# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_kk3mc
_database_code_depnum_ccdc_archive 'CCDC 2045362'
loop_
_audit_author_name
_audit_author_address
'Charlene Tsay'
;University of California, Riverside
United States of America
;
_audit_update_record             
;
2020-11-19 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT420_kk3mc               
;
PROBLEM: D-H Without Acceptor       O1       --H1       .     Please Check 
RESPONSE: The phenolic hydrogen was located in the difference map in an
          orientation directed toward the pi-system of the neighboring
          aromatic ring, which is a known hydrogen bond acceptor.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 O'
_chemical_formula_weight         206.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_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+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   10.0087(2)
_cell_length_b                   10.0087(2)
_cell_length_c                   12.7456(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1276.78(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3715
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.56

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.073
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6138
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS 2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12704
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.035
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2616
_reflns_number_gt                2044
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_max     1.000
_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       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT 8.38a (Bruker, 2017)'
_computing_data_reduction        'SAINT 8.38a (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 The phenolic hydrogen, which is oriented toward the pi-system of
 the neighboring aromatic ring, was located in the Fourier
 synthesis and refined freely. 

 One ligand tert-butyl group exhibited disorder that was modeled
 over two positions; the disorder ratio was refined freely and
 converged at 87:13. This disorder was refined with the help of
 similarity restraints on 1,2- and 1,3- distances. The minor
 position of the disorder is in a roughly staggered orientation
 with respect to the major position, and the anisotropic
 displacement parameters of opposing carbon atoms were
 constrained to be equivalent.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_abs_structure_details 
; 
 Insufficient anomalous signal for this compound with
 molybdenum radiation.
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2616
_refine_ls_number_parameters     156
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.025
_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 0.5888(2) 0.4775(2) 0.65626(15) 0.0277(5) Uani 1 1 d . . . . .
H1 H 0.538(5) 0.544(5) 0.667(3) 0.076(15) Uiso 1 1 d . . . . .
C1 C 0.6760(3) 0.5171(3) 0.5794(2) 0.0189(6) Uani 1 1 d . . . . .
C2 C 0.7844(3) 0.4332(3) 0.5559(2) 0.0174(6) Uani 1 1 d . . . . .
C3 C 0.8683(3) 0.4796(3) 0.4770(2) 0.0183(6) Uani 1 1 d . . . . .
H3 H 0.943515 0.426709 0.458541 0.022 Uiso 1 1 calc R U . . .
C4 C 0.8486(3) 0.5984(3) 0.4238(2) 0.0204(6) Uani 1 1 d . . . . .
H4 H 0.910559 0.625101 0.371341 0.024 Uiso 1 1 calc R U . . .
C5 C 0.7390(3) 0.6792(3) 0.4460(2) 0.0188(6) Uani 1 1 d . . . . .
C6 C 0.6543(3) 0.6365(3) 0.5255(2) 0.0203(6) Uani 1 1 d . . . . .
H6 H 0.579375 0.690044 0.543624 0.024 Uiso 1 1 calc R U . . .
C7 C 0.8068(3) 0.2997(3) 0.6124(2) 0.0220(7) Uani 1 1 d . . . . .
C8 C 0.9327(3) 0.2296(3) 0.5720(3) 0.0316(8) Uani 1 1 d . . . . .
H8A H 0.923363 0.211908 0.496749 0.047 Uiso 1 1 calc R U . . .
H8B H 0.944777 0.144976 0.609532 0.047 Uiso 1 1 calc R U . . .
H8C H 1.010570 0.287009 0.583913 0.047 Uiso 1 1 calc R U . . .
C9 C 0.8234(3) 0.3220(3) 0.7304(2) 0.0311(8) Uani 1 1 d . . . . .
H9A H 0.896878 0.384762 0.742758 0.047 Uiso 1 1 calc R U . . .
H9B H 0.843545 0.236614 0.764604 0.047 Uiso 1 1 calc R U . . .
H9C H 0.740542 0.358729 0.759370 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6872(3) 0.2066(3) 0.5906(3) 0.0294(7) Uani 1 1 d . . . . .
H10A H 0.605865 0.245835 0.620311 0.044 Uiso 1 1 calc R U . . .
H10B H 0.703578 0.119314 0.622888 0.044 Uiso 1 1 calc R U . . .
H10C H 0.676218 0.195645 0.514672 0.044 Uiso 1 1 calc R U . . .
C11 C 0.7132(3) 0.8071(3) 0.3834(2) 0.0252(7) Uani 1 1 d D . . . .
C12 C 0.6957(5) 0.7750(4) 0.2690(3) 0.0413(11) Uani 0.867(4) 1 d D . P A 1
H12A H 0.774692 0.727111 0.243384 0.062 Uiso 0.867(4) 1 calc R U P A 1
H12B H 0.684700 0.858039 0.229215 0.062 Uiso 0.867(4) 1 calc R U P A 1
H12C H 0.616382 0.718807 0.259762 0.062 Uiso 0.867(4) 1 calc R U P A 1
C13 C 0.5906(4) 0.8842(4) 0.4234(3) 0.0351(10) Uani 0.867(4) 1 d D . P A 1
H13A H 0.580529 0.966972 0.383121 0.053 Uiso 0.867(4) 1 calc R U P A 1
H13B H 0.602679 0.905704 0.497785 0.053 Uiso 0.867(4) 1 calc R U P A 1
H13C H 0.510498 0.828986 0.414743 0.053 Uiso 0.867(4) 1 calc R U P A 1
C14 C 0.8344(4) 0.9021(4) 0.3975(3) 0.0408(10) Uani 0.867(4) 1 d D . P A 1
H14A H 0.915879 0.857266 0.373411 0.061 Uiso 0.867(4) 1 calc R U P A 1
H14B H 0.843733 0.925527 0.471810 0.061 Uiso 0.867(4) 1 calc R U P A 1
H14C H 0.820168 0.983474 0.356259 0.061 Uiso 0.867(4) 1 calc R U P A 1
C12A C 0.696(3) 0.919(2) 0.4526(17) 0.0413(11) Uani 0.133(4) 1 d D . P A 2
H12D H 0.679877 0.999690 0.411307 0.062 Uiso 0.133(4) 1 calc R U P A 2
H12E H 0.620000 0.902308 0.499094 0.062 Uiso 0.133(4) 1 calc R U P A 2
H12F H 0.777282 0.930563 0.494782 0.062 Uiso 0.133(4) 1 calc R U P A 2
C13A C 0.819(2) 0.828(2) 0.2955(18) 0.0351(10) Uani 0.133(4) 1 d D . P A 2
H13D H 0.823778 0.746883 0.252144 0.053 Uiso 0.133(4) 1 calc R U P A 2
H13E H 0.792714 0.903730 0.251714 0.053 Uiso 0.133(4) 1 calc R U P A 2
H13F H 0.906159 0.845033 0.327242 0.053 Uiso 0.133(4) 1 calc R U P A 2
C14A C 0.578(2) 0.775(2) 0.320(2) 0.0408(10) Uani 0.133(4) 1 d D . P A 2
H14D H 0.592551 0.698199 0.273142 0.061 Uiso 0.133(4) 1 calc R U P A 2
H14E H 0.505989 0.753686 0.369299 0.061 Uiso 0.133(4) 1 calc R U P A 2
H14F H 0.552219 0.852813 0.277713 0.061 Uiso 0.133(4) 1 calc R U P A 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 C1 1.371(3) . ?
O1 H1 0.85(5) . ?
C1 C6 1.396(4) . ?
C1 C2 1.404(4) . ?
C2 C3 1.390(4) . ?
C2 C7 1.534(4) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(4) . ?
C5 C11 1.530(4) . ?
C6 H6 0.9500 . ?
C7 C9 1.529(4) . ?
C7 C8 1.532(4) . ?
C7 C10 1.542(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12A 1.434(18) . ?
C11 C12 1.503(5) . ?
C11 C13 1.537(5) . ?
C11 C14 1.552(5) . ?
C11 C13A 1.552(18) . ?
C11 C14A 1.614(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?

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 H1 106(3) . . ?
O1 C1 C6 120.0(2) . . ?
O1 C1 C2 118.1(2) . . ?
C6 C1 C2 121.9(2) . . ?
C3 C2 C1 114.9(2) . . ?
C3 C2 C7 122.9(2) . . ?
C1 C2 C7 122.3(2) . . ?
C4 C3 C2 123.8(3) . . ?
C4 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 116.8(3) . . ?
C6 C5 C11 122.4(2) . . ?
C4 C5 C11 120.8(3) . . ?
C5 C6 C1 121.8(3) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C9 C7 C8 107.9(3) . . ?
C9 C7 C2 110.5(2) . . ?
C8 C7 C2 111.2(2) . . ?
C9 C7 C10 110.5(3) . . ?
C8 C7 C10 107.5(2) . . ?
C2 C7 C10 109.1(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12A C11 C5 110.5(10) . . ?
C12 C11 C5 110.3(2) . . ?
C12 C11 C13 109.6(3) . . ?
C5 C11 C13 112.4(2) . . ?
C12 C11 C14 109.6(3) . . ?
C5 C11 C14 108.7(3) . . ?
C13 C11 C14 106.1(3) . . ?
C12A C11 C13A 114.9(15) . . ?
C5 C11 C13A 111.9(8) . . ?
C12A C11 C14A 111.5(14) . . ?
C5 C11 C14A 103.7(9) . . ?
C13A C11 C14A 103.6(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C12A H12D 109.5 . . ?
C11 C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
C11 C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C11 C13A H13D 109.5 . . ?
C11 C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
C11 C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
C11 C14A H14D 109.5 . . ?
C11 C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
C11 C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?

_refine_diff_density_max         0.142
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035

