# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kno84-abs
_database_code_depnum_ccdc_archive 'CCDC 1526876'
_audit_update_record             
;
2017-01-11 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        (--)-(2R,7R,8R)-Sarcophytoxide
_chemical_name_common            ?
_chemical_melting_point          '333--334 \%C'
_chemical_formula_moiety         'C20 H30 O2'
_chemical_formula_sum            'C20 H30 O2'
_chemical_formula_weight         302.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.6825(3)
_cell_length_b                   14.2013(7)
_cell_length_c                   11.4613(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.933(2)
_cell_angle_gamma                90
_cell_volume                     921.49(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9602
_cell_measurement_theta_min      3.87
_cell_measurement_theta_max      68.14

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   0.3933
_exptl_transmission_factor_max   0.5213
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.526
_shelx_estimated_absorpt_T_min   0.798
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus X-ray tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_device       'Bruker AXS Kappa Apex Duo'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31136
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.871
_diffrn_reflns_theta_max         68.720
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3258
_reflns_number_gt                3249
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_max     0.933
_reflns_Friedel_fraction_full    0.946

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.0695P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0065(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1505 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3258
_refine_ls_number_parameters     204
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.047
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8704(3) 0.76263(12) 0.50733(13) 0.0398(3) Uani 1 1 d . . . . .
C2 C 0.8656(3) 0.86519(12) 0.54050(14) 0.0415(4) Uani 1 1 d . . . . .
H2A H 0.7022 0.8906 0.5231 0.050 Uiso 1 1 calc R U . . .
C3 C 0.9484(3) 0.88483(11) 0.66567(15) 0.0412(4) Uani 1 1 d . . . . .
H3A H 1.1009 0.8617 0.6917 0.049 Uiso 1 1 calc R U . . .
C4 C 0.8342(3) 0.93072(11) 0.74492(14) 0.0423(4) Uani 1 1 d . . . . .
C5 C 0.9468(4) 0.94517(14) 0.86775(16) 0.0543(5) Uani 1 1 d . . . . .
H5A H 0.9627 1.0136 0.8827 0.065 Uiso 1 1 calc R U . . .
H5B H 1.1077 0.9179 0.8731 0.065 Uiso 1 1 calc R U . . .
C6 C 0.8093(3) 0.90113(15) 0.96400(15) 0.0551(5) Uani 1 1 d . . . . .
H6A H 0.8789 0.9234 1.0413 0.066 Uiso 1 1 calc R U . . .
H6B H 0.6437 0.9233 0.9540 0.066 Uiso 1 1 calc R U . . .
C7 C 0.8109(3) 0.79550(14) 0.96294(14) 0.0453(4) Uani 1 1 d . . . . .
H7A H 0.8424 0.7662 0.8865 0.054 Uiso 1 1 calc R U . . .
C8 C 0.6710(3) 0.73749(14) 1.03771(13) 0.0453(4) Uani 1 1 d . . . . .
C9 C 0.5990(3) 0.63976(14) 0.99924(16) 0.0513(4) Uani 1 1 d . . . . .
H9A H 0.5781 0.6010 1.0694 0.062 Uiso 1 1 calc R U . . .
H9B H 0.7278 0.6113 0.9581 0.062 Uiso 1 1 calc R U . . .
C10 C 0.3689(3) 0.63699(14) 0.91762(17) 0.0515(4) Uani 1 1 d . . . . .
H10A H 0.3209 0.5707 0.9032 0.062 Uiso 1 1 calc R U . . .
H10B H 0.2415 0.6690 0.9561 0.062 Uiso 1 1 calc R U . . .
C11 C 0.4011(3) 0.68433(12) 0.80320(14) 0.0434(4) Uani 1 1 d . . . . .
H11A H 0.3916 0.7511 0.8030 0.052 Uiso 1 1 calc R U . . .
C12 C 0.4412(3) 0.64440(13) 0.70243(17) 0.0480(4) Uani 1 1 d . . . . .
C13 C 0.5105(3) 0.70278(13) 0.60152(15) 0.0470(4) Uani 1 1 d . . . . .
H13A H 0.4803 0.7701 0.6172 0.056 Uiso 1 1 calc R U . . .
H13B H 0.4123 0.6846 0.5295 0.056 Uiso 1 1 calc R U . . .
C14 C 0.7726(3) 0.68922(12) 0.58240(14) 0.0424(4) Uani 1 1 d . . . . .
H14A H 0.8653 0.6891 0.6596 0.051 Uiso 1 1 calc R U . . .
H14B H 0.7927 0.6268 0.5460 0.051 Uiso 1 1 calc R U . . .
C15 C 0.9802(3) 0.75271(14) 0.41001(13) 0.0465(4) Uani 1 1 d . . . . .
C16 C 1.0683(4) 0.84590(15) 0.37320(16) 0.0559(5) Uani 1 1 d . . . . .
H16A H 1.2396 0.8429 0.3633 0.067 Uiso 1 1 calc R U . . .
H16B H 0.9838 0.8660 0.2982 0.067 Uiso 1 1 calc R U . . .
O17 O 1.0231(3) 0.90988(9) 0.46499(11) 0.0558(3) Uani 1 1 d . . . . .
C18 C 1.0266(4) 0.66510(16) 0.34387(16) 0.0617(6) Uani 1 1 d . . . . .
H18A H 0.9585 0.6110 0.3820 0.093 Uiso 1 1 calc R U . . .
H18B H 1.1974 0.6561 0.3428 0.093 Uiso 1 1 calc R U . . .
H18C H 0.9544 0.6706 0.2634 0.093 Uiso 1 1 calc R U . . .
C19 C 0.5920(3) 0.97305(13) 0.72086(18) 0.0522(4) Uani 1 1 d . . . . .
H19A H 0.5487 0.9738 0.6362 0.078 Uiso 1 1 calc R U . . .
H19B H 0.5926 1.0376 0.7512 0.078 Uiso 1 1 calc R U . . .
H19C H 0.4770 0.9353 0.7595 0.078 Uiso 1 1 calc R U . . .
O20 O 0.92314(19) 0.74920(12) 1.06567(10) 0.0589(4) Uani 1 1 d . . . . .
C21 C 0.5215(3) 0.78300(17) 1.12471(17) 0.0596(5) Uani 1 1 d . . . . .
H21A H 0.5851 0.8454 1.1458 0.089 Uiso 1 1 calc R U . . .
H21B H 0.5235 0.7438 1.1951 0.089 Uiso 1 1 calc R U . . .
H21C H 0.3588 0.7893 1.0897 0.089 Uiso 1 1 calc R U . . .
C22 C 0.4360(6) 0.54030(16) 0.6818(3) 0.0918(9) Uani 1 1 d . . . . .
H22A H 0.3254 0.5260 0.6138 0.138 Uiso 1 1 calc R U . . .
H22B H 0.3849 0.5083 0.7510 0.138 Uiso 1 1 calc R U . . .
H22C H 0.5944 0.5185 0.6671 0.138 Uiso 1 1 calc R U . . .


_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
C1 C15 1.331(2) . ?
C1 C14 1.489(2) . ?
C1 C2 1.506(2) . ?
C2 O17 1.444(2) . ?
C2 C3 1.497(2) . ?
C2 H2A 1.0000 . ?
C3 C4 1.331(2) . ?
C3 H3A 0.9500 . ?
C4 C19 1.506(3) . ?
C4 C5 1.509(3) . ?
C5 C6 1.538(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.500(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O20 1.448(2) . ?
C7 C8 1.470(2) . ?
C7 H7A 1.0000 . ?
C8 O20 1.4507(19) . ?
C8 C9 1.502(3) . ?
C8 C21 1.510(2) . ?
C9 C10 1.542(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.499(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.324(3) . ?
C11 H11A 0.9500 . ?
C12 C22 1.497(3) . ?
C12 C13 1.503(3) . ?
C13 C14 1.536(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.489(3) . ?
C15 C18 1.492(3) . ?
C16 O17 1.430(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C15 C1 C14 129.42(17) . . ?
C15 C1 C2 109.49(16) . . ?
C14 C1 C2 121.02(13) . . ?
O17 C2 C3 109.42(14) . . ?
O17 C2 C1 104.37(13) . . ?
C3 C2 C1 114.27(13) . . ?
O17 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C4 C3 C2 127.85(16) . . ?
C4 C3 H3A 116.1 . . ?
C2 C3 H3A 116.1 . . ?
C3 C4 C19 124.20(16) . . ?
C3 C4 C5 120.71(16) . . ?
C19 C4 C5 115.08(16) . . ?
C4 C5 C6 114.40(14) . . ?
C4 C5 H5A 108.7 . . ?
C6 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C7 C6 C5 113.39(15) . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O20 C7 C8 59.61(10) . . ?
O20 C7 C6 116.74(15) . . ?
C8 C7 C6 123.47(15) . . ?
O20 C7 H7A 115.1 . . ?
C8 C7 H7A 115.1 . . ?
C6 C7 H7A 115.1 . . ?
O20 C8 C7 59.42(10) . . ?
O20 C8 C9 114.17(15) . . ?
C7 C8 C9 119.58(14) . . ?
O20 C8 C21 113.97(15) . . ?
C7 C8 C21 120.55(17) . . ?
C9 C8 C21 115.78(16) . . ?
C8 C9 C10 113.39(15) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 110.99(15) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 127.90(17) . . ?
C12 C11 H11A 116.1 . . ?
C10 C11 H11A 116.1 . . ?
C11 C12 C22 123.9(2) . . ?
C11 C12 C13 120.74(16) . . ?
C22 C12 C13 115.23(19) . . ?
C12 C13 C14 111.22(14) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C1 C14 C13 114.16(14) . . ?
C1 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C1 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C1 C15 C16 109.68(16) . . ?
C1 C15 C18 129.04(19) . . ?
C16 C15 C18 121.24(16) . . ?
O17 C16 C15 105.67(14) . . ?
O17 C16 H16A 110.6 . . ?
C15 C16 H16A 110.6 . . ?
O17 C16 H16B 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
C16 O17 C2 108.75(14) . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 O20 C8 60.97(10) . . ?
C8 C21 H21A 109.5 . . ?
C8 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C8 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C22 H22A 109.5 . . ?
C12 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C12 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C15 C1 C2 O17 -10.67(17) . . . . ?
C14 C1 C2 O17 166.47(13) . . . . ?
C15 C1 C2 C3 -130.14(15) . . . . ?
C14 C1 C2 C3 47.0(2) . . . . ?
O17 C2 C3 C4 118.32(18) . . . . ?
C1 C2 C3 C4 -125.10(18) . . . . ?
C2 C3 C4 C19 -0.4(3) . . . . ?
C2 C3 C4 C5 -179.21(16) . . . . ?
C3 C4 C5 C6 -119.58(19) . . . . ?
C19 C4 C5 C6 61.5(2) . . . . ?
C4 C5 C6 C7 68.6(2) . . . . ?
C5 C6 C7 O20 117.14(16) . . . . ?
C5 C6 C7 C8 -173.10(15) . . . . ?
C6 C7 C8 O20 -103.75(18) . . . . ?
O20 C7 C8 C9 -102.20(17) . . . . ?
C6 C7 C8 C9 154.05(16) . . . . ?
O20 C7 C8 C21 101.49(18) . . . . ?
C6 C7 C8 C21 -2.3(2) . . . . ?
O20 C8 C9 C10 -152.79(14) . . . . ?
C7 C8 C9 C10 -85.52(19) . . . . ?
C21 C8 C9 C10 71.9(2) . . . . ?
C8 C9 C10 C11 65.9(2) . . . . ?
C9 C10 C11 C12 99.3(2) . . . . ?
C10 C11 C12 C22 6.9(3) . . . . ?
C10 C11 C12 C13 -169.41(16) . . . . ?
C11 C12 C13 C14 107.05(19) . . . . ?
C22 C12 C13 C14 -69.6(2) . . . . ?
C15 C1 C14 C13 -124.85(18) . . . . ?
C2 C1 C14 C13 58.64(19) . . . . ?
C12 C13 C14 C1 -164.12(14) . . . . ?
C14 C1 C15 C16 -173.99(15) . . . . ?
C2 C1 C15 C16 2.84(19) . . . . ?
C14 C1 C15 C18 3.5(3) . . . . ?
C2 C1 C15 C18 -179.64(17) . . . . ?
C1 C15 C16 O17 6.2(2) . . . . ?
C18 C15 C16 O17 -171.53(16) . . . . ?
C15 C16 O17 C2 -13.04(18) . . . . ?
C3 C2 O17 C16 137.17(15) . . . . ?
C1 C2 O17 C16 14.47(17) . . . . ?
C6 C7 O20 C8 114.86(18) . . . . ?
C9 C8 O20 C7 111.30(16) . . . . ?
C21 C8 O20 C7 -112.54(19) . . . . ?

_refine_diff_density_max         0.123
_refine_diff_density_min         -0.084
_refine_diff_density_rms         0.021

_shelxl_version_number           2014/6


_chemical_compound_source        'Sarcophyton stellatum'
