# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_compound-5
_database_code_depnum_ccdc_archive 'CCDC 1041550'
_audit_update_record             
;
2014-12-30 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H29 N O3 P2'
_chemical_formula_weight         621.57

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'

_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                   11.2790(6)
_cell_length_b                   16.1962(8)
_cell_length_c                   17.5843(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3212.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4805
_cell_measurement_theta_min      2.9317
_cell_measurement_theta_max      28.7963

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9593
_exptl_absorpt_correction_T_max  0.9759
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8256
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5347
_reflns_number_gt                4682
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0650P)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   -0.03(9)
_refine_ls_number_reflns         5347
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
P1 P 0.44769(6) 1.08184(4) 0.89306(4) 0.03293(18) Uani 1 1 d . . .
P2 P 0.12832(6) 0.87882(4) 0.90334(4) 0.03580(18) Uani 1 1 d . . .
C28 C 0.2492(2) 0.81500(16) 0.86795(16) 0.0358(6) Uani 1 1 d . . .
C21 C 0.1475(2) 0.97606(17) 0.84830(14) 0.0317(6) Uani 1 1 d . . .
C19 C 0.3647(2) 1.02413(16) 0.82159(14) 0.0319(6) Uani 1 1 d . . .
C1 C 0.5040(2) 1.00693(17) 0.96024(16) 0.0380(7) Uani 1 1 d . . .
O1 O 0.54152(18) 1.13246(13) 0.85824(11) 0.0474(5) Uani 1 1 d . . .
C20 C 0.2534(2) 1.00294(17) 0.83478(14) 0.0323(6) Uani 1 1 d . . .
C29 C 0.2890(3) 0.81384(19) 0.79322(18) 0.0446(7) Uani 1 1 d . . .
H29 H 0.2536 0.8481 0.7574 0.054 Uiso 1 1 calc R . .
C33 C 0.3043(3) 0.7637(2) 0.9216(2) 0.0530(8) Uani 1 1 d . . .
H33 H 0.2810 0.7649 0.9723 0.064 Uiso 1 1 calc R . .
C22 C -0.0062(2) 0.83326(17) 0.86162(16) 0.0374(6) Uani 1 1 d . . .
N1 N -0.0198(3) 0.95854(19) 0.71588(16) 0.0581(7) Uani 1 1 d . . .
C35 C -0.0416(3) 1.01796(18) 0.77714(17) 0.0436(7) Uani 1 1 d . . .
C18 C 0.3693(3) 1.0179(2) 0.67940(17) 0.0570(9) Uani 1 1 d . . .
H18 H 0.2952 1.0430 0.6783 0.068 Uiso 1 1 calc R . .
O2 O 0.0821(2) 0.9438(2) 0.69821(14) 0.0794(9) Uani 1 1 d . . .
C34 C 0.0401(2) 1.02782(16) 0.83633(16) 0.0351(6) Uani 1 1 d . . .
C7 C 0.3395(2) 1.14383(17) 0.94266(15) 0.0370(7) Uani 1 1 d . . .
C4 C 0.5948(4) 0.8974(2) 1.0664(2) 0.0624(10) Uani 1 1 d . . .
H4 H 0.6259 0.8607 1.1018 0.075 Uiso 1 1 calc R . .
C23 C -0.1139(3) 0.8580(2) 0.89275(18) 0.0507(8) Uani 1 1 d . . .
H23 H -0.1151 0.8979 0.9308 0.061 Uiso 1 1 calc R . .
C13 C 0.4247(2) 1.00292(18) 0.74837(15) 0.0385(7) Uani 1 1 d . . .
C30 C 0.3796(3) 0.7628(2) 0.7718(2) 0.0545(9) Uani 1 1 d . . .
H30 H 0.4067 0.7638 0.7219 0.065 Uiso 1 1 calc R . .
C39 C 0.0130(3) 1.08609(19) 0.89164(17) 0.0452(7) Uani 1 1 d . . .
H39 H 0.0654 1.0940 0.9318 0.054 Uiso 1 1 calc R . .
C36 C -0.1468(3) 1.0623(2) 0.7746(2) 0.0585(9) Uani 1 1 d . . .
H36 H -0.2014 1.0534 0.7357 0.070 Uiso 1 1 calc R . .
C12 C 0.3092(3) 1.1325(2) 1.01880(16) 0.0514(8) Uani 1 1 d . . .
H12 H 0.3450 1.0908 1.0471 0.062 Uiso 1 1 calc R . .
C26 C -0.1120(3) 0.7386(2) 0.7811(2) 0.0642(10) Uani 1 1 d . . .
H26 H -0.1113 0.6982 0.7435 0.077 Uiso 1 1 calc R . .
C24 C -0.2193(3) 0.8238(3) 0.8674(2) 0.0639(10) Uani 1 1 d . . .
H24 H -0.2911 0.8415 0.8878 0.077 Uiso 1 1 calc R . .
C10 C 0.1738(3) 1.2461(3) 1.0112(3) 0.0706(12) Uani 1 1 d . . .
H10 H 0.1172 1.2798 1.0338 0.085 Uiso 1 1 calc R . .
C8 C 0.2872(3) 1.20835(19) 0.90282(19) 0.0544(8) Uani 1 1 d . . .
H8 H 0.3078 1.2175 0.8523 0.065 Uiso 1 1 calc R . .
C38 C -0.0895(3) 1.1326(2) 0.8888(2) 0.0641(10) Uani 1 1 d . . .
H38 H -0.1045 1.1723 0.9259 0.077 Uiso 1 1 calc R . .
C3 C 0.6647(3) 0.9558(3) 1.0354(2) 0.0658(10) Uani 1 1 d . . .
H3 H 0.7438 0.9587 1.0499 0.079 Uiso 1 1 calc R . .
C5 C 0.4781(4) 0.8921(2) 1.0459(2) 0.0731(11) Uani 1 1 d . . .
H5 H 0.4292 0.8527 1.0681 0.088 Uiso 1 1 calc R . .
C37 C -0.1690(3) 1.1200(3) 0.8309(2) 0.0673(11) Uani 1 1 d . . .
H37 H -0.2387 1.1506 0.8295 0.081 Uiso 1 1 calc R . .
C14 C 0.5355(3) 0.9655(3) 0.7488(2) 0.0643(10) Uani 1 1 d . . .
H14 H 0.5739 0.9546 0.7945 0.077 Uiso 1 1 calc R . .
C31 C 0.4312(3) 0.7099(2) 0.8237(3) 0.0662(10) Uani 1 1 d . . .
H31 H 0.4905 0.6737 0.8082 0.079 Uiso 1 1 calc R . .
C25 C -0.2181(3) 0.7637(3) 0.8122(2) 0.0701(11) Uani 1 1 d . . .
H25 H -0.2888 0.7400 0.7959 0.084 Uiso 1 1 calc R . .
C17 C 0.4245(5) 0.9953(3) 0.6118(2) 0.0870(15) Uani 1 1 d . . .
H17 H 0.3875 1.0054 0.5655 0.104 Uiso 1 1 calc R . .
O3 O -0.1051(3) 0.92653(18) 0.68515(16) 0.0889(9) Uani 1 1 d . . .
C27 C -0.0067(3) 0.7732(2) 0.80531(18) 0.0478(8) Uani 1 1 d . . .
H27 H 0.0644 0.7561 0.7837 0.057 Uiso 1 1 calc R . .
C2 C 0.6216(3) 1.0122(2) 0.98203(18) 0.0528(8) Uani 1 1 d . . .
H2 H 0.6710 1.0525 0.9616 0.063 Uiso 1 1 calc R . .
C32 C 0.3951(3) 0.7108(2) 0.8976(3) 0.0689(10) Uani 1 1 d . . .
H32 H 0.4311 0.6759 0.9326 0.083 Uiso 1 1 calc R . .
C9 C 0.2053(4) 1.2588(2) 0.9375(3) 0.0719(11) Uani 1 1 d . . .
H9 H 0.1711 1.3019 0.9102 0.086 Uiso 1 1 calc R . .
C6 C 0.4330(3) 0.9463(2) 0.99167(19) 0.0592(9) Uani 1 1 d . . .
H6 H 0.3543 0.9417 0.9764 0.071 Uiso 1 1 calc R . .
C11 C 0.2253(4) 1.1837(2) 1.0522(2) 0.0697(11) Uani 1 1 d . . .
H11 H 0.2039 1.1756 1.1028 0.084 Uiso 1 1 calc R . .
C16 C 0.5324(4) 0.9585(4) 0.6135(3) 0.1009(18) Uani 1 1 d . . .
H16 H 0.5687 0.9427 0.5683 0.121 Uiso 1 1 calc R . .
C15 C 0.5877(3) 0.9445(3) 0.6805(3) 0.0890(16) Uani 1 1 d . . .
H15 H 0.6625 0.9203 0.6806 0.107 Uiso 1 1 calc R . .


_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(2) . ?
P1 C7 1.805(3) . ?
P1 C1 1.809(3) . ?
P1 C19 1.825(3) . ?
P2 C28 1.820(3) . ?
P2 C22 1.840(3) . ?
P2 C21 1.861(3) . ?
C28 C29 1.389(4) . ?
C28 C33 1.402(4) . ?
C21 C20 1.293(4) . ?
C21 C34 1.488(4) . ?
C19 C20 1.322(4) . ?
C19 C13 1.495(4) . ?
C1 C6 1.383(4) . ?
C1 C2 1.383(4) . ?
C29 C30 1.367(4) . ?
C29 H29 0.9300 . ?
C33 C32 1.400(5) . ?
C33 H33 0.9300 . ?
C22 C27 1.388(4) . ?
C22 C23 1.392(4) . ?
N1 O2 1.215(4) . ?
N1 O3 1.219(4) . ?
N1 C35 1.465(4) . ?
C35 C36 1.387(4) . ?
C35 C34 1.400(4) . ?
C18 C13 1.385(4) . ?
C18 C17 1.391(5) . ?
C18 H18 0.9300 . ?
C34 C39 1.389(4) . ?
C7 C8 1.390(4) . ?
C7 C12 1.394(4) . ?
C4 C3 1.346(5) . ?
C4 C5 1.368(5) . ?
C4 H4 0.9300 . ?
C23 C24 1.386(5) . ?
C23 H23 0.9300 . ?
C13 C14 1.389(4) . ?
C30 C31 1.381(5) . ?
C30 H30 0.9300 . ?
C39 C38 1.381(4) . ?
C39 H39 0.9300 . ?
C36 C37 1.385(5) . ?
C36 H36 0.9300 . ?
C12 C11 1.389(5) . ?
C12 H12 0.9300 . ?
C26 C25 1.377(5) . ?
C26 C27 1.381(5) . ?
C26 H26 0.9300 . ?
C24 C25 1.375(6) . ?
C24 H24 0.9300 . ?
C10 C9 1.360(6) . ?
C10 C11 1.370(6) . ?
C10 H10 0.9300 . ?
C8 C9 1.375(5) . ?
C8 H8 0.9300 . ?
C38 C37 1.372(5) . ?
C38 H38 0.9300 . ?
C3 C2 1.397(5) . ?
C3 H3 0.9300 . ?
C5 C6 1.392(5) . ?
C5 H5 0.9300 . ?
C37 H37 0.9300 . ?
C14 C15 1.380(5) . ?
C14 H14 0.9300 . ?
C31 C32 1.362(5) . ?
C31 H31 0.9300 . ?
C25 H25 0.9300 . ?
C17 C16 1.355(7) . ?
C17 H17 0.9300 . ?
C27 H27 0.9300 . ?
C2 H2 0.9300 . ?
C32 H32 0.9300 . ?
C9 H9 0.9300 . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C16 C15 1.352(6) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?

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 112.15(13) . . ?
O1 P1 C1 113.12(13) . . ?
C7 P1 C1 107.16(13) . . ?
O1 P1 C19 111.57(12) . . ?
C7 P1 C19 105.72(13) . . ?
C1 P1 C19 106.65(13) . . ?
C28 P2 C22 104.68(13) . . ?
C28 P2 C21 102.46(12) . . ?
C22 P2 C21 103.16(12) . . ?
C29 C28 C33 119.0(3) . . ?
C29 C28 P2 125.0(2) . . ?
C33 C28 P2 116.0(2) . . ?
C20 C21 C34 122.4(3) . . ?
C20 C21 P2 119.2(2) . . ?
C34 C21 P2 117.12(18) . . ?
C20 C19 C13 121.4(2) . . ?
C20 C19 P1 120.0(2) . . ?
C13 C19 P1 118.61(19) . . ?
C6 C1 C2 119.3(3) . . ?
C6 C1 P1 122.3(2) . . ?
C2 C1 P1 118.5(2) . . ?
C21 C20 C19 175.3(3) . . ?
C30 C29 C28 120.7(3) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C32 C33 C28 119.0(3) . . ?
C32 C33 H33 120.5 . . ?
C28 C33 H33 120.5 . . ?
C27 C22 C23 118.6(3) . . ?
C27 C22 P2 124.7(2) . . ?
C23 C22 P2 116.6(2) . . ?
O2 N1 O3 123.4(3) . . ?
O2 N1 C35 118.4(3) . . ?
O3 N1 C35 118.2(3) . . ?
C36 C35 C34 121.9(3) . . ?
C36 C35 N1 117.3(3) . . ?
C34 C35 N1 120.7(3) . . ?
C13 C18 C17 120.0(4) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C39 C34 C35 116.9(3) . . ?
C39 C34 C21 117.6(2) . . ?
C35 C34 C21 125.2(3) . . ?
C8 C7 C12 118.6(3) . . ?
C8 C7 P1 117.5(2) . . ?
C12 C7 P1 123.8(2) . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C18 C13 C14 119.1(3) . . ?
C18 C13 C19 120.7(3) . . ?
C14 C13 C19 120.2(3) . . ?
C29 C30 C31 120.6(3) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C38 C39 C34 122.0(3) . . ?
C38 C39 H39 119.0 . . ?
C34 C39 H39 119.0 . . ?
C37 C36 C35 118.7(3) . . ?
C37 C36 H36 120.7 . . ?
C35 C36 H36 120.7 . . ?
C11 C12 C7 119.7(3) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C37 C38 C39 119.4(4) . . ?
C37 C38 H38 120.3 . . ?
C39 C38 H38 120.3 . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C4 C5 C6 119.5(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C38 C37 C36 121.0(3) . . ?
C38 C37 H37 119.5 . . ?
C36 C37 H37 119.5 . . ?
C15 C14 C13 119.1(4) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C32 C31 C30 119.8(3) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C24 C25 C26 119.9(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C16 C17 C18 119.9(4) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C26 C27 C22 120.6(3) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C31 C32 C33 120.9(3) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C15 C16 C17 120.5(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C15 C14 121.3(4) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.040
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_compound-6
_database_code_depnum_ccdc_archive 'CCDC 1041551'
_audit_update_record             
;
2014-12-30 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H29 N O4 P2'
_chemical_formula_weight         637.57

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'

_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                   11.2810(5)
_cell_length_b                   16.1001(8)
_cell_length_c                   17.7437(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3222.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3783
_cell_measurement_theta_min      2.6160
_cell_measurement_theta_max      28.8885

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9652
_exptl_absorpt_correction_T_max  0.9755
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            12778
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_sigmaI/netI    0.1083
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5547
_reflns_number_gt                3681
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0338P)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    mixed
_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   -0.09(12)
_refine_ls_number_reflns         5547
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_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
P1 P 0.04730(9) 1.07925(7) 0.89717(6) 0.0339(3) Uani 1 1 d . . .
P2 P 0.36507(10) 0.87545(7) 0.89680(6) 0.0358(3) Uani 1 1 d . . .
C19 C 0.1280(4) 1.0215(3) 0.8253(2) 0.0324(10) Uani 1 1 d . . .
O1 O -0.0470(3) 1.12986(18) 0.86249(13) 0.0451(8) Uani 1 1 d . . .
O2 O 0.3709(3) 0.8868(2) 0.97964(14) 0.0554(9) Uani 1 1 d . . .
C22 C 0.2429(4) 0.8133(3) 0.8655(2) 0.0338(10) Uani 1 1 d . . .
C20 C 0.2400(4) 1.0015(3) 0.83667(18) 0.0299(10) Uani 1 1 d . . .
C35 C 0.5354(4) 1.0187(3) 0.7782(2) 0.0452(12) Uani 1 1 d . . .
C21 C 0.3475(4) 0.9748(3) 0.84757(19) 0.0317(10) Uani 1 1 d . . .
C23 C 0.2071(4) 0.8088(3) 0.7911(2) 0.0422(12) Uani 1 1 d . . .
H23 H 0.2461 0.8404 0.7549 0.051 Uiso 1 1 calc R . .
C1 C -0.0083(4) 1.0045(3) 0.9641(2) 0.0364(11) Uani 1 1 d . . .
C7 C 0.1582(3) 1.1424(3) 0.9437(2) 0.0363(11) Uani 1 1 d . . .
C14 C 0.1201(5) 1.0134(3) 0.6849(2) 0.0575(14) Uani 1 1 d . . .
H14 H 0.1932 1.0398 0.6820 0.069 Uiso 1 1 calc R . .
C34 C 0.4557(4) 1.0268(3) 0.8358(2) 0.0374(11) Uani 1 1 d . . .
C13 C 0.0650(4) 0.9987(3) 0.7544(2) 0.0364(11) Uani 1 1 d . . .
C28 C 0.5004(4) 0.8300(3) 0.8597(2) 0.0370(11) Uani 1 1 d . . .
C33 C 0.5032(4) 0.7747(3) 0.8003(2) 0.0486(13) Uani 1 1 d . . .
H33 H 0.4334 0.7602 0.7757 0.058 Uiso 1 1 calc R . .
C39 C 0.4844(4) 1.0829(3) 0.8920(3) 0.0519(12) Uani 1 1 d . . .
H39 H 0.4334 1.0898 0.9327 0.062 Uiso 1 1 calc R . .
C27 C 0.1842(4) 0.7649(3) 0.9189(3) 0.0531(13) Uani 1 1 d . . .
H27 H 0.2070 0.7667 0.9692 0.064 Uiso 1 1 calc R . .
C29 C 0.6067(4) 0.8511(3) 0.8943(3) 0.0522(13) Uani 1 1 d . . .
H29 H 0.6063 0.8886 0.9342 0.063 Uiso 1 1 calc R . .
C4 C -0.1001(5) 0.8941(3) 1.0686(3) 0.0663(16) Uani 1 1 d . . .
H4 H -0.1305 0.8573 1.1040 0.080 Uiso 1 1 calc R . .
C36 C 0.6401(4) 1.0631(3) 0.7750(3) 0.0623(15) Uani 1 1 d . . .
H36 H 0.6922 1.0556 0.7349 0.075 Uiso 1 1 calc R . .
C12 C 0.1920(4) 1.1324(3) 1.0182(2) 0.0529(13) Uani 1 1 d . . .
H12 H 0.1593 1.0899 1.0471 0.063 Uiso 1 1 calc R . .
C2 C 0.0656(4) 0.9466(3) 0.9987(2) 0.0530(13) Uani 1 1 d . . .
H2 H 0.1459 0.9451 0.9870 0.064 Uiso 1 1 calc R . .
C26 C 0.0903(4) 0.7136(3) 0.8961(4) 0.0694(16) Uani 1 1 d . . .
H26 H 0.0495 0.6818 0.9314 0.083 Uiso 1 1 calc R . .
N1 N 0.5120(5) 0.9604(3) 0.7155(2) 0.0723(15) Uani 1 1 d . . .
C30 C 0.7118(4) 0.8180(4) 0.8709(3) 0.0646(16) Uani 1 1 d . . .
H30 H 0.7821 0.8330 0.8947 0.078 Uiso 1 1 calc R . .
C6 C -0.1276(4) 1.0073(3) 0.9824(2) 0.0496(12) Uani 1 1 d . . .
H6 H -0.1768 1.0466 0.9601 0.060 Uiso 1 1 calc R . .
C8 C 0.2069(4) 1.2068(3) 0.9031(3) 0.0574(14) Uani 1 1 d . . .
H8 H 0.1833 1.2148 0.8535 0.069 Uiso 1 1 calc R . .
C3 C 0.0188(5) 0.8917(3) 1.0505(2) 0.0616(15) Uani 1 1 d . . .
H3 H 0.0678 0.8526 1.0733 0.074 Uiso 1 1 calc R . .
C32 C 0.6107(5) 0.7406(3) 0.7772(3) 0.0654(15) Uani 1 1 d . . .
H32 H 0.6126 0.7026 0.7377 0.079 Uiso 1 1 calc R . .
C18 C -0.0437(4) 0.9600(3) 0.7569(2) 0.0599(14) Uani 1 1 d . . .
H18 H -0.0800 0.9503 0.8032 0.072 Uiso 1 1 calc R . .
C17 C -0.0993(5) 0.9356(4) 0.6912(3) 0.085(2) Uani 1 1 d . . .
H17 H -0.1732 0.9101 0.6932 0.102 Uiso 1 1 calc R . .
C24 C 0.1141(5) 0.7580(3) 0.7699(3) 0.0582(14) Uani 1 1 d . . .
H24 H 0.0894 0.7568 0.7199 0.070 Uiso 1 1 calc R . .
O4 O 0.4089(4) 0.9454(3) 0.6981(2) 0.0991(16) Uani 1 1 d . . .
C9 C 0.2898(5) 1.2597(4) 0.9342(3) 0.0758(17) Uani 1 1 d . . .
H9 H 0.3219 1.3028 0.9059 0.091 Uiso 1 1 calc R . .
C16 C -0.0458(6) 0.9490(4) 0.6234(3) 0.089(2) Uani 1 1 d . . .
H16 H -0.0829 0.9319 0.5793 0.106 Uiso 1 1 calc R . .
O3 O 0.5955(4) 0.9302(3) 0.6804(2) 0.1079(16) Uani 1 1 d . . .
C37 C 0.6660(4) 1.1175(4) 0.8307(3) 0.0698(16) Uani 1 1 d . . .
H37 H 0.7368 1.1472 0.8296 0.084 Uiso 1 1 calc R . .
C31 C 0.7138(5) 0.7631(4) 0.8127(3) 0.0750(17) Uani 1 1 d . . .
H31 H 0.7855 0.7406 0.7969 0.090 Uiso 1 1 calc R . .
C25 C 0.0592(5) 0.7104(3) 0.8216(3) 0.0664(15) Uani 1 1 d . . .
H25 H -0.0009 0.6746 0.8064 0.080 Uiso 1 1 calc R . .
C38 C 0.5876(5) 1.1288(4) 0.8887(3) 0.0713(16) Uani 1 1 d . . .
H38 H 0.6040 1.1676 0.9261 0.086 Uiso 1 1 calc R . .
C10 C 0.3239(5) 1.2477(4) 1.0071(4) 0.0729(18) Uani 1 1 d . . .
H10 H 0.3812 1.2821 1.0283 0.087 Uiso 1 1 calc R . .
C5 C -0.1736(5) 0.9508(4) 1.0345(3) 0.0640(15) Uani 1 1 d . . .
H5 H -0.2540 0.9516 1.0461 0.077 Uiso 1 1 calc R . .
C15 C 0.0610(6) 0.9870(4) 0.6199(3) 0.0730(18) Uani 1 1 d . . .
H15 H 0.0960 0.9957 0.5731 0.088 Uiso 1 1 calc R . .
C11 C 0.2743(5) 1.1856(4) 1.0495(3) 0.0742(18) Uani 1 1 d . . .
H11 H 0.2964 1.1792 1.0996 0.089 Uiso 1 1 calc R . .


_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 1.474(3) . ?
P1 C1 1.804(4) . ?
P1 C7 1.812(4) . ?
P1 C19 1.821(4) . ?
P2 O2 1.483(3) . ?
P2 C22 1.792(4) . ?
P2 C28 1.816(4) . ?
P2 C21 1.834(4) . ?
C19 C20 1.319(6) . ?
C19 C13 1.492(5) . ?
C22 C23 1.382(5) . ?
C22 C27 1.393(5) . ?
C20 C21 1.300(6) . ?
C35 C34 1.367(5) . ?
C35 C36 1.382(6) . ?
C35 N1 1.479(6) . ?
C21 C34 1.495(5) . ?
C23 C24 1.383(6) . ?
C23 H23 0.9300 . ?
C1 C6 1.386(6) . ?
C1 C2 1.392(6) . ?
C7 C8 1.376(5) . ?
C7 C12 1.385(5) . ?
C14 C15 1.397(7) . ?
C14 C13 1.401(5) . ?
C14 H14 0.9300 . ?
C34 C39 1.385(6) . ?
C13 C18 1.376(6) . ?
C28 C33 1.381(5) . ?
C28 C29 1.390(5) . ?
C33 C32 1.393(6) . ?
C33 H33 0.9300 . ?
C39 C38 1.379(6) . ?
C39 H39 0.9300 . ?
C27 C26 1.403(6) . ?
C27 H27 0.9300 . ?
C29 C30 1.365(6) . ?
C29 H29 0.9300 . ?
C4 C5 1.374(6) . ?
C4 C3 1.380(6) . ?
C4 H4 0.9300 . ?
C36 C37 1.354(7) . ?
C36 H36 0.9300 . ?
C12 C11 1.380(6) . ?
C12 H12 0.9300 . ?
C2 C3 1.380(6) . ?
C2 H2 0.9300 . ?
C26 C25 1.369(7) . ?
C26 H26 0.9300 . ?
N1 O4 1.227(5) . ?
N1 O3 1.229(5) . ?
C30 C31 1.359(7) . ?
C30 H30 0.9300 . ?
C6 C5 1.396(6) . ?
C6 H6 0.9300 . ?
C8 C9 1.380(6) . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
C32 C31 1.371(6) . ?
C32 H32 0.9300 . ?
C18 C17 1.382(6) . ?
C18 H18 0.9300 . ?
C17 C16 1.363(7) . ?
C17 H17 0.9300 . ?
C24 C25 1.346(6) . ?
C24 H24 0.9300 . ?
C9 C10 1.363(7) . ?
C9 H9 0.9300 . ?
C16 C15 1.352(8) . ?
C16 H16 0.9300 . ?
C37 C38 1.369(7) . ?
C37 H37 0.9300 . ?
C31 H31 0.9300 . ?
C25 H25 0.9300 . ?
C38 H38 0.9300 . ?
C10 C11 1.371(7) . ?
C10 H10 0.9300 . ?
C5 H5 0.9300 . ?
C15 H15 0.9300 . ?
C11 H11 0.9300 . ?

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 C1 113.16(19) . . ?
O1 P1 C7 112.23(18) . . ?
C1 P1 C7 108.33(19) . . ?
O1 P1 C19 110.52(17) . . ?
C1 P1 C19 107.07(19) . . ?
C7 P1 C19 105.08(19) . . ?
O2 P2 C22 114.21(18) . . ?
O2 P2 C28 111.81(18) . . ?
C22 P2 C28 108.01(19) . . ?
O2 P2 C21 111.71(18) . . ?
C22 P2 C21 104.88(19) . . ?
C28 P2 C21 105.64(19) . . ?
C20 C19 C13 121.7(4) . . ?
C20 C19 P1 119.8(3) . . ?
C13 C19 P1 118.6(3) . . ?
C23 C22 C27 118.8(4) . . ?
C23 C22 P2 123.3(3) . . ?
C27 C22 P2 117.9(3) . . ?
C21 C20 C19 174.8(5) . . ?
C34 C35 C36 123.0(5) . . ?
C34 C35 N1 120.4(4) . . ?
C36 C35 N1 116.7(4) . . ?
C20 C21 C34 123.8(4) . . ?
C20 C21 P2 117.4(3) . . ?
C34 C21 P2 117.8(3) . . ?
C22 C23 C24 120.8(4) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C6 C1 C2 120.0(4) . . ?
C6 C1 P1 118.1(4) . . ?
C2 C1 P1 121.9(3) . . ?
C8 C7 C12 118.5(4) . . ?
C8 C7 P1 117.4(3) . . ?
C12 C7 P1 124.0(3) . . ?
C15 C14 C13 117.6(5) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C35 C34 C39 116.6(4) . . ?
C35 C34 C21 126.0(4) . . ?
C39 C34 C21 117.1(4) . . ?
C18 C13 C14 120.0(4) . . ?
C18 C13 C19 120.5(4) . . ?
C14 C13 C19 119.4(4) . . ?
C33 C28 C29 118.3(4) . . ?
C33 C28 P2 123.8(3) . . ?
C29 C28 P2 117.9(3) . . ?
C28 C33 C32 120.0(4) . . ?
C28 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C38 C39 C34 121.0(5) . . ?
C38 C39 H39 119.5 . . ?
C34 C39 H39 119.5 . . ?
C22 C27 C26 119.5(4) . . ?
C22 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C30 C29 C28 121.4(5) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C5 C4 C3 120.2(5) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C37 C36 C35 119.3(5) . . ?
C37 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C11 C12 C7 119.7(5) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C25 C26 C27 119.6(5) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
O4 N1 O3 121.4(5) . . ?
O4 N1 C35 118.9(5) . . ?
O3 N1 C35 119.6(5) . . ?
C31 C30 C29 120.0(5) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C1 C6 C5 119.7(5) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C7 C8 C9 121.8(4) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C4 C3 C2 120.6(5) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C31 C32 C33 119.9(5) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C13 C18 C17 120.4(5) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C16 C17 C18 119.9(5) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C25 C24 C23 120.0(5) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C10 C9 C8 118.9(5) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C15 C16 C17 120.4(5) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C36 C37 C38 119.7(5) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C30 C31 C32 120.5(5) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C24 C25 C26 121.2(5) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
C37 C38 C39 120.5(5) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 H38 119.8 . . ?
C9 C10 C11 120.6(5) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C4 C5 C6 120.0(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C16 C15 C14 121.7(5) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C10 C11 C12 120.5(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.045
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_compound-9
_database_code_depnum_ccdc_archive 'CCDC 1041552'
_audit_update_record             
;
2014-12-30 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H31 N O4 P2'
_chemical_formula_weight         651.60

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'

_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                   11.1755(11)
_cell_length_b                   15.950(2)
_cell_length_c                   18.117(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3229.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1393
_cell_measurement_theta_min      3.1740
_cell_measurement_theta_max      20.1320

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8409
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_sigmaI/netI    0.1207
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5200
_reflns_number_gt                3242
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0383P)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   -0.03(16)
_refine_ls_number_reflns         5200
_refine_ls_number_parameters     425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.1471
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.06547(14) 0.41795(9) 0.89769(10) 0.0431(4) Uani 1 1 d . . .
P2 P 0.37881(14) 0.62367(9) 0.89292(10) 0.0460(4) Uani 1 1 d . . .
O1 O -0.0295(3) 0.3659(2) 0.8655(2) 0.0566(12) Uani 1 1 d . . .
C21 C 0.2563(6) 0.4976(4) 0.8349(3) 0.0451(16) Uani 1 1 d . . .
O2 O 0.3896(4) 0.6078(2) 0.9724(2) 0.0619(12) Uani 1 1 d . . .
C23 C 0.5115(5) 0.6726(4) 0.8561(3) 0.0435(16) Uani 1 1 d . . .
C13 C 0.0783(5) 0.4998(3) 0.7596(4) 0.0449(16) Uani 1 1 d . . .
C22 C 0.3629(5) 0.5256(3) 0.8414(3) 0.0385(15) Uani 1 1 d . . .
C1 C 0.1779(5) 0.3588(3) 0.9447(4) 0.0457(16) Uani 1 1 d . . .
C20 C 0.1430(5) 0.4757(3) 0.8266(3) 0.0398(15) Uani 1 1 d . . .
C7 C 0.0102(5) 0.4936(3) 0.9607(3) 0.0444(16) Uani 1 1 d . . .
C29 C 0.2539(5) 0.6859(4) 0.8677(4) 0.0478(17) Uani 1 1 d . . .
C35 C 0.4732(5) 0.4789(4) 0.8233(4) 0.0447(16) Uani 1 1 d . . .
C12 C -0.1078(6) 0.4974(4) 0.9757(4) 0.0565(18) Uani 1 1 d . . .
H12 H -0.1600 0.4602 0.9528 0.068 Uiso 1 1 calc R . .
C14 C 0.1276(6) 0.4842(4) 0.6903(3) 0.0590(18) Uani 1 1 d . . .
H14 H 0.1997 0.4555 0.6860 0.071 Uiso 1 1 calc R . .
C19 C -0.0292(6) 0.5394(4) 0.7649(4) 0.0595(19) Uani 1 1 d . . .
H19 H -0.0648 0.5478 0.8107 0.071 Uiso 1 1 calc R . .
O3 O 0.4093(5) 0.5660(4) 0.6973(3) 0.0960(18) Uani 1 1 d . . .
C34 C 0.2101(6) 0.6908(4) 0.7979(4) 0.059(2) Uani 1 1 d . . .
H34 H 0.2447 0.6583 0.7609 0.071 Uiso 1 1 calc R . .
C40 C 0.5454(6) 0.4904(4) 0.7634(4) 0.0562(19) Uani 1 1 d . . .
C30 C 0.2015(6) 0.7330(4) 0.9226(5) 0.065(2) Uani 1 1 d . . .
H30 H 0.2297 0.7295 0.9708 0.078 Uiso 1 1 calc R . .
C33 C 0.1168(7) 0.7421(4) 0.7807(5) 0.073(2) Uani 1 1 d . . .
H33 H 0.0877 0.7449 0.7327 0.088 Uiso 1 1 calc R . .
C16 C -0.0369(7) 0.5533(5) 0.6331(4) 0.067(2) Uani 1 1 d . . .
C8 C 0.0851(6) 0.5482(4) 0.9969(4) 0.0626(19) Uani 1 1 d . . .
H8 H 0.1668 0.5462 0.9874 0.075 Uiso 1 1 calc R . .
C10 C -0.0759(8) 0.6082(4) 1.0599(5) 0.079(2) Uani 1 1 d . . .
H10 H -0.1053 0.6467 1.0939 0.095 Uiso 1 1 calc R . .
C2 C 0.1921(7) 0.3610(4) 1.0189(4) 0.070(2) Uani 1 1 d . . .
H2 H 0.1444 0.3959 1.0476 0.084 Uiso 1 1 calc R . .
C15 C 0.0693(7) 0.5113(4) 0.6291(4) 0.067(2) Uani 1 1 d . . .
H15 H 0.1027 0.5010 0.5830 0.081 Uiso 1 1 calc R . .
C6 C 0.2421(6) 0.3021(4) 0.9050(5) 0.077(2) Uani 1 1 d . . .
H6 H 0.2299 0.2975 0.8544 0.092 Uiso 1 1 calc R . .
C31 C 0.1073(7) 0.7850(5) 0.9060(6) 0.092(3) Uani 1 1 d . . .
H31 H 0.0718 0.8170 0.9429 0.111 Uiso 1 1 calc R . .
C24 C 0.6185(6) 0.6520(4) 0.8879(4) 0.0617(18) Uani 1 1 d . . .
H24 H 0.6202 0.6133 0.9262 0.074 Uiso 1 1 calc R . .
C36 C 0.5115(6) 0.4226(4) 0.8747(4) 0.0601(19) Uani 1 1 d . . .
H36 H 0.4653 0.4124 0.9164 0.072 Uiso 1 1 calc R . .
C39 C 0.6519(6) 0.4496(5) 0.7546(5) 0.068(2) Uani 1 1 d . . .
H39 H 0.6980 0.4594 0.7127 0.082 Uiso 1 1 calc R . .
C9 C 0.0427(8) 0.6052(4) 1.0462(4) 0.074(2) Uani 1 1 d . . .
H9 H 0.0948 0.6416 1.0701 0.088 Uiso 1 1 calc R . .
N1 N 0.5147(7) 0.5487(4) 0.7058(4) 0.076(2) Uani 1 1 d . . .
C11 C -0.1525(7) 0.5563(5) 1.0252(4) 0.075(2) Uani 1 1 d . . .
H11 H -0.2343 0.5597 1.0342 0.090 Uiso 1 1 calc R . .
C37 C 0.6189(8) 0.3804(5) 0.8652(5) 0.089(3) Uani 1 1 d . . .
H37 H 0.6421 0.3409 0.9002 0.106 Uiso 1 1 calc R . .
C18 C -0.0850(6) 0.5672(4) 0.7009(4) 0.071(2) Uani 1 1 d . . .
H18 H -0.1571 0.5961 0.7045 0.085 Uiso 1 1 calc R . .
C28 C 0.5085(6) 0.7318(4) 0.8014(4) 0.0593(19) Uani 1 1 d . . .
H28 H 0.4360 0.7472 0.7802 0.071 Uiso 1 1 calc R . .
C27 C 0.6125(8) 0.7682(4) 0.7782(5) 0.078(2) Uani 1 1 d . . .
H27 H 0.6104 0.8083 0.7410 0.093 Uiso 1 1 calc R . .
C26 C 0.7185(7) 0.7466(5) 0.8088(5) 0.083(3) Uani 1 1 d . . .
H26 H 0.7888 0.7717 0.7924 0.100 Uiso 1 1 calc R . .
C25 C 0.7227(7) 0.6874(5) 0.8643(5) 0.079(2) Uani 1 1 d . . .
H25 H 0.7954 0.6719 0.8852 0.095 Uiso 1 1 calc R . .
O4 O 0.5916(6) 0.5793(4) 0.6674(4) 0.120(2) Uani 1 1 d . . .
C17 C -0.0958(8) 0.5862(5) 0.5651(5) 0.121(3) Uani 1 1 d . . .
H17A H -0.1776 0.6000 0.5758 0.181 Uiso 1 1 calc R . .
H17B H -0.0933 0.5442 0.5271 0.181 Uiso 1 1 calc R . .
H17C H -0.0545 0.6355 0.5485 0.181 Uiso 1 1 calc R . .
C5 C 0.3251(9) 0.2514(5) 0.9393(6) 0.102(3) Uani 1 1 d . . .
H5 H 0.3694 0.2133 0.9117 0.122 Uiso 1 1 calc R . .
C4 C 0.3422(8) 0.2567(5) 1.0122(7) 0.098(4) Uani 1 1 d . . .
H4 H 0.3985 0.2227 1.0351 0.117 Uiso 1 1 calc R . .
C38 C 0.6908(8) 0.3950(5) 0.8066(6) 0.093(3) Uani 1 1 d . . .
H38 H 0.7646 0.3685 0.8021 0.111 Uiso 1 1 calc R . .
C3 C 0.2787(8) 0.3106(5) 1.0517(5) 0.091(3) Uani 1 1 d . . .
H3A H 0.2922 0.3148 1.1022 0.109 Uiso 1 1 calc R . .
C32 C 0.0662(7) 0.7898(5) 0.8360(7) 0.091(3) Uani 1 1 d . . .
H32 H 0.0031 0.8257 0.8249 0.109 Uiso 1 1 calc R . .


_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 1.468(4) . ?
P1 C7 1.772(6) . ?
P1 C1 1.788(6) . ?
P1 C20 1.806(6) . ?
P2 O2 1.467(4) . ?
P2 C29 1.773(6) . ?
P2 C23 1.803(6) . ?
P2 C22 1.829(6) . ?
C21 C22 1.278(8) . ?
C21 C20 1.322(8) . ?
C23 C24 1.367(8) . ?
C23 C28 1.369(7) . ?
C13 C19 1.361(8) . ?
C13 C14 1.393(8) . ?
C13 C20 1.463(8) . ?
C22 C35 1.478(8) . ?
C1 C2 1.352(8) . ?
C1 C6 1.360(8) . ?
C7 C12 1.348(8) . ?
C7 C8 1.375(8) . ?
C29 C34 1.360(8) . ?
C29 C30 1.377(8) . ?
C35 C36 1.363(8) . ?
C35 C40 1.365(8) . ?
C12 C11 1.390(9) . ?
C12 H12 0.9300 . ?
C14 C15 1.356(8) . ?
C14 H14 0.9300 . ?
C19 C18 1.390(8) . ?
C19 H19 0.9300 . ?
O3 N1 1.220(7) . ?
C34 C33 1.362(9) . ?
C34 H34 0.9300 . ?
C40 C39 1.366(9) . ?
C40 N1 1.438(9) . ?
C30 C31 1.375(9) . ?
C30 H30 0.9300 . ?
C33 C32 1.379(10) . ?
C33 H33 0.9300 . ?
C16 C18 1.359(9) . ?
C16 C15 1.364(9) . ?
C16 C17 1.492(9) . ?
C8 C9 1.359(8) . ?
C8 H8 0.9300 . ?
C10 C11 1.347(9) . ?
C10 C9 1.350(9) . ?
C10 H10 0.9300 . ?
C2 C3 1.392(10) . ?
C2 H2 0.9300 . ?
C15 H15 0.9300 . ?
C6 C5 1.379(11) . ?
C6 H6 0.9300 . ?
C31 C32 1.351(11) . ?
C31 H31 0.9300 . ?
C24 C25 1.363(9) . ?
C24 H24 0.9300 . ?
C36 C37 1.386(9) . ?
C36 H36 0.9300 . ?
C39 C38 1.354(10) . ?
C39 H39 0.9300 . ?
C9 H9 0.9300 . ?
N1 O4 1.208(7) . ?
C11 H11 0.9300 . ?
C37 C38 1.353(10) . ?
C37 H37 0.9300 . ?
C18 H18 0.9300 . ?
C28 C27 1.365(9) . ?
C28 H28 0.9300 . ?
C27 C26 1.353(10) . ?
C27 H27 0.9300 . ?
C26 C25 1.379(10) . ?
C26 H26 0.9300 . ?
C25 H25 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C5 C4 1.336(12) . ?
C5 H5 0.9300 . ?
C4 C3 1.324(11) . ?
C4 H4 0.9300 . ?
C38 H38 0.9300 . ?
C3 H3A 0.9300 . ?
C32 H32 0.9300 . ?

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 112.9(3) . . ?
O1 P1 C1 113.6(2) . . ?
C7 P1 C1 107.3(3) . . ?
O1 P1 C20 110.6(3) . . ?
C7 P1 C20 106.3(3) . . ?
C1 P1 C20 105.8(3) . . ?
O2 P2 C29 114.5(3) . . ?
O2 P2 C23 111.7(3) . . ?
C29 P2 C23 108.1(3) . . ?
O2 P2 C22 111.2(2) . . ?
C29 P2 C22 105.7(3) . . ?
C23 P2 C22 105.2(3) . . ?
C22 C21 C20 174.8(7) . . ?
C24 C23 C28 119.4(6) . . ?
C24 C23 P2 117.4(5) . . ?
C28 C23 P2 123.1(5) . . ?
C19 C13 C14 119.7(7) . . ?
C19 C13 C20 120.0(6) . . ?
C14 C13 C20 120.3(6) . . ?
C21 C22 C35 125.5(5) . . ?
C21 C22 P2 115.9(5) . . ?
C35 C22 P2 117.6(4) . . ?
C2 C1 C6 118.8(6) . . ?
C2 C1 P1 122.8(5) . . ?
C6 C1 P1 118.0(5) . . ?
C21 C20 C13 119.9(6) . . ?
C21 C20 P1 120.9(5) . . ?
C13 C20 P1 119.2(4) . . ?
C12 C7 C8 118.1(6) . . ?
C12 C7 P1 120.1(5) . . ?
C8 C7 P1 121.8(5) . . ?
C34 C29 C30 119.2(6) . . ?
C34 C29 P2 123.7(6) . . ?
C30 C29 P2 117.0(6) . . ?
C36 C35 C40 116.5(6) . . ?
C36 C35 C22 116.3(6) . . ?
C40 C35 C22 127.1(6) . . ?
C7 C12 C11 120.8(7) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C15 C14 C13 119.3(7) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C13 C19 C18 119.1(7) . . ?
C13 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C29 C34 C33 121.5(7) . . ?
C29 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C35 C40 C39 122.9(7) . . ?
C35 C40 N1 121.5(7) . . ?
C39 C40 N1 115.5(7) . . ?
C31 C30 C29 119.8(8) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C34 C33 C32 118.7(8) . . ?
C34 C33 H33 120.6 . . ?
C32 C33 H33 120.6 . . ?
C18 C16 C15 118.2(7) . . ?
C18 C16 C17 121.0(8) . . ?
C15 C16 C17 120.8(8) . . ?
C9 C8 C7 121.6(7) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C11 C10 C9 121.0(8) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C1 C2 C3 119.3(7) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C14 C15 C16 122.1(7) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C1 C6 C5 120.4(8) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C32 C31 C30 120.0(8) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C25 C24 C23 121.1(7) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C35 C36 C37 120.5(7) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
C38 C39 C40 120.3(8) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C10 C9 C8 119.2(7) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
O4 N1 O3 121.5(8) . . ?
O4 N1 C40 120.6(7) . . ?
O3 N1 C40 117.9(7) . . ?
C10 C11 C12 119.3(7) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C38 C37 C36 121.8(9) . . ?
C38 C37 H37 119.1 . . ?
C36 C37 H37 119.1 . . ?
C16 C18 C19 121.6(7) . . ?
C16 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C27 C28 C23 119.7(7) . . ?
C27 C28 H28 120.1 . . ?
C23 C28 H28 120.1 . . ?
C26 C27 C28 120.7(7) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C27 C26 C25 120.2(8) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C24 C25 C26 118.9(7) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C5 C6 120.3(9) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C3 C4 C5 119.9(9) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C37 C38 C39 117.8(8) . . ?
C37 C38 H38 121.1 . . ?
C39 C38 H38 121.1 . . ?
C4 C3 C2 121.1(9) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C31 C32 C33 120.7(8) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.047
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_compound-10
_database_code_depnum_ccdc_archive 'CCDC 1041553'
_audit_update_record             
;
2014-12-30 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H30 Cl N O4 P2'
_chemical_formula_weight         686.04

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'
N N 0.0311 0.0180 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9475(3)
_cell_length_b                   13.0705(5)
_cell_length_c                   14.9853(5)
_cell_angle_alpha                106.240(3)
_cell_angle_beta                 94.143(3)
_cell_angle_gamma                110.585(3)
_cell_volume                     1719.36(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5466
_cell_measurement_theta_min      3.8220
_cell_measurement_theta_max      71.3020

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    2.211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63898
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            11875
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         71.67
_reflns_number_total             6554
_reflns_number_gt                5708
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0716P)²+0.3938P] 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_number_reflns         6554
_refine_ls_number_parameters     434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
P1 P 0.40128(5) 0.08209(4) 0.23673(3) 0.03387(12) Uani 1 1 d . . .
P2 P 0.28416(5) 0.41462(4) 0.28923(3) 0.03871(13) Uani 1 1 d . . .
Cl1 Cl 0.36177(10) 0.37247(8) -0.10128(5) 0.0993(3) Uani 1 1 d . . .
O1 O 0.37122(16) -0.04087(11) 0.18570(9) 0.0459(3) Uani 1 1 d . . .
C35 C 0.1641(2) 0.25903(15) 0.09449(12) 0.0378(4) Uani 1 1 d . . .
C1 C 0.49754(19) 0.13194(15) 0.35710(12) 0.0369(4) Uani 1 1 d . . .
C20 C 0.23162(18) 0.10503(14) 0.25002(11) 0.0338(3) Uani 1 1 d . . .
C7 C 0.50264(19) 0.17795(16) 0.17722(12) 0.0380(4) Uani 1 1 d . . .
O2 O 0.44118(17) 0.45717(14) 0.32479(12) 0.0627(4) Uani 1 1 d . . .
C22 C 0.20870(18) 0.27256(14) 0.19588(12) 0.0346(3) Uani 1 1 d . . .
C21 C 0.21487(18) 0.18614(15) 0.22074(12) 0.0353(3) Uani 1 1 d . . .
C36 C 0.0255(2) 0.18720(16) 0.04042(14) 0.0461(4) Uani 1 1 d . . .
C13 C 0.1192(2) 0.03104(15) 0.29024(12) 0.0383(4) Uani 1 1 d . . .
C2 C 0.4975(2) 0.22934(17) 0.42511(13) 0.0455(4) Uani 1 1 d . . .
H2 H 0.4492 0.2726 0.4085 0.055 Uiso 1 1 calc R . .
O3 O -0.11621(19) 0.18158(18) 0.15452(15) 0.0753(5) Uani 1 1 d . . .
C23 C 0.1819(2) 0.39789(16) 0.38285(14) 0.0452(4) Uani 1 1 d . . .
C34 C 0.3538(3) 0.60398(18) 0.23144(15) 0.0527(5) Uani 1 1 d . . .
H34 H 0.4492 0.6145 0.2534 0.063 Uiso 1 1 calc R . .
C19 C 0.1409(2) -0.05143(18) 0.32484(15) 0.0477(4) Uani 1 1 d . . .
H19 H 0.2279 -0.0627 0.3220 0.057 Uiso 1 1 calc R . .
C40 C 0.2679(2) 0.31594(17) 0.04911(14) 0.0465(4) Uani 1 1 d . . .
H40 H 0.3620 0.3643 0.0825 0.056 Uiso 1 1 calc R . .
N1 N -0.0905(2) 0.12570(17) 0.08329(15) 0.0591(5) Uani 1 1 d . . .
C29 C 0.2381(2) 0.51005(15) 0.23680(13) 0.0425(4) Uani 1 1 d . . .
C8 C 0.5919(2) 0.29243(18) 0.22245(15) 0.0508(5) Uani 1 1 d . . .
H8 H 0.6018 0.3244 0.2875 0.061 Uiso 1 1 calc R . .
C4 C 0.6403(2) 0.1977(2) 0.54193(15) 0.0567(5) Uani 1 1 d . . .
H4 H 0.6886 0.2198 0.6039 0.068 Uiso 1 1 calc R . .
C6 C 0.5682(2) 0.06714(19) 0.38271(15) 0.0485(4) Uani 1 1 d . . .
H6 H 0.5672 0.0011 0.3379 0.058 Uiso 1 1 calc R . .
C18 C 0.0343(2) -0.1169(2) 0.36345(16) 0.0545(5) Uani 1 1 d . . .
H18 H 0.0517 -0.1710 0.3865 0.065 Uiso 1 1 calc R . .
C12 C 0.4899(3) 0.1311(2) 0.08000(14) 0.0535(5) Uani 1 1 d . . .
H12 H 0.4299 0.0540 0.0486 0.064 Uiso 1 1 calc R . .
C39 C 0.2309(3) 0.3004(2) -0.04597(15) 0.0572(5) Uani 1 1 d . . .
C3 C 0.5687(2) 0.26206(19) 0.51714(14) 0.0516(5) Uani 1 1 d . . .
H3 H 0.5686 0.3273 0.5624 0.062 Uiso 1 1 calc R . .
C37 C -0.0094(3) 0.1706(2) -0.05498(16) 0.0610(6) Uani 1 1 d . . .
H37 H -0.1024 0.1208 -0.0893 0.073 Uiso 1 1 calc R . .
C11 C 0.5668(3) 0.1993(2) 0.02999(16) 0.0662(6) Uani 1 1 d . . .
H11 H 0.5589 0.1677 -0.0349 0.079 Uiso 1 1 calc R . .
C16 C -0.0966(3) -0.1039(2) 0.36852(18) 0.0609(6) Uani 1 1 d . . .
C28 C 0.2626(3) 0.43898(19) 0.47410(16) 0.0588(6) Uani 1 1 d . . .
H28 H 0.3643 0.4712 0.4844 0.071 Uiso 1 1 calc R . .
C5 C 0.6401(3) 0.1007(2) 0.47502(17) 0.0613(6) Uani 1 1 d . . .
H5 H 0.6885 0.0576 0.4920 0.074 Uiso 1 1 calc R . .
C24 C 0.0299(3) 0.3488(2) 0.36825(18) 0.0607(6) Uani 1 1 d . . .
H24 H -0.0248 0.3201 0.3073 0.073 Uiso 1 1 calc R . .
C10 C 0.6539(3) 0.3127(2) 0.07554(18) 0.0658(6) Uani 1 1 d . . .
H10 H 0.7049 0.3582 0.0415 0.079 Uiso 1 1 calc R . .
C30 C 0.0974(3) 0.4943(2) 0.2023(2) 0.0702(7) Uani 1 1 d . . .
H30 H 0.0186 0.4310 0.2046 0.084 Uiso 1 1 calc R . .
C38 C 0.0937(3) 0.2280(2) -0.09821(16) 0.0646(6) Uani 1 1 d . . .
H38 H 0.0716 0.2183 -0.1622 0.078 Uiso 1 1 calc R . .
C33 C 0.3290(3) 0.6825(2) 0.19368(19) 0.0685(7) Uani 1 1 d . . .
H33 H 0.4074 0.7456 0.1905 0.082 Uiso 1 1 calc R . .
O4 O -0.1573(3) 0.02191(18) 0.04329(18) 0.0991(7) Uani 1 1 d . . .
C25 C -0.0400(3) 0.3427(2) 0.4444(2) 0.0762(8) Uani 1 1 d . . .
H25 H -0.1416 0.3105 0.4346 0.091 Uiso 1 1 calc R . .
C9 C 0.6667(3) 0.3600(2) 0.17158(18) 0.0638(6) Uani 1 1 d . . .
H9 H 0.7256 0.4376 0.2024 0.077 Uiso 1 1 calc R . .
C14 C -0.0133(3) 0.0420(2) 0.2940(2) 0.0742(8) Uani 1 1 d . . .
H14 H -0.0322 0.0951 0.2703 0.089 Uiso 1 1 calc R . .
C26 C 0.0414(4) 0.3844(2) 0.5348(2) 0.0842(10) Uani 1 1 d . . .
H26 H -0.0056 0.3804 0.5859 0.101 Uiso 1 1 calc R . .
C27 C 0.1918(4) 0.4320(2) 0.54974(18) 0.0790(9) Uani 1 1 d . . .
H27 H 0.2460 0.4596 0.6108 0.095 Uiso 1 1 calc R . .
C31 C 0.0738(4) 0.5730(3) 0.1641(3) 0.0909(10) Uani 1 1 d . . .
H31 H -0.0209 0.5621 0.1403 0.109 Uiso 1 1 calc R . .
C15 C -0.1179(3) -0.0238(3) 0.3321(3) 0.0925(11) Uani 1 1 d . . .
H15 H -0.2060 -0.0141 0.3334 0.111 Uiso 1 1 calc R . .
C32 C 0.1906(4) 0.6674(3) 0.1614(2) 0.0805(8) Uani 1 1 d . . .
H32 H 0.1741 0.7211 0.1372 0.097 Uiso 1 1 calc R . .
C17 C -0.2134(4) -0.1747(3) 0.4102(3) 0.0917(10) Uani 1 1 d . . .
H17A H -0.2640 -0.2509 0.3654 0.138 Uiso 1 1 calc R . .
H17B H -0.2815 -0.1385 0.4249 0.138 Uiso 1 1 calc R . .
H17C H -0.1691 -0.1799 0.4670 0.138 Uiso 1 1 calc R . .


_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 1.4828(13) . ?
P1 C7 1.8023(18) . ?
P1 C1 1.8027(17) . ?
P1 C20 1.8300(17) . ?
P2 O2 1.4616(16) . ?
P2 C23 1.809(2) . ?
P2 C29 1.8115(19) . ?
P2 C22 1.8395(17) . ?
Cl1 C39 1.732(3) . ?
C35 C40 1.388(3) . ?
C35 C36 1.393(3) . ?
C35 C22 1.494(2) . ?
C1 C6 1.385(3) . ?
C1 C2 1.391(3) . ?
C20 C21 1.311(2) . ?
C20 C13 1.487(2) . ?
C7 C8 1.378(3) . ?
C7 C12 1.390(3) . ?
C22 C21 1.304(2) . ?
C36 C37 1.383(3) . ?
C36 N1 1.461(3) . ?
C13 C14 1.379(3) . ?
C13 C19 1.392(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
O3 N1 1.214(3) . ?
C23 C28 1.389(3) . ?
C23 C24 1.392(3) . ?
C34 C29 1.384(3) . ?
C34 C33 1.385(3) . ?
C34 H34 0.9300 . ?
C19 C18 1.385(3) . ?
C19 H19 0.9300 . ?
C40 C39 1.384(3) . ?
C40 H40 0.9300 . ?
N1 O4 1.223(3) . ?
C29 C30 1.378(3) . ?
C8 C9 1.383(3) . ?
C8 H8 0.9300 . ?
C4 C5 1.378(4) . ?
C4 C3 1.382(3) . ?
C4 H4 0.9300 . ?
C6 C5 1.384(3) . ?
C6 H6 0.9300 . ?
C18 C16 1.376(3) . ?
C18 H18 0.9300 . ?
C12 C11 1.385(3) . ?
C12 H12 0.9300 . ?
C39 C38 1.376(4) . ?
C3 H3 0.9300 . ?
C37 C38 1.364(4) . ?
C37 H37 0.9300 . ?
C11 C10 1.364(4) . ?
C11 H11 0.9300 . ?
C16 C15 1.377(4) . ?
C16 C17 1.507(3) . ?
C28 C27 1.385(4) . ?
C28 H28 0.9300 . ?
C5 H5 0.9300 . ?
C24 C25 1.385(3) . ?
C24 H24 0.9300 . ?
C10 C9 1.375(3) . ?
C10 H10 0.9300 . ?
C30 C31 1.386(3) . ?
C30 H30 0.9300 . ?
C38 H38 0.9300 . ?
C33 C32 1.351(4) . ?
C33 H33 0.9300 . ?
C25 C26 1.381(5) . ?
C25 H25 0.9300 . ?
C9 H9 0.9300 . ?
C14 C15 1.371(3) . ?
C14 H14 0.9300 . ?
C26 C27 1.376(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C31 C32 1.379(4) . ?
C31 H31 0.9300 . ?
C15 H15 0.9300 . ?
C32 H32 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C7 112.63(8) . . ?
O1 P1 C1 113.39(8) . . ?
C7 P1 C1 108.28(8) . . ?
O1 P1 C20 111.33(8) . . ?
C7 P1 C20 107.37(8) . . ?
C1 P1 C20 103.27(8) . . ?
O2 P2 C23 111.01(10) . . ?
O2 P2 C29 112.06(10) . . ?
C23 P2 C29 108.63(9) . . ?
O2 P2 C22 114.22(9) . . ?
C23 P2 C22 105.67(8) . . ?
C29 P2 C22 104.82(8) . . ?
C40 C35 C36 117.29(17) . . ?
C40 C35 C22 118.77(16) . . ?
C36 C35 C22 123.85(17) . . ?
C6 C1 C2 119.51(17) . . ?
C6 C1 P1 118.11(14) . . ?
C2 C1 P1 122.32(14) . . ?
C21 C20 C13 123.25(16) . . ?
C21 C20 P1 116.89(13) . . ?
C13 C20 P1 119.84(12) . . ?
C8 C7 C12 119.15(18) . . ?
C8 C7 P1 123.97(14) . . ?
C12 C7 P1 116.88(15) . . ?
C21 C22 C35 121.18(15) . . ?
C21 C22 P2 115.97(13) . . ?
C35 C22 P2 122.20(12) . . ?
C22 C21 C20 175.30(17) . . ?
C37 C36 C35 122.5(2) . . ?
C37 C36 N1 116.90(18) . . ?
C35 C36 N1 120.65(18) . . ?
C14 C13 C19 117.12(18) . . ?
C14 C13 C20 120.19(17) . . ?
C19 C13 C20 122.69(17) . . ?
C3 C2 C1 120.28(19) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C28 C23 C24 119.5(2) . . ?
C28 C23 P2 116.73(18) . . ?
C24 C23 P2 123.81(17) . . ?
C29 C34 C33 120.6(2) . . ?
C29 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C18 C19 C13 120.77(19) . . ?
C18 C19 H19 119.6 . . ?
C13 C19 H19 119.6 . . ?
C39 C40 C35 119.77(19) . . ?
C39 C40 H40 120.1 . . ?
C35 C40 H40 120.1 . . ?
O3 N1 O4 124.7(2) . . ?
O3 N1 C36 117.82(19) . . ?
O4 N1 C36 117.5(2) . . ?
C30 C29 C34 119.1(2) . . ?
C30 C29 P2 124.37(16) . . ?
C34 C29 P2 116.53(17) . . ?
C7 C8 C9 120.36(19) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C5 C4 C3 120.16(19) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C16 C18 C19 121.7(2) . . ?
C16 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C11 C12 C7 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C38 C39 C40 121.9(2) . . ?
C38 C39 Cl1 119.00(18) . . ?
C40 C39 Cl1 119.09(19) . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C38 C37 C36 119.4(2) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C18 C16 C15 116.9(2) . . ?
C18 C16 C17 122.2(2) . . ?
C15 C16 C17 120.9(2) . . ?
C27 C28 C23 120.0(3) . . ?
C27 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C29 C30 C31 119.8(2) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C37 C38 C39 119.2(2) . . ?
C37 C38 H38 120.4 . . ?
C39 C38 H38 120.4 . . ?
C32 C33 C34 119.9(2) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C27 C26 C25 120.3(2) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 120.2(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C32 C31 C30 120.1(3) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C14 C15 C16 122.1(2) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C33 C32 C31 120.5(2) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        71.67
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.045
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_compound-11
_database_code_depnum_ccdc_archive 'CCDC 1041554'
_audit_update_record             
;
2014-12-30 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H32 Br Cl6 N O4 P2'
_chemical_formula_weight         969.24

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.5145(7)
_cell_length_b                   13.3968(8)
_cell_length_c                   14.6374(9)
_cell_angle_alpha                86.833(5)
_cell_angle_beta                 75.632(5)
_cell_angle_gamma                87.590(5)
_cell_volume                     2183.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4661
_cell_measurement_theta_min      3.4430
_cell_measurement_theta_max      27.2440

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             980
_exptl_absorpt_coefficient_mu    1.424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.31030
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            14094
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0657
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         24.99
_reflns_number_total             7681
_reflns_number_gt                5332
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1157P)²+3.2420P] 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     SHELXL
_refine_ls_extinction_coef       0.031(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7681
_refine_ls_number_parameters     507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0729
_refine_ls_wR_factor_ref         0.2226
_refine_ls_wR_factor_gt          0.2028
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.003
_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
P1 P 0.42611(12) 0.17009(10) 0.67878(9) 0.0346(4) Uani 1 1 d . . .
Br1 Br 0.42758(6) 0.62351(4) 0.92637(5) 0.0566(3) Uani 1 1 d . . .
P2 P 0.28688(11) 0.20596(9) 1.01807(9) 0.0267(3) Uani 1 1 d . . .
N1 N 0.0148(4) 0.3649(4) 0.9078(4) 0.0430(11) Uani 1 1 d . . .
Cl2 Cl 0.1368(5) 0.3950(3) 0.6479(2) 0.1793(18) Uani 1 1 d . . .
Cl6 Cl 0.7440(3) 0.2712(4) 0.4905(3) 0.187(2) Uani 1 1 d . . .
C35 C 0.2276(4) 0.3767(3) 0.9134(3) 0.0263(10) Uani 1 1 d . . .
Cl5 Cl 0.6641(4) 0.2198(6) 0.3405(4) 0.285(4) Uani 1 1 d . . .
O3 O 0.0006(3) 0.2890(3) 0.9584(3) 0.0524(11) Uani 1 1 d . . .
C24 C 0.1707(4) 0.0409(4) 0.9758(4) 0.0370(12) Uani 1 1 d . . .
H24 H 0.1154 0.0858 0.9582 0.044 Uiso 1 1 calc R . .
O4 O -0.0556(4) 0.3958(4) 0.8629(4) 0.0792(15) Uani 1 1 d . . .
C36 C 0.1211(4) 0.4233(4) 0.9024(4) 0.0349(12) Uani 1 1 d . . .
Cl3 Cl 0.0751(6) 0.2629(4) 0.5161(4) 0.217(2) Uani 1 1 d . . .
C23 C 0.2631(4) 0.0751(4) 1.0099(3) 0.0281(10) Uani 1 1 d . . .
C22 C 0.2503(4) 0.2669(3) 0.9135(3) 0.0252(10) Uani 1 1 d . . .
C19 C 0.2021(6) 0.0492(5) 0.6621(4) 0.0511(15) Uani 1 1 d . . .
H19 H 0.2808 0.0332 0.6307 0.061 Uiso 1 1 calc R . .
C21 C 0.2635(4) 0.2171(4) 0.8372(3) 0.0297(11) Uani 1 1 d . . .
C13 C 0.1794(5) 0.1175(4) 0.7338(3) 0.0337(11) Uani 1 1 d . . .
C39 C 0.3041(4) 0.5411(4) 0.9132(4) 0.0350(12) Uani 1 1 d . . .
C1 C 0.4915(4) 0.0471(4) 0.6872(4) 0.0369(12) Uani 1 1 d . . .
C40 C 0.3198(4) 0.4379(4) 0.9190(3) 0.0318(11) Uani 1 1 d . . .
H40 H 0.3921 0.4097 0.9267 0.038 Uiso 1 1 calc R . .
C28 C 0.3438(5) 0.0074(4) 1.0352(4) 0.0366(12) Uani 1 1 d . . .
H28 H 0.4053 0.0304 1.0587 0.044 Uiso 1 1 calc R . .
C27 C 0.3354(5) -0.0937(4) 1.0265(4) 0.0484(15) Uani 1 1 d . . .
H27 H 0.3912 -0.1388 1.0430 0.058 Uiso 1 1 calc R . .
C34 C 0.2051(6) 0.3335(5) 1.1606(4) 0.0507(15) Uani 1 1 d . . .
H34 H 0.2783 0.3639 1.1365 0.061 Uiso 1 1 calc R . .
C3 C 0.5269(6) -0.1026(5) 0.7753(4) 0.0513(15) Uani 1 1 d . . .
H3 H 0.5153 -0.1396 0.8323 0.062 Uiso 1 1 calc R . .
C14 C 0.0619(5) 0.1365(5) 0.7782(5) 0.0553(17) Uani 1 1 d . . .
H14 H 0.0437 0.1824 0.8255 0.066 Uiso 1 1 calc R . .
C29 C 0.1769(4) 0.2526(4) 1.1180(3) 0.0320(11) Uani 1 1 d . . .
C2 C 0.4727(6) -0.0100(4) 0.7711(4) 0.0459(14) Uani 1 1 d . . .
H2 H 0.4225 0.0150 0.8255 0.055 Uiso 1 1 calc R . .
C12 C 0.4940(6) 0.3562(5) 0.7045(5) 0.0562(16) Uani 1 1 d . . .
H12 H 0.4338 0.3776 0.6751 0.067 Uiso 1 1 calc R . .
C20 C 0.2776(4) 0.1677(4) 0.7605(3) 0.0308(11) Uani 1 1 d . . .
C37 C 0.1080(5) 0.5260(4) 0.8920(4) 0.0433(13) Uani 1 1 d . . .
H37 H 0.0370 0.5547 0.8819 0.052 Uiso 1 1 calc R . .
C6 C 0.5637(5) 0.0078(5) 0.6059(4) 0.0463(14) Uani 1 1 d . . .
H6 H 0.5756 0.0445 0.5486 0.056 Uiso 1 1 calc R . .
C4 C 0.5997(6) -0.1405(5) 0.6929(5) 0.0572(17) Uani 1 1 d . . .
H4 H 0.6361 -0.2036 0.6949 0.069 Uiso 1 1 calc R . .
C26 C 0.2429(5) -0.1267(4) 0.9930(5) 0.0540(16) Uani 1 1 d . . .
H26 H 0.2360 -0.1948 0.9873 0.065 Uiso 1 1 calc R . .
C38 C 0.2013(5) 0.5855(4) 0.8965(4) 0.0463(14) Uani 1 1 d . . .
H38 H 0.1946 0.6547 0.8884 0.056 Uiso 1 1 calc R . .
C32 C 0.0191(7) 0.3258(6) 1.2755(4) 0.065(2) Uani 1 1 d . . .
H32 H -0.0340 0.3504 1.3287 0.078 Uiso 1 1 calc R . .
C33 C 0.1254(7) 0.3702(6) 1.2392(5) 0.069(2) Uani 1 1 d . . .
H33 H 0.1447 0.4256 1.2675 0.082 Uiso 1 1 calc R . .
C30 C 0.0688(5) 0.2076(5) 1.1554(4) 0.0551(16) Uani 1 1 d . . .
H30 H 0.0490 0.1521 1.1276 0.066 Uiso 1 1 calc R . .
C8 C 0.6017(6) 0.2252(5) 0.7665(5) 0.0640(19) Uani 1 1 d . . .
H8 H 0.6152 0.1575 0.7790 0.077 Uiso 1 1 calc R . .
C7 C 0.5135(5) 0.2558(4) 0.7213(4) 0.0399(13) Uani 1 1 d . . .
C5 C 0.6179(6) -0.0860(5) 0.6100(5) 0.0545(16) Uani 1 1 d . . .
H5 H 0.6671 -0.1118 0.5555 0.065 Uiso 1 1 calc R . .
C15 C -0.0306(6) 0.0895(6) 0.7547(5) 0.0660(19) Uani 1 1 d . . .
H15 H -0.1092 0.1012 0.7889 0.079 Uiso 1 1 calc R . .
C31 C -0.0097(6) 0.2450(6) 1.2337(5) 0.070(2) Uani 1 1 d . . .
H31 H -0.0830 0.2150 1.2583 0.084 Uiso 1 1 calc R . .
C17 C -0.1093(8) -0.0204(7) 0.6524(7) 0.094(3) Uani 1 1 d . . .
H17A H -0.1374 0.0248 0.6088 0.141 Uiso 1 1 calc R . .
H17B H -0.1735 -0.0331 0.7072 0.141 Uiso 1 1 calc R . .
H17C H -0.0819 -0.0821 0.6227 0.141 Uiso 1 1 calc R . .
C25 C 0.1615(5) -0.0612(4) 0.9683(5) 0.0536(16) Uani 1 1 d . . .
H25 H 0.0993 -0.0848 0.9461 0.064 Uiso 1 1 calc R . .
C18 C 0.1091(6) 0.0058(5) 0.6376(5) 0.0608(18) Uani 1 1 d . . .
H18 H 0.1267 -0.0389 0.5893 0.073 Uiso 1 1 calc R . .
C42 C 0.6305(8) 0.2914(8) 0.4341(7) 0.100(3) Uani 1 1 d . . .
H42 H 0.5544 0.2710 0.4764 0.121 Uiso 1 1 calc R . .
C10 C 0.6508(7) 0.3953(6) 0.7757(6) 0.076(2) Uani 1 1 d . . .
H10 H 0.6970 0.4421 0.7940 0.091 Uiso 1 1 calc R . .
C16 C -0.0076(6) 0.0253(5) 0.6811(5) 0.0595(17) Uani 1 1 d . . .
C41 C 0.1855(10) 0.3253(8) 0.5489(7) 0.112(3) Uani 1 1 d . . .
H41 H 0.2433 0.2746 0.5629 0.134 Uiso 1 1 calc R . .
C9 C 0.6696(8) 0.2954(7) 0.7929(6) 0.086(3) Uani 1 1 d . . .
H9 H 0.7292 0.2744 0.8231 0.103 Uiso 1 1 calc R . .
Cl4 Cl 0.6218(7) 0.4058(5) 0.4039(8) 0.376(6) Uani 1 1 d . . .
C11 C 0.5637(8) 0.4257(5) 0.7312(6) 0.073(2) Uani 1 1 d . . .
H11 H 0.5509 0.4935 0.7187 0.088 Uiso 1 1 calc R . .
Cl1 Cl 0.2574(6) 0.3944(5) 0.4538(3) 0.224(2) Uani 1 1 d . . .
O2 O 0.4103(3) 0.2281(3) 1.0226(2) 0.0363(8) Uani 1 1 d . . .
O1 O 0.4164(4) 0.2007(3) 0.5816(3) 0.0473(10) 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
P1 O1 1.488(4) . ?
P1 C7 1.791(6) . ?
P1 C1 1.794(5) . ?
P1 C20 1.828(5) . ?
Br1 C39 1.890(5) . ?
P2 O2 1.482(3) . ?
P2 C23 1.801(5) . ?
P2 C29 1.803(5) . ?
P2 C22 1.828(5) . ?
N1 O4 1.210(6) . ?
N1 O3 1.218(6) . ?
N1 C36 1.464(7) . ?
Cl2 C41 1.729(11) . ?
Cl6 C42 1.715(11) . ?
C35 C40 1.390(7) . ?
C35 C36 1.394(7) . ?
C35 C22 1.483(6) . ?
Cl5 C42 1.673(11) . ?
C24 C23 1.386(7) . ?
C24 C25 1.389(8) . ?
C36 C37 1.381(7) . ?
Cl3 C41 1.728(11) . ?
C23 C28 1.373(7) . ?
C22 C21 1.305(6) . ?
C19 C18 1.370(8) . ?
C19 C13 1.399(7) . ?
C21 C20 1.307(7) . ?
C13 C14 1.368(8) . ?
C13 C20 1.481(7) . ?
C39 C38 1.372(8) . ?
C39 C40 1.387(7) . ?
C1 C2 1.384(8) . ?
C1 C6 1.388(7) . ?
C28 C27 1.377(8) . ?
C27 C26 1.376(9) . ?
C34 C29 1.368(8) . ?
C34 C33 1.382(9) . ?
C3 C2 1.371(8) . ?
C3 C4 1.394(9) . ?
C14 C15 1.381(9) . ?
C29 C30 1.378(8) . ?
C12 C7 1.372(8) . ?
C12 C11 1.387(10) . ?
C37 C38 1.382(8) . ?
C6 C5 1.384(8) . ?
C4 C5 1.357(9) . ?
C26 C25 1.358(9) . ?
C32 C33 1.355(10) . ?
C32 C31 1.363(10) . ?
C30 C31 1.377(9) . ?
C8 C9 1.378(9) . ?
C8 C7 1.380(8) . ?
C15 C16 1.384(9) . ?
C17 C16 1.501(9) . ?
C18 C16 1.358(9) . ?
C42 Cl4 1.577(11) . ?
C10 C11 1.362(11) . ?
C10 C9 1.367(11) . ?
C41 Cl1 1.682(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
O1 P1 C7 111.2(2) . . ?
O1 P1 C1 113.2(2) . . ?
C7 P1 C1 108.0(2) . . ?
O1 P1 C20 110.5(2) . . ?
C7 P1 C20 107.6(2) . . ?
C1 P1 C20 106.1(2) . . ?
O2 P2 C23 113.9(2) . . ?
O2 P2 C29 111.4(2) . . ?
C23 P2 C29 108.8(2) . . ?
O2 P2 C22 111.3(2) . . ?
C23 P2 C22 105.0(2) . . ?
C29 P2 C22 106.0(2) . . ?
O4 N1 O3 123.4(5) . . ?
O4 N1 C36 118.2(5) . . ?
O3 N1 C36 118.4(4) . . ?
C40 C35 C36 117.3(4) . . ?
C40 C35 C22 118.6(4) . . ?
C36 C35 C22 124.0(4) . . ?
C23 C24 C25 119.2(5) . . ?
C37 C36 C35 122.3(5) . . ?
C37 C36 N1 116.8(4) . . ?
C35 C36 N1 120.7(5) . . ?
C28 C23 C24 119.4(5) . . ?
C28 C23 P2 117.7(4) . . ?
C24 C23 P2 122.9(4) . . ?
C21 C22 C35 121.9(4) . . ?
C21 C22 P2 119.7(4) . . ?
C35 C22 P2 117.5(3) . . ?
C18 C19 C13 120.4(6) . . ?
C22 C21 C20 179.5(6) . . ?
C14 C13 C19 116.9(5) . . ?
C14 C13 C20 121.2(5) . . ?
C19 C13 C20 121.9(5) . . ?
C38 C39 C40 121.7(5) . . ?
C38 C39 Br1 118.6(4) . . ?
C40 C39 Br1 119.7(4) . . ?
C2 C1 C6 119.0(5) . . ?
C2 C1 P1 122.8(4) . . ?
C6 C1 P1 118.3(4) . . ?
C39 C40 C35 120.1(4) . . ?
C23 C28 C27 121.3(5) . . ?
C26 C27 C28 118.8(5) . . ?
C29 C34 C33 120.2(6) . . ?
C2 C3 C4 119.1(6) . . ?
C13 C14 C15 121.9(6) . . ?
C34 C29 C30 119.2(5) . . ?
C34 C29 P2 118.0(4) . . ?
C30 C29 P2 122.7(4) . . ?
C3 C2 C1 121.1(5) . . ?
C7 C12 C11 120.2(7) . . ?
C21 C20 C13 124.0(4) . . ?
C21 C20 P1 116.6(4) . . ?
C13 C20 P1 119.3(3) . . ?
C36 C37 C38 119.4(5) . . ?
C5 C6 C1 120.0(6) . . ?
C5 C4 C3 120.5(6) . . ?
C25 C26 C27 121.0(6) . . ?
C39 C38 C37 119.0(5) . . ?
C33 C32 C31 119.9(6) . . ?
C32 C33 C34 120.3(7) . . ?
C31 C30 C29 119.9(6) . . ?
C9 C8 C7 119.7(7) . . ?
C12 C7 C8 119.3(6) . . ?
C12 C7 P1 117.7(5) . . ?
C8 C7 P1 122.9(5) . . ?
C4 C5 C6 120.4(6) . . ?
C14 C15 C16 120.8(6) . . ?
C32 C31 C30 120.4(7) . . ?
C26 C25 C24 120.4(5) . . ?
C16 C18 C19 122.7(6) . . ?
Cl4 C42 Cl5 111.7(8) . . ?
Cl4 C42 Cl6 109.7(8) . . ?
Cl5 C42 Cl6 106.5(6) . . ?
C11 C10 C9 119.3(7) . . ?
C18 C16 C15 117.2(6) . . ?
C18 C16 C17 122.5(7) . . ?
C15 C16 C17 120.3(7) . . ?
Cl1 C41 Cl3 107.1(6) . . ?
Cl1 C41 Cl2 112.5(7) . . ?
Cl3 C41 Cl2 115.3(7) . . ?
C10 C9 C8 121.1(7) . . ?
C10 C11 C12 120.5(7) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.212
_refine_diff_density_min         -0.905
_refine_diff_density_rms         0.096
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_compound-R-12
_database_code_depnum_ccdc_archive 'CCDC 1041555'
_audit_update_record             
;
2014-12-30 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H33 N O4 P2'
_chemical_formula_weight         641.60

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'

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

_cell_length_a                   11.3350(6)
_cell_length_b                   17.7472(12)
_cell_length_c                   16.1457(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3247.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4133
_cell_measurement_theta_min      3.3010
_cell_measurement_theta_max      28.9240

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8301
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5525
_reflns_number_gt                4806
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1064P)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   -0.13(12)
_refine_ls_number_reflns         5525
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1610
_refine_ls_wR_factor_gt          0.1529
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.29656(7) 0.14696(5) 0.82850(5) 0.0330(2) Uani 1 1 d . . .
P2 P 0.61031(7) 0.14920(6) 0.62294(6) 0.0352(2) Uani 1 1 d . . .
C19 C 0.3761(3) 0.0764(2) 0.7685(2) 0.0322(7) Uani 1 1 d . . .
O1 O 0.2024(2) 0.11202(15) 0.87853(16) 0.0444(6) Uani 1 1 d . . .
C22 C 0.4880(3) 0.1183(2) 0.5605(2) 0.0373(8) Uani 1 1 d . . .
O2 O 0.6175(2) 0.23173(16) 0.63296(18) 0.0531(7) Uani 1 1 d . . .
C23 C 0.4556(3) 0.0436(2) 0.5532(2) 0.0437(9) Uani 1 1 d . . .
H23 H 0.4959 0.0072 0.5835 0.052 Uiso 1 1 calc R . .
C20 C 0.4862(3) 0.08810(19) 0.7480(2) 0.0339(7) Uani 1 1 d . . .
C13 C 0.3133(3) 0.0061(2) 0.7448(2) 0.0370(8) Uani 1 1 d . . .
C21 C 0.5929(3) 0.1001(2) 0.7214(2) 0.0339(8) Uani 1 1 d . . .
C39 C 0.7759(3) 0.0264(3) 0.7659(3) 0.0500(10) Uani 1 1 d . . .
N1 N 0.7514(4) -0.0366(3) 0.7073(3) 0.0672(11) Uani 1 1 d . . .
C7 C 0.4061(3) 0.1933(2) 0.8922(2) 0.0370(8) Uani 1 1 d . . .
C34 C 0.6997(3) 0.0877(2) 0.7724(2) 0.0380(8) Uani 1 1 d . . .
C1 C 0.2421(3) 0.2149(2) 0.7557(2) 0.0386(8) Uani 1 1 d . . .
C28 C 0.7452(3) 0.1111(2) 0.5782(3) 0.0435(9) Uani 1 1 d . . .
C18 C 0.3590(4) -0.0620(2) 0.7571(3) 0.0480(9) Uani 1 1 d . . .
H18 H 0.4314 -0.0648 0.7840 0.058 Uiso 1 1 calc R . .
C35 C 0.7311(3) 0.1449(3) 0.8261(3) 0.0571(11) Uani 1 1 d . . .
H35 H 0.6821 0.1866 0.8319 0.069 Uiso 1 1 calc R . .
C6 C 0.1217(4) 0.2300(3) 0.7558(3) 0.0571(11) Uani 1 1 d . . .
H6 H 0.0727 0.2064 0.7940 0.069 Uiso 1 1 calc R . .
C24 C 0.3648(4) 0.0220(3) 0.5019(2) 0.0555(12) Uani 1 1 d . . .
H24 H 0.3446 -0.0286 0.4969 0.067 Uiso 1 1 calc R . .
C4 C 0.1466(6) 0.3164(3) 0.6450(3) 0.0773(16) Uani 1 1 d . . .
H4 H 0.1147 0.3505 0.6074 0.093 Uiso 1 1 calc R . .
C33 C 0.7490(4) 0.0528(3) 0.5233(3) 0.0545(11) Uani 1 1 d . . .
H33 H 0.6792 0.0291 0.5078 0.065 Uiso 1 1 calc R . .
O3 O 0.6510(3) -0.0488(2) 0.6889(3) 0.0983(15) Uani 1 1 d . . .
C14 C 0.1985(3) 0.0150(2) 0.7021(3) 0.0536(10) Uani 1 1 d . . .
H14A H 0.2103 0.0441 0.6520 0.064 Uiso 1 1 calc R . .
H14B H 0.1454 0.0431 0.7377 0.064 Uiso 1 1 calc R . .
C12 C 0.4626(4) 0.1499(3) 0.9511(3) 0.0609(11) Uani 1 1 d . . .
H12 H 0.4472 0.0985 0.9548 0.073 Uiso 1 1 calc R . .
C2 C 0.3132(4) 0.2515(3) 0.6995(3) 0.0549(11) Uani 1 1 d . . .
H2 H 0.3935 0.2407 0.6985 0.066 Uiso 1 1 calc R . .
C29 C 0.8499(3) 0.1471(3) 0.6005(3) 0.0599(11) Uani 1 1 d . . .
H29 H 0.8490 0.1879 0.6368 0.072 Uiso 1 1 calc R . .
C25 C 0.3045(4) 0.0757(3) 0.4582(3) 0.0649(13) Uani 1 1 d . . .
H25 H 0.2439 0.0615 0.4227 0.078 Uiso 1 1 calc R . .
C8 C 0.4278(4) 0.2685(3) 0.8885(3) 0.0564(11) Uani 1 1 d . . .
H8 H 0.3891 0.2986 0.8499 0.068 Uiso 1 1 calc R . .
C26 C 0.3334(4) 0.1512(4) 0.4668(3) 0.0719(15) Uani 1 1 d . . .
H26 H 0.2903 0.1875 0.4385 0.086 Uiso 1 1 calc R . .
C27 C 0.4250(3) 0.1724(3) 0.5166(2) 0.0498(10) Uani 1 1 d . . .
H27 H 0.4453 0.2230 0.5212 0.060 Uiso 1 1 calc R . .
C5 C 0.0748(4) 0.2804(3) 0.6986(4) 0.0745(15) Uani 1 1 d . . .
H5 H -0.0061 0.2893 0.6974 0.089 Uiso 1 1 calc R . .
C38 C 0.8828(4) 0.0246(3) 0.8089(3) 0.0680(14) Uani 1 1 d . . .
H38 H 0.9355 -0.0148 0.8003 0.082 Uiso 1 1 calc R . .
O4 O 0.8331(4) -0.0737(3) 0.6804(3) 0.1082(15) Uani 1 1 d . . .
C3 C 0.2690(5) 0.3033(3) 0.6449(3) 0.0693(14) Uani 1 1 d . . .
H3 H 0.3185 0.3291 0.6088 0.083 Uiso 1 1 calc R . .
C30 C 0.9548(4) 0.1211(3) 0.5678(4) 0.0710(15) Uani 1 1 d . . .
H30 H 1.0253 0.1433 0.5843 0.085 Uiso 1 1 calc R . .
C32 C 0.8543(4) 0.0283(3) 0.4906(4) 0.0744(15) Uani 1 1 d . . .
H32 H 0.8561 -0.0121 0.4540 0.089 Uiso 1 1 calc R . .
C10 C 0.5646(5) 0.2579(4) 0.9988(3) 0.0756(16) Uani 1 1 d . . .
H10 H 0.6192 0.2803 1.0340 0.091 Uiso 1 1 calc R . .
C17 C 0.3039(5) -0.1325(2) 0.7317(3) 0.0670(13) Uani 1 1 d . . .
H17A H 0.3573 -0.1596 0.6954 0.080 Uiso 1 1 calc R . .
H17B H 0.2899 -0.1635 0.7801 0.080 Uiso 1 1 calc R . .
C11 C 0.5428(5) 0.1836(4) 1.0049(3) 0.0795(17) Uani 1 1 d . . .
H11 H 0.5811 0.1548 1.0448 0.095 Uiso 1 1 calc R . .
C9 C 0.5084(5) 0.2995(3) 0.9429(3) 0.0727(14) Uani 1 1 d . . .
H9 H 0.5237 0.3510 0.9403 0.087 Uiso 1 1 calc R . .
C31 C 0.9571(4) 0.0645(4) 0.5128(4) 0.0802(17) Uani 1 1 d . . .
H31 H 1.0284 0.0496 0.4896 0.096 Uiso 1 1 calc R . .
C36 C 0.8361(4) 0.1408(4) 0.8719(3) 0.0742(15) Uani 1 1 d . . .
H36 H 0.8558 0.1793 0.9084 0.089 Uiso 1 1 calc R . .
C37 C 0.9096(4) 0.0800(4) 0.8629(4) 0.0796(17) Uani 1 1 d . . .
H37 H 0.9783 0.0770 0.8942 0.096 Uiso 1 1 calc R . .
C16 C 0.1942(9) -0.1200(4) 0.6893(8) 0.163(5) Uani 1 1 d . . .
H16A H 0.2055 -0.1398 0.6339 0.196 Uiso 1 1 calc R . .
H16B H 0.1376 -0.1531 0.7159 0.196 Uiso 1 1 calc R . .
C15 C 0.1422(5) -0.0584(4) 0.6802(6) 0.118(3) Uani 1 1 d . . .
H15A H 0.0695 -0.0616 0.7116 0.142 Uiso 1 1 calc R . .
H15B H 0.1199 -0.0552 0.6223 0.142 Uiso 1 1 calc R . .


_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 1.475(3) . ?
P1 C1 1.793(4) . ?
P1 C7 1.810(4) . ?
P1 C19 1.823(4) . ?
P2 O2 1.476(3) . ?
P2 C22 1.800(4) . ?
P2 C28 1.821(4) . ?
P2 C21 1.824(4) . ?
C19 C20 1.307(5) . ?
C19 C13 1.487(5) . ?
C22 C23 1.380(5) . ?
C22 C27 1.390(5) . ?
C23 C24 1.376(5) . ?
C20 C21 1.301(5) . ?
C13 C18 1.329(5) . ?
C13 C14 1.481(5) . ?
C21 C34 1.480(5) . ?
C39 C34 1.394(6) . ?
C39 C38 1.396(6) . ?
C39 N1 1.491(6) . ?
N1 O3 1.195(5) . ?
N1 O4 1.216(5) . ?
C7 C8 1.359(6) . ?
C7 C12 1.380(6) . ?
C34 C35 1.381(6) . ?
C1 C2 1.377(6) . ?
C1 C6 1.391(5) . ?
C28 C33 1.364(6) . ?
C28 C29 1.395(6) . ?
C18 C17 1.458(6) . ?
C35 C36 1.403(6) . ?
C6 C5 1.392(7) . ?
C24 C25 1.368(7) . ?
C4 C5 1.350(8) . ?
C4 C3 1.407(8) . ?
C33 C32 1.375(6) . ?
C14 C15 1.494(7) . ?
C12 C11 1.392(7) . ?
C2 C3 1.368(6) . ?
C29 C30 1.380(7) . ?
C25 C26 1.386(8) . ?
C8 C9 1.382(7) . ?
C26 C27 1.367(6) . ?
C38 C37 1.350(9) . ?
C30 C31 1.341(8) . ?
C32 C31 1.378(8) . ?
C10 C9 1.329(9) . ?
C10 C11 1.346(9) . ?
C17 C16 1.436(9) . ?
C36 C37 1.370(9) . ?
C16 C15 1.251(9) . ?

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 C1 113.10(16) . . ?
O1 P1 C7 112.09(15) . . ?
C1 P1 C7 107.64(17) . . ?
O1 P1 C19 111.11(16) . . ?
C1 P1 C19 106.52(16) . . ?
C7 P1 C19 105.96(15) . . ?
O2 P2 C22 114.00(17) . . ?
O2 P2 C28 111.44(18) . . ?
C22 P2 C28 108.17(18) . . ?
O2 P2 C21 112.60(17) . . ?
C22 P2 C21 105.00(16) . . ?
C28 P2 C21 105.03(17) . . ?
C20 C19 C13 121.8(3) . . ?
C20 C19 P1 119.8(3) . . ?
C13 C19 P1 118.5(2) . . ?
C23 C22 C27 118.8(3) . . ?
C23 C22 P2 123.1(3) . . ?
C27 C22 P2 118.1(3) . . ?
C24 C23 C22 121.2(4) . . ?
C21 C20 C19 175.3(4) . . ?
C18 C13 C14 120.6(4) . . ?
C18 C13 C19 122.5(3) . . ?
C14 C13 C19 116.8(3) . . ?
C20 C21 C34 123.5(3) . . ?
C20 C21 P2 117.8(3) . . ?
C34 C21 P2 117.8(2) . . ?
C34 C39 C38 121.3(4) . . ?
C34 C39 N1 121.1(3) . . ?
C38 C39 N1 117.4(4) . . ?
O3 N1 O4 122.5(5) . . ?
O3 N1 C39 118.1(4) . . ?
O4 N1 C39 119.4(4) . . ?
C8 C7 C12 119.6(4) . . ?
C8 C7 P1 123.0(3) . . ?
C12 C7 P1 117.2(3) . . ?
C35 C34 C39 117.4(4) . . ?
C35 C34 C21 116.8(4) . . ?
C39 C34 C21 125.6(3) . . ?
C2 C1 C6 119.0(4) . . ?
C2 C1 P1 123.2(3) . . ?
C6 C1 P1 117.8(3) . . ?
C33 C28 C29 119.3(4) . . ?
C33 C28 P2 124.4(3) . . ?
C29 C28 P2 116.2(3) . . ?
C13 C18 C17 124.8(4) . . ?
C34 C35 C36 120.8(5) . . ?
C1 C6 C5 119.9(5) . . ?
C25 C24 C23 119.3(5) . . ?
C5 C4 C3 121.1(5) . . ?
C28 C33 C32 121.0(4) . . ?
C13 C14 C15 113.1(4) . . ?
C7 C12 C11 119.5(5) . . ?
C3 C2 C1 121.8(4) . . ?
C30 C29 C28 118.7(5) . . ?
C24 C25 C26 120.3(4) . . ?
C7 C8 C9 118.9(5) . . ?
C27 C26 C25 120.3(5) . . ?
C26 C27 C22 120.0(5) . . ?
C4 C5 C6 120.0(4) . . ?
C37 C38 C39 119.9(5) . . ?
C2 C3 C4 118.2(5) . . ?
C31 C30 C29 121.4(5) . . ?
C33 C32 C31 119.2(5) . . ?
C9 C10 C11 120.4(5) . . ?
C16 C17 C18 111.9(4) . . ?
C10 C11 C12 119.7(5) . . ?
C10 C9 C8 121.8(5) . . ?
C30 C31 C32 120.3(5) . . ?
C37 C36 C35 120.0(5) . . ?
C38 C37 C36 120.4(4) . . ?
C15 C16 C17 126.8(6) . . ?
C16 C15 C14 122.2(6) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.060
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_compound-S-12
_database_code_depnum_ccdc_archive 'CCDC 1041556'
_audit_update_record             
;
2014-12-30 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H33 N O4 P2'
_chemical_formula_weight         641.60

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'

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

_cell_length_a                   11.3101(10)
_cell_length_b                   17.7378(17)
_cell_length_c                   16.0426(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3218.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.3010
_cell_measurement_theta_max      28.9240

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.80772
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8699
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5523
_reflns_number_gt                4835
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0808P)²+0.1146P] 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   -0.27(11)
_refine_ls_number_reflns         5523
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1354
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
P2 P 0.38964(7) 0.14851(5) 0.62246(5) 0.0341(2) Uani 1 1 d . . .
P1 P 0.70330(7) 0.14665(4) 0.82862(5) 0.0322(2) Uani 1 1 d . . .
O1 O 0.7976(2) 0.11173(12) 0.87871(15) 0.0441(5) Uani 1 1 d . . .
C19 C 0.6236(3) 0.07618(17) 0.76852(19) 0.0314(7) Uani 1 1 d . . .
C22 C 0.5115(3) 0.11826(17) 0.5603(2) 0.0346(7) Uani 1 1 d . . .
O2 O 0.3820(2) 0.23083(12) 0.63314(16) 0.0505(6) Uani 1 1 d . . .
C20 C 0.5141(3) 0.08798(15) 0.7478(2) 0.0333(7) Uani 1 1 d . . .
C21 C 0.4074(3) 0.09930(16) 0.72126(19) 0.0324(7) Uani 1 1 d . . .
C39 C 0.2244(3) 0.0258(2) 0.7653(2) 0.0463(8) Uani 1 1 d . . .
C23 C 0.5436(3) 0.0433(2) 0.5529(2) 0.0421(8) Uani 1 1 d . . .
H23 H 0.5026 0.0067 0.5826 0.051 Uiso 1 1 calc R . .
C28 C 0.2552(3) 0.11051(19) 0.5778(2) 0.0381(8) Uani 1 1 d . . .
C13 C 0.6871(3) 0.00570(17) 0.7443(2) 0.0360(7) Uani 1 1 d . . .
C18 C 0.6397(4) -0.06219(19) 0.7580(2) 0.0483(9) Uani 1 1 d . . .
H18 H 0.5673 -0.0648 0.7854 0.058 Uiso 1 1 calc R . .
C1 C 0.7576(3) 0.21444(17) 0.7556(2) 0.0387(8) Uani 1 1 d . . .
C34 C 0.2998(3) 0.08719(19) 0.7725(2) 0.0377(7) Uani 1 1 d . . .
C7 C 0.5940(3) 0.19272(18) 0.89161(19) 0.0368(7) Uani 1 1 d . . .
C35 C 0.2690(3) 0.1437(2) 0.8263(2) 0.0535(9) Uani 1 1 d . . .
H35 H 0.3186 0.1851 0.8327 0.064 Uiso 1 1 calc R . .
C6 C 0.6857(4) 0.2518(2) 0.7001(2) 0.0532(10) Uani 1 1 d . . .
H6 H 0.6050 0.2419 0.6998 0.064 Uiso 1 1 calc R . .
C12 C 0.5362(4) 0.1499(2) 0.9505(2) 0.0604(10) Uani 1 1 d . . .
H12 H 0.5504 0.0983 0.9535 0.072 Uiso 1 1 calc R . .
C2 C 0.8786(3) 0.2288(2) 0.7545(3) 0.0565(10) Uani 1 1 d . . .
H2 H 0.9282 0.2041 0.7918 0.068 Uiso 1 1 calc R . .
C4 C 0.8524(5) 0.3157(3) 0.6445(3) 0.0745(14) Uani 1 1 d . . .
H4 H 0.8842 0.3496 0.6064 0.089 Uiso 1 1 calc R . .
C33 C 0.1496(3) 0.1452(2) 0.6001(3) 0.0555(10) Uani 1 1 d . . .
H33 H 0.1499 0.1852 0.6376 0.067 Uiso 1 1 calc R . .
C29 C 0.2517(3) 0.0521(2) 0.5227(2) 0.0503(9) Uani 1 1 d . . .
H29 H 0.3216 0.0281 0.5075 0.060 Uiso 1 1 calc R . .
C24 C 0.6359(3) 0.0224(2) 0.5017(2) 0.0547(10) Uani 1 1 d . . .
H24 H 0.6572 -0.0281 0.4970 0.066 Uiso 1 1 calc R . .
C27 C 0.5740(3) 0.1721(2) 0.5164(2) 0.0489(9) Uani 1 1 d . . .
H27 H 0.5533 0.2227 0.5206 0.059 Uiso 1 1 calc R . .
C25 C 0.6960(4) 0.0761(3) 0.4580(3) 0.0632(11) Uani 1 1 d . . .
H25 H 0.7569 0.0620 0.4223 0.076 Uiso 1 1 calc R . .
O4 O 0.3502(3) -0.04969(19) 0.6893(3) 0.0965(13) Uani 1 1 d . . .
C14 C 0.8015(3) 0.0147(2) 0.7021(3) 0.0528(9) Uani 1 1 d . . .
H14A H 0.8543 0.0430 0.7381 0.063 Uiso 1 1 calc R . .
H14B H 0.7900 0.0438 0.6515 0.063 Uiso 1 1 calc R . .
C5 C 0.7311(5) 0.3032(2) 0.6453(3) 0.0701(13) Uani 1 1 d . . .
H5 H 0.6817 0.3293 0.6091 0.084 Uiso 1 1 calc R . .
C8 C 0.5725(4) 0.26920(19) 0.8884(3) 0.0548(10) Uani 1 1 d . . .
H8 H 0.6117 0.2993 0.8498 0.066 Uiso 1 1 calc R . .
C30 C 0.1459(4) 0.0283(3) 0.4891(3) 0.0697(12) Uani 1 1 d . . .
H30 H 0.1443 -0.0113 0.4512 0.084 Uiso 1 1 calc R . .
C3 C 0.9250(4) 0.2796(2) 0.6981(3) 0.0708(13) Uani 1 1 d . . .
H3 H 1.0059 0.2889 0.6970 0.085 Uiso 1 1 calc R . .
O3 O 0.1670(3) -0.0738(2) 0.6802(3) 0.1038(13) Uani 1 1 d . . .
C38 C 0.1168(3) 0.0237(3) 0.8093(3) 0.0656(12) Uani 1 1 d . . .
H38 H 0.0645 -0.0162 0.8015 0.079 Uiso 1 1 calc R . .
C32 C 0.0456(4) 0.1206(2) 0.5670(3) 0.0688(13) Uani 1 1 d . . .
H32 H -0.0248 0.1437 0.5827 0.083 Uiso 1 1 calc R . .
C10 C 0.4353(4) 0.2584(3) 0.9989(3) 0.0750(14) Uani 1 1 d . . .
H10 H 0.3801 0.2806 1.0341 0.090 Uiso 1 1 calc R . .
C26 C 0.6671(4) 0.1506(3) 0.4664(3) 0.0674(12) Uani 1 1 d . . .
H26 H 0.7106 0.1871 0.4381 0.081 Uiso 1 1 calc R . .
C17 C 0.6961(5) -0.1328(2) 0.7320(3) 0.0677(12) Uani 1 1 d . . .
H17A H 0.7107 -0.1638 0.7808 0.081 Uiso 1 1 calc R . .
H17B H 0.6426 -0.1603 0.6957 0.081 Uiso 1 1 calc R . .
C31 C 0.0432(4) 0.0634(3) 0.5121(4) 0.0753(14) Uani 1 1 d . . .
H31 H -0.0284 0.0476 0.4897 0.090 Uiso 1 1 calc R . .
C9 C 0.4927(4) 0.3004(3) 0.9426(3) 0.0718(13) Uani 1 1 d . . .
H9 H 0.4780 0.3520 0.9403 0.086 Uiso 1 1 calc R . .
C11 C 0.4576(4) 0.1829(3) 1.0050(3) 0.0802(14) Uani 1 1 d . . .
H11 H 0.4201 0.1540 1.0455 0.096 Uiso 1 1 calc R . .
C37 C 0.0899(4) 0.0801(3) 0.8633(3) 0.0721(13) Uani 1 1 d . . .
H37 H 0.0207 0.0777 0.8945 0.086 Uiso 1 1 calc R . .
C36 C 0.1634(4) 0.1399(3) 0.8718(3) 0.0728(13) Uani 1 1 d . . .
H36 H 0.1436 0.1787 0.9082 0.087 Uiso 1 1 calc R . .
C16 C 0.8050(8) -0.1204(3) 0.6893(7) 0.173(5) Uani 1 1 d . . .
H16A H 0.8618 -0.1539 0.7154 0.208 Uiso 1 1 calc R . .
H16B H 0.7930 -0.1396 0.6333 0.208 Uiso 1 1 calc R . .
C15 C 0.8579(5) -0.0583(3) 0.6806(6) 0.124(3) Uani 1 1 d . . .
H15A H 0.8813 -0.0550 0.6225 0.149 Uiso 1 1 calc R . .
H15B H 0.9302 -0.0615 0.7129 0.149 Uiso 1 1 calc R . .
N1 N 0.2482(3) -0.0367(2) 0.7078(3) 0.0654(10) 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
P2 O2 1.473(2) . ?
P2 C22 1.784(3) . ?
P2 C28 1.811(3) . ?
P2 C21 1.821(3) . ?
P1 O1 1.472(2) . ?
P1 C1 1.788(3) . ?
P1 C7 1.794(3) . ?
P1 C19 1.818(3) . ?
C19 C20 1.300(4) . ?
C19 C13 1.493(4) . ?
C22 C27 1.382(5) . ?
C22 C23 1.384(5) . ?
C20 C21 1.295(5) . ?
C21 C34 1.484(4) . ?
C39 C34 1.388(5) . ?
C39 C38 1.408(5) . ?
C39 N1 1.467(5) . ?
C23 C24 1.379(5) . ?
C28 C29 1.362(5) . ?
C28 C33 1.391(5) . ?
C13 C18 1.337(4) . ?
C13 C14 1.468(5) . ?
C18 C17 1.467(5) . ?
C1 C6 1.376(5) . ?
C1 C2 1.392(5) . ?
C34 C35 1.368(5) . ?
C7 C12 1.377(5) . ?
C7 C8 1.379(5) . ?
C35 C36 1.401(5) . ?
C6 C5 1.367(5) . ?
C12 C11 1.377(6) . ?
C2 C3 1.382(6) . ?
C4 C3 1.350(7) . ?
C4 C5 1.390(7) . ?
C33 C32 1.362(6) . ?
C29 C30 1.379(5) . ?
C24 C25 1.364(6) . ?
C27 C26 1.377(5) . ?
C25 C26 1.369(6) . ?
O4 N1 1.213(4) . ?
C14 C15 1.485(6) . ?
C8 C9 1.371(6) . ?
C30 C31 1.368(6) . ?
O3 N1 1.214(4) . ?
C38 C37 1.357(7) . ?
C32 C31 1.344(7) . ?
C10 C9 1.339(7) . ?
C10 C11 1.366(7) . ?
C17 C16 1.427(8) . ?
C37 C36 1.355(7) . ?
C16 C15 1.261(8) . ?

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
O2 P2 C22 114.12(15) . . ?
O2 P2 C28 111.45(15) . . ?
C22 P2 C28 108.38(15) . . ?
O2 P2 C21 112.38(15) . . ?
C22 P2 C21 104.90(14) . . ?
C28 P2 C21 105.00(15) . . ?
O1 P1 C1 113.07(15) . . ?
O1 P1 C7 112.55(14) . . ?
C1 P1 C7 107.44(15) . . ?
O1 P1 C19 111.06(13) . . ?
C1 P1 C19 106.57(14) . . ?
C7 P1 C19 105.69(14) . . ?
C20 C19 C13 121.8(3) . . ?
C20 C19 P1 119.8(2) . . ?
C13 C19 P1 118.4(2) . . ?
C27 C22 C23 119.0(3) . . ?
C27 C22 P2 118.2(3) . . ?
C23 C22 P2 122.7(2) . . ?
C21 C20 C19 175.6(3) . . ?
C20 C21 C34 124.0(3) . . ?
C20 C21 P2 117.6(2) . . ?
C34 C21 P2 117.4(2) . . ?
C34 C39 C38 120.8(4) . . ?
C34 C39 N1 122.1(3) . . ?
C38 C39 N1 117.0(4) . . ?
C24 C23 C22 120.6(3) . . ?
C29 C28 C33 118.6(3) . . ?
C29 C28 P2 124.3(3) . . ?
C33 C28 P2 117.0(3) . . ?
C18 C13 C14 121.9(3) . . ?
C18 C13 C19 121.2(3) . . ?
C14 C13 C19 116.9(3) . . ?
C13 C18 C17 123.2(4) . . ?
C6 C1 C2 119.0(3) . . ?
C6 C1 P1 123.0(3) . . ?
C2 C1 P1 118.0(3) . . ?
C35 C34 C39 118.0(3) . . ?
C35 C34 C21 116.9(3) . . ?
C39 C34 C21 124.9(3) . . ?
C12 C7 C8 119.0(3) . . ?
C12 C7 P1 117.5(3) . . ?
C8 C7 P1 123.3(3) . . ?
C34 C35 C36 120.7(4) . . ?
C5 C6 C1 121.1(4) . . ?
C7 C12 C11 120.5(4) . . ?
C3 C2 C1 120.1(4) . . ?
C3 C4 C5 121.3(4) . . ?
C32 C33 C28 120.0(4) . . ?
C28 C29 C30 120.8(4) . . ?
C25 C24 C23 119.7(4) . . ?
C26 C27 C22 119.9(4) . . ?
C24 C25 C26 120.3(4) . . ?
C13 C14 C15 113.0(4) . . ?
C6 C5 C4 118.9(5) . . ?
C9 C8 C7 119.3(4) . . ?
C31 C30 C29 119.5(4) . . ?
C4 C3 C2 119.7(4) . . ?
C37 C38 C39 119.6(4) . . ?
C31 C32 C33 121.0(4) . . ?
C9 C10 C11 120.3(4) . . ?
C25 C26 C27 120.4(4) . . ?
C16 C17 C18 112.4(4) . . ?
C32 C31 C30 120.2(4) . . ?
C10 C9 C8 121.4(4) . . ?
C10 C11 C12 119.3(5) . . ?
C36 C37 C38 120.3(4) . . ?
C37 C36 C35 120.5(5) . . ?
C15 C16 C17 126.7(5) . . ?
C16 C15 C14 122.2(5) . . ?
O4 N1 O3 121.8(4) . . ?
O4 N1 C39 118.2(4) . . ?
O3 N1 C39 120.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_compound-13
_database_code_depnum_ccdc_archive 'CCDC 1041557'
_audit_update_record             
;
2014-12-30 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H33 Cl N O4 P2'
_chemical_formula_weight         677.05

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7782(6)
_cell_length_b                   12.6735(7)
_cell_length_c                   15.2180(9)
_cell_angle_alpha                72.422(5)
_cell_angle_beta                 88.076(5)
_cell_angle_gamma                69.077(5)
_cell_volume                     1673.42(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3968
_cell_measurement_theta_min      3.3340
_cell_measurement_theta_max      28.8740

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             706
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            10471
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5885
_reflns_number_gt                4453
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlisPro, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0797P)²+0.4115P] 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_number_reflns         5885
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1545
_refine_ls_wR_factor_gt          0.1409
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.68595(7) 0.92220(6) 0.23884(5) 0.0380(2) Uani 1 1 d . . .
P2 P 1.12933(7) 0.58901(6) 0.29288(5) 0.0387(2) Uani 1 1 d . . .
Cl1 Cl 1.02384(15) 0.62407(10) -0.09016(7) 0.0983(4) Uani 1 1 d . . .
O1 O 0.5890(2) 1.04504(16) 0.18841(13) 0.0490(5) Uani 1 1 d . . .
O2 O 1.0099(2) 0.54518(17) 0.32418(13) 0.0522(5) Uani 1 1 d . . .
C19 C 0.8770(3) 0.9085(2) 0.25324(17) 0.0383(6) Uani 1 1 d . . .
C21 C 1.0671(3) 0.7349(2) 0.20435(18) 0.0369(6) Uani 1 1 d . . .
C20 C 0.9761(3) 0.8246(2) 0.22752(17) 0.0385(6) Uani 1 1 d . . .
C22 C 1.2173(3) 0.6053(2) 0.38690(19) 0.0434(6) Uani 1 1 d . . .
C7 C 0.6809(3) 0.8206(2) 0.17943(18) 0.0411(6) Uani 1 1 d . . .
C1 C 0.6439(3) 0.8704(2) 0.35679(18) 0.0395(6) Uani 1 1 d . . .
C39 C 1.0533(3) 0.6890(2) 0.05852(19) 0.0477(7) Uani 1 1 d . . .
H39 H 1.0006 0.6418 0.0877 0.057 Uiso 1 1 calc R . .
C28 C 1.2640(3) 0.4912(2) 0.24067(18) 0.0404(6) Uani 1 1 d . . .
C34 C 1.1008(3) 0.7481(2) 0.10617(18) 0.0408(6) Uani 1 1 d . . .
C13 C 0.9117(3) 0.9918(2) 0.29231(18) 0.0420(6) Uani 1 1 d . . .
N1 N 1.2321(3) 0.8830(3) 0.1040(2) 0.0630(7) Uani 1 1 d . . .
C33 C 1.2394(3) 0.3918(2) 0.23705(19) 0.0490(7) Uani 1 1 d . . .
H33 H 1.1556 0.3788 0.2602 0.059 Uiso 1 1 calc R . .
C29 C 1.3878(3) 0.5101(3) 0.2039(2) 0.0572(8) Uani 1 1 d . . .
H29 H 1.4055 0.5773 0.2045 0.069 Uiso 1 1 calc R . .
C6 C 0.7464(3) 0.7793(3) 0.42378(19) 0.0524(7) Uani 1 1 d . . .
H6 H 0.8387 0.7392 0.4077 0.063 Uiso 1 1 calc R . .
C18 C 0.8086(3) 1.0758(3) 0.3169(2) 0.0514(7) Uani 1 1 d . . .
H18A H 0.7561 1.0359 0.3619 0.062 Uiso 1 1 calc R . .
H18B H 0.7401 1.1231 0.2627 0.062 Uiso 1 1 calc R . .
C35 C 1.1759(3) 0.8192(2) 0.0577(2) 0.0485(7) Uani 1 1 d . . .
C8 C 0.6442(3) 0.8670(3) 0.0853(2) 0.0552(8) Uani 1 1 d . . .
H8 H 0.6256 0.9471 0.0556 0.066 Uiso 1 1 calc R . .
O4 O 1.3127(3) 0.8271(3) 0.1738(2) 0.0773(7) Uani 1 1 d . . .
C32 C 1.3384(4) 0.3113(3) 0.1992(2) 0.0635(9) Uani 1 1 d . . .
H32 H 1.3215 0.2442 0.1977 0.076 Uiso 1 1 calc R . .
C12 C 0.7075(3) 0.7016(3) 0.2232(2) 0.0506(7) Uani 1 1 d . . .
H12 H 0.7309 0.6694 0.2868 0.061 Uiso 1 1 calc R . .
C23 C 1.1672(4) 0.5729(3) 0.4739(2) 0.0562(8) Uani 1 1 d . . .
H23 H 1.0893 0.5461 0.4813 0.067 Uiso 1 1 calc R . .
C38 C 1.0837(4) 0.6995(3) -0.0324(2) 0.0572(8) Uani 1 1 d . . .
C9 C 0.6347(4) 0.7952(3) 0.0348(2) 0.0681(9) Uani 1 1 d . . .
H9 H 0.6094 0.8269 -0.0287 0.082 Uiso 1 1 calc R . .
C31 C 1.4602(4) 0.3306(3) 0.1644(2) 0.0659(9) Uani 1 1 d . . .
H31 H 1.5267 0.2764 0.1392 0.079 Uiso 1 1 calc R . .
C30 C 1.4850(4) 0.4291(3) 0.1663(3) 0.0701(10) Uani 1 1 d . . .
H30 H 1.5683 0.4419 0.1419 0.084 Uiso 1 1 calc R . .
C36 C 1.2042(4) 0.8312(3) -0.0331(2) 0.0634(9) Uani 1 1 d . . .
H36 H 1.2534 0.8807 -0.0635 0.076 Uiso 1 1 calc R . .
C10 C 0.6627(4) 0.6781(3) 0.0786(3) 0.0681(9) Uani 1 1 d . . .
H10 H 0.6569 0.6295 0.0447 0.082 Uiso 1 1 calc R . .
C37 C 1.1590(4) 0.7696(3) -0.0777(2) 0.0658(9) Uani 1 1 d . . .
H37 H 1.1793 0.7751 -0.1387 0.079 Uiso 1 1 calc R . .
C2 C 0.5077(3) 0.9270(3) 0.3807(2) 0.0565(8) Uani 1 1 d . . .
H2 H 0.4372 0.9874 0.3359 0.068 Uiso 1 1 calc R . .
C5 C 0.7125(4) 0.7475(3) 0.5141(2) 0.0583(8) Uani 1 1 d . . .
H5 H 0.7824 0.6870 0.5591 0.070 Uiso 1 1 calc R . .
C26 C 1.3989(4) 0.6504(3) 0.4538(3) 0.0744(10) Uani 1 1 d . . .
H26 H 1.4778 0.6761 0.4471 0.089 Uiso 1 1 calc R . .
C4 C 0.5771(4) 0.8043(3) 0.5375(2) 0.0603(8) Uani 1 1 d . . .
H4 H 0.5542 0.7819 0.5985 0.072 Uiso 1 1 calc R . .
O3 O 1.1947(4) 0.9895(3) 0.0687(2) 0.1098(11) Uani 1 1 d . . .
C24 C 1.2334(5) 0.5807(3) 0.5490(2) 0.0744(10) Uani 1 1 d . . .
H24 H 1.1990 0.5601 0.6071 0.089 Uiso 1 1 calc R . .
C27 C 1.3334(3) 0.6448(3) 0.3781(2) 0.0573(8) Uani 1 1 d . . .
H27 H 1.3672 0.6678 0.3202 0.069 Uiso 1 1 calc R . .
C16 C 0.9928(5) 1.1440(5) 0.3644(4) 0.1198(19) Uani 1 1 d . . .
H16A H 1.0013 1.2201 0.3330 0.144 Uiso 1 1 calc R . .
H16B H 1.0197 1.1259 0.4295 0.144 Uiso 1 1 calc R . .
C3 C 0.4748(4) 0.8940(3) 0.4722(2) 0.0682(9) Uani 1 1 d . . .
H3 H 0.3826 0.9333 0.4889 0.082 Uiso 1 1 calc R . .
C11 C 0.6992(4) 0.6309(3) 0.1719(2) 0.0638(9) Uani 1 1 d . . .
H11 H 0.7185 0.5506 0.2010 0.077 Uiso 1 1 calc R . .
C17 C 0.8358(4) 1.1622(3) 0.3558(3) 0.0653(9) Uani 1 1 d . . .
H17A H 0.7823 1.2423 0.3161 0.078 Uiso 1 1 calc R . .
H17B H 0.7982 1.1544 0.4163 0.078 Uiso 1 1 calc R . .
C14 C 1.0699(3) 0.9756(3) 0.3025(3) 0.0708(10) Uani 1 1 d . . .
H14A H 1.1229 0.8976 0.3456 0.085 Uiso 1 1 calc R . .
H14B H 1.1106 0.9787 0.2432 0.085 Uiso 1 1 calc R . .
C25 C 1.3492(5) 0.6185(3) 0.5388(3) 0.0786(11) Uani 1 1 d . . .
H25 H 1.3941 0.6225 0.5900 0.094 Uiso 1 1 calc R . .
C15 C 1.0925(5) 1.0657(6) 0.3355(5) 0.158(3) Uani 1 1 d . . .
H15A H 1.1695 1.0225 0.3857 0.189 Uiso 1 1 calc R . .
H15B H 1.1340 1.1101 0.2857 0.189 Uiso 1 1 calc R . .


_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 1.4779(19) . ?
P1 C7 1.797(3) . ?
P1 C1 1.804(3) . ?
P1 C19 1.828(3) . ?
P2 O2 1.4713(19) . ?
P2 C22 1.794(3) . ?
P2 C28 1.806(3) . ?
P2 C21 1.831(3) . ?
Cl1 C38 1.724(3) . ?
C19 C20 1.309(3) . ?
C19 C13 1.493(4) . ?
C21 C20 1.306(3) . ?
C21 C34 1.492(3) . ?
C22 C27 1.383(4) . ?
C22 C23 1.390(4) . ?
C7 C8 1.379(4) . ?
C7 C12 1.383(4) . ?
C1 C2 1.365(4) . ?
C1 C6 1.381(4) . ?
C39 C34 1.379(4) . ?
C39 C38 1.381(4) . ?
C39 H39 0.9300 . ?
C28 C33 1.381(4) . ?
C28 C29 1.384(4) . ?
C34 C35 1.388(4) . ?
C13 C18 1.319(4) . ?
C13 C14 1.494(4) . ?
N1 O4 1.207(4) . ?
N1 O3 1.212(4) . ?
N1 C35 1.462(4) . ?
C33 C32 1.386(4) . ?
C33 H33 0.9300 . ?
C29 C30 1.381(4) . ?
C29 H29 0.9300 . ?
C6 C5 1.375(4) . ?
C6 H6 0.9300 . ?
C18 C17 1.493(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C35 C36 1.373(4) . ?
C8 C9 1.384(4) . ?
C8 H8 0.9300 . ?
C32 C31 1.359(5) . ?
C32 H32 0.9300 . ?
C12 C11 1.376(4) . ?
C12 H12 0.9300 . ?
C23 C24 1.379(5) . ?
C23 H23 0.9300 . ?
C38 C37 1.368(5) . ?
C9 C10 1.359(5) . ?
C9 H9 0.9300 . ?
C31 C30 1.363(5) . ?
C31 H31 0.9300 . ?
C30 H30 0.9300 . ?
C36 C37 1.362(5) . ?
C36 H36 0.9300 . ?
C10 C11 1.368(5) . ?
C10 H10 0.9300 . ?
C37 H37 0.9300 . ?
C2 C3 1.390(4) . ?
C2 H2 0.9300 . ?
C5 C4 1.357(5) . ?
C5 H5 0.9300 . ?
C26 C25 1.363(5) . ?
C26 C27 1.369(5) . ?
C26 H26 0.9300 . ?
C4 C3 1.361(5) . ?
C4 H4 0.9300 . ?
C24 C25 1.366(6) . ?
C24 H24 0.9300 . ?
C27 H27 0.9300 . ?
C16 C15 1.294(6) . ?
C16 C17 1.473(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C14 C15 1.462(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C25 H25 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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 111.02(12) . . ?
O1 P1 C1 113.59(11) . . ?
C7 P1 C1 109.19(12) . . ?
O1 P1 C19 112.25(12) . . ?
C7 P1 C19 108.05(12) . . ?
C1 P1 C19 102.29(12) . . ?
O2 P2 C22 111.02(13) . . ?
O2 P2 C28 111.31(12) . . ?
C22 P2 C28 109.63(12) . . ?
O2 P2 C21 113.47(11) . . ?
C22 P2 C21 105.91(12) . . ?
C28 P2 C21 105.20(12) . . ?
C20 C19 C13 123.9(2) . . ?
C20 C19 P1 116.6(2) . . ?
C13 C19 P1 119.46(18) . . ?
C20 C21 C34 120.7(2) . . ?
C20 C21 P2 117.43(19) . . ?
C34 C21 P2 121.23(17) . . ?
C21 C20 C19 174.6(3) . . ?
C27 C22 C23 118.7(3) . . ?
C27 C22 P2 123.9(2) . . ?
C23 C22 P2 117.3(2) . . ?
C8 C7 C12 119.4(3) . . ?
C8 C7 P1 116.9(2) . . ?
C12 C7 P1 123.7(2) . . ?
C2 C1 C6 119.4(3) . . ?
C2 C1 P1 118.3(2) . . ?
C6 C1 P1 122.2(2) . . ?
C34 C39 C38 120.3(3) . . ?
C34 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C33 C28 C29 118.6(2) . . ?
C33 C28 P2 116.9(2) . . ?
C29 C28 P2 124.5(2) . . ?
C39 C34 C35 116.8(2) . . ?
C39 C34 C21 119.3(2) . . ?
C35 C34 C21 123.9(2) . . ?
C18 C13 C19 122.2(3) . . ?
C18 C13 C14 121.1(3) . . ?
C19 C13 C14 116.8(2) . . ?
O4 N1 O3 124.1(3) . . ?
O4 N1 C35 118.6(3) . . ?
O3 N1 C35 117.2(3) . . ?
C28 C33 C32 120.6(3) . . ?
C28 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C30 C29 C28 119.9(3) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C5 C6 C1 120.3(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C13 C18 C17 124.8(3) . . ?
C13 C18 H18A 106.1 . . ?
C17 C18 H18A 106.1 . . ?
C13 C18 H18B 106.1 . . ?
C17 C18 H18B 106.1 . . ?
H18A C18 H18B 106.3 . . ?
C36 C35 C34 123.0(3) . . ?
C36 C35 N1 117.0(3) . . ?
C34 C35 N1 120.0(2) . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C31 C32 C33 120.0(3) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C11 C12 C7 119.5(3) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C24 C23 C22 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C37 C38 C39 121.3(3) . . ?
C37 C38 Cl1 119.3(2) . . ?
C39 C38 Cl1 119.4(2) . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C32 C31 C30 120.1(3) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C30 C29 120.7(3) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C37 C36 C35 118.9(3) . . ?
C37 C36 H36 120.5 . . ?
C35 C36 H36 120.5 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C36 C37 C38 119.7(3) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C1 C2 C3 119.7(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C25 C26 C27 120.3(4) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C25 C24 C23 120.4(3) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C27 C22 120.6(3) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C15 C16 C17 122.2(4) . . ?
C15 C16 H16A 106.8 . . ?
C17 C16 H16A 106.8 . . ?
C15 C16 H16B 106.8 . . ?
C17 C16 H16B 106.8 . . ?
H16A C16 H16B 106.6 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C16 C17 C18 112.6(3) . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C15 C14 C13 112.9(3) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C26 C25 C24 120.1(4) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C16 C15 C14 125.9(4) . . ?
C16 C15 H15A 105.8 . . ?
C14 C15 H15A 105.8 . . ?
C16 C15 H15B 105.8 . . ?
C14 C15 H15B 105.8 . . ?
H15A C15 H15B 106.2 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.052

#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_CompdS-12
_database_code_depnum_ccdc_archive 'CCDC 1051469'
_audit_update_record             
;
2015-02-26 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H33 N O4 P2'
_chemical_formula_weight         641.60

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   11.326(2)
_cell_length_b                   15.940(3)
_cell_length_c                   17.593(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3176.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9647
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_process_details   'SADABS, SHELDRICK (1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30330
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5582
_reflns_number_gt                5537
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0577P)²+2.7772P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   0.03(9)
_refine_ls_number_reflns         5582
_refine_ls_number_parameters     416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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
P1 P 0.54326(5) 1.07774(4) 0.89799(4) 0.01608(14) Uani 1 1 d . . .
P2 P 0.85898(5) 0.87288(4) 0.89990(4) 0.01720(15) Uani 1 1 d . . .
O1 O 0.44757(16) 1.12823(11) 0.86297(10) 0.0202(4) Uani 1 1 d . . .
O4 O 0.8980(2) 0.94178(16) 0.69910(13) 0.0423(6) Uani 1 1 d . . .
O3 O 1.0843(2) 0.93125(15) 0.67607(14) 0.0438(6) Uani 1 1 d . . .
O2 O 0.86665(16) 0.88302(12) 0.98356(10) 0.0249(4) Uani 1 1 d . . .
N1 N 1.0012(2) 0.95928(17) 0.71282(15) 0.0319(6) Uani 1 1 d . . .
C19 C 0.6229(2) 1.01758(15) 0.82593(14) 0.0167(5) Uani 1 1 d . . .
C20 C 0.7332(2) 0.99839(15) 0.83729(13) 0.0176(5) Uani 1 1 d . . .
C21 C 0.8407(2) 0.97271(16) 0.85022(14) 0.0176(5) Uani 1 1 d . . .
C34 C 0.9486(2) 1.02525(15) 0.83854(15) 0.0209(5) Uani 1 1 d . . .
C35 C 0.9790(2) 1.07990(16) 0.89657(17) 0.0267(6) Uani 1 1 d . . .
H35 H 0.9291 1.0860 0.9382 0.032 Uiso 1 1 calc R . .
C36 C 1.0842(3) 1.12619(19) 0.8931(2) 0.0337(7) Uani 1 1 d . . .
H36 H 1.1032 1.1633 0.9320 0.040 Uiso 1 1 calc R . .
C37 C 1.1597(3) 1.1165(2) 0.83184(18) 0.0356(7) Uani 1 1 d . . .
H37 H 1.2287 1.1481 0.8292 0.043 Uiso 1 1 calc R . .
C38 C 1.1333(3) 1.06063(18) 0.77504(19) 0.0313(7) Uani 1 1 d . . .
H38 H 1.1868 1.0514 0.7358 0.038 Uiso 1 1 calc R . .
C39 C 1.0258(2) 1.01750(17) 0.77640(16) 0.0240(6) Uani 1 1 d . . .
C22 C 0.7361(2) 0.81006(16) 0.86878(14) 0.0185(5) Uani 1 1 d . . .
C23 C 0.7046(2) 0.80324(16) 0.79266(15) 0.0207(5) Uani 1 1 d . . .
H23 H 0.7451 0.8339 0.7560 0.025 Uiso 1 1 calc R . .
C24 C 0.6129(2) 0.75091(17) 0.77128(17) 0.0250(6) Uani 1 1 d . . .
H24 H 0.5925 0.7456 0.7203 0.030 Uiso 1 1 calc R . .
C25 C 0.5514(3) 0.70644(17) 0.82640(17) 0.0285(6) Uani 1 1 d . . .
H25 H 0.4910 0.6703 0.8120 0.034 Uiso 1 1 calc R . .
C26 C 0.5792(2) 0.71535(17) 0.90245(19) 0.0291(6) Uani 1 1 d . . .
H26 H 0.5349 0.6876 0.9392 0.035 Uiso 1 1 calc R . .
C27 C 0.6731(2) 0.76573(16) 0.92391(16) 0.0220(5) Uani 1 1 d . . .
H27 H 0.6941 0.7700 0.9749 0.026 Uiso 1 1 calc R . .
C28 C 0.9936(2) 0.82837(17) 0.86076(15) 0.0211(5) Uani 1 1 d . . .
C33 C 1.0990(2) 0.85092(18) 0.89643(17) 0.0271(6) Uani 1 1 d . . .
H33 H 1.0981 0.8880 0.9372 0.033 Uiso 1 1 calc R . .
C32 C 1.2051(3) 0.8179(2) 0.87101(17) 0.0332(7) Uani 1 1 d . . .
H32 H 1.2752 0.8331 0.8948 0.040 Uiso 1 1 calc R . .
C31 C 1.2074(3) 0.7628(2) 0.81082(17) 0.0351(7) Uani 1 1 d . . .
H31 H 1.2787 0.7402 0.7946 0.042 Uiso 1 1 calc R . .
C30 C 1.1032(3) 0.74118(19) 0.77447(17) 0.0298(6) Uani 1 1 d . . .
H30 H 1.1048 0.7048 0.7332 0.036 Uiso 1 1 calc R . .
C29 C 0.9970(2) 0.77374(17) 0.79961(16) 0.0239(6) Uani 1 1 d . . .
H29 H 0.9273 0.7588 0.7752 0.029 Uiso 1 1 calc R . .
C18 C 0.6054(2) 1.00514(16) 0.68649(15) 0.0226(5) Uani 1 1 d . . .
H18 H 0.6780 1.0323 0.6836 0.027 Uiso 1 1 calc R . .
C17 C 0.5479(3) 0.97887(19) 0.61438(16) 0.0321(7) Uani 1 1 d . . .
H17A H 0.5314 1.0282 0.5839 0.039 Uiso 1 1 calc R . .
H17B H 0.6018 0.9436 0.5859 0.039 Uiso 1 1 calc R . .
C16 C 0.4390(6) 0.9335(5) 0.6271(2) 0.131(3) Uani 1 1 d . . .
H16A H 0.3822 0.9561 0.5913 0.158 Uiso 1 1 calc R . .
H16B H 0.4540 0.8761 0.6115 0.158 Uiso 1 1 calc R . .
C15 C 0.3847(3) 0.9290(4) 0.6921(2) 0.087(2) Uani 1 1 d . . .
H15A H 0.3554 0.8720 0.6966 0.104 Uiso 1 1 calc R . .
H15B H 0.3158 0.9649 0.6882 0.104 Uiso 1 1 calc R . .
C14 C 0.4426(2) 0.94953(19) 0.76591(16) 0.0268(6) Uani 1 1 d . . .
H14A H 0.3910 0.9858 0.7952 0.032 Uiso 1 1 calc R . .
H14B H 0.4542 0.8983 0.7947 0.032 Uiso 1 1 calc R . .
C13 C 0.5586(2) 0.99190(15) 0.75526(14) 0.0179(5) Uani 1 1 d . . .
C1 C 0.4894(2) 1.00347(16) 0.96706(14) 0.0194(5) Uani 1 1 d . . .
C6 C 0.5631(3) 0.94825(17) 1.00559(15) 0.0249(6) Uani 1 1 d . . .
H6 H 0.6440 0.9490 0.9963 0.030 Uiso 1 1 calc R . .
C5 C 0.5168(3) 0.89240(18) 1.05751(17) 0.0314(7) Uani 1 1 d . . .
H5 H 0.5664 0.8559 1.0836 0.038 Uiso 1 1 calc R . .
C4 C 0.3963(3) 0.89076(18) 1.07070(17) 0.0329(7) Uani 1 1 d . . .
H4 H 0.3651 0.8529 1.1056 0.040 Uiso 1 1 calc R . .
C3 C 0.3225(3) 0.9448(2) 1.03253(16) 0.0339(7) Uani 1 1 d . . .
H3 H 0.2416 0.9430 1.0414 0.041 Uiso 1 1 calc R . .
C2 C 0.3683(3) 1.00191(19) 0.98086(15) 0.0277(6) Uani 1 1 d . . .
H2 H 0.3185 1.0390 0.9556 0.033 Uiso 1 1 calc R . .
C7 C 0.6535(2) 1.14202(15) 0.94351(15) 0.0189(5) Uani 1 1 d . . .
C12 C 0.7096(2) 1.20205(17) 0.89925(16) 0.0256(6) Uani 1 1 d . . .
H12 H 0.6923 1.2056 0.8477 0.031 Uiso 1 1 calc R . .
C11 C 0.7912(3) 1.25680(18) 0.93087(19) 0.0312(7) Uani 1 1 d . . .
H11 H 0.8284 1.2969 0.9008 0.037 Uiso 1 1 calc R . .
C10 C 0.8165(3) 1.25111(19) 1.00758(19) 0.0303(7) Uani 1 1 d . . .
H10 H 0.8721 1.2869 1.0290 0.036 Uiso 1 1 calc R . .
C9 C 0.7602(3) 1.19301(18) 1.05252(17) 0.0299(6) Uani 1 1 d . . .
H9 H 0.7772 1.1903 1.1042 0.036 Uiso 1 1 calc R . .
C8 C 0.6775(2) 1.13802(18) 1.02101(15) 0.0247(6) Uani 1 1 d . . .
H8 H 0.6389 1.0991 1.0515 0.030 Uiso 1 1 calc R . .


_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 1.4838(19) . ?
P1 C1 1.803(3) . ?
P1 C7 1.803(3) . ?
P1 C19 1.828(3) . ?
P2 O2 1.4831(19) . ?
P2 C22 1.800(3) . ?
P2 C28 1.818(3) . ?
P2 C21 1.827(3) . ?
O4 N1 1.226(3) . ?
O3 N1 1.226(3) . ?
N1 C39 1.480(4) . ?
C19 C20 1.301(4) . ?
C19 C13 1.498(3) . ?
C20 C21 1.305(4) . ?
C21 C34 1.496(3) . ?
C34 C35 1.385(4) . ?
C34 C39 1.405(4) . ?
C35 C36 1.403(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.385(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.372(5) . ?
C37 H37 0.9300 . ?
C38 C39 1.399(4) . ?
C38 H38 0.9300 . ?
C22 C23 1.390(4) . ?
C22 C27 1.396(4) . ?
C23 C24 1.384(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.388(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.382(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.385(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.385(4) . ?
C28 C33 1.396(4) . ?
C33 C32 1.385(4) . ?
C33 H33 0.9300 . ?
C32 C31 1.376(5) . ?
C32 H32 0.9300 . ?
C31 C30 1.385(4) . ?
C31 H31 0.9300 . ?
C30 C29 1.383(4) . ?
C30 H30 0.9300 . ?
C29 H29 0.9300 . ?
C18 C13 1.338(4) . ?
C18 C17 1.487(4) . ?
C18 H18 0.9300 . ?
C17 C16 1.447(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C16 C15 1.301(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 C14 1.491(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C14 C13 1.489(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C1 C6 1.390(4) . ?
C1 C2 1.393(4) . ?
C6 C5 1.379(4) . ?
C6 H6 0.9300 . ?
C5 C4 1.384(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.375(5) . ?
C4 H4 0.9300 . ?
C3 C2 1.387(4) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C7 C12 1.388(4) . ?
C7 C8 1.392(4) . ?
C12 C11 1.387(4) . ?
C12 H12 0.9300 . ?
C11 C10 1.382(5) . ?
C11 H11 0.9300 . ?
C10 C9 1.375(5) . ?
C10 H10 0.9300 . ?
C9 C8 1.397(4) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?

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 C1 112.90(12) . . ?
O1 P1 C7 112.47(11) . . ?
C1 P1 C7 107.95(12) . . ?
O1 P1 C19 110.92(11) . . ?
C1 P1 C19 106.85(11) . . ?
C7 P1 C19 105.31(11) . . ?
O2 P2 C22 114.07(12) . . ?
O2 P2 C28 111.68(12) . . ?
C22 P2 C28 108.44(12) . . ?
O2 P2 C21 112.73(11) . . ?
C22 P2 C21 104.56(12) . . ?
C28 P2 C21 104.70(12) . . ?
O3 N1 O4 123.0(3) . . ?
O3 N1 C39 118.9(3) . . ?
O4 N1 C39 118.1(2) . . ?
C20 C19 C13 122.0(2) . . ?
C20 C19 P1 119.4(2) . . ?
C13 C19 P1 118.61(18) . . ?
C19 C20 C21 175.1(3) . . ?
C20 C21 C34 124.3(2) . . ?
C20 C21 P2 117.54(19) . . ?
C34 C21 P2 117.43(18) . . ?
C35 C34 C39 118.3(2) . . ?
C35 C34 C21 117.0(2) . . ?
C39 C34 C21 124.5(2) . . ?
C34 C35 C36 120.6(3) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C37 C36 C35 120.0(3) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C38 C37 C36 120.3(3) . . ?
C38 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C37 C38 C39 119.8(3) . . ?
C37 C38 H38 120.1 . . ?
C39 C38 H38 120.1 . . ?
C38 C39 C34 120.8(3) . . ?
C38 C39 N1 117.3(3) . . ?
C34 C39 N1 121.8(2) . . ?
C23 C22 C27 119.9(2) . . ?
C23 C22 P2 122.4(2) . . ?
C27 C22 P2 117.7(2) . . ?
C24 C23 C22 120.1(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.6(3) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.7(3) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 119.9(3) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C22 119.8(3) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
C29 C28 C33 119.2(3) . . ?
C29 C28 P2 124.3(2) . . ?
C33 C28 P2 116.5(2) . . ?
C32 C33 C28 119.9(3) . . ?
C32 C33 H33 120.0 . . ?
C28 C33 H33 120.0 . . ?
C31 C32 C33 120.5(3) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C32 C31 C30 119.9(3) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C29 C30 C31 120.0(3) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C29 C28 120.6(3) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C13 C18 C17 123.6(3) . . ?
C13 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
C16 C17 C18 112.5(3) . . ?
C16 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C15 C16 C17 124.6(4) . . ?
C15 C16 H16A 106.2 . . ?
C17 C16 H16A 106.2 . . ?
C15 C16 H16B 106.2 . . ?
C17 C16 H16B 106.2 . . ?
H16A C16 H16B 106.4 . . ?
C16 C15 C14 123.0(3) . . ?
C16 C15 H15A 106.6 . . ?
C14 C15 H15A 106.6 . . ?
C16 C15 H15B 106.6 . . ?
C14 C15 H15B 106.6 . . ?
H15A C15 H15B 106.5 . . ?
C13 C14 C15 112.2(3) . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C18 C13 C14 122.4(2) . . ?
C18 C13 C19 121.0(2) . . ?
C14 C13 C19 116.7(2) . . ?
C6 C1 C2 119.7(2) . . ?
C6 C1 P1 122.8(2) . . ?
C2 C1 P1 117.5(2) . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C12 C7 C8 119.5(2) . . ?
C12 C7 P1 117.4(2) . . ?
C8 C7 P1 123.0(2) . . ?
C11 C12 C7 120.9(3) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C10 C11 C12 119.2(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C7 C8 C9 119.4(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 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
O1 P1 C19 C20 151.8(2) . . . . ?
C1 P1 C19 C20 -84.8(2) . . . . ?
C7 P1 C19 C20 29.8(2) . . . . ?
O1 P1 C19 C13 -28.2(2) . . . . ?
C1 P1 C19 C13 95.2(2) . . . . ?
C7 P1 C19 C13 -150.13(19) . . . . ?
C13 C19 C20 C21 -78(3) . . . . ?
P1 C19 C20 C21 102(3) . . . . ?
C19 C20 C21 C34 177(100) . . . . ?
C19 C20 C21 P2 -13(3) . . . . ?
O2 P2 C21 C20 -91.0(2) . . . . ?
C22 P2 C21 C20 33.4(2) . . . . ?
C28 P2 C21 C20 147.4(2) . . . . ?
O2 P2 C21 C34 79.4(2) . . . . ?
C22 P2 C21 C34 -156.1(2) . . . . ?
C28 P2 C21 C34 -42.2(2) . . . . ?
C20 C21 C34 C35 82.8(3) . . . . ?
P2 C21 C34 C35 -87.0(3) . . . . ?
C20 C21 C34 C39 -103.0(3) . . . . ?
P2 C21 C34 C39 87.2(3) . . . . ?
C39 C34 C35 C36 0.0(4) . . . . ?
C21 C34 C35 C36 174.5(2) . . . . ?
C34 C35 C36 C37 -0.9(4) . . . . ?
C35 C36 C37 C38 -1.3(4) . . . . ?
C36 C37 C38 C39 4.4(4) . . . . ?
C37 C38 C39 C34 -5.5(4) . . . . ?
C37 C38 C39 N1 178.8(3) . . . . ?
C35 C34 C39 C38 3.2(4) . . . . ?
C21 C34 C39 C38 -170.9(2) . . . . ?
C35 C34 C39 N1 178.7(2) . . . . ?
C21 C34 C39 N1 4.6(4) . . . . ?
O3 N1 C39 C38 22.3(4) . . . . ?
O4 N1 C39 C38 -157.2(3) . . . . ?
O3 N1 C39 C34 -153.4(3) . . . . ?
O4 N1 C39 C34 27.1(4) . . . . ?
O2 P2 C22 C23 170.7(2) . . . . ?
C28 P2 C22 C23 -64.2(2) . . . . ?
C21 P2 C22 C23 47.1(2) . . . . ?
O2 P2 C22 C27 -10.7(2) . . . . ?
C28 P2 C22 C27 114.4(2) . . . . ?
C21 P2 C22 C27 -134.3(2) . . . . ?
C27 C22 C23 C24 -1.7(4) . . . . ?
P2 C22 C23 C24 176.9(2) . . . . ?
C22 C23 C24 C25 1.1(4) . . . . ?
C23 C24 C25 C26 1.5(4) . . . . ?
C24 C25 C26 C27 -3.4(4) . . . . ?
C25 C26 C27 C22 2.7(4) . . . . ?
C23 C22 C27 C26 -0.2(4) . . . . ?
P2 C22 C27 C26 -178.8(2) . . . . ?
O2 P2 C28 C29 145.1(2) . . . . ?
C22 P2 C28 C29 18.6(3) . . . . ?
C21 P2 C28 C29 -92.6(2) . . . . ?
O2 P2 C28 C33 -34.0(2) . . . . ?
C22 P2 C28 C33 -160.5(2) . . . . ?
C21 P2 C28 C33 88.3(2) . . . . ?
C29 C28 C33 C32 -0.7(4) . . . . ?
P2 C28 C33 C32 178.4(2) . . . . ?
C28 C33 C32 C31 -0.1(5) . . . . ?
C33 C32 C31 C30 1.1(5) . . . . ?
C32 C31 C30 C29 -1.2(5) . . . . ?
C31 C30 C29 C28 0.4(4) . . . . ?
C33 C28 C29 C30 0.6(4) . . . . ?
P2 C28 C29 C30 -178.5(2) . . . . ?
C13 C18 C17 C16 -3.1(6) . . . . ?
C18 C17 C16 C15 12.1(10) . . . . ?
C17 C16 C15 C14 -17.3(13) . . . . ?
C16 C15 C14 C13 11.8(9) . . . . ?
C17 C18 C13 C14 -0.4(4) . . . . ?
C17 C18 C13 C19 178.1(2) . . . . ?
C15 C14 C13 C18 -3.1(5) . . . . ?
C15 C14 C13 C19 178.3(3) . . . . ?
C20 C19 C13 C18 -49.0(4) . . . . ?
P1 C19 C13 C18 131.0(2) . . . . ?
C20 C19 C13 C14 129.6(3) . . . . ?
P1 C19 C13 C14 -50.4(3) . . . . ?
O1 P1 C1 C6 178.4(2) . . . . ?
C7 P1 C1 C6 -56.6(2) . . . . ?
C19 P1 C1 C6 56.2(2) . . . . ?
O1 P1 C1 C2 -0.9(2) . . . . ?
C7 P1 C1 C2 124.0(2) . . . . ?
C19 P1 C1 C2 -123.1(2) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
P1 C1 C6 C5 -179.6(2) . . . . ?
C1 C6 C5 C4 0.7(4) . . . . ?
C6 C5 C4 C3 -0.3(5) . . . . ?
C5 C4 C3 C2 -0.5(5) . . . . ?
C4 C3 C2 C1 0.9(4) . . . . ?
C6 C1 C2 C3 -0.5(4) . . . . ?
P1 C1 C2 C3 178.8(2) . . . . ?
O1 P1 C7 C12 -56.9(2) . . . . ?
C1 P1 C7 C12 177.9(2) . . . . ?
C19 P1 C7 C12 64.0(2) . . . . ?
O1 P1 C7 C8 118.2(2) . . . . ?
C1 P1 C7 C8 -7.0(2) . . . . ?
C19 P1 C7 C8 -120.9(2) . . . . ?
C8 C7 C12 C11 1.5(4) . . . . ?
P1 C7 C12 C11 176.7(2) . . . . ?
C7 C12 C11 C10 0.0(4) . . . . ?
C12 C11 C10 C9 -1.1(4) . . . . ?
C11 C10 C9 C8 0.8(4) . . . . ?
C12 C7 C8 C9 -1.8(4) . . . . ?
P1 C7 C8 C9 -176.7(2) . . . . ?
C10 C9 C8 C7 0.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.770
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.061
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
