# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c13h18o2

_audit_creation_date             2014-06-02T15:03:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
'(3RS,6RS,6aRS,11bRS)-8,11-dimethoxy-6a-methyl-2-oxo-3,4,5,6,6a,7-hexahydro-2H-3,11b-methanoindeno[1,2-b]oxocin-6-yl methanesulfonate (16)'
_chemical_formula_moiety         'C13 H18 O2'
_chemical_formula_sum            'C26 H36 O4'
_chemical_formula_weight         412.55
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -x,y,1/2-z
3 1/2+x,1/2+y,z
4 1/2-x,1/2+y,1/2-z
5 -x,-y,-z
6 x,-y,1/2+z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z
_cell_length_a                   9.001(11)
_cell_length_b                   11.207(13)
_cell_length_c                   20.96(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.919(14)
_cell_angle_gamma                90
_cell_volume                     2114(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    2531
_cell_measurement_theta_min      3.0498
_cell_measurement_theta_max      27.47
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_source                   'sealed x-ray tube'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 14.7059
_diffrn_measurement_device       'quarter Χ-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_number            15219
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.073
_diffrn_reflns_theta_max         27.787
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_ful 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.968
_reflns_number_total             2429
_reflns_number_gt                1853
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        
'CrystalClear (Rigaku Inc., 2007), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2429
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1542
_refine_ls_R_factor_gt           0.1327
_refine_ls_wR_factor_ref         0.4116
_refine_ls_wR_factor_gt          0.3926
_refine_ls_goodness_of_fit_ref   1.594
_refine_ls_restrained_S_all      1.594
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.947
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.112

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1188(4) 0.6033(3) 0.86651(18) 0.0315(9) Uani 1 d . .
C2 C 0.0825(4) 0.7294(3) 0.83975(19) 0.0323(9) Uani 1 d . .
H2 H 0.0063 0.719 0.805 0.039 Uiso 1 calc . .
C3 C 0.0121(4) 0.8039(3) 0.89155(19) 0.0339(9) Uani 1 d . .
C4 C 0.3566(4) 0.6966(3) 0.8192(2) 0.0385(10) Uani 1 d . .
H4 H 0.4488 0.7326 0.8015 0.046 Uiso 1 calc . .
C5 C -0.0218(4) 0.5492(3) 0.89314(19) 0.0350(9) Uani 1 d . .
H5A H -0.0936 0.5358 0.8576 0.042 Uiso 1 calc . .
H5B H 0.0026 0.4705 0.912 0.042 Uiso 1 calc . .
C6 C -0.1279(4) 0.7497(3) 0.9178(2) 0.0357(9) Uani 1 d . .
H6 H -0.167 0.8009 0.9528 0.043 Uiso 1 calc . .
C7 C 0.2233(4) 0.7814(3) 0.8089(2) 0.0396(10) Uani 1 d . .
H7A H 0.205 0.793 0.7626 0.048 Uiso 1 calc . .
H7B H 0.2463 0.8601 0.828 0.048 Uiso 1 calc . .
C8 C -0.0944(4) 0.6254(3) 0.9430(2) 0.0399(10) Uani 1 d . .
H8A H -0.0278 0.6314 0.9809 0.048 Uiso 1 calc . .
H8B H -0.188 0.587 0.9564 0.048 Uiso 1 calc . .
C9 C 0.1802(5) 0.5282(3) 0.8126(2) 0.0411(10) Uani 1 d . .
H9A H 0.1977 0.4459 0.8281 0.049 Uiso 1 calc . .
H9B H 0.1058 0.5243 0.7773 0.049 Uiso 1 calc . .
C10 C 0.2419(4) 0.6163(3) 0.91758(19) 0.0367(9) Uani 1 d . .
H10A H 0.2052 0.6644 0.9537 0.044 Uiso 1 calc . .
H10B H 0.2705 0.5367 0.934 0.044 Uiso 1 calc . .
C11 C 0.3747(4) 0.6764(3) 0.8889(2) 0.0382(9) Uani 1 d . .
C12 C 0.3239(5) 0.5785(3) 0.7875(2) 0.0445(11) Uani 1 d . .
H12A H 0.4062 0.522 0.7964 0.053 Uiso 1 calc . .
H12B H 0.3154 0.5895 0.7407 0.053 Uiso 1 calc . .
C13 C 0.0677(5) 0.9028(3) 0.9170(2) 0.0473(11) Uani 1 d . .
H13A H 0.0195 0.9398 0.9518 0.057 Uiso 1 calc . .
H13B H 0.1558 0.9367 0.9004 0.057 Uiso 1 calc . .
O1 O 0.4871(3) 0.6998(2) 0.92049(15) 0.0432(8) Uani 1 d . .
O2 O -0.2353(3) 0.7429(3) 0.86608(15) 0.0451(8) Uani 1 d . .
H2A H -0.1978 0.7071 0.835 0.068 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C5 1.517(5) . ?
C1 C9 1.521(5) . ?
C1 C10 1.535(5) . ?
C1 C2 1.553(5) . ?
C2 C3 1.517(5) . ?
C2 C7 1.546(5) . ?
C2 H2 1 . ?
C3 C13 1.324(5) . ?
C3 C6 1.511(5) . ?
C4 C11 1.485(6) . ?
C4 C12 1.508(6) . ?
C4 C7 1.543(6) . ?
C4 H4 1 . ?
C5 C8 1.507(5) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 O2 1.443(5) . ?
C6 C8 1.519(5) . ?
C6 H6 1 . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C12 1.513(6) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.506(5) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 O1 1.228(5) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 H13A 0.95 . ?
C13 H13B 0.95 . ?
O2 H2A 0.84 . ?

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
C5 C1 C9 111.6(3) . . ?
C5 C1 C10 112.2(3) . . ?
C9 C1 C10 107.7(3) . . ?
C5 C1 C2 109.0(3) . . ?
C9 C1 C2 108.2(3) . . ?
C10 C1 C2 108.1(3) . . ?
C3 C2 C7 116.5(3) . . ?
C3 C2 C1 109.3(3) . . ?
C7 C2 C1 109.0(3) . . ?
C3 C2 H2 107.2 . . ?
C7 C2 H2 107.2 . . ?
C1 C2 H2 107.2 . . ?
C13 C3 C6 120.2(4) . . ?
C13 C3 C2 126.1(4) . . ?
C6 C3 C2 113.5(3) . . ?
C11 C4 C12 108.5(3) . . ?
C11 C4 C7 107.7(3) . . ?
C12 C4 C7 109.4(4) . . ?
C11 C4 H4 110.4 . . ?
C12 C4 H4 110.4 . . ?
C7 C4 H4 110.4 . . ?
C8 C5 C1 113.7(3) . . ?
C8 C5 H5A 108.8 . . ?
C1 C5 H5A 108.8 . . ?
C8 C5 H5B 108.8 . . ?
C1 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
O2 C6 C3 107.5(3) . . ?
O2 C6 C8 109.9(3) . . ?
C3 C6 C8 109.5(3) . . ?
O2 C6 H6 110 . . ?
C3 C6 H6 110 . . ?
C8 C6 H6 110 . . ?
C4 C7 C2 110.5(3) . . ?
C4 C7 H7A 109.6 . . ?
C2 C7 H7A 109.6 . . ?
C4 C7 H7B 109.6 . . ?
C2 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C5 C8 C6 111.3(3) . . ?
C5 C8 H8A 109.4 . . ?
C6 C8 H8A 109.4 . . ?
C5 C8 H8B 109.4 . . ?
C6 C8 H8B 109.4 . . ?
H8A C8 H8B 108 . . ?
C12 C9 C1 112.0(3) . . ?
C12 C9 H9A 109.2 . . ?
C1 C9 H9A 109.2 . . ?
C12 C9 H9B 109.2 . . ?
C1 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C1 109.5(3) . . ?
C11 C10 H10A 109.8 . . ?
C1 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
C1 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
O1 C11 C4 125.0(4) . . ?
O1 C11 C10 122.2(4) . . ?
C4 C11 C10 112.7(3) . . ?
C4 C12 C9 109.7(3) . . ?
C4 C12 H12A 109.7 . . ?
C9 C12 H12A 109.7 . . ?
C4 C12 H12B 109.7 . . ?
C9 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C3 C13 H13A 120 . . ?
C3 C13 H13B 120 . . ?
H13A C13 H13B 120 . . ?
C6 O2 H2A 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
C5 C1 C2 C3 55.1(4) . . . . ?
C9 C1 C2 C3 176.5(3) . . . . ?
C10 C1 C2 C3 -67.1(4) . . . . ?
C5 C1 C2 C7 -176.6(3) . . . . ?
C9 C1 C2 C7 -55.1(4) . . . . ?
C10 C1 C2 C7 61.2(4) . . . . ?
C7 C2 C3 C13 -7.1(6) . . . . ?
C1 C2 C3 C13 116.9(4) . . . . ?
C7 C2 C3 C6 177.9(3) . . . . ?
C1 C2 C3 C6 -58.1(4) . . . . ?
C9 C1 C5 C8 -175.2(3) . . . . ?
C10 C1 C5 C8 63.8(4) . . . . ?
C2 C1 C5 C8 -55.8(4) . . . . ?
C13 C3 C6 O2 122.2(4) . . . . ?
C2 C3 C6 O2 -62.5(4) . . . . ?
C13 C3 C6 C8 -118.4(4) . . . . ?
C2 C3 C6 C8 56.9(4) . . . . ?
C11 C4 C7 C2 -56.1(4) . . . . ?
C12 C4 C7 C2 61.7(4) . . . . ?
C3 C2 C7 C4 119.7(4) . . . . ?
C1 C2 C7 C4 -4.5(4) . . . . ?
C1 C5 C8 C6 55.8(4) . . . . ?
O2 C6 C8 C5 64.2(4) . . . . ?
C3 C6 C8 C5 -53.7(4) . . . . ?
C5 C1 C9 C12 -177.6(3) . . . . ?
C10 C1 C9 C12 -54.0(4) . . . . ?
C2 C1 C9 C12 62.6(4) . . . . ?
C5 C1 C10 C11 -177.0(3) . . . . ?
C9 C1 C10 C11 59.9(4) . . . . ?
C2 C1 C10 C11 -56.8(4) . . . . ?
C12 C4 C11 O1 120.7(4) . . . . ?
C7 C4 C11 O1 -120.9(4) . . . . ?
C12 C4 C11 C10 -56.0(4) . . . . ?
C7 C4 C11 C10 62.4(4) . . . . ?
C1 C10 C11 O1 178.2(3) . . . . ?
C1 C10 C11 C4 -5.1(4) . . . . ?
C11 C4 C12 C9 61.6(4) . . . . ?
C7 C4 C12 C9 -55.6(5) . . . . ?
C1 C9 C12 C4 -5.7(5) . . . . ?

# END of CIF
_chemical_melting_point          383.15
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
_database_code_depnum_ccdc_archive 'CCDC 1022475'
