# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_compound5
_database_code_depnum_ccdc_archive 'CCDC 1447739'
_audit_update_record             
;
2016-01-16 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H26 N O4 P'
_chemical_formula_weight         471.47

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   P2(1)/n

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

_cell_length_a                   12.282(3)
_cell_length_b                   8.9370(18)
_cell_length_c                   22.179(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.60(3)
_cell_angle_gamma                90.00
_cell_volume                     2431.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2412
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      28.20

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Sheldrick (1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            22573
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4288
_reflns_number_gt                3545
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0564P)²+0.7738P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4288
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1337
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_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 0.25375(5) 0.24339(7) 0.01361(3) 0.03940(19) Uani 1 1 d . . .
O2 O 0.14722(12) 0.15142(18) -0.00134(8) 0.0455(4) Uani 1 1 d . . .
O4 O 0.22007(16) 0.05581(18) 0.11776(8) 0.0559(5) Uani 1 1 d . . .
O3 O 0.35181(13) 0.1311(2) 0.01108(8) 0.0540(5) Uani 1 1 d . . .
O1 O 0.26500(14) 0.3703(2) -0.02674(8) 0.0530(5) Uani 1 1 d . . .
N1 N 0.40956(16) 0.2770(2) 0.15989(9) 0.0427(5) Uani 1 1 d . . .
C1 C 0.25101(18) 0.3114(3) 0.09314(10) 0.0368(5) Uani 1 1 d . . .
C18 C 0.17464(19) 0.4478(2) 0.09628(10) 0.0363(5) Uani 1 1 d . . .
C2 C 0.36943(19) 0.3486(3) 0.11229(11) 0.0386(5) Uani 1 1 d . . .
C11 C 0.21074(18) 0.1848(3) 0.13390(11) 0.0398(6) Uani 1 1 d . . .
C4 C 0.5343(2) 0.4800(3) 0.09638(12) 0.0503(7) Uani 1 1 d . . .
H4 H 0.5753 0.5470 0.0747 0.060 Uiso 1 1 calc R . .
C19 C 0.0672(2) 0.4348(3) 0.07575(11) 0.0451(6) Uani 1 1 d . . .
H19 H 0.0437 0.3461 0.0575 0.054 Uiso 1 1 calc R . .
C5 C 0.58133(19) 0.4069(3) 0.14724(12) 0.0480(6) Uani 1 1 d . . .
C10 C 0.5156(2) 0.3063(3) 0.17832(12) 0.0471(6) Uani 1 1 d . . .
C12 C 0.1514(2) 0.2191(3) 0.18952(11) 0.0418(6) Uani 1 1 d . . .
C25 C 0.2444(2) -0.0731(3) -0.03646(12) 0.0508(7) Uani 1 1 d . . .
C21 C 0.0279(2) 0.6815(3) 0.10905(12) 0.0566(7) Uani 1 1 d . . .
H21 H -0.0211 0.7596 0.1134 0.068 Uiso 1 1 calc R . .
C17 C 0.1803(2) 0.3314(3) 0.23018(12) 0.0510(7) Uani 1 1 d . . .
H17 H 0.2418 0.3896 0.2244 0.061 Uiso 1 1 calc R . .
C23 C 0.2072(2) 0.5808(3) 0.12377(12) 0.0482(6) Uani 1 1 d . . .
H23 H 0.2790 0.5922 0.1382 0.058 Uiso 1 1 calc R . .
C20 C -0.0060(2) 0.5504(3) 0.08163(12) 0.0531(7) Uani 1 1 d . . .
H20 H -0.0778 0.5398 0.0671 0.064 Uiso 1 1 calc R . .
C3 C 0.4293(2) 0.4524(3) 0.07912(12) 0.0465(6) Uani 1 1 d . . .
H3 H 0.3969 0.5012 0.0459 0.056 Uiso 1 1 calc R . .
C22 C 0.1337(2) 0.6967(3) 0.12990(13) 0.0563(7) Uani 1 1 d . . .
H22 H 0.1565 0.7855 0.1483 0.068 Uiso 1 1 calc R . .
C13 C 0.0598(2) 0.1333(3) 0.19953(13) 0.0563(7) Uani 1 1 d . . .
H13 H 0.0405 0.0559 0.1731 0.068 Uiso 1 1 calc R . .
C24 C 0.1421(2) -0.0090(3) -0.01110(12) 0.0485(6) Uani 1 1 d . . .
H24A H 0.0807 -0.0312 -0.0387 0.058 Uiso 1 1 calc R . .
H24B H 0.1293 -0.0580 0.0270 0.058 Uiso 1 1 calc R . .
C26 C 0.3403(2) -0.0306(3) 0.00521(14) 0.0564(7) Uani 1 1 d . . .
H26A H 0.3307 -0.0738 0.0447 0.068 Uiso 1 1 calc R . .
H26B H 0.4065 -0.0719 -0.0103 0.068 Uiso 1 1 calc R . .
C6 C 0.6897(2) 0.4319(4) 0.16875(15) 0.0646(8) Uani 1 1 d . . .
H6 H 0.7344 0.4959 0.1479 0.078 Uiso 1 1 calc R . .
C14 C -0.0024(3) 0.1616(4) 0.24785(16) 0.0737(9) Uani 1 1 d . . .
H14 H -0.0645 0.1049 0.2536 0.088 Uiso 1 1 calc R . .
C16 C 0.1177(3) 0.3570(4) 0.27940(13) 0.0663(8) Uani 1 1 d . . .
H16 H 0.1376 0.4315 0.3070 0.080 Uiso 1 1 calc R . .
C9 C 0.5584(3) 0.2358(3) 0.23089(14) 0.0658(8) Uani 1 1 d . . .
H9 H 0.5155 0.1700 0.2520 0.079 Uiso 1 1 calc R . .
C15 C 0.0264(3) 0.2726(4) 0.28749(15) 0.0732(9) Uani 1 1 d . . .
H15 H -0.0162 0.2912 0.3203 0.088 Uiso 1 1 calc R . .
C7 C 0.7288(3) 0.3628(4) 0.21966(18) 0.0814(11) Uani 1 1 d . . .
H7 H 0.7999 0.3812 0.2340 0.098 Uiso 1 1 calc R . .
C27 C 0.2598(3) -0.0171(4) -0.10050(13) 0.0716(9) Uani 1 1 d . . .
H27A H 0.2627 0.0902 -0.1005 0.107 Uiso 1 1 calc R . .
H27B H 0.1998 -0.0499 -0.1265 0.107 Uiso 1 1 calc R . .
H27C H 0.3266 -0.0564 -0.1149 0.107 Uiso 1 1 calc R . .
C28 C 0.2330(3) -0.2439(3) -0.03535(17) 0.0760(10) Uani 1 1 d . . .
H28A H 0.3002 -0.2890 -0.0463 0.114 Uiso 1 1 calc R . .
H28B H 0.1755 -0.2740 -0.0636 0.114 Uiso 1 1 calc R . .
H28C H 0.2160 -0.2757 0.0045 0.114 Uiso 1 1 calc R . .
C8 C 0.6636(3) 0.2644(4) 0.25078(17) 0.0823(11) Uani 1 1 d . . .
H8 H 0.6918 0.2176 0.2855 0.099 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4554(18) . ?
P1 O2 1.5678(17) . ?
P1 O3 1.5706(18) . ?
P1 C1 1.867(2) . ?
O2 C24 1.451(3) . ?
O4 C11 1.214(3) . ?
O3 C26 1.458(3) . ?
N1 C2 1.311(3) . ?
N1 C10 1.372(3) . ?
C1 C2 1.533(3) . ?
C1 C18 1.542(3) . ?
C1 C11 1.543(3) . ?
C18 C19 1.381(3) . ?
C18 C23 1.386(3) . ?
C2 C3 1.411(3) . ?
C11 C12 1.493(3) . ?
C4 C3 1.352(3) . ?
C4 C5 1.405(4) . ?
C19 C20 1.380(3) . ?
C5 C10 1.409(4) . ?
C5 C6 1.411(4) . ?
C10 C9 1.406(4) . ?
C12 C17 1.385(4) . ?
C12 C13 1.388(3) . ?
C25 C24 1.512(3) . ?
C25 C26 1.513(4) . ?
C25 C27 1.526(4) . ?
C25 C28 1.533(4) . ?
C21 C22 1.366(4) . ?
C21 C20 1.376(4) . ?
C17 C16 1.383(4) . ?
C23 C22 1.385(4) . ?
C13 C14 1.367(4) . ?
C6 C7 1.356(5) . ?
C14 C15 1.361(5) . ?
C16 C15 1.370(4) . ?
C9 C8 1.370(4) . ?
C7 C8 1.393(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
O1 P1 O2 112.35(10) . . ?
O1 P1 O3 112.44(10) . . ?
O2 P1 O3 106.94(9) . . ?
O1 P1 C1 109.47(10) . . ?
O2 P1 C1 108.65(10) . . ?
O3 P1 C1 106.77(10) . . ?
C24 O2 P1 125.43(15) . . ?
C26 O3 P1 124.42(16) . . ?
C2 N1 C10 117.6(2) . . ?
C2 C1 C18 112.82(18) . . ?
C2 C1 C11 108.76(18) . . ?
C18 C1 C11 109.96(18) . . ?
C2 C1 P1 105.94(15) . . ?
C18 C1 P1 109.71(16) . . ?
C11 C1 P1 109.55(16) . . ?
C19 C18 C23 118.0(2) . . ?
C19 C18 C1 119.5(2) . . ?
C23 C18 C1 122.3(2) . . ?
N1 C2 C3 123.7(2) . . ?
N1 C2 C1 115.8(2) . . ?
C3 C2 C1 120.5(2) . . ?
O4 C11 C12 119.7(2) . . ?
O4 C11 C1 119.1(2) . . ?
C12 C11 C1 121.0(2) . . ?
C3 C4 C5 119.7(2) . . ?
C20 C19 C18 121.5(2) . . ?
C4 C5 C10 117.7(2) . . ?
C4 C5 C6 123.0(3) . . ?
C10 C5 C6 119.2(3) . . ?
N1 C10 C9 118.4(3) . . ?
N1 C10 C5 122.2(2) . . ?
C9 C10 C5 119.3(3) . . ?
C17 C12 C13 118.8(2) . . ?
C17 C12 C11 124.5(2) . . ?
C13 C12 C11 116.6(2) . . ?
C24 C25 C26 108.3(2) . . ?
C24 C25 C27 111.2(2) . . ?
C26 C25 C27 111.1(2) . . ?
C24 C25 C28 107.1(2) . . ?
C26 C25 C28 108.0(3) . . ?
C27 C25 C28 110.9(2) . . ?
C22 C21 C20 119.9(2) . . ?
C16 C17 C12 119.9(3) . . ?
C22 C23 C18 120.6(2) . . ?
C21 C20 C19 119.6(3) . . ?
C4 C3 C2 119.0(2) . . ?
C21 C22 C23 120.4(3) . . ?
C14 C13 C12 120.6(3) . . ?
O2 C24 C25 113.5(2) . . ?
O3 C26 C25 111.9(2) . . ?
C7 C6 C5 120.2(3) . . ?
C15 C14 C13 120.2(3) . . ?
C15 C16 C17 120.0(3) . . ?
C8 C9 C10 119.7(3) . . ?
C14 C15 C16 120.4(3) . . ?
C6 C7 C8 120.7(3) . . ?
C9 C8 C7 120.9(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.043
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound9
_database_code_depnum_ccdc_archive 'CCDC 1447740'
_audit_update_record             
;
2016-01-16 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H28 N O4 P'
_chemical_formula_sum            'C29 H28 N O4 P'
_chemical_formula_weight         485.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.4790(9)
_cell_length_b                   10.8907(9)
_cell_length_c                   12.8985(9)
_cell_angle_alpha                68.115(7)
_cell_angle_beta                 68.507(7)
_cell_angle_gamma                89.099(7)
_cell_volume                     1258.45(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3859
_cell_measurement_theta_min      4.0050
_cell_measurement_theta_max      71.6070

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512.0
_exptl_absorpt_coefficient_mu    1.255
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.69580
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8508
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.01
_diffrn_reflns_theta_max         71.79
_reflns_number_total             4810
_reflns_number_gt                4088
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0759P)²+0.2587P] 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         4810
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1358
_refine_ls_wR_factor_gt          0.1279
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.39722(5) 0.87219(4) 0.35818(4) 0.04172(15) Uani 1 1 d . . .
O4 O 0.33007(13) 0.88022(12) 0.26448(12) 0.0433(3) Uani 1 1 d . . .
N1 N 0.52259(16) 0.74825(14) 0.12121(13) 0.0411(3) Uani 1 1 d . . .
O1 O 0.55539(14) 0.91154(13) 0.27844(14) 0.0504(3) Uani 1 1 d . . .
O2 O 0.35222(15) 0.99613(13) 0.39004(13) 0.0503(3) Uani 1 1 d . . .
O3 O 0.36147(18) 0.74818(15) 0.46359(14) 0.0629(4) Uani 1 1 d . . .
C5 C 0.6608(2) 0.73762(18) 0.08613(17) 0.0432(4) Uani 1 1 d . . .
C3 C 0.6165(2) 0.53844(18) 0.26663(19) 0.0480(4) Uani 1 1 d . . .
H3 H 0.6477 0.4688 0.3154 0.058 Uiso 1 1 calc R . .
C10 C 0.28564(18) 0.67211(17) 0.25619(15) 0.0382(4) Uani 1 1 d . . .
C2 C 0.4791(2) 0.54975(17) 0.30463(17) 0.0430(4) Uani 1 1 d . . .
C11 C 0.19695(19) 0.55924(16) 0.26538(16) 0.0406(4) Uani 1 1 d . . .
C4 C 0.7128(2) 0.6306(2) 0.15439(19) 0.0474(4) Uani 1 1 d . . .
C17 C 0.23877(18) 0.78140(17) 0.27193(16) 0.0388(4) Uani 1 1 d . . .
C26 C 0.5542(2) 1.1538(2) 0.22410(19) 0.0531(5) Uani 1 1 d . . .
C25 C 0.6007(2) 1.0424(2) 0.1797(2) 0.0552(5) Uani 1 1 d . . .
H25A H 0.5633 1.0463 0.1202 0.066 Uiso 1 1 calc R . .
H25B H 0.7010 1.0562 0.1403 0.066 Uiso 1 1 calc R . .
C1 C 0.43626(18) 0.65785(16) 0.22518(16) 0.0385(4) Uani 1 1 d . . .
C18 C 0.09875(19) 0.82041(17) 0.29464(17) 0.0424(4) Uani 1 1 d . . .
C29 C 0.3978(2) 1.1274(2) 0.2906(2) 0.0555(5) Uani 1 1 d . . .
H29A H 0.3676 1.1955 0.3222 0.067 Uiso 1 1 calc R . .
H29B H 0.3551 1.1331 0.2340 0.067 Uiso 1 1 calc R . .
C16 C 0.0610(2) 0.51494(19) 0.34865(18) 0.0488(4) Uani 1 1 d . . .
H16 H 0.0211 0.5575 0.4010 0.059 Uiso 1 1 calc R . .
C9 C 0.8566(2) 0.6233(3) 0.1078(2) 0.0625(6) Uani 1 1 d . . .
H9 H 0.8923 0.5519 0.1499 0.075 Uiso 1 1 calc R . .
C6 C 0.7542(2) 0.8379(2) -0.02254(19) 0.0536(5) Uani 1 1 d . . .
H6 H 0.7212 0.9105 -0.0663 0.064 Uiso 1 1 calc R . .
C12 C 0.2540(2) 0.49246(19) 0.18940(18) 0.0493(4) Uani 1 1 d . . .
H12 H 0.3454 0.5191 0.1341 0.059 Uiso 1 1 calc R . .
C15 C -0.0158(2) 0.4085(2) 0.3548(2) 0.0603(5) Uani 1 1 d . . .
H15 H -0.1067 0.3800 0.4110 0.072 Uiso 1 1 calc R . .
C23 C 0.0398(2) 0.8706(2) 0.3831(2) 0.0529(5) Uani 1 1 d . . .
H23 H 0.0914 0.8847 0.4240 0.064 Uiso 1 1 calc R . .
C24 C 0.3773(2) 0.4551(2) 0.42643(19) 0.0559(5) Uani 1 1 d . . .
H24A H 0.3183 0.3988 0.4152 0.084 Uiso 1 1 calc R . .
H24B H 0.3220 0.5053 0.4694 0.084 Uiso 1 1 calc R . .
H24C H 0.4266 0.4008 0.4723 0.084 Uiso 1 1 calc R . .
C7 C 0.8922(2) 0.8287(3) -0.0633(2) 0.0643(6) Uani 1 1 d . . .
H7 H 0.9530 0.8951 -0.1347 0.077 Uiso 1 1 calc R . .
C27 C 0.6238(3) 1.1613(2) 0.3073(2) 0.0704(7) Uani 1 1 d . . .
H27A H 0.5942 1.2328 0.3329 0.106 Uiso 1 1 calc R . .
H27B H 0.7225 1.1773 0.2642 0.106 Uiso 1 1 calc R . .
H27C H 0.5984 1.0783 0.3769 0.106 Uiso 1 1 calc R . .
C8 C 0.9426(2) 0.7203(3) 0.0014(2) 0.0692(6) Uani 1 1 d . . .
H8 H 1.0367 0.7140 -0.0285 0.083 Uiso 1 1 calc R . .
C20 C -0.1130(3) 0.8349(2) 0.2606(3) 0.0681(7) Uani 1 1 d . . .
H20 H -0.1644 0.8234 0.2186 0.082 Uiso 1 1 calc R . .
C14 C 0.0419(3) 0.3448(2) 0.2779(2) 0.0649(6) Uani 1 1 d . . .
H14 H -0.0100 0.2733 0.2821 0.078 Uiso 1 1 calc R . .
C19 C 0.0218(2) 0.8063(2) 0.2310(2) 0.0554(5) Uani 1 1 d . . .
H19 H 0.0611 0.7775 0.1681 0.066 Uiso 1 1 calc R . .
C28 C 0.5912(4) 1.2856(3) 0.1140(3) 0.0852(9) Uani 1 1 d . . .
H28A H 0.5460 1.2802 0.0629 0.128 Uiso 1 1 calc R . .
H28B H 0.6897 1.3031 0.0694 0.128 Uiso 1 1 calc R . .
H28C H 0.5613 1.3567 0.1403 0.128 Uiso 1 1 calc R . .
C13 C 0.1759(3) 0.3867(2) 0.1952(2) 0.0622(6) Uani 1 1 d . . .
H13 H 0.2146 0.3440 0.1428 0.075 Uiso 1 1 calc R . .
C21 C -0.1711(2) 0.8797(2) 0.3512(3) 0.0707(7) Uani 1 1 d . . .
H21 H -0.2625 0.8965 0.3721 0.085 Uiso 1 1 calc R . .
C22 C -0.0943(2) 0.9001(2) 0.4116(2) 0.0666(6) Uani 1 1 d . . .
H22 H -0.1326 0.9336 0.4712 0.080 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 O3 1.4446(15) . ?
P1 O1 1.5599(15) . ?
P1 O2 1.5699(13) . ?
P1 O4 1.5831(12) . ?
O4 C17 1.404(2) . ?
N1 C1 1.319(2) . ?
N1 C5 1.367(2) . ?
O1 C25 1.451(3) . ?
O2 C29 1.457(2) . ?
C5 C4 1.413(3) . ?
C5 C6 1.415(3) . ?
C3 C2 1.361(3) . ?
C3 C4 1.414(3) . ?
C10 C17 1.337(2) . ?
C10 C11 1.495(2) . ?
C10 C1 1.500(2) . ?
C2 C1 1.435(2) . ?
C2 C24 1.506(3) . ?
C11 C16 1.389(3) . ?
C11 C12 1.391(3) . ?
C4 C9 1.416(3) . ?
C17 C18 1.476(2) . ?
C26 C29 1.518(3) . ?
C26 C28 1.524(3) . ?
C26 C27 1.526(3) . ?
C26 C25 1.528(3) . ?
C18 C23 1.386(3) . ?
C18 C19 1.390(3) . ?
C16 C15 1.383(3) . ?
C9 C8 1.362(4) . ?
C6 C7 1.362(3) . ?
C12 C13 1.387(3) . ?
C15 C14 1.375(4) . ?
C23 C22 1.382(3) . ?
C7 C8 1.392(4) . ?
C20 C21 1.368(4) . ?
C20 C19 1.385(3) . ?
C14 C13 1.370(4) . ?
C21 C22 1.377(4) . ?

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
O3 P1 O1 114.49(9) . . ?
O3 P1 O2 113.37(9) . . ?
O1 P1 O2 104.63(7) . . ?
O3 P1 O4 116.36(8) . . ?
O1 P1 O4 103.67(8) . . ?
O2 P1 O4 102.89(7) . . ?
C17 O4 P1 127.74(11) . . ?
C1 N1 C5 118.26(15) . . ?
C25 O1 P1 117.54(12) . . ?
C29 O2 P1 117.14(12) . . ?
N1 C5 C4 122.35(18) . . ?
N1 C5 C6 118.35(18) . . ?
C4 C5 C6 119.30(19) . . ?
C2 C3 C4 121.22(17) . . ?
C17 C10 C11 124.12(16) . . ?
C17 C10 C1 120.24(15) . . ?
C11 C10 C1 115.63(14) . . ?
C3 C2 C1 117.12(17) . . ?
C3 C2 C24 121.29(17) . . ?
C1 C2 C24 121.57(17) . . ?
C16 C11 C12 118.07(17) . . ?
C16 C11 C10 123.22(16) . . ?
C12 C11 C10 118.69(17) . . ?
C5 C4 C3 117.09(18) . . ?
C5 C4 C9 118.6(2) . . ?
C3 C4 C9 124.33(19) . . ?
C10 C17 O4 119.64(15) . . ?
C10 C17 C18 129.51(16) . . ?
O4 C17 C18 110.83(14) . . ?
C29 C26 C28 108.1(2) . . ?
C29 C26 C27 110.45(19) . . ?
C28 C26 C27 110.22(19) . . ?
C29 C26 C25 108.61(16) . . ?
C28 C26 C25 108.4(2) . . ?
C27 C26 C25 110.97(19) . . ?
O1 C25 C26 111.76(16) . . ?
N1 C1 C2 123.81(17) . . ?
N1 C1 C10 115.63(15) . . ?
C2 C1 C10 120.55(16) . . ?
C23 C18 C19 118.31(18) . . ?
C23 C18 C17 119.81(17) . . ?
C19 C18 C17 121.88(17) . . ?
O2 C29 C26 111.72(16) . . ?
C15 C16 C11 120.9(2) . . ?
C8 C9 C4 120.2(2) . . ?
C7 C6 C5 120.3(2) . . ?
C13 C12 C11 120.7(2) . . ?
C14 C15 C16 120.2(2) . . ?
C22 C23 C18 121.1(2) . . ?
C6 C7 C8 120.3(2) . . ?
C9 C8 C7 121.2(2) . . ?
C21 C20 C19 120.5(2) . . ?
C13 C14 C15 119.9(2) . . ?
C20 C19 C18 120.3(2) . . ?
C14 C13 C12 120.2(2) . . ?
C20 C21 C22 120.0(2) . . ?
C21 C22 C23 119.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        71.79
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.045
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound18
_database_code_depnum_ccdc_archive 'CCDC 1447741'
_audit_update_record             
;
2016-01-16 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N O'
_chemical_formula_weight         221.25

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   17.8590(16)
_cell_length_b                   5.8124(4)
_cell_length_c                   21.742(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.101(10)
_cell_angle_gamma                90.00
_cell_volume                     2168.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1458
_cell_measurement_theta_min      3.7510
_cell_measurement_theta_max      28.0760

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.76412
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            3812
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1902
_reflns_number_gt                1497
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0552P)²+0.5816P] 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         1902
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
N1 N 0.03903(7) 0.2481(2) 0.46928(6) 0.0379(3) Uani 1 1 d . . .
C2 C 0.15343(8) 0.0925(2) 0.54297(7) 0.0342(4) Uani 1 1 d . . .
O1 O 0.09344(6) 0.44566(17) 0.56015(5) 0.0467(3) Uani 1 1 d . . .
C3 C 0.21561(8) 0.1060(2) 0.60434(7) 0.0352(4) Uani 1 1 d . . .
C15 C 0.03475(8) 0.0695(2) 0.42678(7) 0.0354(4) Uani 1 1 d . . .
C9 C 0.14861(8) -0.0870(2) 0.50272(7) 0.0361(4) Uani 1 1 d . . .
H9 H 0.1852 -0.2043 0.5146 0.043 Uiso 1 1 calc R . .
C11 C 0.08580(9) -0.2874(3) 0.39962(7) 0.0425(4) Uani 1 1 d . . .
H11 H 0.1224 -0.4052 0.4094 0.051 Uiso 1 1 calc R . .
C1 C 0.09479(8) 0.2757(2) 0.52614(7) 0.0358(4) Uani 1 1 d . . .
C14 C -0.02370(9) 0.0631(3) 0.36910(7) 0.0446(4) Uani 1 1 d . . .
H14 H -0.0603 0.1808 0.3585 0.054 Uiso 1 1 calc R . .
C10 C 0.09038(8) -0.1063(2) 0.44292(7) 0.0351(4) Uani 1 1 d . . .
C4 C 0.22913(9) -0.0765(3) 0.64713(7) 0.0421(4) Uani 1 1 d . . .
H4 H 0.1977 -0.2065 0.6377 0.050 Uiso 1 1 calc R . .
C5 C 0.28857(9) -0.0682(3) 0.70341(8) 0.0499(4) Uani 1 1 d . . .
H5 H 0.2960 -0.1904 0.7321 0.060 Uiso 1 1 calc R . .
C8 C 0.26449(9) 0.2963(3) 0.61943(8) 0.0462(4) Uani 1 1 d . . .
H8 H 0.2563 0.4216 0.5917 0.055 Uiso 1 1 calc R . .
C13 C -0.02699(10) -0.1176(3) 0.32813(8) 0.0512(5) Uani 1 1 d . . .
H13 H -0.0664 -0.1231 0.2899 0.061 Uiso 1 1 calc R . .
C12 C 0.02788(10) -0.2932(3) 0.34300(8) 0.0502(4) Uani 1 1 d . . .
H12 H 0.0253 -0.4145 0.3146 0.060 Uiso 1 1 calc R . .
C7 C 0.32490(10) 0.3016(3) 0.67486(9) 0.0553(5) Uani 1 1 d . . .
H7 H 0.3579 0.4284 0.6837 0.066 Uiso 1 1 calc R . .
C6 C 0.33677(10) 0.1208(3) 0.71712(8) 0.0544(5) Uani 1 1 d . . .
H6 H 0.3772 0.1260 0.7548 0.065 Uiso 1 1 calc R . .
H1D H 0.0016(10) 0.354(3) 0.4598(8) 0.057(5) 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
N1 C1 1.3648(18) . ?
N1 C15 1.3777(18) . ?
N1 H1D 0.892(18) . ?
C2 C9 1.3489(19) . ?
C2 C1 1.4673(19) . ?
C2 C3 1.482(2) . ?
O1 C1 1.2380(17) . ?
C3 C4 1.3872(19) . ?
C3 C8 1.391(2) . ?
C15 C14 1.392(2) . ?
C15 C10 1.401(2) . ?
C9 C10 1.4264(19) . ?
C9 H9 0.9300 . ?
C11 C12 1.371(2) . ?
C11 C10 1.399(2) . ?
C11 H11 0.9300 . ?
C14 C13 1.368(2) . ?
C14 H14 0.9300 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(2) . ?
C5 H5 0.9300 . ?
C8 C7 1.377(2) . ?
C8 H8 0.9300 . ?
C13 C12 1.389(2) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C7 C6 1.373(2) . ?
C7 H7 0.9300 . ?
C6 H6 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
C1 N1 C15 125.94(12) . . ?
C1 N1 H1D 116.1(11) . . ?
C15 N1 H1D 118.0(11) . . ?
C9 C2 C1 119.12(13) . . ?
C9 C2 C3 121.48(12) . . ?
C1 C2 C3 119.39(12) . . ?
C4 C3 C8 117.96(14) . . ?
C4 C3 C2 120.70(13) . . ?
C8 C3 C2 121.26(13) . . ?
N1 C15 C14 120.86(13) . . ?
N1 C15 C10 118.57(13) . . ?
C14 C15 C10 120.57(14) . . ?
C2 C9 C10 123.49(13) . . ?
C2 C9 H9 118.3 . . ?
C10 C9 H9 118.3 . . ?
C12 C11 C10 120.73(14) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
O1 C1 N1 120.31(12) . . ?
O1 C1 C2 124.11(13) . . ?
N1 C1 C2 115.58(13) . . ?
C13 C14 C15 119.57(14) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C11 C10 C15 118.39(13) . . ?
C11 C10 C9 124.36(13) . . ?
C15 C10 C9 117.25(13) . . ?
C5 C4 C3 121.04(15) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 120.06(15) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C8 C3 120.82(15) . . ?
C7 C8 H8 119.6 . . ?
C3 C8 H8 119.6 . . ?
C14 C13 C12 120.81(15) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C11 C12 C13 119.92(15) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C6 C7 C8 120.44(16) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C6 C5 119.65(15) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound19
_database_code_depnum_ccdc_archive 'CCDC 1447742'
_audit_update_record             
;
2016-01-16 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Cl N O'
_chemical_formula_weight         255.69

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'
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   C2/c

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                   17.482(4)
_cell_length_b                   5.9043(13)
_cell_length_c                   23.251(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.505(3)
_cell_angle_gamma                90.00
_cell_volume                     2359.7(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6788
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.91

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Sheldrick (1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            10254
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2057
_reflns_number_gt                1727
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0617P)²+1.8325P] 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         2057
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
Cl1 Cl 0.37944(4) 0.09262(14) 0.25997(3) 0.0890(3) Uani 1 1 d . . .
N1 N 0.04269(9) 0.2572(3) -0.03014(7) 0.0409(4) Uani 1 1 d . . .
C7 C 0.14608(11) -0.0843(3) -0.00073(8) 0.0400(5) Uani 1 1 d . . .
H7 H 0.1806 -0.2034 0.0097 0.048 Uiso 1 1 calc R . .
O1 O 0.08839(8) 0.4426(2) 0.05373(6) 0.0498(4) Uani 1 1 d . . .
C10 C 0.20378(10) 0.0968(3) 0.09273(8) 0.0381(4) Uani 1 1 d . . .
C8 C 0.14790(10) 0.0908(3) 0.03655(8) 0.0374(4) Uani 1 1 d . . .
C1 C 0.04178(10) 0.0831(3) -0.06958(8) 0.0389(4) Uani 1 1 d . . .
C6 C 0.09373(11) -0.0960(3) -0.05540(8) 0.0389(4) Uani 1 1 d . . .
C2 C -0.01024(12) 0.0867(4) -0.12256(9) 0.0481(5) Uani 1 1 d . . .
H2 H -0.0443 0.2076 -0.1320 0.058 Uiso 1 1 calc R . .
C11 C 0.21212(11) -0.0904(3) 0.12893(9) 0.0446(5) Uani 1 1 d . . .
H11 H 0.1814 -0.2175 0.1183 0.053 Uiso 1 1 calc R . .
C9 C 0.09255(10) 0.2768(3) 0.02206(8) 0.0384(4) Uani 1 1 d . . .
C12 C 0.26565(12) -0.0914(4) 0.18088(9) 0.0521(6) Uani 1 1 d . . .
H12 H 0.2706 -0.2173 0.2053 0.063 Uiso 1 1 calc R . .
C4 C 0.04019(13) -0.2708(4) -0.14725(10) 0.0567(6) Uani 1 1 d . . .
H4 H 0.0389 -0.3902 -0.1735 0.068 Uiso 1 1 calc R . .
C14 C 0.30508(12) 0.2831(4) 0.16041(10) 0.0577(6) Uani 1 1 d . . .
H14 H 0.3372 0.4079 0.1707 0.069 Uiso 1 1 calc R . .
C13 C 0.31128(12) 0.0965(4) 0.19559(9) 0.0529(6) Uani 1 1 d . . .
C5 C 0.09221(11) -0.2737(4) -0.09546(9) 0.0480(5) Uani 1 1 d . . .
H5 H 0.1266 -0.3943 -0.0869 0.058 Uiso 1 1 calc R . .
C15 C 0.25037(12) 0.2841(4) 0.10922(10) 0.0505(5) Uani 1 1 d . . .
H15 H 0.2448 0.4123 0.0856 0.061 Uiso 1 1 calc R . .
C3 C -0.01058(13) -0.0901(4) -0.16055(9) 0.0564(6) Uani 1 1 d . . .
H3 H -0.0455 -0.0891 -0.1959 0.068 Uiso 1 1 calc R . .
H1 H 0.0069(13) 0.365(4) -0.0377(9) 0.048(6) 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
Cl1 C13 1.735(2) . ?
N1 C9 1.364(2) . ?
N1 C1 1.376(2) . ?
N1 H1 0.89(2) . ?
C7 C8 1.346(3) . ?
C7 C6 1.426(3) . ?
C7 H7 0.9300 . ?
O1 C9 1.235(2) . ?
C10 C11 1.381(3) . ?
C10 C15 1.386(3) . ?
C10 C8 1.482(2) . ?
C8 C9 1.462(2) . ?
C1 C2 1.391(3) . ?
C1 C6 1.394(3) . ?
C6 C5 1.400(3) . ?
C2 C3 1.366(3) . ?
C2 H2 0.9300 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(3) . ?
C12 H12 0.9300 . ?
C4 C5 1.370(3) . ?
C4 C3 1.386(3) . ?
C4 H4 0.9300 . ?
C14 C13 1.365(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9300 . ?
C5 H5 0.9300 . ?
C15 H15 0.9300 . ?
C3 H3 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
C9 N1 C1 125.75(16) . . ?
C9 N1 H1 115.3(14) . . ?
C1 N1 H1 118.9(14) . . ?
C8 C7 C6 123.18(17) . . ?
C8 C7 H7 118.4 . . ?
C6 C7 H7 118.4 . . ?
C11 C10 C15 118.60(18) . . ?
C11 C10 C8 119.86(17) . . ?
C15 C10 C8 121.51(17) . . ?
C7 C8 C9 119.45(17) . . ?
C7 C8 C10 121.35(16) . . ?
C9 C8 C10 119.18(16) . . ?
N1 C1 C2 120.34(17) . . ?
N1 C1 C6 118.77(17) . . ?
C2 C1 C6 120.89(18) . . ?
C1 C6 C5 118.60(18) . . ?
C1 C6 C7 117.31(17) . . ?
C5 C6 C7 124.09(17) . . ?
C3 C2 C1 119.07(19) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C10 C11 C12 120.95(19) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
O1 C9 N1 120.01(16) . . ?
O1 C9 C8 124.51(16) . . ?
N1 C9 C8 115.48(16) . . ?
C13 C12 C11 118.86(19) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C13 C14 C15 119.0(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C13 C12 121.61(19) . . ?
C14 C13 Cl1 119.63(18) . . ?
C12 C13 Cl1 118.75(18) . . ?
C4 C5 C6 120.27(19) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C14 C15 C10 120.9(2) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.064
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compd26
_database_code_depnum_ccdc_archive 'CCDC 1447743'
_audit_update_record             
;
2016-01-16 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H25 Cl N O2 P'
_chemical_formula_weight         557.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   9.6939(19)
_cell_length_b                   21.405(4)
_cell_length_c                   27.668(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 80.83(3)
_cell_angle_gamma                90.00
_cell_volume                     5667.7(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6239
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.32

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2320
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9565
_exptl_absorpt_correction_T_max  0.9779
_exptl_absorpt_process_details   'SADABS, Sheldrick (1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            54007
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.21
_diffrn_reflns_theta_max         25.00
_reflns_number_total             9976
_reflns_number_gt                6188
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. The data quality was not
 good and disorder was found at atoms C41 and C42.  
;

_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)+(0.0863P)²+8.5181P] 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         9976
_refine_ls_number_parameters     721
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1643
_refine_ls_R_factor_gt           0.1094
_refine_ls_wR_factor_ref         0.2583
_refine_ls_wR_factor_gt          0.2299
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.24305(15) 0.66422(6) 0.64728(5) 0.0529(4) Uani 1 1 d . . .
P2 P 0.21177(19) 0.54454(7) 0.87671(5) 0.0663(5) Uani 1 1 d . . .
Cl2 Cl -0.3111(3) 0.49208(11) 0.73847(9) 0.1287(9) Uani 1 1 d . . .
Cl1 Cl 0.7999(2) 0.71758(10) 0.76922(8) 0.1140(8) Uani 1 1 d . . .
N1 N 0.2661(4) 0.5208(2) 0.62753(15) 0.0527(11) Uani 1 1 d . . .
O1 O 0.1518(4) 0.64899(18) 0.69347(13) 0.0704(11) Uani 1 1 d . . .
O4 O -0.0207(4) 0.56649(19) 0.95748(13) 0.0705(11) Uani 1 1 d . . .
C1 C 0.3383(5) 0.5467(2) 0.65862(18) 0.0488(13) Uani 1 1 d . . .
O3 O 0.3121(5) 0.5552(2) 0.83167(14) 0.0880(14) Uani 1 1 d . . .
O2 O 0.4563(4) 0.64446(19) 0.55891(13) 0.0675(11) Uani 1 1 d . . .
C18 C 0.5045(6) 0.6388(2) 0.67367(18) 0.0526(13) Uani 1 1 d . . .
C10 C 0.4019(5) 0.6104(2) 0.64155(17) 0.0456(12) Uani 1 1 d . . .
C11 C 0.4750(5) 0.6044(2) 0.58831(19) 0.0496(13) Uani 1 1 d . . .
C65 C -0.1166(5) 0.6631(3) 0.9423(2) 0.0559(14) Uani 1 1 d . . .
C5 C 0.2005(6) 0.4654(2) 0.6398(2) 0.0591(15) Uani 1 1 d . . .
C12 C 0.5742(5) 0.5521(2) 0.57353(19) 0.0504(13) Uani 1 1 d . . .
C45 C 0.0592(6) 0.6015(3) 0.87613(19) 0.0624(16) Uani 1 1 d . . .
C24 C 0.1465(5) 0.6574(2) 0.59636(19) 0.0544(14) Uani 1 1 d . . .
C13 C 0.6157(6) 0.5405(3) 0.5238(2) 0.0713(17) Uani 1 1 d . . .
H13 H 0.5823 0.5655 0.5007 0.086 Uiso 1 1 calc R . .
C22 C 0.5515(8) 0.6740(3) 0.7525(2) 0.0780(19) Uani 1 1 d . . .
H22 H 0.5216 0.6811 0.7857 0.094 Uiso 1 1 calc R . .
C64 C -0.0248(6) 0.6079(3) 0.9279(2) 0.0545(13) Uani 1 1 d . . .
C19 C 0.6386(6) 0.6543(3) 0.6547(2) 0.0645(15) Uani 1 1 d . . .
H19 H 0.6690 0.6484 0.6214 0.077 Uiso 1 1 calc R . .
C58 C 0.2942(6) 0.5570(3) 0.9301(2) 0.0634(15) Uani 1 1 d . . .
C20 C 0.7322(7) 0.6788(3) 0.6832(2) 0.0729(17) Uani 1 1 d . . .
H20 H 0.8234 0.6889 0.6694 0.088 Uiso 1 1 calc R . .
C46 C -0.0373(9) 0.5753(3) 0.8412(2) 0.0702(18) Uani 1 1 d . . .
C50 C -0.2725(10) 0.5416(3) 0.8245(2) 0.097(3) Uani 1 1 d . . .
H50 H -0.3679 0.5373 0.8354 0.117 Uiso 1 1 calc R . .
C21 C 0.6852(8) 0.6874(3) 0.7319(3) 0.0769(19) Uani 1 1 d . . .
C31 C 0.3002(6) 0.7445(2) 0.64727(19) 0.0597(15) Uani 1 1 d D . .
C29 C 0.0398(6) 0.6139(3) 0.6006(2) 0.0677(16) Uani 1 1 d . . .
H29 H 0.0262 0.5869 0.6273 0.081 Uiso 1 1 calc R . .
C52 C 0.1498(7) 0.4650(3) 0.8784(2) 0.0631(15) Uani 1 1 d . . .
C30 C 0.4186(7) 0.7689(3) 0.6186(2) 0.0811(19) Uani 1 1 d D . .
H30 H 0.4761 0.7430 0.5972 0.097 Uiso 1 1 calc R . .
C70 C -0.1624(6) 0.6722(3) 0.9916(2) 0.0674(16) Uani 1 1 d . . .
H70 H -0.1312 0.6455 1.0140 0.081 Uiso 1 1 calc R . .
C17 C 0.6302(6) 0.5152(3) 0.6070(2) 0.0658(16) Uani 1 1 d . . .
H17 H 0.6035 0.5221 0.6404 0.079 Uiso 1 1 calc R . .
C51 C -0.1757(9) 0.5664(3) 0.8540(2) 0.083(2) Uani 1 1 d . . .
H51 H -0.2135 0.5775 0.8858 0.099 Uiso 1 1 calc R . .
C2 C 0.3528(7) 0.5186(3) 0.7034(2) 0.0718(17) Uani 1 1 d . . .
H2 H 0.4041 0.5382 0.7247 0.086 Uiso 1 1 calc R . .
C27 C -0.0307(8) 0.6507(4) 0.5269(3) 0.086(2) Uani 1 1 d . . .
H27 H -0.0898 0.6484 0.5036 0.104 Uiso 1 1 calc R . .
C66 C -0.1620(6) 0.7036(3) 0.9092(2) 0.0651(16) Uani 1 1 d . . .
H66 H -0.1308 0.6988 0.8759 0.078 Uiso 1 1 calc R . .
C4 C 0.2106(7) 0.4346(3) 0.6840(2) 0.0683(17) Uani 1 1 d . . .
C23 C 0.4587(7) 0.6493(3) 0.7232(2) 0.0682(16) Uani 1 1 d . . .
H23 H 0.3670 0.6400 0.7369 0.082 Uiso 1 1 calc R . .
C48 C -0.0689(12) 0.5329(3) 0.7629(2) 0.102(3) Uani 1 1 d . . .
H48 H -0.0323 0.5212 0.7311 0.123 Uiso 1 1 calc R . .
C14 C 0.7058(8) 0.4923(4) 0.5087(3) 0.095(2) Uani 1 1 d . . .
H14 H 0.7301 0.4838 0.4754 0.113 Uiso 1 1 calc R . .
C47 C 0.0252(9) 0.5579(3) 0.7925(2) 0.095(2) Uani 1 1 d . . .
H47 H 0.1202 0.5626 0.7811 0.113 Uiso 1 1 calc R . .
C67 C -0.2544(7) 0.7514(3) 0.9257(3) 0.085(2) Uani 1 1 d . . .
H67 H -0.2868 0.7782 0.9036 0.101 Uiso 1 1 calc R . .
C57 C 0.0264(8) 0.4425(3) 0.9037(3) 0.085(2) Uani 1 1 d . . .
H57 H -0.0351 0.4702 0.9219 0.102 Uiso 1 1 calc R . .
C53 C 0.2380(8) 0.4234(3) 0.8514(3) 0.088(2) Uani 1 1 d . . .
H53 H 0.3220 0.4372 0.8336 0.106 Uiso 1 1 calc R . .
C28 C -0.0471(7) 0.6101(3) 0.5655(3) 0.084(2) Uani 1 1 d . . .
H28 H -0.1168 0.5799 0.5683 0.101 Uiso 1 1 calc R . .
C6 C 0.1172(7) 0.4399(3) 0.6090(3) 0.0831(19) Uani 1 1 d . . .
H6 H 0.1089 0.4599 0.5798 0.100 Uiso 1 1 calc R . .
C68 C -0.2974(7) 0.7588(3) 0.9754(3) 0.087(2) Uani 1 1 d . . .
H68 H -0.3584 0.7911 0.9865 0.104 Uiso 1 1 calc R . .
C25 C 0.1625(6) 0.6981(3) 0.5571(2) 0.0670(16) Uani 1 1 d . . .
H25 H 0.2335 0.7277 0.5538 0.080 Uiso 1 1 calc R . .
C8 C 0.0574(7) 0.3551(3) 0.6664(3) 0.087(2) Uani 1 1 d . . .
H8 H 0.0072 0.3187 0.6752 0.104 Uiso 1 1 calc R . .
C16 C 0.7242(7) 0.4689(3) 0.5915(3) 0.087(2) Uani 1 1 d . . .
H16 H 0.7638 0.4456 0.6141 0.104 Uiso 1 1 calc R . .
C69 C -0.2523(8) 0.7194(4) 1.0085(3) 0.085(2) Uani 1 1 d . . .
H69 H -0.2821 0.7247 1.0419 0.102 Uiso 1 1 calc R . .
C3 C 0.2919(8) 0.4630(3) 0.7152(2) 0.084(2) Uani 1 1 d . . .
H3 H 0.3040 0.4433 0.7442 0.101 Uiso 1 1 calc R . .
C59 C 0.4100(8) 0.5958(3) 0.9233(3) 0.086(2) Uani 1 1 d . . .
H59 H 0.4397 0.6138 0.8929 0.103 Uiso 1 1 calc R . .
C63 C 0.2537(7) 0.5282(3) 0.9748(2) 0.0746(17) Uani 1 1 d . . .
H63 H 0.1776 0.5012 0.9791 0.089 Uiso 1 1 calc R . .
C26 C 0.0732(8) 0.6950(4) 0.5227(2) 0.082(2) Uani 1 1 d . . .
H26 H 0.0837 0.7230 0.4966 0.099 Uiso 1 1 calc R . .
C32 C 0.2149(7) 0.7837(3) 0.6785(2) 0.083(2) Uani 1 1 d D . .
H32 H 0.1357 0.7678 0.6980 0.100 Uiso 1 1 calc R . .
C56 C -0.0093(9) 0.3803(4) 0.9031(3) 0.100(2) Uani 1 1 d . . .
H56 H -0.0929 0.3664 0.9210 0.120 Uiso 1 1 calc R . .
C33 C 0.2469(10) 0.8466(3) 0.6808(3) 0.113(3) Uani 1 1 d D . .
H33 H 0.1881 0.8730 0.7014 0.135 Uiso 1 1 calc R . .
C54 C 0.2016(11) 0.3602(4) 0.8506(3) 0.108(3) Uani 1 1 d . . .
H54 H 0.2622 0.3321 0.8324 0.130 Uiso 1 1 calc R . .
C7 C 0.0456(8) 0.3849(3) 0.6214(3) 0.100(2) Uani 1 1 d . . .
H7 H -0.0097 0.3674 0.6003 0.119 Uiso 1 1 calc R . .
C55 C 0.0787(11) 0.3394(4) 0.8760(4) 0.105(3) Uani 1 1 d . . .
H55 H 0.0548 0.2974 0.8750 0.126 Uiso 1 1 calc R . .
C49 C -0.2065(11) 0.5249(4) 0.7776(4) 0.107(3) Uani 1 1 d . . .
C35 C 0.4520(9) 0.8317(3) 0.6217(3) 0.102(2) Uani 1 1 d D . .
H35 H 0.5322 0.8478 0.6029 0.123 Uiso 1 1 calc R . .
C60 C 0.4802(9) 0.6075(4) 0.9610(4) 0.112(3) Uani 1 1 d . . .
H60 H 0.5565 0.6344 0.9566 0.135 Uiso 1 1 calc R . .
C15 C 0.7602(8) 0.4568(4) 0.5421(4) 0.105(3) Uani 1 1 d . . .
H15 H 0.8215 0.4243 0.5316 0.126 Uiso 1 1 calc R . .
C9 C 0.1364(9) 0.3778(3) 0.6952(3) 0.100(2) Uani 1 1 d . . .
H9 H 0.1452 0.3566 0.7239 0.119 Uiso 1 1 calc R . .
C62 C 0.3259(8) 0.5395(4) 1.0128(3) 0.101(3) Uani 1 1 d . . .
H62 H 0.2987 0.5203 1.0429 0.121 Uiso 1 1 calc R . .
C61 C 0.4386(10) 0.5795(5) 1.0060(4) 0.118(3) Uani 1 1 d . . .
H61 H 0.4869 0.5877 1.0318 0.142 Uiso 1 1 calc R . .
C34 C 0.3648(10) 0.8699(4) 0.6529(3) 0.113(3) Uani 1 1 d D . .
H34 H 0.3864 0.9120 0.6550 0.136 Uiso 1 1 calc R . .
N2 N 0.1878(6) 0.6884(2) 0.8963(2) 0.0766(15) Uani 1 1 d D . .
C36 C 0.1330(7) 0.6629(3) 0.8603(2) 0.0676(17) Uani 1 1 d D . .
C44 C 0.2692(7) 0.7414(3) 0.8855(3) 0.082(2) Uani 1 1 d D . .
C39 C 0.2952(8) 0.7689(3) 0.8405(3) 0.090(2) Uani 1 1 d D . .
C37 C 0.1481(7) 0.6889(3) 0.8135(2) 0.084(2) Uani 1 1 d D . .
H37 H 0.1043 0.6712 0.7892 0.100 Uiso 1 1 calc R . .
C38 C 0.2301(8) 0.7417(3) 0.8041(3) 0.100(3) Uani 1 1 d D . .
H38 H 0.2421 0.7595 0.7731 0.120 Uiso 1 1 calc R . .
C43 C 0.3347(8) 0.7670(4) 0.9214(3) 0.113(3) Uani 1 1 d D . .
H43 H 0.3258 0.7512 0.9531 0.136 Uiso 1 1 calc R . .
C42 C 0.4167(9) 0.8194(4) 0.9051(5) 0.288(12) Uani 1 1 d D . .
H42 H 0.4528 0.8407 0.9296 0.346 Uiso 1 1 calc R . .
C41 C 0.4529(10) 0.8449(4) 0.8586(5) 0.200(8) Uani 1 1 d D . .
H41 H 0.5217 0.8751 0.8509 0.241 Uiso 1 1 calc R . .
C40 C 0.3811(10) 0.8222(4) 0.8273(3) 0.123(3) Uani 1 1 d D . .
H40 H 0.3852 0.8404 0.7965 0.147 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.470(4) . ?
P1 C31 1.805(6) . ?
P1 C24 1.817(6) . ?
P1 C10 1.910(5) . ?
P2 O3 1.472(4) . ?
P2 C52 1.803(6) . ?
P2 C58 1.809(6) . ?
P2 C45 1.918(6) . ?
Cl2 C49 1.744(9) . ?
Cl1 C21 1.756(7) . ?
N1 C1 1.314(6) . ?
N1 C5 1.364(7) . ?
O4 C64 1.211(6) . ?
C1 C2 1.404(7) . ?
C1 C10 1.538(7) . ?
O2 C11 1.215(6) . ?
C18 C19 1.364(8) . ?
C18 C23 1.389(7) . ?
C18 C10 1.559(7) . ?
C10 C11 1.535(7) . ?
C11 C12 1.491(7) . ?
C65 C70 1.381(7) . ?
C65 C66 1.381(8) . ?
C65 C64 1.495(8) . ?
C5 C6 1.375(8) . ?
C5 C4 1.408(8) . ?
C12 C17 1.392(7) . ?
C12 C13 1.394(7) . ?
C45 C36 1.527(8) . ?
C45 C64 1.538(7) . ?
C45 C46 1.554(9) . ?
C24 C25 1.381(7) . ?
C24 C29 1.383(8) . ?
C13 C14 1.372(9) . ?
C22 C21 1.361(9) . ?
C22 C23 1.407(8) . ?
C19 C20 1.395(8) . ?
C58 C63 1.381(8) . ?
C58 C59 1.384(9) . ?
C20 C21 1.366(9) . ?
C46 C51 1.346(9) . ?
C46 C47 1.435(9) . ?
C50 C49 1.400(11) . ?
C50 C51 1.438(10) . ?
C31 C32 1.380(6) . ?
C31 C30 1.389(7) . ?
C29 C28 1.384(9) . ?
C52 C53 1.372(8) . ?
C52 C57 1.372(9) . ?
C30 C35 1.388(7) . ?
C70 C69 1.366(9) . ?
C17 C16 1.368(8) . ?
C2 C3 1.346(8) . ?
C27 C28 1.367(10) . ?
C27 C26 1.375(9) . ?
C66 C67 1.389(8) . ?
C4 C3 1.396(9) . ?
C4 C9 1.422(9) . ?
C48 C49 1.341(11) . ?
C48 C47 1.423(10) . ?
C14 C15 1.367(10) . ?
C67 C68 1.379(9) . ?
C57 C56 1.376(9) . ?
C53 C54 1.400(10) . ?
C6 C7 1.383(9) . ?
C68 C69 1.367(10) . ?
C25 C26 1.388(8) . ?
C8 C9 1.285(10) . ?
C8 C7 1.420(10) . ?
C16 C15 1.379(10) . ?
C59 C60 1.357(10) . ?
C63 C62 1.374(9) . ?
C32 C33 1.386(7) . ?
C56 C55 1.361(11) . ?
C33 C34 1.368(8) . ?
C54 C55 1.359(11) . ?
C35 C34 1.378(8) . ?
C60 C61 1.382(12) . ?
C62 C61 1.377(12) . ?
N2 C36 1.318(7) . ?
N2 C44 1.387(8) . ?
C36 C37 1.397(6) . ?
C44 C39 1.362(9) . ?
C44 C43 1.375(7) . ?
C39 C38 1.398(7) . ?
C39 C40 1.427(8) . ?
C37 C38 1.382(7) . ?
C43 C42 1.409(8) . ?
C42 C41 1.390(9) . ?
C41 C40 1.289(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C31 110.7(2) . . ?
O1 P1 C24 110.1(3) . . ?
C31 P1 C24 105.8(2) . . ?
O1 P1 C10 107.7(2) . . ?
C31 P1 C10 109.3(2) . . ?
C24 P1 C10 113.3(2) . . ?
O3 P2 C52 110.0(3) . . ?
O3 P2 C58 110.5(3) . . ?
C52 P2 C58 107.9(3) . . ?
O3 P2 C45 107.5(2) . . ?
C52 P2 C45 110.2(3) . . ?
C58 P2 C45 110.8(3) . . ?
C1 N1 C5 118.7(5) . . ?
N1 C1 C2 122.4(5) . . ?
N1 C1 C10 113.7(4) . . ?
C2 C1 C10 124.0(5) . . ?
C19 C18 C23 118.4(5) . . ?
C19 C18 C10 122.1(5) . . ?
C23 C18 C10 119.5(5) . . ?
C11 C10 C1 108.8(4) . . ?
C11 C10 C18 109.9(4) . . ?
C1 C10 C18 115.6(4) . . ?
C11 C10 P1 111.9(3) . . ?
C1 C10 P1 103.3(3) . . ?
C18 C10 P1 107.2(3) . . ?
O2 C11 C12 120.3(5) . . ?
O2 C11 C10 119.3(5) . . ?
C12 C11 C10 120.3(4) . . ?
C70 C65 C66 118.7(6) . . ?
C70 C65 C64 117.2(5) . . ?
C66 C65 C64 124.0(5) . . ?
N1 C5 C6 119.2(6) . . ?
N1 C5 C4 122.0(6) . . ?
C6 C5 C4 118.8(6) . . ?
C17 C12 C13 118.4(5) . . ?
C17 C12 C11 123.1(5) . . ?
C13 C12 C11 118.5(5) . . ?
C36 C45 C64 110.1(4) . . ?
C36 C45 C46 115.7(5) . . ?
C64 C45 C46 109.3(5) . . ?
C36 C45 P2 102.9(4) . . ?
C64 C45 P2 110.1(4) . . ?
C46 C45 P2 108.5(4) . . ?
C25 C24 C29 118.7(6) . . ?
C25 C24 P1 123.5(5) . . ?
C29 C24 P1 117.4(4) . . ?
C14 C13 C12 120.2(7) . . ?
C21 C22 C23 119.5(6) . . ?
O4 C64 C65 118.8(5) . . ?
O4 C64 C45 119.6(5) . . ?
C65 C64 C45 121.5(5) . . ?
C18 C19 C20 122.7(6) . . ?
C63 C58 C59 119.9(6) . . ?
C63 C58 P2 124.4(5) . . ?
C59 C58 P2 115.6(5) . . ?
C21 C20 C19 117.6(6) . . ?
C51 C46 C47 117.7(7) . . ?
C51 C46 C45 124.1(6) . . ?
C47 C46 C45 118.2(7) . . ?
C49 C50 C51 112.1(8) . . ?
C22 C21 C20 122.0(6) . . ?
C22 C21 Cl1 118.8(6) . . ?
C20 C21 Cl1 119.1(6) . . ?
C32 C31 C30 119.1(6) . . ?
C32 C31 P1 115.1(5) . . ?
C30 C31 P1 125.7(4) . . ?
C24 C29 C28 120.7(6) . . ?
C53 C52 C57 117.8(6) . . ?
C53 C52 P2 115.0(6) . . ?
C57 C52 P2 127.2(5) . . ?
C35 C30 C31 120.6(7) . . ?
C69 C70 C65 121.9(6) . . ?
C16 C17 C12 120.8(6) . . ?
C46 C51 C50 128.0(7) . . ?
C3 C2 C1 119.4(6) . . ?
C28 C27 C26 119.9(7) . . ?
C65 C66 C67 120.1(6) . . ?
C3 C4 C5 117.2(6) . . ?
C3 C4 C9 123.6(6) . . ?
C5 C4 C9 119.1(7) . . ?
C18 C23 C22 119.7(6) . . ?
C49 C48 C47 124.9(8) . . ?
C15 C14 C13 120.5(7) . . ?
C48 C47 C46 115.1(8) . . ?
C68 C67 C66 119.3(7) . . ?
C52 C57 C56 122.2(7) . . ?
C52 C53 C54 120.0(8) . . ?
C27 C28 C29 120.2(7) . . ?
C5 C6 C7 120.4(7) . . ?
C69 C68 C67 121.2(7) . . ?
C24 C25 C26 120.4(6) . . ?
C9 C8 C7 120.9(7) . . ?
C17 C16 C15 119.9(7) . . ?
C70 C69 C68 118.8(6) . . ?
C2 C3 C4 120.3(6) . . ?
C60 C59 C58 120.0(7) . . ?
C62 C63 C58 119.9(7) . . ?
C27 C26 C25 120.1(6) . . ?
C31 C32 C33 120.3(7) . . ?
C55 C56 C57 119.5(8) . . ?
C34 C33 C32 120.0(8) . . ?
C55 C54 C53 120.7(8) . . ?
C6 C7 C8 119.4(7) . . ?
C54 C55 C56 119.7(8) . . ?
C48 C49 C50 122.2(8) . . ?
C48 C49 Cl2 120.8(8) . . ?
C50 C49 Cl2 116.9(8) . . ?
C34 C35 C30 119.2(7) . . ?
C59 C60 C61 120.2(8) . . ?
C14 C15 C16 120.1(7) . . ?
C8 C9 C4 121.3(7) . . ?
C63 C62 C61 119.7(8) . . ?
C62 C61 C60 120.2(8) . . ?
C33 C34 C35 120.8(7) . . ?
C36 N2 C44 117.4(6) . . ?
N2 C36 C37 122.7(6) . . ?
N2 C36 C45 111.6(5) . . ?
C37 C36 C45 125.7(6) . . ?
C39 C44 C43 116.7(8) . . ?
C39 C44 N2 124.4(7) . . ?
C43 C44 N2 118.8(7) . . ?
C44 C39 C38 116.1(7) . . ?
C44 C39 C40 126.5(8) . . ?
C38 C39 C40 117.4(7) . . ?
C38 C37 C36 118.1(7) . . ?
C37 C38 C39 121.2(6) . . ?
C44 C43 C42 112.8(9) . . ?
C41 C42 C43 131.0(9) . . ?
C40 C41 C42 113.0(8) . . ?
C41 C40 C39 118.9(9) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.059
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_compound31
_database_code_depnum_ccdc_archive 'CCDC 1447744'
_audit_update_record             
;
2016-01-16 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H22 Cl N O3 S'
_chemical_formula_sum            'C30 H22 Cl N O3 S'
_chemical_formula_weight         512.01

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.626(2)
_cell_length_b                   11.358(2)
_cell_length_c                   21.635(4)
_cell_angle_alpha                104.76(3)
_cell_angle_beta                 91.46(3)
_cell_angle_gamma                90.01(3)
_cell_volume                     2524.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2493
_cell_measurement_theta_min      0.524
_cell_measurement_theta_max      26.240

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064.0
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  multi-scan
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6447
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         26.24
_reflns_number_total             5334
_reflns_number_gt                4844
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1795P)²+1.1292P] 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         5334
_refine_ls_number_parameters     651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0836
_refine_ls_wR_factor_ref         0.2541
_refine_ls_wR_factor_gt          0.2468
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.013
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.31289(10) 0.72750(10) 0.18002(5) 0.0440(3) Uani 1 1 d . . .
S1 S 0.81319(10) 0.77261(10) 0.32011(5) 0.0435(3) Uani 1 1 d . . .
Cl2 Cl 0.55353(17) 1.22504(14) 0.26114(8) 0.0762(5) Uani 1 1 d . . .
Cl1 Cl 0.05381(17) 0.27471(15) 0.23862(8) 0.0763(5) Uani 1 1 d . . .
O1 O 0.9460(3) 0.7973(4) 0.3242(2) 0.0606(9) Uani 1 1 d . . .
N1 N 0.7197(3) 0.5568(3) 0.41957(19) 0.0443(9) Uani 1 1 d . . .
C41 C 0.2503(4) 0.7462(4) 0.10115(19) 0.0378(9) Uani 1 1 d . . .
O6 O 0.3603(3) 0.5598(3) 0.05793(18) 0.0570(10) Uani 1 1 d . . .
O5 O 0.4461(3) 0.7040(4) 0.17516(18) 0.0600(10) Uani 1 1 d . . .
C24 C 0.5470(4) 0.8715(4) 0.4192(2) 0.0426(10) Uani 1 1 d . . .
H24 H 0.5938 0.9377 0.4429 0.051 Uiso 1 1 calc R . .
C12 C 0.8028(3) 0.8572(4) 0.4536(2) 0.0369(9) Uani 1 1 d . . .
O3 O 0.8600(4) 0.9408(3) 0.44220(17) 0.0571(9) Uani 1 1 d . . .
C49 C 0.1076(4) 0.7374(4) 0.10740(19) 0.0372(9) Uani 1 1 d . . .
O4 O 0.2696(4) 0.8340(3) 0.22596(17) 0.0615(10) Uani 1 1 d . . .
O2 O 0.7692(4) 0.6658(3) 0.27406(17) 0.0602(9) Uani 1 1 d . . .
N2 N 0.2191(4) 0.9438(3) 0.08006(19) 0.0448(9) Uani 1 1 d . . .
C10 C 0.8001(4) 0.6309(4) 0.4061(2) 0.0378(9) Uani 1 1 d . . .
C9 C 0.7619(5) 0.4508(4) 0.4315(2) 0.0505(12) Uani 1 1 d . . .
C1 C 0.9318(4) 0.6089(4) 0.4012(2) 0.0467(11) Uani 1 1 d . . .
H1 H 0.9858 0.6665 0.3923 0.056 Uiso 1 1 calc R . .
C25 C 0.7371(4) 0.9030(4) 0.3048(2) 0.0425(9) Uani 1 1 d . . .
C31 C 0.4313(4) 0.8917(4) 0.0983(2) 0.0451(10) Uani 1 1 d . . .
H31 H 0.4864 0.8335 0.1065 0.054 Uiso 1 1 calc R . .
C13 C 0.7805(3) 0.8524(4) 0.5213(2) 0.0387(9) Uani 1 1 d . . .
C19 C 0.6069(4) 0.7623(4) 0.39277(19) 0.0369(9) Uani 1 1 d . . .
C42 C 0.3018(4) 0.6440(4) 0.0467(2) 0.0389(9) Uani 1 1 d . . .
C40 C 0.3004(4) 0.8683(4) 0.0948(2) 0.0390(9) Uani 1 1 d . . .
C60 C 0.2998(4) 0.4864(5) 0.1805(2) 0.0517(11) Uani 1 1 d . . .
H60 H 0.3778 0.4785 0.1614 0.062 Uiso 1 1 calc R . .
C18 C 0.6920(4) 0.7810(4) 0.5399(2) 0.0462(10) Uani 1 1 d . . .
H18 H 0.6452 0.7256 0.5087 0.055 Uiso 1 1 calc R . .
C30 C 0.7996(5) 1.0122(5) 0.3188(2) 0.0503(11) Uani 1 1 d . . .
H30 H 0.8800 1.0189 0.3374 0.060 Uiso 1 1 calc R . .
C56 C 0.1223(5) 0.6108(5) 0.2246(2) 0.0526(12) Uani 1 1 d . . .
H56 H 0.0834 0.6864 0.2352 0.063 Uiso 1 1 calc R . .
C20 C 0.5365(4) 0.6658(4) 0.3567(2) 0.0451(10) Uani 1 1 d . . .
H20 H 0.5749 0.5923 0.3379 0.054 Uiso 1 1 calc R . .
C11 C 0.7495(4) 0.7540(4) 0.3979(2) 0.0360(9) Uani 1 1 d . . .
C55 C 0.2381(4) 0.5989(4) 0.1952(2) 0.0445(10) Uani 1 1 d . . .
C54 C 0.0470(4) 0.6279(4) 0.0802(2) 0.0433(10) Uani 1 1 d . . .
H54 H 0.0917 0.5628 0.0558 0.052 Uiso 1 1 calc R . .
C28 C 0.6265(5) 1.0977(5) 0.2770(2) 0.0512(11) Uani 1 1 d . . .
C21 C 0.4083(5) 0.6798(5) 0.3488(3) 0.0562(13) Uani 1 1 d . . .
H21 H 0.3607 0.6145 0.3248 0.067 Uiso 1 1 calc R . .
C2 C 0.9779(5) 0.5006(4) 0.4099(2) 0.0501(12) Uani 1 1 d . . .
C8 C 0.6754(7) 0.3757(5) 0.4500(3) 0.0684(17) Uani 1 1 d . . .
H8 H 0.5907 0.3964 0.4520 0.082 Uiso 1 1 calc R . .
C39 C 0.2634(5) 1.0478(4) 0.0686(2) 0.0479(10) Uani 1 1 d . . .
C5 C 0.9280(7) 0.3093(5) 0.4413(3) 0.072(2) Uani 1 1 d . . .
H5 H 1.0119 0.2858 0.4383 0.087 Uiso 1 1 calc R . .
C27 C 0.5647(5) 0.9893(5) 0.2623(2) 0.0536(12) Uani 1 1 d . . .
H27 H 0.4847 0.9828 0.2433 0.064 Uiso 1 1 calc R . .
C14 C 0.8516(4) 0.9345(4) 0.5679(2) 0.0468(10) Uani 1 1 d . . .
H14 H 0.9123 0.9833 0.5563 0.056 Uiso 1 1 calc R . .
C50 C 0.0366(4) 0.8337(4) 0.1435(2) 0.0454(10) Uani 1 1 d . . .
H50 H 0.0760 0.9078 0.1624 0.055 Uiso 1 1 calc R . .
C4 C 0.8929(5) 0.4196(4) 0.4261(2) 0.0512(13) Uani 1 1 d . . .
C26 C 0.6209(5) 0.8880(5) 0.2758(2) 0.0480(11) Uani 1 1 d . . .
H26 H 0.5806 0.8126 0.2653 0.058 Uiso 1 1 calc R . .
C57 C 0.0647(5) 0.5130(5) 0.2382(2) 0.0550(12) Uani 1 1 d . . .
H57 H -0.0130 0.5203 0.2576 0.066 Uiso 1 1 calc R . .
C38 C 0.1753(7) 1.1253(5) 0.0488(3) 0.0678(16) Uani 1 1 d . . .
H38 H 0.0901 1.1052 0.0455 0.081 Uiso 1 1 calc R . .
C58 C 0.1269(5) 0.4021(5) 0.2219(2) 0.0541(12) Uani 1 1 d . . .
C51 C -0.0927(5) 0.8204(5) 0.1517(3) 0.0579(13) Uani 1 1 d . . .
H51 H -0.1387 0.8854 0.1753 0.069 Uiso 1 1 calc R . .
C15 C 0.8304(5) 0.9424(5) 0.6321(2) 0.0574(14) Uani 1 1 d . . .
H15 H 0.8779 0.9966 0.6635 0.069 Uiso 1 1 calc R . .
C44 C 0.1897(4) 0.7203(4) -0.0393(2) 0.0447(10) Uani 1 1 d . . .
H44 H 0.1423 0.7738 -0.0091 0.054 Uiso 1 1 calc R . .
C23 C 0.4178(5) 0.8831(5) 0.4109(3) 0.0553(13) Uani 1 1 d . . .
H23 H 0.3784 0.9562 0.4296 0.066 Uiso 1 1 calc R . .
C32 C 0.4782(5) 0.9978(5) 0.0899(2) 0.0487(11) Uani 1 1 d . . .
C48 C 0.3506(4) 0.5659(4) -0.0673(2) 0.0473(10) Uani 1 1 d . . .
H48 H 0.4108 0.5172 -0.0543 0.057 Uiso 1 1 calc R . .
C6 C 0.8461(8) 0.2400(5) 0.4591(3) 0.084(2) Uani 1 1 d . . .
H6 H 0.8729 0.1682 0.4683 0.101 Uiso 1 1 calc R . .
C59 C 0.2433(5) 0.3882(5) 0.1948(3) 0.0582(13) Uani 1 1 d . . .
H59 H 0.2833 0.3132 0.1862 0.070 Uiso 1 1 calc R . .
C43 C 0.2817(4) 0.6467(4) -0.0214(2) 0.0388(9) Uani 1 1 d . . .
C17 C 0.6700(5) 0.7893(5) 0.6047(3) 0.0591(13) Uani 1 1 d . . .
H17 H 0.6098 0.7406 0.6167 0.071 Uiso 1 1 calc R . .
C53 C -0.0818(5) 0.6156(5) 0.0895(3) 0.0568(13) Uani 1 1 d . . .
H53 H -0.1221 0.5417 0.0715 0.068 Uiso 1 1 calc R . .
C45 C 0.1723(5) 0.7095(5) -0.1043(3) 0.0581(13) Uani 1 1 d . . .
H45 H 0.1121 0.7577 -0.1178 0.070 Uiso 1 1 calc R . .
C29 C 0.7435(5) 1.1123(5) 0.3052(3) 0.0563(12) Uani 1 1 d . . .
H29 H 0.7842 1.1875 0.3151 0.068 Uiso 1 1 calc R . .
C7 C 0.7137(8) 0.2722(6) 0.4650(3) 0.083(2) Uani 1 1 d . . .
H7 H 0.6565 0.2230 0.4788 0.100 Uiso 1 1 calc R . .
C3 C 1.1175(5) 0.4754(6) 0.4030(3) 0.0702(17) Uani 1 1 d . . .
H3A H 1.1613 0.5492 0.4027 0.105 Uiso 1 1 calc R . .
H3B H 1.1314 0.4154 0.3636 0.105 Uiso 1 1 calc R . .
H3C H 1.1484 0.4457 0.4382 0.105 Uiso 1 1 calc R . .
C37 C 0.2148(9) 1.2295(6) 0.0343(4) 0.085(2) Uani 1 1 d . . .
H37 H 0.1560 1.2802 0.0219 0.102 Uiso 1 1 calc R . .
C35 C 0.4307(7) 1.1901(5) 0.0581(3) 0.0695(16) Uani 1 1 d . . .
H35 H 0.5151 1.2131 0.0622 0.083 Uiso 1 1 calc R . .
C22 C 0.3496(4) 0.7881(6) 0.3755(3) 0.0654(15) Uani 1 1 d . . .
H22 H 0.2634 0.7959 0.3693 0.078 Uiso 1 1 calc R . .
C36 C 0.3446(9) 1.2614(6) 0.0381(4) 0.085(2) Uani 1 1 d . . .
H36 H 0.3705 1.3311 0.0267 0.102 Uiso 1 1 calc R . .
C34 C 0.3931(5) 1.0808(4) 0.0729(2) 0.0511(11) Uani 1 1 d . . .
C47 C 0.3319(5) 0.5564(6) -0.1311(3) 0.0582(13) Uani 1 1 d . . .
H47 H 0.3786 0.5021 -0.1614 0.070 Uiso 1 1 calc R . .
C46 C 0.2413(6) 0.6298(6) -0.1498(3) 0.0662(15) Uani 1 1 d . . .
H46 H 0.2271 0.6252 -0.1930 0.079 Uiso 1 1 calc R . .
C33 C 0.6181(5) 1.0223(6) 0.0953(3) 0.0683(16) Uani 1 1 d . . .
H33A H 0.6611 0.9528 0.1029 0.102 Uiso 1 1 calc R . .
H33B H 0.6359 1.0921 0.1301 0.102 Uiso 1 1 calc R . .
H33C H 0.6464 1.0374 0.0562 0.102 Uiso 1 1 calc R . .
C16 C 0.7409(5) 0.8718(6) 0.6495(2) 0.0673(16) Uani 1 1 d . . .
H16 H 0.7276 0.8797 0.6927 0.081 Uiso 1 1 calc R . .
C52 C -0.1502(4) 0.7124(6) 0.1252(3) 0.0622(14) Uani 1 1 d . . .
H52 H -0.2357 0.7029 0.1308 0.075 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
S2 O4 1.439(4) . ?
S2 O5 1.442(4) . ?
S2 C55 1.769(5) . ?
S2 C41 1.878(4) . ?
S1 O2 1.430(4) . ?
S1 O1 1.435(4) . ?
S1 C25 1.786(4) . ?
S1 C11 1.891(5) . ?
Cl2 C28 1.746(5) . ?
Cl1 C58 1.763(5) . ?
N1 C10 1.288(6) . ?
N1 C9 1.368(5) . ?
C41 C40 1.525(6) . ?
C41 C49 1.531(5) . ?
C41 C42 1.539(6) . ?
O6 C42 1.212(5) . ?
C24 C19 1.388(6) . ?
C24 C23 1.391(6) . ?
C12 O3 1.208(6) . ?
C12 C13 1.503(6) . ?
C12 C11 1.548(5) . ?
C49 C54 1.384(5) . ?
C49 C50 1.404(6) . ?
N2 C40 1.307(6) . ?
N2 C39 1.354(6) . ?
C10 C1 1.424(6) . ?
C10 C11 1.549(5) . ?
C9 C8 1.387(9) . ?
C9 C4 1.436(8) . ?
C1 C2 1.378(6) . ?
C25 C26 1.362(7) . ?
C25 C30 1.367(7) . ?
C31 C32 1.360(7) . ?
C31 C40 1.413(6) . ?
C13 C18 1.374(7) . ?
C13 C14 1.393(5) . ?
C19 C20 1.380(6) . ?
C19 C11 1.521(5) . ?
C42 C43 1.494(6) . ?
C60 C59 1.373(8) . ?
C60 C55 1.403(6) . ?
C18 C17 1.405(7) . ?
C30 C29 1.376(7) . ?
C56 C57 1.368(7) . ?
C56 C55 1.390(7) . ?
C20 C21 1.383(7) . ?
C54 C53 1.401(7) . ?
C28 C27 1.356(7) . ?
C28 C29 1.362(8) . ?
C21 C22 1.376(8) . ?
C2 C4 1.403(8) . ?
C2 C3 1.516(7) . ?
C8 C7 1.357(8) . ?
C39 C38 1.417(7) . ?
C39 C34 1.423(8) . ?
C5 C6 1.303(12) . ?
C5 C4 1.421(6) . ?
C27 C26 1.388(7) . ?
C14 C15 1.393(7) . ?
C50 C51 1.403(7) . ?
C57 C58 1.390(7) . ?
C38 C37 1.368(10) . ?
C58 C59 1.374(8) . ?
C51 C52 1.353(8) . ?
C15 C16 1.364(9) . ?
C44 C45 1.389(7) . ?
C44 C43 1.396(6) . ?
C23 C22 1.351(8) . ?
C32 C34 1.415(8) . ?
C32 C33 1.508(7) . ?
C48 C47 1.366(8) . ?
C48 C43 1.392(7) . ?
C6 C7 1.454(12) . ?
C17 C16 1.374(8) . ?
C53 C52 1.388(8) . ?
C45 C46 1.381(9) . ?
C37 C36 1.421(12) . ?
C35 C36 1.356(10) . ?
C35 C34 1.418(8) . ?
C47 C46 1.393(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S2 O5 119.3(2) . . ?
O4 S2 C55 107.9(2) . . ?
O5 S2 C55 108.3(2) . . ?
O4 S2 C41 104.2(2) . . ?
O5 S2 C41 108.7(2) . . ?
C55 S2 C41 107.92(18) . . ?
O2 S1 O1 117.7(3) . . ?
O2 S1 C25 109.2(2) . . ?
O1 S1 C25 107.0(2) . . ?
O2 S1 C11 103.6(2) . . ?
O1 S1 C11 112.6(2) . . ?
C25 S1 C11 106.3(2) . . ?
C10 N1 C9 118.9(4) . . ?
C40 C41 C49 115.9(3) . . ?
C40 C41 C42 109.0(4) . . ?
C49 C41 C42 112.7(3) . . ?
C40 C41 S2 106.4(2) . . ?
C49 C41 S2 102.9(3) . . ?
C42 C41 S2 109.4(3) . . ?
C19 C24 C23 120.8(4) . . ?
O3 C12 C13 121.2(4) . . ?
O3 C12 C11 119.7(4) . . ?
C13 C12 C11 119.1(4) . . ?
C54 C49 C50 118.3(4) . . ?
C54 C49 C41 119.0(4) . . ?
C50 C49 C41 122.5(4) . . ?
C40 N2 C39 118.1(4) . . ?
N1 C10 C1 124.3(4) . . ?
N1 C10 C11 117.1(4) . . ?
C1 C10 C11 118.5(4) . . ?
N1 C9 C8 118.3(5) . . ?
N1 C9 C4 120.7(5) . . ?
C8 C9 C4 121.1(4) . . ?
C2 C1 C10 118.8(5) . . ?
C26 C25 C30 122.0(4) . . ?
C26 C25 S1 118.3(4) . . ?
C30 C25 S1 119.5(3) . . ?
C32 C31 C40 121.1(4) . . ?
C18 C13 C14 119.1(4) . . ?
C18 C13 C12 125.7(4) . . ?
C14 C13 C12 115.1(4) . . ?
C20 C19 C24 118.9(4) . . ?
C20 C19 C11 120.7(4) . . ?
C24 C19 C11 120.1(4) . . ?
O6 C42 C43 118.2(4) . . ?
O6 C42 C41 121.2(4) . . ?
C43 C42 C41 120.6(3) . . ?
N2 C40 C31 122.1(4) . . ?
N2 C40 C41 117.4(3) . . ?
C31 C40 C41 120.2(4) . . ?
C59 C60 C55 119.0(5) . . ?
C13 C18 C17 122.0(4) . . ?
C25 C30 C29 120.0(4) . . ?
C57 C56 C55 121.0(5) . . ?
C19 C20 C21 119.2(4) . . ?
C19 C11 C12 110.6(3) . . ?
C19 C11 C10 115.2(3) . . ?
C12 C11 C10 108.6(3) . . ?
C19 C11 S1 106.9(3) . . ?
C12 C11 S1 109.1(3) . . ?
C10 C11 S1 106.2(3) . . ?
C56 C55 C60 120.3(5) . . ?
C56 C55 S2 120.2(4) . . ?
C60 C55 S2 119.4(4) . . ?
C49 C54 C53 119.7(5) . . ?
C27 C28 C29 122.4(4) . . ?
C27 C28 Cl2 119.5(4) . . ?
C29 C28 Cl2 118.1(4) . . ?
C22 C21 C20 121.5(4) . . ?
C1 C2 C4 118.1(4) . . ?
C1 C2 C3 119.0(5) . . ?
C4 C2 C3 122.9(4) . . ?
C7 C8 C9 120.4(7) . . ?
N2 C39 C38 117.6(5) . . ?
N2 C39 C34 123.8(4) . . ?
C38 C39 C34 118.5(5) . . ?
C6 C5 C4 122.0(7) . . ?
C28 C27 C26 120.0(4) . . ?
C15 C14 C13 119.0(5) . . ?
C51 C50 C49 121.2(5) . . ?
C2 C4 C5 124.4(5) . . ?
C2 C4 C9 119.2(4) . . ?
C5 C4 C9 116.4(6) . . ?
C25 C26 C27 117.7(5) . . ?
C56 C57 C58 117.4(5) . . ?
C37 C38 C39 120.4(6) . . ?
C59 C58 C57 123.1(5) . . ?
C59 C58 Cl1 118.8(4) . . ?
C57 C58 Cl1 118.1(4) . . ?
C52 C51 C50 119.6(5) . . ?
C16 C15 C14 120.9(4) . . ?
C45 C44 C43 116.7(5) . . ?
C22 C23 C24 119.9(5) . . ?
C31 C32 C34 118.2(4) . . ?
C31 C32 C33 120.4(5) . . ?
C34 C32 C33 121.4(5) . . ?
C47 C48 C43 121.5(5) . . ?
C5 C6 C7 121.6(5) . . ?
C60 C59 C58 119.2(5) . . ?
C48 C43 C44 120.8(4) . . ?
C48 C43 C42 117.7(4) . . ?
C44 C43 C42 121.3(4) . . ?
C16 C17 C18 117.5(6) . . ?
C52 C53 C54 120.9(5) . . ?
C46 C45 C44 122.4(5) . . ?
C28 C29 C30 117.9(5) . . ?
C8 C7 C6 118.5(8) . . ?
C38 C37 C36 120.9(6) . . ?
C36 C35 C34 120.6(6) . . ?
C23 C22 C21 119.7(4) . . ?
C35 C36 C37 120.0(6) . . ?
C32 C34 C35 123.8(5) . . ?
C32 C34 C39 116.5(4) . . ?
C35 C34 C39 119.6(5) . . ?
C48 C47 C46 118.4(5) . . ?
C45 C46 C47 120.1(5) . . ?
C15 C16 C17 121.4(5) . . ?
C51 C52 C53 120.2(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.24
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.104
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Compound33
_database_code_depnum_ccdc_archive 'CCDC 1447745'
_audit_update_record             
;
2016-01-16 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H32 N O6 P S'
_chemical_formula_sum            'C29 H32 N O6 P S'
_chemical_formula_weight         553.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   34.280(3)
_cell_length_b                   17.6184(13)
_cell_length_c                   25.486(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 131.387(3)
_cell_angle_gamma                90.00
_cell_volume                     11548(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    1458
_cell_measurement_theta_min      3.7510
_cell_measurement_theta_max      28.0760

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4672.0
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.76412
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlisPro, Oxford Diffraction Ltd.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         'not applicable'
_diffrn_standards_interval_count 'not applicable'
_diffrn_standards_interval_time  'not applicable'
_diffrn_standards_decay_%        none
_diffrn_reflns_number            19581
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0635
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             10156
_reflns_number_gt                5811
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0755P)²+13.3311P] 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     SHELXL
_refine_ls_extinction_coef       0.0025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9448
_refine_ls_number_parameters     696
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1801
_refine_ls_wR_factor_gt          0.1583
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
P2 P 0.82509(4) 0.51275(5) 0.39161(5) 0.0453(3) Uani 1 1 d . . .
S2 S 0.71740(5) 0.45392(6) 0.45399(6) 0.0564(3) Uani 1 1 d . . .
P1 P 0.67913(5) 0.76432(5) 0.25672(6) 0.0527(3) Uani 1 1 d . . .
S1 S 0.52402(6) 0.70173(7) 0.01210(9) 0.0873(4) Uani 1 1 d . . .
O8 O 0.79604(11) 0.54797(12) 0.31736(13) 0.0493(6) Uani 1 1 d . . .
O3 O 0.72757(11) 0.79860(13) 0.27100(14) 0.0527(7) Uani 1 1 d . . .
O9 O 0.87757(11) 0.55751(13) 0.44226(14) 0.0536(7) Uani 1 1 d . . .
O11 O 0.76941(13) 0.42685(16) 0.49642(15) 0.0724(9) Uani 1 1 d . . .
O7 O 0.83336(12) 0.43161(13) 0.39119(15) 0.0592(7) Uani 1 1 d . . .
O1 O 0.68685(13) 0.68398(13) 0.27419(16) 0.0657(8) Uani 1 1 d . . .
N2 N 0.71084(14) 0.51897(16) 0.40054(16) 0.0473(8) Uani 1 1 d . . .
O2 O 0.67319(14) 0.81114(15) 0.30331(17) 0.0704(9) Uani 1 1 d . . .
O12 O 0.69893(15) 0.48858(16) 0.48450(17) 0.0774(10) Uani 1 1 d . . .
N1 N 0.57248(15) 0.76294(18) 0.0444(2) 0.0654(10) Uani 1 1 d . . .
C30 C 0.73948(16) 0.50620(18) 0.37772(19) 0.0434(9) Uani 1 1 d . . .
O4 O 0.52507(17) 0.6837(2) 0.0676(3) 0.1041(13) Uani 1 1 d . . .
C48 C 0.81177(17) 0.58288(19) 0.4791(2) 0.0481(9) Uani 1 1 d . . .
C47 C 0.78713(16) 0.53504(18) 0.41578(18) 0.0434(9) Uani 1 1 d . . .
C33 C 0.63248(17) 0.53802(19) 0.2776(2) 0.0490(9) Uani 1 1 d . . .
C31 C 0.70926(16) 0.46152(19) 0.31194(19) 0.0470(9) Uani 1 1 d . . .
H31A H 0.7053 0.4102 0.3215 0.056 Uiso 1 1 calc R . .
H31B H 0.7291 0.4587 0.2972 0.056 Uiso 1 1 calc R . .
C32 C 0.65513(17) 0.49364(19) 0.2514(2) 0.0489(9) Uani 1 1 d . . .
C34 C 0.65987(17) 0.55138(19) 0.3479(2) 0.0492(9) Uani 1 1 d . . .
C18 C 0.62258(17) 0.7846(2) 0.1667(2) 0.0537(10) Uani 1 1 d . . .
C1 C 0.61937(16) 0.7526(2) 0.1161(2) 0.0525(10) Uani 1 1 d . . .
C2 C 0.65909(16) 0.70700(19) 0.1226(2) 0.0505(9) Uani 1 1 d . . .
H2A H 0.6461 0.6557 0.1065 0.061 Uiso 1 1 calc R . .
H2B H 0.6904 0.7042 0.1716 0.061 Uiso 1 1 calc R . .
C40 C 0.67436(19) 0.3801(2) 0.4003(2) 0.0556(11) Uani 1 1 d . . .
C54 C 0.79767(17) 0.6296(2) 0.3122(2) 0.0589(11) Uani 1 1 d . . .
H54A H 0.7804 0.6537 0.3263 0.071 Uiso 1 1 calc R . .
H54B H 0.7791 0.6434 0.2640 0.071 Uiso 1 1 calc R . .
C53 C 0.85593(19) 0.5599(2) 0.5443(2) 0.0625(11) Uani 1 1 d . . .
H53 H 0.8710 0.5134 0.5494 0.075 Uiso 1 1 calc R . .
C4 C 0.6268(2) 0.7802(2) 0.0145(2) 0.0590(11) Uani 1 1 d . . .
C19 C 0.58036(19) 0.8331(2) 0.1511(3) 0.0628(11) Uani 1 1 d . . .
C49 C 0.7900(2) 0.6532(2) 0.4726(3) 0.0648(12) Uani 1 1 d . . .
H49 H 0.7599 0.6694 0.4289 0.078 Uiso 1 1 calc R . .
C35 C 0.6400(2) 0.5991(2) 0.3689(2) 0.0619(12) Uani 1 1 d . . .
H35 H 0.6594 0.6088 0.4162 0.074 Uiso 1 1 calc R . .
C3 C 0.67287(18) 0.7397(2) 0.0809(2) 0.0540(10) Uani 1 1 d . . .
C56 C 0.85274(18) 0.6580(2) 0.3577(2) 0.0593(11) Uani 1 1 d . . .
C5 C 0.5807(2) 0.7920(2) -0.0012(2) 0.0639(12) Uani 1 1 d . . .
C38 C 0.58435(19) 0.5733(2) 0.2298(2) 0.0631(11) Uani 1 1 d . . .
H38 H 0.5653 0.5657 0.1823 0.076 Uiso 1 1 calc R . .
C55 C 0.88025(18) 0.6386(2) 0.4331(2) 0.0622(11) Uani 1 1 d . . .
H55A H 0.9164 0.6539 0.4628 0.075 Uiso 1 1 calc R . .
H55B H 0.8644 0.6668 0.4475 0.075 Uiso 1 1 calc R . .
C41 C 0.6918(2) 0.3169(2) 0.3897(3) 0.0713(13) Uani 1 1 d . . .
H41 H 0.7269 0.3114 0.4132 0.086 Uiso 1 1 calc R . .
C26 C 0.7360(2) 0.8802(2) 0.2794(2) 0.0655(12) Uani 1 1 d . . .
H26A H 0.7085 0.9053 0.2355 0.079 Uiso 1 1 calc R . .
H26B H 0.7688 0.8919 0.2914 0.079 Uiso 1 1 calc R . .
O5 O 0.47885(18) 0.7338(2) -0.0513(3) 0.1394(18) Uani 1 1 d . . .
C27 C 0.7370(2) 0.9097(2) 0.3364(2) 0.0699(14) Uani 1 1 d . . .
C36 C 0.5922(2) 0.6318(2) 0.3204(3) 0.0729(13) Uani 1 1 d . . .
H36 H 0.5788 0.6627 0.3347 0.087 Uiso 1 1 calc R . .
C10 C 0.6951(2) 0.6769(2) 0.0663(3) 0.0779(15) Uani 1 1 d . . .
H10A H 0.7069 0.6981 0.0442 0.117 Uiso 1 1 calc R . .
H10B H 0.6686 0.6398 0.0359 0.117 Uiso 1 1 calc R . .
H10C H 0.7237 0.6532 0.1095 0.117 Uiso 1 1 calc R . .
C37 C 0.5639(2) 0.6187(3) 0.2500(3) 0.0720(13) Uani 1 1 d . . .
H37 H 0.5312 0.6405 0.2167 0.086 Uiso 1 1 calc R . .
C45 C 0.6226(2) 0.3873(3) 0.3662(3) 0.0764(14) Uani 1 1 d . . .
H45 H 0.6111 0.4294 0.3745 0.092 Uiso 1 1 calc R . .
C39 C 0.6193(2) 0.4299(2) 0.2026(2) 0.0684(12) Uani 1 1 d . . .
H39A H 0.5862 0.4506 0.1631 0.103 Uiso 1 1 calc R . .
H39B H 0.6146 0.3952 0.2270 0.103 Uiso 1 1 calc R . .
H39C H 0.6344 0.4036 0.1868 0.103 Uiso 1 1 calc R . .
C9 C 0.6342(3) 0.8131(2) -0.0284(3) 0.0804(15) Uani 1 1 d . . .
H9D H 0.6654 0.8059 -0.0185 0.097 Uiso 1 1 calc R . .
C16 C 0.5611(2) 0.5591(3) 0.0364(3) 0.0775(14) Uani 1 1 d . . .
H16 H 0.5694 0.5638 0.0792 0.093 Uiso 1 1 calc R . .
C25 C 0.6854(3) 0.8922(2) 0.3148(3) 0.0818(17) Uani 1 1 d . . .
H25A H 0.6853 0.9100 0.3508 0.098 Uiso 1 1 calc R . .
H25B H 0.6584 0.9196 0.2721 0.098 Uiso 1 1 calc R . .
C51 C 0.8567(3) 0.6743(3) 0.5948(3) 0.0890(18) Uani 1 1 d . . .
H51 H 0.8719 0.7050 0.6338 0.107 Uiso 1 1 calc R . .
C29 C 0.7808(3) 0.8743(3) 0.4062(2) 0.096(2) Uani 1 1 d . . .
H29A H 0.7807 0.8940 0.4412 0.144 Uiso 1 1 calc R . .
H29B H 0.8134 0.8861 0.4186 0.144 Uiso 1 1 calc R . .
H29C H 0.7763 0.8202 0.4031 0.144 Uiso 1 1 calc R . .
C52 C 0.8782(2) 0.6051(3) 0.6022(2) 0.0804(15) Uani 1 1 d . . .
H52 H 0.9077 0.5886 0.6462 0.097 Uiso 1 1 calc R . .
C20 C 0.5654(2) 0.8989(2) 0.1117(3) 0.0731(13) Uani 1 1 d . . .
H20 H 0.5826 0.9137 0.0966 0.088 Uiso 1 1 calc R . .
C42 C 0.6563(3) 0.2611(3) 0.3434(3) 0.0829(16) Uani 1 1 d . . .
H42 H 0.6681 0.2176 0.3370 0.099 Uiso 1 1 calc R . .
C57 C 0.8807(2) 0.6244(3) 0.3359(3) 0.0772(14) Uani 1 1 d . . .
H57A H 0.8822 0.5702 0.3409 0.116 Uiso 1 1 calc R . .
H57B H 0.9153 0.6445 0.3649 0.116 Uiso 1 1 calc R . .
H57C H 0.8622 0.6370 0.2879 0.116 Uiso 1 1 calc R . .
C50 C 0.8126(3) 0.6986(3) 0.5299(3) 0.0850(17) Uani 1 1 d . . .
H50 H 0.7983 0.7457 0.5250 0.102 Uiso 1 1 calc R . .
C43 C 0.6044(3) 0.2694(3) 0.3071(3) 0.0869(17) Uani 1 1 d . . .
C7 C 0.5503(3) 0.8688(3) -0.0996(3) 0.105(2) Uani 1 1 d . . .
H7 H 0.5248 0.8988 -0.1378 0.126 Uiso 1 1 calc R . .
C8 C 0.5955(3) 0.8559(3) -0.0852(3) 0.095(2) Uani 1 1 d . . .
H8 H 0.6004 0.8763 -0.1142 0.114 Uiso 1 1 calc R . .
C6 C 0.5416(2) 0.8378(3) -0.0580(3) 0.0888(17) Uani 1 1 d . . .
H6 H 0.5108 0.8470 -0.0674 0.107 Uiso 1 1 calc R . .
C24 C 0.5559(2) 0.8134(3) 0.1757(3) 0.0863(16) Uani 1 1 d . . .
H24 H 0.5663 0.7702 0.2032 0.104 Uiso 1 1 calc R . .
C11 C 0.53846(19) 0.6185(3) -0.0096(2) 0.0686(12) Uani 1 1 d . . .
C58 C 0.8504(2) 0.7452(2) 0.3513(4) 0.0995(19) Uani 1 1 d . . .
H58A H 0.8326 0.7592 0.3038 0.149 Uiso 1 1 calc R . .
H58B H 0.8851 0.7654 0.3815 0.149 Uiso 1 1 calc R . .
H58C H 0.8321 0.7655 0.3647 0.149 Uiso 1 1 calc R . .
C15 C 0.5716(3) 0.4918(3) 0.0196(3) 0.0889(16) Uani 1 1 d . . .
H15 H 0.5872 0.4521 0.0517 0.107 Uiso 1 1 calc R . .
C44 C 0.5876(2) 0.3323(3) 0.3195(3) 0.0886(16) Uani 1 1 d . . .
H44 H 0.5525 0.3378 0.2962 0.106 Uiso 1 1 calc R . .
C14 C 0.5596(2) 0.4827(4) -0.0421(4) 0.0939(18) Uani 1 1 d . . .
C12 C 0.5262(3) 0.6102(4) -0.0724(3) 0.102(2) Uani 1 1 d . . .
H12 H 0.5105 0.6497 -0.1047 0.122 Uiso 1 1 calc R . .
C28 C 0.7439(3) 0.9957(2) 0.3404(3) 0.104(2) Uani 1 1 d . . .
H28A H 0.7173 1.0174 0.2950 0.157 Uiso 1 1 calc R . .
H28B H 0.7774 1.0076 0.3557 0.157 Uiso 1 1 calc R . .
H28C H 0.7413 1.0163 0.3729 0.157 Uiso 1 1 calc R . .
C13 C 0.5376(3) 0.5415(5) -0.0877(3) 0.110(2) Uani 1 1 d . . .
H13 H 0.5300 0.5363 -0.1300 0.133 Uiso 1 1 calc R . .
C21 C 0.5247(3) 0.9426(3) 0.0947(3) 0.0964(18) Uani 1 1 d . . .
H21 H 0.5136 0.9854 0.0666 0.116 Uiso 1 1 calc R . .
C22 C 0.5009(3) 0.9222(3) 0.1197(4) 0.109(2) Uani 1 1 d . . .
H22 H 0.4744 0.9524 0.1096 0.131 Uiso 1 1 calc R . .
C46 C 0.5656(3) 0.2100(4) 0.2533(3) 0.127(3) Uani 1 1 d . . .
H46A H 0.5540 0.2230 0.2084 0.190 Uiso 1 1 calc R . .
H46B H 0.5363 0.2085 0.2506 0.190 Uiso 1 1 calc R . .
H46C H 0.5820 0.1611 0.2672 0.190 Uiso 1 1 calc R . .
C23 C 0.5157(3) 0.8578(3) 0.1594(4) 0.112(2) Uani 1 1 d . . .
H23 H 0.4988 0.8440 0.1753 0.134 Uiso 1 1 calc R . .
C17 C 0.5697(3) 0.4085(4) -0.0606(4) 0.142(3) Uani 1 1 d . . .
H17A H 0.5423 0.3734 -0.0770 0.213 Uiso 1 1 calc R . .
H17B H 0.6023 0.3880 -0.0199 0.213 Uiso 1 1 calc R . .
H17C H 0.5711 0.4168 -0.0966 0.213 Uiso 1 1 calc R . .
O10 O 0.65859(13) 0.54342(14) 0.21026(14) 0.0617(8) Uani 1 1 d . . .
H10 H 0.6660 0.5863 0.2269 0.092 Uiso 1 1 calc R . .
O6 O 0.71393(12) 0.79422(14) 0.12259(16) 0.0623(8) Uani 1 1 d . . .
H6A H 0.7028 0.8323 0.1274 0.094 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
P2 O7 1.459(2) . ?
P2 O9 1.567(3) . ?
P2 O8 1.570(3) . ?
P2 C47 1.813(4) . ?
S2 O11 1.424(3) . ?
S2 O12 1.425(3) . ?
S2 N2 1.678(3) . ?
S2 C40 1.752(4) . ?
P1 O1 1.455(3) . ?
P1 O2 1.566(3) . ?
P1 O3 1.567(3) . ?
P1 C18 1.808(4) . ?
S1 O5 1.421(5) . ?
S1 O4 1.427(4) . ?
S1 N1 1.671(4) . ?
S1 C11 1.750(5) . ?
O8 C54 1.449(4) . ?
O3 C26 1.454(4) . ?
O9 C55 1.460(4) . ?
N2 C34 1.442(5) . ?
N2 C30 1.452(5) . ?
O2 C25 1.463(5) . ?
N1 C1 1.440(5) . ?
N1 C5 1.457(6) . ?
C30 C47 1.331(5) . ?
C30 C31 1.486(5) . ?
C48 C53 1.375(6) . ?
C48 C49 1.399(5) . ?
C48 C47 1.492(5) . ?
C33 C34 1.388(5) . ?
C33 C38 1.391(6) . ?
C33 C32 1.532(5) . ?
C31 C32 1.536(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 O10 1.430(4) . ?
C32 C39 1.515(5) . ?
C34 C35 1.391(5) . ?
C18 C1 1.343(5) . ?
C18 C19 1.491(6) . ?
C1 C2 1.494(5) . ?
C2 C3 1.533(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C40 C45 1.370(7) . ?
C40 C41 1.371(6) . ?
C54 C56 1.505(6) . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C53 C52 1.381(6) . ?
C53 H53 0.9300 . ?
C4 C5 1.368(7) . ?
C4 C9 1.399(6) . ?
C4 C3 1.527(6) . ?
C19 C24 1.384(6) . ?
C19 C20 1.392(6) . ?
C49 C50 1.370(6) . ?
C49 H49 0.9300 . ?
C35 C36 1.367(7) . ?
C35 H35 0.9300 . ?
C3 O6 1.433(5) . ?
C3 C10 1.521(5) . ?
C56 C57 1.510(6) . ?
C56 C55 1.517(6) . ?
C56 C58 1.542(5) . ?
C5 C6 1.405(7) . ?
C38 C37 1.369(6) . ?
C38 H38 0.9300 . ?
C55 H55A 0.9700 . ?
C55 H55B 0.9700 . ?
C41 C42 1.394(7) . ?
C41 H41 0.9300 . ?
C26 C27 1.523(6) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C25 1.499(8) . ?
C27 C29 1.508(7) . ?
C27 C28 1.527(5) . ?
C36 C37 1.381(7) . ?
C36 H36 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C37 H37 0.9300 . ?
C45 C44 1.380(7) . ?
C45 H45 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C9 C8 1.373(8) . ?
C9 H9D 0.9300 . ?
C16 C11 1.368(6) . ?
C16 C15 1.385(6) . ?
C16 H16 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C51 C52 1.372(8) . ?
C51 C50 1.378(8) . ?
C51 H51 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C52 H52 0.9300 . ?
C20 C21 1.388(7) . ?
C20 H20 0.9300 . ?
C42 C43 1.367(8) . ?
C42 H42 0.9300 . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C50 H50 0.9300 . ?
C43 C44 1.378(8) . ?
C43 C46 1.528(7) . ?
C7 C8 1.354(9) . ?
C7 C6 1.390(8) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C6 H6 0.9300 . ?
C24 C23 1.388(8) . ?
C24 H24 0.9300 . ?
C11 C12 1.369(7) . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C15 C14 1.348(8) . ?
C15 H15 0.9300 . ?
C44 H44 0.9300 . ?
C14 C13 1.354(9) . ?
C14 C17 1.506(8) . ?
C12 C13 1.404(9) . ?
C12 H12 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C13 H13 0.9300 . ?
C21 C22 1.373(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.376(8) . ?
C22 H22 0.9300 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C23 H23 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
O10 H10 0.8200 . ?
O6 H6A 0.8200 . ?

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
O7 P2 O9 112.11(16) . . ?
O7 P2 O8 110.48(15) . . ?
O9 P2 O8 105.18(14) . . ?
O7 P2 C47 113.67(15) . . ?
O9 P2 C47 107.60(16) . . ?
O8 P2 C47 107.34(16) . . ?
O11 S2 O12 121.0(2) . . ?
O11 S2 N2 105.88(17) . . ?
O12 S2 N2 106.33(16) . . ?
O11 S2 C40 109.2(2) . . ?
O12 S2 C40 107.2(2) . . ?
N2 S2 C40 106.37(17) . . ?
O1 P1 O2 111.67(16) . . ?
O1 P1 O3 110.70(17) . . ?
O2 P1 O3 105.66(15) . . ?
O1 P1 C18 113.96(18) . . ?
O2 P1 C18 106.88(18) . . ?
O3 P1 C18 107.53(16) . . ?
O5 S1 O4 120.7(3) . . ?
O5 S1 N1 106.5(2) . . ?
O4 S1 N1 106.8(2) . . ?
O5 S1 C11 107.3(3) . . ?
O4 S1 C11 107.5(2) . . ?
N1 S1 C11 107.4(2) . . ?
C54 O8 P2 118.0(2) . . ?
C26 O3 P1 119.5(3) . . ?
C55 O9 P2 121.3(2) . . ?
C34 N2 C30 114.4(3) . . ?
C34 N2 S2 117.1(2) . . ?
C30 N2 S2 117.2(2) . . ?
C25 O2 P1 120.3(3) . . ?
C1 N1 C5 114.5(3) . . ?
C1 N1 S1 117.1(3) . . ?
C5 N1 S1 119.1(3) . . ?
C47 C30 N2 118.5(3) . . ?
C47 C30 C31 129.0(3) . . ?
N2 C30 C31 112.5(3) . . ?
C53 C48 C49 118.7(4) . . ?
C53 C48 C47 121.6(3) . . ?
C49 C48 C47 119.7(4) . . ?
C30 C47 C48 123.3(3) . . ?
C30 C47 P2 118.7(3) . . ?
C48 C47 P2 118.0(3) . . ?
C34 C33 C38 116.9(4) . . ?
C34 C33 C32 123.0(4) . . ?
C38 C33 C32 119.8(3) . . ?
C30 C31 C32 114.6(3) . . ?
C30 C31 H31A 108.6 . . ?
C32 C31 H31A 108.6 . . ?
C30 C31 H31B 108.6 . . ?
C32 C31 H31B 108.6 . . ?
H31A C31 H31B 107.6 . . ?
O10 C32 C39 105.6(3) . . ?
O10 C32 C33 108.5(3) . . ?
C39 C32 C33 111.5(4) . . ?
O10 C32 C31 109.4(3) . . ?
C39 C32 C31 109.7(3) . . ?
C33 C32 C31 112.0(3) . . ?
C33 C34 C35 120.9(4) . . ?
C33 C34 N2 120.2(3) . . ?
C35 C34 N2 118.8(3) . . ?
C1 C18 C19 122.4(4) . . ?
C1 C18 P1 118.3(3) . . ?
C19 C18 P1 119.3(3) . . ?
C18 C1 N1 118.7(4) . . ?
C18 C1 C2 129.0(4) . . ?
N1 C1 C2 112.3(3) . . ?
C1 C2 C3 113.4(3) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C45 C40 C41 119.9(4) . . ?
C45 C40 S2 119.7(3) . . ?
C41 C40 S2 120.3(4) . . ?
O8 C54 C56 111.3(3) . . ?
O8 C54 H54A 109.4 . . ?
C56 C54 H54A 109.4 . . ?
O8 C54 H54B 109.4 . . ?
C56 C54 H54B 109.4 . . ?
H54A C54 H54B 108.0 . . ?
C48 C53 C52 120.7(4) . . ?
C48 C53 H53 119.7 . . ?
C52 C53 H53 119.7 . . ?
C5 C4 C9 118.7(4) . . ?
C5 C4 C3 122.9(4) . . ?
C9 C4 C3 118.1(4) . . ?
C24 C19 C20 119.4(4) . . ?
C24 C19 C18 120.6(4) . . ?
C20 C19 C18 120.0(4) . . ?
C50 C49 C48 120.5(5) . . ?
C50 C49 H49 119.7 . . ?
C48 C49 H49 119.7 . . ?
C36 C35 C34 120.4(4) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
O6 C3 C10 105.3(4) . . ?
O6 C3 C4 107.3(3) . . ?
C10 C3 C4 112.7(3) . . ?
O6 C3 C2 109.8(3) . . ?
C10 C3 C2 109.2(3) . . ?
C4 C3 C2 112.2(4) . . ?
C54 C56 C57 111.3(4) . . ?
C54 C56 C55 108.3(3) . . ?
C57 C56 C55 111.3(4) . . ?
C54 C56 C58 107.3(4) . . ?
C57 C56 C58 110.7(4) . . ?
C55 C56 C58 107.7(4) . . ?
C4 C5 C6 121.2(5) . . ?
C4 C5 N1 120.6(4) . . ?
C6 C5 N1 117.9(5) . . ?
C37 C38 C33 122.5(4) . . ?
C37 C38 H38 118.7 . . ?
C33 C38 H38 118.7 . . ?
O9 C55 C56 111.8(3) . . ?
O9 C55 H55A 109.3 . . ?
C56 C55 H55A 109.3 . . ?
O9 C55 H55B 109.3 . . ?
C56 C55 H55B 109.3 . . ?
H55A C55 H55B 107.9 . . ?
C40 C41 C42 119.4(5) . . ?
C40 C41 H41 120.3 . . ?
C42 C41 H41 120.3 . . ?
O3 C26 C27 110.7(3) . . ?
O3 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
O3 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C25 C27 C29 111.2(4) . . ?
C25 C27 C26 107.7(4) . . ?
C29 C27 C26 111.2(4) . . ?
C25 C27 C28 108.7(5) . . ?
C29 C27 C28 110.1(4) . . ?
C26 C27 C28 107.9(4) . . ?
C35 C36 C37 119.8(4) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C38 C37 C36 119.4(5) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C40 C45 C44 120.3(5) . . ?
C40 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C32 C39 H39A 109.5 . . ?
C32 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C32 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C8 C9 C4 120.2(6) . . ?
C8 C9 H9D 119.9 . . ?
C4 C9 H9D 119.9 . . ?
C11 C16 C15 120.5(4) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
O2 C25 C27 112.6(4) . . ?
O2 C25 H25A 109.1 . . ?
C27 C25 H25A 109.1 . . ?
O2 C25 H25B 109.1 . . ?
C27 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C52 C51 C50 120.2(5) . . ?
C52 C51 H51 119.9 . . ?
C50 C51 H51 119.9 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C51 C52 C53 120.0(5) . . ?
C51 C52 H52 120.0 . . ?
C53 C52 H52 120.0 . . ?
C21 C20 C19 120.1(5) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C43 C42 C41 120.9(5) . . ?
C43 C42 H42 119.6 . . ?
C41 C42 H42 119.6 . . ?
C56 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C56 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C49 C50 C51 119.9(5) . . ?
C49 C50 H50 120.0 . . ?
C51 C50 H50 120.0 . . ?
C42 C43 C44 119.0(5) . . ?
C42 C43 C46 120.4(6) . . ?
C44 C43 C46 120.6(7) . . ?
C8 C7 C6 120.7(5) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.9(6) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C7 C6 C5 118.2(6) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C19 C24 C23 120.2(5) . . ?
C19 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C16 C11 C12 118.8(5) . . ?
C16 C11 S1 119.3(3) . . ?
C12 C11 S1 121.9(5) . . ?
C56 C58 H58A 109.5 . . ?
C56 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C56 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C14 C15 C16 121.3(6) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C43 C44 C45 120.3(6) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 H44 119.8 . . ?
C15 C14 C13 118.6(6) . . ?
C15 C14 C17 120.8(7) . . ?
C13 C14 C17 120.6(6) . . ?
C11 C12 C13 119.3(6) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C14 C13 C12 121.4(5) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C22 C21 C20 119.5(5) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 121.0(5) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C22 C23 C24 119.6(5) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C32 O10 H10 109.5 . . ?
C3 O6 H6A 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.048

#===END_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
