# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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#######################################################################

data_cu_kwon1503s_a
_database_code_depnum_ccdc_archive 'CCDC 1489646'
_audit_update_record             
;
2016-07-01 deposited with the CCDC.
2018-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H15 O P'
_chemical_formula_sum            'C12 H15 O P'
_chemical_formula_weight         206.21

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'
P P 0.2955 0.4335 '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                   8.6681(6)
_cell_length_b                   10.3977(7)
_cell_length_c                   11.4123(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1028.57(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9531
_cell_measurement_theta_min      3.87
_cell_measurement_theta_max      72.13

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .2
_exptl_absorpt_coefficient_mu    2.050
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS micro--focus source'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            9605
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.756
_diffrn_reflns_theta_max         72.126
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             1950
_reflns_number_gt                1939
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_max     0.938
_reflns_Friedel_fraction_full    0.964

_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-2014/6 (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)+(0.0331P)²+0.1696P] 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 787 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.032(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         1950
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0612
_refine_ls_wR_factor_gt          0.0609
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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
P1 P 0.19864(5) 0.73343(4) 0.63559(3) 0.01211(14) Uani 1 1 d . . . . .
O1 O 0.03490(14) 0.74523(13) 0.67535(11) 0.0183(3) Uani 1 1 d . . . . .
C1 C 0.3460(2) 0.77732(18) 0.74278(16) 0.0163(4) Uani 1 1 d . . . . .
H1 H 0.3742 0.7082 0.7999 0.020 Uiso 1 1 calc R U . . .
C2 C 0.2932(2) 0.90554(18) 0.79784(16) 0.0201(4) Uani 1 1 d . . . . .
H2A H 0.3572 0.9275 0.8668 0.024 Uiso 1 1 calc R U . . .
H2B H 0.1837 0.9009 0.8222 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3154(3) 1.00591(17) 0.69813(18) 0.0218(4) Uani 1 1 d . . . . .
H3A H 0.2152 1.0432 0.6741 0.026 Uiso 1 1 calc R U . . .
H3B H 0.3847 1.0763 0.7236 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3887(2) 0.92819(18) 0.59659(18) 0.0200(4) Uani 1 1 d . . . . .
H4 H 0.4557 0.9818 0.5446 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2639(2) 0.85308(18) 0.52859(17) 0.0177(4) Uani 1 1 d . . . . .
H5A H 0.3079 0.8112 0.4582 0.021 Uiso 1 1 calc R U . . .
H5B H 0.1783 0.9103 0.5045 0.021 Uiso 1 1 calc R U . . .
C6 C 0.4785(2) 0.82323(19) 0.66221(17) 0.0193(4) Uani 1 1 d . . . . .
H6A H 0.5664 0.8587 0.7072 0.023 Uiso 1 1 calc R U . . .
H6B H 0.5151 0.7544 0.6092 0.023 Uiso 1 1 calc R U . . .
C7 C 0.2404(2) 0.57121(17) 0.58684(16) 0.0138(4) Uani 1 1 d . . . . .
C8 C 0.3391(2) 0.54053(19) 0.49456(16) 0.0163(4) Uani 1 1 d . . . . .
H8 H 0.3864 0.6070 0.4502 0.020 Uiso 1 1 calc R U . . .
C9 C 0.3682(2) 0.41193(19) 0.46759(17) 0.0199(4) Uani 1 1 d . . . . .
H9 H 0.4359 0.3909 0.4050 0.024 Uiso 1 1 calc R U . . .
C10 C 0.2985(3) 0.31436(18) 0.53210(16) 0.0202(4) Uani 1 1 d . . . . .
H10 H 0.3201 0.2270 0.5142 0.024 Uiso 1 1 calc R U . . .
C11 C 0.1976(2) 0.34431(17) 0.62252(15) 0.0189(4) Uani 1 1 d . . . . .
H11 H 0.1488 0.2776 0.6657 0.023 Uiso 1 1 calc R U . . .
C12 C 0.1683(2) 0.47249(18) 0.64958(16) 0.0158(4) Uani 1 1 d . . . . .
H12 H 0.0989 0.4931 0.7111 0.019 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
P1 O1 1.4951(13) . ?
P1 C7 1.8127(19) . ?
P1 C1 1.8266(18) . ?
P1 C5 1.8328(19) . ?
C1 C2 1.543(2) . ?
C1 C6 1.547(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.556(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.549(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C6 1.535(3) . ?
C4 C5 1.543(3) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.394(3) . ?
C7 C12 1.399(3) . ?
C8 C9 1.395(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
O1 P1 C7 111.05(8) . . ?
O1 P1 C1 116.11(8) . . ?
C7 P1 C1 107.35(8) . . ?
O1 P1 C5 116.09(8) . . ?
C7 P1 C5 111.44(9) . . ?
C1 P1 C5 93.48(9) . . ?
C2 C1 C6 101.29(15) . . ?
C2 C1 P1 106.32(12) . . ?
C6 C1 P1 101.44(12) . . ?
C2 C1 H1 115.3 . . ?
C6 C1 H1 115.3 . . ?
P1 C1 H1 115.3 . . ?
C1 C2 C3 104.18(15) . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C4 C3 C2 104.36(15) . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C6 C4 C5 103.94(15) . . ?
C6 C4 C3 102.35(16) . . ?
C5 C4 C3 110.66(16) . . ?
C6 C4 H4 113.0 . . ?
C5 C4 H4 113.0 . . ?
C3 C4 H4 113.0 . . ?
C4 C5 P1 103.00(13) . . ?
C4 C5 H5A 111.2 . . ?
P1 C5 H5A 111.2 . . ?
C4 C5 H5B 111.2 . . ?
P1 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
C4 C6 C1 97.63(14) . . ?
C4 C6 H6A 112.2 . . ?
C1 C6 H6A 112.2 . . ?
C4 C6 H6B 112.2 . . ?
C1 C6 H6B 112.2 . . ?
H6A C6 H6B 109.8 . . ?
C8 C7 C12 119.54(17) . . ?
C8 C7 P1 124.57(15) . . ?
C12 C7 P1 115.88(14) . . ?
C7 C8 C9 119.81(18) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 120.23(18) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.22(17) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.66(17) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C7 120.52(18) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.071

_shelxl_version_number           2014/6

