decay.  Cell parameters were 
retrieved using SMART software and refined using SAINT on all observed 
reflections. Data reduction was performed using the SAINT software which 
corrects for Lp and decay.The structures are solved by the direct method 
using the SHELX-90 program and refined by least squares method on F2 SHELXL-93, 
incorporated in SHELXTL V6.1. 
  
All H atoms were placed in calculated positions and refined using a riding 
model. 
C-H(aromatic) = 0.94Å and Uiso(H) = 1.2Ueq(C) 
C-H(aliphatic) = 0.99Å and Uiso(H) = 1.2Ueq(C) 
CH2 = 0.98Å and Uiso(H) = 1.2Ueq(C) 
CH3 = 0.97Å and Uiso(H) = 1.5Ueq(C) 
N-H = 0.86 (0.92)Å and Uiso(H) = 1.2 Ueq(N) 
O-H(alcohol) = 0.85Å and Uiso(H) = 1.2Ueq(O) 
O-H(acid) = 0.82Å and Uiso(H) = 1.5Ueq(O) 
; 
  
_diffrn_ambient_temperature       193(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'normal-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker CCD' 
_diffrn_measurement_method        'ω, 0.3 deg' 
_diffrn_detector_area_resol_mean  836.6 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  0 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ?
 
_diffrn_reflns_number             13595 
_diffrn_reflns_av_R_equivalents   0.0407 
_diffrn_reflns_av_sigmaI/netI     0.0485 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -7 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -31 
_diffrn_reflns_limit_l_max        28 
_diffrn_reflns_theta_min          0.85 
_diffrn_reflns_theta_max          27.88 
_reflns_number_total              7036 
_reflns_number_gt                 6275 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'ASTRO (Bruker, 1997)' 
_computing_cell_refinement        'SMART (Bruker, 2001)' 
_computing_data_reduction         'SAINT (Bruker, 2001)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 2005)' 
_computing_publication_material   'XCIF (Sheldrick and Bruker, 1997)' 
  
_refine_special_details 
; 
 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 > 2sigma(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. 
; 
  
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0480P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details  ?
_refine_ls_abs_structure_Flack    ? 
_refine_ls_number_reflns          7036 
_refine_ls_number_parameters      513 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0481 
_refine_ls_R_factor_gt            0.0427 
_refine_ls_wR_factor_ref          0.0962 
_refine_ls_wR_factor_gt           0.0934 
_refine_ls_goodness_of_fit_ref    1.010 
_refine_ls_restrained_S_all       1.010 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1A O 0.14699(13) 0.3765(2) 0.89444(6) 0.0403(4) Uani 1 1 d . . . 
O2A O 0.16210(18) 0.4992(2) 0.99636(7) 0.0496(4) Uani 1 1 d . . . 
H2A H 0.1171 0.5250 0.9675 0.074 Uiso 1 1 calc R . . 
O12A O 0.54169(13) 0.1228(2) 0.79731(6) 0.0345(3) Uani 1 1 d . . . 
O15A O 0.59181(18) 0.6098(3) 0.71796(8) 0.0702(6) Uani 1 1 d . . . 
O17A O 0.60599(14) -0.0884(2) 0.85585(6) 0.0416(4) Uani 1 1 d . . . 
O18A O 0.40681(15) -0.1841(3) 1.06730(7) 0.0615(6) Uani 1 1 d . . . 
O21A O 0.20152(13) -0.1172(2) 1.07398(6) 0.0360(4) Uani 1 1 d . . . 
C1A C 0.22272(17) 0.2963(3) 0.92538(8) 0.0274(4) Uani 1 1 d . . . 
C2A C 0.2457(2) 0.3592(3) 0.98469(9) 0.0339(5) Uani 1 1 d . . . 
H2A1 H 0.3350 0.4052 0.9894 0.041 Uiso 1 1 calc R . . 
C3A C 0.2324(2) 0.2064(3) 1.02544(9) 0.0343(5) Uani 1 1 d . . . 
H3A1 H 0.1419 0.1698 1.0254 0.041 Uiso 1 1 calc R . . 
H3A2 H 0.2598 0.2463 1.0635 0.041 Uiso 1 1 calc R . . 
C4A C 0.31367(19) 0.0484(3) 1.00935(8) 0.0290(4) Uani 1 1 d . . . 
H4A H 0.4032 0.0929 1.0087 0.035 Uiso 1 1 calc R . . 
C5A C 0.27607(17) -0.0224(3) 0.94940(8) 0.0255(4) Uani 1 1 d . . . 
C6A C 0.36814(19) -0.1707(3) 0.93499(9) 0.0320(5) Uani 1 1 d . . . 
H6A1 H 0.4563 -0.1320 0.9456 0.038 Uiso 1 1 calc R . . 
H6A2 H 0.3503 -0.2771 0.9574 0.038 Uiso 1 1 calc R . . 
C7A C 0.3597(2) -0.2220(3) 0.87357(9) 0.0374(5) Uani 1 1 d . . . 
H7A1 H 0.2751 -0.2758 0.8641 0.045 Uiso 1 1 calc R . . 
H7A2 H 0.4252 -0.3131 0.8672 0.045 Uiso 1 1 calc R . . 
C8A C 0.37864(19) -0.0643(3) 0.83468(8) 0.0307(5) Uani 1 1 d . . . 
H8A H 0.3510 -0.1072 0.7965 0.037 Uiso 1 1 calc R . . 
C9A C 0.29170(18) 0.0978(3) 0.84588(8) 0.0268(4) Uani 1 1 d . . . 
C10A C 0.29936(17) 0.1360(3) 0.90956(8) 0.0238(4) Uani 1 1 d . . . 
H10A H 0.3901 0.1710 0.9185 0.029 Uiso 1 1 calc R . . 
C11A C 0.34408(18) 0.2644(3) 0.81726(8) 0.0295(4) Uani 1 1 d . . . 
H11A H 0.2718 0.3351 0.8008 0.035 Uiso 1 1 calc R . . 
H11B H 0.3909 0.3391 0.8455 0.035 Uiso 1 1 calc R . . 
C12A C 0.43250(19) 0.2162(3) 0.77203(8) 0.0312(5) Uani 1 1 d . . . 
H12A H 0.3864 0.1367 0.7443 0.037 Uiso 1 1 calc R . . 
C13A C 0.4786(2) 0.3767(3) 0.74307(8) 0.0349(5) Uani 1 1 d . . . 
C14A C 0.4153(2) 0.4617(4) 0.69658(10) 0.0472(6) Uani 1 1 d . . . 
H14A H 0.3368 0.4262 0.6783 0.057 Uiso 1 1 calc R . . 
C15A C 0.4860(2) 0.6000(5) 0.68343(11) 0.0541(7) Uani 1 1 d . . . 
H15A H 0.4650 0.6805 0.6539 0.065 Uiso 1 1 calc R . . 
C16A C 0.5845(3) 0.4703(4) 0.75403(11) 0.0572(8) Uani 1 1 d . . . 
H16A H 0.6469 0.4438 0.7831 0.069 Uiso 1 1 calc R . . 
C17A C 0.5179(2) -0.0136(3) 0.83210(8) 0.0315(5) Uani 1 1 d . . . 
C18A C 0.31472(19) -0.0978(3) 1.05280(8) 0.0349(5) Uani 1 1 d . . . 
C19A C 0.13643(18) -0.0856(3) 0.94551(9) 0.0314(4) Uani 1 1 d . . . 
H19A H 0.1213 -0.1605 0.9125 0.047 Uiso 1 1 calc R . . 
H19B H 0.0797 0.0178 0.9427 0.047 Uiso 1 1 calc R . . 
H19C H 0.1194 -0.1542 0.9788 0.047 Uiso 1 1 calc R . . 
C20A C 0.15840(19) 0.0542(4) 0.81958(8) 0.0368(5) Uani 1 1 d . . . 
H20A H 0.0965 0.1393 0.8328 0.055 Uiso 1 1 calc R . . 
H20B H 0.1344 -0.0665 0.8302 0.055 Uiso 1 1 calc R . . 
H20C H 0.1594 0.0618 0.7790 0.055 Uiso 1 1 calc R . . 
C21A C 0.1902(2) -0.2584(4) 1.11413(9) 0.0418(6) Uani 1 1 d . . . 
H21A H 0.1968 -0.3736 1.0955 0.063 Uiso 1 1 calc R . . 
H21B H 0.1074 -0.2497 1.1306 0.063 Uiso 1 1 calc R . . 
H21C H 0.2586 -0.2475 1.1434 0.063 Uiso 1 1 calc R . . 
O1B O 0.63971(12) -0.2170(2) 0.56170(6) 0.0341(3) Uani 1 1 d . . . 
O2B O 0.69623(15) -0.3231(2) 0.46280(6) 0.0390(4) Uani 1 1 d . . . 
H2B H 0.6455 -0.3594 0.4859 0.058 Uiso 1 1 calc R . . 
O12B O 0.96207(13) 0.0800(2) 0.70857(6) 0.0313(3) Uani 1 1 d . . . 
O15B O 0.92593(17) -0.3705(3) 0.82481(7) 0.0571(5) Uani 1 1 d . . . 
O17B O 1.03879(13) 0.2983(2) 0.66003(6) 0.0378(4) Uani 1 1 d . . . 
O18B O 0.94326(15) 0.3755(3) 0.42962(8) 0.0681(7) Uani 1 1 d . . . 
O21B O 0.75199(12) 0.2999(2) 0.39342(6) 0.0348(4) Uani 1 1 d . . . 
C1B C 0.71922(16) -0.1243(3) 0.54115(8) 0.0245(4) Uani 1 1 d . . . 
C2B C 0.76845(18) -0.1799(3) 0.48595(8) 0.0286(4) Uani 1 1 d . . . 
H2B1 H 0.8584 -0.2215 0.4930 0.034 Uiso 1 1 calc R . . 
C3B C 0.76881(19) -0.0261(3) 0.44487(8) 0.0300(4) Uani 1 1 d . . . 
H3B1 H 0.6801 0.0041 0.4322 0.036 Uiso 1 1 calc R . . 
H3B2 H 0.8147 -0.0619 0.4119 0.036 Uiso 1 1 calc R . . 
C4B C 0.83346(17) 0.1364(3) 0.47200(8) 0.0278(4) Uani 1 1 d . . . 
H4B H 0.9212 0.0978 0.4852 0.033 Uiso 1 1 calc R . . 
C5B C 0.76680(17) 0.2002(3) 0.52478(8) 0.0252(4) Uani 1 1 d . . . 
C6B C 0.84228(18) 0.3560(3) 0.55173(8) 0.0305(4) Uani 1 1 d . . . 
H6B1 H 0.9339 0.3247 0.5547 0.037 Uiso 1 1 calc R . . 
H6B2 H 0.8319 0.4615 0.5273 0.037 Uiso 1 1 calc R . . 
C7B C 0.8004(2) 0.4039(3) 0.60941(8) 0.0344(5) Uani 1 1 d . . . 
H7B1 H 0.8539 0.5030 0.6246 0.041 Uiso 1 1 calc R . . 
H7B2 H 0.7110 0.4458 0.6060 0.041 Uiso 1 1 calc R . . 
C8B C 0.81053(18) 0.2481(3) 0.64997(8) 0.0282(4) Uani 1 1 d . . . 
H8B H 0.7644 0.2862 0.6831 0.034 Uiso 1 1 calc R . . 
C9B C 0.74085(17) 0.0768(3) 0.62751(8) 0.0249(4) Uani 1 1 d . . . 
C10B C 0.77762(16) 0.0421(3) 0.56691(7) 0.0225(4) Uani 1 1 d . . . 
H10B H 0.8710 0.0156 0.5708 0.027 Uiso 1 1 calc R . . 
C11B C 0.78948(18) -0.0851(3) 0.66289(7) 0.0270(4) Uani 1 1 d . . . 
H11C H 0.7170 -0.1654 0.6689 0.032 Uiso 1 1 calc R . . 
H11D H 0.8522 -0.1520 0.6421 0.032 Uiso 1 1 calc R . . 
C12B C 0.85103(18) -0.0300(3) 0.71881(8) 0.0281(4) Uani 1 1 d . . . 
H12B H 0.7890 0.0408 0.7396 0.034 Uiso 1 1 calc R . . 
C13B C 0.89776(17) -0.1836(3) 0.75345(8) 0.0293(4) Uani 1 1 d . . . 
C14B C 0.9803(2) -0.3245(3) 0.73833(9) 0.0404(6) Uani 1 1 d . . . 
H14B H 1.0180 -0.3388 0.7038 0.049 Uiso 1 1 calc R . . 
C15B C 0.9936(2) -0.4315(4) 0.78233(10) 0.0485(6) Uani 1 1 d . . . 
H15B H 1.0438 -0.5366 0.7839 0.058 Uiso 1 1 calc R . . 
C16B C 0.8684(2) -0.2187(4) 0.80584(9) 0.0419(6) Uani 1 1 d . . . 
H16B H 0.8146 -0.1469 0.8268 0.050 Uiso 1 1 calc R . . 
C17B C 0.94646(19) 0.2133(3) 0.67137(8) 0.0288(4) Uani 1 1 d . . . 
C18B C 0.85020(18) 0.2835(4) 0.43019(8) 0.0334(5) Uani 1 1 d . . . 
C19B C 0.62758(17) 0.2519(3) 0.50914(8) 0.0301(5) Uani 1 1 d . . . 
H19D H 0.5931 0.3181 0.5399 0.045 Uiso 1 1 calc R . . 
H19E H 0.5769 0.1441 0.5019 0.045 Uiso 1 1 calc R . . 
H19F H 0.6241 0.3264 0.4757 0.045 Uiso 1 1 calc R . . 
C20B C 0.59733(18) 0.1007(4) 0.63474(8) 0.0349(5) Uani 1 1 d . . . 
H20D H 0.5703 0.2182 0.6210 0.052 Uiso 1 1 calc R . . 
H20E H 0.5808 0.0906 0.6742 0.052 Uiso 1 1 calc R . . 
H20F H 0.5495 0.0086 0.6136 0.052 Uiso 1 1 calc R . . 
C21B C 0.7610(2) 0.4399(4) 0.35240(9) 0.0423(6) Uani 1 1 d . . . 
H21D H 0.7711 0.5549 0.3713 0.063 Uiso 1 1 calc R . . 
H21E H 0.6832 0.4415 0.3278 0.063 Uiso 1 1 calc R . . 
H21F H 0.8348 0.4180 0.3304 0.063 Uiso 1 1 calc R . . 
  
  
_geom_special_details 
; 
 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. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1A C1A 1.216(2) . ? 
O2A C2A 1.411(3) . ? 
O2A H2A 0.8400 . ? 
O12A C17A 1.357(3) . ? 
O12A C12A 1.448(2) . ? 
O15A C15A 1.350(3) . ? 
O15A C16A 1.367(3) . ? 
O17A C17A 1.198(3) . ? 
O18A C18A 1.199(3) . ? 
O21A C18A 1.331(2) . ? 
O21A C21A 1.446(3) . ? 
C1A C2A 1.510(3) . ? 
C1A C10A 1.512(3) . ? 
C2A C3A 1.523(3) . ? 
C2A H2A1 1.0000 . ? 
C3A C4A 1.527(3) . ? 
C3A H3A1 0.9900 . ? 
C3A H3A2 0.9900 . ? 
C4A C18A 1.518(3) . ? 
C4A C5A 1.566(3) . ? 
C4A H4A 1.0000 . ? 
C5A C6A 1.530(3) . ? 
C5A C19A 1.540(3) . ? 
C5A C10A 1.559(3) . ? 
C6A C7A 1.526(3) . ? 
C6A H6A1 0.9900 . ? 
C6A H6A2 0.9900 . ? 
C7A C8A 1.532(3) . ? 
C7A H7A1 0.9900 . ? 
C7A H7A2 0.9900 . ? 
C8A C17A 1.518(3) . ? 
C8A C9A 1.557(3) . ? 
C8A H8A 1.0000 . ? 
C9A C20A 1.537(3) . ? 
C9A C11A 1.547(3) . ? 
C9A C10A 1.557(3) . ? 
C10A H10A 1.0000 . ? 
C11A C12A 1.518(3) . ? 
C11A H11A 0.9900 . ? 
C11A H11B 0.9900 . ? 
C12A C13A 1.490(3) . ? 
C12A H12A 1.0000 . ? 
C13A C16A 1.330(3) . ? 
C13A C14A 1.419(3) . ? 
C14A C15A 1.327(4) . ? 
C14A H14A 0.9500 . ? 
C15A H15A 0.9500 . ? 
C16A H16A 0.9500 . ? 
C19A H19A 0.9800 . ? 
C19A H19B 0.9800 . ? 
C19A H19C 0.9800 . ? 
C20A H20A 0.9800 . ? 
C20A H20B 0.9800 . ? 
C20A H20C 0.9800 . ? 
C21A H21A 0.9800 . ? 
C21A H21B 0.9800 . ? 
C21A H21C 0.9800 . ? 
O1B C1B 1.216(2) . ? 
O2B C2B 1.412(3) . ? 
O2B H2B 0.8400 . ? 
O12B C17B 1.348(3) . ? 
O12B C12B 1.463(2) . ? 
O15B C16B 1.358(3) . ? 
O15B C15B 1.361(3) . ? 
O17B C17B 1.207(2) . ? 
O18B C18B 1.199(3) . ? 
O21B C18B 1.324(2) . ? 
O21B C21B 1.451(3) . ? 
C1B C10B 1.510(3) . ? 
C1B C2B 1.515(3) . ? 
C2B C3B 1.522(3) . ? 
C2B H2B1 1.0000 . ? 
C3B C4B 1.526(3) . ? 
C3B H3B1 0.9900 . ? 
C3B H3B2 0.9900 . ? 
C4B C18B 1.514(3) . ? 
C4B C5B 1.564(3) . ? 
C4B H4B 1.0000 . ? 
C5B C6B 1.536(3) . ? 
C5B C19B 1.538(3) . ? 
C5B C10B 1.563(3) . ? 
C6B C7B 1.525(3) . ? 
C6B H6B1 0.9900 . ? 
C6B H6B2 0.9900 . ? 
C7B C8B 1.525(3) . ? 
C7B H7B1 0.9900 . ? 
C7B H7B2 0.9900 . ? 
C8B C17B 1.512(3) . ? 
C8B C9B 1.562(3) . ? 
C8B H8B 1.0000 . ? 
C9B C20B 1.540(3) . ? 
C9B C10B 1.554(3) . ? 
C9B C11B 1.555(3) . ? 
C10B H10B 1.0000 . ? 
C11B C12B 1.515(3) . ? 
C11B H11C 0.9900 . ? 
C11B H11D 0.9900 . ? 
C12B C13B 1.491(3) . ? 
C12B H12B 1.0000 . ? 
C13B C16B 1.343(3) . ? 
C13B C14B 1.430(3) . ? 
C14B C15B 1.331(3) . ? 
C14B H14B 0.9500 . ? 
C15B H15B 0.9500 . ? 
C16B H16B 0.9500 . ? 
C19B H19D 0.9800 . ? 
C19B H19E 0.9800 . ? 
C19B H19F 0.9800 . ? 
C20B H20D 0.9800 . ? 
C20B H20E 0.9800 . ? 
C20B H20F 0.9800 . ? 
C21B H21D 0.9800 . ? 
C21B H21E 0.9800 . ? 
C21B H21F 0.9800 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C2A O2A H2A 109.5 . . ? 
C17A O12A C12A 117.08(16) . . ? 
C15A O15A C16A 105.9(2) . . ? 
C18A O21A C21A 116.67(17) . . ? 
O1A C1A C2A 119.0(2) . . ? 
O1A C1A C10A 125.43(18) . . ? 
C2A C1A C10A 115.53(16) . . ? 
O2A C2A C1A 110.87(18) . . ? 
O2A C2A C3A 110.60(17) . . ? 
C1A C2A C3A 110.94(18) . . ? 
O2A C2A H2A1 108.1 . . ? 
C1A C2A H2A1 108.1 . . ? 
C3A C2A H2A1 108.1 . . ? 
C2A C3A C4A 110.42(16) . . ? 
C2A C3A H3A1 109.6 . . ? 
C4A C3A H3A1 109.6 . . ? 
C2A C3A H3A2 109.6 . . ? 
C4A C3A H3A2 109.6 . . ? 
H3A1 C3A H3A2 108.1 . . ? 
C18A C4A C3A 111.70(17) . . ? 
C18A C4A C5A 112.31(18) . . ? 
C3A C4A C5A 112.64(16) . . ? 
C18A C4A H4A 106.6 . . ? 
C3A C4A H4A 106.6 . . ? 
C5A C4A H4A 106.6 . . ? 
C6A C5A C19A 112.02(18) . . ? 
C6A C5A C10A 107.01(15) . . ? 
C19A C5A C10A 112.54(16) . . ? 
C6A C5A C4A 109.23(16) . . ? 
C19A C5A C4A 110.30(16) . . ? 
C10A C5A C4A 105.47(16) . . ? 
C7A C6A C5A 113.82(17) . . ? 
C7A C6A H6A1 108.8 . . ? 
C5A C6A H6A1 108.8 . . ? 
C7A C6A H6A2 108.8 . . ? 
C5A C6A H6A2 108.8 . . ? 
H6A1 C6A H6A2 107.7 . . ? 
C6A C7A C8A 113.26(18) . . ? 
C6A C7A H7A1 108.9 . . ? 
C8A C7A H7A1 108.9 . . ? 
C6A C7A H7A2 108.9 . . ? 
C8A C7A H7A2 108.9 . . ? 
H7A1 C7A H7A2 107.7 . . ? 
C17A C8A C7A 112.42(18) . . ? 
C17A C8A C9A 112.82(18) . . ? 
C7A C8A C9A 113.63(16) . . ? 
C17A C8A H8A 105.7 . . ? 
C7A C8A H8A 105.7 . . ? 
C9A C8A H8A 105.7 . . ? 
C20A C9A C11A 109.24(17) . . ? 
C20A C9A C8A 106.92(18) . . ? 
C11A C9A C8A 109.19(15) . . ? 
C20A C9A C10A 115.86(16) . . ? 
C11A C9A C10A 106.89(16) . . ? 
C8A C9A C10A 108.63(16) . . ? 
C1A C10A C9A 113.52(16) . . ? 
C1A C10A C5A 110.41(15) . . ? 
C9A C10A C5A 117.66(17) . . ? 
C1A C10A H10A 104.6 . . ? 
C9A C10A H10A 104.6 . . ? 
C5A C10A H10A 104.6 . . ? 
C12A C11A C9A 112.08(18) . . ? 
C12A C11A H11A 109.2 . . ? 
C9A C11A H11A 109.2 . . ? 
C12A C11A H11B 109.2 . . ? 
C9A C11A H11B 109.2 . . ? 
H11A C11A H11B 107.9 . . ? 
O12A C12A C13A 108.53(16) . . ? 
O12A C12A C11A 108.57(15) . . ? 
C13A C12A C11A 111.91(19) . . ? 
O12A C12A H12A 109.3 . . ? 
C13A C12A H12A 109.3 . . ? 
C11A C12A H12A 109.3 . . ? 
C16A C13A C14A 105.3(2) . . ? 
C16A C13A C12A 128.9(2) . . ? 
C14A C13A C12A 125.7(2) . . ? 
C15A C14A C13A 107.4(2) . . ? 
C15A C14A H14A 126.3 . . ? 
C13A C14A H14A 126.3 . . ? 
C14A C15A O15A 110.4(2) . . ? 
C14A C15A H15A 124.8 . . ? 
O15A C15A H15A 124.8 . . ? 
C13A C16A O15A 111.0(2) . . ? 
C13A C16A H16A 124.5 . . ? 
O15A C16A H16A 124.5 . . ? 
O17A C17A O12A 118.92(19) . . ? 
O17A C17A C8A 125.6(2) . . ? 
O12A C17A C8A 115.44(18) . . ? 
O18A C18A O21A 123.6(2) . . ? 
O18A C18A C4A 124.38(19) . . ? 
O21A C18A C4A 111.99(18) . . ? 
C5A C19A H19A 109.5 . . ? 
C5A C19A H19B 109.5 . . ? 
H19A C19A H19B 109.5 . . ? 
C5A C19A H19C 109.5 . . ? 
H19A C19A H19C 109.5 . . ? 
H19B C19A H19C 109.5 . . ? 
C9A C20A H20A 109.5 . . ? 
C9A C20A H20B 109.5 . . ? 
H20A C20A H20B 109.5 . . ? 
C9A C20A H20C 109.5 . . ? 
H20A C20A H20C 109.5 . . ? 
H20B C20A H20C 109.5 . . ? 
O21A C21A H21A 109.5 . . ? 
O21A C21A H21B 109.5 . . ? 
H21A C21A H21B 109.5 . . ? 
O21A C21A H21C 109.5 . . ? 
H21A C21A H21C 109.5 . . ? 
H21B C21A H21C 109.5 . . ? 
C2B O2B H2B 109.5 . . ? 
C17B O12B C12B 117.79(15) . . ? 
C16B O15B C15B 105.84(18) . . ? 
C18B O21B C21B 116.25(17) . . ? 
O1B C1B C10B 125.45(18) . . ? 
O1B C1B C2B 118.58(19) . . ? 
C10B C1B C2B 115.95(16) . . ? 
O2B C2B C1B 110.67(16) . . ? 
O2B C2B C3B 110.22(15) . . ? 
C1B C2B C3B 112.01(17) . . ? 
O2B C2B H2B1 107.9 . . ? 
C1B C2B H2B1 107.9 . . ? 
C3B C2B H2B1 107.9 . . ? 
C2B C3B C4B 110.44(15) . . ? 
C2B C3B H3B1 109.6 . . ? 
C4B C3B H3B1 109.6 . . ? 
C2B C3B H3B2 109.6 . . ? 
C4B C3B H3B2 109.6 . . ? 
H3B1 C3B H3B2 108.1 . . ? 
C18B C4B C3B 111.58(16) . . ? 
C18B C4B C5B 113.09(18) . . ? 
C3B C4B C5B 112.58(16) . . ? 
C18B C4B H4B 106.3 . . ? 
C3B C4B H4B 106.3 . . ? 
C5B C4B H4B 106.3 . . ? 
C6B C5B C19B 111.69(17) . . ? 
C6B C5B C10B 106.91(14) . . ? 
C19B C5B C10B 112.44(15) . . ? 
C6B C5B C4B 109.39(16) . . ? 
C19B C5B C4B 110.20(15) . . ? 
C10B C5B C4B 105.99(16) . . ? 
C7B C6B C5B 113.24(17) . . ? 
C7B C6B H6B1 108.9 . . ? 
C5B C6B H6B1 108.9 . . ? 
C7B C6B H6B2 108.9 . . ? 
C5B C6B H6B2 108.9 . . ? 
H6B1 C6B H6B2 107.7 . . ? 
C8B C7B C6B 112.89(18) . . ? 
C8B C7B H7B1 109.0 . . ? 
C6B C7B H7B1 109.0 . . ? 
C8B C7B H7B2 109.0 . . ? 
C6B C7B H7B2 109.0 . . ? 
H7B1 C7B H7B2 107.8 . . ? 
C17B C8B C7B 112.25(17) . . ? 
C17B C8B C9B 112.87(17) . . ? 
C7B C8B C9B 113.51(15) . . ? 
C17B C8B H8B 105.8 . . ? 
C7B C8B H8B 105.8 . . ? 
C9B C8B H8B 105.8 . . ? 
C20B C9B C10B 115.30(15) . . ? 
C20B C9B C11B 108.73(16) . . ? 
C10B C9B C11B 106.90(16) . . ? 
C20B C9B C8B 107.83(17) . . ? 
C10B C9B C8B 109.00(16) . . ? 
C11B C9B C8B 108.94(14) . . ? 
C1B C10B C9B 114.00(16) . . ? 
C1B C10B C5B 110.62(14) . . ? 
C9B C10B C5B 117.98(16) . . ? 
C1B C10B H10B 104.2 . . ? 
C9B C10B H10B 104.2 . . ? 
C5B C10B H10B 104.2 . . ? 
C12B C11B C9B 112.39(17) . . ? 
C12B C11B H11C 109.1 . . ? 
C9B C11B H11C 109.1 . . ? 
C12B C11B H11D 109.1 . . ? 
C9B C11B H11D 109.1 . . ? 
H11C C11B H11D 107.9 . . ? 
O12B C12B C13B 107.05(15) . . ? 
O12B C12B C11B 107.85(15) . . ? 
C13B C12B C11B 113.16(18) . . ? 
O12B C12B H12B 109.6 . . ? 
C13B C12B H12B 109.6 . . ? 
C11B C12B H12B 109.6 . . ? 
C16B C13B C14B 105.7(2) . . ? 
C16B C13B C12B 126.2(2) . . ? 
C14B C13B C12B 128.02(18) . . ? 
C15B C14B C13B 106.3(2) . . ? 
C15B C14B H14B 126.8 . . ? 
C13B C14B H14B 126.8 . . ? 
C14B C15B O15B 111.1(2) . . ? 
C14B C15B H15B 124.5 . . ? 
O15B C15B H15B 124.5 . . ? 
C13B C16B O15B 111.0(2) . . ? 
C13B C16B H16B 124.5 . . ? 
O15B C16B H16B 124.5 . . ? 
O17B C17B O12B 118.50(18) . . ? 
O17B C17B C8B 125.98(19) . . ? 
O12B C17B C8B 115.43(18) . . ? 
O18B C18B O21B 122.8(2) . . ? 
O18B C18B C4B 123.89(18) . . ? 
O21B C18B C4B 113.29(17) . . ? 
C5B C19B H19D 109.5 . . ? 
C5B C19B H19E 109.5 . . ? 
H19D C19B H19E 109.5 . . ? 
C5B C19B H19F 109.5 . . ? 
H19D C19B H19F 109.5 . . ? 
H19E C19B H19F 109.5 . . ? 
C9B C20B H20D 109.5 . . ? 
C9B C20B H20E 109.5 . . ? 
H20D C20B H20E 109.5 . . ? 
C9B C20B H20F 109.5 . . ? 
H20D C20B H20F 109.5 . . ? 
H20E C20B H20F 109.5 . . ? 
O21B C21B H21D 109.5 . . ? 
O21B C21B H21E 109.5 . . ? 
H21D C21B H21E 109.5 . . ? 
O21B C21B H21F 109.5 . . ? 
H21D C21B H21F 109.5 . . ? 
H21E C21B H21F 109.5 . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
O1A C1A C2A O2A 5.6(3) . . . . ? 
C10A C1A C2A O2A -175.03(17) . . . . ? 
O1A C1A C2A C3A 128.9(2) . . . . ? 
C10A C1A C2A C3A -51.7(2) . . . . ? 
O2A C2A C3A C4A 174.66(18) . . . . ? 
C1A C2A C3A C4A 51.2(2) . . . . ? 
C2A C3A C4A C18A 173.34(17) . . . . ? 
C2A C3A C4A C5A -59.2(2) . . . . ? 
C18A C4A C5A C6A -57.1(2) . . . . ? 
C3A C4A C5A C6A 175.77(17) . . . . ? 
C18A C4A C5A C19A 66.5(2) . . . . ? 
C3A C4A C5A C19A -60.7(2) . . . . ? 
C18A C4A C5A C10A -171.77(16) . . . . ? 
C3A C4A C5A C10A 61.1(2) . . . . ? 
C19A C5A C6A C7A 70.2(2) . . . . ? 
C10A C5A C6A C7A -53.6(2) . . . . ? 
C4A C5A C6A C7A -167.29(17) . . . . ? 
C5A C6A C7A C8A 55.4(2) . . . . ? 
C6A C7A C8A C17A 78.2(2) . . . . ? 
C6A C7A C8A C9A -51.5(2) . . . . ? 
C17A C8A C9A C20A 152.33(17) . . . . ? 
C7A C8A C9A C20A -78.2(2) . . . . ? 
C17A C8A C9A C11A 34.3(2) . . . . ? 
C7A C8A C9A C11A 163.75(17) . . . . ? 
C17A C8A C9A C10A -82.0(2) . . . . ? 
C7A C8A C9A C10A 47.5(2) . . . . ? 
O1A C1A C10A C9A 10.1(3) . . . . ? 
C2A C1A C10A C9A -169.24(17) . . . . ? 
O1A C1A C10A C5A -124.5(2) . . . . ? 
C2A C1A C10A C5A 56.2(2) . . . . ? 
C20A C9A C10A C1A -62.1(2) . . . . ? 
C11A C9A C10A C1A 59.9(2) . . . . ? 
C8A C9A C10A C1A 177.59(16) . . . . ? 
C20A C9A C10A C5A 69.0(2) . . . . ? 
C11A C9A C10A C5A -169.01(15) . . . . ? 
C8A C9A C10A C5A -51.3(2) . . . . ? 
C6A C5A C10A C1A -173.53(15) . . . . ? 
C19A C5A C10A C1A 63.0(2) . . . . ? 
C4A C5A C10A C1A -57.29(19) . . . . ? 
C6A C5A C10A C9A 54.0(2) . . . . ? 
C19A C5A C10A C9A -69.5(2) . . . . ? 
C4A C5A C10A C9A 170.21(15) . . . . ? 
C20A C9A C11A C12A -97.4(2) . . . . ? 
C8A C9A C11A C12A 19.2(2) . . . . ? 
C10A C9A C11A C12A 136.58(16) . . . . ? 
C17A O12A C12A C13A 171.10(17) . . . . ? 
C17A O12A C12A C11A 49.2(2) . . . . ? 
C9A C11A C12A O12A -62.5(2) . . . . ? 
C9A C11A C12A C13A 177.74(16) . . . . ? 
O12A C12A C13A C16A -26.8(3) . . . . ? 
C11A C12A C13A C16A 93.0(3) . . . . ? 
O12A C12A C13A C14A 153.1(2) . . . . ? 
C11A C12A C13A C14A -87.1(3) . . . . ? 
C16A C13A C14A C15A -0.7(3) . . . . ? 
C12A C13A C14A C15A 179.4(2) . . . . ? 
C13A C14A C15A O15A 0.5(3) . . . . ? 
C16A O15A C15A C14A -0.2(3) . . . . ? 
C14A C13A C16A O15A 0.6(3) . . . . ? 
C12A C13A C16A O15A -179.5(2) . . . . ? 
C15A O15A C16A C13A -0.3(3) . . . . ? 
C12A O12A C17A O17A -176.46(19) . . . . ? 
C12A O12A C17A C8A 6.9(2) . . . . ? 
C7A C8A C17A O17A 2.1(3) . . . . ? 
C9A C8A C17A O17A 132.2(2) . . . . ? 
C7A C8A C17A O12A 178.53(17) . . . . ? 
C9A C8A C17A O12A -51.4(2) . . . . ? 
C21A O21A C18A O18A -3.8(3) . . . . ? 
C21A O21A C18A C4A 177.40(18) . . . . ? 
C3A C4A C18A O18A -140.6(3) . . . . ? 
C5A C4A C18A O18A 91.8(3) . . . . ? 
C3A C4A C18A O21A 38.2(3) . . . . ? 
C5A C4A C18A O21A -89.5(2) . . . . ? 
O1B C1B C2B O2B 9.0(2) . . . . ? 
C10B C1B C2B O2B -172.71(15) . . . . ? 
O1B C1B C2B C3B 132.47(18) . . . . ? 
C10B C1B C2B C3B -49.3(2) . . . . ? 
O2B C2B C3B C4B 173.45(15) . . . . ? 
C1B C2B C3B C4B 49.8(2) . . . . ? 
C2B C3B C4B C18B 172.78(16) . . . . ? 
C2B C3B C4B C5B -58.8(2) . . . . ? 
C18B C4B C5B C6B -56.0(2) . . . . ? 
C3B C4B C5B C6B 176.36(16) . . . . ? 
C18B C4B C5B C19B 67.1(2) . . . . ? 
C3B C4B C5B C19B -60.5(2) . . . . ? 
C18B C4B C5B C10B -170.97(15) . . . . ? 
C3B C4B C5B C10B 61.43(19) . . . . ? 
C19B C5B C6B C7B 69.0(2) . . . . ? 
C10B C5B C6B C7B -54.3(2) . . . . ? 
C4B C5B C6B C7B -168.69(16) . . . . ? 
C5B C6B C7B C8B 57.5(2) . . . . ? 
C6B C7B C8B C17B 76.6(2) . . . . ? 
C6B C7B C8B C9B -52.8(2) . . . . ? 
C17B C8B C9B C20B 152.05(16) . . . . ? 
C7B C8B C9B C20B -78.8(2) . . . . ? 
C17B C8B C9B C10B -82.11(19) . . . . ? 
C7B C8B C9B C10B 47.1(2) . . . . ? 
C17B C8B C9B C11B 34.2(2) . . . . ? 
C7B C8B C9B C11B 163.38(16) . . . . ? 
O1B C1B C10B C9B 7.6(3) . . . . ? 
C2B C1B C10B C9B -170.55(15) . . . . ? 
O1B C1B C10B C5B -128.19(19) . . . . ? 
C2B C1B C10B C5B 53.7(2) . . . . ? 
C20B C9B C10B C1B -60.5(2) . . . . ? 
C11B C9B C10B C1B 60.51(19) . . . . ? 
C8B C9B C10B C1B 178.12(14) . . . . ? 
C20B C9B C10B C5B 71.8(2) . . . . ? 
C11B C9B C10B C5B -167.18(15) . . . . ? 
C8B C9B C10B C5B -49.6(2) . . . . ? 
C6B C5B C10B C1B -173.30(15) . . . . ? 
C19B C5B C10B C1B 63.8(2) . . . . ? 
C4B C5B C10B C1B -56.68(18) . . . . ? 
C6B C5B C10B C9B 52.9(2) . . . . ? 
C19B C5B C10B C9B -70.0(2) . . . . ? 
C4B C5B C10B C9B 169.53(15) . . . . ? 
C20B C9B C11B C12B -97.43(19) . . . . ? 
C10B C9B C11B C12B 137.49(16) . . . . ? 
C8B C9B C11B C12B 19.8(2) . . . . ? 
C17B O12B C12B C13B 170.59(16) . . . . ? 
C17B O12B C12B C11B 48.5(2) . . . . ? 
C9B C11B C12B O12B -62.0(2) . . . . ? 
C9B C11B C12B C13B 179.75(16) . . . . ? 
O12B C12B C13B C16B 115.1(2) . . . . ? 
C11B C12B C13B C16B -126.2(2) . . . . ? 
O12B C12B C13B C14B -65.9(3) . . . . ? 
C11B C12B C13B C14B 52.7(3) . . . . ? 
C16B C13B C14B C15B 0.0(3) . . . . ? 
C12B C13B C14B C15B -179.1(2) . . . . ? 
C13B C14B C15B O15B 0.0(3) . . . . ? 
C16B O15B C15B C14B 0.0(3) . . . . ? 
C14B C13B C16B O15B 0.0(3) . . . . ? 
C12B C13B C16B O15B 179.13(19) . . . . ? 
C15B O15B C16B C13B 0.0(3) . . . . ? 
C12B O12B C17B O17B -175.62(18) . . . . ? 
C12B O12B C17B C8B 7.6(2) . . . . ? 
C7B C8B C17B O17B 1.9(3) . . . . ? 
C9B C8B C17B O17B 131.7(2) . . . . ? 
C7B C8B C17B O12B 178.40(16) . . . . ? 
C9B C8B C17B O12B -51.8(2) . . . . ? 
C21B O21B C18B O18B -1.5(3) . . . . ? 
C21B O21B C18B C4B 179.35(19) . . . . ? 
C3B C4B C18B O18B -140.4(2) . . . . ? 
C5B C4B C18B O18B 91.5(3) . . . . ? 
C3B C4B C18B O21B 38.8(2) . . . . ? 
C5B C4B C18B O21B -89.3(2) . . . . ? 
  
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O2A H2A O1A  0.84 2.12 2.618(2) 117.4 . 
O2B H2B O1B  0.84 2.12 2.614(2) 117.4 . 
  
_diffrn_measured_fraction_theta_max    0.996 
_diffrn_reflns_theta_full              27.88 
_diffrn_measured_fraction_theta_full   0.996 
_refine_diff_density_max    0.216 
_refine_diff_density_min   -0.274 
_refine_diff_density_rms    0.047 

_chemical_compound_source        
'Na2CO3/MeOH treatment of salvinorin A from Salvia divinorum leaves'
_exptl_crystal_recrystallization_method 
'slow evaporation from EtOAc at rt in a fume hood'

