# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1f
_database_code_depnum_ccdc_archive 'CCDC 1869873'
_audit_update_record             
;
2018-09-26 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;


#-----------------------------------------------------
#------------------ COMPOUND 1    ---------------------
#----------------------------------------------------- 


_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H26 O4'
_chemical_formula_sum            'C18 H26 O4'
_chemical_formula_weight         306.39

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           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                   5.4153(2)
_cell_length_b                   16.4548(4)
_cell_length_c                   9.6656(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.990(3)
_cell_angle_gamma                90
_cell_volume                     831.97(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    1869
_cell_measurement_theta_min      5.3690
_cell_measurement_theta_max      69.0660

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.685
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71453
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.2640
_diffrn_reflns_number            3657
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.376
_diffrn_reflns_theta_max         69.516
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1532
_reflns_number_gt                1291
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0532P)²+0.2099P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1532
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_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 0.0470(3) 0.95973(9) 0.73702(14) 0.0262(3) Uani 1 1 d . . . . .
C2 C -0.1965(3) 1.00393(10) 0.67626(16) 0.0342(4) Uani 1 1 d . . . . .
H2A H -0.1876 1.0579 0.7200 0.051 Uiso 1 1 calc R U . . .
H2B H -0.3388 0.9734 0.6963 0.051 Uiso 1 1 calc R U . . .
H2C H -0.2237 1.0096 0.5725 0.051 Uiso 1 1 calc R U . . .
C3 C 0.3054(3) 0.90695(8) 0.95583(13) 0.0238(3) Uani 1 1 d . . . . .
C4 C 0.5006(3) 0.95639(9) 1.01021(14) 0.0250(3) Uani 1 1 d . . . . .
C5 C 0.2993(3) 0.81732(9) 0.97870(14) 0.0264(3) Uani 1 1 d . . . . .
C6 C 0.0900(3) 0.78869(10) 1.04870(18) 0.0361(4) Uani 1 1 d . . . . .
H6A H 0.1498 0.7930 1.1543 0.043 Uiso 1 1 calc R U . . .
H6B H -0.0660 0.8222 1.0153 0.043 Uiso 1 1 calc R U . . .
C7 C 0.0353(4) 0.70047(11) 1.0036(2) 0.0477(5) Uani 1 1 d . . . . .
H7A H -0.1492 0.6928 0.9580 0.057 Uiso 1 1 calc R U . . .
H7B H 0.0851 0.6642 1.0879 0.057 Uiso 1 1 calc R U . . .
C8 C 0.1924(3) 0.68130(9) 0.89743(17) 0.0370(4) Uani 1 1 d . . . . .
H8A H 0.0929 0.6477 0.8173 0.044 Uiso 1 1 calc R U . . .
H8B H 0.3514 0.6521 0.9451 0.044 Uiso 1 1 calc R U . . .
C9 C 0.2526(3) 0.76453(9) 0.84387(16) 0.0333(4) Uani 1 1 d . . . . .
H9A H 0.1069 0.7853 0.7677 0.040 Uiso 1 1 calc R U . . .
H9B H 0.4065 0.7622 0.8067 0.040 Uiso 1 1 calc R U . . .
H4 H 0.656(3) 0.9330(10) 1.0698(18) 0.027(4) Uiso 1 1 d . . . . .
H5 H 0.469(3) 0.8026(11) 1.0432(19) 0.032(4) Uiso 1 1 d . . . . .
O1 O 0.07078(18) 0.94009(6) 0.87707(10) 0.0255(3) Uani 1 1 d . . . . .
O2 O 0.2071(2) 0.94328(7) 0.67598(11) 0.0368(3) Uani 1 1 d . . . . .


_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 O2 1.1990(18) . ?
C1 O1 1.3651(17) . ?
C1 C2 1.488(2) . ?
C3 C4 1.330(2) . ?
C3 O1 1.4108(16) . ?
C3 C5 1.493(2) . ?
C4 C4 1.449(3) 3_677 ?
C5 C9 1.532(2) . ?
C5 C6 1.536(2) . ?
C6 C7 1.523(2) . ?
C7 C8 1.526(2) . ?
C8 C9 1.529(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
O2 C1 O1 122.68(13) . . ?
O2 C1 C2 126.61(13) . . ?
O1 C1 C2 110.71(12) . . ?
C4 C3 O1 119.31(12) . . ?
C4 C3 C5 126.27(13) . . ?
O1 C3 C5 114.24(11) . . ?
C3 C4 C4 125.27(16) . 3_677 ?
C3 C5 C9 116.07(11) . . ?
C3 C5 C6 114.53(12) . . ?
C9 C5 C6 102.85(12) . . ?
C7 C6 C5 106.12(13) . . ?
C6 C7 C8 106.76(13) . . ?
C7 C8 C9 104.33(13) . . ?
C8 C9 C5 102.87(12) . . ?
C1 O1 C3 117.86(10) . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-3

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane / Ethyl Acetate'
