# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mo_dm15200_0m
_audit_block_doi                 10.5517/ccdc.csd.cc1lc212
_database_code_depnum_ccdc_archive 'CCDC 1470393'
_audit_update_record             
;
2016-03-24 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 O3'
_chemical_formula_weight         270.31

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/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                   11.954(2)
_cell_length_b                   9.2780(18)
_cell_length_c                   12.604(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.422(3)
_cell_angle_gamma                90.00
_cell_volume                     1395.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1324
_cell_measurement_theta_min      2.727
_cell_measurement_theta_max      22.059

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9701
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13661
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0719
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         30.56
_reflns_number_total             4258
_reflns_number_gt                2117
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.2000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4258
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2297
_refine_ls_R_factor_gt           0.1489
_refine_ls_wR_factor_ref         0.4561
_refine_ls_wR_factor_gt          0.4068
_refine_ls_goodness_of_fit_ref   1.460
_refine_ls_restrained_S_all      1.460
_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 0.0080(3) 0.8965(4) 0.2508(3) 0.0417(9) Uani 1 1 d . . .
C14 C 0.1181(3) 1.0283(5) 0.1355(4) 0.0311(10) Uani 1 1 d . . .
H14 H 0.0898 1.1168 0.1557 0.037 Uiso 1 1 calc R . .
C15 C 0.1955(5) 1.0227(6) 0.0665(5) 0.0456(13) Uani 1 1 d . . .
H15 H 0.2223 1.1100 0.0421 0.055 Uiso 1 1 calc R . .
C16 C 0.2450(3) 0.8867(5) 0.0231(3) 0.0261(9) Uani 1 1 d . . .
O3 O 0.3610(3) 0.9024(5) 0.0058(3) 0.0475(11) Uani 1 1 d . . .
C10 C 0.4276(4) 0.9290(7) 0.1035(5) 0.0492(14) Uani 1 1 d . . .
H10A H 0.4012 1.0151 0.1378 0.059 Uiso 1 1 calc R . .
H10B H 0.5055 0.9435 0.0884 0.059 Uiso 1 1 calc R . .
C9 C 0.4176(4) 0.8022(6) 0.1749(4) 0.0397(12) Uani 1 1 d . . .
H9 H 0.4415 0.7152 0.1384 0.048 Uiso 1 1 calc R . .
C8 C 0.4839(4) 0.8173(6) 0.2776(4) 0.0416(12) Uani 1 1 d . . .
H8 H 0.4506 0.7916 0.3397 0.050 Uiso 1 1 calc R . .
C7 C 0.5905(4) 0.8666(7) 0.2854(4) 0.0456(14) Uani 1 1 d . . .
H7 H 0.6197 0.8966 0.2223 0.055 Uiso 1 1 calc R . .
C4 C 0.6658(3) 0.8786(5) 0.3811(4) 0.0308(10) Uani 1 1 d . . .
C5 C 0.7811(3) 0.8883(4) 0.3705(4) 0.0269(9) Uani 1 1 d . . .
H5 H 0.8084 0.8901 0.3030 0.032 Uiso 1 1 calc R . .
C6 C 0.8560(4) 0.8953(5) 0.4593(4) 0.0316(10) Uani 1 1 d . . .
H6 H 0.9326 0.8994 0.4508 0.038 Uiso 1 1 calc R . .
C1 C 0.8165(4) 0.8960(5) 0.5598(4) 0.0386(11) Uani 1 1 d . . .
H1 H 0.8665 0.9020 0.6191 0.046 Uiso 1 1 calc R . .
C13 C 0.0749(3) 0.8913(5) 0.1823(4) 0.0293(9) Uani 1 1 d . . .
C12 C 0.1143(3) 0.7531(5) 0.1372(3) 0.0258(9) Uani 1 1 d . . .
H12A H 0.1119 0.6781 0.1906 0.031 Uiso 1 1 calc R . .
H12B H 0.0641 0.7255 0.0773 0.031 Uiso 1 1 calc R . .
C11 C 0.2305(4) 0.7646(5) 0.1015(4) 0.0389(12) Uani 1 1 d . . .
H11 H 0.2513 0.6733 0.0689 0.047 Uiso 1 1 calc R . .
O2 O 0.3013(3) 0.7879(4) 0.1982(3) 0.0367(9) Uani 1 1 d . . .
C17 C 0.1918(4) 0.8601(8) -0.0853(4) 0.0517(15) Uani 1 1 d . . .
H17A H 0.1893 0.9485 -0.1250 0.078 Uiso 1 1 calc R . .
H17B H 0.1170 0.8246 -0.0794 0.078 Uiso 1 1 calc R . .
H17C H 0.2348 0.7900 -0.1214 0.078 Uiso 1 1 calc R . .
C2 C 0.7015(4) 0.8879(6) 0.5725(4) 0.0393(12) Uani 1 1 d . . .
H2 H 0.6748 0.8865 0.6403 0.047 Uiso 1 1 calc R . .
C3 C 0.6270(4) 0.8817(6) 0.4837(4) 0.0378(12) Uani 1 1 d . . .
H3 H 0.5503 0.8796 0.4926 0.045 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 C13 1.213(5) . ?
C14 C15 1.309(7) . ?
C14 C13 1.505(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.510(7) . ?
C15 H15 0.9300 . ?
C16 O3 1.424(5) . ?
C16 C17 1.493(7) . ?
C16 C11 1.520(6) . ?
O3 C10 1.448(6) . ?
C10 C9 1.490(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 O2 1.444(5) . ?
C9 C8 1.484(7) . ?
C9 H9 0.9800 . ?
C8 C7 1.352(7) . ?
C8 H8 0.9300 . ?
C7 C4 1.465(7) . ?
C7 H7 0.9300 . ?
C4 C5 1.395(6) . ?
C4 C3 1.400(7) . ?
C5 C6 1.392(6) . ?
C5 H5 0.9300 . ?
C6 C1 1.378(7) . ?
C6 H6 0.9300 . ?
C1 C2 1.395(7) . ?
C1 H1 0.9300 . ?
C13 C12 1.490(6) . ?
C12 C11 1.488(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 O2 1.459(6) . ?
C11 H11 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C2 C3 1.390(7) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?

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 C14 C13 120.0(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 125.6(4) . . ?
C14 C15 H15 117.2 . . ?
C16 C15 H15 117.2 . . ?
O3 C16 C17 104.0(4) . . ?
O3 C16 C15 112.1(4) . . ?
C17 C16 C15 108.4(4) . . ?
O3 C16 C11 109.0(3) . . ?
C17 C16 C11 114.4(4) . . ?
C15 C16 C11 108.9(4) . . ?
C16 O3 C10 112.2(3) . . ?
O3 C10 C9 108.6(4) . . ?
O3 C10 H10A 110.0 . . ?
C9 C10 H10A 110.0 . . ?
O3 C10 H10B 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
O2 C9 C8 107.6(4) . . ?
O2 C9 C10 108.0(4) . . ?
C8 C9 C10 113.2(4) . . ?
O2 C9 H9 109.3 . . ?
C8 C9 H9 109.3 . . ?
C10 C9 H9 109.3 . . ?
C7 C8 C9 123.2(5) . . ?
C7 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
C8 C7 C4 128.0(5) . . ?
C8 C7 H7 116.0 . . ?
C4 C7 H7 116.0 . . ?
C5 C4 C3 118.1(4) . . ?
C5 C4 C7 119.2(4) . . ?
C3 C4 C7 122.7(4) . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 120.1(4) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C1 C2 119.9(4) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
O1 C13 C12 122.9(4) . . ?
O1 C13 C14 120.1(4) . . ?
C12 C13 C14 117.0(4) . . ?
C11 C12 C13 112.1(4) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
O2 C11 C12 105.3(4) . . ?
O2 C11 C16 110.5(4) . . ?
C12 C11 C16 113.3(4) . . ?
O2 C11 H11 109.2 . . ?
C12 C11 H11 109.2 . . ?
C16 C11 H11 109.2 . . ?
C9 O2 C11 111.2(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?

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
C13 C14 C15 C16 2.9(8) . . . . ?
C14 C15 C16 O3 -144.4(5) . . . . ?
C14 C15 C16 C17 101.4(6) . . . . ?
C14 C15 C16 C11 -23.6(7) . . . . ?
C17 C16 O3 C10 -179.8(4) . . . . ?
C15 C16 O3 C10 63.3(5) . . . . ?
C11 C16 O3 C10 -57.4(5) . . . . ?
C16 O3 C10 C9 62.3(5) . . . . ?
O3 C10 C9 O2 -61.6(5) . . . . ?
O3 C10 C9 C8 179.4(4) . . . . ?
O2 C9 C8 C7 -163.7(5) . . . . ?
C10 C9 C8 C7 -44.5(7) . . . . ?
C9 C8 C7 C4 -176.4(5) . . . . ?
C8 C7 C4 C5 160.0(6) . . . . ?
C8 C7 C4 C3 -20.4(9) . . . . ?
C3 C4 C5 C6 2.4(7) . . . . ?
C7 C4 C5 C6 -177.9(4) . . . . ?
C4 C5 C6 C1 -1.5(7) . . . . ?
C5 C6 C1 C2 0.8(7) . . . . ?
C15 C14 C13 O1 175.7(5) . . . . ?
C15 C14 C13 C12 -6.8(7) . . . . ?
O1 C13 C12 C11 -150.2(4) . . . . ?
C14 C13 C12 C11 32.4(5) . . . . ?
C13 C12 C11 O2 66.0(4) . . . . ?
C13 C12 C11 C16 -54.8(5) . . . . ?
O3 C16 C11 O2 53.8(5) . . . . ?
C17 C16 C11 O2 169.8(4) . . . . ?
C15 C16 C11 O2 -68.8(5) . . . . ?
O3 C16 C11 C12 171.6(4) . . . . ?
C17 C16 C11 C12 -72.4(5) . . . . ?
C15 C16 C11 C12 49.0(5) . . . . ?
C8 C9 O2 C11 -176.9(4) . . . . ?
C10 C9 O2 C11 60.6(5) . . . . ?
C12 C11 O2 C9 -179.6(4) . . . . ?
C16 C11 O2 C9 -57.0(5) . . . . ?
C6 C1 C2 C3 -1.2(8) . . . . ?
C1 C2 C3 C4 2.2(8) . . . . ?
C5 C4 C3 C2 -2.8(7) . . . . ?
C7 C4 C3 C2 177.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        30.56
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         2.759
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.147
