# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_exp_149
_database_code_depnum_ccdc_archive 'CCDC 1537709'
_audit_update_record             
;
2017-03-12 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 O3'
_chemical_formula_weight         322.38

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.18168(13)
_cell_length_b                   17.7177(4)
_cell_length_c                   18.7318(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1719.72(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.655
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23250
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.434
_diffrn_reflns_theta_max         72.597
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3408
_reflns_number_gt                3035
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0940P)²+0.1470P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_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_abs_structure_details 
;
 Flack x determined using 1168 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3408
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1490
_refine_ls_wR_factor_gt          0.1423
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
O1 O -0.1515(5) -0.45919(13) -0.15181(10) 0.0546(6) Uani 1 1 d . . . . .
O2 O -0.8406(9) -0.67718(18) 0.07242(16) 0.1027(13) Uani 1 1 d . . . . .
O3 O -0.6782(8) -0.62824(16) -0.02602(13) 0.0880(10) Uani 1 1 d . . . . .
C1 C -0.4815(5) -0.43400(14) 0.09315(13) 0.0353(5) Uani 1 1 d . . . . .
C2 C -0.4760(5) -0.39727(14) 0.15762(13) 0.0365(5) Uani 1 1 d . . . . .
C3 C -0.2919(5) -0.33717(14) 0.16989(13) 0.0365(5) Uani 1 1 d . . . . .
C4 C -0.2801(6) -0.29795(17) 0.23549(15) 0.0493(7) Uani 1 1 d . . . . .
H4 H -0.3969 -0.3104 0.2713 0.059 Uiso 1 1 calc R U . . .
C5 C -0.1021(7) -0.24215(17) 0.24805(16) 0.0550(8) Uani 1 1 d . . . . .
H5 H -0.0977 -0.2177 0.2920 0.066 Uiso 1 1 calc R U . . .
C6 C 0.0708(7) -0.22244(17) 0.19485(17) 0.0526(7) Uani 1 1 d . . . . .
H6 H 0.1920 -0.1847 0.2031 0.063 Uiso 1 1 calc R U . . .
C7 C 0.0638(6) -0.25837(14) 0.13017(16) 0.0437(6) Uani 1 1 d . . . . .
H7 H 0.1800 -0.2442 0.0948 0.052 Uiso 1 1 calc R U . . .
C8 C -0.1151(5) -0.31629(13) 0.11587(13) 0.0347(5) Uani 1 1 d . . . . .
C9 C -0.1210(5) -0.35509(12) 0.04792(12) 0.0327(5) Uani 1 1 d . . . . .
C10 C 0.0518(5) -0.33804(14) -0.00817(13) 0.0386(6) Uani 1 1 d . . . . .
H10 H 0.1772 -0.3013 -0.0009 0.046 Uiso 1 1 calc R U . . .
C11 C 0.0409(5) -0.37378(15) -0.07286(14) 0.0410(6) Uani 1 1 d . . . . .
H11 H 0.1586 -0.3618 -0.1086 0.049 Uiso 1 1 calc R U . . .
C12 C -0.1479(5) -0.42836(15) -0.08479(12) 0.0390(6) Uani 1 1 d . . . . .
C13 C -0.3165(5) -0.44771(14) -0.03127(13) 0.0380(5) Uani 1 1 d . . . . .
H13 H -0.4401 -0.4847 -0.0397 0.046 Uiso 1 1 calc R U . . .
C14 C -0.3056(5) -0.41232(13) 0.03655(12) 0.0325(5) Uani 1 1 d . . . . .
C15 C -0.6589(6) -0.41732(18) 0.21736(14) 0.0494(7) Uani 1 1 d . . . . .
H15A H -0.7821 -0.4537 0.2006 0.074 Uiso 1 1 calc R U . . .
H15B H -0.7477 -0.3727 0.2330 0.074 Uiso 1 1 calc R U . . .
H15C H -0.5632 -0.4383 0.2565 0.074 Uiso 1 1 calc R U . . .
C16 C -0.6633(6) -0.49857(15) 0.07815(14) 0.0418(6) Uani 1 1 d . . . . .
H16A H -0.7404 -0.4915 0.0314 0.050 Uiso 1 1 calc R U . . .
H16B H -0.8011 -0.4981 0.1132 0.050 Uiso 1 1 calc R U . . .
C17 C -0.5263(7) -0.57659(16) 0.08030(16) 0.0538(8) Uani 1 1 d . . . . .
H17 H -0.3683 -0.5725 0.0518 0.065 Uiso 1 1 calc R U . . .
C18 C -0.7003(8) -0.63310(17) 0.04403(17) 0.0579(8) Uani 1 1 d . . . . .
C19 C -0.4500(11) -0.6009(2) 0.1538(2) 0.0807(13) Uani 1 1 d . . . . .
H19A H -0.3297 -0.5653 0.1734 0.121 Uiso 1 1 calc R U . . .
H19B H -0.3708 -0.6499 0.1516 0.121 Uiso 1 1 calc R U . . .
H19C H -0.6004 -0.6032 0.1837 0.121 Uiso 1 1 calc R U . . .
C20 C -0.8368(16) -0.6783(3) -0.0677(3) 0.118(2) Uani 1 1 d . . . . .
H20A H -0.7808 -0.6773 -0.1166 0.178 Uiso 1 1 calc R U . . .
H20B H -1.0135 -0.6623 -0.0650 0.178 Uiso 1 1 calc R U . . .
H20C H -0.8217 -0.7287 -0.0494 0.178 Uiso 1 1 calc R U . . .
C21 C -0.3641(8) -0.5048(2) -0.17010(18) 0.0698(10) Uani 1 1 d . . . . .
H21A H -0.3530 -0.5185 -0.2196 0.105 Uiso 1 1 calc R U . . .
H21B H -0.5211 -0.4773 -0.1619 0.105 Uiso 1 1 calc R U . . .
H21C H -0.3632 -0.5496 -0.1412 0.105 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
O1 C12 1.369(3) . ?
O1 C21 1.408(4) . ?
O2 C18 1.192(5) . ?
O3 C18 1.320(4) . ?
O3 C20 1.439(6) . ?
C1 C2 1.372(3) . ?
C1 C14 1.450(3) . ?
C1 C16 1.508(3) . ?
C2 C3 1.448(4) . ?
C2 C15 1.509(4) . ?
C3 C4 1.413(4) . ?
C3 C8 1.414(3) . ?
C4 C5 1.372(5) . ?
C5 C6 1.385(5) . ?
C6 C7 1.369(4) . ?
C7 C8 1.409(4) . ?
C8 C9 1.447(3) . ?
C9 C14 1.410(3) . ?
C9 C10 1.413(3) . ?
C10 C11 1.368(4) . ?
C11 C12 1.394(4) . ?
C12 C13 1.373(4) . ?
C13 C14 1.418(3) . ?
C16 C17 1.554(4) . ?
C17 C19 1.496(4) . ?
C17 C18 1.509(4) . ?

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 C21 117.5(2) . . ?
C18 O3 C20 116.7(4) . . ?
C2 C1 C14 120.3(2) . . ?
C2 C1 C16 122.5(2) . . ?
C14 C1 C16 117.2(2) . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 C15 121.9(2) . . ?
C3 C2 C15 118.0(2) . . ?
C4 C3 C8 117.8(2) . . ?
C4 C3 C2 121.9(2) . . ?
C8 C3 C2 120.4(2) . . ?
C5 C4 C3 122.2(3) . . ?
C4 C5 C6 119.5(3) . . ?
C7 C6 C5 120.2(3) . . ?
C6 C7 C8 121.6(3) . . ?
C7 C8 C3 118.7(2) . . ?
C7 C8 C9 121.8(2) . . ?
C3 C8 C9 119.4(2) . . ?
C14 C9 C10 118.1(2) . . ?
C14 C9 C8 119.3(2) . . ?
C10 C9 C8 122.6(2) . . ?
C11 C10 C9 122.2(2) . . ?
C10 C11 C12 119.5(2) . . ?
O1 C12 C13 124.1(3) . . ?
O1 C12 C11 115.7(2) . . ?
C13 C12 C11 120.2(2) . . ?
C12 C13 C14 121.2(2) . . ?
C9 C14 C13 118.7(2) . . ?
C9 C14 C1 120.4(2) . . ?
C13 C14 C1 120.9(2) . . ?
C1 C16 C17 112.6(2) . . ?
C19 C17 C18 112.4(3) . . ?
C19 C17 C16 113.6(3) . . ?
C18 C17 C16 107.8(3) . . ?
O2 C18 O3 122.6(4) . . ?
O2 C18 C17 126.7(3) . . ?
O3 C18 C17 110.6(3) . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-2

