# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_JTM1728_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2233480'
loop_
_audit_author_name
_audit_author_address
'Joel T. Mague'
;Tulane University
United States of America
;
_audit_update_record             
;
2022-12-29 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        
;
3-(3-chloro-4-fluorophenoxy)-1-(tetrahydrofuran-2-yl)propan-1-ol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 Cl F O3'
_chemical_formula_sum            'C12 H14 Cl F O3'
_chemical_formula_weight         260.68

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   4.9861(2)
_cell_length_b                   11.0524(5)
_cell_length_c                   11.1934(5)
_cell_angle_alpha                94.348(2)
_cell_angle_beta                 97.815(1)
_cell_angle_gamma                99.176(1)
_cell_volume                     600.30(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      4.0063
_cell_measurement_theta_max      74.4741

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   0.632
_exptl_transmission_factor_max   0.754
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.135
_exptl_absorpt_coefficient_mu    2.911
_shelx_estimated_absorpt_T_min   0.568
_shelx_estimated_absorpt_T_max   0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_T_max  0.69

_exptl_special_details           
;
The diffraction data were obtained from 13 sets of frames,
each of width 0.5° in ω or φ, collected with scan parameters
determined by the "strategy" routine in APEX4. The scan
time was θ-dependent and ranged from 4 to 15 sec/frame.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC I\mS micro----focus source'
_diffrn_source_type              ?
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50
_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device       'Bruker D8 VENTURE PHOTON 3 CPAD'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 3 CPAD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            11951
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.006
_diffrn_reflns_theta_max         74.466
_diffrn_reflns_theta_full        70.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2412
_reflns_number_gt                2327
_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       'APEX4 (Bruker, 2021)'
_computing_cell_refinement       'SAINT (Bruker, 2021)'
_computing_data_reduction        'SAINT (Bruker, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2018/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2021)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 1.00 Å) and included 
as riding contributions with isotropic displacement parameters 1.2 - 1.5 
times those of the attached atoms. That attached to oxygen was placed in a 
location derived from a difference map and was refined independently. One 
affected by the beam stop or the low temperature nozzle wae omitted from 
the final refinement.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0605P)²+0.1513P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2412
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
Cl1 Cl 1.11344(7) 0.44586(3) 0.27570(3) 0.04120(14) Uani 1 1 d . . . . .
F1 F 1.00488(18) 0.19015(8) 0.16785(7) 0.0415(2) Uani 1 1 d . . . . .
O1 O 0.3988(2) 0.28176(9) 0.52755(9) 0.0342(2) Uani 1 1 d . . . . .
O2 O -0.0580(2) 0.13053(9) 0.71267(10) 0.0360(2) Uani 1 1 d . . . . .
H2A H -0.183(5) 0.152(2) 0.743(2) 0.060(6) Uiso 1 1 d . . . . .
O3 O 0.50551(19) 0.19029(9) 0.81613(8) 0.0338(2) Uani 1 1 d . . . . .
C1 C 0.5391(3) 0.25236(12) 0.43576(12) 0.0303(3) Uani 1 1 d . . . . .
C2 C 0.7256(3) 0.34910(12) 0.40552(12) 0.0319(3) Uani 1 1 d . . . . .
H2 H 0.746253 0.429155 0.446749 0.038 Uiso 1 1 calc R U . . .
C3 C 0.8799(3) 0.32749(12) 0.31519(12) 0.0320(3) Uani 1 1 d . . . . .
C4 C 0.8498(3) 0.21031(13) 0.25565(12) 0.0337(3) Uani 1 1 d . . . . .
C5 C 0.6636(3) 0.11510(13) 0.28351(12) 0.0347(3) Uani 1 1 d . . . . .
H5 H 0.643527 0.035485 0.241417 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5043(3) 0.13532(12) 0.37345(12) 0.0326(3) Uani 1 1 d . . . . .
H6 H 0.373074 0.070098 0.392310 0.039 Uiso 1 1 calc R U . . .
C7 C 0.2221(3) 0.18251(12) 0.56752(12) 0.0308(3) Uani 1 1 d . . . . .
H7A H 0.324798 0.115251 0.587461 0.037 Uiso 1 1 calc R U . . .
H7B H 0.066034 0.149328 0.502811 0.037 Uiso 1 1 calc R U . . .
C8 C 0.1175(3) 0.23268(12) 0.67909(12) 0.0313(3) Uani 1 1 d . . . . .
H8 H 0.007683 0.298079 0.656980 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3515(3) 0.28599(12) 0.78107(12) 0.0321(3) Uani 1 1 d . . . . .
H9 H 0.476960 0.352892 0.750887 0.038 Uiso 1 1 calc R U . . .
C10 C 0.2631(3) 0.33720(14) 0.89774(14) 0.0412(3) Uani 1 1 d . . . . .
H10A H 0.278002 0.427862 0.901741 0.049 Uiso 1 1 calc R U . . .
H10B H 0.071683 0.300126 0.903735 0.049 Uiso 1 1 calc R U . . .
C11 C 0.4650(3) 0.30015(14) 0.99740(13) 0.0410(3) Uani 1 1 d . . . . .
H11A H 0.641705 0.358272 1.012096 0.049 Uiso 1 1 calc R U . . .
H11B H 0.387933 0.294242 1.074143 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4972(3) 0.17501(14) 0.94184(13) 0.0415(3) Uani 1 1 d . . . . .
H12A H 0.669109 0.150789 0.980048 0.050 Uiso 1 1 calc R U . . .
H12B H 0.339874 0.111414 0.951540 0.050 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
Cl1 C3 1.7335(14) . ?
F1 C4 1.3573(16) . ?
O1 C1 1.3669(17) . ?
O1 C7 1.4327(16) . ?
O2 C8 1.4212(16) . ?
O2 H2A 0.81(2) . ?
O3 C12 1.4352(17) . ?
O3 C9 1.4498(16) . ?
C1 C2 1.3950(19) . ?
C1 C6 1.3959(19) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(2) . ?
C4 C5 1.372(2) . ?
C5 C6 1.391(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5178(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5259(19) . ?
C8 H8 1.0000 . ?
C9 C10 1.5311(19) . ?
C9 H9 1.0000 . ?
C10 C11 1.524(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.514(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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 O1 C7 116.80(10) . . ?
C8 O2 H2A 111.2(17) . . ?
C12 O3 C9 109.25(10) . . ?
O1 C1 C2 115.37(11) . . ?
O1 C1 C6 124.29(12) . . ?
C2 C1 C6 120.33(13) . . ?
C3 C2 C1 119.41(12) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.05(12) . . ?
C2 C3 Cl1 120.46(10) . . ?
C4 C3 Cl1 119.48(11) . . ?
F1 C4 C5 119.71(12) . . ?
F1 C4 C3 119.40(12) . . ?
C5 C4 C3 120.89(13) . . ?
C4 C5 C6 119.91(12) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.37(12) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
O1 C7 C8 107.75(10) . . ?
O1 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
O1 C7 H7B 110.2 . . ?
C8 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
O2 C8 C7 104.76(10) . . ?
O2 C8 C9 111.87(11) . . ?
C7 C8 C9 112.02(11) . . ?
O2 C8 H8 109.4 . . ?
C7 C8 H8 109.4 . . ?
C9 C8 H8 109.4 . . ?
O3 C9 C8 109.49(10) . . ?
O3 C9 C10 105.50(11) . . ?
C8 C9 C10 115.33(12) . . ?
O3 C9 H9 108.8 . . ?
C8 C9 H9 108.8 . . ?
C10 C9 H9 108.8 . . ?
C11 C10 C9 103.44(12) . . ?
C11 C10 H10A 111.1 . . ?
C9 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.0 . . ?
C12 C11 C10 100.62(12) . . ?
C12 C11 H11A 111.6 . . ?
C10 C11 H11A 111.6 . . ?
C12 C11 H11B 111.6 . . ?
C10 C11 H11B 111.6 . . ?
H11A C11 H11B 109.4 . . ?
O3 C12 C11 104.59(12) . . ?
O3 C12 H12A 110.8 . . ?
C11 C12 H12A 110.8 . . ?
O3 C12 H12B 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?

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
C7 O1 C1 C2 -175.09(11) . . . . ?
C7 O1 C1 C6 5.27(18) . . . . ?
O1 C1 C2 C3 178.95(11) . . . . ?
C6 C1 C2 C3 -1.39(19) . . . . ?
C1 C2 C3 C4 -0.27(19) . . . . ?
C1 C2 C3 Cl1 -179.96(10) . . . . ?
C2 C3 C4 F1 -179.33(12) . . . . ?
Cl1 C3 C4 F1 0.36(17) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
Cl1 C3 C4 C5 -178.98(10) . . . . ?
F1 C4 C5 C6 179.96(12) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C1 -1.0(2) . . . . ?
O1 C1 C6 C5 -178.36(12) . . . . ?
C2 C1 C6 C5 2.0(2) . . . . ?
C1 O1 C7 C8 172.83(10) . . . . ?
O1 C7 C8 O2 179.24(10) . . . . ?
O1 C7 C8 C9 -59.29(13) . . . . ?
C12 O3 C9 C8 -120.45(12) . . . . ?
C12 O3 C9 C10 4.24(14) . . . . ?
O2 C8 C9 O3 56.78(14) . . . . ?
C7 C8 C9 O3 -60.51(14) . . . . ?
O2 C8 C9 C10 -61.99(15) . . . . ?
C7 C8 C9 C10 -179.27(11) . . . . ?
O3 C9 C10 C11 21.01(14) . . . . ?
C8 C9 C10 C11 141.97(12) . . . . ?
C9 C10 C11 C12 -36.61(15) . . . . ?
C9 O3 C12 C11 -28.16(15) . . . . ?
C10 C11 C12 O3 39.93(15) . . . . ?

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
O2 H2A O3 0.81(2) 1.94(2) 2.7464(14) 175(2) 1_455 yes
C5 H5 O3 0.95 2.50 3.4078(17) 161 2_656 yes
C6 H6 O2 0.95 2.60 3.3789(16) 140 2_556 yes
C7 H7B Cg2 0.99 2.70 3.5104(15) 139 1_455 y
C9 H9 Cl1 1.00 2.83 3.8118(14) 166 2_766 yes
C11 H11B F1 0.99 2.47 3.3217(18) 144 1_456 yes
C12 H12A F1 0.99 2.47 3.3007(18) 142 1_556 yes
_iucr_geom_hbonds_special_details 
;
Cg2 is the centroid of the C1...C6 benzene ring.
;


_refine_diff_density_max         0.415
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_JTM1683_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2233482'
loop_
_audit_author_name
_audit_author_address
'Joel T. Mague'
;Tulane University
United States of America
;
_audit_update_record             
;
2022-12-29 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        
;
(1S)-4-(4-methoxyphenyl)-1-(tetrahydrofuran-2-yl)butan-1-ol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H22 O3'
_chemical_formula_sum            'C15 H22 O3'
_chemical_formula_weight         250.32

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                   8.6600(5)
_cell_length_b                   5.9392(3)
_cell_length_c                   26.8603(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.256(3)
_cell_angle_gamma                90
_cell_volume                     1379.29(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9658
_cell_measurement_theta_min      3.2960
_cell_measurement_theta_max      72.3353
_cell_measurement_temperature    150(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   0.697
_exptl_transmission_factor_max   0.857
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.660
_shelx_estimated_absorpt_T_min   0.841
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
The diffraction data were obtained from 14 sets of frames,
each of width 0.5° in ω or φ, collected with scan parameters
determined by the "strategy" routine in APEX4. The scan
time was θ-dependent, being 5-10 sec/frame.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'INCOATEC I\mS micro----focus source'
_diffrn_source_type              ?
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50
_diffrn_radiation_monochromator  mirror

_diffrn_measurement_device       'Bruker D8 VENTURE PHOTON 3 CPAD'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 3 CPAD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            22882
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.296
_diffrn_reflns_theta_max         72.502
_diffrn_reflns_theta_full        72.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2709
_reflns_number_gt                2427
_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       'APEX4 (Bruker, 2021)'
_computing_cell_refinement       'SAINT (Bruker, 2021)'
_computing_data_reduction        'SAINT (Bruker, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  
'SHELXL-2018/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2012)'
_computing_publication_material  'SHELXTL (Bruker, 2021)'

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. H-atoms attached to carbon 
were placed in calculated positions (C---H = 0.95 - 1.00 Å) and included 
as riding contributions with isotropic displacement parameters 1.2 - 1.5 
times those of the attached atoms. That attached to oxygen in the major 
component was placed in a location derived from a difference map and was 
refined with a DFIX 0.84 0.01 instruction. That attached to oxygen in the 
minor component was included with an HFIX 147 instruction. The hydroxyl 
group and its attached THF moiety are disordered over two resolved sites 
in a 0.806(3)/0.194(3) ratio with restraints applied so that the geometries 
of the two components be comparable. At the end of the refinement of this 
model, it appeared that there might be further disorder but this was 
considered too minor to model.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1106P)²+2.3061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2709
_refine_ls_number_parameters     190
_refine_ls_number_restraints     65
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0970
_refine_ls_wR_factor_ref         0.2552
_refine_ls_wR_factor_gt          0.2500
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.090
_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 0.6271(3) 0.1831(4) 0.81928(8) 0.0529(6) Uani 1 1 d . . . . .
C1 C 0.7245(4) -0.0072(7) 0.82238(15) 0.0591(9) Uani 1 1 d . . . . .
H1A H 0.663658 -0.142855 0.814344 0.089 Uiso 1 1 calc R U . . .
H1B H 0.771847 -0.019792 0.856282 0.089 Uiso 1 1 calc R U . . .
H1C H 0.805761 0.008740 0.798673 0.089 Uiso 1 1 calc R U . . .
C2 C 0.5424(3) 0.2152(5) 0.77488(11) 0.0423(7) Uani 1 1 d . . . . .
C3 C 0.4513(4) 0.4079(5) 0.77173(12) 0.0455(7) Uani 1 1 d . . . . .
H3 H 0.450895 0.508142 0.799275 0.055 Uiso 1 1 calc R U . . .
C4 C 0.3610(4) 0.4549(5) 0.72875(12) 0.0447(7) Uani 1 1 d . . . . .
H4 H 0.299536 0.587433 0.727277 0.054 Uiso 1 1 calc R U . . .
C5 C 0.3587(3) 0.3114(5) 0.68757(11) 0.0427(7) Uani 1 1 d . . . . .
C6 C 0.4512(4) 0.1201(5) 0.69169(12) 0.0466(8) Uani 1 1 d . . . . .
H6 H 0.451647 0.019643 0.664179 0.056 Uiso 1 1 calc R U . . .
C7 C 0.5428(4) 0.0700(5) 0.73434(12) 0.0462(7) Uani 1 1 d . . . . .
H7 H 0.604979 -0.061912 0.735778 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2645(4) 0.3649(6) 0.64041(12) 0.0481(8) Uani 1 1 d . . . . .
H8A H 0.165917 0.435616 0.648984 0.058 Uiso 1 1 calc R U . . .
H8B H 0.239327 0.223099 0.622329 0.058 Uiso 1 1 calc R U . . .
C9 C 0.3494(4) 0.5236(5) 0.60616(12) 0.0464(7) Uani 1 1 d . . . . .
H9A H 0.366629 0.669533 0.623393 0.056 Uiso 1 1 calc R U . . .
H9B H 0.452090 0.458600 0.600265 0.056 Uiso 1 1 calc R U . . .
C10 C 0.2635(4) 0.5657(5) 0.55617(13) 0.0484(8) Uani 1 1 d D . . . .
H10A H 0.250605 0.420497 0.538307 0.058 Uiso 1 1 calc R U . A 1
H10B H 0.158979 0.623770 0.562129 0.058 Uiso 1 1 calc R U . A 1
O2 O 0.3230(4) 0.9498(5) 0.54393(11) 0.0538(8) Uani 0.806(3) 1 d D . P B 1
H2 H 0.418(2) 0.983(10) 0.545(2) 0.081 Uiso 0.806(3) 1 d D U P B 1
O3 O 0.3796(3) 0.8720(5) 0.43982(11) 0.0525(8) Uani 0.806(3) 1 d D . P B 1
C11 C 0.3433(4) 0.7304(6) 0.52314(14) 0.0426(9) Uani 0.806(3) 1 d D U P B 1
H11 H 0.456314 0.694918 0.524887 0.051 Uiso 0.806(3) 1 calc R U P B 1
C12 C 0.2851(4) 0.7285(6) 0.46887(14) 0.0429(8) Uani 0.806(3) 1 d D U P B 1
H12 H 0.292549 0.571161 0.455980 0.051 Uiso 0.806(3) 1 calc R U P B 1
C13 C 0.1155(5) 0.8130(10) 0.4583(2) 0.0649(14) Uani 0.806(3) 1 d D U P B 1
H13A H 0.054301 0.704764 0.437201 0.078 Uiso 0.806(3) 1 calc R U P B 1
H13B H 0.063300 0.837917 0.489655 0.078 Uiso 0.806(3) 1 calc R U P B 1
C14 C 0.1384(7) 1.0302(12) 0.4312(2) 0.0837(17) Uani 0.806(3) 1 d D U P B 1
H14A H 0.055741 1.050294 0.404606 0.100 Uiso 0.806(3) 1 calc R U P B 1
H14B H 0.134285 1.158446 0.454672 0.100 Uiso 0.806(3) 1 calc R U P B 1
C15 C 0.2858(5) 1.0222(8) 0.41014(17) 0.0551(10) Uani 0.806(3) 1 d D U P B 1
H15A H 0.274847 0.967796 0.375279 0.066 Uiso 0.806(3) 1 calc R U P B 1
H15B H 0.333020 1.174001 0.410282 0.066 Uiso 0.806(3) 1 calc R U P B 1
O2A O 0.4607(11) 0.7026(18) 0.5091(4) 0.0538(8) Uani 0.194(3) 1 d D . P B 2
H2A H 0.516894 0.622017 0.528418 0.081 Uiso 0.194(3) 1 calc R U P B 2
O3A O 0.1538(13) 0.7506(16) 0.4596(4) 0.0525(8) Uani 0.194(3) 1 d D . P B 2
C11A C 0.3288(11) 0.7767(12) 0.5343(3) 0.0426(9) Uani 0.194(3) 1 d D . P B 2
H11A H 0.363161 0.881339 0.561918 0.051 Uiso 0.194(3) 1 calc R U P B 2
C12A C 0.2149(10) 0.8966(14) 0.4989(3) 0.0429(8) Uani 0.194(3) 1 d D . P B 2
H12A H 0.126703 0.949589 0.518325 0.051 Uiso 0.194(3) 1 calc R U P B 2
C13A C 0.2801(16) 1.1035(18) 0.4709(5) 0.0649(14) Uani 0.194(3) 1 d D U P B 2
H13C H 0.249020 1.246831 0.486300 0.078 Uiso 0.194(3) 1 calc R U P B 2
H13D H 0.394297 1.097490 0.470799 0.078 Uiso 0.194(3) 1 calc R U P B 2
C14A C 0.207(3) 1.078(3) 0.4193(5) 0.0837(17) Uani 0.194(3) 1 d D U P B 2
H14C H 0.146541 1.214962 0.410152 0.100 Uiso 0.194(3) 1 calc R U P B 2
H14D H 0.288644 1.060475 0.395194 0.100 Uiso 0.194(3) 1 calc R U P B 2
C15A C 0.1085(17) 0.886(2) 0.4175(4) 0.0551(10) Uani 0.194(3) 1 d D U P B 2
H15C H -0.000930 0.932609 0.418838 0.066 Uiso 0.194(3) 1 calc R U P B 2
H15D H 0.120280 0.800946 0.386215 0.066 Uiso 0.194(3) 1 calc R U P B 2


_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 C2 1.377(4) . ?
O1 C1 1.410(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.389(4) . ?
C2 C3 1.390(4) . ?
C3 C4 1.385(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(5) . ?
C5 C8 1.501(5) . ?
C6 C7 1.389(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.534(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.519(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11A 1.508(5) . ?
C10 C11 1.514(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
O2 C11 1.433(4) . ?
O2 H2 0.841(10) . ?
O3 C15 1.420(5) . ?
O3 C12 1.441(4) . ?
C11 C12 1.515(5) . ?
C11 H11 1.0000 . ?
C12 C13 1.563(6) . ?
C12 H12 1.0000 . ?
C13 C14 1.499(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.426(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O2A C11A 1.430(5) . ?
O2A H2A 0.8400 . ?
O3A C15A 1.426(5) . ?
O3A C12A 1.443(5) . ?
C11A C12A 1.509(5) . ?
C11A H11A 1.0000 . ?
C12A C13A 1.562(6) . ?
C12A H12A 1.0000 . ?
C13A C14A 1.497(8) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C14A C15A 1.426(7) . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?

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
C2 O1 C1 116.7(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 124.6(3) . . ?
O1 C2 C3 116.1(3) . . ?
C7 C2 C3 119.3(3) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 117.0(3) . . ?
C6 C5 C8 121.5(3) . . ?
C4 C5 C8 121.5(3) . . ?
C7 C6 C5 122.7(3) . . ?
C7 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
C6 C7 C2 119.1(3) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C5 C8 C9 112.3(3) . . ?
C5 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C5 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 113.8(3) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11A C10 C9 107.8(4) . . ?
C11 C10 C9 114.1(3) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 O2 H2 95(4) . . ?
C15 O3 C12 110.6(3) . . ?
O2 C11 C10 106.8(3) . . ?
O2 C11 C12 109.9(3) . . ?
C10 C11 C12 114.9(3) . . ?
O2 C11 H11 108.3 . . ?
C10 C11 H11 108.3 . . ?
C12 C11 H11 108.3 . . ?
O3 C12 C11 110.4(3) . . ?
O3 C12 C13 105.6(3) . . ?
C11 C12 C13 115.5(3) . . ?
O3 C12 H12 108.4 . . ?
C11 C12 H12 108.4 . . ?
C13 C12 H12 108.4 . . ?
C14 C13 C12 102.4(4) . . ?
C14 C13 H13A 111.3 . . ?
C12 C13 H13A 111.3 . . ?
C14 C13 H13B 111.3 . . ?
C12 C13 H13B 111.3 . . ?
H13A C13 H13B 109.2 . . ?
C15 C14 C13 108.0(4) . . ?
C15 C14 H14A 110.1 . . ?
C13 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
C13 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
O3 C15 C14 107.1(4) . . ?
O3 C15 H15A 110.3 . . ?
C14 C15 H15A 110.3 . . ?
O3 C15 H15B 110.3 . . ?
C14 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
C11A O2A H2A 109.5 . . ?
C15A O3A C12A 108.3(4) . . ?
O2A C11A C10 104.8(8) . . ?
O2A C11A C12A 111.0(4) . . ?
C10 C11A C12A 113.1(6) . . ?
O2A C11A H11A 109.3 . . ?
C10 C11A H11A 109.3 . . ?
C12A C11A H11A 109.3 . . ?
O3A C12A C11A 112.1(4) . . ?
O3A C12A C13A 104.4(4) . . ?
C11A C12A C13A 115.7(4) . . ?
O3A C12A H12A 108.1 . . ?
C11A C12A H12A 108.1 . . ?
C13A C12A H12A 108.1 . . ?
C14A C13A C12A 102.8(4) . . ?
C14A C13A H13C 111.2 . . ?
C12A C13A H13C 111.2 . . ?
C14A C13A H13D 111.2 . . ?
C12A C13A H13D 111.2 . . ?
H13C C13A H13D 109.1 . . ?
C15A C14A C13A 109.4(5) . . ?
C15A C14A H14C 109.8 . . ?
C13A C14A H14C 109.8 . . ?
C15A C14A H14D 109.8 . . ?
C13A C14A H14D 109.8 . . ?
H14C C14A H14D 108.2 . . ?
O3A C15A C14A 106.7(5) . . ?
O3A C15A H15C 110.4 . . ?
C14A C15A H15C 110.4 . . ?
O3A C15A H15D 110.4 . . ?
C14A C15A H15D 110.4 . . ?
H15C C15A H15D 108.6 . . ?

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
C1 O1 C2 C7 2.4(4) . . . . ?
C1 O1 C2 C3 -177.7(3) . . . . ?
O1 C2 C3 C4 -179.6(3) . . . . ?
C7 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C5 C8 -178.3(3) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C8 C5 C6 C7 178.1(3) . . . . ?
C5 C6 C7 C2 0.3(5) . . . . ?
O1 C2 C7 C6 179.4(3) . . . . ?
C3 C2 C7 C6 -0.4(4) . . . . ?
C6 C5 C8 C9 -94.2(3) . . . . ?
C4 C5 C8 C9 83.9(4) . . . . ?
C5 C8 C9 C10 175.1(3) . . . . ?
C8 C9 C10 C11A 161.1(5) . . . . ?
C8 C9 C10 C11 177.4(3) . . . . ?
C9 C10 C11 O2 -73.5(4) . . . . ?
C9 C10 C11 C12 164.3(3) . . . . ?
C15 O3 C12 C11 -129.8(3) . . . . ?
C15 O3 C12 C13 -4.3(4) . . . . ?
O2 C11 C12 O3 65.9(4) . . . . ?
C10 C11 C12 O3 -173.6(3) . . . . ?
O2 C11 C12 C13 -53.7(4) . . . . ?
C10 C11 C12 C13 66.8(4) . . . . ?
O3 C12 C13 C14 -10.9(5) . . . . ?
C11 C12 C13 C14 111.4(4) . . . . ?
C12 C13 C14 C15 22.5(6) . . . . ?
C12 O3 C15 C14 18.9(5) . . . . ?
C13 C14 C15 O3 -26.1(6) . . . . ?
C9 C10 C11A O2A 85.3(6) . . . . ?
C9 C10 C11A C12A -153.7(5) . . . . ?
C15A O3A C12A C11A -153.7(8) . . . . ?
C15A O3A C12A C13A -27.8(9) . . . . ?
O2A C11A C12A O3A 62.8(9) . . . . ?
C10 C11A C12A O3A -54.7(8) . . . . ?
O2A C11A C12A C13A -56.8(10) . . . . ?
C10 C11A C12A C13A -174.3(8) . . . . ?
O3A C12A C13A C14A 15.6(13) . . . . ?
C11A C12A C13A C14A 139.3(12) . . . . ?
C12A C13A C14A C15A 1.5(17) . . . . ?
C12A O3A C15A C14A 29.5(13) . . . . ?
C13A C14A C15A O3A -18.5(17) . . . . ?

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
O2 H2 O3 0.841(10) 1.98(2) 2.796(4) 163(6) 3_676 yes
C1 H1C Cg3 0.98 2.72 3.507(4) 138 2_646 y
C4 H4 Cg3 0.95 2.70 3.484(4) 140 2_556 y
_iucr_geom_hbonds_special_details 
;
Cg3 is the centroid of the C2...C7 benzene ring.
;


_refine_diff_density_max         0.873
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.064

