# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_leung676
_database_code_depnum_ccdc_archive 'CCDC 1472772'
_audit_update_record             
;
2016-04-07 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_absolute_configuration ad
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H38 Cl N2 O P Pd'
_chemical_formula_sum            'C40 H38 Cl N2 O P Pd'
_chemical_formula_weight         735.54

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'
N N 0.0061 0.0033 '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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_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                   13.6455(9)
_cell_length_b                   14.6229(9)
_cell_length_c                   17.8347(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3558.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    5438
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      28.80

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1512
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7741
_exptl_absorpt_correction_T_max  0.8997
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22384
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         30.53
_reflns_number_total             10237
_reflns_number_gt                7919
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0639P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_number_reflns         10237
_refine_ls_number_parameters     418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.731496(19) 0.25055(2) 0.216497(14) 0.01849(7) Uani 1 1 d . . .
C1 C 0.6256(3) 0.3155(3) 0.2730(2) 0.0199(8) Uani 1 1 d . . .
C2 C 0.6345(3) 0.3560(3) 0.3450(2) 0.0216(8) Uani 1 1 d . . .
H2 H 0.6978 0.3649 0.3658 0.026 Uiso 1 1 calc R . .
C3 C 0.5533(3) 0.3827(3) 0.3853(2) 0.0228(9) Uani 1 1 d . . .
H3 H 0.5615 0.4076 0.4341 0.027 Uiso 1 1 calc R . .
C4 C 0.4586(3) 0.3737(3) 0.3554(2) 0.0202(8) Uani 1 1 d . . .
C5 C 0.3744(3) 0.4005(3) 0.3966(3) 0.0258(9) Uani 1 1 d . . .
H5 H 0.3813 0.4225 0.4464 0.031 Uiso 1 1 calc R . .
C6 C 0.2837(3) 0.3949(3) 0.3649(3) 0.0339(11) Uani 1 1 d . . .
H6 H 0.2276 0.4124 0.3929 0.041 Uiso 1 1 calc R . .
C7 C 0.2731(3) 0.3630(3) 0.2905(3) 0.0325(10) Uani 1 1 d . . .
H7 H 0.2097 0.3605 0.2685 0.039 Uiso 1 1 calc R . .
C8 C 0.3528(3) 0.3357(3) 0.2498(3) 0.0266(9) Uani 1 1 d . . .
H8 H 0.3441 0.3149 0.1997 0.032 Uiso 1 1 calc R . .
C9 C 0.4476(3) 0.3380(3) 0.2812(2) 0.0201(7) Uani 1 1 d . . .
C10 C 0.5331(3) 0.3061(3) 0.2428(2) 0.0203(8) Uani 1 1 d . . .
C11 C 0.5266(3) 0.2576(3) 0.1681(2) 0.0237(8) Uani 1 1 d . . .
H11 H 0.4608 0.2279 0.1634 0.028 Uiso 1 1 calc R . .
C12 C 0.5402(4) 0.3254(3) 0.1037(3) 0.0326(10) Uani 1 1 d . . .
H12A H 0.6067 0.3506 0.1054 0.049 Uiso 1 1 calc R . .
H12B H 0.4925 0.3751 0.1086 0.049 Uiso 1 1 calc R . .
H12C H 0.5301 0.2939 0.0558 0.049 Uiso 1 1 calc R . .
C13 C 0.5729(3) 0.1082(3) 0.2203(3) 0.0282(9) Uani 1 1 d . . .
H13A H 0.5145 0.0788 0.1994 0.042 Uiso 1 1 calc R . .
H13B H 0.5575 0.1331 0.2700 0.042 Uiso 1 1 calc R . .
H13C H 0.6257 0.0631 0.2248 0.042 Uiso 1 1 calc R . .
C14 C 0.6220(3) 0.1452(3) 0.0943(3) 0.0316(10) Uani 1 1 d . . .
H14A H 0.5593 0.1258 0.0727 0.047 Uiso 1 1 calc R . .
H14B H 0.6658 0.0924 0.0985 0.047 Uiso 1 1 calc R . .
H14C H 0.6521 0.1915 0.0619 0.047 Uiso 1 1 calc R . .
C15 C 0.9384(3) 0.3561(3) 0.1653(2) 0.0192(8) Uani 1 1 d . . .
H15 H 0.9632 0.2935 0.1530 0.023 Uiso 1 1 calc R . .
C16 C 1.0294(3) 0.4163(3) 0.1793(2) 0.0206(8) Uani 1 1 d . . .
H16A H 1.0113 0.4815 0.1743 0.025 Uiso 1 1 calc R . .
H16B H 1.0537 0.4062 0.2309 0.025 Uiso 1 1 calc R . .
C17 C 1.1108(3) 0.3934(3) 0.1231(2) 0.0209(8) Uani 1 1 d . . .
C18 C 1.1865(3) 0.4626(3) 0.1056(2) 0.0185(8) Uani 1 1 d . . .
C19 C 1.2613(3) 0.4395(3) 0.0558(2) 0.0234(8) Uani 1 1 d . . .
H19 H 1.2623 0.3800 0.0343 0.028 Uiso 1 1 calc R . .
C20 C 1.3332(3) 0.5006(3) 0.0371(3) 0.0309(10) Uani 1 1 d . . .
H20 H 1.3832 0.4834 0.0028 0.037 Uiso 1 1 calc R . .
C21 C 1.3332(4) 0.5868(3) 0.0679(3) 0.0353(11) Uani 1 1 d . . .
H21 H 1.3836 0.6290 0.0557 0.042 Uiso 1 1 calc R . .
C22 C 1.2597(4) 0.6116(3) 0.1166(3) 0.0377(12) Uani 1 1 d . . .
H22 H 1.2590 0.6716 0.1370 0.045 Uiso 1 1 calc R . .
C23 C 1.1872(3) 0.5509(3) 0.1361(3) 0.0294(10) Uani 1 1 d . . .
H23 H 1.1374 0.5689 0.1703 0.035 Uiso 1 1 calc R . .
C24 C 0.8795(3) 0.3877(3) 0.0982(2) 0.0207(8) Uani 1 1 d . . .
C25 C 0.8600(4) 0.4801(3) 0.0850(2) 0.0290(10) Uani 1 1 d . . .
H25 H 0.8856 0.5237 0.1193 0.035 Uiso 1 1 calc R . .
N2 N 0.8074(3) 0.5112(3) 0.0267(2) 0.0368(10) Uani 1 1 d . . .
C27 C 0.7748(4) 0.4495(4) -0.0216(3) 0.0423(13) Uani 1 1 d . . .
H27 H 0.7383 0.4702 -0.0637 0.051 Uiso 1 1 calc R . .
C28 C 0.7910(4) 0.3566(4) -0.0142(3) 0.0430(14) Uani 1 1 d . . .
H28 H 0.7661 0.3149 -0.0503 0.052 Uiso 1 1 calc R . .
C29 C 0.8439(4) 0.3257(3) 0.0463(2) 0.0310(10) Uani 1 1 d . . .
H29 H 0.8559 0.2622 0.0525 0.037 Uiso 1 1 calc R . .
C30 C 0.8325(3) 0.4620(3) 0.2749(2) 0.0195(8) Uani 1 1 d . . .
C31 C 0.9006(3) 0.5119(3) 0.3169(2) 0.0213(8) Uani 1 1 d . . .
H31 H 0.9582 0.4829 0.3350 0.026 Uiso 1 1 calc R . .
C32 C 0.8843(3) 0.6036(3) 0.3321(3) 0.0254(9) Uani 1 1 d . . .
H32 H 0.9301 0.6373 0.3612 0.030 Uiso 1 1 calc R . .
C33 C 0.7998(3) 0.6464(3) 0.3043(2) 0.0279(9) Uani 1 1 d . . .
H33 H 0.7884 0.7092 0.3149 0.034 Uiso 1 1 calc R . .
C34 C 0.7323(3) 0.5976(3) 0.2612(3) 0.0283(9) Uani 1 1 d . . .
H34 H 0.6759 0.6274 0.2417 0.034 Uiso 1 1 calc R . .
C35 C 0.7479(3) 0.5049(3) 0.2467(3) 0.0259(9) Uani 1 1 d . . .
H35 H 0.7018 0.4710 0.2181 0.031 Uiso 1 1 calc R . .
C36 C 0.9345(3) 0.3001(3) 0.3231(2) 0.0211(8) Uani 1 1 d . . .
C37 C 1.0178(3) 0.2487(4) 0.3064(2) 0.0270(8) Uani 1 1 d . . .
H37 H 1.0341 0.2369 0.2555 0.032 Uiso 1 1 calc R . .
C38 C 1.0775(4) 0.2144(3) 0.3636(3) 0.0345(11) Uani 1 1 d . . .
H38 H 1.1351 0.1812 0.3514 0.041 Uiso 1 1 calc R . .
C39 C 1.0530(4) 0.2286(3) 0.4371(3) 0.0361(12) Uani 1 1 d . . .
H39 H 1.0938 0.2052 0.4758 0.043 Uiso 1 1 calc R . .
C40 C 0.9685(4) 0.2774(3) 0.4555(3) 0.0351(12) Uani 1 1 d . . .
H40 H 0.9506 0.2853 0.5066 0.042 Uiso 1 1 calc R . .
C41 C 0.9109(3) 0.3140(3) 0.3994(3) 0.0295(10) Uani 1 1 d . . .
H41 H 0.8546 0.3490 0.4122 0.035 Uiso 1 1 calc R . .
Cl1 Cl 0.84650(7) 0.13886(7) 0.16831(6) 0.0262(2) Uani 1 1 d . . .
N1 N 0.6051(3) 0.1844(2) 0.1694(2) 0.0227(7) Uani 1 1 d . . .
O1 O 1.1142(2) 0.3169(2) 0.09576(19) 0.0318(8) Uani 1 1 d . . .
P1 P 0.85625(7) 0.34323(7) 0.24890(6) 0.0181(2) Uani 1 1 d . . .


_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 C1 2.001(4) . ?
Pd1 N1 2.148(3) . ?
Pd1 P1 2.2514(11) . ?
Pd1 Cl1 2.4226(10) . ?
C1 C10 1.380(6) . ?
C1 C2 1.419(6) . ?
C2 C3 1.377(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.405(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(6) . ?
C4 C9 1.432(6) . ?
C5 C6 1.363(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.414(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.367(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.411(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.430(6) . ?
C10 C11 1.512(6) . ?
C11 N1 1.515(6) . ?
C11 C12 1.527(6) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N1 1.503(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N1 1.475(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C24 1.514(5) . ?
C15 C16 1.543(5) . ?
C15 P1 1.874(4) . ?
C15 H15 1.0000 . ?
C16 C17 1.532(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O1 1.221(5) . ?
C17 C18 1.480(6) . ?
C18 C19 1.394(6) . ?
C18 C23 1.402(6) . ?
C19 C20 1.368(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.375(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.373(6) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C29 1.384(6) . ?
C24 C25 1.398(6) . ?
C25 N2 1.342(6) . ?
C25 H25 0.9500 . ?
N2 C27 1.325(6) . ?
C27 C28 1.382(7) . ?
C27 H27 0.9500 . ?
C28 C29 1.375(6) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C31 1.399(6) . ?
C30 C35 1.407(6) . ?
C30 P1 1.826(4) . ?
C31 C32 1.386(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.403(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.396(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.397(6) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C37 1.395(6) . ?
C36 C41 1.412(6) . ?
C36 P1 1.814(4) . ?
C37 C38 1.399(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.369(7) . ?
C38 H38 0.9500 . ?
C39 C40 1.395(7) . ?
C39 H39 0.9500 . ?
C40 C41 1.382(6) . ?
C40 H40 0.9500 . ?
C41 H41 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
C1 Pd1 N1 80.27(15) . . ?
C1 Pd1 P1 97.51(12) . . ?
N1 Pd1 P1 168.06(10) . . ?
C1 Pd1 Cl1 165.10(11) . . ?
N1 Pd1 Cl1 94.47(10) . . ?
P1 Pd1 Cl1 90.41(4) . . ?
C10 C1 C2 118.2(4) . . ?
C10 C1 Pd1 114.7(3) . . ?
C2 C1 Pd1 126.3(3) . . ?
C3 C2 C1 121.5(4) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 121.6(4) . . ?
C3 C4 C9 118.7(4) . . ?
C5 C4 C9 119.7(4) . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.8(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 123.4(4) . . ?
C8 C9 C4 118.1(4) . . ?
C10 C9 C4 118.5(3) . . ?
C1 C10 C9 121.8(4) . . ?
C1 C10 C11 116.4(4) . . ?
C9 C10 C11 121.8(3) . . ?
C10 C11 N1 106.0(3) . . ?
C10 C11 C12 110.5(4) . . ?
N1 C11 C12 112.6(3) . . ?
C10 C11 H11 109.2 . . ?
N1 C11 H11 109.2 . . ?
C12 C11 H11 109.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C24 C15 C16 112.4(3) . . ?
C24 C15 P1 110.0(3) . . ?
C16 C15 P1 114.2(3) . . ?
C24 C15 H15 106.6 . . ?
C16 C15 H15 106.6 . . ?
P1 C15 H15 106.6 . . ?
C17 C16 C15 110.7(3) . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
O1 C17 C18 120.9(4) . . ?
O1 C17 C16 119.3(4) . . ?
C18 C17 C16 119.7(4) . . ?
C19 C18 C23 117.7(4) . . ?
C19 C18 C17 118.7(4) . . ?
C23 C18 C17 123.5(4) . . ?
C20 C19 C18 121.5(4) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 120.1(4) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 119.6(4) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C23 C22 C21 121.0(5) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C18 120.1(4) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 H23 119.9 . . ?
C29 C24 C25 116.9(4) . . ?
C29 C24 C15 121.0(4) . . ?
C25 C24 C15 122.0(4) . . ?
N2 C25 C24 124.1(4) . . ?
N2 C25 H25 117.9 . . ?
C24 C25 H25 117.9 . . ?
C27 N2 C25 116.9(4) . . ?
N2 C27 C28 123.6(4) . . ?
N2 C27 H27 118.2 . . ?
C28 C27 H27 118.2 . . ?
C29 C28 C27 118.8(5) . . ?
C29 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C28 C29 C24 119.7(4) . . ?
C28 C29 H29 120.2 . . ?
C24 C29 H29 120.2 . . ?
C31 C30 C35 120.2(4) . . ?
C31 C30 P1 121.0(3) . . ?
C35 C30 P1 118.6(3) . . ?
C32 C31 C30 120.2(4) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C33 119.6(4) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C34 C33 C32 120.6(4) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C35 119.8(4) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C34 C35 C30 119.5(4) . . ?
C34 C35 H35 120.2 . . ?
C30 C35 H35 120.2 . . ?
C37 C36 C41 118.0(4) . . ?
C37 C36 P1 120.7(3) . . ?
C41 C36 P1 121.2(3) . . ?
C36 C37 C38 120.7(4) . . ?
C36 C37 H37 119.6 . . ?
C38 C37 H37 119.6 . . ?
C39 C38 C37 120.2(5) . . ?
C39 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C38 C39 C40 120.3(4) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C41 C40 C39 119.8(5) . . ?
C41 C40 H40 120.1 . . ?
C39 C40 H40 120.1 . . ?
C40 C41 C36 120.8(5) . . ?
C40 C41 H41 119.6 . . ?
C36 C41 H41 119.6 . . ?
C14 N1 C13 107.8(3) . . ?
C14 N1 C11 111.7(3) . . ?
C13 N1 C11 109.0(3) . . ?
C14 N1 Pd1 113.9(3) . . ?
C13 N1 Pd1 109.4(3) . . ?
C11 N1 Pd1 104.9(2) . . ?
C36 P1 C30 104.43(19) . . ?
C36 P1 C15 105.26(18) . . ?
C30 P1 C15 102.29(18) . . ?
C36 P1 Pd1 115.03(14) . . ?
C30 P1 Pd1 120.24(13) . . ?
C15 P1 Pd1 107.97(13) . . ?

_diffrn_measured_fraction_theta_max 0.940
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.586
_refine_diff_density_min         -1.159
_refine_diff_density_rms         0.358
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DCM/n-hexane
####################################################################### 
# 
# 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_leung934
_database_code_depnum_ccdc_archive 'CCDC 1472773'
_audit_update_record             
;
2016-04-07 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 N O2 P S'
_chemical_formula_iupac          ?
_chemical_formula_weight         443.47
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   6.2681(5)
_cell_length_b                   16.6286(15)
_cell_length_c                   21.762(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2268.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1856
_cell_measurement_theta_min      3.0835
_cell_measurement_theta_max      28.1528
_cell_measurement_temperature    153.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928

_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      153.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            13613
_diffrn_reflns_av_R_equivalents  0.1174
_diffrn_reflns_av_unetI/netI     0.1581
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_full        28.82
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       29

_refine_special_details          
;
;

_reflns_number_total             5907
_reflns_number_gt                3528
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1276
_refine_ls_R_factor_gt           0.0699
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1597
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_number_reflns         5907
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0278P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.412
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 899 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(15)

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'
N N 0.0061 0.0033 '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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4316(9) 0.6561(3) 0.5374(3) 0.0286(13) Uani d . . . 1 . .
H H1 0.4577 0.7005 0.511 0.034 Uiso calc U . R 1 . .
C C2 0.5871(9) 0.5999(3) 0.5465(3) 0.0307(14) Uani d . . . 1 . .
H H2 0.7194 0.6054 0.5256 0.037 Uiso calc U . R 1 . .
C C3 0.5564(9) 0.5351(3) 0.5854(3) 0.0262(12) Uani d . . . 1 . .
H H3 0.664 0.4955 0.5907 0.031 Uiso calc U . R 1 . .
C C4 0.3624(8) 0.5299(3) 0.6167(3) 0.0211(11) Uani d . . . 1 . .
C C5 0.2077(8) 0.5874(3) 0.6060(3) 0.0237(12) Uani d . . . 1 . .
H H5 0.0755 0.5838 0.6271 0.028 Uiso calc U . R 1 . .
C C6 0.3240(7) 0.4673(3) 0.6660(2) 0.0193(11) Uani d . . . 1 . .
H H6 0.1689 0.469 0.6767 0.023 Uiso calc U . R 1 . .
C C7 0.3768(8) 0.3807(3) 0.6466(3) 0.0239(12) Uani d . . . 1 . .
H H7A 0.5164 0.38 0.6253 0.029 Uiso calc U . R 1 . .
H H7B 0.3887 0.3465 0.6837 0.029 Uiso calc U . R 1 . .
C C8 0.2087(9) 0.3467(3) 0.6047(3) 0.0285(13) Uani d . . . 1 . .
C C9 0.2307(10) 0.2611(3) 0.5836(3) 0.0297(13) Uani d . . . 1 . .
C C10 0.4088(10) 0.2140(3) 0.5993(3) 0.0347(15) Uani d . . . 1 . .
H H10 0.5226 0.2369 0.6222 0.042 Uiso calc U . R 1 . .
C C11 0.4187(13) 0.1343(4) 0.5813(3) 0.050(2) Uani d . . . 1 . .
H H11 0.5396 0.1025 0.5914 0.06 Uiso calc U . R 1 . .
C C12 0.2518(13) 0.1012(4) 0.5486(3) 0.056(2) Uani d . . . 1 . .
H H12 0.2579 0.0462 0.5368 0.067 Uiso calc U . R 1 . .
C C13 0.0759(13) 0.1467(4) 0.5328(3) 0.0500(19) Uani d . . . 1 . .
H H13 -0.0371 0.1234 0.5098 0.06 Uiso calc U . R 1 . .
C C14 0.0651(11) 0.2264(4) 0.5506(3) 0.0407(16) Uani d . . . 1 . .
H H14 -0.0564 0.2577 0.5401 0.049 Uiso calc U . R 1 . .
C C15 0.4000(8) 0.4307(3) 0.7976(3) 0.0229(12) Uani d . . . 1 . .
C C16 0.2066(9) 0.3897(3) 0.7991(3) 0.0348(15) Uani d . . . 1 . .
H H16 0.105 0.3978 0.7673 0.042 Uiso calc U . R 1 . .
C C17 0.1619(10) 0.3371(4) 0.8470(4) 0.0439(18) Uani d . . . 1 . .
H H17 0.0292 0.3095 0.8478 0.053 Uiso calc U . R 1 . .
C C18 0.3076(11) 0.3244(4) 0.8932(3) 0.0444(18) Uani d . . . 1 . .
H H18 0.2766 0.2877 0.9254 0.053 Uiso calc U . R 1 . .
C C19 0.4993(12) 0.3653(4) 0.8925(3) 0.0441(17) Uani d . . . 1 . .
H H19 0.5999 0.3573 0.9245 0.053 Uiso calc U . R 1 . .
C C20 0.5452(10) 0.4183(3) 0.8450(3) 0.0348(14) Uani d . . . 1 . .
H H20 0.6772 0.4464 0.8448 0.042 Uiso calc U . R 1 . .
C C21 0.3697(8) 0.5942(3) 0.7542(3) 0.0230(12) Uani d . . . 1 . .
C C22 0.1852(9) 0.6025(3) 0.7883(3) 0.0276(14) Uani d . . . 1 . .
H H22 0.1186 0.5563 0.8054 0.033 Uiso calc U . R 1 . .
C C23 0.0958(11) 0.6785(4) 0.7979(4) 0.0469(19) Uani d . . . 1 . .
H H23 -0.0309 0.6838 0.8215 0.056 Uiso calc U . R 1 . .
C C24 0.1902(13) 0.7451(4) 0.7735(4) 0.056(2) Uani d . . . 1 . .
H H24 0.1281 0.7966 0.7795 0.067 Uiso calc U . R 1 . .
C C25 0.3756(14) 0.7376(3) 0.7399(4) 0.057(2) Uani d . . . 1 . .
H H25 0.4428 0.7843 0.7238 0.068 Uiso calc U . R 1 . .
C C26 0.4643(11) 0.6632(3) 0.7296(3) 0.0385(15) Uani d . . . 1 . .
H H26 0.5904 0.6587 0.7057 0.046 Uiso calc U . R 1 . .
N N1 0.2399(7) 0.6490(2) 0.5660(2) 0.0269(11) Uani d . . . 1 . .
O O1 0.0890(7) 0.7015(2) 0.5560(2) 0.0404(12) Uani d . . . 1 . .
O O2 0.0551(7) 0.3862(3) 0.5893(2) 0.0491(13) Uani d . . . 1 . .
P P1 0.47574(18) 0.49711(9) 0.73571(6) 0.0200(3) Uani d . . . 1 . .
S S1 0.7828(2) 0.49765(12) 0.72171(8) 0.0416(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.358(7) ?
C1 C2 . 1.365(7) ?
C2 C3 . 1.384(7) ?
C3 C4 . 1.396(7) ?
C4 C5 . 1.382(7) ?
C4 C6 . 1.515(7) ?
C5 N1 . 1.359(6) ?
C6 C7 . 1.537(6) ?
C6 P1 . 1.858(5) ?
C7 C8 . 1.504(7) ?
C8 O2 . 1.213(6) ?
C8 C9 . 1.500(7) ?
C9 C14 . 1.389(8) ?
C9 C10 . 1.406(8) ?
C10 C11 . 1.383(8) ?
C11 C12 . 1.380(9) ?
C12 C13 . 1.381(10) ?
C13 C14 . 1.382(9) ?
C15 C20 . 1.390(8) ?
C15 C16 . 1.391(7) ?
C15 P1 . 1.806(5) ?
C16 C17 . 1.390(9) ?
C17 C18 . 1.375(9) ?
C18 C19 . 1.381(9) ?
C19 C20 . 1.388(8) ?
C21 C22 . 1.382(7) ?
C21 C26 . 1.398(7) ?
C21 P1 . 1.791(5) ?
C22 C23 . 1.398(7) ?
C23 C24 . 1.364(10) ?
C24 C25 . 1.378(10) ?
C25 C26 . 1.375(9) ?
N1 O1 . 1.305(6) ?
P1 S1 . 1.9485(17) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 120.4(5) ?
C1 C2 C3 . . 121.5(5) ?
C2 C3 C4 . . 117.9(5) ?
C5 C4 C3 . . 119.1(5) ?
C5 C4 C6 . . 118.9(5) ?
C3 C4 C6 . . 121.8(4) ?
N1 C5 C4 . . 121.7(5) ?
C4 C6 C7 . . 114.5(4) ?
C4 C6 P1 . . 108.3(3) ?
C7 C6 P1 . . 111.4(3) ?
C8 C7 C6 . . 111.6(4) ?
O2 C8 C9 . . 120.2(5) ?
O2 C8 C7 . . 121.2(5) ?
C9 C8 C7 . . 118.5(5) ?
C14 C9 C10 . . 119.2(5) ?
C14 C9 C8 . . 118.9(5) ?
C10 C9 C8 . . 121.8(5) ?
C11 C10 C9 . . 120.1(6) ?
C12 C11 C10 . . 119.6(7) ?
C11 C12 C13 . . 121.0(6) ?
C12 C13 C14 . . 119.7(7) ?
C13 C14 C9 . . 120.5(6) ?
C20 C15 C16 . . 118.8(5) ?
C20 C15 P1 . . 118.1(4) ?
C16 C15 P1 . . 123.1(5) ?
C17 C16 C15 . . 120.1(6) ?
C18 C17 C16 . . 120.8(6) ?
C17 C18 C19 . . 119.6(6) ?
C18 C19 C20 . . 120.1(6) ?
C19 C20 C15 . . 120.7(6) ?
C22 C21 C26 . . 118.5(5) ?
C22 C21 P1 . . 121.5(4) ?
C26 C21 P1 . . 119.8(4) ?
C21 C22 C23 . . 120.4(6) ?
C24 C23 C22 . . 120.1(7) ?
C23 C24 C25 . . 119.9(6) ?
C26 C25 C24 . . 120.6(6) ?
C25 C26 C21 . . 120.4(6) ?
O1 N1 C1 . . 120.5(4) ?
O1 N1 C5 . . 120.2(5) ?
C1 N1 C5 . . 119.4(5) ?
C21 P1 C15 . . 106.6(2) ?
C21 P1 C6 . . 103.5(2) ?
C15 P1 C6 . . 108.1(2) ?
C21 P1 S1 . . 113.41(19) ?
C15 P1 S1 . . 112.28(19) ?
C6 P1 S1 . . 112.29(17) ?


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DCM/n-hexane
####################################################################### 
# 
# 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_leung928s
_database_code_depnum_ccdc_archive 'CCDC 1472774'
_audit_update_record             
;
2016-04-07 deposited with the CCDC.
2016-07-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 N O2 P S'
_chemical_formula_iupac          ?
_chemical_formula_weight         443.47
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   11.5111(8)
_cell_length_b                   17.2089(8)
_cell_length_c                   22.8522(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4526.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3725
_cell_measurement_theta_min      2.5116
_cell_measurement_theta_max      30.3191
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1856

_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker KappaCCD'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            38273
_diffrn_reflns_av_R_equivalents  0.1471
_diffrn_reflns_av_unetI/netI     0.1775
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         30.63
_diffrn_reflns_theta_full        30.63
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       30

_refine_special_details          
;
;

_reflns_number_total             13895
_reflns_number_gt                7223
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1557
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1461
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_refine_ls_number_reflns         13895
_refine_ls_number_parameters     559
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.429
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 2055 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(8)

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'
N N 0.0061 0.0033 '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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2015)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2015)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.9945(6) 0.5501(3) 0.9020(3) 0.0240(14) Uani d . . . 1 . .
H H1 1.0683 0.5749 0.9026 0.029 Uiso calc U . R 1 . .
C C2 0.9693(7) 0.4910(3) 0.9414(3) 0.0356(17) Uani d . . . 1 . .
H H2 1.0264 0.475 0.9689 0.043 Uiso calc U . R 1 . .
C C3 0.8622(6) 0.4554(3) 0.9409(3) 0.0341(17) Uani d . . . 1 . .
H H3 0.8454 0.4158 0.9686 0.041 Uiso calc U . R 1 . .
C C4 0.7793(5) 0.4768(3) 0.9006(3) 0.0297(15) Uani d . . . 1 . .
H H4 0.7063 0.451 0.9001 0.036 Uiso calc U . R 1 . .
C C5 0.8018(5) 0.5362(3) 0.8605(3) 0.0231(13) Uani d . . . 1 . .
H H5 0.7444 0.5515 0.8329 0.028 Uiso calc U . R 1 . .
C C6 0.9101(5) 0.5726(3) 0.8617(2) 0.0168(11) Uani d . . . 1 . .
C C7 0.9393(5) 0.6348(3) 0.8175(2) 0.0177(12) Uani d . . . 1 . .
C C8 0.8608(5) 0.6407(3) 0.7650(2) 0.0153(11) Uani d . . . 1 . .
H H8A 0.7837 0.6597 0.7778 0.018 Uiso calc U . R 1 . .
H H8B 0.8502 0.5883 0.748 0.018 Uiso calc U . R 1 . .
C C9 0.9081(5) 0.6956(3) 0.7173(2) 0.0138(10) Uani d . . . 1 . .
H H9 0.9922 0.6833 0.7113 0.017 Uiso calc U . R 1 . .
C C10 0.8979(5) 0.7814(3) 0.7300(2) 0.0184(12) Uani d . . . 1 . .
C C11 0.8008(5) 0.8147(3) 0.7564(2) 0.0201(12) Uani d . . . 1 . .
H H11 0.7398 0.7822 0.77 0.024 Uiso calc U . R 1 . .
C C12 0.7917(5) 0.8938(3) 0.7630(3) 0.0235(13) Uani d . . . 1 . .
H H12 0.7254 0.9151 0.7819 0.028 Uiso calc U . R 1 . .
C C13 0.9728(6) 0.9114(3) 0.7179(3) 0.0242(14) Uani d . . . 1 . .
H H13 1.0329 0.9451 0.7049 0.029 Uiso calc U . R 1 . .
C C14 0.9851(5) 0.8321(3) 0.7113(2) 0.0207(12) Uani d . . . 1 . .
H H14 1.0535 0.8118 0.6938 0.025 Uiso calc U . R 1 . .
C C15 0.9083(5) 0.7254(3) 0.5912(2) 0.0163(11) Uani d . . . 1 . .
C C16 0.8462(5) 0.7669(3) 0.5493(3) 0.0210(12) Uani d . . . 1 . .
H H16 0.7645 0.773 0.5532 0.025 Uiso calc U . R 1 . .
C C17 0.9038(6) 0.7995(3) 0.5019(3) 0.0269(13) Uani d . . . 1 . .
H H17 0.8616 0.8277 0.4731 0.032 Uiso calc U . R 1 . .
C C18 1.0226(6) 0.7909(3) 0.4966(3) 0.0279(14) Uani d . . . 1 . .
H H18 1.0618 0.8121 0.4637 0.033 Uiso calc U . R 1 . .
C C19 1.0850(6) 0.7513(3) 0.5393(3) 0.0267(14) Uani d . . . 1 . .
H H19 1.167 0.7469 0.5361 0.032 Uiso calc U . R 1 . .
C C20 1.0284(5) 0.7184(3) 0.5863(2) 0.0199(12) Uani d . . . 1 . .
H H20 1.0712 0.691 0.6152 0.024 Uiso calc U . R 1 . .
C C21 0.8595(5) 0.5732(3) 0.6309(2) 0.0213(13) Uani d . . . 1 . .
C C22 0.7777(6) 0.5328(3) 0.5982(3) 0.0283(14) Uani d . . . 1 . .
H H22 0.7047 0.5559 0.5897 0.034 Uiso calc U . R 1 . .
C C23 0.8026(6) 0.4585(3) 0.5778(3) 0.0334(16) Uani d . . . 1 . .
H H23 0.7475 0.4316 0.5543 0.04 Uiso calc U . R 1 . .
C C24 0.9077(6) 0.4236(3) 0.5915(3) 0.0312(15) Uani d . . . 1 . .
H H24 0.9243 0.3727 0.5778 0.037 Uiso calc U . R 1 . .
C C25 0.9884(5) 0.4627(3) 0.6253(3) 0.0241(13) Uani d . . . 1 . .
H H25 1.0602 0.4387 0.635 0.029 Uiso calc U . R 1 . .
C C26 0.9638(5) 0.5375(3) 0.6450(3) 0.0202(12) Uani d . . . 1 . .
H H26 1.019 0.5643 0.6684 0.024 Uiso calc U . R 1 . .
C C27 0.7335(5) 0.0416(3) 0.9024(2) 0.0201(12) Uani d . . . 1 . .
H H27 0.7999 0.0739 0.9066 0.024 Uiso calc U . R 1 . .
C C28 0.7170(6) -0.0198(3) 0.9409(3) 0.0252(14) Uani d . . . 1 . .
H H28 0.7716 -0.0295 0.9712 0.03 Uiso calc U . R 1 . .
C C29 0.6199(6) -0.0669(3) 0.9347(3) 0.0303(15) Uani d . . . 1 . .
H H29 0.6084 -0.1094 0.9606 0.036 Uiso calc U . R 1 . .
C C30 0.5398(5) -0.0521(3) 0.8908(3) 0.0289(15) Uani d . . . 1 . .
H H30 0.4732 -0.0843 0.8868 0.035 Uiso calc U . R 1 . .
C C31 0.5570(5) 0.0098(3) 0.8526(3) 0.0217(12) Uani d . . . 1 . .
H H31 0.5019 0.0203 0.8227 0.026 Uiso calc U . R 1 . .
C C32 0.6551(5) 0.0564(3) 0.8583(2) 0.0167(11) Uani d . . . 1 . .
C C33 0.6817(5) 0.1199(3) 0.8148(2) 0.0168(11) Uani d . . . 1 . .
C C34 0.6057(5) 0.1245(3) 0.7611(2) 0.0168(11) Uani d . . . 1 . .
H H34A 0.5274 0.1426 0.7726 0.02 Uiso calc U . R 1 . .
H H34B 0.5976 0.0719 0.7439 0.02 Uiso calc U . R 1 . .
C C35 0.6552(5) 0.1798(3) 0.7147(2) 0.0155(11) Uani d . . . 1 . .
H H35 0.7378 0.1651 0.707 0.019 Uiso calc U . R 1 . .
C C36 0.6509(5) 0.2656(3) 0.7300(2) 0.0156(11) Uani d . . . 1 . .
C C37 0.5579(5) 0.2989(3) 0.7597(2) 0.0201(12) Uani d . . . 1 . .
H H37 0.4965 0.267 0.7736 0.024 Uiso calc U . R 1 . .
C C38 0.5542(5) 0.3776(3) 0.7692(3) 0.0234(13) Uani d . . . 1 . .
H H38 0.4905 0.399 0.7901 0.028 Uiso calc U . R 1 . .
C C39 0.7310(5) 0.3944(3) 0.7217(3) 0.0230(13) Uani d . . . 1 . .
H H39 0.7917 0.4274 0.7083 0.028 Uiso calc U . R 1 . .
C C40 0.7389(5) 0.3153(3) 0.7124(2) 0.0193(12) Uani d . . . 1 . .
H H40 0.8057 0.2946 0.6935 0.023 Uiso calc U . R 1 . .
C C41 0.6492(5) 0.2199(3) 0.5896(2) 0.0151(11) Uani d . . . 1 . .
C C42 0.5879(5) 0.2655(3) 0.5501(2) 0.0190(12) Uani d . . . 1 . .
H H42 0.5071 0.2742 0.5555 0.023 Uiso calc U . R 1 . .
C C43 0.6453(5) 0.2984(3) 0.5024(3) 0.0255(13) Uani d . . . 1 . .
H H43 0.6035 0.3297 0.4754 0.031 Uiso calc U . R 1 . .
C C44 0.7623(6) 0.2856(3) 0.4944(3) 0.0251(14) Uani d . . . 1 . .
H H44 0.8009 0.3067 0.4613 0.03 Uiso calc U . R 1 . .
C C45 0.8237(5) 0.2419(3) 0.5352(3) 0.0197(12) Uani d . . . 1 . .
H H45 0.905 0.2348 0.5305 0.024 Uiso calc U . R 1 . .
C C46 0.7682(5) 0.2086(3) 0.5822(3) 0.0203(12) Uani d . . . 1 . .
H H46 0.8106 0.178 0.6094 0.024 Uiso calc U . R 1 . .
C C47 0.5894(5) 0.0673(3) 0.6212(2) 0.0179(12) Uani d . . . 1 . .
C C48 0.5111(5) 0.0404(3) 0.5797(3) 0.0241(14) Uani d . . . 1 . .
H H48 0.4474 0.072 0.5682 0.029 Uiso calc U . R 1 . .
C C49 0.5254(6) -0.0326(3) 0.5549(3) 0.0293(15) Uani d . . . 1 . .
H H49 0.4729 -0.0502 0.5257 0.035 Uiso calc U . R 1 . .
C C50 0.6165(6) -0.0799(3) 0.5728(3) 0.0302(15) Uani d . . . 1 . .
H H50 0.6252 -0.1304 0.5566 0.036 Uiso calc U . R 1 . .
C C51 0.6939(5) -0.0535(3) 0.6140(3) 0.0259(14) Uani d . . . 1 . .
H H51 0.7561 -0.0861 0.6261 0.031 Uiso calc U . R 1 . .
C C52 0.6823(5) 0.0205(3) 0.6383(2) 0.0202(12) Uani d . . . 1 . .
H H52 0.7371 0.0388 0.6662 0.024 Uiso calc U . R 1 . .
N N1 0.8766(5) 0.9419(2) 0.7428(2) 0.0229(11) Uani d . . . 1 . .
N N2 0.6389(5) 0.4258(2) 0.7495(2) 0.0225(11) Uani d . . . 1 . .
O O1 1.0237(4) 0.6766(2) 0.82359(19) 0.0293(10) Uani d . . . 1 . .
O O2 0.8645(4) 1.01773(18) 0.7477(2) 0.0298(10) Uani d . . . 1 . .
O O3 0.7636(4) 0.16383(19) 0.82218(17) 0.0249(9) Uani d . . . 1 . .
O O4 0.6300(4) 0.50085(19) 0.7562(2) 0.0341(11) Uani d . . . 1 . .
P P1 0.83034(12) 0.67409(7) 0.64840(7) 0.0151(3) Uani d . . . 1 . .
P P2 0.57103(11) 0.16706(7) 0.64620(7) 0.0137(3) Uani d . . . 1 . .
S S1 0.66538(12) 0.70002(7) 0.65091(7) 0.0217(3) Uani d . . . 1 . .
S S2 0.40888(11) 0.19945(7) 0.65234(7) 0.0182(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.389(8) ?
C1 C6 . 1.394(8) ?
C2 C3 . 1.377(10) ?
C3 C4 . 1.376(9) ?
C4 C5 . 1.398(7) ?
C5 C6 . 1.395(8) ?
C6 C7 . 1.511(7) ?
C7 O1 . 1.216(6) ?
C7 C8 . 1.505(7) ?
C8 C9 . 1.542(7) ?
C9 C10 . 1.508(7) ?
C9 P1 . 1.849(5) ?
C10 C11 . 1.393(8) ?
C10 C14 . 1.397(7) ?
C11 C12 . 1.373(7) ?
C12 N1 . 1.362(7) ?
C13 N1 . 1.350(8) ?
C13 C14 . 1.382(7) ?
C15 C16 . 1.392(8) ?
C15 C20 . 1.392(8) ?
C15 P1 . 1.814(5) ?
C16 C17 . 1.390(8) ?
C17 C18 . 1.380(9) ?
C18 C19 . 1.390(9) ?
C19 C20 . 1.377(8) ?
C21 C22 . 1.389(8) ?
C21 C26 . 1.387(8) ?
C21 P1 . 1.813(5) ?
C22 C23 . 1.391(7) ?
C23 C24 . 1.388(9) ?
C24 C25 . 1.383(8) ?
C25 C26 . 1.392(7) ?
C27 C32 . 1.377(8) ?
C27 C28 . 1.388(7) ?
C28 C29 . 1.387(8) ?
C29 C30 . 1.386(8) ?
C30 C31 . 1.392(7) ?
C31 C32 . 1.391(7) ?
C32 C33 . 1.508(7) ?
C33 O3 . 1.220(6) ?
C33 C34 . 1.509(7) ?
C34 C35 . 1.534(7) ?
C35 C36 . 1.519(7) ?
C35 P2 . 1.854(5) ?
C36 C40 . 1.386(7) ?
C36 C37 . 1.391(7) ?
C37 C38 . 1.371(7) ?
C38 N2 . 1.357(7) ?
C39 N2 . 1.349(8) ?
C39 C40 . 1.382(7) ?
C41 C42 . 1.390(7) ?
C41 C46 . 1.394(8) ?
C41 P2 . 1.819(5) ?
C42 C43 . 1.393(8) ?
C43 C44 . 1.378(9) ?
C44 C45 . 1.390(8) ?
C45 C46 . 1.375(8) ?
C47 C48 . 1.387(8) ?
C47 C52 . 1.395(7) ?
C47 P2 . 1.822(5) ?
C48 C49 . 1.387(7) ?
C49 C50 . 1.389(9) ?
C50 C51 . 1.372(9) ?
C51 C52 . 1.397(7) ?
N1 O2 . 1.317(5) ?
N2 O4 . 1.305(5) ?
P1 S1 . 1.952(2) ?
P2 S2 . 1.9530(19) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 119.0(6) ?
C3 C2 C1 . . 120.5(6) ?
C2 C3 C4 . . 120.5(6) ?
C3 C4 C5 . . 120.4(6) ?
C4 C5 C6 . . 118.7(6) ?
C5 C6 C1 . . 120.8(5) ?
C5 C6 C7 . . 120.3(5) ?
C1 C6 C7 . . 118.9(5) ?
O1 C7 C8 . . 122.0(5) ?
O1 C7 C6 . . 121.4(5) ?
C8 C7 C6 . . 116.6(5) ?
C7 C8 C9 . . 113.1(4) ?
C10 C9 C8 . . 115.8(4) ?
C10 C9 P1 . . 108.8(3) ?
C8 C9 P1 . . 108.0(3) ?
C11 C10 C14 . . 116.9(5) ?
C11 C10 C9 . . 123.3(5) ?
C14 C10 C9 . . 119.7(5) ?
C12 C11 C10 . . 121.1(5) ?
N1 C12 C11 . . 120.7(6) ?
N1 C13 C14 . . 121.0(5) ?
C13 C14 C10 . . 120.7(6) ?
C16 C15 C20 . . 119.9(5) ?
C16 C15 P1 . . 119.4(4) ?
C20 C15 P1 . . 120.5(4) ?
C15 C16 C17 . . 119.9(6) ?
C18 C17 C16 . . 119.8(6) ?
C17 C18 C19 . . 120.2(6) ?
C20 C19 C18 . . 120.3(6) ?
C19 C20 C15 . . 119.8(6) ?
C22 C21 C26 . . 119.4(5) ?
C22 C21 P1 . . 118.2(5) ?
C26 C21 P1 . . 122.2(4) ?
C23 C22 C21 . . 120.1(6) ?
C22 C23 C24 . . 120.1(6) ?
C25 C24 C23 . . 120.1(5) ?
C24 C25 C26 . . 119.6(6) ?
C21 C26 C25 . . 120.7(5) ?
C32 C27 C28 . . 121.0(5) ?
C27 C28 C29 . . 119.4(6) ?
C30 C29 C28 . . 120.1(5) ?
C29 C30 C31 . . 120.0(6) ?
C32 C31 C30 . . 119.9(5) ?
C27 C32 C31 . . 119.6(5) ?
C27 C32 C33 . . 118.9(5) ?
C31 C32 C33 . . 121.4(5) ?
O3 C33 C32 . . 121.0(5) ?
O3 C33 C34 . . 121.8(5) ?
C32 C33 C34 . . 117.2(5) ?
C33 C34 C35 . . 112.3(4) ?
C36 C35 C34 . . 115.5(4) ?
C36 C35 P2 . . 107.0(3) ?
C34 C35 P2 . . 108.5(3) ?
C40 C36 C37 . . 116.8(4) ?
C40 C36 C35 . . 120.5(5) ?
C37 C36 C35 . . 122.6(5) ?
C38 C37 C36 . . 120.5(5) ?
N2 C38 C37 . . 121.9(5) ?
N2 C39 C40 . . 121.3(5) ?
C39 C40 C36 . . 120.9(5) ?
C42 C41 C46 . . 119.9(5) ?
C42 C41 P2 . . 119.6(4) ?
C46 C41 P2 . . 120.2(4) ?
C41 C42 C43 . . 119.8(5) ?
C44 C43 C42 . . 120.2(6) ?
C43 C44 C45 . . 119.6(6) ?
C46 C45 C44 . . 120.8(5) ?
C45 C46 C41 . . 119.6(5) ?
C48 C47 C52 . . 119.8(5) ?
C48 C47 P2 . . 117.0(4) ?
C52 C47 P2 . . 123.0(4) ?
C49 C48 C47 . . 120.3(5) ?
C48 C49 C50 . . 119.9(6) ?
C51 C50 C49 . . 119.9(5) ?
C50 C51 C52 . . 120.8(5) ?
C47 C52 C51 . . 119.2(5) ?
O2 N1 C13 . . 120.5(5) ?
O2 N1 C12 . . 119.9(5) ?
C13 N1 C12 . . 119.6(4) ?
O4 N2 C39 . . 120.9(5) ?
O4 N2 C38 . . 120.6(5) ?
C39 N2 C38 . . 118.5(4) ?
C21 P1 C15 . . 102.5(2) ?
C21 P1 C9 . . 106.9(2) ?
C15 P1 C9 . . 106.0(2) ?
C21 P1 S1 . . 113.9(2) ?
C15 P1 S1 . . 113.02(19) ?
C9 P1 S1 . . 113.59(18) ?
C41 P2 C47 . . 101.0(2) ?
C41 P2 C35 . . 106.4(2) ?
C47 P2 C35 . . 108.4(2) ?
C41 P2 S2 . . 112.42(18) ?
C47 P2 S2 . . 113.72(19) ?
C35 P2 S2 . . 113.90(19) ?


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DCM/n-hexane
