# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ej-3+2ch3
_audit_block_doi                 10.5517/ccdc.csd.cc1z42sz
_database_code_depnum_ccdc_archive 'CCDC 1821181'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;
_audit_creation_date             2016-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H28 O4'
_chemical_formula_sum            'C21 H28 O4'
_chemical_formula_weight         344.43
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.82030(10)
_cell_length_b                   9.9500(2)
_cell_length_c                   11.3663(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.882(2)
_cell_angle_gamma                90
_cell_volume                     964.07(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8310
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5380
_cell_measurement_theta_min      4.4540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9166
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.569
_diffrn_reflns_theta_min         4.024
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -11.00   1.00    1.00    --  -40.46 -57.00 -30.00  103
  2  ω   -117.00 -14.00   1.00    1.00    --  -40.46 -37.00-120.00  103
  3  ω   -119.00  -7.00   1.00    1.00    --  -40.46 -77.00 -30.00  112
  4  ω   -117.00 -14.00   1.00    1.00    --  -40.46 -37.00   0.00  103
  5  ω      7.00 119.00   1.00    1.00    --   40.46  77.00 -30.00  112
  6  ω      1.00  82.00   1.00    1.00    --   40.46 -99.00 120.00   81
  7  ω      1.00  82.00   1.00    1.00    --   40.46 -99.00-150.00   81
  8  ω     74.00 178.00   1.00    1.00    --  107.48  77.00 -90.00  104
  9  ω     74.00 178.00   1.00    1.00    --  107.48  77.00 -60.00  104
 10  ω     74.00 178.00   1.00    1.00    --  107.48  77.00  30.00  104
 11  ω     80.00 178.00   1.00    1.00    --  107.48  45.00  30.00   98
 12  ω     23.00 109.00   1.00    1.00    --  107.48 -94.00   0.00   86
 13  ω     23.00 109.00   1.00    1.00    --  107.48 -94.00  60.00   86
 14  ω     77.00 178.00   1.00    1.00    --  107.48  61.00 -30.00  101
 15  ω     77.00 178.00   1.00    1.00    --  107.48  61.00   0.00  101
 16  ω     77.00 178.00   1.00    1.00    --  107.48  61.00  30.00  101
 17  ω     77.00 178.00   1.00    1.00    --  107.48  61.00 -60.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1308471000
_diffrn_orient_matrix_UB_12      -0.0433345000
_diffrn_orient_matrix_UB_13      -0.0593470000
_diffrn_orient_matrix_UB_21      0.1173788000
_diffrn_orient_matrix_UB_22      -0.0050089000
_diffrn_orient_matrix_UB_23      0.1264567000
_diffrn_orient_matrix_UB_31      -0.0420328000
_diffrn_orient_matrix_UB_32      -0.1484931000
_diffrn_orient_matrix_UB_33      0.0131508000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.768
_reflns_number_gt                3412
_reflns_number_total             3438
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1382 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_coef       0.0132(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0511P)²+0.1358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0804
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C2'(H2'), C6'(H6'), C9A(H9AA)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C3'(H3'A,H3'B,H3'C), C4'(H4'A,H4'B,H4'C), C5'(H5'A,H5'B,H5'C), C7'(H7'A,H7'B,
 H7'C), C8'(H8'A,H8'B,H8'C), C9'(H9'A,H9'B,H9'C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 1.36096(15) 0.70165(15) 0.90445(12) 0.0296(3) Uani 1 1 d . . . . .
O2 O 1.47653(14) 0.73054(14) 0.72644(12) 0.0265(3) Uani 1 1 d . . . . .
H2 H 1.4724 0.7083 0.7950 0.040 Uiso 1 1 calc GR . . . .
O3 O 1.17723(13) 0.95323(14) 0.37253(11) 0.0236(3) Uani 1 1 d . . . . .
O5 O 0.95046(13) 0.89424(13) 0.69269(11) 0.0231(3) Uani 1 1 d . . . . .
C1 C 1.19376(19) 0.90095(17) 0.48539(16) 0.0200(3) Uani 1 1 d . . . . .
C2 C 1.33130(19) 0.83917(18) 0.55190(16) 0.0219(4) Uani 1 1 d . . . . .
H2A H 1.4166 0.8305 0.5185 0.026 Uiso 1 1 calc R . . . .
C3 C 1.34033(19) 0.79059(18) 0.66824(16) 0.0216(4) Uani 1 1 d . . . . .
C4 C 1.2150(2) 0.80348(18) 0.72527(16) 0.0208(3) Uani 1 1 d . . . . .
C6 C 0.73750(19) 0.80174(19) 0.54355(17) 0.0233(4) Uani 1 1 d . . . . .
H6 H 0.6906 0.7593 0.5980 0.028 Uiso 1 1 calc R . . . .
C7 C 0.72385(19) 0.74360(19) 0.43643(16) 0.0241(4) Uani 1 1 d . . . . .
H7 H 0.6742 0.6605 0.4234 0.029 Uiso 1 1 calc R . . . .
C8 C 0.7830(2) 0.80241(19) 0.33396(16) 0.0220(4) Uani 1 1 d . . . . .
H8 H 0.8826 0.7582 0.3348 0.026 Uiso 1 1 calc R . . . .
C9 C 0.81664(18) 0.95188(19) 0.35879(15) 0.0217(3) Uani 1 1 d . . . . .
H9A H 0.7178 1.0001 0.3418 0.026 Uiso 1 1 calc R . . . .
H9B H 0.8754 0.9851 0.3035 0.026 Uiso 1 1 calc R . . . .
C1' C 1.2365(2) 0.75835(19) 0.85080(16) 0.0238(4) Uani 1 1 d . . . . .
C2' C 1.1108(2) 0.7753(2) 0.91910(16) 0.0286(4) Uani 1 1 d . . . . .
H2' H 1.0590 0.8622 0.8965 0.034 Uiso 1 1 calc R . . . .
C3' C 1.1849(3) 0.7753(4) 1.05599(19) 0.0528(7) Uani 1 1 d . . . . .
H3'A H 1.2329 0.6896 1.0801 0.079 Uiso 1 1 calc GR . . . .
H3'B H 1.1055 0.7918 1.0982 0.079 Uiso 1 1 calc GR . . . .
H3'C H 1.2631 0.8446 1.0758 0.079 Uiso 1 1 calc GR . . . .
C4' C 0.9881(2) 0.6640(2) 0.8812(2) 0.0338(5) Uani 1 1 d . . . . .
H4'A H 0.9496 0.6632 0.7942 0.051 Uiso 1 1 calc GR . . . .
H4'B H 0.9027 0.6803 0.9173 0.051 Uiso 1 1 calc GR . . . .
H4'C H 1.0351 0.5788 0.9084 0.051 Uiso 1 1 calc GR . . . .
C5' C 0.7234(2) 1.0348(2) 0.62673(17) 0.0281(4) Uani 1 1 d . . . . .
H5'A H 0.6764 0.9948 0.6857 0.042 Uiso 1 1 calc GR . . . .
H5'B H 0.6425 1.0662 0.5587 0.042 Uiso 1 1 calc GR . . . .
H5'C H 0.7880 1.1091 0.6632 0.042 Uiso 1 1 calc GR . . . .
C6' C 0.6679(2) 0.77527(19) 0.20829(17) 0.0251(4) Uani 1 1 d . . . . .
H6' H 0.5641 0.8078 0.2113 0.030 Uiso 1 1 calc R . . . .
C7' C 0.6540(3) 0.6249(2) 0.1789(2) 0.0384(5) Uani 1 1 d . . . . .
H7'A H 0.5773 0.6112 0.1029 0.058 Uiso 1 1 calc GR . . . .
H7'B H 0.6222 0.5780 0.2424 0.058 Uiso 1 1 calc GR . . . .
H7'C H 0.7537 0.5912 0.1729 0.058 Uiso 1 1 calc GR . . . .
C8' C 0.7148(2) 0.8491(2) 0.10518(18) 0.0316(4) Uani 1 1 d . . . . .
H8'A H 0.8205 0.8256 0.1055 0.047 Uiso 1 1 calc GR . . . .
H8'B H 0.7081 0.9443 0.1165 0.047 Uiso 1 1 calc GR . . . .
H8'C H 0.6453 0.8238 0.0287 0.047 Uiso 1 1 calc GR . . . .
C9' C 1.3146(2) 0.9582(2) 0.32792(17) 0.0271(4) Uani 1 1 d . . . . .
H9'A H 1.3959 1.0061 0.3848 0.041 Uiso 1 1 calc GR . . . .
H9'B H 1.2907 1.0033 0.2507 0.041 Uiso 1 1 calc GR . . . .
H9'C H 1.3494 0.8684 0.3183 0.041 Uiso 1 1 calc GR . . . .
C4A C 1.07965(18) 0.86763(18) 0.65251(15) 0.0198(3) Uani 1 1 d . . . . .
C5A C 0.82306(18) 0.93116(19) 0.58358(16) 0.0219(4) Uani 1 1 d . . . . .
C9A C 0.90891(18) 0.98217(17) 0.48950(15) 0.0208(4) Uani 1 1 d . . . . .
H9AA H 0.9241 1.0795 0.4990 0.025 Uiso 1 1 calc R . . . .
C9B C 1.06605(18) 0.91263(16) 0.53538(16) 0.0202(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
O1 C1' 1.246(2) . ?
O2 C3 1.353(2) . ?
O3 C1 1.357(2) . ?
O3 C9' 1.4294(19) . ?
O5 C4A 1.3581(19) . ?
O5 C5A 1.490(2) . ?
C1 C2 1.396(2) . ?
C1 C9B 1.391(2) . ?
C2 C3 1.391(2) . ?
C3 C4 1.424(2) . ?
C4 C1' 1.461(2) . ?
C4 C4A 1.418(2) . ?
C6 C7 1.325(3) . ?
C6 C5A 1.503(3) . ?
C7 C8 1.511(2) . ?
C8 C9 1.529(3) . ?
C8 C6' 1.549(2) . ?
C9 C9A 1.529(2) . ?
C1' C2' 1.517(2) . ?
C2' C3' 1.525(3) . ?
C2' C4' 1.531(3) . ?
C5' C5A 1.516(2) . ?
C6' C7' 1.531(3) . ?
C6' C8' 1.527(3) . ?
C4A C9B 1.380(2) . ?
C5A C9A 1.546(2) . ?
C9A C9B 1.517(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
C1 O3 C9' 116.97(13) . . ?
C4A O5 C5A 106.66(12) . . ?
O3 C1 C2 123.23(15) . . ?
O3 C1 C9B 116.91(15) . . ?
C9B C1 C2 119.86(16) . . ?
C3 C2 C1 119.83(15) . . ?
O2 C3 C2 116.44(15) . . ?
O2 C3 C4 120.87(15) . . ?
C2 C3 C4 122.68(15) . . ?
C3 C4 C1' 119.73(15) . . ?
C4A C4 C3 114.27(15) . . ?
C4A C4 C1' 125.92(15) . . ?
C7 C6 C5A 124.90(16) . . ?
C6 C7 C8 124.84(17) . . ?
C7 C8 C9 108.87(15) . . ?
C7 C8 C6' 111.66(14) . . ?
C9 C8 C6' 112.96(14) . . ?
C8 C9 C9A 113.62(14) . . ?
O1 C1' C4 119.62(16) . . ?
O1 C1' C2' 117.90(16) . . ?
C4 C1' C2' 122.47(15) . . ?
C1' C2' C3' 110.10(15) . . ?
C1' C2' C4' 109.40(16) . . ?
C3' C2' C4' 112.0(2) . . ?
C7' C6' C8 111.61(15) . . ?
C8' C6' C8 112.42(15) . . ?
C8' C6' C7' 108.97(17) . . ?
O5 C4A C4 123.04(15) . . ?
O5 C4A C9B 112.86(14) . . ?
C9B C4A C4 124.08(15) . . ?
O5 C5A C6 104.69(14) . . ?
O5 C5A C5' 105.94(14) . . ?
O5 C5A C9A 104.95(12) . . ?
C6 C5A C5' 113.13(14) . . ?
C6 C5A C9A 111.65(14) . . ?
C5' C5A C9A 115.35(15) . . ?
C9 C9A C5A 111.98(13) . . ?
C9B C9A C9 117.09(14) . . ?
C9B C9A C5A 100.31(13) . . ?
C1 C9B C9A 131.47(16) . . ?
C4A C9B C1 119.21(15) . . ?
C4A C9B C9A 108.96(14) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.624
_oxdiff_exptl_absorpt_empirical_full_min 0.409
