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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c
_database_code_depnum_ccdc_archive 'CCDC 1446727'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 O P'
_chemical_formula_weight         290.28

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.1947(6)
_cell_length_b                   8.7300(5)
_cell_length_c                   34.4274(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3064.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1826
_cell_measurement_theta_min      3.0659
_cell_measurement_theta_max      29.1658

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_reflns_number            7468
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.292
_diffrn_reflns_theta_max         29.230
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3475
_reflns_number_gt                2452
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+1.3017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3475
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C19 C 0.6432(3) -0.1884(3) 0.50054(8) 0.0731(8) Uani 1 1 d . . . . .
H19A H 0.5676 -0.2400 0.5081 0.088 Uiso 1 1 calc R U . . .
C1 C 0.4428(3) 0.5967(3) 0.35420(8) 0.0680(7) Uani 1 1 d . . . . .
H1A H 0.4421 0.6835 0.3385 0.082 Uiso 1 1 calc R U . . .
C2 C 0.5170(3) 0.4710(3) 0.34345(7) 0.0583(6) Uani 1 1 d . . . . .
H2A H 0.5669 0.4748 0.3209 0.070 Uiso 1 1 calc R U . . .
C3 C 0.5177(2) 0.3391(2) 0.36607(6) 0.0445(5) Uani 1 1 d . . . . .
C4 C 0.4438(2) 0.3405(3) 0.39989(7) 0.0561(6) Uani 1 1 d . . . . .
H4A H 0.4434 0.2545 0.4158 0.067 Uiso 1 1 calc R U . . .
C5 C 0.3707(3) 0.4670(3) 0.41030(8) 0.0622(7) Uani 1 1 d . . . . .
H5A H 0.3213 0.4649 0.4330 0.075 Uiso 1 1 calc R U . . .
C6 C 0.3704(3) 0.5948(3) 0.38769(8) 0.0637(7) Uani 1 1 d . . . . .
H6A H 0.3214 0.6800 0.3949 0.076 Uiso 1 1 calc R U . . .
C7 C 0.3184(3) 0.0032(3) 0.28615(7) 0.0663(7) Uani 1 1 d . . . . .
H7A H 0.2294 0.0209 0.2823 0.080 Uiso 1 1 calc R U . . .
C8 C 0.3789(3) -0.1126(3) 0.26639(7) 0.0597(7) Uani 1 1 d . . . . .
H8A H 0.3317 -0.1732 0.2491 0.072 Uiso 1 1 calc R U . . .
C9 C 0.5093(3) -0.1385(3) 0.27226(7) 0.0681(8) Uani 1 1 d . . . . .
H9A H 0.5514 -0.2171 0.2590 0.082 Uiso 1 1 calc R U . . .
C10 C 0.5788(3) -0.0480(3) 0.29789(7) 0.0623(7) Uani 1 1 d . . . . .
H10A H 0.6677 -0.0665 0.3016 0.075 Uiso 1 1 calc R U . . .
C11 C 0.5190(2) 0.0695(3) 0.31822(5) 0.0422(5) Uani 1 1 d . . . . .
C12 C 0.3872(2) 0.0941(3) 0.31175(7) 0.0572(6) Uani 1 1 d . . . . .
H12A H 0.3443 0.1729 0.3248 0.069 Uiso 1 1 calc R U . . .
C13 C 0.7448(3) -0.0173(3) 0.45135(7) 0.0586(7) Uani 1 1 d . . . . .
H13A H 0.8210 -0.0148 0.4662 0.070 Uiso 1 1 calc R U . . .
C14 C 0.7387(2) 0.0641(3) 0.41680(6) 0.0530(6) Uani 1 1 d . . . . .
H14A H 0.8107 0.1212 0.4087 0.064 Uiso 1 1 calc R U . . .
C15 C 0.6263(2) 0.0612(2) 0.39411(6) 0.0426(5) Uani 1 1 d . . . . .
C16 C 0.5214(2) -0.0283(3) 0.40639(7) 0.0504(6) Uani 1 1 d . . . . .
H16A H 0.4466 -0.0351 0.3910 0.060 Uiso 1 1 calc R U . . .
C17 C 0.5269(2) -0.1077(3) 0.44122(7) 0.0546(6) Uani 1 1 d . . . . .
H17A H 0.4551 -0.1650 0.4494 0.066 Uiso 1 1 calc R U . . .
C18 C 0.6388(3) -0.1017(3) 0.46381(7) 0.0528(6) Uani 1 1 d . . . . .
O1 O 0.7372(3) -0.1974(3) 0.52150(5) 0.0973(7) Uani 1 1 d . . . . .
P1 P 0.62431(5) 0.18189(7) 0.35051(2) 0.04640(18) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C19 O1 1.202(3) . ?
C19 C18 1.474(3) . ?
C1 C6 1.369(4) . ?
C1 C2 1.383(4) . ?
C2 C3 1.390(3) . ?
C3 C4 1.387(3) . ?
C3 P1 1.831(2) . ?
C4 C5 1.379(3) . ?
C5 C6 1.361(4) . ?
C7 C8 1.366(3) . ?
C7 C12 1.378(3) . ?
C8 C9 1.363(4) . ?
C9 C10 1.380(3) . ?
C10 C11 1.383(3) . ?
C11 C12 1.379(3) . ?
C11 P1 1.830(2) . ?
C13 C18 1.377(4) . ?
C13 C14 1.387(3) . ?
C14 C15 1.387(3) . ?
C15 C16 1.390(3) . ?
C15 P1 1.834(2) . ?
C16 C17 1.386(3) . ?
C17 C18 1.382(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C19 C18 124.9(3) . . ?
C6 C1 C2 120.7(3) . . ?
C1 C2 C3 120.7(2) . . ?
C4 C3 C2 117.4(2) . . ?
C4 C3 P1 125.09(18) . . ?
C2 C3 P1 117.40(18) . . ?
C5 C4 C3 121.2(2) . . ?
C6 C5 C4 120.6(3) . . ?
C5 C6 C1 119.4(3) . . ?
C8 C7 C12 121.0(2) . . ?
C9 C8 C7 119.3(2) . . ?
C8 C9 C10 120.1(2) . . ?
C9 C10 C11 121.5(2) . . ?
C12 C11 C10 117.6(2) . . ?
C12 C11 P1 125.87(18) . . ?
C10 C11 P1 116.53(18) . . ?
C7 C12 C11 120.6(2) . . ?
C18 C13 C14 120.4(2) . . ?
C13 C14 C15 120.7(2) . . ?
C14 C15 C16 118.3(2) . . ?
C14 C15 P1 117.34(17) . . ?
C16 C15 P1 124.32(16) . . ?
C17 C16 C15 120.9(2) . . ?
C18 C17 C16 120.1(2) . . ?
C13 C18 C17 119.5(2) . . ?
C13 C18 C19 121.2(2) . . ?
C17 C18 C19 119.2(2) . . ?
C11 P1 C3 103.37(10) . . ?
C11 P1 C15 101.26(9) . . ?
C3 P1 C15 101.40(10) . . ?

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.042

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c
_database_code_depnum_ccdc_archive 'CCDC 1446729'
_audit_update_record             
;
2016-01-12 deposited with the CCDC.
2016-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 O P'
_chemical_formula_weight         304.30

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5525(14)
_cell_length_b                   10.3525(17)
_cell_length_c                   10.5874(17)
_cell_angle_alpha                114.517(16)
_cell_angle_beta                 99.585(14)
_cell_angle_gamma                90.156(13)
_cell_volume                     838.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1757
_cell_measurement_theta_min      3.1869
_cell_measurement_theta_max      29.3081

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 16.1954
_diffrn_reflns_number            7088
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.193
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3389
_reflns_number_gt                2521
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlis PRO (Agilent, 2011)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2011)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²+0.1700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3389
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1460
_refine_ls_wR_factor_gt          0.1302
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.08480(7) 0.25203(6) 0.16440(6) 0.0438(2) Uani 1 1 d . . . . .
O1 O 0.3623(2) 0.0257(2) 0.6676(2) 0.0824(6) Uani 1 1 d . . . . .
C1 C 0.1500(4) 0.1357(3) 0.7785(3) 0.0801(9) Uani 1 1 d . . . . .
H1A H 0.0634 0.1868 0.7576 0.120 Uiso 1 1 calc R U . . .
H1B H 0.1087 0.0525 0.7845 0.120 Uiso 1 1 calc R U . . .
H1C H 0.2161 0.1959 0.8669 0.120 Uiso 1 1 calc R U . . .
C2 C 0.2469(3) 0.0916(3) 0.6631(3) 0.0559(6) Uani 1 1 d . . . . .
C4 C 0.1994(3) 0.1328(2) 0.5433(2) 0.0438(5) Uani 1 1 d . . . . .
C5 C 0.2985(3) 0.1056(2) 0.4445(2) 0.0477(5) Uani 1 1 d . . . . .
H5A H 0.3919 0.0620 0.4541 0.057 Uiso 1 1 calc R U . . .
C6 C 0.2598(3) 0.1423(2) 0.3330(2) 0.0469(5) Uani 1 1 d . . . . .
H6A H 0.3272 0.1230 0.2680 0.056 Uiso 1 1 calc R U . . .
C7 C 0.1218(2) 0.2079(2) 0.3161(2) 0.0402(5) Uani 1 1 d . . . . .
C8 C 0.0218(3) 0.2333(3) 0.4141(2) 0.0498(6) Uani 1 1 d . . . . .
H8A H -0.0725 0.2755 0.4038 0.060 Uiso 1 1 calc R U . . .
C3 C 0.0610(3) 0.1967(3) 0.5262(2) 0.0512(6) Uani 1 1 d . . . . .
H3A H -0.0066 0.2154 0.5909 0.061 Uiso 1 1 calc R U . . .
C10 C -0.4508(4) 0.3031(5) 0.0964(4) 0.0942(11) Uani 1 1 d . . . . .
H10A H -0.5598 0.3106 0.0796 0.113 Uiso 1 1 calc R U . . .
C11 C -0.3901(4) 0.1784(4) 0.0253(4) 0.0838(9) Uani 1 1 d . . . . .
H11A H -0.4577 0.1004 -0.0400 0.101 Uiso 1 1 calc R U . . .
C12 C -0.2294(3) 0.1664(3) 0.0490(3) 0.0611(7) Uani 1 1 d . . . . .
H12A H -0.1890 0.0802 -0.0007 0.073 Uiso 1 1 calc R U . . .
C13 C -0.1265(3) 0.2808(2) 0.1460(2) 0.0458(5) Uani 1 1 d . . . . .
C14 C -0.1899(3) 0.4074(3) 0.2178(3) 0.0671(7) Uani 1 1 d . . . . .
H14A H -0.1230 0.4857 0.2833 0.080 Uiso 1 1 calc R U . . .
C9 C -0.3519(4) 0.4185(4) 0.1933(4) 0.0909(10) Uani 1 1 d . . . . .
H9A H -0.3939 0.5041 0.2423 0.109 Uiso 1 1 calc R U . . .
C16 C 0.3269(4) 0.7026(3) 0.3261(4) 0.0778(9) Uani 1 1 d . . . . .
H16A H 0.3771 0.7928 0.3555 0.093 Uiso 1 1 calc R U . . .
C17 C 0.3340(3) 0.6405(3) 0.4185(3) 0.0696(8) Uani 1 1 d . . . . .
H17A H 0.3893 0.6885 0.5106 0.083 Uiso 1 1 calc R U . . .
C18 C 0.2592(3) 0.5067(3) 0.3754(3) 0.0548(6) Uani 1 1 d . . . . .
H18A H 0.2638 0.4658 0.4392 0.066 Uiso 1 1 calc R U . . .
C19 C 0.1776(3) 0.4331(2) 0.2388(2) 0.0447(5) Uani 1 1 d . . . . .
C20 C 0.1730(3) 0.4984(3) 0.1469(3) 0.0608(7) Uani 1 1 d . . . . .
H20A H 0.1194 0.4505 0.0542 0.073 Uiso 1 1 calc R U . . .
C15 C 0.2457(4) 0.6317(3) 0.1902(4) 0.0757(8) Uani 1 1 d . . . . .
H15A H 0.2399 0.6739 0.1275 0.091 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C13 1.824(2) . ?
P1 C19 1.823(2) . ?
P1 C7 1.825(2) . ?
O1 C2 1.207(3) . ?
C1 C2 1.504(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C4 1.495(3) . ?
C4 C3 1.380(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.376(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.385(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.396(3) . ?
C8 C3 1.380(3) . ?
C8 H8A 0.9300 . ?
C3 H3A 0.9300 . ?
C10 C11 1.353(5) . ?
C10 C9 1.373(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.371(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.384(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.380(3) . ?
C14 C9 1.381(4) . ?
C14 H14A 0.9300 . ?
C9 H9A 0.9300 . ?
C16 C17 1.371(4) . ?
C16 C15 1.371(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.382(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.380(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.392(3) . ?
C20 C15 1.370(4) . ?
C20 H20A 0.9300 . ?
C15 H15A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 P1 C19 102.24(10) . . ?
C13 P1 C7 103.30(10) . . ?
C19 P1 C7 102.06(10) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C4 120.3(2) . . ?
O1 C2 C1 120.9(2) . . ?
C4 C2 C1 118.9(2) . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 C2 122.7(2) . . ?
C5 C4 C2 118.9(2) . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C5 C6 C7 121.0(2) . . ?
C5 C6 H6A 119.5 . . ?
C7 C6 H6A 119.5 . . ?
C6 C7 C8 118.1(2) . . ?
C6 C7 P1 116.65(16) . . ?
C8 C7 P1 125.24(16) . . ?
C3 C8 C7 120.9(2) . . ?
C3 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C8 C3 C4 120.8(2) . . ?
C8 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C14 C13 C12 118.3(2) . . ?
C14 C13 P1 125.2(2) . . ?
C12 C13 P1 116.50(18) . . ?
C9 C14 C13 120.5(3) . . ?
C9 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C10 C9 C14 119.8(3) . . ?
C10 C9 H9A 120.1 . . ?
C14 C9 H9A 120.1 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16A 120.1 . . ?
C15 C16 H16A 120.1 . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 H17A 119.9 . . ?
C18 C17 H17A 119.9 . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18A 119.6 . . ?
C17 C18 H18A 119.6 . . ?
C18 C19 C20 117.8(2) . . ?
C18 C19 P1 125.43(19) . . ?
C20 C19 P1 116.63(19) . . ?
C15 C20 C19 121.4(3) . . ?
C15 C20 H20A 119.3 . . ?
C19 C20 H20A 119.3 . . ?
C20 C15 C16 119.9(3) . . ?
C20 C15 H15A 120.1 . . ?
C16 C15 H15A 120.1 . . ?

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.046

