# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_c36
_database_code_depnum_ccdc_archive 'CCDC 1989586'
_audit_update_record             
;
2020-03-11 deposited with the CCDC.	2022-09-17 downloaded from the CCDC.
;
_audit_creation_date             2018-07-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H34 O3'
_chemical_formula_sum            'C30 H34 O3'
_chemical_formula_weight         442.57
_chemical_absolute_configuration unk
_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 0.0033 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'

_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                   7.2131(4)
_cell_length_b                   14.0281(7)
_cell_length_c                   11.7885(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.280(5)
_cell_angle_gamma                90
_cell_volume                     1190.88(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3425
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.3330
_cell_measurement_theta_min      3.1560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01956
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7053
_diffrn_reflns_point_group_measured_fraction_full 0.864
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.259
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  11.00   1.00    1.50    --  -11.59 -57.00  60.00   87
  2  ω    -40.00  62.00   1.00    1.50    --  -11.59  57.00-150.00  102
  3  ω    -14.00  76.00   1.00    1.50    --   11.74  77.00 -30.00   90
;
_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      0.0450021000
_diffrn_orient_matrix_UB_12      0.0223017000
_diffrn_orient_matrix_UB_13      0.0480347000
_diffrn_orient_matrix_UB_21      0.0740299000
_diffrn_orient_matrix_UB_22      0.0138071000
_diffrn_orient_matrix_UB_23      -0.0335836000
_diffrn_orient_matrix_UB_31      -0.0467573000
_diffrn_orient_matrix_UB_32      0.0432606000
_diffrn_orient_matrix_UB_33      -0.0139913000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    0.717
_reflns_Friedel_fraction_max     0.717
_reflns_number_gt                3129
_reflns_number_total             3627
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1014 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3627
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0965
_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
2.a Ternary CH refined with riding coordinates:
 C18(H18), C14(H14), C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C3(H3A,H3B), C11(H11A,H11B), C16(H16A,H16B), C15(H15A,H15B),
 C7(H7A,H7B), C8(H8A,H8B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C28(H28), C6(H6), C21(H21), C27(H27), C26(H26), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C00Q(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O3 O 0.8785(3) 0.62622(16) 0.0268(2) 0.0208(6) Uani 1 1 d . . . . .
O1 O 0.7519(4) 0.09289(19) 0.7014(2) 0.0328(7) Uani 1 1 d . . . . .
O2 O 0.4482(4) 0.62529(18) -0.0564(2) 0.0302(7) Uani 1 1 d . . . . .
C13 C 0.6739(5) 0.4720(2) 0.1482(3) 0.0155(8) Uani 1 1 d . . . . .
C18 C 0.6002(5) 0.5754(2) 0.1201(3) 0.0166(8) Uani 1 1 d . . . . .
H18 H 0.537722 0.596189 0.187471 0.020 Uiso 1 1 calc R . . . .
C19 C 0.7428(5) 0.6491(2) 0.1013(3) 0.0175(8) Uani 1 1 d . . . . .
C17 C 0.4494(5) 0.5710(2) 0.0246(3) 0.0187(8) Uani 1 1 d . . . . .
C12 C 0.8194(5) 0.4784(2) 0.2469(3) 0.0189(8) Uani 1 1 d . . . . .
H12A H 0.925417 0.514176 0.222922 0.023 Uiso 1 1 calc R . . . .
H12B H 0.767613 0.512853 0.309038 0.023 Uiso 1 1 calc R . . . .
C22 C 0.7759(5) 0.7380(2) 0.1439(3) 0.0168(8) Uani 1 1 d . . . . .
C20 C 0.9959(5) 0.7023(2) 0.0250(3) 0.0209(9) Uani 1 1 d . . . . .
H20 H 1.099477 0.705920 -0.018319 0.025 Uiso 1 1 calc R . . . .
C14 C 0.5072(5) 0.4126(2) 0.1862(3) 0.0140(8) Uani 1 1 d . . . . .
H14 H 0.451655 0.448236 0.247152 0.017 Uiso 1 1 calc R . . . .
C28 C 0.4710(5) 0.7936(2) 0.2127(3) 0.0210(9) Uani 1 1 d . . . . .
H28 H 0.408885 0.756012 0.157831 0.025 Uiso 1 1 calc R . . . .
C9 C 0.5642(5) 0.3139(2) 0.2352(3) 0.0169(8) Uani 1 1 d . . . . .
H9 H 0.608164 0.274731 0.173331 0.020 Uiso 1 1 calc R . . . .
C4 C 0.7827(5) 0.2229(2) 0.3813(3) 0.0173(8) Uani 1 1 d . . . . .
C23 C 0.6643(5) 0.7932(2) 0.2217(3) 0.0196(9) Uani 1 1 d . . . . .
C1 C 0.7638(5) 0.1266(3) 0.6064(3) 0.0227(9) Uani 1 1 d . . . . .
C3 C 0.9242(5) 0.2411(2) 0.4814(3) 0.0219(9) Uani 1 1 d . . . . .
H3A H 1.043661 0.255594 0.451787 0.026 Uiso 1 1 calc R . . . .
H3B H 0.885116 0.296560 0.523024 0.026 Uiso 1 1 calc R . . . .
C11 C 0.8841(5) 0.3811(2) 0.2887(3) 0.0197(8) Uani 1 1 d . . . . .
H11A H 0.976112 0.388719 0.351312 0.024 Uiso 1 1 calc R . . . .
H11B H 0.942141 0.347733 0.227985 0.024 Uiso 1 1 calc R . . . .
C16 C 0.2964(5) 0.5013(3) 0.0407(3) 0.0212(9) Uani 1 1 d . . . . .
H16A H 0.229470 0.491113 -0.031986 0.025 Uiso 1 1 calc R . . . .
H16B H 0.210253 0.529271 0.091497 0.025 Uiso 1 1 calc R . . . .
C5 C 0.6110(5) 0.1740(2) 0.4222(3) 0.0177(8) Uani 1 1 d . . . . .
C15 C 0.3590(5) 0.4040(3) 0.0889(3) 0.0194(8) Uani 1 1 d . . . . .
H15A H 0.252221 0.370682 0.115920 0.023 Uiso 1 1 calc R . . . .
H15B H 0.407839 0.366112 0.028532 0.023 Uiso 1 1 calc R . . . .
C6 C 0.6039(5) 0.1360(2) 0.5263(3) 0.0220(9) Uani 1 1 d . . . . .
H6 H 0.489618 0.114429 0.548650 0.026 Uiso 1 1 calc R . . . .
C29 C 0.8707(5) 0.1576(3) 0.2934(3) 0.0231(9) Uani 1 1 d . . . . .
H29A H 0.981717 0.186858 0.268504 0.035 Uiso 1 1 calc GR . . . .
H29B H 0.784229 0.148432 0.229346 0.035 Uiso 1 1 calc GR . . . .
H29C H 0.900901 0.097098 0.327630 0.035 Uiso 1 1 calc GR . . . .
C7 C 0.4473(5) 0.1684(2) 0.3382(3) 0.0207(9) Uani 1 1 d . . . . .
H7A H 0.341102 0.144668 0.376493 0.025 Uiso 1 1 calc R . . . .
H7B H 0.474398 0.123020 0.279315 0.025 Uiso 1 1 calc R . . . .
C21 C 0.9412(5) 0.7712(3) 0.0944(3) 0.0209(9) Uani 1 1 d . . . . .
H21 H 0.999382 0.829631 0.107938 0.025 Uiso 1 1 calc R . . . .
C00Q C 0.7575(5) 0.4278(2) 0.0435(3) 0.0208(9) Uani 1 1 d . . . . .
H00A H 0.682907 0.444843 -0.023459 0.031 Uiso 1 1 calc GR . . . .
H00B H 0.760307 0.359705 0.051256 0.031 Uiso 1 1 calc GR . . . .
H00C H 0.881555 0.451258 0.037354 0.031 Uiso 1 1 calc GR . . . .
C8 C 0.3965(5) 0.2644(2) 0.2827(3) 0.0211(9) Uani 1 1 d . . . . .
H8A H 0.343711 0.305561 0.338566 0.025 Uiso 1 1 calc R . . . .
H8B H 0.302691 0.254217 0.221666 0.025 Uiso 1 1 calc R . . . .
C10 C 0.7211(5) 0.3215(2) 0.3282(3) 0.0169(8) Uani 1 1 d . . . . .
H10 H 0.669590 0.357841 0.390055 0.020 Uiso 1 1 calc R . . . .
C27 C 0.3703(6) 0.8487(3) 0.2837(3) 0.0272(10) Uani 1 1 d . . . . .
H27 H 0.241309 0.847951 0.275965 0.033 Uiso 1 1 calc R . . . .
C2 C 0.9475(5) 0.1572(3) 0.5636(3) 0.0223(9) Uani 1 1 d . . . . .
H2A H 1.003100 0.104086 0.525329 0.027 Uiso 1 1 calc R . . . .
H2B H 1.030690 0.175391 0.627475 0.027 Uiso 1 1 calc R . . . .
C26 C 0.4589(6) 0.9051(3) 0.3663(3) 0.0316(11) Uani 1 1 d . . . . .
H26 H 0.389956 0.942417 0.413681 0.038 Uiso 1 1 calc R . . . .
C24 C 0.7511(6) 0.8510(3) 0.3055(4) 0.0277(10) Uani 1 1 d . . . . .
H24 H 0.880142 0.852752 0.312721 0.033 Uiso 1 1 calc R . . . .
C25 C 0.6511(6) 0.9056(3) 0.3780(4) 0.0322(10) Uani 1 1 d . . . . .
H25 H 0.712238 0.942369 0.434081 0.039 Uiso 1 1 calc R . . . .


_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
O3 C19 1.389(4) . ?
O3 C20 1.364(4) . ?
O1 C1 1.224(4) . ?
O2 C17 1.221(4) . ?
C13 C18 1.573(5) . ?
C13 C12 1.524(5) . ?
C13 C14 1.551(5) . ?
C13 C00Q 1.535(4) . ?
C18 C19 1.483(5) . ?
C18 C17 1.522(5) . ?
C19 C22 1.361(5) . ?
C17 C16 1.495(5) . ?
C12 C11 1.516(5) . ?
C22 C23 1.475(5) . ?
C22 C21 1.435(5) . ?
C20 C21 1.340(5) . ?
C14 C9 1.547(5) . ?
C14 C15 1.527(5) . ?
C28 C23 1.392(5) . ?
C28 C27 1.376(5) . ?
C9 C8 1.529(5) . ?
C9 C10 1.534(5) . ?
C4 C3 1.537(5) . ?
C4 C5 1.518(5) . ?
C4 C29 1.546(5) . ?
C4 C10 1.572(5) . ?
C23 C24 1.398(5) . ?
C1 C6 1.454(5) . ?
C1 C2 1.507(5) . ?
C3 C2 1.526(5) . ?
C11 C10 1.536(4) . ?
C16 C15 1.536(5) . ?
C5 C6 1.342(5) . ?
C5 C7 1.499(5) . ?
C7 C8 1.532(5) . ?
C27 C26 1.383(6) . ?
C26 C25 1.386(6) . ?
C24 C25 1.380(5) . ?

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
C20 O3 C19 106.9(3) . . ?
C12 C13 C18 108.4(3) . . ?
C12 C13 C14 108.8(3) . . ?
C12 C13 C00Q 110.6(3) . . ?
C14 C13 C18 107.4(3) . . ?
C00Q C13 C18 110.3(3) . . ?
C00Q C13 C14 111.2(3) . . ?
C19 C18 C13 116.4(3) . . ?
C19 C18 C17 113.0(3) . . ?
C17 C18 C13 109.7(3) . . ?
O3 C19 C18 116.9(3) . . ?
C22 C19 O3 109.3(3) . . ?
C22 C19 C18 133.8(3) . . ?
O2 C17 C18 121.7(3) . . ?
O2 C17 C16 122.4(4) . . ?
C16 C17 C18 115.8(3) . . ?
C11 C12 C13 112.4(3) . . ?
C19 C22 C23 128.4(3) . . ?
C19 C22 C21 106.3(3) . . ?
C21 C22 C23 125.3(3) . . ?
C21 C20 O3 110.5(3) . . ?
C9 C14 C13 113.3(3) . . ?
C15 C14 C13 110.3(3) . . ?
C15 C14 C9 111.7(3) . . ?
C27 C28 C23 121.1(4) . . ?
C8 C9 C14 110.2(3) . . ?
C8 C9 C10 109.7(3) . . ?
C10 C9 C14 112.0(3) . . ?
C3 C4 C29 109.5(3) . . ?
C3 C4 C10 108.6(3) . . ?
C5 C4 C3 110.4(3) . . ?
C5 C4 C29 108.6(3) . . ?
C5 C4 C10 107.9(3) . . ?
C29 C4 C10 111.8(3) . . ?
C28 C23 C22 122.3(3) . . ?
C28 C23 C24 117.2(3) . . ?
C24 C23 C22 120.4(3) . . ?
O1 C1 C6 122.3(3) . . ?
O1 C1 C2 121.7(4) . . ?
C6 C1 C2 115.9(3) . . ?
C2 C3 C4 113.8(3) . . ?
C12 C11 C10 111.2(3) . . ?
C17 C16 C15 115.1(3) . . ?
C6 C5 C4 123.0(4) . . ?
C6 C5 C7 120.9(3) . . ?
C7 C5 C4 116.1(3) . . ?
C14 C15 C16 112.7(3) . . ?
C5 C6 C1 124.0(3) . . ?
C5 C7 C8 113.3(3) . . ?
C20 C21 C22 107.1(3) . . ?
C7 C8 C9 112.4(3) . . ?
C9 C10 C4 113.8(3) . . ?
C9 C10 C11 111.5(3) . . ?
C11 C10 C4 113.3(3) . . ?
C28 C27 C26 120.7(4) . . ?
C1 C2 C3 111.4(3) . . ?
C27 C26 C25 119.5(4) . . ?
C25 C24 C23 122.0(4) . . ?
C24 C25 C26 119.4(4) . . ?

_olex2_date_sample_data_collection 2018-07-11
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 16.092
_oxdiff_exptl_absorpt_empirical_full_min 0.645
