# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_mml145_0m
_database_code_depnum_ccdc_archive 'CCDC 1052072'
_audit_update_record             
;
2015-03-03 deposited with the CCDC.
2015-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H32 Br2 S2'
_chemical_formula_weight         664.53

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.3927(7)
_cell_length_b                   11.1410(5)
_cell_length_c                   18.1915(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.2897(16)
_cell_angle_gamma                90
_cell_volume                     3023.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9725
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.64

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.841
_shelx_estimated_absorpt_T_min   0.644
_shelx_estimated_absorpt_T_max   0.764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7462
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'high brilliance microfocus sealed tube '
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            100925
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.162
_diffrn_reflns_theta_max         28.778
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7835
_reflns_number_gt                6768
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 2014.1-1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2011)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0394P)²+2.0778P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7835
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.004
_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
Br1 Br 0.47840(2) 0.08208(2) 1.09678(2) 0.03533(6) Uani 1 1 d . . . . .
Br2 Br 1.23987(2) 0.81894(2) 0.70893(2) 0.03800(7) Uani 1 1 d . . . . .
S1 S 0.71961(3) 0.48307(3) 0.92413(2) 0.01704(8) Uani 1 1 d . . . . .
S2 S 0.93328(3) 0.49675(3) 0.87036(2) 0.01744(8) Uani 1 1 d . . . . .
C1 C 0.73861(10) 0.63189(13) 0.88658(8) 0.0136(3) Uani 1 1 d . . . . .
H1 H 0.6803 0.6756 0.8705 0.016 Uiso 1 1 calc R U . . .
C2 C 0.78253(10) 0.62510(13) 0.81990(8) 0.0128(3) Uani 1 1 d . . . . .
C3 C 0.88307(10) 0.64762(13) 0.85266(8) 0.0137(3) Uani 1 1 d . . . . .
H3 H 0.9098 0.6950 0.8170 0.016 Uiso 1 1 calc R U . . .
C4 C 0.88491(10) 0.71624(14) 0.92456(8) 0.0152(3) Uani 1 1 d . . . . .
C5 C 0.95220(11) 0.78889(16) 0.96724(10) 0.0217(3) Uani 1 1 d . . . . .
H5 H 1.0077 0.7977 0.9537 0.026 Uiso 1 1 calc R U . . .
C6 C 0.93693(12) 0.84854(18) 1.03012(10) 0.0276(4) Uani 1 1 d . . . . .
H6 H 0.9823 0.8986 1.0597 0.033 Uiso 1 1 calc R U . . .
C7 C 0.85571(12) 0.83546(18) 1.04996(10) 0.0274(4) Uani 1 1 d . . . . .
H7 H 0.8464 0.8762 1.0932 0.033 Uiso 1 1 calc R U . . .
C8 C 0.78826(11) 0.76361(16) 1.00722(9) 0.0209(3) Uani 1 1 d . . . . .
H8 H 0.7329 0.7545 1.0209 0.025 Uiso 1 1 calc R U . . .
C9 C 0.80336(10) 0.70532(14) 0.94415(8) 0.0149(3) Uani 1 1 d . . . . .
C10 C 0.73461(10) 0.60681(13) 0.74820(8) 0.0125(3) Uani 1 1 d . . . . .
C11 C 0.76559(10) 0.59935(14) 0.67418(9) 0.0151(3) Uani 1 1 d . . . . .
C12 C 0.70280(13) 0.6753(2) 0.61281(10) 0.0302(4) Uani 1 1 d . . . . .
H12A H 0.7020 0.7581 0.6308 0.045 Uiso 1 1 calc R U . . .
H12B H 0.6421 0.6419 0.6021 0.045 Uiso 1 1 calc R U . . .
H12C H 0.7243 0.6742 0.5664 0.045 Uiso 1 1 calc R U . . .
C13 C 0.75948(14) 0.46844(16) 0.64740(11) 0.0292(4) Uani 1 1 d . . . . .
H13A H 0.7819 0.4620 0.6016 0.044 Uiso 1 1 calc R U . . .
H13B H 0.6969 0.4419 0.6361 0.044 Uiso 1 1 calc R U . . .
H13C H 0.7958 0.4177 0.6874 0.044 Uiso 1 1 calc R U . . .
C14 C 0.86134(11) 0.64304(15) 0.67990(9) 0.0183(3) Uani 1 1 d . . . . .
H14A H 0.8666 0.7274 0.6956 0.027 Uiso 1 1 calc R U . . .
H14B H 0.8752 0.6352 0.6304 0.027 Uiso 1 1 calc R U . . .
H14C H 0.9035 0.5945 0.7174 0.027 Uiso 1 1 calc R U . . .
C21 C 0.61032(12) 0.51367(17) 0.94177(12) 0.0295(4) Uani 1 1 d . . . . .
H21A H 0.6142 0.5851 0.9748 0.035 Uiso 1 1 calc R U . . .
H21B H 0.5662 0.5307 0.8932 0.035 Uiso 1 1 calc R U . . .
C22 C 0.58025(11) 0.40662(15) 0.97950(10) 0.0229(3) Uani 1 1 d . . . . .
C23 C 0.51667(13) 0.32851(16) 0.93793(10) 0.0254(4) Uani 1 1 d . . . . .
H23 H 0.4930 0.3421 0.8852 0.030 Uiso 1 1 calc R U . . .
C24 C 0.48729(12) 0.23109(16) 0.97228(10) 0.0245(4) Uani 1 1 d . . . . .
H24 H 0.4438 0.1778 0.9435 0.029 Uiso 1 1 calc R U . . .
C25 C 0.52194(11) 0.21217(15) 1.04893(10) 0.0212(3) Uani 1 1 d . . . . .
C26 C 0.58564(11) 0.28757(16) 1.09202(10) 0.0238(3) Uani 1 1 d . . . . .
H26 H 0.6091 0.2733 1.1447 0.029 Uiso 1 1 calc R U . . .
C27 C 0.61484(12) 0.38541(17) 1.05655(11) 0.0254(4) Uani 1 1 d . . . . .
H27 H 0.6588 0.4381 1.0854 0.030 Uiso 1 1 calc R U . . .
C31 C 1.05055(11) 0.52934(16) 0.91486(9) 0.0218(3) Uani 1 1 d . . . . .
H31A H 1.0538 0.5759 0.9618 0.026 Uiso 1 1 calc R U . . .
H31B H 1.0827 0.4527 0.9296 0.026 Uiso 1 1 calc R U . . .
C32 C 1.09775(10) 0.59856(15) 0.86492(9) 0.0185(3) Uani 1 1 d . . . . .
C33 C 1.14610(11) 0.70139(17) 0.89171(10) 0.0236(3) Uani 1 1 d . . . . .
H33 H 1.1503 0.7271 0.9423 0.028 Uiso 1 1 calc R U . . .
C34 C 1.18864(11) 0.76774(17) 0.84575(11) 0.0267(4) Uani 1 1 d . . . . .
H34 H 1.2210 0.8386 0.8644 0.032 Uiso 1 1 calc R U . . .
C35 C 1.18300(11) 0.72877(17) 0.77275(10) 0.0246(4) Uani 1 1 d . . . . .
C36 C 1.13737(12) 0.62531(18) 0.74501(10) 0.0258(4) Uani 1 1 d . . . . .
H36 H 1.1352 0.5986 0.6950 0.031 Uiso 1 1 calc R U . . .
C37 C 1.09470(11) 0.56084(16) 0.79107(10) 0.0227(3) Uani 1 1 d . . . . .
H37 H 1.0628 0.4898 0.7721 0.027 Uiso 1 1 calc R U . . .
C41 C 0.63559(10) 0.58634(14) 0.73892(8) 0.0142(3) Uani 1 1 d . . . . .
C42 C 0.57670(11) 0.68287(15) 0.73461(9) 0.0176(3) Uani 1 1 d . . . . .
H42 H 0.5983 0.7626 0.7337 0.021 Uiso 1 1 calc R U . . .
C43 C 0.48664(11) 0.66339(17) 0.73162(9) 0.0225(3) Uani 1 1 d . . . . .
H43 H 0.4474 0.7298 0.7295 0.027 Uiso 1 1 calc R U . . .
C44 C 0.45389(11) 0.54715(18) 0.73168(9) 0.0251(4) Uani 1 1 d . . . . .
H44 H 0.3924 0.5340 0.7299 0.030 Uiso 1 1 calc R U . . .
C45 C 0.51121(12) 0.45073(17) 0.73434(10) 0.0245(4) Uani 1 1 d . . . . .
H45 H 0.4888 0.3711 0.7334 0.029 Uiso 1 1 calc R U . . .
C46 C 0.60166(11) 0.47009(15) 0.73834(9) 0.0192(3) Uani 1 1 d . . . . .
H46 H 0.6407 0.4034 0.7407 0.023 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
Br1 C25 1.8960(16) . ?
Br2 C35 1.9040(17) . ?
S1 C21 1.8209(18) . ?
S1 C1 1.8438(15) . ?
S2 C31 1.8233(17) . ?
S2 C3 1.8448(15) . ?
C1 C9 1.498(2) . ?
C1 C2 1.529(2) . ?
C2 C10 1.346(2) . ?
C2 C3 1.536(2) . ?
C3 C4 1.509(2) . ?
C4 C5 1.391(2) . ?
C4 C9 1.392(2) . ?
C5 C6 1.392(2) . ?
C6 C7 1.392(3) . ?
C7 C8 1.387(3) . ?
C8 C9 1.387(2) . ?
C10 C41 1.509(2) . ?
C10 C11 1.538(2) . ?
C11 C14 1.531(2) . ?
C11 C13 1.533(2) . ?
C11 C12 1.537(2) . ?
C21 C22 1.505(2) . ?
C22 C23 1.386(3) . ?
C22 C27 1.391(3) . ?
C23 C24 1.383(2) . ?
C24 C25 1.381(3) . ?
C25 C26 1.379(3) . ?
C26 C27 1.396(2) . ?
C31 C32 1.508(2) . ?
C32 C33 1.387(2) . ?
C32 C37 1.397(2) . ?
C33 C34 1.394(3) . ?
C34 C35 1.379(3) . ?
C35 C36 1.379(3) . ?
C36 C37 1.386(2) . ?
C41 C46 1.396(2) . ?
C41 C42 1.396(2) . ?
C42 C43 1.391(2) . ?
C43 C44 1.390(3) . ?
C44 C45 1.383(3) . ?
C45 C46 1.393(2) . ?

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
C21 S1 C1 97.75(7) . . ?
C31 S2 C3 102.84(7) . . ?
C9 C1 C2 103.50(12) . . ?
C9 C1 S1 111.79(10) . . ?
C2 C1 S1 113.01(10) . . ?
C10 C2 C1 122.16(13) . . ?
C10 C2 C3 131.26(13) . . ?
C1 C2 C3 106.53(12) . . ?
C4 C3 C2 102.74(12) . . ?
C4 C3 S2 113.13(10) . . ?
C2 C3 S2 104.92(10) . . ?
C5 C4 C9 120.16(14) . . ?
C5 C4 C3 129.10(14) . . ?
C9 C4 C3 110.63(13) . . ?
C4 C5 C6 118.88(16) . . ?
C7 C6 C5 120.51(16) . . ?
C8 C7 C6 120.73(16) . . ?
C9 C8 C7 118.60(16) . . ?
C8 C9 C4 121.10(15) . . ?
C8 C9 C1 127.99(14) . . ?
C4 C9 C1 110.80(13) . . ?
C2 C10 C41 115.34(13) . . ?
C2 C10 C11 129.98(13) . . ?
C41 C10 C11 114.65(12) . . ?
C14 C11 C13 107.85(13) . . ?
C14 C11 C12 107.25(13) . . ?
C13 C11 C12 108.33(15) . . ?
C14 C11 C10 115.13(12) . . ?
C13 C11 C10 108.76(13) . . ?
C12 C11 C10 109.32(13) . . ?
C22 C21 S1 109.48(12) . . ?
C23 C22 C27 119.08(16) . . ?
C23 C22 C21 120.26(17) . . ?
C27 C22 C21 120.65(18) . . ?
C24 C23 C22 120.78(17) . . ?
C25 C24 C23 119.23(17) . . ?
C26 C25 C24 121.61(16) . . ?
C26 C25 Br1 119.14(13) . . ?
C24 C25 Br1 119.22(14) . . ?
C25 C26 C27 118.54(16) . . ?
C22 C27 C26 120.75(17) . . ?
C32 C31 S2 113.94(11) . . ?
C33 C32 C37 118.28(16) . . ?
C33 C32 C31 120.47(15) . . ?
C37 C32 C31 121.24(16) . . ?
C32 C33 C34 121.18(16) . . ?
C35 C34 C33 118.89(17) . . ?
C36 C35 C34 121.39(17) . . ?
C36 C35 Br2 119.15(14) . . ?
C34 C35 Br2 119.46(14) . . ?
C35 C36 C37 119.10(17) . . ?
C36 C37 C32 121.13(17) . . ?
C46 C41 C42 118.54(14) . . ?
C46 C41 C10 120.46(14) . . ?
C42 C41 C10 120.92(14) . . ?
C43 C42 C41 120.60(15) . . ?
C44 C43 C42 120.24(16) . . ?
C45 C44 C43 119.69(15) . . ?
C44 C45 C46 120.14(16) . . ?
C45 C46 C41 120.77(16) . . ?

_refine_diff_density_max         0.875
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mml121s_compound_6a
_database_code_depnum_ccdc_archive 'CCDC 1052427'
_audit_update_record             
;
2015-03-06 deposited with the CCDC.
2015-07-08 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 O2'
_chemical_formula_weight         244.32

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   'P 21/c'

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

_cell_length_a                   8.3105(7)
_cell_length_b                   9.1610(8)
_cell_length_c                   17.2363(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.798(2)
_cell_angle_gamma                90.00
_cell_volume                     1311.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6671
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.68

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8453
_exptl_absorpt_correction_T_max  0.9858
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15574
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         28.68
_reflns_number_total             3190
_reflns_number_gt                2940
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'

_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)+(0.0636P)²+0.4656P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    'Me rigid, others riding'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3190
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_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
O1 O 0.32885(9) 0.82877(9) 0.18753(5) 0.01743(19) Uani 1 1 d . . .
O2 O 0.04980(9) 0.60580(8) 0.19168(4) 0.01513(18) Uani 1 1 d . . .
C1 C 0.21449(13) 0.80705(13) 0.24697(7) 0.0184(2) Uani 1 1 d . . .
H1A H 0.1997 0.9000 0.2752 0.022 Uiso 1 1 calc R . .
H1B H 0.2575 0.7341 0.2846 0.022 Uiso 1 1 calc R . .
C2 C 0.05275(13) 0.75527(12) 0.21467(7) 0.0167(2) Uani 1 1 d . . .
H2A H -0.0289 0.7703 0.2545 0.020 Uiso 1 1 calc R . .
H2B H 0.0216 0.8163 0.1692 0.020 Uiso 1 1 calc R . .
C3 C 0.15322(12) 0.57319(11) 0.12892(6) 0.0126(2) Uani 1 1 d . . .
H3 H 0.1329 0.6393 0.0835 0.015 Uiso 1 1 calc R . .
C4 C 0.12125(12) 0.41504(11) 0.10849(6) 0.0133(2) Uani 1 1 d . . .
C5 C -0.01741(13) 0.35059(12) 0.07850(6) 0.0160(2) Uani 1 1 d . . .
H5 H -0.1088 0.4080 0.0642 0.019 Uiso 1 1 calc R . .
C6 C -0.02034(14) 0.19825(13) 0.06964(7) 0.0192(2) Uani 1 1 d . . .
H6 H -0.1139 0.1519 0.0482 0.023 Uiso 1 1 calc R . .
C7 C 0.11300(14) 0.11477(13) 0.09208(7) 0.0196(2) Uani 1 1 d . . .
H7 H 0.1089 0.0117 0.0864 0.024 Uiso 1 1 calc R . .
C8 C 0.25276(14) 0.18000(12) 0.12284(6) 0.0180(2) Uani 1 1 d . . .
H8 H 0.3432 0.1225 0.1385 0.022 Uiso 1 1 calc R . .
C9 C 0.25662(13) 0.33122(12) 0.13001(6) 0.0148(2) Uani 1 1 d . . .
C10 C 0.38359(12) 0.43171(12) 0.15823(6) 0.0158(2) Uani 1 1 d . . .
H10 H 0.4878 0.4025 0.1764 0.019 Uiso 1 1 calc R . .
C11 C 0.33157(12) 0.57045(12) 0.15465(6) 0.0136(2) Uani 1 1 d . . .
C12 C 0.42918(12) 0.70601(12) 0.17205(6) 0.0140(2) Uani 1 1 d . . .
H12 H 0.4989 0.6869 0.2193 0.017 Uiso 1 1 calc R . .
C13 C 0.53941(12) 0.75455(12) 0.10539(6) 0.0142(2) Uani 1 1 d . . .
C14 C 0.43788(14) 0.78883(13) 0.03185(6) 0.0192(2) Uani 1 1 d . . .
H14A H 0.5080 0.8252 -0.0086 0.029 Uiso 1 1 calc R . .
H14B H 0.3576 0.8633 0.0435 0.029 Uiso 1 1 calc R . .
H14C H 0.3832 0.6999 0.0135 0.029 Uiso 1 1 calc R . .
C15 C 0.63380(13) 0.89073(13) 0.13156(7) 0.0194(2) Uani 1 1 d . . .
H15A H 0.7062 0.9203 0.0906 0.029 Uiso 1 1 calc R . .
H15B H 0.6970 0.8686 0.1791 0.029 Uiso 1 1 calc R . .
H15C H 0.5584 0.9703 0.1417 0.029 Uiso 1 1 calc R . .
C16 C 0.66129(13) 0.63423(13) 0.08804(7) 0.0188(2) Uani 1 1 d . . .
H16A H 0.6041 0.5479 0.0680 0.028 Uiso 1 1 calc R . .
H16B H 0.7218 0.6086 0.1358 0.028 Uiso 1 1 calc R . .
H16C H 0.7359 0.6693 0.0492 0.028 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
O1 C12 1.4301(13) . ?
O1 C1 1.4331(13) . ?
O2 C2 1.4254(13) . ?
O2 C3 1.4340(12) . ?
C1 C2 1.5148(15) . ?
C3 C4 1.5125(14) . ?
C3 C11 1.5340(14) . ?
C4 C5 1.3807(15) . ?
C4 C9 1.4023(14) . ?
C5 C6 1.4040(16) . ?
C6 C7 1.3912(16) . ?
C7 C8 1.3960(16) . ?
C8 C9 1.3911(15) . ?
C9 C10 1.4715(15) . ?
C10 C11 1.3433(15) . ?
C11 C12 1.5083(15) . ?
C12 C13 1.5565(14) . ?
C13 C16 1.5327(15) . ?
C13 C14 1.5331(15) . ?
C13 C15 1.5340(15) . ?

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
C12 O1 C1 115.33(8) . . ?
C2 O2 C3 113.85(8) . . ?
O1 C1 C2 112.42(9) . . ?
O2 C2 C1 114.23(9) . . ?
O2 C3 C4 105.68(8) . . ?
O2 C3 C11 112.45(8) . . ?
C4 C3 C11 102.28(8) . . ?
C5 C4 C9 121.20(10) . . ?
C5 C4 C3 129.43(9) . . ?
C9 C4 C3 109.23(9) . . ?
C4 C5 C6 118.50(10) . . ?
C7 C6 C5 120.35(10) . . ?
C6 C7 C8 121.08(11) . . ?
C9 C8 C7 118.46(10) . . ?
C8 C9 C4 120.38(10) . . ?
C8 C9 C10 131.80(10) . . ?
C4 C9 C10 107.81(9) . . ?
C11 C10 C9 110.51(9) . . ?
C10 C11 C12 126.84(9) . . ?
C10 C11 C3 109.60(9) . . ?
C12 C11 C3 123.56(9) . . ?
O1 C12 C11 111.81(8) . . ?
O1 C12 C13 105.85(8) . . ?
C11 C12 C13 114.44(9) . . ?
C16 C13 C14 109.62(9) . . ?
C16 C13 C15 107.90(9) . . ?
C14 C13 C15 109.85(9) . . ?
C16 C13 C12 110.27(9) . . ?
C14 C13 C12 110.33(9) . . ?
C15 C13 C12 108.83(9) . . ?

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
C12 O1 C1 C2 -92.59(11) . . . . ?
C3 O2 C2 C1 -63.71(12) . . . . ?
O1 C1 C2 O2 75.16(12) . . . . ?
C2 O2 C3 C4 -174.79(8) . . . . ?
C2 O2 C3 C11 74.41(11) . . . . ?
O2 C3 C4 C5 65.10(13) . . . . ?
C11 C3 C4 C5 -177.05(10) . . . . ?
O2 C3 C4 C9 -110.63(9) . . . . ?
C11 C3 C4 C9 7.21(10) . . . . ?
C9 C4 C5 C6 -0.18(15) . . . . ?
C3 C4 C5 C6 -175.48(10) . . . . ?
C4 C5 C6 C7 1.18(16) . . . . ?
C5 C6 C7 C8 -0.80(17) . . . . ?
C6 C7 C8 C9 -0.58(16) . . . . ?
C7 C8 C9 C4 1.57(16) . . . . ?
C7 C8 C9 C10 -178.77(10) . . . . ?
C5 C4 C9 C8 -1.21(16) . . . . ?
C3 C4 C9 C8 174.95(9) . . . . ?
C5 C4 C9 C10 179.05(9) . . . . ?
C3 C4 C9 C10 -4.79(11) . . . . ?
C8 C9 C10 C11 -179.76(11) . . . . ?
C4 C9 C10 C11 -0.06(12) . . . . ?
C9 C10 C11 C12 -174.71(9) . . . . ?
C9 C10 C11 C3 4.84(12) . . . . ?
O2 C3 C11 C10 105.59(10) . . . . ?
C4 C3 C11 C10 -7.31(11) . . . . ?
O2 C3 C11 C12 -74.84(12) . . . . ?
C4 C3 C11 C12 172.25(9) . . . . ?
C1 O1 C12 C11 53.79(11) . . . . ?
C1 O1 C12 C13 179.02(8) . . . . ?
C10 C11 C12 O1 -160.74(10) . . . . ?
C3 C11 C12 O1 19.78(13) . . . . ?
C10 C11 C12 C13 78.93(13) . . . . ?
C3 C11 C12 C13 -100.55(11) . . . . ?
O1 C12 C13 C16 175.85(8) . . . . ?
C11 C12 C13 C16 -60.57(12) . . . . ?
O1 C12 C13 C14 -62.91(11) . . . . ?
C11 C12 C13 C14 60.67(12) . . . . ?
O1 C12 C13 C15 57.68(10) . . . . ?
C11 C12 C13 C15 -178.73(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.941
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_mml129s_compound_10
_database_code_depnum_ccdc_archive 'CCDC 1052428'
_audit_update_record             
;
2015-03-06 deposited with the CCDC.
2015-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 O2'
_chemical_formula_weight         246.34

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   'P 21/c'

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

_cell_length_a                   9.0160(9)
_cell_length_b                   12.6459(13)
_cell_length_c                   12.1727(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.210(2)
_cell_angle_gamma                90.00
_cell_volume                     1379.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5334
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 8.26
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16611
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         28.75
_reflns_number_total             3365
_reflns_number_gt                2939
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0752P)²+0.3206P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    'Me rigid, others riding'
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3365
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_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
O1 O 0.02381(9) 0.24082(6) 0.52768(7) 0.0209(2) Uani 1 1 d . . .
O2 O 0.40479(8) 0.11557(6) 0.39461(6) 0.01927(19) Uani 1 1 d . . .
C1 C 0.27446(11) 0.15348(8) 0.55404(8) 0.0160(2) Uani 1 1 d . . .
C2 C 0.14557(12) 0.20779(8) 0.60395(9) 0.0177(2) Uani 1 1 d . . .
H2 H 0.1871 0.2724 0.6435 0.021 Uiso 1 1 calc R . .
C3 C 0.10940(12) 0.12905(9) 0.69106(9) 0.0192(2) Uani 1 1 d . . .
C4 C 0.00083(14) 0.13246(10) 0.76308(10) 0.0248(3) Uani 1 1 d . . .
H4 H -0.0680 0.1895 0.7610 0.030 Uiso 1 1 calc R . .
C5 C -0.00517(14) 0.05004(11) 0.83899(10) 0.0288(3) Uani 1 1 d . . .
H5 H -0.0793 0.0510 0.8888 0.035 Uiso 1 1 calc R . .
C6 C 0.09542(15) -0.03304(10) 0.84270(10) 0.0280(3) Uani 1 1 d . . .
H6 H 0.0894 -0.0883 0.8949 0.034 Uiso 1 1 calc R . .
C7 C 0.20574(14) -0.03641(9) 0.77032(9) 0.0238(3) Uani 1 1 d . . .
H7 H 0.2753 -0.0930 0.7731 0.029 Uiso 1 1 calc R . .
C8 C 0.21099(12) 0.04518(9) 0.69415(9) 0.0185(2) Uani 1 1 d . . .
C9 C 0.31035(12) 0.06269(8) 0.60749(9) 0.0178(2) Uani 1 1 d . . .
H9 H 0.3884 0.0165 0.5917 0.021 Uiso 1 1 calc R . .
C10 C 0.34647(11) 0.19846(8) 0.45786(9) 0.0164(2) Uani 1 1 d . . .
H10 H 0.2687 0.2375 0.4089 0.020 Uiso 1 1 calc R . .
C11 C 0.47857(12) 0.27498(8) 0.49081(9) 0.0178(2) Uani 1 1 d . . .
C12 C 0.42527(13) 0.36837(9) 0.55659(11) 0.0241(3) Uani 1 1 d . . .
H12A H 0.4033 0.3437 0.6294 0.029 Uiso 1 1 calc R . .
H12B H 0.3349 0.3987 0.5167 0.029 Uiso 1 1 calc R . .
H12C H 0.5036 0.4224 0.5657 0.029 Uiso 1 1 calc R . .
C13 C 0.60513(12) 0.21744(9) 0.56057(9) 0.0202(2) Uani 1 1 d . . .
H13A H 0.6335 0.1543 0.5211 0.024 Uiso 1 1 calc R . .
H13B H 0.5715 0.1965 0.6313 0.024 Uiso 1 1 calc R . .
H13C H 0.6914 0.2646 0.5740 0.024 Uiso 1 1 calc R . .
C14 C 0.53512(14) 0.31679(10) 0.38457(10) 0.0251(3) Uani 1 1 d . . .
H14A H 0.6162 0.3674 0.4036 0.030 Uiso 1 1 calc R . .
H14B H 0.4533 0.3520 0.3392 0.030 Uiso 1 1 calc R . .
H14C H 0.5721 0.2577 0.3431 0.030 Uiso 1 1 calc R . .
C15 C 0.29352(13) 0.05491(9) 0.33169(9) 0.0208(2) Uani 1 1 d . . .
H15A H 0.2366 0.0146 0.3816 0.025 Uiso 1 1 calc R . .
H15B H 0.3410 0.0060 0.2837 0.025 Uiso 1 1 calc R . .
H15C H 0.2261 0.1022 0.2863 0.025 Uiso 1 1 calc R . .
C16 C -0.04333(13) 0.15686(9) 0.46220(10) 0.0222(2) Uani 1 1 d . . .
H16A H 0.0264 0.1314 0.4117 0.027 Uiso 1 1 calc R . .
H16B H -0.1346 0.1824 0.4194 0.027 Uiso 1 1 calc R . .
H16C H -0.0681 0.0989 0.5104 0.027 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
O1 C2 1.4217(13) . ?
O1 C16 1.4229(14) . ?
O2 C15 1.4197(13) . ?
O2 C10 1.4338(12) . ?
C1 C9 1.3418(15) . ?
C1 C10 1.5100(14) . ?
C1 C2 1.5310(14) . ?
C2 C3 1.5156(15) . ?
C3 C4 1.3836(16) . ?
C3 C8 1.3992(16) . ?
C4 C5 1.3978(17) . ?
C5 C6 1.386(2) . ?
C6 C7 1.3989(18) . ?
C7 C8 1.3914(15) . ?
C8 C9 1.4727(15) . ?
C10 C11 1.5531(14) . ?
C11 C13 1.5307(15) . ?
C11 C12 1.5330(15) . ?
C11 C14 1.5345(15) . ?

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
C2 O1 C16 113.47(8) . . ?
C15 O2 C10 113.95(8) . . ?
C9 C1 C10 126.65(10) . . ?
C9 C1 C2 110.18(9) . . ?
C10 C1 C2 123.17(9) . . ?
O1 C2 C3 116.14(9) . . ?
O1 C2 C1 116.00(9) . . ?
C3 C2 C1 102.29(8) . . ?
C4 C3 C8 120.83(11) . . ?
C4 C3 C2 130.04(11) . . ?
C8 C3 C2 109.09(9) . . ?
C3 C4 C5 118.44(12) . . ?
C6 C5 C4 121.00(11) . . ?
C5 C6 C7 120.66(11) . . ?
C8 C7 C6 118.35(12) . . ?
C7 C8 C3 120.71(11) . . ?
C7 C8 C9 131.00(11) . . ?
C3 C8 C9 108.30(9) . . ?
C1 C9 C8 110.03(10) . . ?
O2 C10 C1 110.75(8) . . ?
O2 C10 C11 106.18(8) . . ?
C1 C10 C11 114.61(9) . . ?
C13 C11 C12 109.47(9) . . ?
C13 C11 C14 109.61(9) . . ?
C12 C11 C14 109.04(9) . . ?
C13 C11 C10 110.60(8) . . ?
C12 C11 C10 109.87(9) . . ?
C14 C11 C10 108.21(9) . . ?

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
C16 O1 C2 C3 -62.17(11) . . . . ?
C16 O1 C2 C1 58.04(12) . . . . ?
C9 C1 C2 O1 -130.28(10) . . . . ?
C10 C1 C2 O1 49.31(13) . . . . ?
C9 C1 C2 C3 -2.84(11) . . . . ?
C10 C1 C2 C3 176.75(9) . . . . ?
O1 C2 C3 C4 -51.48(15) . . . . ?
C1 C2 C3 C4 -178.83(11) . . . . ?
O1 C2 C3 C8 130.70(9) . . . . ?
C1 C2 C3 C8 3.35(11) . . . . ?
C8 C3 C4 C5 -0.08(17) . . . . ?
C2 C3 C4 C5 -177.68(11) . . . . ?
C3 C4 C5 C6 0.29(18) . . . . ?
C4 C5 C6 C7 0.01(18) . . . . ?
C5 C6 C7 C8 -0.52(17) . . . . ?
C6 C7 C8 C3 0.73(16) . . . . ?
C6 C7 C8 C9 -178.80(11) . . . . ?
C4 C3 C8 C7 -0.43(16) . . . . ?
C2 C3 C8 C7 177.62(9) . . . . ?
C4 C3 C8 C9 179.19(10) . . . . ?
C2 C3 C8 C9 -2.76(12) . . . . ?
C10 C1 C9 C8 -178.24(9) . . . . ?
C2 C1 C9 C8 1.34(12) . . . . ?
C7 C8 C9 C1 -179.53(11) . . . . ?
C3 C8 C9 C1 0.90(12) . . . . ?
C15 O2 C10 C1 71.79(11) . . . . ?
C15 O2 C10 C11 -163.21(8) . . . . ?
C9 C1 C10 O2 28.41(14) . . . . ?
C2 C1 C10 O2 -151.12(9) . . . . ?
C9 C1 C10 C11 -91.68(13) . . . . ?
C2 C1 C10 C11 88.80(12) . . . . ?
O2 C10 C11 C13 -60.52(11) . . . . ?
C1 C10 C11 C13 62.07(11) . . . . ?
O2 C10 C11 C12 178.51(8) . . . . ?
C1 C10 C11 C12 -58.90(12) . . . . ?
O2 C10 C11 C14 59.56(11) . . . . ?
C1 C10 C11 C14 -177.85(9) . . . . ?

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
C9 H9 O2 0.95 2.50 3.4194(13) 164.3 3_656

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.049

#===END
