# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1550753'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;
_audit_creation_date             2017-05-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H37 B N3 P S'
_chemical_formula_sum            'C26 H37 B N3 P S'
_chemical_formula_weight         465.42
_chemical_melting_point          ?
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'
B B 0.0013 0.0007 '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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.5713(10)
_cell_length_b                   13.5389(12)
_cell_length_c                   16.9115(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.317(2)
_cell_angle_gamma                90
_cell_volume                     2614.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9777
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.086
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0584 before and 0.0534 after correction. The Ratio of minimum to maximum transmission is 0.9273. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            57709
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.101
_diffrn_reflns_theta_min         1.783
_diffrn_ambient_temperature      90(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker D8 Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6158
_reflns_number_total             7687
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         7687
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0399P)²+1.2771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0940
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All B(H,H,H) groups, All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20),
 C21(H21)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C24(H24A,
 H24B,H24C), C26(H26A,H26B,H26C), B1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.04912(3) 0.69069(2) 0.05631(2) 0.01651(7) Uani 1 1 d . . . . .
P1 P 0.42101(2) 0.71240(2) 0.30951(2) 0.01135(7) Uani 1 1 d . . . . .
N1 N 0.23112(8) 0.71846(7) 0.18124(6) 0.01133(19) Uani 1 1 d . . . . .
N2 N 0.20490(8) 0.56538(7) 0.14222(6) 0.01181(19) Uani 1 1 d . . . . .
N3 N 0.34193(9) 0.72105(8) 0.38228(6) 0.0163(2) Uani 1 1 d . . . . .
C1 C 0.16203(9) 0.65925(9) 0.12778(7) 0.0119(2) Uani 1 1 d . . . . .
C2 C 0.32010(9) 0.66213(9) 0.22627(7) 0.0112(2) Uani 1 1 d . . . . .
C3 C 0.30210(9) 0.56717(9) 0.20136(7) 0.0123(2) Uani 1 1 d . . . . .
H3 H 0.348300 0.511784 0.221182 0.015 Uiso 1 1 calc R . . . .
C4 C 0.21523(10) 0.82613(9) 0.19186(7) 0.0140(2) Uani 1 1 d . . . . .
H4 H 0.276694 0.847093 0.237304 0.017 Uiso 1 1 calc R . . . .
C5 C 0.09741(11) 0.84981(11) 0.21667(9) 0.0233(3) Uani 1 1 d . . . . .
H5A H 0.034378 0.834927 0.172214 0.035 Uiso 1 1 calc GR . . . .
H5B H 0.094743 0.920004 0.230422 0.035 Uiso 1 1 calc GR . . . .
H5C H 0.087361 0.809743 0.263338 0.035 Uiso 1 1 calc GR . . . .
C6 C 0.23827(12) 0.88318(10) 0.11866(8) 0.0219(3) Uani 1 1 d . . . . .
H6A H 0.318704 0.870930 0.109905 0.033 Uiso 1 1 calc GR . . . .
H6B H 0.227609 0.953957 0.127265 0.033 Uiso 1 1 calc GR . . . .
H6C H 0.183344 0.861466 0.071580 0.033 Uiso 1 1 calc GR . . . .
C7 C 0.15219(10) 0.47636(9) 0.10027(7) 0.0139(2) Uani 1 1 d . . . . .
H7 H 0.071194 0.494013 0.073809 0.017 Uiso 1 1 calc R . . . .
C8 C 0.14189(12) 0.39430(10) 0.16004(8) 0.0205(3) Uani 1 1 d . . . . .
H8A H 0.220260 0.370553 0.182759 0.031 Uiso 1 1 calc GR . . . .
H8B H 0.096026 0.339732 0.132808 0.031 Uiso 1 1 calc GR . . . .
H8C H 0.102754 0.419678 0.203107 0.031 Uiso 1 1 calc GR . . . .
C9 C 0.22095(11) 0.44607(10) 0.03517(8) 0.0187(2) Uani 1 1 d . . . . .
H9A H 0.219968 0.500026 -0.003565 0.028 Uiso 1 1 calc GR . . . .
H9B H 0.185313 0.387080 0.007804 0.028 Uiso 1 1 calc GR . . . .
H9C H 0.302026 0.431536 0.059177 0.028 Uiso 1 1 calc GR . . . .
C10 C 0.52805(9) 0.60986(9) 0.33114(7) 0.0121(2) Uani 1 1 d . . . . .
H10 H 0.487777 0.544279 0.327311 0.015 Uiso 1 1 calc R . . . .
C11 C 0.61677(10) 0.61588(9) 0.27414(7) 0.0126(2) Uani 1 1 d . . . . .
C12 C 0.60074(10) 0.60575(9) 0.19155(8) 0.0161(2) Uani 1 1 d . . . . .
H12 H 0.525428 0.591569 0.162216 0.019 Uiso 1 1 calc R . . . .
C13 C 0.69689(11) 0.61671(10) 0.15223(8) 0.0205(3) Uani 1 1 d . . . . .
H13 H 0.686617 0.610543 0.095570 0.025 Uiso 1 1 calc R . . . .
C14 C 0.80783(11) 0.63658(10) 0.19482(9) 0.0214(3) Uani 1 1 d . . . . .
H14 H 0.872522 0.643352 0.167077 0.026 Uiso 1 1 calc R . . . .
C15 C 0.82442(10) 0.64655(10) 0.27770(8) 0.0188(3) Uani 1 1 d . . . . .
H15 H 0.900084 0.659830 0.306886 0.023 Uiso 1 1 calc R . . . .
C16 C 0.72834(10) 0.63676(9) 0.31738(8) 0.0139(2) Uani 1 1 d . . . . .
C17 C 0.72054(10) 0.64149(9) 0.40284(8) 0.0142(2) Uani 1 1 d . . . . .
C18 C 0.80692(11) 0.65654(9) 0.46915(8) 0.0185(3) Uani 1 1 d . . . . .
H18 H 0.885793 0.668119 0.462602 0.022 Uiso 1 1 calc R . . . .
C19 C 0.77585(11) 0.65434(10) 0.54510(8) 0.0212(3) Uani 1 1 d . . . . .
H19 H 0.833794 0.665836 0.590770 0.025 Uiso 1 1 calc R . . . .
C20 C 0.66062(11) 0.63547(10) 0.55513(8) 0.0199(3) Uani 1 1 d . . . . .
H20 H 0.640884 0.633551 0.607492 0.024 Uiso 1 1 calc R . . . .
C21 C 0.57412(11) 0.61937(9) 0.48865(8) 0.0168(2) Uani 1 1 d . . . . .
H21 H 0.495800 0.605683 0.495434 0.020 Uiso 1 1 calc R . . . .
C22 C 0.60403(10) 0.62363(9) 0.41270(7) 0.0133(2) Uani 1 1 d . . . . .
C23 C 0.27944(11) 0.63428(11) 0.40637(8) 0.0208(3) Uani 1 1 d . . . . .
H23A H 0.292851 0.630315 0.465606 0.025 Uiso 1 1 calc R . . . .
H23B H 0.313346 0.574134 0.385952 0.025 Uiso 1 1 calc R . . . .
C24 C 0.14787(11) 0.63490(12) 0.37652(9) 0.0260(3) Uani 1 1 d . . . . .
H24A H 0.133393 0.635346 0.317796 0.039 Uiso 1 1 calc GR . . . .
H24B H 0.113145 0.693982 0.396573 0.039 Uiso 1 1 calc GR . . . .
H24C H 0.112487 0.575782 0.395988 0.039 Uiso 1 1 calc GR . . . .
C25 C 0.32681(11) 0.81471(11) 0.42420(8) 0.0225(3) Uani 1 1 d . . . . .
H25A H 0.246976 0.816411 0.438149 0.027 Uiso 1 1 calc R . . . .
H25B H 0.333396 0.870306 0.387164 0.027 Uiso 1 1 calc R . . . .
C26 C 0.41516(13) 0.82976(12) 0.50005(9) 0.0288(3) Uani 1 1 d . . . . .
H26A H 0.494495 0.829765 0.486733 0.043 Uiso 1 1 calc GR . . . .
H26B H 0.407799 0.776113 0.537820 0.043 Uiso 1 1 calc GR . . . .
H26C H 0.400186 0.893114 0.524534 0.043 Uiso 1 1 calc GR . . . .
B1 B 0.50333(12) 0.83146(11) 0.28996(10) 0.0196(3) Uani 1 1 d . . . . .
H1A H 0.452423 0.888680 0.293159 0.029 Uiso 1 1 calc GR . . . .
H1B H 0.525452 0.828424 0.236470 0.029 Uiso 1 1 calc GR . . . .
H1C H 0.573964 0.837799 0.330306 0.029 Uiso 1 1 calc GR . . . .


_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 C1 1.6845(12) . ?
P1 N3 1.6524(11) . ?
P1 C2 1.8099(12) . ?
P1 C10 1.8571(12) . ?
P1 B1 1.9279(15) . ?
N1 C1 1.3657(14) . ?
N1 C2 1.4028(14) . ?
N1 C4 1.4838(15) . ?
N2 C1 1.3717(15) . ?
N2 C3 1.3789(14) . ?
N2 C7 1.4792(15) . ?
N3 C23 1.4711(17) . ?
N3 C25 1.4769(17) . ?
C2 C3 1.3584(16) . ?
C3 H3 0.9500 . ?
C4 H4 1.0000 . ?
C4 C5 1.5241(17) . ?
C4 C6 1.5188(18) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7 1.0000 . ?
C7 C8 1.5196(18) . ?
C7 C9 1.5156(18) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.5198(16) . ?
C10 C22 1.5224(16) . ?
C11 C12 1.3857(17) . ?
C11 C16 1.4056(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3933(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.3927(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.3948(17) . ?
C16 C17 1.4640(18) . ?
C17 C18 1.3911(16) . ?
C17 C22 1.4058(16) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.3947(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.3960(17) . ?
C21 H21 0.9500 . ?
C21 C22 1.3845(18) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5245(17) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.5191(18) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
B1 H1A 0.9800 . ?
B1 H1B 0.9800 . ?
B1 H1C 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
N3 P1 C2 103.92(5) . . ?
N3 P1 C10 109.78(5) . . ?
N3 P1 B1 114.65(6) . . ?
C2 P1 C10 101.41(5) . . ?
C2 P1 B1 117.10(6) . . ?
C10 P1 B1 109.06(6) . . ?
C1 N1 C2 109.87(10) . . ?
C1 N1 C4 125.88(9) . . ?
C2 N1 C4 124.25(9) . . ?
C1 N2 C3 109.99(9) . . ?
C1 N2 C7 124.08(9) . . ?
C3 N2 C7 125.93(10) . . ?
C23 N3 P1 120.40(9) . . ?
C23 N3 C25 116.81(11) . . ?
C25 N3 P1 122.76(9) . . ?
N1 C1 S1 129.02(9) . . ?
N1 C1 N2 105.65(9) . . ?
N2 C1 S1 125.31(9) . . ?
N1 C2 P1 122.83(8) . . ?
C3 C2 P1 130.11(9) . . ?
C3 C2 N1 106.49(10) . . ?
N2 C3 H3 126.0 . . ?
C2 C3 N2 107.92(10) . . ?
C2 C3 H3 126.0 . . ?
N1 C4 H4 106.6 . . ?
N1 C4 C5 111.96(10) . . ?
N1 C4 C6 111.07(10) . . ?
C5 C4 H4 106.6 . . ?
C6 C4 H4 106.6 . . ?
C6 C4 C5 113.59(11) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7 107.7 . . ?
N2 C7 C8 110.33(10) . . ?
N2 C7 C9 110.16(10) . . ?
C8 C7 H7 107.7 . . ?
C9 C7 H7 107.7 . . ?
C9 C7 C8 113.10(11) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
P1 C10 H10 111.2 . . ?
C11 C10 P1 109.42(8) . . ?
C11 C10 H10 111.2 . . ?
C11 C10 C22 102.58(9) . . ?
C22 C10 P1 110.85(8) . . ?
C22 C10 H10 111.2 . . ?
C12 C11 C10 129.79(10) . . ?
C12 C11 C16 120.40(11) . . ?
C16 C11 C10 109.80(10) . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 118.92(11) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 120.94(13) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.35(12) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.02(12) . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C17 108.91(10) . . ?
C15 C16 C11 120.36(12) . . ?
C15 C16 C17 130.70(11) . . ?
C18 C17 C16 130.62(11) . . ?
C18 C17 C22 120.48(12) . . ?
C22 C17 C16 108.85(10) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.85(12) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.80(12) . . ?
C20 C19 H19 119.6 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.37(13) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.10(12) . . ?
C22 C21 H21 120.5 . . ?
C17 C22 C10 109.75(11) . . ?
C21 C22 C10 129.87(10) . . ?
C21 C22 C17 120.38(11) . . ?
N3 C23 H23A 108.7 . . ?
N3 C23 H23B 108.7 . . ?
N3 C23 C24 114.40(11) . . ?
H23A C23 H23B 107.6 . . ?
C24 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N3 C25 H25A 108.8 . . ?
N3 C25 H25B 108.8 . . ?
N3 C25 C26 113.87(11) . . ?
H25A C25 H25B 107.7 . . ?
C26 C25 H25A 108.8 . . ?
C26 C25 H25B 108.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
P1 B1 H1A 109.5 . . ?
P1 B1 H1B 109.5 . . ?
P1 B1 H1C 109.5 . . ?
H1A B1 H1B 109.5 . . ?
H1A B1 H1C 109.5 . . ?
H1B B1 H1C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#END---------------------------------------------------------------------------

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1550752'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;
_audit_creation_date             2017-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H36 N3 P S'
_chemical_formula_sum            'C26 H36 N3 P S'
_chemical_formula_weight         453.61
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4412(16)
_cell_length_b                   15.818(3)
_cell_length_c                   17.317(3)
_cell_angle_alpha                99.675(4)
_cell_angle_beta                 90.025(4)
_cell_angle_gamma                92.645(4)
_cell_volume                     2546.5(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0531 before and 0.0473 after correction. The Ratio of minimum to maximum transmission is 0.9303. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            55378
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.096
_diffrn_reflns_theta_min         1.193
_diffrn_ambient_temperature      90(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Bruker D8 Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11017
_reflns_number_total             14925
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     627
_refine_ls_number_reflns         14925
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+1.1846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1120
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C11A, C12A, C13A, C14A, C15A, C16A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=
 Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=1-FVAR(1)
 Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=
 Sof(H15)=Sof(C16)=Sof(H16)=FVAR(1)
 Sof(H10A)=1-FVAR(2)
 Sof(H10)=FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C10(H10), C10(H10A), C30(H30), C33(H33), C36(H36)
4.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C25(H25A,H25B), C49(H49A,H49B), C51(H51A,H51B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A),
 C16A(H16A), C29(H29), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42),
 C44(H44), C45(H45), C46(H46), C47(H47), C48(H48)
4.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C24(H24A,
 H24B,H24C), C26(H26A,H26B,H26C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C),
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C50(H50A,H50B,H50C), C52(H52A,H52B,
 H52C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.56609(4) 0.64677(2) 0.54295(2) 0.01449(8) Uani 1 1 d . . . . .
P1 P 0.69755(4) 0.83067(2) 0.29944(2) 0.01234(8) Uani 1 1 d . . . . .
N1 N 0.62172(13) 0.74907(8) 0.43113(7) 0.0119(2) Uani 1 1 d . . . . .
N2 N 0.67834(13) 0.61601(8) 0.39580(7) 0.0113(2) Uani 1 1 d . . . . .
N3 N 0.85919(14) 0.87434(8) 0.32872(8) 0.0142(3) Uani 1 1 d . . . . .
C1 C 0.62260(15) 0.67127(9) 0.45599(8) 0.0113(3) Uani 1 1 d . . . . .
C2 C 0.67868(15) 0.74220(9) 0.35482(8) 0.0117(3) Uani 1 1 d . . . . .
C3 C 0.71341(15) 0.65901(9) 0.33476(8) 0.0122(3) Uani 1 1 d . . . . .
H3 H 0.754939 0.634453 0.286716 0.015 Uiso 1 1 calc R . . . .
C4 C 0.56425(17) 0.82505(10) 0.48141(9) 0.0162(3) Uani 1 1 d . . . . .
H4 H 0.547507 0.808211 0.533910 0.019 Uiso 1 1 calc R . . . .
C5 C 0.4207(2) 0.84448(13) 0.45147(11) 0.0290(4) Uani 1 1 d . . . . .
H5A H 0.431156 0.860906 0.399597 0.043 Uiso 1 1 calc GR . . . .
H5B H 0.381188 0.891757 0.487722 0.043 Uiso 1 1 calc GR . . . .
H5C H 0.356688 0.793342 0.447709 0.043 Uiso 1 1 calc GR . . . .
C6 C 0.6688(2) 0.90157(12) 0.49473(12) 0.0307(4) Uani 1 1 d . . . . .
H6A H 0.761386 0.883233 0.509331 0.046 Uiso 1 1 calc GR . . . .
H6B H 0.634827 0.944954 0.536971 0.046 Uiso 1 1 calc GR . . . .
H6C H 0.677828 0.926100 0.446535 0.046 Uiso 1 1 calc GR . . . .
C7 C 0.71104(16) 0.52617(9) 0.39936(9) 0.0131(3) Uani 1 1 d . . . . .
H7 H 0.657542 0.507545 0.443908 0.016 Uiso 1 1 calc R . . . .
C8 C 0.66507(19) 0.46698(10) 0.32401(10) 0.0203(3) Uani 1 1 d . . . . .
H8A H 0.564483 0.473810 0.313829 0.031 Uiso 1 1 calc GR . . . .
H8B H 0.679564 0.407289 0.329405 0.031 Uiso 1 1 calc GR . . . .
H8C H 0.721590 0.481735 0.280297 0.031 Uiso 1 1 calc GR . . . .
C9 C 0.86901(17) 0.52235(11) 0.41532(10) 0.0192(3) Uani 1 1 d . . . . .
H9A H 0.922979 0.539954 0.371895 0.029 Uiso 1 1 calc GR . . . .
H9B H 0.890940 0.463525 0.420252 0.029 Uiso 1 1 calc GR . . . .
H9C H 0.894787 0.561104 0.464096 0.029 Uiso 1 1 calc GR . . . .
C10 C 0.72891(16) 0.76877(10) 0.19812(9) 0.0148(3) Uani 1 1 d . . . . .
H10 H 0.802725 0.726131 0.201389 0.018 Uiso 0.81(12) 1 calc R . P A 1
H10A H 0.791716 0.721967 0.206783 0.018 Uiso 0.19(12) 1 calc R . P A 2
C17 C 0.59666(16) 0.72226(10) 0.15866(9) 0.0148(3) Uani 1 1 d . . . . .
C18 C 0.47087(18) 0.76335(11) 0.15115(10) 0.0211(3) Uani 1 1 d . . . . .
H18 H 0.465458 0.822409 0.172783 0.025 Uiso 1 1 calc R . . . .
C19 C 0.35336(19) 0.71934(13) 0.11254(10) 0.0282(4) Uani 1 1 d . . . . .
H19 H 0.268916 0.748539 0.107794 0.034 Uiso 1 1 calc R . . . .
C20 C 0.3589(2) 0.63344(13) 0.08112(10) 0.0308(4) Uani 1 1 d . . . . .
H20 H 0.278476 0.603250 0.055069 0.037 Uiso 1 1 calc R . . . .
C21 C 0.4824(2) 0.59179(12) 0.08787(10) 0.0282(4) Uani 1 1 d . . . . .
H21 H 0.486810 0.532752 0.065933 0.034 Uiso 1 1 calc R . . . .
C22 C 0.60075(19) 0.63535(10) 0.12654(9) 0.0199(3) Uani 1 1 d . . . . .
H22 H 0.684759 0.605655 0.131059 0.024 Uiso 1 1 calc R . . . .
C23 C 0.88658(18) 0.96589(10) 0.32393(9) 0.0182(3) Uani 1 1 d . . . . .
H23A H 0.794717 0.992852 0.320527 0.022 Uiso 1 1 calc R . . . .
H23B H 0.939196 0.970274 0.275208 0.022 Uiso 1 1 calc R . . . .
C24 C 0.9708(2) 1.01571(11) 0.39331(10) 0.0241(4) Uani 1 1 d . . . . .
H24A H 0.981390 1.076295 0.387665 0.036 Uiso 1 1 calc GR . . . .
H24B H 1.064776 0.992126 0.394920 0.036 Uiso 1 1 calc GR . . . .
H24C H 0.920594 1.010774 0.441969 0.036 Uiso 1 1 calc GR . . . .
C25 C 0.98507(17) 0.82267(10) 0.32751(9) 0.0173(3) Uani 1 1 d . . . . .
H25A H 1.066463 0.854024 0.307440 0.021 Uiso 1 1 calc R . . . .
H25B H 0.967369 0.768092 0.290766 0.021 Uiso 1 1 calc R . . . .
C26 C 1.02433(18) 0.80239(11) 0.40774(10) 0.0214(3) Uani 1 1 d . . . . .
H26A H 1.108095 0.767576 0.402926 0.032 Uiso 1 1 calc GR . . . .
H26B H 0.944894 0.770513 0.427718 0.032 Uiso 1 1 calc GR . . . .
H26C H 1.045213 0.856061 0.444075 0.032 Uiso 1 1 calc GR . . . .
C11 C 0.7908(8) 0.8397(5) 0.1549(5) 0.0134(10) Uani 0.687(15) 1 d . . P B 1
C12 C 0.7209(6) 0.9142(3) 0.1476(3) 0.0175(8) Uani 0.687(15) 1 d . . P B 1
H12 H 0.626668 0.920557 0.166080 0.021 Uiso 0.687(15) 1 calc R . P B 1
C13 C 0.7872(7) 0.9788(3) 0.1137(2) 0.0258(10) Uani 0.687(15) 1 d . . P B 1
H13 H 0.738054 1.028870 0.109202 0.031 Uiso 0.687(15) 1 calc R . P B 1
C14 C 0.9243(7) 0.9710(3) 0.08643(19) 0.0282(12) Uani 0.687(15) 1 d . . P B 1
H14 H 0.970054 1.016071 0.064502 0.034 Uiso 0.687(15) 1 calc R . P B 1
C15 C 0.9948(5) 0.8971(4) 0.0912(2) 0.0280(12) Uani 0.687(15) 1 d . . P B 1
H15 H 1.088152 0.890603 0.071206 0.034 Uiso 0.687(15) 1 calc R . P B 1
C16 C 0.9279(6) 0.8321(3) 0.1255(3) 0.0220(9) Uani 0.687(15) 1 d . . P B 1
H16 H 0.976853 0.781626 0.128774 0.026 Uiso 0.687(15) 1 calc R . P B 1
C11A C 0.817(2) 0.8231(12) 0.1506(13) 0.019(3) Uani 0.313(15) 1 d . U P B 2
C12A C 0.7628(15) 0.8994(9) 0.1388(8) 0.025(2) Uani 0.313(15) 1 d . U P B 2
H12A H 0.670156 0.913311 0.156451 0.030 Uiso 0.313(15) 1 calc R . P B 2
C13A C 0.8447(15) 0.9575(8) 0.1003(7) 0.033(3) Uani 0.313(15) 1 d . U P B 2
H13A H 0.808686 1.010605 0.092513 0.040 Uiso 0.313(15) 1 calc R . P B 2
C14A C 0.9772(13) 0.9344(13) 0.0747(8) 0.045(4) Uani 0.313(15) 1 d . U P B 2
H14A H 1.033243 0.971872 0.048331 0.054 Uiso 0.313(15) 1 calc R . P B 2
C15A C 1.0297(12) 0.8591(14) 0.0863(9) 0.055(4) Uani 0.313(15) 1 d . U P B 2
H15A H 1.122306 0.844719 0.068882 0.067 Uiso 0.313(15) 1 calc R . P B 2
C16A C 0.9479(13) 0.8031(11) 0.1237(8) 0.030(3) Uani 0.313(15) 1 d . U P B 2
H16A H 0.984410 0.749789 0.130391 0.036 Uiso 0.313(15) 1 calc R . P B 2
S2 S -0.00268(4) 0.58673(3) 0.18655(2) 0.01985(9) Uani 1 1 d . . . . .
P2 P 0.19210(4) 0.25311(3) 0.17073(2) 0.01349(8) Uani 1 1 d . . . . .
N4 N 0.08221(14) 0.42005(8) 0.16651(7) 0.0154(3) Uani 1 1 d . . . . .
N5 N 0.16810(13) 0.50173(8) 0.27189(7) 0.0124(2) Uani 1 1 d . . . . .
N6 N 0.35772(14) 0.24955(9) 0.13621(7) 0.0160(3) Uani 1 1 d . . . . .
C27 C 0.08386(16) 0.50187(10) 0.20781(9) 0.0145(3) Uani 1 1 d . . . . .
C28 C 0.16489(16) 0.36784(10) 0.20521(9) 0.0139(3) Uani 1 1 d . . . . .
C29 C 0.21617(15) 0.42039(9) 0.27055(9) 0.0132(3) Uani 1 1 d . . . . .
H29 H 0.275603 0.403754 0.309118 0.016 Uiso 1 1 calc R . . . .
C30 C 0.0054(2) 0.39459(12) 0.09097(10) 0.0254(4) Uani 1 1 d . . . . .
H30 H -0.043742 0.446567 0.081392 0.030 Uiso 1 1 calc R . . . .
C31 C 0.1081(3) 0.37418(16) 0.02444(11) 0.0438(6) Uani 1 1 d . . . . .
H31A H 0.180108 0.421235 0.026921 0.066 Uiso 1 1 calc GR . . . .
H31B H 0.056734 0.367141 -0.025580 0.066 Uiso 1 1 calc GR . . . .
H31C H 0.154219 0.320900 0.028781 0.066 Uiso 1 1 calc GR . . . .
C32 C -0.1108(2) 0.32568(16) 0.09517(14) 0.0446(6) Uani 1 1 d . . . . .
H32A H -0.067785 0.271122 0.098323 0.067 Uiso 1 1 calc GR . . . .
H32B H -0.170818 0.318940 0.048157 0.067 Uiso 1 1 calc GR . . . .
H32C H -0.168548 0.342557 0.141723 0.067 Uiso 1 1 calc GR . . . .
C33 C 0.21196(16) 0.57972(10) 0.32800(9) 0.0137(3) Uani 1 1 d . . . . .
H33 H 0.129496 0.617610 0.336164 0.016 Uiso 1 1 calc R . . . .
C34 C 0.33268(19) 0.62822(11) 0.29334(10) 0.0226(4) Uani 1 1 d . . . . .
H34A H 0.414024 0.591665 0.283768 0.034 Uiso 1 1 calc GR . . . .
H34B H 0.360391 0.680460 0.330147 0.034 Uiso 1 1 calc GR . . . .
H34C H 0.301274 0.643715 0.243827 0.034 Uiso 1 1 calc GR . . . .
C35 C 0.25254(17) 0.55692(11) 0.40672(9) 0.0179(3) Uani 1 1 d . . . . .
H35A H 0.175016 0.522303 0.425229 0.027 Uiso 1 1 calc GR . . . .
H35B H 0.270234 0.609690 0.444732 0.027 Uiso 1 1 calc GR . . . .
H35C H 0.338509 0.524067 0.400923 0.027 Uiso 1 1 calc GR . . . .
C36 C 0.20424(16) 0.22471(9) 0.27157(9) 0.0128(3) Uani 1 1 d . . . . .
H36 H 0.266557 0.269772 0.304256 0.015 Uiso 1 1 calc R . . . .
C37 C 0.27247(16) 0.13937(10) 0.26824(9) 0.0134(3) Uani 1 1 d . . . . .
C38 C 0.40599(17) 0.13841(11) 0.30226(9) 0.0177(3) Uani 1 1 d . . . . .
H38 H 0.453990 0.191051 0.324291 0.021 Uiso 1 1 calc R . . . .
C39 C 0.46980(19) 0.06148(11) 0.30438(10) 0.0227(4) Uani 1 1 d . . . . .
H39 H 0.560586 0.061793 0.328127 0.027 Uiso 1 1 calc R . . . .
C40 C 0.40124(19) -0.01601(11) 0.27185(10) 0.0235(4) Uani 1 1 d . . . . .
H40 H 0.443865 -0.068700 0.274525 0.028 Uiso 1 1 calc R . . . .
C41 C 0.27109(19) -0.01602(11) 0.23570(11) 0.0242(4) Uani 1 1 d . . . . .
H41 H 0.225183 -0.068757 0.212107 0.029 Uiso 1 1 calc R . . . .
C42 C 0.20653(18) 0.06128(10) 0.23365(10) 0.0204(3) Uani 1 1 d . . . . .
H42 H 0.116971 0.060747 0.208502 0.024 Uiso 1 1 calc R . . . .
C43 C 0.05667(16) 0.22833(9) 0.30687(9) 0.0139(3) Uani 1 1 d . . . . .
C44 C 0.04031(17) 0.26973(10) 0.38390(9) 0.0169(3) Uani 1 1 d . . . . .
H44 H 0.121215 0.293808 0.413759 0.020 Uiso 1 1 calc R . . . .
C45 C -0.09383(18) 0.27603(11) 0.41734(10) 0.0214(3) Uani 1 1 d . . . . .
H45 H -0.103669 0.304239 0.469860 0.026 Uiso 1 1 calc R . . . .
C46 C -0.21286(18) 0.24147(11) 0.37458(11) 0.0241(4) Uani 1 1 d . . . . .
H46 H -0.304220 0.246456 0.397408 0.029 Uiso 1 1 calc R . . . .
C47 C -0.19787(18) 0.19953(12) 0.29821(11) 0.0238(4) Uani 1 1 d . . . . .
H47 H -0.279107 0.175084 0.268856 0.029 Uiso 1 1 calc R . . . .
C48 C -0.06412(17) 0.19312(11) 0.26439(10) 0.0188(3) Uani 1 1 d . . . . .
H48 H -0.054887 0.164544 0.211944 0.023 Uiso 1 1 calc R . . . .
C49 C 0.47880(17) 0.30320(10) 0.17221(9) 0.0174(3) Uani 1 1 d . . . . .
H49A H 0.564340 0.268833 0.167120 0.021 Uiso 1 1 calc R . . . .
H49B H 0.460490 0.320926 0.228766 0.021 Uiso 1 1 calc R . . . .
C50 C 0.50745(19) 0.38317(12) 0.13511(10) 0.0245(4) Uani 1 1 d . . . . .
H50A H 0.524360 0.366109 0.078941 0.037 Uiso 1 1 calc GR . . . .
H50B H 0.591171 0.415591 0.159905 0.037 Uiso 1 1 calc GR . . . .
H50C H 0.425209 0.419193 0.142664 0.037 Uiso 1 1 calc GR . . . .
C51 C 0.38115(19) 0.19902(12) 0.05828(10) 0.0240(4) Uani 1 1 d . . . . .
H51A H 0.424908 0.237123 0.024158 0.029 Uiso 1 1 calc R . . . .
H51B H 0.288416 0.176550 0.034847 0.029 Uiso 1 1 calc R . . . .
C52 C 0.4757(3) 0.12440(15) 0.06054(14) 0.0493(6) Uani 1 1 d . . . . .
H52A H 0.487117 0.092875 0.007312 0.074 Uiso 1 1 calc GR . . . .
H52B H 0.432302 0.085864 0.093545 0.074 Uiso 1 1 calc GR . . . .
H52C H 0.568753 0.146284 0.082219 0.074 Uiso 1 1 calc GR . . . .


_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 C1 1.6973(15) . ?
P1 N3 1.6874(13) . ?
P1 C2 1.8270(15) . ?
P1 C10 1.8906(16) . ?
N1 C1 1.3707(19) . ?
N1 C2 1.4161(19) . ?
N1 C4 1.4851(19) . ?
N2 C1 1.3653(18) . ?
N2 C3 1.3822(19) . ?
N2 C7 1.4794(19) . ?
N3 C23 1.4754(19) . ?
N3 C25 1.471(2) . ?
C2 C3 1.359(2) . ?
C3 H3 0.9500 . ?
C4 H4 1.0000 . ?
C4 C5 1.514(2) . ?
C4 C6 1.513(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7 1.0000 . ?
C7 C8 1.523(2) . ?
C7 C9 1.522(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 1.0000 . ?
C10 H10A 1.0000 . ?
C10 C17 1.521(2) . ?
C10 C11 1.543(7) . ?
C10 C11A 1.510(19) . ?
C17 C18 1.396(2) . ?
C17 C22 1.396(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.395(2) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.523(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.527(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C11 C12 1.400(5) . ?
C11 C16 1.395(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.398(6) . ?
C16 H16 0.9500 . ?
C11A C12A 1.380(14) . ?
C11A C16A 1.352(15) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.424(15) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.372(14) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.356(14) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.390(15) . ?
C16A H16A 0.9500 . ?
S2 C27 1.6947(16) . ?
P2 N6 1.6742(14) . ?
P2 C28 1.8425(16) . ?
P2 C36 1.8795(16) . ?
N4 C27 1.369(2) . ?
N4 C28 1.4092(19) . ?
N4 C30 1.481(2) . ?
N5 C27 1.3653(19) . ?
N5 C29 1.3804(19) . ?
N5 C33 1.4789(19) . ?
N6 C49 1.465(2) . ?
N6 C51 1.471(2) . ?
C28 C29 1.361(2) . ?
C29 H29 0.9500 . ?
C30 H30 1.0000 . ?
C30 C31 1.509(3) . ?
C30 C32 1.521(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33 1.0000 . ?
C33 C34 1.524(2) . ?
C33 C35 1.521(2) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36 1.0000 . ?
C36 C37 1.515(2) . ?
C36 C43 1.521(2) . ?
C37 C38 1.393(2) . ?
C37 C42 1.397(2) . ?
C38 H38 0.9500 . ?
C38 C39 1.388(2) . ?
C39 H39 0.9500 . ?
C39 C40 1.390(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.379(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.397(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.396(2) . ?
C43 C48 1.398(2) . ?
C44 H44 0.9500 . ?
C44 C45 1.394(2) . ?
C45 H45 0.9500 . ?
C45 C46 1.384(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.387(3) . ?
C47 H47 0.9500 . ?
C47 C48 1.393(2) . ?
C48 H48 0.9500 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C49 C50 1.526(2) . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C51 C52 1.518(3) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 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
N3 P1 C2 102.00(7) . . ?
N3 P1 C10 103.90(7) . . ?
C2 P1 C10 100.16(7) . . ?
C1 N1 C2 110.05(12) . . ?
C1 N1 C4 120.95(12) . . ?
C2 N1 C4 128.99(13) . . ?
C1 N2 C3 109.91(12) . . ?
C1 N2 C7 124.62(12) . . ?
C3 N2 C7 125.14(12) . . ?
C23 N3 P1 116.97(10) . . ?
C25 N3 P1 122.39(10) . . ?
C25 N3 C23 115.96(12) . . ?
N1 C1 S1 127.93(11) . . ?
N2 C1 S1 126.27(11) . . ?
N2 C1 N1 105.79(12) . . ?
N1 C2 P1 124.64(11) . . ?
C3 C2 P1 129.85(11) . . ?
C3 C2 N1 105.51(13) . . ?
N2 C3 H3 125.6 . . ?
C2 C3 N2 108.74(13) . . ?
C2 C3 H3 125.6 . . ?
N1 C4 H4 106.2 . . ?
N1 C4 C5 110.75(13) . . ?
N1 C4 C6 112.83(13) . . ?
C5 C4 H4 106.2 . . ?
C6 C4 H4 106.2 . . ?
C6 C4 C5 113.95(15) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7 108.5 . . ?
N2 C7 C8 110.78(12) . . ?
N2 C7 C9 108.88(12) . . ?
C8 C7 H7 108.5 . . ?
C9 C7 H7 108.5 . . ?
C9 C7 C8 111.69(13) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
P1 C10 H10 109.1 . . ?
P1 C10 H10A 104.7 . . ?
C17 C10 P1 114.08(11) . . ?
C17 C10 H10 109.1 . . ?
C17 C10 H10A 104.7 . . ?
C17 C10 C11 113.2(4) . . ?
C11 C10 P1 102.0(3) . . ?
C11 C10 H10 109.1 . . ?
C11A C10 P1 110.4(8) . . ?
C11A C10 H10A 104.7 . . ?
C11A C10 C17 116.8(9) . . ?
C18 C17 C10 122.76(14) . . ?
C22 C17 C10 119.29(14) . . ?
C22 C17 C18 117.93(15) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.16(16) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.26(18) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.41(16) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.76(17) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 H22 119.8 . . ?
C21 C22 C17 120.48(16) . . ?
C21 C22 H22 119.8 . . ?
N3 C23 H23A 108.8 . . ?
N3 C23 H23B 108.8 . . ?
N3 C23 C24 113.70(13) . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N3 C25 H25A 108.9 . . ?
N3 C25 H25B 108.9 . . ?
N3 C25 C26 113.46(13) . . ?
H25A C25 H25B 107.7 . . ?
C26 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C12 C11 C10 123.9(4) . . ?
C16 C11 C10 118.3(4) . . ?
C16 C11 C12 117.7(5) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C11 C16 C15 121.4(4) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C12A C11A C10 117.1(11) . . ?
C16A C11A C10 123.5(11) . . ?
C16A C11A C12A 119.3(14) . . ?
C11A C12A H12A 119.8 . . ?
C11A C12A C13A 120.5(11) . . ?
C13A C12A H12A 119.8 . . ?
C12A C13A H13A 121.1 . . ?
C14A C13A C12A 117.9(8) . . ?
C14A C13A H13A 121.1 . . ?
C13A C14A H14A 119.3 . . ?
C15A C14A C13A 121.4(9) . . ?
C15A C14A H14A 119.3 . . ?
C14A C15A H15A 120.1 . . ?
C14A C15A C16A 119.9(10) . . ?
C16A C15A H15A 120.1 . . ?
C11A C16A C15A 121.1(11) . . ?
C11A C16A H16A 119.4 . . ?
C15A C16A H16A 119.4 . . ?
N6 P2 C28 105.13(7) . . ?
N6 P2 C36 105.41(7) . . ?
C28 P2 C36 95.04(7) . . ?
C27 N4 C28 110.34(12) . . ?
C27 N4 C30 122.56(13) . . ?
C28 N4 C30 127.08(13) . . ?
C27 N5 C29 109.37(12) . . ?
C27 N5 C33 124.01(13) . . ?
C29 N5 C33 126.29(12) . . ?
C49 N6 P2 124.79(10) . . ?
C49 N6 C51 116.34(13) . . ?
C51 N6 P2 118.20(11) . . ?
N4 C27 S2 128.00(12) . . ?
N5 C27 S2 126.02(12) . . ?
N5 C27 N4 105.97(13) . . ?
N4 C28 P2 125.18(11) . . ?
C29 C28 P2 129.68(12) . . ?
C29 C28 N4 105.14(13) . . ?
N5 C29 H29 125.4 . . ?
C28 C29 N5 109.17(13) . . ?
C28 C29 H29 125.4 . . ?
N4 C30 H30 106.1 . . ?
N4 C30 C31 110.77(16) . . ?
N4 C30 C32 112.09(16) . . ?
C31 C30 H30 106.1 . . ?
C31 C30 C32 115.02(18) . . ?
C32 C30 H30 106.1 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N5 C33 H33 108.1 . . ?
N5 C33 C34 109.56(12) . . ?
N5 C33 C35 110.81(12) . . ?
C34 C33 H33 108.1 . . ?
C35 C33 H33 108.1 . . ?
C35 C33 C34 111.92(13) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
P2 C36 H36 107.9 . . ?
C37 C36 P2 110.38(10) . . ?
C37 C36 H36 107.9 . . ?
C37 C36 C43 114.60(12) . . ?
C43 C36 P2 107.99(10) . . ?
C43 C36 H36 107.9 . . ?
C38 C37 C36 118.63(13) . . ?
C38 C37 C42 118.41(14) . . ?
C42 C37 C36 122.95(14) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 C37 120.83(15) . . ?
C39 C38 H38 119.6 . . ?
C38 C39 H39 119.9 . . ?
C38 C39 C40 120.21(16) . . ?
C40 C39 H39 119.9 . . ?
C39 C40 H40 120.2 . . ?
C41 C40 C39 119.67(16) . . ?
C41 C40 H40 120.2 . . ?
C40 C41 H41 119.9 . . ?
C40 C41 C42 120.20(16) . . ?
C42 C41 H41 119.9 . . ?
C37 C42 H42 119.7 . . ?
C41 C42 C37 120.61(16) . . ?
C41 C42 H42 119.7 . . ?
C44 C43 C36 119.06(14) . . ?
C44 C43 C48 118.56(14) . . ?
C48 C43 C36 122.37(14) . . ?
C43 C44 H44 119.8 . . ?
C45 C44 C43 120.49(15) . . ?
C45 C44 H44 119.8 . . ?
C44 C45 H45 119.8 . . ?
C46 C45 C44 120.49(16) . . ?
C46 C45 H45 119.8 . . ?
C45 C46 H46 120.2 . . ?
C45 C46 C47 119.56(15) . . ?
C47 C46 H46 120.2 . . ?
C46 C47 H47 119.9 . . ?
C46 C47 C48 120.24(16) . . ?
C48 C47 H47 119.9 . . ?
C43 C48 H48 119.7 . . ?
C47 C48 C43 120.65(15) . . ?
C47 C48 H48 119.7 . . ?
N6 C49 H49A 109.0 . . ?
N6 C49 H49B 109.0 . . ?
N6 C49 C50 112.75(13) . . ?
H49A C49 H49B 107.8 . . ?
C50 C49 H49A 109.0 . . ?
C50 C49 H49B 109.0 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
N6 C51 H51A 109.0 . . ?
N6 C51 H51B 109.0 . . ?
N6 C51 C52 112.97(16) . . ?
H51A C51 H51B 107.8 . . ?
C52 C51 H51A 109.0 . . ?
C52 C51 H51B 109.0 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 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
P1 N3 C23 C24 140.15(13) . . . . ?
P1 N3 C25 C26 -100.83(15) . . . . ?
P1 C2 C3 N2 -179.60(11) . . . . ?
P1 C10 C17 C18 52.44(18) . . . . ?
P1 C10 C17 C22 -129.27(13) . . . . ?
P1 C10 C11 C12 -57.6(8) . . . . ?
P1 C10 C11 C16 118.4(7) . . . . ?
P1 C10 C11A C12A -59.5(18) . . . . ?
P1 C10 C11A C16A 116.6(18) . . . . ?
N1 C2 C3 N2 0.48(16) . . . . ?
N3 P1 C2 N1 88.43(13) . . . . ?
N3 P1 C2 C3 -91.48(15) . . . . ?
N3 P1 C10 C17 179.66(11) . . . . ?
N3 P1 C10 C11 -58.0(3) . . . . ?
N3 P1 C10 C11A -46.5(7) . . . . ?
C1 N1 C2 P1 -179.93(10) . . . . ?
C1 N1 C2 C3 0.00(16) . . . . ?
C1 N1 C4 C5 -105.36(16) . . . . ?
C1 N1 C4 C6 125.55(16) . . . . ?
C1 N2 C3 C2 -0.81(17) . . . . ?
C1 N2 C7 C8 137.57(15) . . . . ?
C1 N2 C7 C9 -99.24(16) . . . . ?
C2 P1 N3 C23 -154.59(11) . . . . ?
C2 P1 N3 C25 50.66(13) . . . . ?
C2 P1 C10 C17 74.47(12) . . . . ?
C2 P1 C10 C11 -163.2(3) . . . . ?
C2 P1 C10 C11A -151.7(7) . . . . ?
C2 N1 C1 S1 179.80(11) . . . . ?
C2 N1 C1 N2 -0.48(16) . . . . ?
C2 N1 C4 C5 73.4(2) . . . . ?
C2 N1 C4 C6 -55.7(2) . . . . ?
C3 N2 C1 S1 -179.49(11) . . . . ?
C3 N2 C1 N1 0.78(16) . . . . ?
C3 N2 C7 C8 -49.79(19) . . . . ?
C3 N2 C7 C9 73.41(17) . . . . ?
C4 N1 C1 S1 -1.2(2) . . . . ?
C4 N1 C1 N2 178.53(12) . . . . ?
C4 N1 C2 P1 1.2(2) . . . . ?
C4 N1 C2 C3 -178.90(14) . . . . ?
C7 N2 C1 S1 -5.9(2) . . . . ?
C7 N2 C1 N1 174.39(12) . . . . ?
C7 N2 C3 C2 -174.38(13) . . . . ?
C10 P1 N3 C23 101.62(12) . . . . ?
C10 P1 N3 C25 -53.13(13) . . . . ?
C10 P1 C2 N1 -164.86(12) . . . . ?
C10 P1 C2 C3 15.23(16) . . . . ?
C10 C17 C18 C19 177.99(15) . . . . ?
C10 C17 C22 C21 -177.99(14) . . . . ?
C10 C11 C12 C13 174.6(6) . . . . ?
C10 C11 C16 C15 -174.9(5) . . . . ?
C10 C11A C12A C13A 174.7(13) . . . . ?
C10 C11A C16A C15A -174.1(15) . . . . ?
C17 C10 C11 C12 65.4(8) . . . . ?
C17 C10 C11 C16 -118.6(7) . . . . ?
C17 C10 C11A C12A 73.0(18) . . . . ?
C17 C10 C11A C16A -111.0(19) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C18 C17 C22 C21 0.4(2) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C20 C21 C22 C17 -0.5(3) . . . . ?
C22 C17 C18 C19 -0.3(2) . . . . ?
C23 N3 C25 C26 104.19(16) . . . . ?
C25 N3 C23 C24 -63.46(19) . . . . ?
C11 C10 C17 C18 -63.6(3) . . . . ?
C11 C10 C17 C22 114.7(3) . . . . ?
C11 C12 C13 C14 0.0(8) . . . . ?
C12 C11 C16 C15 1.3(11) . . . . ?
C12 C13 C14 C15 1.6(6) . . . . ?
C13 C14 C15 C16 -1.7(6) . . . . ?
C14 C15 C16 C11 0.3(8) . . . . ?
C16 C11 C12 C13 -1.4(11) . . . . ?
C11A C10 C17 C18 -78.3(7) . . . . ?
C11A C10 C17 C22 100.0(7) . . . . ?
C11A C12A C13A C14A 0.9(19) . . . . ?
C12A C11A C16A C15A 2(3) . . . . ?
C12A C13A C14A C15A -0.7(17) . . . . ?
C13A C14A C15A C16A 1(2) . . . . ?
C14A C15A C16A C11A -2(2) . . . . ?
C16A C11A C12A C13A -1(3) . . . . ?
P2 N6 C49 C50 -96.02(15) . . . . ?
P2 N6 C51 C52 -117.11(17) . . . . ?
P2 C28 C29 N5 179.69(11) . . . . ?
P2 C36 C37 C38 112.30(14) . . . . ?
P2 C36 C37 C42 -68.76(17) . . . . ?
P2 C36 C43 C44 -134.39(13) . . . . ?
P2 C36 C43 C48 44.27(17) . . . . ?
N4 C28 C29 N5 -0.41(17) . . . . ?
N6 P2 C28 N4 105.47(14) . . . . ?
N6 P2 C28 C29 -74.64(16) . . . . ?
N6 P2 C36 C37 -54.97(12) . . . . ?
N6 P2 C36 C43 179.04(10) . . . . ?
C27 N4 C28 P2 179.82(11) . . . . ?
C27 N4 C28 C29 -0.09(17) . . . . ?
C27 N4 C30 C31 111.68(18) . . . . ?
C27 N4 C30 C32 -118.37(18) . . . . ?
C27 N5 C29 C28 0.78(17) . . . . ?
C27 N5 C33 C34 -78.56(18) . . . . ?
C27 N5 C33 C35 157.45(14) . . . . ?
C28 P2 N6 C49 39.17(14) . . . . ?
C28 P2 N6 C51 -131.10(13) . . . . ?
C28 P2 C36 C37 -162.19(11) . . . . ?
C28 P2 C36 C43 71.82(11) . . . . ?
C28 N4 C27 S2 -178.15(12) . . . . ?
C28 N4 C27 N5 0.55(17) . . . . ?
C28 N4 C30 C31 -66.5(2) . . . . ?
C28 N4 C30 C32 63.4(2) . . . . ?
C29 N5 C27 S2 177.93(12) . . . . ?
C29 N5 C27 N4 -0.80(16) . . . . ?
C29 N5 C33 C34 94.09(17) . . . . ?
C29 N5 C33 C35 -29.9(2) . . . . ?
C30 N4 C27 S2 3.4(2) . . . . ?
C30 N4 C27 N5 -177.94(14) . . . . ?
C30 N4 C28 P2 -1.8(2) . . . . ?
C30 N4 C28 C29 178.31(15) . . . . ?
C33 N5 C27 S2 -8.3(2) . . . . ?
C33 N5 C27 N4 172.92(13) . . . . ?
C33 N5 C29 C28 -172.77(13) . . . . ?
C36 P2 N6 C49 -60.55(14) . . . . ?
C36 P2 N6 C51 129.18(13) . . . . ?
C36 P2 C28 N4 -147.06(13) . . . . ?
C36 P2 C28 C29 32.82(16) . . . . ?
C36 C37 C38 C39 176.61(15) . . . . ?
C36 C37 C42 C41 -176.72(15) . . . . ?
C36 C43 C44 C45 178.41(14) . . . . ?
C36 C43 C48 C47 -178.46(15) . . . . ?
C37 C36 C43 C44 102.14(16) . . . . ?
C37 C36 C43 C48 -79.19(18) . . . . ?
C37 C38 C39 C40 0.5(3) . . . . ?
C38 C37 C42 C41 2.2(2) . . . . ?
C38 C39 C40 C41 1.6(3) . . . . ?
C39 C40 C41 C42 -1.8(3) . . . . ?
C40 C41 C42 C37 -0.2(3) . . . . ?
C42 C37 C38 C39 -2.4(2) . . . . ?
C43 C36 C37 C38 -125.53(15) . . . . ?
C43 C36 C37 C42 53.4(2) . . . . ?
C43 C44 C45 C46 -0.1(2) . . . . ?
C44 C43 C48 C47 0.2(2) . . . . ?
C44 C45 C46 C47 0.7(3) . . . . ?
C45 C46 C47 C48 -0.8(3) . . . . ?
C46 C47 C48 C43 0.3(3) . . . . ?
C48 C43 C44 C45 -0.3(2) . . . . ?
C49 N6 C51 C52 71.8(2) . . . . ?
C51 N6 C49 C50 74.41(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


_vrf_PLAT230_4a                  
;
PROBLEM: Hirshfeld Test Diff for    C30    --  C32     ..        7.4 s.u.  
RESPONSE: There is mild thermal motion evident in this i-Pr group,
however attempts at modeling this thermal motion as disorder failed.
;
####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1550751'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;
_audit_creation_date             2016-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ABK-344
_chemical_formula_moiety         '2(C H2 Cl2), C38 H42 N3 P S'
_chemical_formula_sum            'C40 H46 Cl4 N3 P S'
_chemical_formula_weight         773.63
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   20.390(2)
_cell_length_b                   14.3808(14)
_cell_length_c                   27.503(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.164(3)
_cell_angle_gamma                90
_cell_volume                     8031.8(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7382
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.80
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.418
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4315
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1597 before and 0.0709 after correction.
The Ratio of minimum to maximum transmission is 0.5785.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3248
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 0.938
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21514
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.245
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_min         1.487
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'Bruker X8-KappaApexII'
_diffrn_measurement_method       'fine slicing ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5392
_reflns_number_total             6815
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.213
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         6815
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0706
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1494P)²+22.2540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2011
_refine_ls_wR_factor_ref         0.2393
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C22, C23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Ternary CH refined with riding coordinates:
 C22(H22)
3.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C40(H40A,H40B), C35(H35A,H35B), C37(H37A,H37B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C8(H8), C15(H15), C17(H17), C27(H27), C28(H28), C29(H29),
 C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C36(H36A,H36B,H36C), C38(H38A,
 H38B,H38C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.40690(9) 0.86142(12) -0.23029(7) 0.0715(6) Uani 1 1 d . . . . .
Cl2 Cl 0.38170(10) 0.66703(10) -0.25421(5) 0.0609(5) Uani 1 1 d . . . . .
C39 C 0.3597(3) 0.7827(4) -0.2682(2) 0.0567(17) Uani 1 1 d . . . . .
H39A H 0.3124 0.7918 -0.2641 0.068 Uiso 1 1 calc R . . . .
H39B H 0.3666 0.7955 -0.3028 0.068 Uiso 1 1 calc R . . . .
Cl3 Cl 0.72456(7) 1.09461(11) 0.06874(5) 0.0538(4) Uani 1 1 d . . . . .
Cl4 Cl 0.75503(8) 1.14527(14) 0.17075(6) 0.0697(6) Uani 1 1 d . . . . .
C40 C 0.6995(3) 1.0877(4) 0.1282(2) 0.0527(15) Uani 1 1 d . . . . .
H40A H 0.6553 1.1160 0.1287 0.063 Uiso 1 1 calc R . . . .
H40B H 0.6963 1.0216 0.1377 0.063 Uiso 1 1 calc R . . . .
S S 0.71293(5) 0.82291(7) 0.16485(4) 0.0231(3) Uani 1 1 d . . . . .
P P 0.49350(5) 0.72447(6) 0.04280(3) 0.0143(3) Uani 1 1 d . . . . .
N1 N 0.60222(16) 0.78191(19) 0.10494(11) 0.0154(7) Uani 1 1 d . . . . .
N2 N 0.66101(16) 0.6611(2) 0.12624(11) 0.0160(7) Uani 1 1 d . . . . .
N3 N 0.43497(17) 0.7037(2) 0.08004(12) 0.0178(7) Uani 1 1 d . . . . .
C1 C 0.5690(2) 0.7048(2) 0.08240(13) 0.0169(8) Uani 1 1 d . . . . .
C2 C 0.6579(2) 0.7558(3) 0.13203(13) 0.0182(8) Uani 1 1 d . . . . .
C3 C 0.6068(2) 0.6301(2) 0.09628(13) 0.0183(8) Uani 1 1 d . . . . .
H3 H 0.5978 0.5674 0.0871 0.022 Uiso 1 1 calc R . . . .
C4 C 0.57483(19) 0.8753(2) 0.10432(14) 0.0160(8) Uani 1 1 d . . . . .
C5 C 0.5824(2) 0.9316(3) 0.06381(14) 0.0197(8) Uani 1 1 d . . . . .
C6 C 0.5530(2) 1.0190(3) 0.06335(15) 0.0223(9) Uani 1 1 d . . . . .
H6 H 0.5557 1.0580 0.0357 0.027 Uiso 1 1 calc R . . . .
C7 C 0.5200(2) 1.0507(2) 0.10168(15) 0.0237(9) Uani 1 1 d . . . . .
C8 C 0.5143(2) 0.9926(3) 0.14157(15) 0.0213(9) Uani 1 1 d . . . . .
H8 H 0.4916 1.0142 0.1681 0.026 Uiso 1 1 calc R . . . .
C9 C 0.54120(19) 0.9036(2) 0.14345(14) 0.0176(8) Uani 1 1 d . . . . .
C10 C 0.6205(2) 0.8995(3) 0.02280(15) 0.0266(10) Uani 1 1 d . . . . .
H10A H 0.6643 0.8787 0.0359 0.040 Uiso 1 1 calc GR . . . .
H10B H 0.6249 0.9510 0.0000 0.040 Uiso 1 1 calc GR . . . .
H10C H 0.5972 0.8479 0.0056 0.040 Uiso 1 1 calc GR . . . .
C11 C 0.4906(2) 1.1473(3) 0.10133(19) 0.0343(11) Uani 1 1 d . . . . .
H11A H 0.5192 1.1881 0.1224 0.051 Uiso 1 1 calc GR . . . .
H11B H 0.4469 1.1446 0.1134 0.051 Uiso 1 1 calc GR . . . .
H11C H 0.4868 1.1717 0.0679 0.051 Uiso 1 1 calc GR . . . .
C12 C 0.5327(2) 0.8404(3) 0.18569(14) 0.0222(9) Uani 1 1 d . . . . .
H12A H 0.5006 0.7919 0.1756 0.033 Uiso 1 1 calc GR . . . .
H12B H 0.5169 0.8764 0.2126 0.033 Uiso 1 1 calc GR . . . .
H12C H 0.5750 0.8115 0.1966 0.033 Uiso 1 1 calc GR . . . .
C13 C 0.7114(2) 0.6015(2) 0.14910(14) 0.0182(8) Uani 1 1 d . . . . .
C14 C 0.7005(2) 0.5607(3) 0.19378(14) 0.0207(9) Uani 1 1 d . . . . .
C15 C 0.7485(2) 0.5001(3) 0.21449(15) 0.0241(9) Uani 1 1 d . . . . .
H15 H 0.7424 0.4714 0.2449 0.029 Uiso 1 1 calc R . . . .
C16 C 0.8053(2) 0.4807(3) 0.19153(14) 0.0231(9) Uani 1 1 d . . . . .
C17 C 0.8153(2) 0.5251(3) 0.14795(15) 0.0229(9) Uani 1 1 d . . . . .
H17 H 0.8548 0.5138 0.1330 0.028 Uiso 1 1 calc R . . . .
C18 C 0.7687(2) 0.5859(3) 0.12571(14) 0.0198(8) Uani 1 1 d . . . . .
C19 C 0.6391(2) 0.5802(3) 0.21808(16) 0.0291(10) Uani 1 1 d . . . . .
H19A H 0.6349 0.6474 0.2229 0.044 Uiso 1 1 calc GR . . . .
H19B H 0.6415 0.5486 0.2498 0.044 Uiso 1 1 calc GR . . . .
H19C H 0.6008 0.5574 0.1974 0.044 Uiso 1 1 calc GR . . . .
C20 C 0.8559(2) 0.4135(3) 0.21460(17) 0.0351(11) Uani 1 1 d . . . . .
H20A H 0.8734 0.4372 0.2466 0.053 Uiso 1 1 calc GR . . . .
H20B H 0.8920 0.4070 0.1935 0.053 Uiso 1 1 calc GR . . . .
H20C H 0.8353 0.3528 0.2186 0.053 Uiso 1 1 calc GR . . . .
C21 C 0.7786(2) 0.6319(3) 0.07779(15) 0.0272(10) Uani 1 1 d . . . . .
H21A H 0.7518 0.6003 0.0514 0.041 Uiso 1 1 calc GR . . . .
H21B H 0.8252 0.6281 0.0717 0.041 Uiso 1 1 calc GR . . . .
H21C H 0.7654 0.6973 0.0790 0.041 Uiso 1 1 calc GR . . . .
C22 C 0.49587(19) 0.6166(2) 0.00430(13) 0.0162(7) Uani 1 1 d . U . . .
H22 H 0.5016 0.5594 0.0249 0.019 Uiso 1 1 calc R . . . .
C23 C 0.54700(19) 0.6222(2) -0.03221(14) 0.0159(7) Uani 1 1 d . U . . .
C24 C 0.5160(2) 0.6266(2) -0.08006(14) 0.0179(8) Uani 1 1 d . . . . .
C25 C 0.4446(2) 0.6237(2) -0.07742(14) 0.0174(8) Uani 1 1 d . . . . .
C26 C 0.4321(2) 0.6138(2) -0.02855(14) 0.0178(8) Uani 1 1 d . . . . .
C27 C 0.6155(2) 0.6217(3) -0.02527(15) 0.0213(9) Uani 1 1 d . . . . .
H27 H 0.6368 0.6185 0.0068 0.026 Uiso 1 1 calc R . . . .
C28 C 0.6532(2) 0.6258(3) -0.06545(16) 0.0253(9) Uani 1 1 d . . . . .
H28 H 0.6999 0.6252 -0.0606 0.030 Uiso 1 1 calc R . . . .
C29 C 0.6213(2) 0.6307(3) -0.11287(15) 0.0246(9) Uani 1 1 d . . . . .
H29 H 0.6467 0.6338 -0.1401 0.030 Uiso 1 1 calc R . . . .
C30 C 0.5531(2) 0.6310(2) -0.12017(15) 0.0247(10) Uani 1 1 d . . . . .
H30 H 0.5317 0.6341 -0.1523 0.030 Uiso 1 1 calc R . . . .
C31 C 0.3936(2) 0.6283(3) -0.11459(15) 0.0250(9) Uani 1 1 d . . . . .
H31 H 0.4026 0.6353 -0.1477 0.030 Uiso 1 1 calc R . . . .
C32 C 0.3286(2) 0.6222(3) -0.10196(17) 0.0293(10) Uani 1 1 d . . . . .
H32 H 0.2930 0.6257 -0.1267 0.035 Uiso 1 1 calc R . . . .
C33 C 0.3159(2) 0.6113(3) -0.05368(17) 0.0290(10) Uani 1 1 d . . . . .
H33 H 0.2716 0.6067 -0.0459 0.035 Uiso 1 1 calc R . . . .
C34 C 0.3666(2) 0.6069(3) -0.01642(16) 0.0228(9) Uani 1 1 d . . . . .
H34 H 0.3572 0.5995 0.0166 0.027 Uiso 1 1 calc R . . . .
C35 C 0.3814(2) 0.7700(3) 0.08634(16) 0.0273(10) Uani 1 1 d . . . . .
H35A H 0.3844 0.7898 0.1209 0.033 Uiso 1 1 calc R . . . .
H35B H 0.3388 0.7374 0.0793 0.033 Uiso 1 1 calc R . . . .
C36 C 0.3815(2) 0.8557(3) 0.05451(17) 0.0268(10) Uani 1 1 d . . . . .
H36A H 0.3770 0.8373 0.0201 0.040 Uiso 1 1 calc GR . . . .
H36B H 0.4230 0.8895 0.0617 0.040 Uiso 1 1 calc GR . . . .
H36C H 0.3446 0.8960 0.0611 0.040 Uiso 1 1 calc GR . . . .
C37 C 0.4278(2) 0.6157(3) 0.10652(14) 0.0238(9) Uani 1 1 d . . . . .
H37A H 0.4580 0.5694 0.0940 0.029 Uiso 1 1 calc R . . . .
H37B H 0.3824 0.5926 0.0987 0.029 Uiso 1 1 calc R . . . .
C38 C 0.4413(2) 0.6199(3) 0.16134(16) 0.0305(10) Uani 1 1 d . . . . .
H38A H 0.4875 0.6362 0.1699 0.046 Uiso 1 1 calc GR . . . .
H38B H 0.4320 0.5591 0.1754 0.046 Uiso 1 1 calc GR . . . .
H38C H 0.4129 0.6671 0.1744 0.046 Uiso 1 1 calc GR . . . .


_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 C39 1.765(5) . ?
Cl2 C39 1.756(6) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
Cl3 C40 1.761(6) . ?
Cl4 C40 1.760(5) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
S C2 1.681(4) . ?
P N3 1.668(4) . ?
P C1 1.825(4) . ?
P C22 1.881(4) . ?
N1 C1 1.413(4) . ?
N1 C2 1.353(5) . ?
N1 C4 1.454(4) . ?
N2 C2 1.373(5) . ?
N2 C3 1.391(5) . ?
N2 C13 1.438(5) . ?
N3 C35 1.471(5) . ?
N3 C37 1.474(5) . ?
C1 C3 1.358(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(5) . ?
C4 C9 1.388(6) . ?
C5 C6 1.393(5) . ?
C5 C10 1.498(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.378(6) . ?
C7 C8 1.391(6) . ?
C7 C11 1.512(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(5) . ?
C9 C12 1.498(5) . ?
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 1.398(6) . ?
C13 C18 1.401(6) . ?
C14 C15 1.393(5) . ?
C14 C19 1.497(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.396(6) . ?
C16 C17 1.389(6) . ?
C16 C20 1.512(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(6) . ?
C18 C21 1.505(6) . ?
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 H22 1.0000 . ?
C22 C23 1.513(6) . ?
C22 C26 1.515(5) . ?
C23 C24 1.409(5) . ?
C23 C27 1.392(6) . ?
C24 C25 1.465(6) . ?
C24 C30 1.393(6) . ?
C25 C26 1.398(5) . ?
C25 C31 1.393(5) . ?
C26 C34 1.410(6) . ?
C27 H27 0.9500 . ?
C27 C28 1.402(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.405(6) . ?
C29 H29 0.9500 . ?
C29 C30 1.388(6) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C31 C32 1.403(7) . ?
C32 H32 0.9500 . ?
C32 C33 1.385(7) . ?
C33 H33 0.9500 . ?
C33 C34 1.390(6) . ?
C34 H34 0.9500 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.513(6) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C38 1.509(6) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 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
Cl1 C39 H39A 109.4 . . ?
Cl1 C39 H39B 109.4 . . ?
Cl2 C39 Cl1 111.3(3) . . ?
Cl2 C39 H39A 109.4 . . ?
Cl2 C39 H39B 109.4 . . ?
H39A C39 H39B 108.0 . . ?
Cl3 C40 H40A 109.3 . . ?
Cl3 C40 H40B 109.3 . . ?
Cl4 C40 Cl3 111.6(3) . . ?
Cl4 C40 H40A 109.3 . . ?
Cl4 C40 H40B 109.3 . . ?
H40A C40 H40B 108.0 . . ?
N3 P C1 102.55(18) . . ?
N3 P C22 104.70(16) . . ?
C1 P C22 98.36(16) . . ?
C1 N1 C4 123.4(3) . . ?
C2 N1 C1 111.6(3) . . ?
C2 N1 C4 124.4(3) . . ?
C2 N2 C3 110.1(3) . . ?
C2 N2 C13 125.4(3) . . ?
C3 N2 C13 124.5(3) . . ?
C35 N3 P 122.4(3) . . ?
C35 N3 C37 113.0(3) . . ?
C37 N3 P 124.4(3) . . ?
N1 C1 P 119.1(2) . . ?
C3 C1 P 135.9(3) . . ?
C3 C1 N1 105.0(3) . . ?
N1 C2 S 128.5(3) . . ?
N1 C2 N2 104.9(3) . . ?
N2 C2 S 126.6(3) . . ?
N2 C3 H3 125.8 . . ?
C1 C3 N2 108.3(3) . . ?
C1 C3 H3 125.8 . . ?
C5 C4 N1 118.3(3) . . ?
C9 C4 N1 118.5(3) . . ?
C9 C4 C5 123.1(3) . . ?
C4 C5 C10 121.7(3) . . ?
C6 C5 C4 116.8(4) . . ?
C6 C5 C10 121.5(4) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 C5 122.1(4) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C8 119.1(3) . . ?
C6 C7 C11 121.3(4) . . ?
C8 C7 C11 119.7(4) . . ?
C7 C8 H8 119.3 . . ?
C7 C8 C9 121.4(4) . . ?
C9 C8 H8 119.3 . . ?
C4 C9 C8 117.5(4) . . ?
C4 C9 C12 121.5(3) . . ?
C8 C9 C12 121.0(4) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N2 118.0(4) . . ?
C14 C13 C18 122.8(3) . . ?
C18 C13 N2 119.2(3) . . ?
C13 C14 C19 121.3(3) . . ?
C15 C14 C13 117.4(4) . . ?
C15 C14 C19 121.3(4) . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.4(4) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C20 120.1(4) . . ?
C17 C16 C15 119.4(4) . . ?
C17 C16 C20 120.5(4) . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.4(4) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 C21 121.0(3) . . ?
C17 C18 C13 117.6(4) . . ?
C17 C18 C21 121.4(4) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
P C22 H22 111.5 . . ?
C23 C22 P 112.6(2) . . ?
C23 C22 H22 111.5 . . ?
C23 C22 C26 102.2(3) . . ?
C26 C22 P 107.1(2) . . ?
C26 C22 H22 111.5 . . ?
C24 C23 C22 110.1(3) . . ?
C27 C23 C22 130.6(3) . . ?
C27 C23 C24 119.2(4) . . ?
C23 C24 C25 108.4(3) . . ?
C30 C24 C23 120.8(4) . . ?
C30 C24 C25 130.7(4) . . ?
C26 C25 C24 108.6(3) . . ?
C31 C25 C24 130.0(4) . . ?
C31 C25 C26 121.4(4) . . ?
C25 C26 C22 110.5(3) . . ?
C25 C26 C34 119.6(3) . . ?
C34 C26 C22 129.9(4) . . ?
C23 C27 H27 119.8 . . ?
C23 C27 C28 120.4(4) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 120.2 . . ?
C27 C28 C29 119.6(4) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.5(4) . . ?
C30 C29 H29 119.7 . . ?
C24 C30 H30 120.2 . . ?
C29 C30 C24 119.5(4) . . ?
C29 C30 H30 120.2 . . ?
C25 C31 H31 120.8 . . ?
C25 C31 C32 118.4(4) . . ?
C32 C31 H31 120.8 . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.4(4) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 119.3 . . ?
C32 C33 C34 121.4(4) . . ?
C34 C33 H33 119.3 . . ?
C26 C34 H34 120.6 . . ?
C33 C34 C26 118.7(4) . . ?
C33 C34 H34 120.6 . . ?
N3 C35 H35A 108.5 . . ?
N3 C35 H35B 108.5 . . ?
N3 C35 C36 114.9(4) . . ?
H35A C35 H35B 107.5 . . ?
C36 C35 H35A 108.5 . . ?
C36 C35 H35B 108.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N3 C37 H37A 108.2 . . ?
N3 C37 H37B 108.2 . . ?
N3 C37 C38 116.2(3) . . ?
H37A C37 H37B 107.4 . . ?
C38 C37 H37A 108.2 . . ?
C38 C37 H37B 108.2 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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
P N3 C35 C36 3.1(5) . . . . ?
P N3 C37 C38 112.3(4) . . . . ?
P C1 C3 N2 177.4(3) . . . . ?
P C22 C23 C24 -112.0(3) . . . . ?
P C22 C23 C27 69.4(4) . . . . ?
P C22 C26 C25 114.5(3) . . . . ?
P C22 C26 C34 -62.7(4) . . . . ?
N1 C1 C3 N2 0.1(5) . . . . ?
N1 C4 C5 C6 177.1(3) . . . . ?
N1 C4 C5 C10 -3.0(5) . . . . ?
N1 C4 C9 C8 -178.7(3) . . . . ?
N1 C4 C9 C12 -0.1(5) . . . . ?
N2 C13 C14 C15 177.4(3) . . . . ?
N2 C13 C14 C19 -1.8(6) . . . . ?
N2 C13 C18 C17 -177.6(3) . . . . ?
N2 C13 C18 C21 1.3(5) . . . . ?
N3 P C1 N1 -97.2(3) . . . . ?
N3 P C1 C3 85.7(5) . . . . ?
N3 P C22 C23 -179.8(2) . . . . ?
N3 P C22 C26 68.7(3) . . . . ?
C1 P N3 C35 128.1(3) . . . . ?
C1 P N3 C37 -57.3(3) . . . . ?
C1 P C22 C23 -74.4(3) . . . . ?
C1 P C22 C26 174.1(3) . . . . ?
C1 N1 C2 S 179.6(3) . . . . ?
C1 N1 C2 N2 0.9(4) . . . . ?
C1 N1 C4 C5 -84.2(5) . . . . ?
C1 N1 C4 C9 94.4(4) . . . . ?
C2 N1 C1 P -178.5(3) . . . . ?
C2 N1 C1 C3 -0.6(5) . . . . ?
C2 N1 C4 C5 104.7(4) . . . . ?
C2 N1 C4 C9 -76.7(5) . . . . ?
C2 N2 C3 C1 0.5(5) . . . . ?
C2 N2 C13 C14 92.4(5) . . . . ?
C2 N2 C13 C18 -88.4(5) . . . . ?
C3 N2 C2 S -179.6(3) . . . . ?
C3 N2 C2 N1 -0.9(4) . . . . ?
C3 N2 C13 C14 -85.2(5) . . . . ?
C3 N2 C13 C18 94.1(5) . . . . ?
C4 N1 C1 P 9.4(5) . . . . ?
C4 N1 C1 C3 -172.7(4) . . . . ?
C4 N1 C2 S -8.4(6) . . . . ?
C4 N1 C2 N2 172.9(3) . . . . ?
C4 C5 C6 C7 2.5(6) . . . . ?
C5 C4 C9 C8 -0.2(6) . . . . ?
C5 C4 C9 C12 178.5(3) . . . . ?
C5 C6 C7 C8 -1.8(6) . . . . ?
C5 C6 C7 C11 177.6(4) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
C7 C8 C9 C4 1.0(6) . . . . ?
C7 C8 C9 C12 -177.7(4) . . . . ?
C9 C4 C5 C6 -1.5(5) . . . . ?
C9 C4 C5 C10 178.4(4) . . . . ?
C10 C5 C6 C7 -177.5(4) . . . . ?
C11 C7 C8 C9 -179.4(4) . . . . ?
C13 N2 C2 S 2.5(6) . . . . ?
C13 N2 C2 N1 -178.7(4) . . . . ?
C13 N2 C3 C1 178.4(4) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C14 C13 C18 C17 1.6(6) . . . . ?
C14 C13 C18 C21 -179.5(4) . . . . ?
C14 C15 C16 C17 2.2(6) . . . . ?
C14 C15 C16 C20 -179.1(4) . . . . ?
C15 C16 C17 C18 -2.5(6) . . . . ?
C16 C17 C18 C13 0.6(6) . . . . ?
C16 C17 C18 C21 -178.3(4) . . . . ?
C18 C13 C14 C15 -1.8(6) . . . . ?
C18 C13 C14 C19 179.0(4) . . . . ?
C19 C14 C15 C16 179.1(4) . . . . ?
C20 C16 C17 C18 178.8(4) . . . . ?
C22 P N3 C35 -129.7(3) . . . . ?
C22 P N3 C37 45.0(3) . . . . ?
C22 P C1 N1 155.6(3) . . . . ?
C22 P C1 C3 -21.4(5) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C22 C23 C24 C30 -179.2(3) . . . . ?
C22 C23 C27 C28 178.7(3) . . . . ?
C22 C26 C34 C33 176.2(4) . . . . ?
C23 C22 C26 C25 -4.0(4) . . . . ?
C23 C22 C26 C34 178.8(4) . . . . ?
C23 C24 C25 C26 -2.3(4) . . . . ?
C23 C24 C25 C31 178.3(4) . . . . ?
C23 C24 C30 C29 0.2(5) . . . . ?
C23 C27 C28 C29 0.2(6) . . . . ?
C24 C23 C27 C28 0.2(5) . . . . ?
C24 C25 C26 C22 4.0(4) . . . . ?
C24 C25 C26 C34 -178.4(3) . . . . ?
C24 C25 C31 C32 178.9(4) . . . . ?
C25 C24 C30 C29 -178.4(4) . . . . ?
C25 C26 C34 C33 -0.8(5) . . . . ?
C25 C31 C32 C33 -0.5(6) . . . . ?
C26 C22 C23 C24 2.5(4) . . . . ?
C26 C22 C23 C27 -176.1(4) . . . . ?
C26 C25 C31 C32 -0.3(5) . . . . ?
C27 C23 C24 C25 178.5(3) . . . . ?
C27 C23 C24 C30 -0.4(5) . . . . ?
C27 C28 C29 C30 -0.4(6) . . . . ?
C28 C29 C30 C24 0.2(5) . . . . ?
C30 C24 C25 C26 176.4(4) . . . . ?
C30 C24 C25 C31 -2.9(6) . . . . ?
C31 C25 C26 C22 -176.6(3) . . . . ?
C31 C25 C26 C34 1.0(5) . . . . ?
C31 C32 C33 C34 0.7(6) . . . . ?
C32 C33 C34 C26 0.0(6) . . . . ?
C35 N3 C37 C38 -72.6(5) . . . . ?
C37 N3 C35 C36 -172.1(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1550750'
_audit_update_record             
;
2017-06-30 deposited with the CCDC.
2017-07-18 downloaded from the CCDC.
;
_audit_creation_date             2015-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        ABK-247
_chemical_formula_moiety         'C11 H21 Cl N3 P S'
_chemical_formula_sum            'C11 H21 Cl N3 P S'
_chemical_formula_weight         293.79
_chemical_melting_point          ?
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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.6794(7)
_cell_length_b                   9.3892(6)
_cell_length_c                   14.5557(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.915(3)
_cell_angle_gamma                90
_cell_volume                     1491.01(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9772
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.99
_cell_measurement_theta_min      4.05
_shelx_estimated_absorpt_T_max   0.842
_shelx_estimated_absorpt_T_min   0.640
_exptl_absorpt_coefficient_mu    4.456
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3776
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1494 before and 0.1038 after correction.
The Ratio of minimum to maximum transmission is 0.5011.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0872
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20754
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.744
_diffrn_reflns_theta_min         4.052
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon100 detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8-Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2325
_reflns_number_total             2693
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2693
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0638P)²+1.8511P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1214
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cl Cl 0.50979(5) 0.23287(6) 0.53486(5) 0.01579(19) Uani 1 1 d . . . . .
S S 0.73252(6) 0.73109(7) 0.30650(5) 0.0163(2) Uani 1 1 d . . . . .
P P 0.66836(6) 0.36471(6) 0.58216(5) 0.01130(19) Uani 1 1 d . . . . .
N1 N 0.71749(19) 0.5499(2) 0.44982(16) 0.0129(5) Uani 1 1 d . . . . .
N2 N 0.56855(19) 0.5263(2) 0.31052(16) 0.0120(5) Uani 1 1 d . . . . .
N3 N 0.78568(19) 0.2579(2) 0.59515(16) 0.0107(4) Uani 1 1 d . . . . .
C1 C 0.6415(2) 0.4414(3) 0.46203(19) 0.0117(5) Uani 1 1 d . . . . .
C2 C 0.6725(2) 0.6021(3) 0.35616(19) 0.0122(5) Uani 1 1 d . . . . .
C3 C 0.5482(2) 0.4294(3) 0.37413(18) 0.0115(5) Uani 1 1 d . . . . .
H3 H 0.4808 0.3656 0.3591 0.014 Uiso 1 1 calc R . . . .
C4 C 0.8240(2) 0.6086(3) 0.5273(2) 0.0189(6) Uani 1 1 d . . . . .
H4A H 0.8881 0.5357 0.5497 0.028 Uiso 1 1 calc GR . . . .
H4B H 0.8006 0.6389 0.5825 0.028 Uiso 1 1 calc GR . . . .
H4C H 0.8551 0.6906 0.5017 0.028 Uiso 1 1 calc GR . . . .
C5 C 0.4861(2) 0.5505(3) 0.2094(2) 0.0181(6) Uani 1 1 d . . . . .
H5A H 0.4404 0.6391 0.2061 0.027 Uiso 1 1 calc GR . . . .
H5B H 0.4285 0.4707 0.1880 0.027 Uiso 1 1 calc GR . . . .
H5C H 0.5339 0.5579 0.1664 0.027 Uiso 1 1 calc GR . . . .
C6 C 0.8669(2) 0.2213(3) 0.69793(18) 0.0137(5) Uani 1 1 d . . . . .
H6 H 0.9240 0.1449 0.6928 0.016 Uiso 1 1 calc R . . . .
C7 C 0.9457(3) 0.3485(3) 0.7474(2) 0.0199(6) Uani 1 1 d . . . . .
H7A H 0.8929 0.4264 0.7532 0.030 Uiso 1 1 calc GR . . . .
H7B H 0.9935 0.3800 0.7078 0.030 Uiso 1 1 calc GR . . . .
H7C H 1.0016 0.3209 0.8130 0.030 Uiso 1 1 calc GR . . . .
C8 C 0.7954(3) 0.1603(3) 0.7582(2) 0.0221(6) Uani 1 1 d . . . . .
H8A H 0.7460 0.0794 0.7232 0.033 Uiso 1 1 calc GR . . . .
H8B H 0.7413 0.2339 0.7681 0.033 Uiso 1 1 calc GR . . . .
H8C H 0.8527 0.1284 0.8222 0.033 Uiso 1 1 calc GR . . . .
C9 C 0.7954(2) 0.1636(3) 0.51641(19) 0.0138(5) Uani 1 1 d . . . . .
H9 H 0.7335 0.1977 0.4530 0.017 Uiso 1 1 calc R . . . .
C10 C 0.9210(3) 0.1792(3) 0.5076(2) 0.0228(6) Uani 1 1 d . . . . .
H10A H 0.9843 0.1447 0.5679 0.034 Uiso 1 1 calc GR . . . .
H10B H 0.9360 0.2798 0.4976 0.034 Uiso 1 1 calc GR . . . .
H10C H 0.9234 0.1233 0.4514 0.034 Uiso 1 1 calc GR . . . .
C11 C 0.7641(3) 0.0086(3) 0.5293(2) 0.0215(6) Uani 1 1 d . . . . .
H11A H 0.6812 0.0035 0.5314 0.032 Uiso 1 1 calc GR . . . .
H11B H 0.8230 -0.0288 0.5909 0.032 Uiso 1 1 calc GR . . . .
H11C H 0.7679 -0.0481 0.4740 0.032 Uiso 1 1 calc GR . . . .


_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
Cl P 2.1274(9) . ?
S C2 1.686(3) . ?
P N3 1.654(2) . ?
P C1 1.812(3) . ?
N1 C1 1.404(3) . ?
N1 C2 1.365(3) . ?
N1 C4 1.457(3) . ?
N2 C2 1.359(3) . ?
N2 C3 1.378(3) . ?
N2 C5 1.460(3) . ?
N3 C6 1.498(3) . ?
N3 C9 1.484(3) . ?
C1 C3 1.357(4) . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 1.0000 . ?
C6 C7 1.523(4) . ?
C6 C8 1.524(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9 1.0000 . ?
C9 C10 1.525(4) . ?
C9 C11 1.528(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
N3 P Cl 105.90(8) . . ?
N3 P C1 101.69(11) . . ?
C1 P Cl 95.04(8) . . ?
C1 N1 C4 125.5(2) . . ?
C2 N1 C1 110.6(2) . . ?
C2 N1 C4 123.7(2) . . ?
C2 N2 C3 110.8(2) . . ?
C2 N2 C5 124.3(2) . . ?
C3 N2 C5 124.7(2) . . ?
C6 N3 P 117.20(17) . . ?
C9 N3 P 124.20(17) . . ?
C9 N3 C6 116.03(19) . . ?
N1 C1 P 120.73(18) . . ?
C3 C1 P 133.0(2) . . ?
C3 C1 N1 105.8(2) . . ?
N1 C2 S 128.0(2) . . ?
N2 C2 S 127.0(2) . . ?
N2 C2 N1 105.0(2) . . ?
N2 C3 H3 126.1 . . ?
C1 C3 N2 107.8(2) . . ?
C1 C3 H3 126.1 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 H6 106.9 . . ?
N3 C6 C7 110.7(2) . . ?
N3 C6 C8 112.3(2) . . ?
C7 C6 H6 106.9 . . ?
C7 C6 C8 112.7(2) . . ?
C8 C6 H6 106.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9 107.0 . . ?
N3 C9 C10 110.4(2) . . ?
N3 C9 C11 112.7(2) . . ?
C10 C9 H9 107.0 . . ?
C10 C9 C11 112.5(2) . . ?
C11 C9 H9 107.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
Cl P N3 C6 -105.78(17) . . . . ?
Cl P N3 C9 55.3(2) . . . . ?
Cl P C1 N1 175.26(18) . . . . ?
Cl P C1 C3 5.0(3) . . . . ?
P N3 C6 C7 -72.8(3) . . . . ?
P N3 C6 C8 54.1(3) . . . . ?
P N3 C9 C10 132.0(2) . . . . ?
P N3 C9 C11 -101.3(2) . . . . ?
P C1 C3 N2 172.2(2) . . . . ?
N1 C1 C3 N2 0.9(3) . . . . ?
N3 P C1 N1 -77.3(2) . . . . ?
N3 P C1 C3 112.4(3) . . . . ?
C1 P N3 C6 155.46(18) . . . . ?
C1 P N3 C9 -43.5(2) . . . . ?
C1 N1 C2 S -179.25(19) . . . . ?
C1 N1 C2 N2 0.2(3) . . . . ?
C2 N1 C1 P -173.32(17) . . . . ?
C2 N1 C1 C3 -0.7(3) . . . . ?
C2 N2 C3 C1 -0.8(3) . . . . ?
C3 N2 C2 S 179.84(19) . . . . ?
C3 N2 C2 N1 0.4(3) . . . . ?
C4 N1 C1 P 1.8(3) . . . . ?
C4 N1 C1 C3 174.5(2) . . . . ?
C4 N1 C2 S 5.5(4) . . . . ?
C4 N1 C2 N2 -175.1(2) . . . . ?
C5 N2 C2 S -3.5(4) . . . . ?
C5 N2 C2 N1 177.0(2) . . . . ?
C5 N2 C3 C1 -177.5(2) . . . . ?
C6 N3 C9 C10 -66.8(3) . . . . ?
C6 N3 C9 C11 59.9(3) . . . . ?
C9 N3 C6 C7 124.6(2) . . . . ?
C9 N3 C6 C8 -108.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
