# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cd16744
_database_code_depnum_ccdc_archive 'CCDC 1522831'
_audit_update_record             
;
2016-12-15 deposited with the CCDC.
2017-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 O'
_chemical_formula_weight         264.35

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.8590(15)
_cell_length_b                   21.377(4)
_cell_length_c                   8.0979(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.440(4)
_cell_angle_gamma                90
_cell_volume                     1470.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1857
_cell_measurement_theta_min      5.159
_cell_measurement_theta_max      44.587

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6405
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8405
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         25.499
_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             2743
_reflns_number_gt                1949
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0680P)²+0.0373P] 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_number_reflns         2743
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 1.15941(13) 0.53557(7) 0.87528(17) 0.0890(5) Uani 1 1 d . . . . .
C1 C 0.15328(17) 0.63724(7) 0.34821(19) 0.0529(4) Uani 1 1 d . . . . .
C2 C -0.0044(2) 0.64732(8) 0.2534(2) 0.0662(5) Uani 1 1 d . . . . .
H2 H -0.0421 0.6290 0.1454 0.079 Uiso 1 1 calc R U . . .
C3 C -0.1024(2) 0.68266(9) 0.3144(3) 0.0732(5) Uani 1 1 d . . . . .
H3 H -0.2061 0.6885 0.2492 0.088 Uiso 1 1 calc R U . . .
C4 C -0.0473(2) 0.71054(8) 0.4761(3) 0.0710(5) Uani 1 1 d . . . . .
H4 H -0.1147 0.7353 0.5178 0.085 Uiso 1 1 calc R U . . .
C5 C 0.10336(18) 0.70193(7) 0.5734(2) 0.0609(5) Uani 1 1 d . . . . .
H5 H 0.1375 0.7210 0.6807 0.073 Uiso 1 1 calc R U . . .
C6 C 0.20921(17) 0.66462(6) 0.51517(19) 0.0489(4) Uani 1 1 d . . . . .
C7 C 0.36767(17) 0.65235(6) 0.60769(18) 0.0470(4) Uani 1 1 d . . . . .
C8 C 0.46264(17) 0.61596(6) 0.53807(18) 0.0471(4) Uani 1 1 d . . . . .
C9 C 0.40587(19) 0.59011(7) 0.37286(19) 0.0560(4) Uani 1 1 d . . . . .
H9 H 0.4712 0.5659 0.3266 0.067 Uiso 1 1 calc R U . . .
C10 C 0.25448(19) 0.60084(7) 0.2817(2) 0.0595(4) Uani 1 1 d . . . . .
H10 H 0.2166 0.5837 0.1723 0.071 Uiso 1 1 calc R U . . .
C11 C 0.61904(17) 0.61095(7) 0.65895(19) 0.0507(4) Uani 1 1 d . . . . .
C12 C 0.61795(18) 0.64347(7) 0.7993(2) 0.0563(4) Uani 1 1 d . . . . .
H12 H 0.7040 0.6476 0.8961 0.068 Uiso 1 1 calc R U . . .
C13 C 0.46372(18) 0.67170(7) 0.78092(19) 0.0525(4) Uani 1 1 d . . . . .
C14 C 0.4528(2) 0.73511(8) 0.8620(2) 0.0672(5) Uani 1 1 d . . . . .
H14A H 0.5502 0.7548 0.9270 0.081 Uiso 1 1 calc R U . . .
H14B H 0.3723 0.7639 0.7989 0.081 Uiso 1 1 calc R U . . .
C15 C 0.4014(2) 0.67916(9) 0.9353(2) 0.0711(5) Uani 1 1 d . . . . .
H15A H 0.2892 0.6736 0.9176 0.085 Uiso 1 1 calc R U . . .
H15B H 0.4670 0.6645 1.0457 0.085 Uiso 1 1 calc R U . . .
C16 C 0.75119(17) 0.57572(7) 0.6232(2) 0.0560(4) Uani 1 1 d . . . . .
H16A H 0.7762 0.5949 0.5257 0.067 Uiso 1 1 calc R U . . .
H16B H 0.7162 0.5333 0.5903 0.067 Uiso 1 1 calc R U . . .
C17 C 0.89947(17) 0.57276(8) 0.7717(2) 0.0592(4) Uani 1 1 d . . . . .
H17A H 0.9342 0.6150 0.8064 0.071 Uiso 1 1 calc R U . . .
H17B H 0.8759 0.5525 0.8686 0.071 Uiso 1 1 calc R U . . .
C18 C 1.03037(16) 0.53817(7) 0.7289(2) 0.0583(4) Uani 1 1 d . . . . .
H18A H 0.9963 0.4962 0.6906 0.070 Uiso 1 1 calc R U . . .
H18B H 1.0596 0.5594 0.6366 0.070 Uiso 1 1 calc R U . . .
C19 C 1.2905(2) 0.50606(11) 0.8474(3) 0.0947(7) Uani 1 1 d . . . . .
H19A H 1.2609 0.4655 0.7981 0.142 Uiso 1 1 calc R U . . .
H19B H 1.3707 0.5016 0.9550 0.142 Uiso 1 1 calc R U . . .
H19C H 1.3303 0.5308 0.7700 0.142 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 C19 1.395(2) . ?
O1 C18 1.3958(17) . ?
C1 C10 1.404(2) . ?
C1 C2 1.407(2) . ?
C1 C6 1.427(2) . ?
C2 C3 1.345(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.357(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.416(2) . ?
C7 C8 1.378(2) . ?
C7 C13 1.4790(19) . ?
C8 C9 1.403(2) . ?
C8 C11 1.457(2) . ?
C9 C10 1.355(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.335(2) . ?
C11 C16 1.488(2) . ?
C12 C13 1.462(2) . ?
C12 H12 0.9300 . ?
C13 C15 1.511(2) . ?
C13 C14 1.521(2) . ?
C14 C15 1.464(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.510(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.496(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C19 O1 C18 113.57(14) . . ?
C10 C1 C2 121.24(15) . . ?
C10 C1 C6 120.15(14) . . ?
C2 C1 C6 118.61(16) . . ?
C3 C2 C1 121.98(16) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 119.61(16) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.80(18) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.38(16) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 125.54(14) . . ?
C5 C6 C1 117.60(14) . . ?
C7 C6 C1 116.85(15) . . ?
C8 C7 C6 121.10(13) . . ?
C8 C7 C13 106.97(13) . . ?
C6 C7 C13 131.92(14) . . ?
C7 C8 C9 121.13(14) . . ?
C7 C8 C11 109.96(12) . . ?
C9 C8 C11 128.90(14) . . ?
C10 C9 C8 119.03(16) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C1 121.72(14) . . ?
C9 C10 H10 119.1 . . ?
C1 C10 H10 119.1 . . ?
C12 C11 C8 107.40(14) . . ?
C12 C11 C16 128.69(14) . . ?
C8 C11 C16 123.90(13) . . ?
C11 C12 C13 111.11(14) . . ?
C11 C12 H12 124.4 . . ?
C13 C12 H12 124.4 . . ?
C12 C13 C7 104.56(13) . . ?
C12 C13 C15 120.61(14) . . ?
C7 C13 C15 124.56(14) . . ?
C12 C13 C14 119.71(13) . . ?
C7 C13 C14 124.66(13) . . ?
C15 C13 C14 57.75(11) . . ?
C15 C14 C13 60.80(11) . . ?
C15 C14 H14A 117.7 . . ?
C13 C14 H14A 117.7 . . ?
C15 C14 H14B 117.7 . . ?
C13 C14 H14B 117.7 . . ?
H14A C14 H14B 114.8 . . ?
C14 C15 C13 61.45(11) . . ?
C14 C15 H15A 117.6 . . ?
C13 C15 H15A 117.6 . . ?
C14 C15 H15B 117.6 . . ?
C13 C15 H15B 117.6 . . ?
H15A C15 H15B 114.7 . . ?
C11 C16 C17 114.92(13) . . ?
C11 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
C11 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C16 113.14(13) . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
O1 C18 C17 108.98(13) . . ?
O1 C18 H18A 109.9 . . ?
C17 C18 H18A 109.9 . . ?
O1 C18 H18B 109.9 . . ?
C17 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
C10 C1 C2 C3 -179.20(16) . . . . ?
C6 C1 C2 C3 1.1(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 -179.32(15) . . . . ?
C4 C5 C6 C1 1.4(2) . . . . ?
C10 C1 C6 C5 178.49(14) . . . . ?
C2 C1 C6 C5 -1.8(2) . . . . ?
C10 C1 C6 C7 -0.9(2) . . . . ?
C2 C1 C6 C7 178.80(13) . . . . ?
C5 C6 C7 C8 -178.91(13) . . . . ?
C1 C6 C7 C8 0.4(2) . . . . ?
C5 C6 C7 C13 1.5(3) . . . . ?
C1 C6 C7 C13 -179.21(14) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C13 C7 C8 C9 -179.95(13) . . . . ?
C6 C7 C8 C11 179.83(12) . . . . ?
C13 C7 C8 C11 -0.46(16) . . . . ?
C7 C8 C9 C10 -0.6(2) . . . . ?
C11 C8 C9 C10 179.98(14) . . . . ?
C8 C9 C10 C1 0.1(2) . . . . ?
C2 C1 C10 C9 -179.04(15) . . . . ?
C6 C1 C10 C9 0.6(2) . . . . ?
C7 C8 C11 C12 0.33(17) . . . . ?
C9 C8 C11 C12 179.77(15) . . . . ?
C7 C8 C11 C16 -179.06(13) . . . . ?
C9 C8 C11 C16 0.4(2) . . . . ?
C8 C11 C12 C13 -0.06(18) . . . . ?
C16 C11 C12 C13 179.30(14) . . . . ?
C11 C12 C13 C7 -0.21(17) . . . . ?
C11 C12 C13 C15 146.35(15) . . . . ?
C11 C12 C13 C14 -145.76(15) . . . . ?
C8 C7 C13 C12 0.41(16) . . . . ?
C6 C7 C13 C12 -179.93(15) . . . . ?
C8 C7 C13 C15 -144.43(15) . . . . ?
C6 C7 C13 C15 35.2(2) . . . . ?
C8 C7 C13 C14 143.73(15) . . . . ?
C6 C7 C13 C14 -36.6(3) . . . . ?
C12 C13 C14 C15 -109.46(17) . . . . ?
C7 C13 C14 C15 112.28(18) . . . . ?
C12 C13 C15 C14 107.91(16) . . . . ?
C7 C13 C15 C14 -112.45(16) . . . . ?
C12 C11 C16 C17 5.0(2) . . . . ?
C8 C11 C16 C17 -175.70(13) . . . . ?
C11 C16 C17 C18 -178.70(13) . . . . ?
C19 O1 C18 C17 -177.83(15) . . . . ?
C16 C17 C18 O1 -177.47(13) . . . . ?

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4



