# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_XA-1033
_database_code_depnum_ccdc_archive 'CCDC 1979004'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2020-01-20 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
(R)-1-methoxy-4-(5-(2-(4-methoxyphenoxy)propan-2-yl)cyclopent-1-en-1-yl)benzene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H26 O3'
_chemical_formula_sum            'C22 H26 O3'
_chemical_formula_weight         338.43

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                   7.7307(3)
_cell_length_b                   5.8517(2)
_cell_length_c                   20.5811(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.530(7)
_cell_angle_gamma                90
_cell_volume                     930.13(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    233(2)
_cell_measurement_reflns_used    4270
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      72.1

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.625
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_process_details   'Reqab (Rigaku-Higashi, 1998)'
_diffrn_ambient_temperature      233(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  'Osmic CMF Confocal mirrors'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'Rigaku Rapid2 curved Image plate'
_diffrn_measurement_device       
;
Crystal Goniometer chi-partial
;
_diffrn_measurement_device_type  
;
Rigaku mm007HF spider
;
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            9355
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.149
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_measurement_details      
;
scan:
	Number of images: 45
	           Slice: 20.0000 - 200.0000
	     Image width: 4.0000
	        Exp time: 300.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 45
	           Slice: 20.0000 - 200.0000
	     Image width: 4.0000
	        Exp time: 300.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 90.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 45
	           Slice: 20.0000 - 200.0000
	     Image width: 4.0000
	        Exp time: 300.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 45
	           Slice: 20.0000 - 200.0000
	     Image width: 4.0000
	        Exp time: 300.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 8
	           Slice: 149.0000 - 181.0000
	     Image width: 4.0000
	        Exp time: 300.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 90.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 5
	           Slice: 167.0000 - 188.0000
	     Image width: 4.0000
	        Exp time: 300.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 270.0000
	             XTD: 127.4000
	          2theta: 0.0000

;
_diffrn_orient_matrix_UB_11      -0.055547
_diffrn_orient_matrix_UB_12      0.017981
_diffrn_orient_matrix_UB_13      -0.044512
_diffrn_orient_matrix_UB_21      0.110901
_diffrn_orient_matrix_UB_22      0.062020
_diffrn_orient_matrix_UB_23      -0.015993
_diffrn_orient_matrix_UB_31      0.037159
_diffrn_orient_matrix_UB_32      -0.158220
_diffrn_orient_matrix_UB_33      -0.011328
_diffrn_orient_matrix_type       FS_PROCESS
_reflns_number_total             3157
_reflns_number_gt                2849
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_max     0.845
_reflns_Friedel_fraction_full    0.849

_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-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_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)+(0.0506P)²+0.0191P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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 
;
 Flack x determined using 1095 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3148
_refine_ls_number_parameters     230
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.001
_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 0.83432(16) 0.5846(3) 0.65787(6) 0.0506(4) Uani 1 1 d . . . . .
C1 C 0.8525(2) 0.5342(4) 0.76971(9) 0.0448(5) Uani 1 1 d . . . . .
H1 H 0.843767 0.702421 0.773631 0.054 Uiso 1 1 calc R U . . .
O2 O 0.69916(19) 0.5364(4) 0.39235(7) 0.0689(5) Uani 1 1 d . . . . .
C2 C 1.0471(3) 0.4661(5) 0.76801(11) 0.0593(7) Uani 1 1 d . . . . .
H2A H 1.077107 0.426853 0.723606 0.071 Uiso 1 1 calc R U . . .
H2AB H 1.121077 0.592750 0.783388 0.071 Uiso 1 1 calc R U . . .
C3 C 1.0714(3) 0.2598(6) 0.81271(11) 0.0676(8) Uani 1 1 d . . . . .
H3A H 1.068538 0.116937 0.787858 0.081 Uiso 1 1 calc R U . . .
H3AB H 1.181031 0.269173 0.838346 0.081 Uiso 1 1 calc R U . . .
O3 O 0.18823(18) 0.6031(3) 0.96477(7) 0.0587(4) Uani 1 1 d . . . . .
C4 C 0.9204(3) 0.2765(5) 0.85518(11) 0.0613(7) Uani 1 1 d . . . . .
H4 H 0.910956 0.191231 0.893561 0.074 Uiso 1 1 calc R U . . .
C5 C 0.7998(3) 0.4248(4) 0.83323(10) 0.0491(6) Uani 1 1 d . . . . .
C6 C 0.7470(3) 0.4558(4) 0.70767(9) 0.0446(5) Uani 1 1 d . . . . .
C7 C 0.7573(3) 0.2003(5) 0.69640(11) 0.0605(6) Uani 1 1 d . . . . .
H7A H 0.712880 0.120252 0.733414 0.091 Uiso 1 1 calc R U . . .
H7B H 0.876949 0.156736 0.691132 0.091 Uiso 1 1 calc R U . . .
H7C H 0.688744 0.160405 0.657442 0.091 Uiso 1 1 calc R U . . .
C9 C 0.7884(2) 0.5533(5) 0.59248(9) 0.0451(5) Uani 1 1 d . . . . .
C8 C 0.5587(2) 0.5293(5) 0.70662(10) 0.0569(7) Uani 1 1 d . . . . .
H8A H 0.500715 0.452921 0.741391 0.085 Uiso 1 1 calc R U . . .
H8B H 0.502705 0.488501 0.665132 0.085 Uiso 1 1 calc R U . . .
H8C H 0.552286 0.693396 0.712682 0.085 Uiso 1 1 calc R U . . .
C10 C 0.8689(3) 0.3887(5) 0.55683(10) 0.0552(6) Uani 1 1 d . . . . .
H10 H 0.943375 0.283132 0.578149 0.066 Uiso 1 1 calc R U . . .
C11 C 0.8414(3) 0.3764(5) 0.48977(11) 0.0561(6) Uani 1 1 d . . . . .
H11 H 0.896733 0.263201 0.465797 0.067 Uiso 1 1 calc R U . . .
C12 C 0.7324(2) 0.5318(5) 0.45875(9) 0.0503(6) Uani 1 1 d . . . . .
C13 C 0.6499(3) 0.6959(5) 0.49405(10) 0.0519(6) Uani 1 1 d . . . . .
H13 H 0.574327 0.799994 0.472655 0.062 Uiso 1 1 calc R U . . .
C14 C 0.6776(3) 0.7081(4) 0.56080(10) 0.0483(5) Uani 1 1 d . . . . .
H14 H 0.621563 0.820900 0.584681 0.058 Uiso 1 1 calc R U . . .
C15 C 0.7904(3) 0.3793(7) 0.35445(12) 0.0782(9) Uani 1 1 d . . . . .
H15A H 0.760435 0.404252 0.308741 0.117 Uiso 1 1 calc R U . . .
H15B H 0.759488 0.224605 0.366296 0.117 Uiso 1 1 calc R U . . .
H15C H 0.913945 0.401207 0.362318 0.117 Uiso 1 1 calc R U . . .
C16 C 0.6413(3) 0.4797(4) 0.86714(9) 0.0452(5) Uani 1 1 d . . . . .
C17 C 0.5718(3) 0.3251(4) 0.91075(10) 0.0507(5) Uani 1 1 d . . . . .
H17 H 0.627637 0.184160 0.918131 0.061 Uiso 1 1 calc R U . . .
C18 C 0.4241(3) 0.3729(4) 0.94320(10) 0.0507(6) Uani 1 1 d . . . . .
H18 H 0.382209 0.266569 0.972904 0.061 Uiso 1 1 calc R U . . .
C19 C 0.3371(3) 0.5770(5) 0.93226(9) 0.0476(5) Uani 1 1 d . . . . .
C20 C 0.4037(3) 0.7357(4) 0.89029(10) 0.0500(5) Uani 1 1 d . . . . .
H20 H 0.346984 0.876047 0.882960 0.060 Uiso 1 1 calc R U . . .
C21 C 0.5549(3) 0.6866(4) 0.85904(10) 0.0486(5) Uani 1 1 d . . . . .
H21 H 0.600362 0.797217 0.831427 0.058 Uiso 1 1 calc R U . . .
C22 C 0.0856(3) 0.7994(5) 0.94986(13) 0.0681(7) Uani 1 1 d . . . . .
H22A H -0.019045 0.794173 0.974153 0.102 Uiso 1 1 calc R U . . .
H22B H 0.055013 0.801897 0.903643 0.102 Uiso 1 1 calc R U . . .
H22C H 0.150758 0.936046 0.961602 0.102 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 C9 1.389(2) . ?
O1 C6 1.461(2) . ?
C1 C5 1.527(3) . ?
C1 C6 1.554(3) . ?
C1 C2 1.558(3) . ?
O2 C12 1.380(2) . ?
O2 C15 1.414(3) . ?
C2 C3 1.524(4) . ?
C3 C4 1.492(3) . ?
O3 C19 1.365(2) . ?
O3 C22 1.422(3) . ?
C4 C5 1.338(3) . ?
C5 C16 1.472(3) . ?
C6 C7 1.515(4) . ?
C6 C8 1.517(3) . ?
C9 C10 1.376(3) . ?
C9 C14 1.389(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.377(3) . ?
C12 C13 1.378(3) . ?
C13 C14 1.383(3) . ?
C16 C21 1.389(3) . ?
C16 C17 1.399(3) . ?
C17 C18 1.377(3) . ?
C18 C19 1.385(4) . ?
C19 C20 1.383(3) . ?
C20 C21 1.389(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
C9 O1 C6 120.38(15) . . ?
C5 C1 C6 115.43(19) . . ?
C5 C1 C2 101.91(18) . . ?
C6 C1 C2 112.22(16) . . ?
C12 O2 C15 117.3(2) . . ?
C3 C2 C1 106.40(19) . . ?
C4 C3 C2 102.9(2) . . ?
C19 O3 C22 117.32(18) . . ?
C5 C4 C3 113.3(2) . . ?
C4 C5 C16 124.3(2) . . ?
C4 C5 C1 110.7(2) . . ?
C16 C5 C1 124.98(19) . . ?
O1 C6 C7 111.86(18) . . ?
O1 C6 C8 108.46(18) . . ?
C7 C6 C8 109.5(2) . . ?
O1 C6 C1 100.49(16) . . ?
C7 C6 C1 112.82(19) . . ?
C8 C6 C1 113.35(17) . . ?
C10 C9 O1 120.44(19) . . ?
C10 C9 C14 119.34(18) . . ?
O1 C9 C14 119.7(2) . . ?
C9 C10 C11 120.9(2) . . ?
C12 C11 C10 119.3(2) . . ?
C11 C12 C13 120.26(19) . . ?
C11 C12 O2 123.7(2) . . ?
C13 C12 O2 116.0(2) . . ?
C12 C13 C14 120.3(2) . . ?
C13 C14 C9 119.9(2) . . ?
C21 C16 C17 116.40(19) . . ?
C21 C16 C5 122.6(2) . . ?
C17 C16 C5 121.0(2) . . ?
C18 C17 C16 122.0(2) . . ?
C17 C18 C19 120.3(2) . . ?
O3 C19 C20 125.2(2) . . ?
O3 C19 C18 115.5(2) . . ?
C20 C19 C18 119.27(19) . . ?
C19 C20 C21 119.6(2) . . ?
C16 C21 C20 122.3(2) . . ?

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
C5 C1 C2 C3 21.0(2) . . . . ?
C6 C1 C2 C3 -103.1(2) . . . . ?
C1 C2 C3 C4 -20.8(3) . . . . ?
C2 C3 C4 C5 13.2(3) . . . . ?
C3 C4 C5 C16 -177.7(2) . . . . ?
C3 C4 C5 C1 0.4(3) . . . . ?
C6 C1 C5 C4 108.4(2) . . . . ?
C2 C1 C5 C4 -13.5(3) . . . . ?
C6 C1 C5 C16 -73.5(3) . . . . ?
C2 C1 C5 C16 164.6(2) . . . . ?
C9 O1 C6 C7 55.5(3) . . . . ?
C9 O1 C6 C8 -65.4(3) . . . . ?
C9 O1 C6 C1 175.47(17) . . . . ?
C5 C1 C6 O1 -178.04(18) . . . . ?
C2 C1 C6 O1 -61.9(2) . . . . ?
C5 C1 C6 C7 -58.8(2) . . . . ?
C2 C1 C6 C7 57.4(3) . . . . ?
C5 C1 C6 C8 66.5(3) . . . . ?
C2 C1 C6 C8 -177.4(2) . . . . ?
C6 O1 C9 C10 -89.3(2) . . . . ?
C6 O1 C9 C14 99.3(2) . . . . ?
O1 C9 C10 C11 -171.1(2) . . . . ?
C14 C9 C10 C11 0.4(4) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C10 C11 C12 O2 178.8(2) . . . . ?
C15 O2 C12 C11 -3.5(3) . . . . ?
C15 O2 C12 C13 176.1(2) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
O2 C12 C13 C14 -178.72(19) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?
C10 C9 C14 C13 -0.3(3) . . . . ?
O1 C9 C14 C13 171.32(19) . . . . ?
C4 C5 C16 C21 154.2(2) . . . . ?
C1 C5 C16 C21 -23.6(3) . . . . ?
C4 C5 C16 C17 -24.4(3) . . . . ?
C1 C5 C16 C17 157.8(2) . . . . ?
C21 C16 C17 C18 1.0(3) . . . . ?
C5 C16 C17 C18 179.76(19) . . . . ?
C16 C17 C18 C19 1.4(3) . . . . ?
C22 O3 C19 C20 6.0(3) . . . . ?
C22 O3 C19 C18 -173.7(2) . . . . ?
C17 C18 C19 O3 177.28(19) . . . . ?
C17 C18 C19 C20 -2.4(3) . . . . ?
O3 C19 C20 C21 -178.6(2) . . . . ?
C18 C19 C20 C21 1.0(3) . . . . ?
C17 C16 C21 C20 -2.5(3) . . . . ?
C5 C16 C21 C20 178.8(2) . . . . ?
C19 C20 C21 C16 1.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C22 H22A O3 0.97 2.59 3.325(3) 132.8 2_557 yes

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.034




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and n-heptane'
