# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1009218'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 Cl O4 P'
_chemical_formula_sum            'C12 H18 Cl O4 P'
_chemical_formula_weight         292.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   33.100(8)
_cell_length_b                   11.236(2)
_cell_length_c                   8.061(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.58(3)
_cell_angle_gamma                90.00
_cell_volume                     2971.9(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8882
_exptl_absorpt_correction_T_max  0.9267
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10070
_diffrn_reflns_av_R_equivalents  0.1404
_diffrn_reflns_av_unetI/netI     0.0837
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.46
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2622
_reflns_number_gt                1606
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.1331P)²+3.2841P] 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_number_reflns         2622
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0858
_refine_ls_wR_factor_ref         0.2521
_refine_ls_wR_factor_gt          0.2375
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.05768(4) 0.37893(11) 0.17193(16) 0.0434(4) Uani 1 1 d . . .
Cl1 Cl 0.22817(6) 0.0860(2) -0.0629(3) 0.1099(9) Uani 1 1 d . . .
C1 C 0.11695(16) 0.2244(4) 0.1244(6) 0.0486(13) Uani 1 1 d . . .
C2 C 0.11203(17) 0.1612(5) -0.0239(7) 0.0537(13) Uani 1 1 d . . .
C3 C 0.1475(2) 0.1199(5) -0.0822(8) 0.0663(17) Uani 1 1 d . . .
H3 H 0.1458 0.0777 -0.1850 0.080 Uiso 1 1 calc R . .
C4 C 0.1844(2) 0.1410(6) 0.0101(10) 0.077(2) Uani 1 1 d . . .
C5 C 0.18825(19) 0.2034(6) 0.1579(9) 0.0705(17) Uani 1 1 d . . .
H5 H 0.2145 0.2171 0.2178 0.085 Uiso 1 1 calc R . .
C6 C 0.15407(17) 0.2467(5) 0.2205(7) 0.0591(15) Uani 1 1 d . . .
C7 C 0.0708(2) 0.1407(5) -0.1290(7) 0.0620(15) Uani 1 1 d . . .
H7 H 0.0495 0.1575 -0.0551 0.074 Uiso 1 1 calc R . .
C8 C 0.0642(3) 0.2274(7) -0.2717(9) 0.092(2) Uani 1 1 d . . .
H8A H 0.0692 0.3085 -0.2290 0.137 Uiso 1 1 calc R . .
H8B H 0.0361 0.2211 -0.3265 0.137 Uiso 1 1 calc R . .
H8C H 0.0830 0.2093 -0.3526 0.137 Uiso 1 1 calc R . .
C9 C 0.0647(2) 0.0130(6) -0.1887(9) 0.083(2) Uani 1 1 d . . .
H9A H 0.0844 -0.0060 -0.2655 0.125 Uiso 1 1 calc R . .
H9B H 0.0370 0.0034 -0.2469 0.125 Uiso 1 1 calc R . .
H9C H 0.0688 -0.0409 -0.0923 0.125 Uiso 1 1 calc R . .
C10 C 0.15818(18) 0.3142(6) 0.3845(7) 0.0667(16) Uani 1 1 d . . .
H10 H 0.1300 0.3267 0.4136 0.080 Uiso 1 1 calc R . .
C11 C 0.1766(3) 0.4348(8) 0.3684(10) 0.117(3) Uani 1 1 d . . .
H11A H 0.2054 0.4261 0.3542 0.175 Uiso 1 1 calc R . .
H11B H 0.1743 0.4814 0.4696 0.175 Uiso 1 1 calc R . .
H11C H 0.1622 0.4759 0.2709 0.175 Uiso 1 1 calc R . .
C12 C 0.1816(3) 0.2449(9) 0.5262(10) 0.128(3) Uani 1 1 d . . .
H12A H 0.1681 0.1684 0.5384 0.192 Uiso 1 1 calc R . .
H12B H 0.1825 0.2903 0.6303 0.192 Uiso 1 1 calc R . .
H12C H 0.2094 0.2309 0.5017 0.192 Uiso 1 1 calc R . .
O1 O 0.08153(10) 0.2588(3) 0.1912(4) 0.0473(9) Uani 1 1 d . . .
O4 O 0.01853(12) 0.3554(4) 0.0511(5) 0.0571(10) Uani 1 1 d . . .
O2 O 0.04890(10) 0.4173(3) 0.3383(4) 0.0527(9) Uani 1 1 d . . .
O3 O 0.08458(11) 0.4650(3) 0.0873(5) 0.0557(10) Uani 1 1 d . . .
H3A H 0.0706 0.4974 0.0050 0.083 Uiso 1 1 calc R . .
H4A H -0.001(2) 0.365(6) 0.100(8) 0.07(2) Uiso 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 O2 1.474(3) . ?
P1 O3 1.534(4) . ?
P1 O4 1.538(4) . ?
P1 O1 1.561(3) . ?
Cl1 C4 1.746(6) . ?
C1 C2 1.382(7) . ?
C1 C6 1.386(8) . ?
C1 O1 1.407(6) . ?
C2 C3 1.399(8) . ?
C2 C7 1.525(8) . ?
C3 C4 1.367(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(10) . ?
C5 C6 1.386(8) . ?
C5 H5 0.9500 . ?
C6 C10 1.514(8) . ?
C7 C8 1.501(9) . ?
C7 C9 1.519(9) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.499(10) . ?
C10 C12 1.510(10) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O4 H4A 0.80(7) . ?
O3 H3A 0.8400 . ?

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 P1 O3 114.6(2) . . ?
O2 P1 O4 112.1(2) . . ?
O3 P1 O4 108.5(2) . . ?
O2 P1 O1 108.7(2) . . ?
O3 P1 O1 105.89(18) . . ?
O4 P1 O1 106.7(2) . . ?
C2 C1 C6 124.9(5) . . ?
C2 C1 O1 117.6(5) . . ?
C6 C1 O1 117.3(5) . . ?
C1 C2 C3 116.9(6) . . ?
C1 C2 C7 123.6(5) . . ?
C3 C2 C7 119.4(5) . . ?
C4 C3 C2 119.3(6) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 122.3(6) . . ?
C3 C4 Cl1 118.5(6) . . ?
C5 C4 Cl1 119.2(6) . . ?
C4 C5 C6 120.6(6) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 116.0(6) . . ?
C1 C6 C10 123.3(5) . . ?
C5 C6 C10 120.6(6) . . ?
C8 C7 C9 111.7(5) . . ?
C8 C7 C2 111.0(5) . . ?
C9 C7 C2 113.0(5) . . ?
C8 C7 H7 106.9 . . ?
C9 C7 H7 106.9 . . ?
C2 C7 H7 106.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C12 110.9(7) . . ?
C11 C10 C6 111.6(5) . . ?
C12 C10 C6 112.3(6) . . ?
C11 C10 H10 107.2 . . ?
C12 C10 H10 107.2 . . ?
C6 C10 H10 107.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 O1 P1 129.4(3) . . ?
P1 O4 H4A 109(5) . . ?
P1 O3 H3A 109.5 . . ?

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
C6 C1 C2 C3 -1.9(8) . . . . ?
O1 C1 C2 C3 -175.4(4) . . . . ?
C6 C1 C2 C7 -178.4(5) . . . . ?
O1 C1 C2 C7 8.1(7) . . . . ?
C1 C2 C3 C4 1.6(8) . . . . ?
C7 C2 C3 C4 178.3(5) . . . . ?
C2 C3 C4 C5 -1.1(10) . . . . ?
C2 C3 C4 Cl1 178.6(4) . . . . ?
C3 C4 C5 C6 0.8(10) . . . . ?
Cl1 C4 C5 C6 -179.0(5) . . . . ?
C2 C1 C6 C5 1.5(8) . . . . ?
O1 C1 C6 C5 175.0(5) . . . . ?
C2 C1 C6 C10 -178.6(5) . . . . ?
O1 C1 C6 C10 -5.1(8) . . . . ?
C4 C5 C6 C1 -0.9(9) . . . . ?
C4 C5 C6 C10 179.2(6) . . . . ?
C1 C2 C7 C8 98.9(6) . . . . ?
C3 C2 C7 C8 -77.6(7) . . . . ?
C1 C2 C7 C9 -134.7(6) . . . . ?
C3 C2 C7 C9 48.8(7) . . . . ?
C1 C6 C10 C11 -109.1(7) . . . . ?
C5 C6 C10 C11 70.8(8) . . . . ?
C1 C6 C10 C12 125.6(7) . . . . ?
C5 C6 C10 C12 -54.5(9) . . . . ?
C2 C1 O1 P1 -95.4(5) . . . . ?
C6 C1 O1 P1 90.6(6) . . . . ?
O2 P1 O1 C1 -133.1(4) . . . . ?
O3 P1 O1 C1 -9.5(5) . . . . ?
O4 P1 O1 C1 105.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O4 0.80(7) 2.95(7) 3.582(8) 137(6) 2
O3 H3A O2 0.84 1.73 2.559(5) 169.6 6_565
O4 H4A O2 0.80(7) 1.83(7) 2.605(5) 163(7) 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         0.587
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.095
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_Compound2
_database_code_depnum_ccdc_archive 'CCDC 1009219'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 Br O4 P'
_chemical_formula_sum            'C12 H18 Br O4 P'
_chemical_formula_weight         337.14

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'
Br Br -0.2901 2.4595 '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           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   33.434(14)
_cell_length_b                   11.241(5)
_cell_length_c                   7.946(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.374(5)
_cell_angle_gamma                90.00
_cell_volume                     2962(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    2.887
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4681
_exptl_absorpt_correction_T_max  0.7611
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9304
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2749
_reflns_number_gt                2652
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0461P)²+4.7957P] 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_number_reflns         2749
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
Br1 Br 0.730846(8) 0.07885(3) 0.43198(4) 0.04010(13) Uani 1 1 d . . .
P1 P 0.557286(17) 0.37782(5) 0.67124(7) 0.01656(15) Uani 1 1 d . . .
O4 O 0.51838(5) 0.35313(16) 0.5488(2) 0.0236(4) Uani 1 1 d . . .
H4A H 0.4983 0.3784 0.5919 0.028 Uiso 1 1 calc R . .
O1 O 0.58073(5) 0.25712(14) 0.69425(19) 0.0196(3) Uani 1 1 d . . .
O2 O 0.54796(5) 0.41727(14) 0.8413(2) 0.0219(4) Uani 1 1 d . . .
O3 O 0.58433(5) 0.46337(15) 0.5863(2) 0.0233(4) Uani 1 1 d . . .
H3A H 0.5703 0.5003 0.5077 0.028 Uiso 1 1 calc R . .
C4 C 0.68353(8) 0.1386(2) 0.5118(3) 0.0283(6) Uani 1 1 d . . .
C2 C 0.61145(7) 0.1597(2) 0.4749(3) 0.0209(5) Uani 1 1 d . . .
C3 C 0.64672(8) 0.1169(2) 0.4179(3) 0.0251(5) Uani 1 1 d . . .
H9 H 0.6452 0.0732 0.3150 0.030 Uiso 1 1 calc R . .
C5 C 0.68730(8) 0.2011(2) 0.6626(3) 0.0278(5) Uani 1 1 d . . .
H10 H 0.7132 0.2146 0.7240 0.033 Uiso 1 1 calc R . .
C6 C 0.65277(7) 0.2446(2) 0.7247(3) 0.0230(5) Uani 1 1 d . . .
C1 C 0.61600(7) 0.22271(19) 0.6266(3) 0.0197(5) Uani 1 1 d . . .
C10 C 0.57043(7) 0.1401(2) 0.3708(3) 0.0233(5) Uani 1 1 d . . .
H13 H 0.5492 0.1555 0.4463 0.028 Uiso 1 1 calc R . .
C12 C 0.56493(9) 0.0129(2) 0.3041(3) 0.0333(6) Uani 1 1 d . . .
H14A H 0.5832 -0.0013 0.2191 0.040 Uiso 1 1 calc R . .
H14B H 0.5370 0.0016 0.2521 0.040 Uiso 1 1 calc R . .
H14C H 0.5711 -0.0432 0.3983 0.040 Uiso 1 1 calc R . .
C11 C 0.56433(9) 0.2295(2) 0.2242(3) 0.0367(6) Uani 1 1 d . . .
H15A H 0.5674 0.3106 0.2694 0.044 Uiso 1 1 calc R . .
H15B H 0.5372 0.2200 0.1624 0.044 Uiso 1 1 calc R . .
H15C H 0.5844 0.2152 0.1469 0.044 Uiso 1 1 calc R . .
C7 C 0.65631(8) 0.3131(2) 0.8907(3) 0.0287(6) Uani 1 1 d . . .
H16 H 0.6286 0.3197 0.9249 0.034 Uiso 1 1 calc R . .
C9 C 0.68282(11) 0.2485(4) 1.0335(4) 0.0523(9) Uani 1 1 d . . .
H17A H 0.6810 0.2889 1.1415 0.063 Uiso 1 1 calc R . .
H17B H 0.7109 0.2491 1.0100 0.063 Uiso 1 1 calc R . .
H17C H 0.6736 0.1661 1.0403 0.063 Uiso 1 1 calc R . .
C8 C 0.67172(10) 0.4390(3) 0.8680(4) 0.0425(7) Uani 1 1 d . . .
H18A H 0.7002 0.4359 0.8514 0.051 Uiso 1 1 calc R . .
H18B H 0.6687 0.4861 0.9693 0.051 Uiso 1 1 calc R . .
H18C H 0.6561 0.4757 0.7687 0.051 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
Br1 C4 1.901(3) . ?
P1 O2 1.4926(17) . ?
P1 O3 1.5344(17) . ?
P1 O4 1.5462(16) . ?
P1 O1 1.5659(17) . ?
O4 H4A 0.8400 . ?
O1 C1 1.411(3) . ?
O3 H3A 0.8400 . ?
C4 C3 1.377(4) . ?
C4 C5 1.381(4) . ?
C2 C1 1.390(3) . ?
C2 C3 1.401(3) . ?
C2 C10 1.524(3) . ?
C3 H9 0.9500 . ?
C5 C6 1.400(3) . ?
C5 H10 0.9500 . ?
C6 C1 1.391(3) . ?
C6 C7 1.519(3) . ?
C10 C12 1.528(4) . ?
C10 C11 1.533(3) . ?
C10 H13 1.0000 . ?
C12 H14A 0.9800 . ?
C12 H14B 0.9800 . ?
C12 H14C 0.9800 . ?
C11 H15A 0.9800 . ?
C11 H15B 0.9800 . ?
C11 H15C 0.9800 . ?
C7 C8 1.524(4) . ?
C7 C9 1.530(4) . ?
C7 H16 1.0000 . ?
C9 H17A 0.9800 . ?
C9 H17B 0.9800 . ?
C9 H17C 0.9800 . ?
C8 H18A 0.9800 . ?
C8 H18B 0.9800 . ?
C8 H18C 0.9800 . ?

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 P1 O3 114.54(10) . . ?
O2 P1 O4 111.49(10) . . ?
O3 P1 O4 109.35(10) . . ?
O2 P1 O1 108.14(9) . . ?
O3 P1 O1 106.26(9) . . ?
O4 P1 O1 106.62(9) . . ?
P1 O4 H4A 109.5 . . ?
C1 O1 P1 128.55(14) . . ?
P1 O3 H3A 109.5 . . ?
C3 C4 C5 122.4(2) . . ?
C3 C4 Br1 118.76(19) . . ?
C5 C4 Br1 118.8(2) . . ?
C1 C2 C3 116.9(2) . . ?
C1 C2 C10 122.4(2) . . ?
C3 C2 C10 120.7(2) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H9 120.2 . . ?
C2 C3 H9 120.2 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H10 120.1 . . ?
C6 C5 H10 120.1 . . ?
C1 C6 C5 116.7(2) . . ?
C1 C6 C7 122.8(2) . . ?
C5 C6 C7 120.5(2) . . ?
C2 C1 C6 124.6(2) . . ?
C2 C1 O1 117.8(2) . . ?
C6 C1 O1 117.4(2) . . ?
C2 C10 C12 112.5(2) . . ?
C2 C10 C11 109.9(2) . . ?
C12 C10 C11 110.6(2) . . ?
C2 C10 H13 107.9 . . ?
C12 C10 H13 107.9 . . ?
C11 C10 H13 107.9 . . ?
C10 C12 H14A 109.5 . . ?
C10 C12 H14B 109.5 . . ?
H14A C12 H14B 109.5 . . ?
C10 C12 H14C 109.5 . . ?
H14A C12 H14C 109.5 . . ?
H14B C12 H14C 109.5 . . ?
C10 C11 H15A 109.5 . . ?
C10 C11 H15B 109.5 . . ?
H15A C11 H15B 109.5 . . ?
C10 C11 H15C 109.5 . . ?
H15A C11 H15C 109.5 . . ?
H15B C11 H15C 109.5 . . ?
C6 C7 C8 111.0(2) . . ?
C6 C7 C9 112.1(2) . . ?
C8 C7 C9 110.9(3) . . ?
C6 C7 H16 107.6 . . ?
C8 C7 H16 107.6 . . ?
C9 C7 H16 107.6 . . ?
C7 C9 H17A 109.5 . . ?
C7 C9 H17B 109.5 . . ?
H17A C9 H17B 109.5 . . ?
C7 C9 H17C 109.5 . . ?
H17A C9 H17C 109.5 . . ?
H17B C9 H17C 109.5 . . ?
C7 C8 H18A 109.5 . . ?
C7 C8 H18B 109.5 . . ?
H18A C8 H18B 109.5 . . ?
C7 C8 H18C 109.5 . . ?
H18A C8 H18C 109.5 . . ?
H18B C8 H18C 109.5 . . ?

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
O2 P1 O1 C1 -133.76(18) . . . . ?
O3 P1 O1 C1 -10.3(2) . . . . ?
O4 P1 O1 C1 106.23(19) . . . . ?
C5 C4 C3 C2 0.3(4) . . . . ?
Br1 C4 C3 C2 179.73(18) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C10 C2 C3 C4 178.2(2) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
Br1 C4 C5 C6 -179.24(18) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C4 C5 C6 C7 179.7(2) . . . . ?
C3 C2 C1 C6 -0.6(3) . . . . ?
C10 C2 C1 C6 -178.9(2) . . . . ?
C3 C2 C1 O1 -174.28(19) . . . . ?
C10 C2 C1 O1 7.4(3) . . . . ?
C5 C6 C1 C2 1.1(3) . . . . ?
C7 C6 C1 C2 -179.5(2) . . . . ?
C5 C6 C1 O1 174.8(2) . . . . ?
C7 C6 C1 O1 -5.8(3) . . . . ?
P1 O1 C1 C2 -94.3(2) . . . . ?
P1 O1 C1 C6 91.5(2) . . . . ?
C1 C2 C10 C12 -136.7(2) . . . . ?
C3 C2 C10 C12 45.1(3) . . . . ?
C1 C2 C10 C11 99.6(3) . . . . ?
C3 C2 C10 C11 -78.7(3) . . . . ?
C1 C6 C7 C8 -104.2(3) . . . . ?
C5 C6 C7 C8 75.2(3) . . . . ?
C1 C6 C7 C9 131.3(3) . . . . ?
C5 C6 C7 C9 -49.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O2 0.84 1.76 2.588(2) 171.1 2_656
O3 H3A O2 0.84 1.71 2.542(2) 172.2 6_565
O4 H4A O2 0.84 1.76 2.588(2) 171.1 2_656
O3 H3A O2 0.84 1.71 2.542(2) 172.2 6_565

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_Compound3
_database_code_depnum_ccdc_archive 'CCDC 1009220'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 I O4 P'
_chemical_formula_sum            'C12 H18 I O4 P'
_chemical_formula_weight         384.13

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'
I I -0.4742 1.8119 '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           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   34.091(18)
_cell_length_b                   11.245(6)
_cell_length_c                   8.001(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.511(11)
_cell_angle_gamma                90.00
_cell_volume                     3041(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    2.215
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5027
_exptl_absorpt_correction_T_max  0.9570
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724+'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10903
_diffrn_reflns_av_R_equivalents  0.1054
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2689
_reflns_number_gt                2173
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0'

_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)+(0.1260P)²+13.5850P] 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_number_reflns         2689
_refine_ls_number_parameters     163
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.2136
_refine_ls_wR_factor_gt          0.2019
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.076
_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
C1 C 0.3861(2) 0.7753(6) 0.3729(8) 0.0146(14) Uani 1 1 d U . .
C2 C 0.3904(2) 0.8394(6) 0.5230(8) 0.0149(14) Uani 1 1 d . . .
C3 C 0.3553(2) 0.8805(6) 0.5793(9) 0.0193(15) Uani 1 1 d . . .
H3 H 0.3566 0.9237 0.6819 0.023 Uiso 1 1 calc R . .
C4 C 0.3197(2) 0.8586(7) 0.4873(9) 0.0202(16) Uani 1 1 d . . .
C5 C 0.3159(2) 0.7958(7) 0.3364(9) 0.0219(16) Uani 1 1 d . . .
H5 H 0.2905 0.7824 0.2750 0.026 Uiso 1 1 calc R . .
C6 C 0.3499(2) 0.7525(6) 0.2754(9) 0.0172(15) Uani 1 1 d . . .
C7 C 0.3469(2) 0.6844(7) 0.1105(9) 0.0224(16) Uani 1 1 d . . .
H7 H 0.3740 0.6800 0.0760 0.027 Uiso 1 1 calc R . .
C8 C 0.3199(3) 0.7486(10) -0.0308(10) 0.047(3) Uani 1 1 d . . .
H8A H 0.3297 0.8297 -0.0433 0.070 Uiso 1 1 calc R . .
H8B H 0.2929 0.7516 -0.0020 0.070 Uiso 1 1 calc R . .
H8C H 0.3201 0.7053 -0.1370 0.070 Uiso 1 1 calc R . .
C9 C 0.3327(3) 0.5589(7) 0.1314(11) 0.033(2) Uani 1 1 d . . .
H9A H 0.3311 0.5171 0.0233 0.050 Uiso 1 1 calc R . .
H9B H 0.3065 0.5607 0.1692 0.050 Uiso 1 1 calc R . .
H9C H 0.3514 0.5175 0.2154 0.050 Uiso 1 1 calc R . .
C10 C 0.4299(2) 0.8589(6) 0.6288(9) 0.0173(15) Uani 1 1 d . . .
H10 H 0.4508 0.8435 0.5547 0.021 Uiso 1 1 calc R . .
C11 C 0.4355(2) 0.9876(7) 0.6932(10) 0.0275(18) Uani 1 1 d . . .
H11A H 0.4314 1.0426 0.5975 0.041 Uiso 1 1 calc R . .
H11B H 0.4623 0.9974 0.7522 0.041 Uiso 1 1 calc R . .
H11C H 0.4162 1.0047 0.7708 0.041 Uiso 1 1 calc R . .
C12 C 0.4363(3) 0.7712(7) 0.7727(10) 0.033(2) Uani 1 1 d . . .
H12A H 0.4622 0.7857 0.8387 0.049 Uiso 1 1 calc R . .
H12B H 0.4355 0.6901 0.7276 0.049 Uiso 1 1 calc R . .
H12C H 0.4155 0.7810 0.8451 0.049 Uiso 1 1 calc R . .
I1 I 0.268040(18) 0.92433(6) 0.57128(8) 0.0419(3) Uani 1 1 d . . .
O2 O 0.45290(14) 0.5816(4) 0.1599(6) 0.0146(11) Uani 1 1 d . . .
O3 O 0.41788(13) 0.5362(4) 0.4151(6) 0.0174(11) Uani 1 1 d . . .
H3A H 0.4293 0.4701 0.4294 0.026 Uiso 1 1 calc R . .
O4 O 0.48239(13) 0.6479(5) 0.4495(5) 0.0168(10) Uani 1 1 d . . .
H4 H 0.4961 0.5858 0.4623 0.025 Uiso 1 1 calc R . .
P1 P 0.44392(5) 0.62197(15) 0.3295(2) 0.0113(4) Uani 1 1 d . . .
O1 O 0.42066(12) 0.7428(4) 0.3060(5) 0.0113(10) Uani 1 1 d U . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.392(9) . ?
C1 C6 1.395(9) . ?
C1 O1 1.406(8) . ?
C2 C3 1.410(10) . ?
C2 C10 1.510(10) . ?
C3 C4 1.358(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(10) . ?
C4 I1 2.099(7) . ?
C5 C6 1.401(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.517(10) . ?
C7 C9 1.507(11) . ?
C7 C8 1.540(11) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C12 1.510(10) . ?
C10 C11 1.539(10) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O2 P1 1.500(5) . ?
O3 P1 1.531(5) . ?
O3 H3A 0.8400 . ?
O4 P1 1.548(4) . ?
O4 H4 0.8400 . ?
P1 O1 1.572(5) . ?

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
C2 C1 C6 124.4(6) . . ?
C2 C1 O1 117.6(6) . . ?
C6 C1 O1 117.6(6) . . ?
C1 C2 C3 116.5(6) . . ?
C1 C2 C10 123.1(6) . . ?
C3 C2 C10 120.4(6) . . ?
C4 C3 C2 120.3(7) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 122.4(6) . . ?
C3 C4 I1 119.4(5) . . ?
C5 C4 I1 118.1(5) . . ?
C4 C5 C6 119.6(6) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 116.8(6) . . ?
C1 C6 C7 122.3(6) . . ?
C5 C6 C7 120.9(6) . . ?
C9 C7 C6 111.2(6) . . ?
C9 C7 C8 110.6(7) . . ?
C6 C7 C8 111.6(7) . . ?
C9 C7 H7 107.8 . . ?
C6 C7 H7 107.8 . . ?
C8 C7 H7 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C10 C2 111.2(6) . . ?
C12 C10 C11 111.1(6) . . ?
C2 C10 C11 112.7(6) . . ?
C12 C10 H10 107.2 . . ?
C2 C10 H10 107.2 . . ?
C11 C10 H10 107.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
P1 O3 H3A 109.5 . . ?
P1 O4 H4 109.5 . . ?
O2 P1 O3 114.4(3) . . ?
O2 P1 O4 111.2(3) . . ?
O3 P1 O4 109.6(3) . . ?
O2 P1 O1 108.2(3) . . ?
O3 P1 O1 106.6(3) . . ?
O4 P1 O1 106.5(3) . . ?
C1 O1 P1 127.9(4) . . ?

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
C6 C1 C2 C3 1.6(10) . . . . ?
O1 C1 C2 C3 174.2(6) . . . . ?
C6 C1 C2 C10 177.9(6) . . . . ?
O1 C1 C2 C10 -9.5(9) . . . . ?
C1 C2 C3 C4 -1.0(10) . . . . ?
C10 C2 C3 C4 -177.3(6) . . . . ?
C2 C3 C4 C5 0.1(11) . . . . ?
C2 C3 C4 I1 -178.6(5) . . . . ?
C3 C4 C5 C6 0.3(11) . . . . ?
I1 C4 C5 C6 178.9(5) . . . . ?
C2 C1 C6 C5 -1.3(10) . . . . ?
O1 C1 C6 C5 -173.9(6) . . . . ?
C2 C1 C6 C7 178.6(6) . . . . ?
O1 C1 C6 C7 5.9(9) . . . . ?
C4 C5 C6 C1 0.3(10) . . . . ?
C4 C5 C6 C7 -179.6(7) . . . . ?
C1 C6 C7 C9 103.9(8) . . . . ?
C5 C6 C7 C9 -76.3(9) . . . . ?
C1 C6 C7 C8 -132.1(8) . . . . ?
C5 C6 C7 C8 47.7(10) . . . . ?
C1 C2 C10 C12 -98.1(8) . . . . ?
C3 C2 C10 C12 78.0(8) . . . . ?
C1 C2 C10 C11 136.4(7) . . . . ?
C3 C2 C10 C11 -47.5(9) . . . . ?
C2 C1 O1 P1 95.3(7) . . . . ?
C6 C1 O1 P1 -91.5(6) . . . . ?
O2 P1 O1 C1 133.1(5) . . . . ?
O3 P1 O1 C1 9.6(6) . . . . ?
O4 P1 O1 C1 -107.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.344
_refine_diff_density_min         -2.175
_refine_diff_density_rms         0.214
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_Compound5
_database_code_depnum_ccdc_archive 'CCDC 1009227'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H27 O4 P'
_chemical_formula_sum            'C20 H27 O4 P'
_chemical_formula_weight         362.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   33.710(16)
_cell_length_b                   6.824(3)
_cell_length_c                   17.253(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.834(8)
_cell_angle_gamma                90.00
_cell_volume                     3968(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_T_max  0.9690
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14827
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3692
_reflns_number_gt                3510
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0734P)²+7.8369P] 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_number_reflns         3692
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1702
_refine_ls_wR_factor_gt          0.1676
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_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 0.44621(2) -0.45493(10) 0.58210(4) 0.0282(2) Uani 1 1 d . . .
O1 O 0.40407(5) -0.4480(3) 0.62091(10) 0.0306(4) Uani 1 1 d . . .
O3 O 0.47125(5) -0.5391(3) 0.65193(11) 0.0356(5) Uani 1 1 d . . .
O4 O 0.44309(6) -0.6223(3) 0.52062(10) 0.0340(5) Uani 1 1 d . . .
O2 O 0.45957(6) -0.2732(3) 0.54791(13) 0.0436(5) Uani 1 1 d . . .
C4 C 0.33158(8) 0.0455(4) 0.64381(15) 0.0297(6) Uani 1 1 d . . .
C3 C 0.35880(8) -0.0082(4) 0.70202(15) 0.0329(6) Uani 1 1 d . . .
H3 H 0.3602 0.0680 0.7481 0.040 Uiso 1 1 calc R . .
C5 C 0.33040(8) -0.0679(4) 0.57640(15) 0.0292(6) Uani 1 1 d . . .
H5 H 0.3122 -0.0333 0.5361 0.035 Uiso 1 1 calc R . .
C13 C 0.30431(8) 0.2148(4) 0.65391(15) 0.0312(6) Uani 1 1 d . . .
C1 C 0.38108(8) -0.2756(4) 0.62664(15) 0.0279(6) Uani 1 1 d . . .
C18 C 0.26567(9) 0.2092(4) 0.62450(18) 0.0384(7) Uani 1 1 d . . .
H18 H 0.2568 0.0969 0.5967 0.046 Uiso 1 1 calc R . .
C7 C 0.35250(8) -0.3479(4) 0.49192(15) 0.0318(6) Uani 1 1 d . . .
H7 H 0.3696 -0.4664 0.4991 0.038 Uiso 1 1 calc R . .
C14 C 0.31673(9) 0.3825(4) 0.69384(16) 0.0354(6) Uani 1 1 d . . .
H14 H 0.3431 0.3899 0.7139 0.042 Uiso 1 1 calc R . .
C6 C 0.35482(8) -0.2294(4) 0.56616(14) 0.0275(6) Uani 1 1 d . . .
C17 C 0.23988(9) 0.3647(5) 0.63511(19) 0.0434(7) Uani 1 1 d . . .
H17 H 0.2136 0.3583 0.6149 0.052 Uiso 1 1 calc R . .
C15 C 0.29095(10) 0.5380(4) 0.70448(18) 0.0432(7) Uani 1 1 d . . .
H15 H 0.2997 0.6510 0.7320 0.052 Uiso 1 1 calc R . .
C10 C 0.41198(9) -0.2250(5) 0.76072(16) 0.0409(7) Uani 1 1 d . . .
H10 H 0.4268 -0.3447 0.7444 0.049 Uiso 1 1 calc R . .
C2 C 0.38382(8) -0.1684(4) 0.69504(15) 0.0320(6) Uani 1 1 d . . .
C11 C 0.38949(10) -0.2748(5) 0.83323(18) 0.0488(8) Uani 1 1 d . . .
H11A H 0.4083 -0.3118 0.8745 0.073 Uiso 1 1 calc R . .
H11B H 0.3714 -0.3843 0.8225 0.073 Uiso 1 1 calc R . .
H11C H 0.3742 -0.1604 0.8497 0.073 Uiso 1 1 calc R . .
C8 C 0.31088(10) -0.4178(6) 0.4733(2) 0.0544(9) Uani 1 1 d . . .
H8A H 0.3110 -0.4943 0.4252 0.082 Uiso 1 1 calc R . .
H8B H 0.2933 -0.3044 0.4668 0.082 Uiso 1 1 calc R . .
H8C H 0.3014 -0.4998 0.5158 0.082 Uiso 1 1 calc R . .
C16 C 0.25259(10) 0.5300(5) 0.67537(19) 0.0439(7) Uani 1 1 d . . .
H16 H 0.2350 0.6369 0.6829 0.053 Uiso 1 1 calc R . .
C19 C 0.51295(9) -0.5816(6) 0.63997(19) 0.0515(9) Uani 1 1 d . . .
H19A H 0.5248 -0.6327 0.6881 0.077 Uiso 1 1 calc R . .
H19B H 0.5267 -0.4613 0.6250 0.077 Uiso 1 1 calc R . .
H19C H 0.5155 -0.6795 0.5988 0.077 Uiso 1 1 calc R . .
C9 C 0.36923(14) -0.2297(6) 0.4257(2) 0.0637(11) Uani 1 1 d . . .
H9A H 0.3679 -0.3074 0.3780 0.096 Uiso 1 1 calc R . .
H9B H 0.3969 -0.1959 0.4375 0.096 Uiso 1 1 calc R . .
H9C H 0.3537 -0.1095 0.4189 0.096 Uiso 1 1 calc R . .
C12 C 0.44217(12) -0.0635(8) 0.7767(3) 0.0848(16) Uani 1 1 d . . .
H12A H 0.4601 -0.1041 0.8190 0.127 Uiso 1 1 calc R . .
H12B H 0.4283 0.0568 0.7916 0.127 Uiso 1 1 calc R . .
H12C H 0.4575 -0.0391 0.7299 0.127 Uiso 1 1 calc R . .
C20 C 0.43423(14) -0.8224(5) 0.5413(2) 0.0649(11) Uani 1 1 d . . .
H20A H 0.4335 -0.9036 0.4945 0.097 Uiso 1 1 calc R . .
H20B H 0.4084 -0.8278 0.5665 0.097 Uiso 1 1 calc R . .
H20C H 0.4548 -0.8717 0.5770 0.097 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 O2 1.448(2) . ?
P1 O4 1.561(2) . ?
P1 O3 1.570(2) . ?
P1 O1 1.580(2) . ?
O1 C1 1.413(3) . ?
O3 C19 1.453(3) . ?
O4 C20 1.444(4) . ?
C4 C5 1.397(4) . ?
C4 C3 1.399(4) . ?
C4 C13 1.488(4) . ?
C3 C2 1.387(4) . ?
C3 H3 0.9500 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C13 C18 1.391(4) . ?
C13 C14 1.397(4) . ?
C1 C2 1.391(4) . ?
C1 C6 1.395(4) . ?
C18 C17 1.386(4) . ?
C18 H18 0.9500 . ?
C7 C8 1.512(4) . ?
C7 C9 1.514(4) . ?
C7 C6 1.516(4) . ?
C7 H7 1.0000 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9500 . ?
C17 C16 1.389(5) . ?
C17 H17 0.9500 . ?
C15 C16 1.381(5) . ?
C15 H15 0.9500 . ?
C10 C11 1.511(4) . ?
C10 C2 1.517(4) . ?
C10 C12 1.523(5) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C16 H16 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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 P1 O4 111.60(12) . . ?
O2 P1 O3 117.32(13) . . ?
O4 P1 O3 106.50(11) . . ?
O2 P1 O1 115.71(11) . . ?
O4 P1 O1 104.94(11) . . ?
O3 P1 O1 99.36(10) . . ?
C1 O1 P1 123.51(16) . . ?
C19 O3 P1 118.34(18) . . ?
C20 O4 P1 122.4(2) . . ?
C5 C4 C3 117.6(2) . . ?
C5 C4 C13 121.2(2) . . ?
C3 C4 C13 121.3(2) . . ?
C2 C3 C4 122.5(2) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C6 C5 C4 122.4(2) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C18 C13 C14 118.3(3) . . ?
C18 C13 C4 120.8(3) . . ?
C14 C13 C4 120.8(2) . . ?
C2 C1 C6 123.3(2) . . ?
C2 C1 O1 117.9(2) . . ?
C6 C1 O1 118.6(2) . . ?
C17 C18 C13 121.1(3) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C8 C7 C9 111.2(3) . . ?
C8 C7 C6 112.6(2) . . ?
C9 C7 C6 109.7(2) . . ?
C8 C7 H7 107.7 . . ?
C9 C7 H7 107.7 . . ?
C6 C7 H7 107.7 . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C5 C6 C1 117.1(2) . . ?
C5 C6 C7 120.5(2) . . ?
C1 C6 C7 122.4(2) . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C11 C10 C2 111.1(3) . . ?
C11 C10 C12 110.8(3) . . ?
C2 C10 C12 111.1(3) . . ?
C11 C10 H10 107.9 . . ?
C2 C10 H10 107.9 . . ?
C12 C10 H10 107.9 . . ?
C3 C2 C1 117.1(2) . . ?
C3 C2 C10 120.7(2) . . ?
C1 C2 C10 122.2(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
O2 P1 O1 C1 -3.3(2) . . . . ?
O4 P1 O1 C1 -126.8(2) . . . . ?
O3 P1 O1 C1 123.2(2) . . . . ?
O2 P1 O3 C19 -58.2(3) . . . . ?
O4 P1 O3 C19 67.6(2) . . . . ?
O1 P1 O3 C19 176.3(2) . . . . ?
O2 P1 O4 C20 173.7(3) . . . . ?
O3 P1 O4 C20 44.5(3) . . . . ?
O1 P1 O4 C20 -60.2(3) . . . . ?
C5 C4 C3 C2 -0.6(4) . . . . ?
C13 C4 C3 C2 178.2(2) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C13 C4 C5 C6 -178.4(2) . . . . ?
C5 C4 C13 C18 35.4(4) . . . . ?
C3 C4 C13 C18 -143.4(3) . . . . ?
C5 C4 C13 C14 -145.3(3) . . . . ?
C3 C4 C13 C14 35.9(4) . . . . ?
P1 O1 C1 C2 -95.3(3) . . . . ?
P1 O1 C1 C6 89.2(3) . . . . ?
C14 C13 C18 C17 -0.7(4) . . . . ?
C4 C13 C18 C17 178.7(3) . . . . ?
C18 C13 C14 C15 0.7(4) . . . . ?
C4 C13 C14 C15 -178.6(3) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C5 C6 C7 -179.9(2) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
O1 C1 C6 C5 174.9(2) . . . . ?
C2 C1 C6 C7 179.7(2) . . . . ?
O1 C1 C6 C7 -5.1(4) . . . . ?
C8 C7 C6 C5 -54.0(4) . . . . ?
C9 C7 C6 C5 70.5(4) . . . . ?
C8 C7 C6 C1 126.1(3) . . . . ?
C9 C7 C6 C1 -109.4(3) . . . . ?
C13 C18 C17 C16 0.3(5) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
C4 C3 C2 C1 0.4(4) . . . . ?
C4 C3 C2 C10 -178.1(3) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
O1 C1 C2 C3 -175.2(2) . . . . ?
C6 C1 C2 C10 178.5(3) . . . . ?
O1 C1 C2 C10 3.3(4) . . . . ?
C11 C10 C2 C3 60.8(4) . . . . ?
C12 C10 C2 C3 -63.0(4) . . . . ?
C11 C10 C2 C1 -117.5(3) . . . . ?
C12 C10 C2 C1 118.7(4) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C18 C17 C16 C15 0.1(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.084
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_Compound7
_database_code_depnum_ccdc_archive 'CCDC 1009228'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H48 N O4 P'
_chemical_formula_sum            'C39 H48 N O4 P'
_chemical_formula_weight         625.75

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'


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

_cell_length_a                   13.664(9)
_cell_length_b                   10.956(6)
_cell_length_c                   23.642(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.563(12)
_cell_angle_gamma                90.00
_cell_volume                     3500(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9767
_exptl_absorpt_correction_T_max  0.9767
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5027
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.1097
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3909
_reflns_number_gt                2793
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_publication_material  'CrystalStructure 4.0'

_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)+(0.0402P)²+13.7784P] 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_number_reflns         3909
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1581
_refine_ls_R_factor_gt           0.1244
_refine_ls_wR_factor_ref         0.2577
_refine_ls_wR_factor_gt          0.2379
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_restrained_S_all      1.211
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.003

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 0.4143(2) 0.49962(18) 0.10309(9) 0.0348(9) Uani 1 1 d . . .
O1 O 0.4933(6) 0.3935(4) 0.1195(2) 0.034(2) Uani 1 1 d . . .
O3 O 0.3377(7) 0.4327(5) 0.0585(2) 0.048(3) Uani 1 1 d . . .
O2 O 0.3776(6) 0.5595(5) 0.1504(2) 0.041(2) Uani 1 1 d . . .
O4 O 0.4653(6) 0.5861(5) 0.0642(2) 0.043(2) Uani 1 1 d . . .
N1 N 1.0712(6) 0.4143(5) 0.4253(3) 0.022(2) Uani 1 1 d . . .
C39 C 1.3300(9) 0.4187(6) 0.4777(4) 0.040(4) Uani 1 1 d . . .
H5 H 1.3533 0.3854 0.4451 0.048 Uiso 1 1 calc R . .
C27 C 1.1603(8) 0.4355(6) 0.4203(3) 0.026(3) Uani 1 1 d . . .
C5 C 0.6467(9) 0.3588(6) 0.2600(3) 0.032(4) Uani 1 1 d . . .
H7 H 0.6419 0.3281 0.2970 0.039 Uiso 1 1 calc R . .
C1 C 0.5752(8) 0.4024(6) 0.1645(3) 0.031(3) Uani 1 1 d . . .
C2 C 0.6648(9) 0.4439(6) 0.1503(3) 0.034(4) Uani 1 1 d . . .
C17 C 0.9381(8) 0.3015(6) 0.3678(3) 0.025(3) Uani 1 1 d . . .
C3 C 0.7452(8) 0.4454(6) 0.1941(3) 0.028(3) Uani 1 1 d . . .
H13 H 0.8069 0.4763 0.1865 0.033 Uiso 1 1 calc R . .
C28 C 1.1994(8) 0.4542(6) 0.3652(3) 0.028(3) Uani 1 1 d . . .
C4 C 0.7376(8) 0.4029(6) 0.2486(3) 0.025(3) Uani 1 1 d . . .
C6 C 0.5631(8) 0.3584(6) 0.2188(3) 0.029(3) Uani 1 1 d . . .
C16 C 0.9913(8) 0.4125(6) 0.3789(3) 0.027(3) Uani 1 1 d . . .
C13 C 0.8270(9) 0.4061(7) 0.2942(3) 0.034(3) Uani 1 1 d . . .
C34 C 1.2309(9) 0.4509(6) 0.4743(3) 0.027(3) Uani 1 1 d . . .
C14 C 0.8784(8) 0.5128(6) 0.3064(3) 0.029(3) Uani 1 1 d . . .
H20 H 0.8570 0.5845 0.2855 0.035 Uiso 1 1 calc R . .
C18 C 0.8572(9) 0.3009(6) 0.3257(3) 0.036(3) Uani 1 1 d . . .
H21 H 0.8209 0.2274 0.3178 0.043 Uiso 1 1 calc R . .
C33 C 1.2628(9) 0.5524(6) 0.3594(4) 0.034(3) Uani 1 1 d . . .
H22 H 1.2870 0.6007 0.3918 0.041 Uiso 1 1 calc R . .
C22 C 1.0128(8) 0.6420(6) 0.3625(3) 0.035(3) Uani 1 1 d . . .
H23 H 1.0757 0.6267 0.3890 0.042 Uiso 1 1 calc R . .
C19 C 0.9719(9) 0.1866(6) 0.4007(3) 0.045(4) Uani 1 1 d . . .
H24 H 1.0394 0.2025 0.4221 0.054 Uiso 1 1 calc R . .
C15 C 0.9608(9) 0.5188(6) 0.3482(3) 0.033(3) Uani 1 1 d . . .
C11 C 0.7594(11) 0.4031(8) 0.0689(4) 0.053(5) Uani 1 1 d . . .
H26A H 0.7335 0.3202 0.0617 0.063 Uiso 1 1 calc R . .
H26B H 0.8189 0.4003 0.0977 0.063 Uiso 1 1 calc R . .
H26C H 0.7760 0.4378 0.0334 0.063 Uiso 1 1 calc R . .
C10 C 0.6822(9) 0.4811(7) 0.0905(3) 0.033(3) Uani 1 1 d . . .
H27 H 0.6185 0.4699 0.0640 0.039 Uiso 1 1 calc R . .
C7 C 0.4650(8) 0.3083(6) 0.2310(3) 0.037(4) Uani 1 1 d . . .
H28 H 0.4114 0.3631 0.2121 0.044 Uiso 1 1 calc R . .
C32 C 1.2903(9) 0.5794(7) 0.3074(4) 0.045(4) Uani 1 1 d . . .
H29 H 1.3304 0.6489 0.3037 0.054 Uiso 1 1 calc R . .
C29 C 1.1673(9) 0.3818(6) 0.3176(3) 0.038(3) Uani 1 1 d . . .
H30 H 1.1245 0.3146 0.3207 0.045 Uiso 1 1 calc R . .
C35 C 1.1986(9) 0.5011(7) 0.5217(3) 0.038(3) Uani 1 1 d . . .
H31 H 1.1309 0.5226 0.5200 0.045 Uiso 1 1 calc R . .
C23 C 0.9442(10) 0.7210(7) 0.3941(4) 0.046(4) Uani 1 1 d . . .
H32A H 0.9300 0.6775 0.4282 0.055 Uiso 1 1 calc R . .
H32B H 0.8822 0.7370 0.3686 0.055 Uiso 1 1 calc R . .
H32C H 0.9771 0.7986 0.4055 0.055 Uiso 1 1 calc R . .
C24 C 1.0379(9) 0.7064(7) 0.3092(3) 0.038(3) Uani 1 1 d . . .
H33A H 1.0754 0.7810 0.3204 0.046 Uiso 1 1 calc R . .
H33B H 0.9767 0.7275 0.2840 0.046 Uiso 1 1 calc R . .
H33C H 1.0779 0.6521 0.2889 0.046 Uiso 1 1 calc R . .
C9 C 0.4579(10) 0.3047(8) 0.2937(3) 0.047(4) Uani 1 1 d . . .
H34A H 0.4650 0.3875 0.3094 0.056 Uiso 1 1 calc R . .
H34B H 0.5106 0.2526 0.3134 0.056 Uiso 1 1 calc R . .
H34C H 0.3934 0.2715 0.2992 0.056 Uiso 1 1 calc R . .
C21 C 0.9793(11) 0.0782(7) 0.3620(4) 0.064(5) Uani 1 1 d . . .
H35A H 1.0251 0.0180 0.3819 0.076 Uiso 1 1 calc R . .
H35B H 1.0039 0.1052 0.3272 0.076 Uiso 1 1 calc R . .
H35C H 0.9138 0.0411 0.3518 0.076 Uiso 1 1 calc R . .
C8 C 0.4465(10) 0.1807(7) 0.2056(4) 0.052(4) Uani 1 1 d . . .
H36A H 0.4964 0.1242 0.2248 0.063 Uiso 1 1 calc R . .
H36B H 0.4508 0.1831 0.1646 0.063 Uiso 1 1 calc R . .
H36C H 0.3804 0.1529 0.2112 0.063 Uiso 1 1 calc R . .
C37 C 1.3602(11) 0.4874(7) 0.5749(4) 0.050(5) Uani 1 1 d . . .
H37 H 1.4039 0.5008 0.6095 0.060 Uiso 1 1 calc R . .
C25 C 0.2636(10) 0.3532(8) 0.0786(4) 0.052(4) Uani 1 1 d . . .
H38A H 0.2233 0.4011 0.1015 0.063 Uiso 1 1 calc R . .
H38B H 0.2971 0.2876 0.1022 0.063 Uiso 1 1 calc R . .
H38C H 0.2210 0.3179 0.0457 0.063 Uiso 1 1 calc R . .
C26 C 0.4277(10) 0.7074(7) 0.0510(4) 0.050(4) Uani 1 1 d . . .
H39A H 0.3643 0.7023 0.0256 0.060 Uiso 1 1 calc R . .
H39B H 0.4752 0.7533 0.0321 0.060 Uiso 1 1 calc R . .
H39C H 0.4182 0.7491 0.0865 0.060 Uiso 1 1 calc R . .
C38 C 1.3964(9) 0.4349(7) 0.5289(3) 0.043(4) Uani 1 1 d . . .
H40 H 1.4637 0.4105 0.5318 0.051 Uiso 1 1 calc R . .
C31 C 1.2600(11) 0.5061(8) 0.2601(4) 0.049(4) Uani 1 1 d . . .
H41 H 1.2814 0.5229 0.2245 0.059 Uiso 1 1 calc R . .
C30 C 1.1982(10) 0.4084(8) 0.2658(4) 0.045(4) Uani 1 1 d . . .
H42 H 1.1765 0.3584 0.2335 0.054 Uiso 1 1 calc R . .
C20 C 0.9041(14) 0.1575(9) 0.4441(4) 0.085(7) Uani 1 1 d . . .
H43A H 0.8370 0.1426 0.4242 0.102 Uiso 1 1 calc R . .
H43B H 0.9032 0.2265 0.4703 0.102 Uiso 1 1 calc R . .
H43C H 0.9283 0.0845 0.4657 0.102 Uiso 1 1 calc R . .
C36 C 1.2631(11) 0.5205(8) 0.5716(4) 0.048(4) Uani 1 1 d . . .
H44 H 1.2400 0.5569 0.6037 0.058 Uiso 1 1 calc R . .
C12 C 0.7087(10) 0.6171(7) 0.0909(3) 0.046(4) Uani 1 1 d . . .
H45A H 0.7390 0.6411 0.1295 0.056 Uiso 1 1 calc R . .
H45B H 0.6486 0.6652 0.0794 0.056 Uiso 1 1 calc R . .
H45C H 0.7556 0.6318 0.0640 0.056 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 O2 1.449(7) . ?
P1 O3 1.554(6) . ?
P1 O4 1.556(7) . ?
P1 O1 1.595(6) . ?
O1 C1 1.427(10) . ?
O3 C25 1.469(14) . ?
O4 C26 1.442(10) . ?
N1 C27 1.262(14) . ?
N1 C16 1.429(10) . ?
C39 C34 1.389(16) . ?
C39 C38 1.413(11) . ?
C39 H5 0.9500 . ?
C27 C34 1.492(10) . ?
C27 C28 1.492(14) . ?
C5 C6 1.386(12) . ?
C5 C4 1.396(15) . ?
C5 H7 0.9500 . ?
C1 C2 1.394(16) . ?
C1 C6 1.404(12) . ?
C2 C3 1.393(11) . ?
C2 C10 1.524(13) . ?
C17 C18 1.372(12) . ?
C17 C16 1.421(11) . ?
C17 C19 1.515(10) . ?
C3 C4 1.389(11) . ?
C3 H13 0.9500 . ?
C28 C29 1.393(10) . ?
C28 C33 1.401(13) . ?
C4 C13 1.505(12) . ?
C6 C7 1.515(16) . ?
C16 C15 1.402(9) . ?
C13 C14 1.372(12) . ?
C13 C18 1.401(9) . ?
C34 C35 1.378(14) . ?
C14 C15 1.384(12) . ?
C14 H20 0.9500 . ?
C18 H21 0.9500 . ?
C33 C32 1.369(14) . ?
C33 H22 0.9500 . ?
C22 C24 1.528(12) . ?
C22 C15 1.540(11) . ?
C22 C23 1.547(15) . ?
C22 H23 1.0000 . ?
C19 C21 1.512(11) . ?
C19 C20 1.515(19) . ?
C19 H24 1.0000 . ?
C11 C10 1.504(16) . ?
C11 H26A 0.9800 . ?
C11 H26B 0.9800 . ?
C11 H26C 0.9800 . ?
C10 C12 1.533(10) . ?
C10 H27 1.0000 . ?
C7 C9 1.500(13) . ?
C7 C8 1.527(10) . ?
C7 H28 1.0000 . ?
C32 C31 1.389(12) . ?
C32 H29 0.9500 . ?
C29 C30 1.386(14) . ?
C29 H30 0.9500 . ?
C35 C36 1.381(12) . ?
C35 H31 0.9500 . ?
C23 H32A 0.9800 . ?
C23 H32B 0.9800 . ?
C23 H32C 0.9800 . ?
C24 H33A 0.9800 . ?
C24 H33B 0.9800 . ?
C24 H33C 0.9800 . ?
C9 H34A 0.9800 . ?
C9 H34B 0.9800 . ?
C9 H34C 0.9800 . ?
C21 H35A 0.9800 . ?
C21 H35B 0.9800 . ?
C21 H35C 0.9800 . ?
C8 H36A 0.9800 . ?
C8 H36B 0.9800 . ?
C8 H36C 0.9800 . ?
C37 C36 1.37(2) . ?
C37 C38 1.385(15) . ?
C37 H37 0.9500 . ?
C25 H38A 0.9800 . ?
C25 H38B 0.9800 . ?
C25 H38C 0.9800 . ?
C26 H39A 0.9800 . ?
C26 H39B 0.9800 . ?
C26 H39C 0.9800 . ?
C38 H40 0.9500 . ?
C31 C30 1.383(17) . ?
C31 H41 0.9500 . ?
C30 H42 0.9500 . ?
C20 H43A 0.9800 . ?
C20 H43B 0.9800 . ?
C20 H43C 0.9800 . ?
C36 H44 0.9500 . ?
C12 H45A 0.9800 . ?
C12 H45B 0.9800 . ?
C12 H45C 0.9800 . ?

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 P1 O3 117.5(5) . . ?
O2 P1 O4 114.7(4) . . ?
O3 P1 O4 101.6(4) . . ?
O2 P1 O1 116.2(3) . . ?
O3 P1 O1 100.6(3) . . ?
O4 P1 O1 104.0(4) . . ?
C1 O1 P1 124.0(4) . . ?
C25 O3 P1 119.1(6) . . ?
C26 O4 P1 120.8(8) . . ?
C27 N1 C16 124.6(8) . . ?
C34 C39 C38 121.0(10) . . ?
C34 C39 H5 119.5 . . ?
C38 C39 H5 119.5 . . ?
N1 C27 C34 116.7(9) . . ?
N1 C27 C28 125.7(7) . . ?
C34 C27 C28 117.5(10) . . ?
C6 C5 C4 122.0(8) . . ?
C6 C5 H7 119.0 . . ?
C4 C5 H7 119.0 . . ?
C2 C1 C6 124.0(8) . . ?
C2 C1 O1 117.6(8) . . ?
C6 C1 O1 118.1(9) . . ?
C1 C2 C3 116.7(8) . . ?
C1 C2 C10 125.1(8) . . ?
C3 C2 C10 118.2(10) . . ?
C18 C17 C16 118.2(6) . . ?
C18 C17 C19 121.2(7) . . ?
C16 C17 C19 120.5(7) . . ?
C4 C3 C2 121.8(10) . . ?
C4 C3 H13 119.1 . . ?
C2 C3 H13 119.1 . . ?
C29 C28 C33 118.8(9) . . ?
C29 C28 C27 121.0(8) . . ?
C33 C28 C27 119.9(7) . . ?
C3 C4 C5 119.1(8) . . ?
C3 C4 C13 119.5(10) . . ?
C5 C4 C13 121.4(8) . . ?
C5 C6 C1 116.4(10) . . ?
C5 C6 C7 121.8(8) . . ?
C1 C6 C7 121.8(7) . . ?
C15 C16 C17 120.7(7) . . ?
C15 C16 N1 121.4(6) . . ?
C17 C16 N1 117.7(6) . . ?
C14 C13 C18 119.2(8) . . ?
C14 C13 C4 120.4(6) . . ?
C18 C13 C4 120.3(8) . . ?
C35 C34 C39 118.8(8) . . ?
C35 C34 C27 119.8(10) . . ?
C39 C34 C27 121.4(9) . . ?
C13 C14 C15 121.8(7) . . ?
C13 C14 H20 119.1 . . ?
C15 C14 H20 119.1 . . ?
C17 C18 C13 121.5(8) . . ?
C17 C18 H21 119.2 . . ?
C13 C18 H21 119.2 . . ?
C32 C33 C28 120.7(8) . . ?
C32 C33 H22 119.6 . . ?
C28 C33 H22 119.6 . . ?
C24 C22 C15 112.1(6) . . ?
C24 C22 C23 111.5(6) . . ?
C15 C22 C23 107.7(9) . . ?
C24 C22 H23 108.5 . . ?
C15 C22 H23 108.5 . . ?
C23 C22 H23 108.5 . . ?
C21 C19 C17 112.6(6) . . ?
C21 C19 C20 110.3(8) . . ?
C17 C19 C20 110.7(10) . . ?
C21 C19 H24 107.7 . . ?
C17 C19 H24 107.7 . . ?
C20 C19 H24 107.7 . . ?
C14 C15 C16 118.5(7) . . ?
C14 C15 C22 119.9(6) . . ?
C16 C15 C22 121.5(7) . . ?
C10 C11 H26A 109.5 . . ?
C10 C11 H26B 109.5 . . ?
H26A C11 H26B 109.5 . . ?
C10 C11 H26C 109.5 . . ?
H26A C11 H26C 109.5 . . ?
H26B C11 H26C 109.5 . . ?
C11 C10 C2 112.1(7) . . ?
C11 C10 C12 112.2(11) . . ?
C2 C10 C12 108.9(7) . . ?
C11 C10 H27 107.8 . . ?
C2 C10 H27 107.8 . . ?
C12 C10 H27 107.8 . . ?
C9 C7 C6 112.8(7) . . ?
C9 C7 C8 109.5(7) . . ?
C6 C7 C8 110.9(9) . . ?
C9 C7 H28 107.8 . . ?
C6 C7 H28 107.8 . . ?
C8 C7 H28 107.8 . . ?
C33 C32 C31 120.6(9) . . ?
C33 C32 H29 119.7 . . ?
C31 C32 H29 119.7 . . ?
C30 C29 C28 119.6(9) . . ?
C30 C29 H30 120.2 . . ?
C28 C29 H30 120.2 . . ?
C34 C35 C36 121.0(12) . . ?
C34 C35 H31 119.5 . . ?
C36 C35 H31 119.5 . . ?
C22 C23 H32A 109.5 . . ?
C22 C23 H32B 109.5 . . ?
H32A C23 H32B 109.5 . . ?
C22 C23 H32C 109.5 . . ?
H32A C23 H32C 109.5 . . ?
H32B C23 H32C 109.5 . . ?
C22 C24 H33A 109.5 . . ?
C22 C24 H33B 109.5 . . ?
H33A C24 H33B 109.5 . . ?
C22 C24 H33C 109.5 . . ?
H33A C24 H33C 109.5 . . ?
H33B C24 H33C 109.5 . . ?
C7 C9 H34A 109.5 . . ?
C7 C9 H34B 109.5 . . ?
H34A C9 H34B 109.5 . . ?
C7 C9 H34C 109.5 . . ?
H34A C9 H34C 109.5 . . ?
H34B C9 H34C 109.5 . . ?
C19 C21 H35A 109.5 . . ?
C19 C21 H35B 109.5 . . ?
H35A C21 H35B 109.5 . . ?
C19 C21 H35C 109.5 . . ?
H35A C21 H35C 109.5 . . ?
H35B C21 H35C 109.5 . . ?
C7 C8 H36A 109.5 . . ?
C7 C8 H36B 109.5 . . ?
H36A C8 H36B 109.5 . . ?
C7 C8 H36C 109.5 . . ?
H36A C8 H36C 109.5 . . ?
H36B C8 H36C 109.5 . . ?
C36 C37 C38 121.6(9) . . ?
C36 C37 H37 119.2 . . ?
C38 C37 H37 119.2 . . ?
O3 C25 H38A 109.5 . . ?
O3 C25 H38B 109.5 . . ?
H38A C25 H38B 109.5 . . ?
O3 C25 H38C 109.5 . . ?
H38A C25 H38C 109.5 . . ?
H38B C25 H38C 109.5 . . ?
O4 C26 H39A 109.5 . . ?
O4 C26 H39B 109.5 . . ?
H39A C26 H39B 109.5 . . ?
O4 C26 H39C 109.5 . . ?
H39A C26 H39C 109.5 . . ?
H39B C26 H39C 109.5 . . ?
C37 C38 C39 117.7(12) . . ?
C37 C38 H40 121.1 . . ?
C39 C38 H40 121.1 . . ?
C30 C31 C32 118.8(10) . . ?
C30 C31 H41 120.6 . . ?
C32 C31 H41 120.6 . . ?
C31 C30 C29 121.3(8) . . ?
C31 C30 H42 119.3 . . ?
C29 C30 H42 119.3 . . ?
C19 C20 H43A 109.5 . . ?
C19 C20 H43B 109.5 . . ?
H43A C20 H43B 109.5 . . ?
C19 C20 H43C 109.5 . . ?
H43A C20 H43C 109.5 . . ?
H43B C20 H43C 109.5 . . ?
C37 C36 C35 119.9(11) . . ?
C37 C36 H44 120.1 . . ?
C35 C36 H44 120.1 . . ?
C10 C12 H45A 109.5 . . ?
C10 C12 H45B 109.5 . . ?
H45A C12 H45B 109.5 . . ?
C10 C12 H45C 109.5 . . ?
H45A C12 H45C 109.5 . . ?
H45B C12 H45C 109.5 . . ?

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
O2 P1 O1 C1 -44.7(9) . . . . ?
O3 P1 O1 C1 -172.7(8) . . . . ?
O4 P1 O1 C1 82.4(8) . . . . ?
O2 P1 O3 C25 -45.6(9) . . . . ?
O4 P1 O3 C25 -171.6(8) . . . . ?
O1 P1 O3 C25 81.5(9) . . . . ?
O2 P1 O4 C26 -37.7(7) . . . . ?
O3 P1 O4 C26 90.2(7) . . . . ?
O1 P1 O4 C26 -165.6(6) . . . . ?
C16 N1 C27 C34 171.6(6) . . . . ?
C16 N1 C27 C28 -4.2(11) . . . . ?
P1 O1 C1 C2 -92.5(10) . . . . ?
P1 O1 C1 C6 93.3(8) . . . . ?
C6 C1 C2 C3 -2.7(12) . . . . ?
O1 C1 C2 C3 -176.5(6) . . . . ?
C6 C1 C2 C10 174.1(7) . . . . ?
O1 C1 C2 C10 0.3(12) . . . . ?
C1 C2 C3 C4 2.6(12) . . . . ?
C10 C2 C3 C4 -174.4(7) . . . . ?
N1 C27 C28 C29 -41.6(12) . . . . ?
C34 C27 C28 C29 142.6(8) . . . . ?
N1 C27 C28 C33 132.8(9) . . . . ?
C34 C27 C28 C33 -43.0(11) . . . . ?
C2 C3 C4 C5 -0.7(12) . . . . ?
C2 C3 C4 C13 179.7(7) . . . . ?
C6 C5 C4 C3 -1.4(11) . . . . ?
C6 C5 C4 C13 178.1(7) . . . . ?
C4 C5 C6 C1 1.4(11) . . . . ?
C4 C5 C6 C7 178.8(7) . . . . ?
C2 C1 C6 C5 0.7(12) . . . . ?
O1 C1 C6 C5 174.5(6) . . . . ?
C2 C1 C6 C7 -176.7(8) . . . . ?
O1 C1 C6 C7 -2.9(11) . . . . ?
C18 C17 C16 C15 0.9(15) . . . . ?
C19 C17 C16 C15 179.5(10) . . . . ?
C18 C17 C16 N1 175.8(10) . . . . ?
C19 C17 C16 N1 -5.7(14) . . . . ?
C27 N1 C16 C15 -66.5(13) . . . . ?
C27 N1 C16 C17 118.6(10) . . . . ?
C3 C4 C13 C14 53.4(13) . . . . ?
C5 C4 C13 C14 -126.1(10) . . . . ?
C3 C4 C13 C18 -128.1(10) . . . . ?
C5 C4 C13 C18 52.4(13) . . . . ?
C38 C39 C34 C35 1.1(12) . . . . ?
C38 C39 C34 C27 179.3(7) . . . . ?
N1 C27 C34 C35 -32.0(10) . . . . ?
C28 C27 C34 C35 144.2(8) . . . . ?
N1 C27 C34 C39 149.8(8) . . . . ?
C28 C27 C34 C39 -34.0(10) . . . . ?
C18 C13 C14 C15 1.3(16) . . . . ?
C4 C13 C14 C15 179.9(10) . . . . ?
C16 C17 C18 C13 0.0(16) . . . . ?
C19 C17 C18 C13 -178.5(10) . . . . ?
C14 C13 C18 C17 -1.1(16) . . . . ?
C4 C13 C18 C17 -179.7(10) . . . . ?
C29 C28 C33 C32 2.1(14) . . . . ?
C27 C28 C33 C32 -172.4(9) . . . . ?
C18 C17 C19 C21 48.6(15) . . . . ?
C16 C17 C19 C21 -129.9(11) . . . . ?
C18 C17 C19 C20 -75.4(12) . . . . ?
C16 C17 C19 C20 106.1(12) . . . . ?
C13 C14 C15 C16 -0.4(16) . . . . ?
C13 C14 C15 C22 -176.7(10) . . . . ?
C17 C16 C15 C14 -0.7(16) . . . . ?
N1 C16 C15 C14 -175.4(10) . . . . ?
C17 C16 C15 C22 175.5(10) . . . . ?
N1 C16 C15 C22 0.9(16) . . . . ?
C24 C22 C15 C14 -51.8(14) . . . . ?
C23 C22 C15 C14 71.2(11) . . . . ?
C24 C22 C15 C16 131.9(10) . . . . ?
C23 C22 C15 C16 -105.0(11) . . . . ?
C1 C2 C10 C11 -118.9(11) . . . . ?
C3 C2 C10 C11 57.9(11) . . . . ?
C1 C2 C10 C12 116.5(10) . . . . ?
C3 C2 C10 C12 -66.8(11) . . . . ?
C5 C6 C7 C9 21.4(11) . . . . ?
C1 C6 C7 C9 -161.3(7) . . . . ?
C5 C6 C7 C8 -101.7(9) . . . . ?
C1 C6 C7 C8 75.6(9) . . . . ?
C28 C33 C32 C31 -3.4(16) . . . . ?
C33 C28 C29 C30 -0.2(14) . . . . ?
C27 C28 C29 C30 174.2(9) . . . . ?
C39 C34 C35 C36 0.6(12) . . . . ?
C27 C34 C35 C36 -177.6(8) . . . . ?
C36 C37 C38 C39 1.3(14) . . . . ?
C34 C39 C38 C37 -2.1(12) . . . . ?
C33 C32 C31 C30 2.7(17) . . . . ?
C32 C31 C30 C29 -0.8(17) . . . . ?
C28 C29 C30 C31 -0.4(16) . . . . ?
C38 C37 C36 C35 0.4(16) . . . . ?
C34 C35 C36 C37 -1.4(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.599
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.599
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_Compound6
_database_code_depnum_ccdc_archive 'CCDC 1009229'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H27 O5 P'
_chemical_formula_sum            'C21 H27 O5 P'
_chemical_formula_weight         390.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.690(2)
_cell_length_b                   9.064(3)
_cell_length_c                   17.502(5)
_cell_angle_alpha                79.175(12)
_cell_angle_beta                 89.610(12)
_cell_angle_gamma                82.167(12)
_cell_volume                     1032.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9685
_exptl_absorpt_correction_T_max  0.9685
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7604
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3773
_reflns_number_gt                3570
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0431P)²+0.6248P] 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_number_reflns         3773
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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 0.65730(6) 0.65148(5) 0.89864(2) 0.02107(13) Uani 1 1 d . . .
O2 O 0.8116(2) 0.51946(14) 0.90907(7) 0.0326(3) Uani 1 1 d . . .
O4 O 0.44061(18) 0.60691(14) 0.90960(7) 0.0304(3) Uani 1 1 d . . .
O3 O 0.68306(19) 0.76909(14) 0.95224(7) 0.0290(3) Uani 1 1 d . . .
O1 O 0.63556(16) 0.75762(12) 0.81486(6) 0.0200(2) Uani 1 1 d . . .
O5 O 1.7134(2) 1.35508(16) 0.47334(9) 0.0467(4) Uani 1 1 d . . .
C10 C 0.8174(2) 0.97227(18) 0.77853(9) 0.0194(3) Uani 1 1 d . . .
C11 C 0.7972(2) 0.82180(17) 0.77522(9) 0.0180(3) Uani 1 1 d . . .
C13 C 1.0680(2) 0.80697(17) 0.68634(9) 0.0200(3) Uani 1 1 d . . .
H13 H 1.1542 0.7511 0.6553 0.024 Uiso 1 1 calc R . .
C8 C 1.0954(2) 0.95645(18) 0.68772(9) 0.0200(3) Uani 1 1 d . . .
C12 C 0.9185(2) 0.73678(17) 0.72897(9) 0.0191(3) Uani 1 1 d . . .
C2 C 1.5615(3) 1.16131(19) 0.55548(9) 0.0237(4) Uani 1 1 d . . .
C5 C 1.2560(2) 1.02805(17) 0.64125(9) 0.0197(3) Uani 1 1 d . . .
C4 C 1.2251(3) 1.18243(18) 0.60542(9) 0.0229(3) Uani 1 1 d . . .
H4 H 1.0989 1.2418 0.6102 0.027 Uiso 1 1 calc R . .
C14 C 0.8943(3) 0.57430(18) 0.72281(9) 0.0228(4) Uani 1 1 d . . .
H14 H 0.7849 0.5415 0.7586 0.027 Uiso 1 1 calc R . .
C7 C 1.5931(3) 1.00896(19) 0.59079(9) 0.0239(4) Uani 1 1 d . . .
H7 H 1.7192 0.9496 0.5856 0.029 Uiso 1 1 calc R . .
C17 C 0.6803(3) 1.06865(18) 0.82685(9) 0.0231(4) Uani 1 1 d . . .
H17 H 0.5765 1.0068 0.8521 0.028 Uiso 1 1 calc R . .
C3 C 1.3761(3) 1.24848(19) 0.56334(9) 0.0240(4) Uani 1 1 d . . .
H3 H 1.3539 1.3528 0.5398 0.029 Uiso 1 1 calc R . .
C9 C 0.9681(2) 1.03633(18) 0.73406(9) 0.0207(3) Uani 1 1 d . . .
H9 H 0.9849 1.1383 0.7353 0.025 Uiso 1 1 calc R . .
C18 C 0.5722(3) 1.2102(2) 0.77574(11) 0.0316(4) Uani 1 1 d . . .
H18A H 0.4856 1.2692 0.8078 0.047 Uiso 1 1 calc R . .
H18B H 0.4893 1.1815 0.7365 0.047 Uiso 1 1 calc R . .
H18C H 0.6717 1.2716 0.7499 0.047 Uiso 1 1 calc R . .
C6 C 1.4420(2) 0.94288(19) 0.63344(9) 0.0220(3) Uani 1 1 d . . .
H6 H 1.4656 0.8388 0.6575 0.026 Uiso 1 1 calc R . .
C16 C 0.8327(3) 0.5638(2) 0.63987(11) 0.0305(4) Uani 1 1 d . . .
H16A H 0.8182 0.4585 0.6378 0.046 Uiso 1 1 calc R . .
H16B H 0.9367 0.5977 0.6036 0.046 Uiso 1 1 calc R . .
H16C H 0.7039 0.6285 0.6253 0.046 Uiso 1 1 calc R . .
C1 C 1.7237(3) 1.2267(2) 0.50883(10) 0.0308(4) Uani 1 1 d . . .
H1 H 1.8469 1.1619 0.5066 0.037 Uiso 1 1 calc R . .
C15 C 1.0904(3) 0.46912(19) 0.74947(12) 0.0339(4) Uani 1 1 d . . .
H15A H 1.0742 0.3649 0.7456 0.051 Uiso 1 1 calc R . .
H15B H 1.1214 0.4734 0.8036 0.051 Uiso 1 1 calc R . .
H15C H 1.2009 0.5018 0.7163 0.051 Uiso 1 1 calc R . .
C21 C 0.7499(3) 0.7171(2) 1.03302(10) 0.0335(4) Uani 1 1 d . . .
H21A H 0.7574 0.8048 1.0576 0.050 Uiso 1 1 calc R . .
H21B H 0.8834 0.6565 1.0350 0.050 Uiso 1 1 calc R . .
H21C H 0.6537 0.6548 1.0608 0.050 Uiso 1 1 calc R . .
C20 C 0.2629(3) 0.7195(3) 0.90452(12) 0.0394(5) Uani 1 1 d . . .
H20A H 0.1423 0.6686 0.9132 0.059 Uiso 1 1 calc R . .
H20B H 0.2537 0.7844 0.8528 0.059 Uiso 1 1 calc R . .
H20C H 0.2724 0.7818 0.9441 0.059 Uiso 1 1 calc R . .
C19 C 0.8063(3) 1.1101(2) 0.89150(11) 0.0353(4) Uani 1 1 d . . .
H19A H 0.8744 1.0171 0.9240 0.053 Uiso 1 1 calc R . .
H19B H 0.7171 1.1670 0.9237 0.053 Uiso 1 1 calc R . .
H19C H 0.9072 1.1725 0.8678 0.053 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 O2 1.4543(14) . ?
P1 O4 1.5583(13) . ?
P1 O3 1.5729(13) . ?
P1 O1 1.5912(12) . ?
O4 C20 1.449(2) . ?
O3 C21 1.457(2) . ?
O1 C11 1.4138(19) . ?
O5 C1 1.205(2) . ?
C10 C9 1.392(2) . ?
C10 C11 1.401(2) . ?
C10 C17 1.539(2) . ?
C11 C12 1.401(2) . ?
C13 C12 1.395(2) . ?
C13 C8 1.396(2) . ?
C13 H13 0.9500 . ?
C8 C9 1.397(2) . ?
C8 C5 1.489(2) . ?
C12 C14 1.527(2) . ?
C2 C7 1.391(2) . ?
C2 C3 1.398(2) . ?
C2 C1 1.475(2) . ?
C5 C6 1.392(2) . ?
C5 C4 1.410(2) . ?
C4 C3 1.382(2) . ?
C4 H4 0.9500 . ?
C14 C15 1.532(2) . ?
C14 C16 1.535(2) . ?
C14 H14 1.0000 . ?
C7 C6 1.387(2) . ?
C7 H7 0.9500 . ?
C17 C18 1.515(2) . ?
C17 C19 1.547(2) . ?
C17 H17 1.0000 . ?
C3 H3 0.9500 . ?
C9 H9 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C6 H6 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C1 H1 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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 P1 O4 112.20(8) . . ?
O2 P1 O3 115.15(8) . . ?
O4 P1 O3 108.12(7) . . ?
O2 P1 O1 117.20(7) . . ?
O4 P1 O1 101.18(6) . . ?
O3 P1 O1 101.53(7) . . ?
C20 O4 P1 122.13(12) . . ?
C21 O3 P1 120.38(11) . . ?
C11 O1 P1 123.89(10) . . ?
C9 C10 C11 117.09(14) . . ?
C9 C10 C17 119.45(14) . . ?
C11 C10 C17 123.45(14) . . ?
C10 C11 C12 122.96(14) . . ?
C10 C11 O1 118.33(13) . . ?
C12 C11 O1 118.46(13) . . ?
C12 C13 C8 122.25(14) . . ?
C12 C13 H13 118.9 . . ?
C8 C13 H13 118.9 . . ?
C13 C8 C9 118.01(15) . . ?
C13 C8 C5 120.85(14) . . ?
C9 C8 C5 121.14(14) . . ?
C13 C12 C11 117.16(14) . . ?
C13 C12 C14 119.21(14) . . ?
C11 C12 C14 123.63(14) . . ?
C7 C2 C3 119.60(15) . . ?
C7 C2 C1 119.07(16) . . ?
C3 C2 C1 121.31(16) . . ?
C6 C5 C4 118.70(15) . . ?
C6 C5 C8 120.03(14) . . ?
C4 C5 C8 121.26(15) . . ?
C3 C4 C5 120.85(16) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C12 C14 C15 109.67(14) . . ?
C12 C14 C16 111.36(13) . . ?
C15 C14 C16 111.26(14) . . ?
C12 C14 H14 108.1 . . ?
C15 C14 H14 108.1 . . ?
C16 C14 H14 108.1 . . ?
C6 C7 C2 120.59(16) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C18 C17 C10 111.12(13) . . ?
C18 C17 C19 110.75(15) . . ?
C10 C17 C19 109.84(15) . . ?
C18 C17 H17 108.3 . . ?
C10 C17 H17 108.3 . . ?
C19 C17 H17 108.3 . . ?
C4 C3 C2 119.82(15) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C10 C9 C8 122.50(15) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C6 C5 120.43(15) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C1 C2 125.68(18) . . ?
O5 C1 H1 117.2 . . ?
C2 C1 H1 117.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
O2 P1 O4 C20 177.94(13) . . . . ?
O3 P1 O4 C20 49.87(15) . . . . ?
O1 P1 O4 C20 -56.34(14) . . . . ?
O2 P1 O3 C21 -39.50(16) . . . . ?
O4 P1 O3 C21 86.86(14) . . . . ?
O1 P1 O3 C21 -167.18(13) . . . . ?
O2 P1 O1 C11 -53.85(14) . . . . ?
O4 P1 O1 C11 -176.16(11) . . . . ?
O3 P1 O1 C11 72.49(12) . . . . ?
C9 C10 C11 C12 -0.9(2) . . . . ?
C17 C10 C11 C12 177.77(14) . . . . ?
C9 C10 C11 O1 -175.09(13) . . . . ?
C17 C10 C11 O1 3.6(2) . . . . ?
P1 O1 C11 C10 -98.54(15) . . . . ?
P1 O1 C11 C12 87.03(16) . . . . ?
C12 C13 C8 C9 0.4(2) . . . . ?
C12 C13 C8 C5 -179.75(14) . . . . ?
C8 C13 C12 C11 -1.2(2) . . . . ?
C8 C13 C12 C14 178.40(14) . . . . ?
C10 C11 C12 C13 1.5(2) . . . . ?
O1 C11 C12 C13 175.70(13) . . . . ?
C10 C11 C12 C14 -178.09(14) . . . . ?
O1 C11 C12 C14 -3.9(2) . . . . ?
C13 C8 C5 C6 -37.4(2) . . . . ?
C9 C8 C5 C6 142.46(16) . . . . ?
C13 C8 C5 C4 143.54(16) . . . . ?
C9 C8 C5 C4 -36.6(2) . . . . ?
C6 C5 C4 C3 0.0(2) . . . . ?
C8 C5 C4 C3 179.03(15) . . . . ?
C13 C12 C14 C15 60.01(19) . . . . ?
C11 C12 C14 C15 -120.37(17) . . . . ?
C13 C12 C14 C16 -63.6(2) . . . . ?
C11 C12 C14 C16 116.03(17) . . . . ?
C3 C2 C7 C6 0.2(2) . . . . ?
C1 C2 C7 C6 -178.37(15) . . . . ?
C9 C10 C17 C18 57.6(2) . . . . ?
C11 C10 C17 C18 -121.07(17) . . . . ?
C9 C10 C17 C19 -65.31(19) . . . . ?
C11 C10 C17 C19 116.03(18) . . . . ?
C5 C4 C3 C2 0.5(2) . . . . ?
C7 C2 C3 C4 -0.6(2) . . . . ?
C1 C2 C3 C4 177.91(15) . . . . ?
C11 C10 C9 C8 0.0(2) . . . . ?
C17 C10 C9 C8 -178.76(15) . . . . ?
C13 C8 C9 C10 0.3(2) . . . . ?
C5 C8 C9 C10 -179.59(14) . . . . ?
C2 C7 C6 C5 0.3(2) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C8 C5 C6 C7 -179.47(14) . . . . ?
C7 C2 C1 O5 177.47(18) . . . . ?
C3 C2 C1 O5 -1.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_Compound8
_database_code_depnum_ccdc_archive 'CCDC 1023021'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H23 O5 P'
_chemical_formula_sum            'C19 H23 O5 P'
_chemical_formula_weight         362.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   41.181(13)
_cell_length_b                   11.010(3)
_cell_length_c                   8.186(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.162(6)
_cell_angle_gamma                90.00
_cell_volume                     3709(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3543
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      31.4

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9661
_exptl_absorpt_correction_T_max  0.9661
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13678
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3259
_reflns_number_gt                3152
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0456P)²+6.1935P] 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_number_reflns         3259
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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 0.045866(12) 0.38055(5) 0.36794(6) 0.02259(16) Uani 1 1 d . . .
O4 O 0.06666(3) 0.47304(13) 0.46533(18) 0.0289(4) Uani 1 1 d . . .
H4 H 0.0570 0.5401 0.4666 0.043 Uiso 1 1 calc R . .
O1 O 0.06585(3) 0.25949(12) 0.37053(16) 0.0244(3) Uani 1 1 d . . .
O2 O 0.03856(3) 0.41573(14) 0.19454(17) 0.0282(3) Uani 1 1 d . . .
O3 O 0.01464(3) 0.35337(15) 0.45981(17) 0.0308(4) Uani 1 1 d . . .
H3 H -0.0016 0.3760 0.4027 0.046 Uiso 1 1 calc R . .
O5 O 0.28002(4) -0.03127(17) 1.0346(2) 0.0460(5) Uani 1 1 d . . .
C2 C 0.12407(5) 0.27080(18) 0.3949(2) 0.0237(4) Uani 1 1 d . . .
C6 C 0.09275(5) 0.17483(18) 0.6097(2) 0.0240(4) Uani 1 1 d . . .
C5 C 0.12199(5) 0.14815(19) 0.6934(2) 0.0262(5) Uani 1 1 d . . .
H5 H 0.1215 0.1051 0.7938 0.031 Uiso 1 1 calc R . .
C4 C 0.15194(5) 0.18240(19) 0.6348(2) 0.0257(5) Uani 1 1 d . . .
C10 C 0.12585(5) 0.3325(2) 0.2288(2) 0.0274(5) Uani 1 1 d . . .
H10 H 0.1031 0.3411 0.1828 0.033 Uiso 1 1 calc R . .
C3 C 0.15242(5) 0.24382(19) 0.4857(2) 0.0257(5) Uani 1 1 d . . .
H3A H 0.1727 0.2680 0.4449 0.031 Uiso 1 1 calc R . .
C7 C 0.06015(5) 0.1408(2) 0.6801(3) 0.0289(5) Uani 1 1 d . . .
H7 H 0.0431 0.1502 0.5908 0.035 Uiso 1 1 calc R . .
C1 C 0.09496(5) 0.23671(18) 0.4624(2) 0.0228(4) Uani 1 1 d . . .
C13 C 0.18288(5) 0.15302(19) 0.7249(2) 0.0263(5) Uani 1 1 d . . .
C15 C 0.23900(6) 0.1995(2) 0.7928(3) 0.0353(5) Uani 1 1 d . . .
H15 H 0.2571 0.2526 0.7851 0.042 Uiso 1 1 calc R . .
C17 C 0.21577(5) 0.0156(2) 0.8924(3) 0.0313(5) Uani 1 1 d . . .
H17 H 0.2177 -0.0576 0.9534 0.038 Uiso 1 1 calc R . .
C8 C 0.05930(6) 0.0095(2) 0.7382(3) 0.0388(6) Uani 1 1 d . . .
H8A H 0.0380 -0.0082 0.7816 0.058 Uiso 1 1 calc R . .
H8B H 0.0762 -0.0030 0.8242 0.058 Uiso 1 1 calc R . .
H8C H 0.0632 -0.0449 0.6462 0.058 Uiso 1 1 calc R . .
C19 C 0.27417(6) 0.0610(2) 0.9589(3) 0.0378(6) Uani 1 1 d . . .
H19 H 0.2914 0.1177 0.9491 0.045 Uiso 1 1 calc R . .
C16 C 0.24249(5) 0.0921(2) 0.8809(3) 0.0312(5) Uani 1 1 d . . .
C12 C 0.14442(6) 0.2518(2) 0.1123(3) 0.0377(6) Uani 1 1 d . . .
H12A H 0.1453 0.2916 0.0055 0.057 Uiso 1 1 calc R . .
H12B H 0.1333 0.1735 0.0996 0.057 Uiso 1 1 calc R . .
H12C H 0.1665 0.2384 0.1570 0.057 Uiso 1 1 calc R . .
C18 C 0.18642(5) 0.0455(2) 0.8156(3) 0.0304(5) Uani 1 1 d . . .
H18 H 0.1684 -0.0076 0.8242 0.037 Uiso 1 1 calc R . .
C14 C 0.20970(6) 0.2300(2) 0.7162(3) 0.0333(5) Uani 1 1 d . . .
H14 H 0.2078 0.3041 0.6571 0.040 Uiso 1 1 calc R . .
C11 C 0.14049(6) 0.4598(2) 0.2428(3) 0.0383(6) Uani 1 1 d . . .
H11A H 0.1411 0.4965 0.1339 0.058 Uiso 1 1 calc R . .
H11B H 0.1626 0.4544 0.2906 0.058 Uiso 1 1 calc R . .
H11C H 0.1272 0.5100 0.3129 0.058 Uiso 1 1 calc R . .
C9 C 0.05199(6) 0.2285(2) 0.8167(3) 0.0423(6) Uani 1 1 d . . .
H9A H 0.0310 0.2063 0.8607 0.064 Uiso 1 1 calc R . .
H9B H 0.0508 0.3114 0.7733 0.064 Uiso 1 1 calc R . .
H9C H 0.0689 0.2242 0.9039 0.064 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 O2 1.4910(15) . ?
P1 O4 1.5344(15) . ?
P1 O3 1.5434(15) . ?
P1 O1 1.5662(15) . ?
O4 H4 0.8400 . ?
O1 C1 1.414(2) . ?
O3 H3 0.8400 . ?
O5 C19 1.209(3) . ?
C2 C1 1.390(3) . ?
C2 C3 1.392(3) . ?
C2 C10 1.524(3) . ?
C6 C1 1.391(3) . ?
C6 C5 1.393(3) . ?
C6 C7 1.527(3) . ?
C5 C4 1.392(3) . ?
C5 H5 0.9500 . ?
C4 C3 1.396(3) . ?
C4 C13 1.484(3) . ?
C10 C11 1.528(3) . ?
C10 C12 1.530(3) . ?
C10 H10 1.0000 . ?
C3 H3A 0.9500 . ?
C7 C8 1.523(3) . ?
C7 C9 1.525(3) . ?
C7 H7 1.0000 . ?
C13 C14 1.396(3) . ?
C13 C18 1.402(3) . ?
C15 C14 1.380(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C17 C18 1.381(3) . ?
C17 C16 1.392(3) . ?
C17 H17 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C19 C16 1.471(3) . ?
C19 H19 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C18 H18 0.9500 . ?
C14 H14 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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 P1 O4 114.26(9) . . ?
O2 P1 O3 111.86(8) . . ?
O4 P1 O3 109.54(9) . . ?
O2 P1 O1 108.72(8) . . ?
O4 P1 O1 105.97(8) . . ?
O3 P1 O1 105.99(8) . . ?
P1 O4 H4 109.5 . . ?
C1 O1 P1 126.37(12) . . ?
P1 O3 H3 109.5 . . ?
C1 C2 C3 116.66(18) . . ?
C1 C2 C10 123.09(18) . . ?
C3 C2 C10 120.24(18) . . ?
C1 C6 C5 116.45(18) . . ?
C1 C6 C7 122.28(18) . . ?
C5 C6 C7 121.24(18) . . ?
C4 C5 C6 122.29(19) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C4 C3 118.30(19) . . ?
C5 C4 C13 121.68(19) . . ?
C3 C4 C13 120.01(19) . . ?
C2 C10 C11 111.96(18) . . ?
C2 C10 C12 109.83(18) . . ?
C11 C10 C12 112.00(19) . . ?
C2 C10 H10 107.6 . . ?
C11 C10 H10 107.6 . . ?
C12 C10 H10 107.6 . . ?
C2 C3 C4 122.05(19) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C8 C7 C9 111.33(19) . . ?
C8 C7 C6 112.42(18) . . ?
C9 C7 C6 110.03(18) . . ?
C8 C7 H7 107.6 . . ?
C9 C7 H7 107.6 . . ?
C6 C7 H7 107.6 . . ?
C6 C1 C2 124.21(19) . . ?
C6 C1 O1 117.80(17) . . ?
C2 C1 O1 117.87(17) . . ?
C14 C13 C18 118.2(2) . . ?
C14 C13 C4 120.54(19) . . ?
C18 C13 C4 121.16(19) . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O5 C19 C16 125.1(2) . . ?
O5 C19 H19 117.5 . . ?
C16 C19 H19 117.5 . . ?
C15 C16 C17 118.9(2) . . ?
C15 C16 C19 119.8(2) . . ?
C17 C16 C19 121.3(2) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C17 C18 C13 120.9(2) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
O2 P1 O1 C1 130.86(15) . . . . ?
O4 P1 O1 C1 7.62(17) . . . . ?
O3 P1 O1 C1 -108.74(16) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C7 C6 C5 C4 -177.45(19) . . . . ?
C6 C5 C4 C3 -1.1(3) . . . . ?
C6 C5 C4 C13 -179.81(19) . . . . ?
C1 C2 C10 C11 117.4(2) . . . . ?
C3 C2 C10 C11 -63.8(3) . . . . ?
C1 C2 C10 C12 -117.5(2) . . . . ?
C3 C2 C10 C12 61.3(3) . . . . ?
C1 C2 C3 C4 1.9(3) . . . . ?
C10 C2 C3 C4 -177.00(19) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?
C13 C4 C3 C2 178.45(19) . . . . ?
C1 C6 C7 C8 133.2(2) . . . . ?
C5 C6 C7 C8 -48.7(3) . . . . ?
C1 C6 C7 C9 -102.1(2) . . . . ?
C5 C6 C7 C9 76.0(2) . . . . ?
C5 C6 C1 C2 1.0(3) . . . . ?
C7 C6 C1 C2 179.14(19) . . . . ?
C5 C6 C1 O1 176.76(17) . . . . ?
C7 C6 C1 O1 -5.1(3) . . . . ?
C3 C2 C1 C6 -2.2(3) . . . . ?
C10 C2 C1 C6 176.60(19) . . . . ?
C3 C2 C1 O1 -178.03(17) . . . . ?
C10 C2 C1 O1 0.8(3) . . . . ?
P1 O1 C1 C6 98.1(2) . . . . ?
P1 O1 C1 C2 -85.8(2) . . . . ?
C5 C4 C13 C14 -149.0(2) . . . . ?
C3 C4 C13 C14 32.3(3) . . . . ?
C5 C4 C13 C18 33.5(3) . . . . ?
C3 C4 C13 C18 -145.2(2) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C14 C15 C16 C19 179.0(2) . . . . ?
C18 C17 C16 C15 0.8(3) . . . . ?
C18 C17 C16 C19 -178.7(2) . . . . ?
O5 C19 C16 C15 -178.0(2) . . . . ?
O5 C19 C16 C17 1.5(4) . . . . ?
C16 C17 C18 C13 -0.1(3) . . . . ?
C14 C13 C18 C17 -0.9(3) . . . . ?
C4 C13 C18 C17 176.7(2) . . . . ?
C16 C15 C14 C13 -0.4(4) . . . . ?
C18 C13 C14 C15 1.1(3) . . . . ?
C4 C13 C14 C15 -176.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.045

