# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_mo_20181201ZK1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1888995'
loop_
_audit_author_name
_audit_author_address
a
;College of Chemistry, Sichuan University
China
;
_audit_update_record             
;
2019-01-07 deposited with the CCDC.	2019-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 O P S'
_chemical_formula_weight         324.35

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   8.5391(4)
_cell_length_b                   11.0667(5)
_cell_length_c                   16.9456(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1601.35(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9108
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.22

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.301
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5878
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71073    8.541   11.068   16.940   89.992   89.988   90.005
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23660
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.404
_diffrn_reflns_theta_max         28.296
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3962
_reflns_number_gt                3457
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.999

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0489P)²+0.1802P] 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 1324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3962
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0885
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
P1 P 0.35610(8) 0.47212(5) 0.65094(4) 0.02233(16) Uani 1 1 d . . . . .
O1 O 0.2857(2) 0.35301(15) 0.63359(12) 0.0318(5) Uani 1 1 d . . . . .
S1 S 0.56011(8) 0.51501(6) 0.58767(4) 0.02692(16) Uani 1 1 d . . . . .
C1 C 1.0278(4) 0.1146(2) 0.65950(18) 0.0358(7) Uani 1 1 d . . . . .
H1A H 1.045727 0.066954 0.611612 0.054 Uiso 1 1 calc R U . . .
H1B H 0.988048 0.061856 0.701406 0.054 Uiso 1 1 calc R U . . .
H1C H 1.126518 0.151531 0.676501 0.054 Uiso 1 1 calc R U . . .
C2 C 0.9099(3) 0.2120(2) 0.64263(17) 0.0263(6) Uani 1 1 d . . . . .
C3 C 0.8636(3) 0.2924(2) 0.70189(16) 0.0276(6) Uani 1 1 d . . . . .
H3 H 0.907260 0.284741 0.753214 0.033 Uiso 1 1 calc R U . . .
C4 C 0.7552(3) 0.3831(2) 0.68720(16) 0.0260(5) Uani 1 1 d . . . . .
H4 H 0.725785 0.437390 0.728003 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7339(3) 0.3148(2) 0.55272(17) 0.0285(6) Uani 1 1 d . . . . .
H6 H 0.689074 0.321796 0.501610 0.034 Uiso 1 1 calc R U . . .
C5 C 0.6898(3) 0.3939(2) 0.61222(15) 0.0231(5) Uani 1 1 d . . . . .
C8 C 0.2337(3) 0.5976(2) 0.62200(15) 0.0219(5) Uani 1 1 d . . . . .
C7 C 0.8439(3) 0.2253(2) 0.56820(16) 0.0289(6) Uani 1 1 d . . . . .
H7 H 0.874578 0.172014 0.527025 0.035 Uiso 1 1 calc R U . . .
C9 C 0.2901(3) 0.7133(2) 0.60568(16) 0.0259(6) Uani 1 1 d . . . . .
H9 H 0.399092 0.729603 0.609524 0.031 Uiso 1 1 calc R U . . .
C10 C 0.1874(3) 0.8045(2) 0.58385(17) 0.0279(6) Uani 1 1 d . . . . .
H10 H 0.226470 0.882714 0.571819 0.034 Uiso 1 1 calc R U . . .
C11 C 0.0289(3) 0.7821(2) 0.57954(16) 0.0290(6) Uani 1 1 d . . . . .
H11 H -0.041058 0.845013 0.564964 0.035 Uiso 1 1 calc R U . . .
C12 C -0.0288(3) 0.6674(2) 0.59653(16) 0.0296(6) Uani 1 1 d . . . . .
H12 H -0.138126 0.652164 0.593806 0.035 Uiso 1 1 calc R U . . .
C13 C 0.0731(3) 0.5753(2) 0.61739(15) 0.0251(5) Uani 1 1 d . . . . .
H13 H 0.033550 0.496909 0.628579 0.030 Uiso 1 1 calc R U . . .
C14 C 0.4002(3) 0.4908(2) 0.75442(14) 0.0222(5) Uani 1 1 d . . . . .
C15 C 0.4826(3) 0.5904(2) 0.78278(15) 0.0261(5) Uani 1 1 d . . . . .
H15 H 0.518843 0.650310 0.747033 0.031 Uiso 1 1 calc R U . . .
C16 C 0.5119(3) 0.6026(2) 0.86245(16) 0.0301(6) Uani 1 1 d . . . . .
H16 H 0.568555 0.670472 0.881476 0.036 Uiso 1 1 calc R U . . .
C17 C 0.4583(3) 0.5154(3) 0.91466(16) 0.0341(6) Uani 1 1 d . . . . .
H17 H 0.479214 0.523388 0.969473 0.041 Uiso 1 1 calc R U . . .
C18 C 0.3743(4) 0.4165(3) 0.88734(17) 0.0339(6) Uani 1 1 d . . . . .
H18 H 0.337009 0.357652 0.923586 0.041 Uiso 1 1 calc R U . . .
C19 C 0.3447(3) 0.4032(2) 0.80740(16) 0.0271(5) Uani 1 1 d . . . . .
H19 H 0.287427 0.335464 0.788637 0.032 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 1.4784(18) . ?
P1 C14 1.805(3) . ?
P1 C8 1.806(3) . ?
P1 S1 2.0999(9) . ?
S1 C5 1.788(2) . ?
C1 C2 1.503(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.389(4) . ?
C2 C3 1.398(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9500 . ?
C6 C5 1.387(4) . ?
C6 C7 1.391(4) . ?
C6 H6 0.9500 . ?
C8 C9 1.396(3) . ?
C8 C13 1.395(4) . ?
C7 H7 0.9500 . ?
C9 C10 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C14 C19 1.404(3) . ?
C15 C16 1.380(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(4) . ?
C18 H18 0.9500 . ?
C19 H19 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 C14 112.35(11) . . ?
O1 P1 C8 113.34(12) . . ?
C14 P1 C8 107.22(11) . . ?
O1 P1 S1 115.94(9) . . ?
C14 P1 S1 107.28(8) . . ?
C8 P1 S1 99.66(9) . . ?
C5 S1 P1 103.05(8) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.1(2) . . ?
C7 C2 C1 121.3(2) . . ?
C3 C2 C1 120.6(3) . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C5 C6 C7 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 S1 118.2(2) . . ?
C4 C5 S1 121.68(19) . . ?
C9 C8 C13 119.4(2) . . ?
C9 C8 P1 124.0(2) . . ?
C13 C8 P1 116.61(18) . . ?
C2 C7 C6 121.3(2) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
C15 C14 C19 119.7(2) . . ?
C15 C14 P1 122.09(18) . . ?
C19 C14 P1 118.14(19) . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 119.4(3) . . ?
C18 C19 H19 120.3 . . ?
C14 C19 H19 120.3 . . ?

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
C7 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 C4 179.8(2) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C7 C6 C5 C4 -0.3(4) . . . . ?
C7 C6 C5 S1 175.1(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C5 S1 -175.6(2) . . . . ?
P1 S1 C5 C6 113.8(2) . . . . ?
P1 S1 C5 C4 -70.9(2) . . . . ?
O1 P1 C8 C9 -156.4(2) . . . . ?
C14 P1 C8 C9 79.1(2) . . . . ?
S1 P1 C8 C9 -32.6(2) . . . . ?
O1 P1 C8 C13 24.7(2) . . . . ?
C14 P1 C8 C13 -99.9(2) . . . . ?
S1 P1 C8 C13 148.50(19) . . . . ?
C3 C2 C7 C6 -0.6(4) . . . . ?
C1 C2 C7 C6 179.5(3) . . . . ?
C5 C6 C7 C2 0.8(4) . . . . ?
C13 C8 C9 C10 -1.0(4) . . . . ?
P1 C8 C9 C10 -180.0(2) . . . . ?
C8 C9 C10 C11 1.2(4) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C8 0.5(4) . . . . ?
C9 C8 C13 C12 0.2(4) . . . . ?
P1 C8 C13 C12 179.2(2) . . . . ?
O1 P1 C14 C15 172.8(2) . . . . ?
C8 P1 C14 C15 -62.0(2) . . . . ?
S1 P1 C14 C15 44.2(2) . . . . ?
O1 P1 C14 C19 -9.1(2) . . . . ?
C8 P1 C14 C19 116.1(2) . . . . ?
S1 P1 C14 C19 -137.66(18) . . . . ?
C19 C14 C15 C16 0.9(4) . . . . ?
P1 C14 C15 C16 179.0(2) . . . . ?
C14 C15 C16 C17 -0.3(4) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C16 C17 C18 C19 0.7(4) . . . . ?
C17 C18 C19 C14 -0.1(4) . . . . ?
C15 C14 C19 C18 -0.7(4) . . . . ?
P1 C14 C19 C18 -178.8(2) . . . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_mo_181201zk2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1888996'
loop_
_audit_author_name
_audit_author_address
b
;College of Chemistry, Sichuan University
China
;
_audit_update_record             
;
2019-01-07 deposited with the CCDC.	2019-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 O2 P'
_chemical_formula_weight         350.37

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.9390(15)
_cell_length_b                   11.3093(18)
_cell_length_c                   9.5031(17)
_cell_angle_alpha                90
_cell_angle_beta                 100.362(5)
_cell_angle_gamma                90
_cell_volume                     945.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3342
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      27.33

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.157
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5095
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71091    8.960   11.318    9.521   90.001  100.302   89.998
;
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13886
_diffrn_reflns_av_unetI/netI     0.1056
_diffrn_reflns_av_R_equivalents  0.0930
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.827
_diffrn_reflns_theta_max         28.382
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4654
_reflns_number_gt                3416
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.983

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0618P)²+0.5370P] 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 1174 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(10)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         4654
_refine_ls_number_parameters     229
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1624
_refine_ls_wR_factor_gt          0.1291
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
P1 P 0.41734(13) 0.43316(10) 0.48340(12) 0.0259(3) Uani 1 1 d . . . . .
O1 O 0.4011(4) 0.3066(3) 0.5135(4) 0.0360(9) Uani 1 1 d . . . . .
C1 C 1.1492(8) 0.5452(6) 1.0271(7) 0.0550(18) Uani 1 1 d . . . . .
H1A H 1.140841 0.620286 0.974880 0.083 Uiso 1 1 calc R U . . .
H1B H 1.253516 0.535327 1.079189 0.083 Uiso 1 1 calc R U . . .
H1C H 1.078730 0.545221 1.095046 0.083 Uiso 1 1 calc R U . . .
O2 O 0.5051(4) 0.5118(3) 0.6115(4) 0.0280(7) Uani 1 1 d . . . . .
C2 C 1.1295(8) 0.3280(6) 1.0090(8) 0.0549(18) Uani 1 1 d . . . . .
H2A H 1.109703 0.260240 0.944026 0.082 Uiso 1 1 calc R U . . .
H2B H 1.057769 0.327033 1.075707 0.082 Uiso 1 1 calc R U . . .
H2C H 1.233739 0.323336 1.062727 0.082 Uiso 1 1 calc R U . . .
C3 C 1.1097(5) 0.4435(5) 0.9216(5) 0.0347(11) Uani 1 1 d . . . . .
C4 C 1.2226(6) 0.4393(8) 0.8182(6) 0.0549(15) Uani 1 1 d . . . . .
H4A H 1.193267 0.376226 0.747919 0.082 Uiso 1 1 calc R U . . .
H4B H 1.324958 0.423573 0.871864 0.082 Uiso 1 1 calc R U . . .
H4C H 1.221954 0.515321 0.768685 0.082 Uiso 1 1 calc R U . . .
C5 C 0.9490(6) 0.4581(4) 0.8364(5) 0.0301(11) Uani 1 1 d . . . . .
C6 C 0.8404(6) 0.3694(4) 0.8274(5) 0.0321(11) Uani 1 1 d . . . . .
H6 H 0.866876 0.296405 0.875015 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6556(5) 0.4891(4) 0.6823(5) 0.0256(9) Uani 1 1 d . . . . .
C7 C 0.6940(6) 0.3846(4) 0.7507(5) 0.0298(10) Uani 1 1 d . . . . .
H7 H 0.621397 0.322696 0.745910 0.036 Uiso 1 1 calc R U . . .
C9 C 0.7596(6) 0.5798(4) 0.6875(5) 0.0332(11) Uani 1 1 d . . . . .
H9 H 0.732150 0.652211 0.639102 0.040 Uiso 1 1 calc R U . . .
C10 C 0.9029(6) 0.5633(5) 0.7639(6) 0.0367(12) Uani 1 1 d . . . . .
H10 H 0.974283 0.625956 0.767978 0.044 Uiso 1 1 calc R U . . .
C11 C 0.5122(5) 0.4569(4) 0.3344(5) 0.0286(11) Uani 1 1 d . . . . .
C12 C 0.5485(5) 0.5709(4) 0.2963(5) 0.0311(10) Uani 1 1 d . . . . .
H12 H 0.530966 0.636428 0.353705 0.037 Uiso 1 1 calc R U . . .
C13 C 0.6105(6) 0.5883(5) 0.1740(6) 0.0407(13) Uani 1 1 d . . . . .
H13 H 0.634793 0.666133 0.147806 0.049 Uiso 1 1 calc R U . . .
C14 C 0.6370(7) 0.4949(6) 0.0912(7) 0.0483(15) Uani 1 1 d . . . . .
H14 H 0.678817 0.508189 0.007469 0.058 Uiso 1 1 calc R U . . .
C15 C 0.6034(7) 0.3808(6) 0.1280(6) 0.0496(16) Uani 1 1 d . . . . .
H15 H 0.623043 0.316089 0.070300 0.060 Uiso 1 1 calc R U . . .
C16 C 0.5397(6) 0.3609(5) 0.2517(6) 0.0386(12) Uani 1 1 d . . . . .
H16 H 0.515978 0.282962 0.277830 0.046 Uiso 1 1 calc R U . . .
C17 C 0.2416(6) 0.5123(4) 0.4517(5) 0.0282(10) Uani 1 1 d . . . . .
C18 C 0.2346(6) 0.6344(4) 0.4660(5) 0.0309(11) Uani 1 1 d . . . . .
H18 H 0.325975 0.678447 0.491743 0.037 Uiso 1 1 calc R U . . .
C19 C 0.0960(6) 0.6927(5) 0.4431(6) 0.0343(11) Uani 1 1 d . . . . .
H19 H 0.092152 0.776184 0.452543 0.041 Uiso 1 1 calc R U . . .
C20 C -0.0372(6) 0.6278(5) 0.4063(6) 0.0399(13) Uani 1 1 d . . . . .
H20 H -0.132771 0.667032 0.391977 0.048 Uiso 1 1 calc R U . . .
C21 C -0.0314(6) 0.5061(5) 0.3904(6) 0.0410(13) Uani 1 1 d . . . . .
H21 H -0.122776 0.462324 0.363694 0.049 Uiso 1 1 calc R U . . .
C22 C 0.1060(5) 0.4488(5) 0.4130(5) 0.0316(11) Uani 1 1 d . . . . .
H22 H 0.109261 0.365341 0.402273 0.038 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 1.472(3) . ?
P1 O2 1.595(3) . ?
P1 C17 1.786(5) . ?
P1 C11 1.797(5) . ?
C1 C3 1.525(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
O2 C8 1.415(6) . ?
C2 C3 1.540(8) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C5 1.526(6) . ?
C3 C4 1.531(8) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.388(7) . ?
C5 C10 1.399(7) . ?
C6 C7 1.390(7) . ?
C6 H6 0.9500 . ?
C8 C7 1.363(6) . ?
C8 C9 1.378(7) . ?
C7 H7 0.9500 . ?
C9 C10 1.367(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.387(6) . ?
C11 C12 1.394(7) . ?
C12 C13 1.388(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.364(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.413(9) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.391(7) . ?
C17 C22 1.400(7) . ?
C18 C19 1.386(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(8) . ?
C20 H20 0.9500 . ?
C21 C22 1.371(7) . ?
C21 H21 0.9500 . ?
C22 H22 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 O2 116.49(19) . . ?
O1 P1 C17 113.9(2) . . ?
O2 P1 C17 98.4(2) . . ?
O1 P1 C11 112.0(2) . . ?
O2 P1 C11 106.3(2) . . ?
C17 P1 C11 108.5(2) . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C8 O2 P1 123.9(3) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 C5 110.6(5) . . ?
C1 C3 C4 110.1(5) . . ?
C5 C3 C4 109.2(4) . . ?
C1 C3 C2 107.1(4) . . ?
C5 C3 C2 112.6(5) . . ?
C4 C3 C2 107.1(5) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 116.3(4) . . ?
C6 C5 C3 122.3(4) . . ?
C10 C5 C3 121.3(5) . . ?
C5 C6 C7 121.6(5) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C7 C8 C9 121.2(4) . . ?
C7 C8 O2 121.3(4) . . ?
C9 C8 O2 117.4(4) . . ?
C8 C7 C6 119.4(5) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C10 C9 C8 118.6(5) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C5 122.9(5) . . ?
C9 C10 H10 118.6 . . ?
C5 C10 H10 118.6 . . ?
C16 C11 C12 120.2(5) . . ?
C16 C11 P1 119.1(4) . . ?
C12 C11 P1 120.5(4) . . ?
C13 C12 C11 119.7(5) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.6(6) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.6(6) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C11 C16 C15 119.0(6) . . ?
C11 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C18 C17 C22 118.9(5) . . ?
C18 C17 P1 122.3(4) . . ?
C22 C17 P1 118.7(4) . . ?
C19 C18 C17 120.8(5) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 119.4(5) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 120.3(5) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.2(5) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 120.5(5) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?

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
O1 P1 O2 C8 57.6(4) . . . . ?
C17 P1 O2 C8 179.7(4) . . . . ?
C11 P1 O2 C8 -68.1(4) . . . . ?
C1 C3 C5 C6 -126.8(6) . . . . ?
C4 C3 C5 C6 111.9(6) . . . . ?
C2 C3 C5 C6 -7.0(7) . . . . ?
C1 C3 C5 C10 52.4(7) . . . . ?
C4 C3 C5 C10 -68.9(7) . . . . ?
C2 C3 C5 C10 172.2(5) . . . . ?
C10 C5 C6 C7 0.0(7) . . . . ?
C3 C5 C6 C7 179.3(5) . . . . ?
P1 O2 C8 C7 -59.3(6) . . . . ?
P1 O2 C8 C9 124.9(4) . . . . ?
C9 C8 C7 C6 0.2(7) . . . . ?
O2 C8 C7 C6 -175.4(5) . . . . ?
C5 C6 C7 C8 0.0(8) . . . . ?
C7 C8 C9 C10 -0.4(7) . . . . ?
O2 C8 C9 C10 175.4(5) . . . . ?
C8 C9 C10 C5 0.4(8) . . . . ?
C6 C5 C10 C9 -0.2(8) . . . . ?
C3 C5 C10 C9 -179.5(5) . . . . ?
O1 P1 C11 C16 9.2(5) . . . . ?
O2 P1 C11 C16 137.5(4) . . . . ?
C17 P1 C11 C16 -117.4(4) . . . . ?
O1 P1 C11 C12 -175.1(4) . . . . ?
O2 P1 C11 C12 -46.8(4) . . . . ?
C17 P1 C11 C12 58.2(4) . . . . ?
C16 C11 C12 C13 0.8(7) . . . . ?
P1 C11 C12 C13 -174.8(4) . . . . ?
C11 C12 C13 C14 -0.3(8) . . . . ?
C12 C13 C14 C15 -0.4(9) . . . . ?
C13 C14 C15 C16 0.6(10) . . . . ?
C12 C11 C16 C15 -0.6(7) . . . . ?
P1 C11 C16 C15 175.0(4) . . . . ?
C14 C15 C16 C11 -0.1(8) . . . . ?
O1 P1 C17 C18 159.3(4) . . . . ?
O2 P1 C17 C18 35.3(4) . . . . ?
C11 P1 C17 C18 -75.1(5) . . . . ?
O1 P1 C17 C22 -19.8(5) . . . . ?
O2 P1 C17 C22 -143.8(4) . . . . ?
C11 P1 C17 C22 105.7(4) . . . . ?
C22 C17 C18 C19 0.3(8) . . . . ?
P1 C17 C18 C19 -178.8(4) . . . . ?
C17 C18 C19 C20 0.4(8) . . . . ?
C18 C19 C20 C21 -1.0(9) . . . . ?
C19 C20 C21 C22 1.0(9) . . . . ?
C20 C21 C22 C17 -0.3(9) . . . . ?
C18 C17 C22 C21 -0.4(8) . . . . ?
P1 C17 C22 C21 178.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9 O1 0.95 2.44 3.362(6) 164.0 2_656
C12 H12 O1 0.95 2.32 3.207(6) 154.8 2_656

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.063

