# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_hsw41-1
_database_code_depnum_ccdc_archive 'CCDC 1843946'
loop_
_audit_author_name
_audit_author_address
'Junseong Lee'
;Chonnam National University
South Korea
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'((S)-3-(2,6-diethylbenzyl)-1-(5-(trifluoromethyl)pyridin-2-yl)-3,4-dihydroisoquinoline) palladium(II) chloride'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H25 Cl2 F3 N2 Pd, C1 H2 Cl2'
_chemical_formula_sum            'C27 H27 Cl4 F3 N2 Pd'
_chemical_formula_weight         684.71

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.3222(2)
_cell_length_b                   16.3645(5)
_cell_length_c                   22.9119(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2745.40(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5617
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      19.77

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37246
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.170
_diffrn_reflns_theta_max         25.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5004
_reflns_number_gt                3907
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.996

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0560P)²] 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_abs_structure_details 
;
 Flack x determined using 1385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5004
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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
Pd1 Pd 0.32690(8) 0.79375(3) 0.99528(2) 0.02602(18) Uani 1 1 d . . . . .
Cl2 Cl 0.3440(3) 0.93260(10) 1.00137(9) 0.0362(4) Uani 1 1 d . . . . .
N1 N 0.3106(8) 0.6715(4) 0.9829(2) 0.0246(14) Uani 1 1 d . . . . .
N2 N 0.3339(8) 0.7896(4) 0.9073(2) 0.0190(12) Uani 1 1 d . . . . .
Cl1 Cl 0.3181(3) 0.78475(13) 1.09485(7) 0.0362(5) Uani 1 1 d . . . . .
C12 C 0.1508(11) 0.6501(4) 0.7981(3) 0.0284(18) Uani 1 1 d . . . . .
H12 H 0.0873 0.6152 0.8229 0.034 Uiso 1 1 calc R U . . .
C15 C 0.3334(11) 0.7576(4) 0.7248(3) 0.0292(18) Uani 1 1 d . . . . .
H15 H 0.3947 0.7932 0.7000 0.035 Uiso 1 1 calc R U . . .
C14 C 0.2178(10) 0.6985(5) 0.7011(3) 0.0286(18) Uani 1 1 d . . . . .
H14 H 0.2023 0.6948 0.6609 0.034 Uiso 1 1 calc R U . . .
C7 C 0.3011(10) 0.7184(4) 0.8844(3) 0.0242(17) Uani 1 1 d . . . . .
C8 C 0.2718(9) 0.7078(5) 0.8212(3) 0.0245(17) Uani 1 1 d . . . . .
C9 C 0.3586(9) 0.7641(4) 0.7843(3) 0.0239(18) Uani 1 1 d . . . . .
C13 C 0.1257(11) 0.6450(5) 0.7382(3) 0.032(2) Uani 1 1 d . . . . .
H13 H 0.0472 0.6059 0.7228 0.039 Uiso 1 1 calc R U . . .
C1 C 0.2992(10) 0.6493(4) 0.9257(3) 0.0237(17) Uani 1 1 d . . . . .
C11 C 0.3684(10) 0.8591(4) 0.8675(3) 0.0277(19) Uani 1 1 d . . . . .
H11 H 0.4496 0.8973 0.8878 0.033 Uiso 1 1 calc R U . . .
C10 C 0.4676(10) 0.8294(4) 0.8135(3) 0.0263(18) Uani 1 1 d . . . . .
H10A H 0.4859 0.8746 0.7868 0.032 Uiso 1 1 calc R U . . .
H10B H 0.5865 0.8081 0.8244 0.032 Uiso 1 1 calc R U . . .
C17 C 0.1937(12) 0.9545(5) 0.7989(3) 0.0275(18) Uani 1 1 d . . . . .
C16 C 0.1851(11) 0.9049(4) 0.8552(3) 0.0271(17) Uani 1 1 d . . . . .
H16A H 0.0868 0.8654 0.8524 0.033 Uiso 1 1 calc R U . . .
H16B H 0.1582 0.9411 0.8876 0.033 Uiso 1 1 calc R U . . .
C22 C 0.3091(12) 1.0212(5) 0.7937(3) 0.0324(19) Uani 1 1 d . . . . .
C21 C 0.3365(13) 1.0566(5) 0.7383(4) 0.041(2) Uani 1 1 d . . . . .
H21 H 0.4178 1.1000 0.7345 0.049 Uiso 1 1 calc R U . . .
C19 C 0.1197(12) 0.9681(5) 0.6968(4) 0.040(2) Uani 1 1 d . . . . .
H19 H 0.0529 0.9514 0.6644 0.048 Uiso 1 1 calc R U . . .
C18 C 0.0866(10) 0.9303(5) 0.7504(4) 0.032(2) Uani 1 1 d . . . . .
C20 C 0.2457(12) 1.0284(6) 0.6900(4) 0.046(3) Uani 1 1 d . . . . .
H20 H 0.2698 1.0502 0.6533 0.055 Uiso 1 1 calc R U . . .
C4 C 0.3191(10) 0.5324(4) 1.0098(3) 0.0279(16) Uani 1 1 d . . . . .
C3 C 0.3166(12) 0.5087(5) 0.9523(3) 0.0338(19) Uani 1 1 d . . . . .
H3 H 0.3220 0.4537 0.9422 0.041 Uiso 1 1 calc R U . . .
C2 C 0.3059(12) 0.5682(5) 0.9095(3) 0.0344(19) Uani 1 1 d . . . . .
H2 H 0.3033 0.5537 0.8703 0.041 Uiso 1 1 calc R U . . .
C5 C 0.3170(10) 0.6143(4) 1.0230(3) 0.0263(17) Uani 1 1 d . . . . .
H5 H 0.3202 0.6298 1.0620 0.032 Uiso 1 1 calc R U . . .
C26 C 0.3290(13) 1.1436(5) 0.8602(3) 0.044(2) Uani 1 1 d . . . . .
H26A H 0.3424 1.1797 0.8275 0.067 Uiso 1 1 calc R U . . .
H26B H 0.3943 1.1654 0.8931 0.067 Uiso 1 1 calc R U . . .
H26C H 0.2019 1.1385 0.8699 0.067 Uiso 1 1 calc R U . . .
C24 C -0.1892(14) 0.8542(6) 0.7057(3) 0.058(3) Uani 1 1 d . . . . .
H24A H -0.2479 0.9048 0.6960 0.086 Uiso 1 1 calc R U . . .
H24B H -0.2799 0.8141 0.7154 0.086 Uiso 1 1 calc R U . . .
H24C H -0.1192 0.8355 0.6728 0.086 Uiso 1 1 calc R U . . .
C23 C -0.0635(10) 0.8670(5) 0.7574(4) 0.038(2) Uani 1 1 d . . . . .
H23A H -0.0067 0.8150 0.7667 0.046 Uiso 1 1 calc R U . . .
H23B H -0.1378 0.8825 0.7907 0.046 Uiso 1 1 calc R U . . .
C25 C 0.4059(12) 1.0596(5) 0.8446(4) 0.048(2) Uani 1 1 d . . . . .
H25A H 0.5346 1.0650 0.8354 0.058 Uiso 1 1 calc R U . . .
H25B H 0.3953 1.0239 0.8783 0.058 Uiso 1 1 calc R U . . .
C6 C 0.3295(14) 0.4686(5) 1.0566(3) 0.038(2) Uani 1 1 d . . . . .
F1 F 0.1982(7) 0.4126(3) 1.05086(19) 0.0486(13) Uani 1 1 d . . . . .
F3 F 0.3135(7) 0.5001(3) 1.11006(18) 0.0450(12) Uani 1 1 d . . . . .
F2 F 0.4891(7) 0.4283(3) 1.0561(2) 0.0558(15) Uani 1 1 d . . . . .
Cl3 Cl 0.9885(5) 0.3051(2) 0.94367(12) 0.0877(10) Uani 1 1 d . . . . .
Cl4 Cl 0.5997(5) 0.32634(19) 0.92555(12) 0.0865(11) Uani 1 1 d . . . . .
C27 C 0.7916(18) 0.3507(7) 0.9688(5) 0.093(4) Uani 1 1 d . . . . .
H27A H 0.8081 0.4095 0.9691 0.112 Uiso 1 1 calc R U . . .
H27B H 0.7693 0.3333 1.0086 0.112 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
Pd1 N2 2.017(5) . ?
Pd1 N1 2.024(6) . ?
Pd1 Cl2 2.2800(18) . ?
Pd1 Cl1 2.2870(17) . ?
N1 C5 1.313(9) . ?
N1 C1 1.361(8) . ?
N2 C7 1.301(9) . ?
N2 C11 1.479(9) . ?
C12 C13 1.387(10) . ?
C12 C8 1.398(10) . ?
C15 C9 1.381(9) . ?
C15 C14 1.395(10) . ?
C14 C13 1.394(10) . ?
C7 C1 1.474(9) . ?
C7 C8 1.475(9) . ?
C8 C9 1.403(10) . ?
C9 C10 1.492(10) . ?
C1 C2 1.379(10) . ?
C11 C10 1.515(10) . ?
C11 C16 1.562(10) . ?
C17 C22 1.385(11) . ?
C17 C18 1.418(11) . ?
C17 C16 1.524(9) . ?
C22 C21 1.410(10) . ?
C22 C25 1.503(11) . ?
C21 C20 1.371(12) . ?
C19 C20 1.360(12) . ?
C19 C18 1.398(11) . ?
C18 C23 1.518(11) . ?
C4 C5 1.373(10) . ?
C4 C3 1.375(10) . ?
C4 C6 1.498(10) . ?
C3 C2 1.384(10) . ?
C26 C25 1.527(11) . ?
C24 C23 1.515(11) . ?
C6 F1 1.334(10) . ?
C6 F3 1.335(8) . ?
C6 F2 1.342(10) . ?
Cl3 C27 1.723(13) . ?
Cl4 C27 1.765(12) . ?

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
N2 Pd1 N1 80.1(2) . . ?
N2 Pd1 Cl2 95.34(17) . . ?
N1 Pd1 Cl2 175.41(18) . . ?
N2 Pd1 Cl1 174.39(16) . . ?
N1 Pd1 Cl1 94.30(16) . . ?
Cl2 Pd1 Cl1 90.27(8) . . ?
C5 N1 C1 119.0(6) . . ?
C5 N1 Pd1 127.2(5) . . ?
C1 N1 Pd1 113.7(5) . . ?
C7 N2 C11 118.2(5) . . ?
C7 N2 Pd1 115.3(5) . . ?
C11 N2 Pd1 126.5(4) . . ?
C13 C12 C8 119.9(7) . . ?
C9 C15 C14 121.2(7) . . ?
C13 C14 C15 119.4(7) . . ?
N2 C7 C1 115.5(6) . . ?
N2 C7 C8 121.9(6) . . ?
C1 C7 C8 122.6(6) . . ?
C12 C8 C9 120.2(6) . . ?
C12 C8 C7 122.9(7) . . ?
C9 C8 C7 116.6(6) . . ?
C15 C9 C8 118.9(7) . . ?
C15 C9 C10 124.7(7) . . ?
C8 C9 C10 116.3(6) . . ?
C12 C13 C14 120.1(7) . . ?
N1 C1 C2 120.9(6) . . ?
N1 C1 C7 114.4(6) . . ?
C2 C1 C7 124.4(6) . . ?
N2 C11 C10 109.8(6) . . ?
N2 C11 C16 109.5(6) . . ?
C10 C11 C16 114.7(6) . . ?
C9 C10 C11 109.8(6) . . ?
C22 C17 C18 119.4(7) . . ?
C22 C17 C16 121.2(7) . . ?
C18 C17 C16 119.4(7) . . ?
C17 C16 C11 111.9(6) . . ?
C17 C22 C21 119.3(8) . . ?
C17 C22 C25 123.3(7) . . ?
C21 C22 C25 117.4(8) . . ?
C20 C21 C22 121.3(8) . . ?
C20 C19 C18 122.7(9) . . ?
C19 C18 C17 118.0(7) . . ?
C19 C18 C23 121.4(8) . . ?
C17 C18 C23 120.6(7) . . ?
C19 C20 C21 118.8(9) . . ?
C5 C4 C3 119.1(7) . . ?
C5 C4 C6 121.6(6) . . ?
C3 C4 C6 119.3(7) . . ?
C4 C3 C2 118.8(7) . . ?
C1 C2 C3 119.2(7) . . ?
N1 C5 C4 122.9(7) . . ?
C24 C23 C18 116.8(8) . . ?
C22 C25 C26 112.6(7) . . ?
F1 C6 F3 107.0(7) . . ?
F1 C6 F2 106.8(6) . . ?
F3 C6 F2 105.9(7) . . ?
F1 C6 C4 111.8(7) . . ?
F3 C6 C4 112.5(7) . . ?
F2 C6 C4 112.4(7) . . ?
Cl3 C27 Cl4 112.4(5) . . ?

_refine_diff_density_max         0.689
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.090

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, Hexane'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Heat-sensitive
####################################################################### 
# 
# 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_hsw58-1
_database_code_depnum_ccdc_archive 'CCDC 1954885'
loop_
_audit_author_name
_audit_author_address
'Junseong Lee'
;Chonnam National University
South Korea
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(S)-2-(4-(tert-butyl)phenyl)-2-methylchroman-4-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 O2'
_chemical_formula_sum            'C20 H22 O2'
_chemical_formula_weight         294.37

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   23.2747(4)
_cell_length_b                   6.77810(10)
_cell_length_c                   10.2443(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.9349(17)
_cell_angle_gamma                90
_cell_volume                     1615.20(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.42

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12536
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.751
_diffrn_reflns_theta_max         25.424
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2965
_reflns_number_gt                2880
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.996

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0501P)²+0.4895P] 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_abs_structure_details 
;
 Flack x determined using 1292 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2965
_refine_ls_number_parameters     203
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0802
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.82315(7) 1.0358(2) 0.40751(14) 0.0409(4) Uani 1 1 d . . . . .
O2 O 0.84674(5) 0.77465(19) 0.05311(11) 0.0247(3) Uani 1 1 d . . . . .
C1 C 0.82765(8) 0.9618(3) 0.30018(18) 0.0271(4) Uani 1 1 d . . . . .
C2 C 0.80026(7) 0.7732(3) 0.26200(16) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.80983(7) 0.6927(3) 0.13882(16) 0.0214(4) Uani 1 1 d . . . . .
C4 C 0.88971(7) 0.9109(3) 0.10712(17) 0.0241(4) Uani 1 1 d . . . . .
C5 C 0.85963(8) 1.0606(3) 0.19274(19) 0.0281(4) Uani 1 1 d . . . . .
H5A H 0.8880 1.1503 0.2310 0.034 Uiso 1 1 calc R U . . .
H5B H 0.8328 1.1375 0.1390 0.034 Uiso 1 1 calc R U . . .
C6 C 0.76189(7) 0.6776(3) 0.34329(17) 0.0274(4) Uani 1 1 d . . . . .
H6 H 0.7557 0.7283 0.4260 0.033 Uiso 1 1 calc R U . . .
C7 C 0.73324(7) 0.5096(3) 0.30269(18) 0.0297(4) Uani 1 1 d . . . . .
H7 H 0.7080 0.4469 0.3576 0.036 Uiso 1 1 calc R U . . .
C8 C 0.74244(8) 0.4343(3) 0.17859(19) 0.0299(4) Uani 1 1 d . . . . .
H8 H 0.7228 0.3217 0.1505 0.036 Uiso 1 1 calc R U . . .
C9 C 0.78048(7) 0.5249(3) 0.09642(17) 0.0270(4) Uani 1 1 d . . . . .
H9 H 0.7863 0.4738 0.0136 0.032 Uiso 1 1 calc R U . . .
C10 C 0.91402(8) 1.0090(3) -0.01302(19) 0.0352(5) Uani 1 1 d . . . . .
H10A H 0.8837 1.0750 -0.0614 0.053 Uiso 1 1 calc R U . . .
H10B H 0.9309 0.9105 -0.0672 0.053 Uiso 1 1 calc R U . . .
H10C H 0.9429 1.1032 0.0139 0.053 Uiso 1 1 calc R U . . .
C11 C 0.93697(7) 0.7938(3) 0.17985(16) 0.0227(4) Uani 1 1 d . . . . .
C12 C 0.95035(8) 0.6038(3) 0.1407(2) 0.0335(5) Uani 1 1 d . . . . .
H12 H 0.9277 0.5427 0.0760 0.040 Uiso 1 1 calc R U . . .
C13 C 0.99698(8) 0.5037(3) 0.1968(2) 0.0344(4) Uani 1 1 d . . . . .
H13 H 1.0049 0.3766 0.1684 0.041 Uiso 1 1 calc R U . . .
C14 C 1.03217(7) 0.5875(3) 0.29412(16) 0.0228(4) Uani 1 1 d . . . . .
C15 C 1.01794(8) 0.7764(3) 0.33375(17) 0.0259(4) Uani 1 1 d . . . . .
H15 H 1.0402 0.8372 0.3992 0.031 Uiso 1 1 calc R U . . .
C16 C 0.97125(8) 0.8774(3) 0.27826(18) 0.0263(4) Uani 1 1 d . . . . .
H16 H 0.9629 1.0035 0.3078 0.032 Uiso 1 1 calc R U . . .
C17 C 1.08623(7) 0.4803(3) 0.34771(18) 0.0262(4) Uani 1 1 d . . . . .
C18 C 1.13274(9) 0.5026(4) 0.2458(3) 0.0473(6) Uani 1 1 d . . . . .
H18A H 1.1674 0.4385 0.2768 0.071 Uiso 1 1 calc R U . . .
H18B H 1.1403 0.6401 0.2318 0.071 Uiso 1 1 calc R U . . .
H18C H 1.1196 0.4432 0.1651 0.071 Uiso 1 1 calc R U . . .
C19 C 1.07472(9) 0.2601(3) 0.3667(2) 0.0373(5) Uani 1 1 d . . . . .
H19A H 1.0448 0.2433 0.4279 0.056 Uiso 1 1 calc R U . . .
H19B H 1.1091 0.1968 0.3997 0.056 Uiso 1 1 calc R U . . .
H19C H 1.0630 0.2021 0.2845 0.056 Uiso 1 1 calc R U . . .
C20 C 1.10830(10) 0.5654(4) 0.4771(2) 0.0509(7) Uani 1 1 d . . . . .
H20A H 1.1211 0.6984 0.4642 0.076 Uiso 1 1 calc R U . . .
H20B H 1.1398 0.4869 0.5107 0.076 Uiso 1 1 calc R U . . .
H20C H 1.0779 0.5647 0.5383 0.076 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 C1 1.216(2) . ?
O2 C3 1.367(2) . ?
O2 C4 1.457(2) . ?
C1 C2 1.475(3) . ?
C1 C5 1.506(3) . ?
C2 C3 1.400(2) . ?
C2 C6 1.401(3) . ?
C3 C9 1.389(3) . ?
C4 C10 1.524(2) . ?
C4 C5 1.526(3) . ?
C4 C11 1.530(2) . ?
C6 C7 1.377(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.386(3) . ?
C11 C16 1.386(2) . ?
C11 C12 1.387(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.387(3) . ?
C14 C17 1.538(2) . ?
C15 C16 1.389(3) . ?
C17 C20 1.519(3) . ?
C17 C19 1.530(3) . ?
C17 C18 1.537(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
C3 O2 C4 116.87(12) . . ?
O1 C1 C2 123.18(18) . . ?
O1 C1 C5 122.50(18) . . ?
C2 C1 C5 114.26(16) . . ?
C3 C2 C6 118.66(17) . . ?
C3 C2 C1 119.77(16) . . ?
C6 C2 C1 121.46(16) . . ?
O2 C3 C9 116.42(15) . . ?
O2 C3 C2 122.90(16) . . ?
C9 C3 C2 120.66(16) . . ?
O2 C4 C10 103.81(14) . . ?
O2 C4 C5 108.49(13) . . ?
C10 C4 C5 111.36(16) . . ?
O2 C4 C11 109.21(14) . . ?
C10 C4 C11 109.83(14) . . ?
C5 C4 C11 113.65(14) . . ?
C1 C5 C4 111.86(16) . . ?
C7 C6 C2 121.02(17) . . ?
C6 C7 C8 119.38(17) . . ?
C9 C8 C7 120.88(18) . . ?
C8 C9 C3 119.38(16) . . ?
C16 C11 C12 117.40(16) . . ?
C16 C11 C4 121.96(16) . . ?
C12 C11 C4 120.39(16) . . ?
C11 C12 C13 120.96(18) . . ?
C12 C13 C14 122.04(19) . . ?
C15 C14 C13 116.52(17) . . ?
C15 C14 C17 122.14(15) . . ?
C13 C14 C17 121.21(17) . . ?
C14 C15 C16 121.74(16) . . ?
C11 C16 C15 121.31(17) . . ?
C20 C17 C19 108.34(18) . . ?
C20 C17 C18 109.30(18) . . ?
C19 C17 C18 108.22(17) . . ?
C20 C17 C14 112.37(16) . . ?
C19 C17 C14 111.19(15) . . ?
C18 C17 C14 107.32(15) . . ?

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.045

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane'
_chemical_properties_physical    Heat-sensitive
