# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_EB004
_database_code_depnum_ccdc_archive 'CCDC 1589387'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2018-04-05 downloaded from the CCDC.
;

#===========================================================================

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H31 N2 O P S2, C H2 Cl2'
_chemical_formula_sum            'C29 H33 Cl2 N2 O P S2'
_chemical_formula_weight         591.56

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   14.3251(3)
_cell_length_b                   13.4264(3)
_cell_length_c                   15.3146(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.1770(10)
_cell_angle_gamma                90
_cell_volume                     2907.82(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.56

_exptl_crystal_description       'thick plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.448
_shelx_estimated_absorpt_T_min   0.868
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6983
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51144
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.440
_diffrn_reflns_theta_max         28.967
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7287
_reflns_number_gt                5928
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+1.2792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7287
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.03795(3) 0.93669(3) 0.38750(3) 0.03756(11) Uani 1 1 d . . . . .
Cl2 Cl 0.04496(4) 0.74396(3) 0.44116(3) 0.03993(12) Uani 1 1 d . . . . .
S1 S 0.73863(3) 0.89381(3) 0.52098(3) 0.02369(9) Uani 1 1 d . . . . .
S2 S 0.74510(3) 0.65526(3) 0.44669(2) 0.02589(10) Uani 1 1 d . . . . .
P1 P 0.68356(3) 0.75882(3) 0.50779(2) 0.01782(9) Uani 1 1 d . . . . .
O1 O 0.27666(8) 0.78285(9) 0.34428(8) 0.0316(3) Uani 1 1 d . . . . .
N1 N 0.61062(9) 0.71662(9) 0.67257(8) 0.0191(3) Uani 1 1 d . . . . .
N2 N 0.75580(9) 0.67124(9) 0.67735(8) 0.0199(3) Uani 1 1 d . . . . .
C1 C 0.68154(10) 0.71294(10) 0.62361(9) 0.0181(3) Uani 1 1 d . . . . .
C2 C 0.64077(12) 0.67748(12) 0.75574(10) 0.0241(3) Uani 1 1 d . . . . .
H2 H 0.6043 0.6716 0.8021 0.029 Uiso 1 1 calc R U . . .
C3 C 0.73091(12) 0.64947(12) 0.75874(10) 0.0245(3) Uani 1 1 d . . . . .
H3 H 0.7704 0.6201 0.8077 0.029 Uiso 1 1 calc R U . . .
C4 C 0.51655(11) 0.75882(11) 0.65204(9) 0.0192(3) Uani 1 1 d . . . . .
C5 C 0.44138(11) 0.69573(11) 0.62097(10) 0.0220(3) Uani 1 1 d . . . . .
C6 C 0.35146(12) 0.73677(12) 0.60940(10) 0.0249(3) Uani 1 1 d . . . . .
H6 H 0.2989 0.6960 0.5869 0.030 Uiso 1 1 calc R U . . .
C7 C 0.33572(11) 0.83581(12) 0.62965(10) 0.0248(3) Uani 1 1 d . . . . .
C8 C 0.41334(11) 0.89570(11) 0.66049(10) 0.0229(3) Uani 1 1 d . . . . .
H8 H 0.4033 0.9638 0.6731 0.027 Uiso 1 1 calc R U . . .
C9 C 0.50517(11) 0.85856(11) 0.67341(9) 0.0204(3) Uani 1 1 d . . . . .
C10 C 0.45659(13) 0.58716(11) 0.60208(11) 0.0284(4) Uani 1 1 d . . . . .
H10A H 0.3954 0.5551 0.5824 0.043 Uiso 1 1 calc R U . . .
H10B H 0.4882 0.5544 0.6560 0.043 Uiso 1 1 calc R U . . .
H10C H 0.4961 0.5814 0.5556 0.043 Uiso 1 1 calc R U . . .
C11 C 0.23673(12) 0.87680(14) 0.62075(12) 0.0340(4) Uani 1 1 d . . . . .
H11A H 0.1942 0.8360 0.5787 0.051 Uiso 1 1 calc R U . . .
H11B H 0.2360 0.9456 0.5992 0.051 Uiso 1 1 calc R U . . .
H11C H 0.2156 0.8755 0.6785 0.051 Uiso 1 1 calc R U . . .
C12 C 0.58888(12) 0.92163(12) 0.70999(10) 0.0244(3) Uani 1 1 d . . . . .
H12A H 0.6167 0.8968 0.7685 0.037 Uiso 1 1 calc R U . . .
H12B H 0.5685 0.9908 0.7150 0.037 Uiso 1 1 calc R U . . .
H12C H 0.6361 0.9185 0.6703 0.037 Uiso 1 1 calc R U . . .
C13 C 0.85020(11) 0.64846(11) 0.65998(9) 0.0202(3) Uani 1 1 d . . . . .
C14 C 0.92093(11) 0.71956(11) 0.68087(10) 0.0231(3) Uani 1 1 d . . . . .
C15 C 1.01180(12) 0.69214(12) 0.66843(11) 0.0272(3) Uani 1 1 d . . . . .
H15 H 1.0615 0.7395 0.6805 0.033 Uiso 1 1 calc R U . . .
C16 C 1.03204(12) 0.59816(13) 0.63904(10) 0.0279(3) Uani 1 1 d . . . . .
C17 C 0.95946(12) 0.52844(12) 0.62322(10) 0.0262(3) Uani 1 1 d . . . . .
H17 H 0.9732 0.4634 0.6045 0.031 Uiso 1 1 calc R U . . .
C18 C 0.86736(11) 0.55132(11) 0.63401(10) 0.0219(3) Uani 1 1 d . . . . .
C19 C 0.90193(13) 0.81985(12) 0.71837(12) 0.0309(4) Uani 1 1 d . . . . .
H19A H 0.8568 0.8566 0.6753 0.046 Uiso 1 1 calc R U . . .
H19B H 0.9612 0.8574 0.7312 0.046 Uiso 1 1 calc R U . . .
H19C H 0.8755 0.8108 0.7730 0.046 Uiso 1 1 calc R U . . .
C20 C 1.13055(13) 0.56978(16) 0.62540(13) 0.0395(4) Uani 1 1 d . . . . .
H20A H 1.1475 0.5054 0.6536 0.059 Uiso 1 1 calc R U . . .
H20B H 1.1754 0.6207 0.6518 0.059 Uiso 1 1 calc R U . . .
H20C H 1.1327 0.5649 0.5619 0.059 Uiso 1 1 calc R U . . .
C21 C 0.79036(12) 0.47442(12) 0.61882(11) 0.0282(3) Uani 1 1 d . . . . .
H21A H 0.7605 0.4686 0.6719 0.042 Uiso 1 1 calc R U . . .
H21B H 0.8174 0.4100 0.6061 0.042 Uiso 1 1 calc R U . . .
H21C H 0.7429 0.4945 0.5686 0.042 Uiso 1 1 calc R U . . .
C22 C 0.55944(11) 0.76789(11) 0.46048(9) 0.0185(3) Uani 1 1 d . . . . .
C23 C 0.51243(11) 0.68721(11) 0.41470(10) 0.0229(3) Uani 1 1 d . . . . .
H23 H 0.5455 0.6266 0.4102 0.027 Uiso 1 1 calc R U . . .
C24 C 0.41889(11) 0.69469(12) 0.37619(10) 0.0253(3) Uani 1 1 d . . . . .
H24 H 0.3881 0.6395 0.3452 0.030 Uiso 1 1 calc R U . . .
C25 C 0.36938(11) 0.78297(12) 0.38264(10) 0.0232(3) Uani 1 1 d . . . . .
C26 C 0.41521(11) 0.86469(11) 0.42660(10) 0.0217(3) Uani 1 1 d . . . . .
H26 H 0.3821 0.9254 0.4307 0.026 Uiso 1 1 calc R U . . .
C27 C 0.50938(11) 0.85653(11) 0.46415(9) 0.0197(3) Uani 1 1 d . . . . .
H27 H 0.5407 0.9126 0.4931 0.024 Uiso 1 1 calc R U . . .
C28 C 0.22412(12) 0.87209(14) 0.35194(12) 0.0349(4) Uani 1 1 d . . . . .
H28A H 0.2241 0.8870 0.4146 0.052 Uiso 1 1 calc R U . . .
H28B H 0.1589 0.8631 0.3221 0.052 Uiso 1 1 calc R U . . .
H28C H 0.2533 0.9274 0.3244 0.052 Uiso 1 1 calc R U . . .
C29 C -0.03507(14) 0.83651(14) 0.46302(13) 0.0379(4) Uani 1 1 d . . . . .
H29A H -0.0162 0.8616 0.5241 0.045 Uiso 1 1 calc R U . . .
H29B H -0.0991 0.8073 0.4587 0.045 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C29 1.7701(19) . ?
Cl2 C29 1.7588(19) . ?
S1 P1 1.9741(5) . ?
S2 P1 1.9620(5) . ?
P1 C22 1.8139(15) . ?
P1 C1 1.8822(14) . ?
O1 C25 1.3639(19) . ?
O1 C28 1.430(2) . ?
N1 C1 1.3565(18) . ?
N1 C2 1.3818(18) . ?
N1 C4 1.4494(19) . ?
N2 C1 1.3577(18) . ?
N2 C3 1.3812(19) . ?
N2 C13 1.4517(19) . ?
C2 C3 1.339(2) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.393(2) . ?
C4 C9 1.394(2) . ?
C5 C6 1.386(2) . ?
C5 C10 1.509(2) . ?
C6 C7 1.392(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(2) . ?
C7 C11 1.507(2) . ?
C8 C9 1.391(2) . ?
C8 H8 0.9500 . ?
C9 C12 1.502(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.392(2) . ?
C13 C18 1.397(2) . ?
C14 C15 1.395(2) . ?
C14 C19 1.506(2) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(2) . ?
C16 C20 1.508(2) . ?
C17 C18 1.390(2) . ?
C17 H17 0.9500 . ?
C18 C21 1.502(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.395(2) . ?
C22 C23 1.403(2) . ?
C23 C24 1.379(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.395(2) . ?
C26 C27 1.384(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?

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
C22 P1 C1 103.71(6) . . ?
C22 P1 S2 110.09(5) . . ?
C1 P1 S2 107.04(5) . . ?
C22 P1 S1 109.24(5) . . ?
C1 P1 S1 105.66(5) . . ?
S2 P1 S1 119.79(3) . . ?
C25 O1 C28 116.93(13) . . ?
C1 N1 C2 110.12(12) . . ?
C1 N1 C4 130.30(12) . . ?
C2 N1 C4 119.46(12) . . ?
C1 N2 C3 110.13(13) . . ?
C1 N2 C13 129.68(12) . . ?
C3 N2 C13 120.19(12) . . ?
N1 C1 N2 105.27(12) . . ?
N1 C1 P1 129.38(11) . . ?
N2 C1 P1 125.31(11) . . ?
C3 C2 N1 107.25(13) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
C2 C3 N2 107.22(13) . . ?
C2 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
C5 C4 C9 123.46(14) . . ?
C5 C4 N1 118.54(13) . . ?
C9 C4 N1 117.64(13) . . ?
C6 C5 C4 117.00(14) . . ?
C6 C5 C10 121.28(14) . . ?
C4 C5 C10 121.72(14) . . ?
C5 C6 C7 122.10(15) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C8 118.58(15) . . ?
C6 C7 C11 120.81(15) . . ?
C8 C7 C11 120.59(15) . . ?
C9 C8 C7 121.81(14) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C4 117.01(14) . . ?
C8 C9 C12 122.12(13) . . ?
C4 C9 C12 120.86(14) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 123.45(14) . . ?
C14 C13 N2 118.60(13) . . ?
C18 C13 N2 117.41(13) . . ?
C13 C14 C15 116.66(14) . . ?
C13 C14 C19 122.13(14) . . ?
C15 C14 C19 121.17(15) . . ?
C16 C15 C14 122.20(15) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 C16 C17 118.68(15) . . ?
C15 C16 C20 121.60(16) . . ?
C17 C16 C20 119.71(16) . . ?
C18 C17 C16 121.85(15) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C13 116.99(14) . . ?
C17 C18 C21 121.15(14) . . ?
C13 C18 C21 121.86(14) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 118.03(14) . . ?
C27 C22 P1 121.24(11) . . ?
C23 C22 P1 120.64(11) . . ?
C24 C23 C22 120.92(14) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 120.18(14) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
O1 C25 C24 116.13(14) . . ?
O1 C25 C26 124.03(15) . . ?
C24 C25 C26 119.84(14) . . ?
C27 C26 C25 119.39(14) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C22 121.60(14) . . ?
C26 C27 H27 119.2 . . ?
C22 C27 H27 119.2 . . ?
O1 C28 H28A 109.5 . . ?
O1 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O1 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
Cl2 C29 Cl1 111.12(10) . . ?
Cl2 C29 H29A 109.4 . . ?
Cl1 C29 H29A 109.4 . . ?
Cl2 C29 H29B 109.4 . . ?
Cl1 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 -0.05(16) . . . . ?
C4 N1 C1 N2 175.89(13) . . . . ?
C2 N1 C1 P1 -177.78(11) . . . . ?
C4 N1 C1 P1 -1.8(2) . . . . ?
C3 N2 C1 N1 -0.04(16) . . . . ?
C13 N2 C1 N1 179.59(13) . . . . ?
C3 N2 C1 P1 177.80(11) . . . . ?
C13 N2 C1 P1 -2.6(2) . . . . ?
C22 P1 C1 N1 -20.17(15) . . . . ?
S2 P1 C1 N1 -136.57(12) . . . . ?
S1 P1 C1 N1 94.70(13) . . . . ?
C22 P1 C1 N2 162.52(12) . . . . ?
S2 P1 C1 N2 46.12(13) . . . . ?
S1 P1 C1 N2 -82.60(12) . . . . ?
C1 N1 C2 C3 0.13(18) . . . . ?
C4 N1 C2 C3 -176.31(13) . . . . ?
N1 C2 C3 N2 -0.15(18) . . . . ?
C1 N2 C3 C2 0.13(18) . . . . ?
C13 N2 C3 C2 -179.55(13) . . . . ?
C1 N1 C4 C5 97.40(18) . . . . ?
C2 N1 C4 C5 -86.97(17) . . . . ?
C1 N1 C4 C9 -89.20(18) . . . . ?
C2 N1 C4 C9 86.42(17) . . . . ?
C9 C4 C5 C6 1.5(2) . . . . ?
N1 C4 C5 C6 174.49(12) . . . . ?
C9 C4 C5 C10 -177.52(14) . . . . ?
N1 C4 C5 C10 -4.5(2) . . . . ?
C4 C5 C6 C7 -1.5(2) . . . . ?
C10 C5 C6 C7 177.52(14) . . . . ?
C5 C6 C7 C8 1.6(2) . . . . ?
C5 C6 C7 C11 -176.83(14) . . . . ?
C6 C7 C8 C9 -1.6(2) . . . . ?
C11 C7 C8 C9 176.84(14) . . . . ?
C7 C8 C9 C4 1.5(2) . . . . ?
C7 C8 C9 C12 -177.57(14) . . . . ?
C5 C4 C9 C8 -1.5(2) . . . . ?
N1 C4 C9 C8 -174.55(12) . . . . ?
C5 C4 C9 C12 177.58(13) . . . . ?
N1 C4 C9 C12 4.5(2) . . . . ?
C1 N2 C13 C14 91.88(18) . . . . ?
C3 N2 C13 C14 -88.52(17) . . . . ?
C1 N2 C13 C18 -96.31(18) . . . . ?
C3 N2 C13 C18 83.30(17) . . . . ?
C18 C13 C14 C15 4.7(2) . . . . ?
N2 C13 C14 C15 175.99(13) . . . . ?
C18 C13 C14 C19 -173.00(14) . . . . ?
N2 C13 C14 C19 -1.7(2) . . . . ?
C13 C14 C15 C16 -1.7(2) . . . . ?
C19 C14 C15 C16 176.04(15) . . . . ?
C14 C15 C16 C17 -1.3(2) . . . . ?
C14 C15 C16 C20 179.64(15) . . . . ?
C15 C16 C17 C18 1.6(2) . . . . ?
C20 C16 C17 C18 -179.36(15) . . . . ?
C16 C17 C18 C13 1.2(2) . . . . ?
C16 C17 C18 C21 -178.46(15) . . . . ?
C14 C13 C18 C17 -4.5(2) . . . . ?
N2 C13 C18 C17 -175.86(13) . . . . ?
C14 C13 C18 C21 175.17(14) . . . . ?
N2 C13 C18 C21 3.8(2) . . . . ?
C1 P1 C22 C27 92.28(12) . . . . ?
S2 P1 C22 C27 -153.49(10) . . . . ?
S1 P1 C22 C27 -20.03(13) . . . . ?
C1 P1 C22 C23 -91.30(12) . . . . ?
S2 P1 C22 C23 22.93(13) . . . . ?
S1 P1 C22 C23 156.39(11) . . . . ?
C27 C22 C23 C24 -1.4(2) . . . . ?
P1 C22 C23 C24 -177.93(11) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
C28 O1 C25 C24 178.64(14) . . . . ?
C28 O1 C25 C26 -1.3(2) . . . . ?
C23 C24 C25 O1 -178.56(14) . . . . ?
C23 C24 C25 C26 1.4(2) . . . . ?
O1 C25 C26 C27 179.26(14) . . . . ?
C24 C25 C26 C27 -0.7(2) . . . . ?
C25 C26 C27 C22 -1.1(2) . . . . ?
C23 C22 C27 C26 2.1(2) . . . . ?
P1 C22 C27 C26 178.63(11) . . . . ?

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_EB005
_database_code_depnum_ccdc_archive 'CCDC 1589388'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2018-04-05 downloaded from the CCDC.
;

#===========================================================================

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C34 H45 N2 O P S2), C7 H8'
_chemical_formula_sum            'C75 H98 N4 O2 P2 S4'
_chemical_formula_weight         1277.75

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+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                   34.664(5)
_cell_length_b                   13.266(2)
_cell_length_c                   15.692(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.515(2)
_cell_angle_gamma                90
_cell_volume                     6953.1(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    6212
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      26.60

_exptl_crystal_description       'long thin rod'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             2744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.575
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   0.879
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6896
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38530
_diffrn_reflns_av_unetI/netI     0.0904
_diffrn_reflns_av_R_equivalents  0.1101
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.219
_diffrn_reflns_theta_max         26.958
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7542
_reflns_number_gt                4663
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+2.5958P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7542
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.07307(2) 0.47241(5) 0.33204(4) 0.02374(17) Uani 1 1 d . . . . .
S2 S 0.17303(2) 0.42777(5) 0.36739(4) 0.02439(17) Uani 1 1 d . . . . .
P1 P 0.12916(2) 0.51282(5) 0.38242(4) 0.01818(16) Uani 1 1 d . . . . .
O1 O 0.15686(6) 0.92112(15) 0.25015(14) 0.0410(6) Uani 1 1 d . . . . .
N1 N 0.11170(6) 0.58555(15) 0.54232(13) 0.0158(5) Uani 1 1 d . . . . .
N2 N 0.14109(6) 0.43767(15) 0.55772(13) 0.0165(5) Uani 1 1 d . . . . .
C1 C 0.12997(7) 0.51695(18) 0.50422(16) 0.0158(5) Uani 1 1 d . . . . .
C2 C 0.10413(8) 0.54541(19) 0.62462(16) 0.0207(6) Uani 1 1 d . . . . .
H2A H 0.0756 0.5279 0.6156 0.025 Uiso 1 1 calc R U . . .
H2B H 0.1122 0.5945 0.6737 0.025 Uiso 1 1 calc R U . . .
C3 C 0.13033(8) 0.45220(19) 0.64240(16) 0.0207(6) Uani 1 1 d . . . . .
H3A H 0.1545 0.4634 0.6920 0.025 Uiso 1 1 calc R U . . .
H3B H 0.1154 0.3934 0.6560 0.025 Uiso 1 1 calc R U . . .
C4 C 0.10039(8) 0.68870(18) 0.51694(16) 0.0180(6) Uani 1 1 d . . . . .
C5 C 0.05966(8) 0.71212(19) 0.48467(17) 0.0224(6) Uani 1 1 d . . . . .
C6 C 0.04967(9) 0.8132(2) 0.46790(19) 0.0305(7) Uani 1 1 d . . . . .
H6 H 0.0223 0.8317 0.4464 0.037 Uiso 1 1 calc R U . . .
C7 C 0.07857(9) 0.8866(2) 0.48179(19) 0.0340(7) Uani 1 1 d . . . . .
H7 H 0.0710 0.9550 0.4692 0.041 Uiso 1 1 calc R U . . .
C8 C 0.11853(9) 0.8621(2) 0.51386(18) 0.0299(7) Uani 1 1 d . . . . .
H8 H 0.1381 0.9139 0.5231 0.036 Uiso 1 1 calc R U . . .
C9 C 0.13055(8) 0.76225(19) 0.53292(16) 0.0199(6) Uani 1 1 d . . . . .
C10 C 0.02645(8) 0.6338(2) 0.46835(18) 0.0271(7) Uani 1 1 d . . . . .
H10 H 0.0390 0.5654 0.4727 0.033 Uiso 1 1 calc R U . . .
C11 C 0.00379(9) 0.6417(2) 0.5395(2) 0.0412(8) Uani 1 1 d . . . . .
H11A H 0.0224 0.6307 0.5978 0.062 Uiso 1 1 calc R U . . .
H11B H -0.0174 0.5906 0.5287 0.062 Uiso 1 1 calc R U . . .
H11C H -0.0082 0.7089 0.5374 0.062 Uiso 1 1 calc R U . . .
C12 C -0.00273(9) 0.6443(2) 0.3760(2) 0.0378(8) Uani 1 1 d . . . . .
H12A H -0.0178 0.7073 0.3729 0.057 Uiso 1 1 calc R U . . .
H12B H -0.0213 0.5872 0.3649 0.057 Uiso 1 1 calc R U . . .
H12C H 0.0123 0.6453 0.3313 0.057 Uiso 1 1 calc R U . . .
C13 C 0.17456(8) 0.73730(19) 0.57085(16) 0.0219(6) Uani 1 1 d . . . . .
H13 H 0.1796 0.6713 0.5450 0.026 Uiso 1 1 calc R U . . .
C14 C 0.18476(8) 0.7236(2) 0.67204(17) 0.0288(7) Uani 1 1 d . . . . .
H14A H 0.1779 0.7853 0.6991 0.043 Uiso 1 1 calc R U . . .
H14B H 0.2135 0.7101 0.6952 0.043 Uiso 1 1 calc R U . . .
H14C H 0.1694 0.6669 0.6861 0.043 Uiso 1 1 calc R U . . .
C15 C 0.20288(9) 0.8142(2) 0.54841(19) 0.0332(7) Uani 1 1 d . . . . .
H15A H 0.1950 0.8272 0.4846 0.050 Uiso 1 1 calc R U . . .
H15B H 0.2303 0.7879 0.5659 0.050 Uiso 1 1 calc R U . . .
H15C H 0.2016 0.8772 0.5803 0.050 Uiso 1 1 calc R U . . .
C16 C 0.16867(8) 0.35519(18) 0.55774(16) 0.0172(6) Uani 1 1 d . . . . .
C17 C 0.20935(8) 0.37180(19) 0.59773(16) 0.0204(6) Uani 1 1 d . . . . .
C18 C 0.23495(8) 0.2892(2) 0.60620(18) 0.0280(7) Uani 1 1 d . . . . .
H18 H 0.2628 0.2984 0.6319 0.034 Uiso 1 1 calc R U . . .
C19 C 0.22080(9) 0.1951(2) 0.57830(18) 0.0299(7) Uani 1 1 d . . . . .
H19 H 0.2387 0.1396 0.5855 0.036 Uiso 1 1 calc R U . . .
C20 C 0.18050(9) 0.1809(2) 0.53971(18) 0.0300(7) Uani 1 1 d . . . . .
H20 H 0.1711 0.1153 0.5208 0.036 Uiso 1 1 calc R U . . .
C21 C 0.15319(8) 0.26037(19) 0.52765(16) 0.0219(6) Uani 1 1 d . . . . .
C22 C 0.22640(8) 0.4747(2) 0.62995(17) 0.0242(6) Uani 1 1 d . . . . .
H22 H 0.2035 0.5227 0.6217 0.029 Uiso 1 1 calc R U . . .
C23 C 0.25378(9) 0.5135(2) 0.57491(18) 0.0371(8) Uani 1 1 d . . . . .
H23A H 0.2772 0.4692 0.5837 0.056 Uiso 1 1 calc R U . . .
H23B H 0.2626 0.5821 0.5937 0.056 Uiso 1 1 calc R U . . .
H23C H 0.2391 0.5139 0.5122 0.056 Uiso 1 1 calc R U . . .
C24 C 0.24880(8) 0.4742(2) 0.72852(17) 0.0314(7) Uani 1 1 d . . . . .
H24A H 0.2306 0.4524 0.7632 0.047 Uiso 1 1 calc R U . . .
H24B H 0.2586 0.5422 0.7468 0.047 Uiso 1 1 calc R U . . .
H24C H 0.2715 0.4276 0.7386 0.047 Uiso 1 1 calc R U . . .
C25 C 0.10947(8) 0.2425(2) 0.48233(17) 0.0253(6) Uani 1 1 d . . . . .
H25 H 0.0956 0.3092 0.4731 0.030 Uiso 1 1 calc R U . . .
C26 C 0.10466(10) 0.1935(2) 0.3918(2) 0.0460(9) Uani 1 1 d . . . . .
H26A H 0.1172 0.2363 0.3559 0.069 Uiso 1 1 calc R U . . .
H26B H 0.0761 0.1858 0.3619 0.069 Uiso 1 1 calc R U . . .
H26C H 0.1175 0.1271 0.3995 0.069 Uiso 1 1 calc R U . . .
C27 C 0.08988(9) 0.1771(2) 0.5397(2) 0.0350(7) Uani 1 1 d . . . . .
H27A H 0.1040 0.1125 0.5518 0.053 Uiso 1 1 calc R U . . .
H27B H 0.0618 0.1652 0.5083 0.053 Uiso 1 1 calc R U . . .
H27C H 0.0914 0.2119 0.5956 0.053 Uiso 1 1 calc R U . . .
C28 C 0.13694(8) 0.64107(19) 0.34983(15) 0.0193(6) Uani 1 1 d . . . . .
C29 C 0.17478(8) 0.6714(2) 0.34366(16) 0.0240(6) Uani 1 1 d . . . . .
H29 H 0.1970 0.6277 0.3642 0.029 Uiso 1 1 calc R U . . .
C30 C 0.18023(9) 0.7637(2) 0.30822(18) 0.0300(7) Uani 1 1 d . . . . .
H30 H 0.2058 0.7823 0.3022 0.036 Uiso 1 1 calc R U . . .
C31 C 0.14797(9) 0.8295(2) 0.28128(18) 0.0289(7) Uani 1 1 d . . . . .
C32 C 0.11028(9) 0.8013(2) 0.28645(17) 0.0275(7) Uani 1 1 d . . . . .
H32 H 0.0883 0.8464 0.2682 0.033 Uiso 1 1 calc R U . . .
C33 C 0.10489(8) 0.7065(2) 0.31861(17) 0.0247(6) Uani 1 1 d . . . . .
H33 H 0.0787 0.6857 0.3193 0.030 Uiso 1 1 calc R U . . .
C34 C 0.12667(11) 0.9963(2) 0.2341(2) 0.0506(9) Uani 1 1 d . . . . .
H34A H 0.1047 0.9767 0.1832 0.076 Uiso 1 1 calc R U . . .
H34B H 0.1379 1.0606 0.2217 0.076 Uiso 1 1 calc R U . . .
H34C H 0.1165 1.0035 0.2864 0.076 Uiso 1 1 calc R U . . .
C35 C 0.0000 0.8599(4) 0.7500 0.0590(15) Uani 1 2 d S T P . .
C36 C -0.01589(11) 0.9134(3) 0.8085(3) 0.0613(11) Uani 1 1 d . . . . .
H36 H -0.0271 0.8781 0.8488 0.074 Uiso 1 1 calc R U . . .
C37 C -0.01563(11) 1.0163(3) 0.8088(3) 0.0672(12) Uani 1 1 d . . . . .
H37 H -0.0263 1.0521 0.8498 0.081 Uiso 1 1 calc R U . . .
C38 C 0.0000 1.0683(4) 0.7500 0.0653(17) Uani 1 2 d S T P . .
H38 H 0.0000 1.1399 0.7500 0.078 Uiso 1 2 calc R U P . .
C39 C 0.0000 0.7445(4) 0.7500 0.106(3) Uani 1 2 d S T P . .
H39A H 0.0117 0.7198 0.8103 0.159 Uiso 0.5 1 calc R U P . .
H39B H 0.0159 0.7198 0.7112 0.159 Uiso 0.5 1 calc R U P . .
H39C H -0.0276 0.7198 0.7285 0.159 Uiso 0.5 1 calc R U P . .


_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
S1 P1 1.9674(10) . ?
S2 P1 1.9577(10) . ?
P1 C28 1.817(3) . ?
P1 C1 1.905(2) . ?
O1 C31 1.376(3) . ?
O1 C34 1.418(4) . ?
N1 C1 1.338(3) . ?
N1 C4 1.450(3) . ?
N1 C2 1.484(3) . ?
N2 C1 1.337(3) . ?
N2 C16 1.453(3) . ?
N2 C3 1.486(3) . ?
C2 C3 1.515(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.401(3) . ?
C4 C9 1.403(3) . ?
C5 C6 1.392(4) . ?
C5 C10 1.521(4) . ?
C6 C7 1.372(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(4) . ?
C8 H8 0.9500 . ?
C9 C13 1.518(4) . ?
C10 C11 1.531(4) . ?
C10 C12 1.536(4) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.521(4) . ?
C13 C14 1.542(3) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.399(3) . ?
C16 C17 1.399(3) . ?
C17 C18 1.394(4) . ?
C17 C22 1.519(4) . ?
C18 C19 1.370(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(4) . ?
C20 H20 0.9500 . ?
C21 C25 1.511(4) . ?
C22 C23 1.533(4) . ?
C22 C24 1.534(4) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.530(4) . ?
C25 C27 1.533(4) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C33 1.391(3) . ?
C28 C29 1.400(4) . ?
C29 C30 1.379(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.392(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.382(4) . ?
C32 C33 1.387(4) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.386(4) . ?
C35 C36 1.386(5) 2_556 ?
C35 C39 1.531(7) . ?
C36 C37 1.365(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.374(5) . ?
C37 H37 0.9500 . ?
C38 C37 1.374(5) 2_556 ?
C38 H38 0.9500 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C28 P1 C1 106.98(11) . . ?
C28 P1 S2 109.10(9) . . ?
C1 P1 S2 109.51(8) . . ?
C28 P1 S1 110.31(9) . . ?
C1 P1 S1 99.13(8) . . ?
S2 P1 S1 120.70(5) . . ?
C31 O1 C34 117.4(2) . . ?
C1 N1 C4 130.2(2) . . ?
C1 N1 C2 111.09(19) . . ?
C4 N1 C2 118.69(19) . . ?
C1 N2 C16 132.2(2) . . ?
C1 N2 C3 111.13(19) . . ?
C16 N2 C3 114.85(19) . . ?
N2 C1 N1 110.3(2) . . ?
N2 C1 P1 122.14(18) . . ?
N1 C1 P1 125.90(18) . . ?
N1 C2 C3 102.49(19) . . ?
N1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
N2 C3 C2 102.87(18) . . ?
N2 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
N2 C3 H3B 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C5 C4 C9 122.8(2) . . ?
C5 C4 N1 118.7(2) . . ?
C9 C4 N1 118.3(2) . . ?
C6 C5 C4 117.2(2) . . ?
C6 C5 C10 119.2(2) . . ?
C4 C5 C10 123.6(2) . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 120.9(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C4 117.1(2) . . ?
C8 C9 C13 120.1(2) . . ?
C4 C9 C13 122.8(2) . . ?
C5 C10 C11 110.1(2) . . ?
C5 C10 C12 112.0(2) . . ?
C11 C10 C12 110.2(2) . . ?
C5 C10 H10 108.2 . . ?
C11 C10 H10 108.2 . . ?
C12 C10 H10 108.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C15 113.9(2) . . ?
C9 C13 C14 111.0(2) . . ?
C15 C13 C14 109.4(2) . . ?
C9 C13 H13 107.4 . . ?
C15 C13 H13 107.4 . . ?
C14 C13 H13 107.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 122.8(2) . . ?
C21 C16 N2 119.0(2) . . ?
C17 C16 N2 117.7(2) . . ?
C18 C17 C16 117.3(2) . . ?
C18 C17 C22 119.6(2) . . ?
C16 C17 C22 123.1(2) . . ?
C19 C18 C17 121.5(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 121.9(3) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C16 116.6(2) . . ?
C20 C21 C25 120.2(2) . . ?
C16 C21 C25 123.1(2) . . ?
C17 C22 C23 111.0(2) . . ?
C17 C22 C24 112.2(2) . . ?
C23 C22 C24 110.3(2) . . ?
C17 C22 H22 107.7 . . ?
C23 C22 H22 107.7 . . ?
C24 C22 H22 107.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 C26 110.5(2) . . ?
C21 C25 C27 111.0(2) . . ?
C26 C25 C27 110.5(2) . . ?
C21 C25 H25 108.2 . . ?
C26 C25 H25 108.2 . . ?
C27 C25 H25 108.2 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C33 C28 C29 118.1(2) . . ?
C33 C28 P1 121.2(2) . . ?
C29 C28 P1 120.0(2) . . ?
C30 C29 C28 121.0(3) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C31 119.6(3) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
O1 C31 C32 124.4(3) . . ?
O1 C31 C30 115.1(3) . . ?
C32 C31 C30 120.6(3) . . ?
C31 C32 C33 119.2(3) . . ?
C31 C32 H32 120.4 . . ?
C33 C32 H32 120.4 . . ?
C32 C33 C28 121.4(3) . . ?
C32 C33 H33 119.3 . . ?
C28 C33 H33 119.3 . . ?
O1 C34 H34A 109.5 . . ?
O1 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O1 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 C36 118.3(5) . 2_556 ?
C36 C35 C39 120.8(3) . . ?
C36 C35 C39 120.8(3) 2_556 . ?
C37 C36 C35 120.8(4) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C36 C37 C38 120.2(5) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C37 C38 C37 119.8(6) 2_556 . ?
C37 C38 H38 120.1 2_556 . ?
C37 C38 H38 120.1 . . ?
C35 C39 H39A 109.5 . . ?
C35 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C35 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N2 C1 N1 -164.6(2) . . . . ?
C3 N2 C1 N1 -1.1(3) . . . . ?
C16 N2 C1 P1 29.5(4) . . . . ?
C3 N2 C1 P1 -167.01(17) . . . . ?
C4 N1 C1 N2 168.9(2) . . . . ?
C2 N1 C1 N2 -8.7(3) . . . . ?
C4 N1 C1 P1 -25.8(4) . . . . ?
C2 N1 C1 P1 156.57(18) . . . . ?
C1 N1 C2 C3 14.2(3) . . . . ?
C4 N1 C2 C3 -163.7(2) . . . . ?
C1 N2 C3 C2 9.8(3) . . . . ?
C16 N2 C3 C2 176.4(2) . . . . ?
N1 C2 C3 N2 -13.6(2) . . . . ?
C1 N1 C4 C5 110.1(3) . . . . ?
C2 N1 C4 C5 -72.4(3) . . . . ?
C1 N1 C4 C9 -75.2(3) . . . . ?
C2 N1 C4 C9 102.2(3) . . . . ?
C9 C4 C5 C6 0.4(4) . . . . ?
N1 C4 C5 C6 174.8(2) . . . . ?
C9 C4 C5 C10 -178.9(2) . . . . ?
N1 C4 C5 C10 -4.6(4) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C10 C5 C6 C7 179.9(3) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C7 C8 C9 C4 0.8(4) . . . . ?
C7 C8 C9 C13 -178.1(2) . . . . ?
C5 C4 C9 C8 -1.0(4) . . . . ?
N1 C4 C9 C8 -175.4(2) . . . . ?
C5 C4 C9 C13 177.8(2) . . . . ?
N1 C4 C9 C13 3.4(4) . . . . ?
C6 C5 C10 C11 -72.5(3) . . . . ?
C4 C5 C10 C11 106.8(3) . . . . ?
C6 C5 C10 C12 50.4(3) . . . . ?
C4 C5 C10 C12 -130.3(3) . . . . ?
C8 C9 C13 C15 -25.2(3) . . . . ?
C4 C9 C13 C15 156.0(2) . . . . ?
C8 C9 C13 C14 98.9(3) . . . . ?
C4 C9 C13 C14 -79.9(3) . . . . ?
C1 N2 C16 C21 -103.4(3) . . . . ?
C3 N2 C16 C21 93.6(3) . . . . ?
C1 N2 C16 C17 84.0(3) . . . . ?
C3 N2 C16 C17 -79.0(3) . . . . ?
C21 C16 C17 C18 0.7(4) . . . . ?
N2 C16 C17 C18 173.0(2) . . . . ?
C21 C16 C17 C22 179.5(2) . . . . ?
N2 C16 C17 C22 -8.2(3) . . . . ?
C16 C17 C18 C19 -1.4(4) . . . . ?
C22 C17 C18 C19 179.8(2) . . . . ?
C17 C18 C19 C20 1.0(4) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C19 C20 C21 C16 -0.8(4) . . . . ?
C19 C20 C21 C25 178.0(2) . . . . ?
C17 C16 C21 C20 0.3(4) . . . . ?
N2 C16 C21 C20 -171.9(2) . . . . ?
C17 C16 C21 C25 -178.4(2) . . . . ?
N2 C16 C21 C25 9.4(4) . . . . ?
C18 C17 C22 C23 65.7(3) . . . . ?
C16 C17 C22 C23 -113.0(3) . . . . ?
C18 C17 C22 C24 -58.2(3) . . . . ?
C16 C17 C22 C24 123.0(3) . . . . ?
C20 C21 C25 C26 -54.5(3) . . . . ?
C16 C21 C25 C26 124.1(3) . . . . ?
C20 C21 C25 C27 68.4(3) . . . . ?
C16 C21 C25 C27 -112.9(3) . . . . ?
C1 P1 C28 C33 -88.6(2) . . . . ?
S2 P1 C28 C33 153.01(19) . . . . ?
S1 P1 C28 C33 18.3(2) . . . . ?
C1 P1 C28 C29 100.6(2) . . . . ?
S2 P1 C28 C29 -17.8(2) . . . . ?
S1 P1 C28 C29 -152.54(18) . . . . ?
C33 C28 C29 C30 0.4(4) . . . . ?
P1 C28 C29 C30 171.5(2) . . . . ?
C28 C29 C30 C31 2.5(4) . . . . ?
C34 O1 C31 C32 9.2(4) . . . . ?
C34 O1 C31 C30 -170.9(3) . . . . ?
C29 C30 C31 O1 177.5(2) . . . . ?
C29 C30 C31 C32 -2.6(4) . . . . ?
O1 C31 C32 C33 179.6(2) . . . . ?
C30 C31 C32 C33 -0.2(4) . . . . ?
C31 C32 C33 C28 3.3(4) . . . . ?
C29 C28 C33 C32 -3.4(4) . . . . ?
P1 C28 C33 C32 -174.3(2) . . . . ?
C36 C35 C36 C37 -0.4(2) 2_556 . . . ?
C39 C35 C36 C37 179.6(2) . . . . ?
C35 C36 C37 C38 0.9(5) . . . . ?
C36 C37 C38 C37 -0.4(2) . . . 2_556 ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.065

