# Electronic Supplementary Material (ESI) for ChemComm.
# 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_lqq
_audit_block_doi                 10.5517/cc1k8w0q
_database_code_depnum_ccdc_archive 'CCDC 1438493'
_audit_update_record             
;
2016-04-10 deposited with the CCDC.
2016-04-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
'(2S,3S)-3,7-dimethyl-2-(5-methyl-2-oxohexyl)-3- ((E)-6-methyl-3-oxohept-1-en-1-yl)-3,4-dihydronaphthalen-1(2H)-one'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H38 O3'
_chemical_formula_sum            'C27 H38 O3'
_chemical_formula_weight         410.57

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                   5.8458(3)
_cell_length_b                   12.3784(6)
_cell_length_c                   16.7657(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.058(6)
_cell_angle_gamma                90
_cell_volume                     1201.23(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2334
_cell_measurement_theta_min      4.4450
_cell_measurement_theta_max      73.9760

_exptl_crystal_description       monoclinic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.560
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68829
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Sphere (Rigaku CrystalClear)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3503
_diffrn_reflns_number            4524
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.456
_diffrn_reflns_theta_max         75.388
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3234
_reflns_number_gt                3024
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_max     0.955
_reflns_Friedel_fraction_full    0.999

_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       'CrystalClear (Rigaku Corp., 2002)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2002)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0761P)²+0.1734P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.1(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3234
_refine_ls_number_parameters     278
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_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
O28 O 1.3388(3) 1.26795(16) 1.36845(12) 0.0352(5) Uani 1 1 d . . . . .
O19 O 2.3599(3) 1.51956(18) 1.62578(12) 0.0369(5) Uani 1 1 d . . . . .
O27 O 1.9375(3) 1.24170(17) 1.57771(12) 0.0372(5) Uani 1 1 d . . . . .
C9 C 1.5072(4) 1.3245(2) 1.36398(15) 0.0252(5) Uani 1 1 d . . . . .
C13 C 2.1671(4) 1.5539(2) 1.63124(15) 0.0260(5) Uani 1 1 d . . . . .
C8 C 1.5461(4) 1.3742(2) 1.28595(15) 0.0244(5) Uani 1 1 d . . . . .
C11 C 1.9762(4) 1.4790(2) 1.50324(16) 0.0248(5) Uani 1 1 d . . . . .
H11 H 2.1063 1.4354 1.5050 0.030 Uiso 1 1 calc R U . . .
C3 C 1.7367(4) 1.4398(2) 1.28065(16) 0.0271(5) Uani 1 1 d . . . . .
C10 C 1.6860(4) 1.3476(2) 1.43758(15) 0.0234(5) Uani 1 1 d . . . . .
H10 H 1.8132 1.2964 1.4360 0.028 Uiso 1 1 calc R U . . .
C20 C 1.5871(4) 1.3265(2) 1.51556(15) 0.0266(5) Uani 1 1 d . . . . .
H20A H 1.5198 1.3932 1.5318 0.032 Uiso 1 1 calc R U . . .
H20B H 1.4630 1.2743 1.5045 0.032 Uiso 1 1 calc R U . . .
C7 C 1.3797(5) 1.3564(2) 1.21735(15) 0.0283(6) Uani 1 1 d . . . . .
H7 H 1.2512 1.3138 1.2219 0.034 Uiso 1 1 calc R U . . .
C21 C 1.7560(4) 1.2854(2) 1.58573(16) 0.0282(5) Uani 1 1 d . . . . .
C12 C 1.9732(4) 1.5493(2) 1.56334(15) 0.0267(5) Uani 1 1 d . . . . .
H12 H 1.8485 1.5960 1.5629 0.032 Uiso 1 1 calc R U . . .
C4 C 1.7655(5) 1.4828(2) 1.20594(16) 0.0323(6) Uani 1 1 d . . . . .
H4 H 1.8947 1.5249 1.2011 0.039 Uiso 1 1 calc R U . . .
C1 C 1.7886(4) 1.4635(2) 1.43248(14) 0.0230(5) Uani 1 1 d . . . . .
C2 C 1.9054(4) 1.4658(2) 1.35492(15) 0.0281(5) Uani 1 1 d . . . . .
H2A H 1.9706 1.5370 1.3490 0.034 Uiso 1 1 calc R U . . .
H2B H 2.0308 1.4139 1.3600 0.034 Uiso 1 1 calc R U . . .
C29 C 1.6020(4) 1.5511(2) 1.42923(15) 0.0265(5) Uani 1 1 d . . . . .
H29A H 1.6712 1.6208 1.4249 0.040 Uiso 1 1 calc R U . . .
H29B H 1.5311 1.5482 1.4775 0.040 Uiso 1 1 calc R U . . .
H29C H 1.4870 1.5390 1.3833 0.040 Uiso 1 1 calc R U . . .
C14 C 2.1077(4) 1.6039(2) 1.70831(16) 0.0293(6) Uani 1 1 d . . . . .
H14A H 1.9682 1.5702 1.7217 0.035 Uiso 1 1 calc R U . . .
H14B H 2.0750 1.6800 1.6989 0.035 Uiso 1 1 calc R U . . .
C15 C 2.2972(4) 1.5928(2) 1.77995(15) 0.0274(5) Uani 1 1 d . . . . .
H15A H 2.4343 1.6298 1.7677 0.033 Uiso 1 1 calc R U . . .
H15B H 2.3355 1.5169 1.7877 0.033 Uiso 1 1 calc R U . . .
C6 C 1.4056(5) 1.4016(2) 1.14366(16) 0.0314(6) Uani 1 1 d . . . . .
C16 C 2.2320(4) 1.6381(2) 1.85834(15) 0.0296(6) Uani 1 1 d . . . . .
H16 H 2.1917 1.7145 1.8499 0.036 Uiso 1 1 calc R U . . .
C24 C 1.7645(5) 1.2842(3) 1.81926(16) 0.0346(6) Uani 1 1 d . . . . .
H24 H 1.8115 1.3602 1.8227 0.042 Uiso 1 1 calc R U . . .
C22 C 1.6763(5) 1.3029(2) 1.66674(16) 0.0304(6) Uani 1 1 d . . . . .
H22A H 1.5145 1.2832 1.6622 0.036 Uiso 1 1 calc R U . . .
H22B H 1.6876 1.3794 1.6792 0.036 Uiso 1 1 calc R U . . .
C5 C 1.6031(5) 1.4636(2) 1.13850(16) 0.0339(6) Uani 1 1 d . . . . .
H5 H 1.6263 1.4924 1.0890 0.041 Uiso 1 1 calc R U . . .
C18 C 2.4384(5) 1.6305(3) 1.92546(16) 0.0365(7) Uani 1 1 d . . . . .
H18A H 2.5651 1.6717 1.9106 0.055 Uiso 1 1 calc R U . . .
H18B H 2.4839 1.5564 1.9333 0.055 Uiso 1 1 calc R U . . .
H18C H 2.3954 1.6589 1.9746 0.055 Uiso 1 1 calc R U . . .
C23 C 1.8079(5) 1.2407(3) 1.73731(16) 0.0340(6) Uani 1 1 d . . . . .
H23A H 1.9720 1.2444 1.7339 0.041 Uiso 1 1 calc R U . . .
H23B H 1.7623 1.1653 1.7331 0.041 Uiso 1 1 calc R U . . .
C30 C 1.2236(5) 1.3863(3) 1.07090(17) 0.0379(7) Uani 1 1 d . . . . .
H30A H 1.1504 1.4543 1.0563 0.057 Uiso 1 1 calc R U . . .
H30B H 1.1100 1.3355 1.0836 0.057 Uiso 1 1 calc R U . . .
H30C H 1.2950 1.3594 1.0267 0.057 Uiso 1 1 calc R U . . .
C17 C 2.0262(5) 1.5801(3) 1.88452(18) 0.0434(8) Uani 1 1 d . . . . .
H17A H 2.0613 1.5047 1.8918 0.065 Uiso 1 1 calc R U . . .
H17B H 1.8943 1.5886 1.8439 0.065 Uiso 1 1 calc R U . . .
H17C H 1.9928 1.6103 1.9343 0.065 Uiso 1 1 calc R U . . .
C26 C 1.9109(5) 1.2228(4) 1.88750(18) 0.0496(9) Uani 1 1 d . . . . .
H26A H 2.0707 1.2265 1.8802 0.074 Uiso 1 1 calc R U . . .
H26B H 1.8626 1.1487 1.8869 0.074 Uiso 1 1 calc R U . . .
H26C H 1.8912 1.2549 1.9382 0.074 Uiso 1 1 calc R U . . .
C25 C 1.5120(5) 1.2782(3) 1.83027(19) 0.0414(7) Uani 1 1 d . . . . .
H25A H 1.4610 1.2044 1.8256 0.062 Uiso 1 1 calc R U . . .
H25B H 1.4219 1.3209 1.7896 0.062 Uiso 1 1 calc R U . . .
H25C H 1.4930 1.3054 1.8826 0.062 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
O28 C9 1.219(3) . ?
O19 C13 1.220(3) . ?
O27 C21 1.215(3) . ?
C9 C8 1.491(4) . ?
C9 C10 1.528(3) . ?
C13 C12 1.491(3) . ?
C13 C14 1.516(3) . ?
C8 C3 1.392(4) . ?
C8 C7 1.415(3) . ?
C11 C12 1.333(4) . ?
C11 C1 1.511(3) . ?
C3 C4 1.393(4) . ?
C3 C2 1.511(3) . ?
C10 C20 1.524(4) . ?
C10 C1 1.562(3) . ?
C20 C21 1.514(3) . ?
C7 C6 1.384(4) . ?
C21 C22 1.512(4) . ?
C4 C5 1.391(4) . ?
C1 C29 1.533(3) . ?
C1 C2 1.551(3) . ?
C14 C15 1.522(3) . ?
C15 C16 1.526(3) . ?
C6 C5 1.399(4) . ?
C6 C30 1.514(3) . ?
C16 C17 1.518(4) . ?
C16 C18 1.533(3) . ?
C24 C25 1.515(4) . ?
C24 C23 1.530(4) . ?
C24 C26 1.531(4) . ?
C22 C23 1.526(3) . ?

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
O28 C9 C8 121.0(2) . . ?
O28 C9 C10 121.6(2) . . ?
C8 C9 C10 117.4(2) . . ?
O19 C13 C12 122.7(2) . . ?
O19 C13 C14 122.0(2) . . ?
C12 C13 C14 115.2(2) . . ?
C3 C8 C7 120.2(2) . . ?
C3 C8 C9 121.2(2) . . ?
C7 C8 C9 118.5(2) . . ?
C12 C11 C1 126.3(2) . . ?
C8 C3 C4 118.6(2) . . ?
C8 C3 C2 120.5(2) . . ?
C4 C3 C2 120.8(2) . . ?
C20 C10 C9 111.2(2) . . ?
C20 C10 C1 113.5(2) . . ?
C9 C10 C1 110.6(2) . . ?
C21 C20 C10 116.1(2) . . ?
C6 C7 C8 120.9(3) . . ?
O27 C21 C22 123.2(2) . . ?
O27 C21 C20 123.2(2) . . ?
C22 C21 C20 113.6(2) . . ?
C11 C12 C13 120.9(2) . . ?
C5 C4 C3 120.7(3) . . ?
C11 C1 C29 111.9(2) . . ?
C11 C1 C2 107.43(19) . . ?
C29 C1 C2 110.6(2) . . ?
C11 C1 C10 108.4(2) . . ?
C29 C1 C10 112.00(19) . . ?
C2 C1 C10 106.3(2) . . ?
C3 C2 C1 111.9(2) . . ?
C13 C14 C15 114.0(2) . . ?
C14 C15 C16 113.9(2) . . ?
C7 C6 C5 118.1(2) . . ?
C7 C6 C30 121.1(3) . . ?
C5 C6 C30 120.8(3) . . ?
C17 C16 C15 112.3(2) . . ?
C17 C16 C18 109.5(2) . . ?
C15 C16 C18 110.1(2) . . ?
C25 C24 C23 112.3(2) . . ?
C25 C24 C26 109.7(2) . . ?
C23 C24 C26 110.5(3) . . ?
C21 C22 C23 116.0(2) . . ?
C4 C5 C6 121.3(3) . . ?
C22 C23 C24 112.9(2) . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.041

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 
'ethyl acetate and diethyl ether'
