# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_5a_123K
_database_code_depnum_ccdc_archive 'CCDC 1935843'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2019-06-21 deposited with the CCDC.	2019-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C25 H38 N O4 P S'
_chemical_formula_sum            'C25 H38 N O4 P S'
_chemical_formula_weight         479.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   10.6790(7)
_cell_length_b                   12.0178(8)
_cell_length_c                   11.2241(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.3257(14)
_cell_angle_gamma                90
_cell_volume                     1332.50(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    123.0(1)
_cell_measurement_reflns_used    9829
_cell_measurement_theta_min      4.48
_cell_measurement_theta_max      79.52

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.655
_exptl_crystal_size_mid          0.634
_exptl_crystal_size_min          0.502
_exptl_absorpt_coefficient_mu    1.878
_shelx_estimated_absorpt_T_min   0.373
_shelx_estimated_absorpt_T_max   0.452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5780
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'

_diffrn_ambient_temperature      123.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Cu)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_detector                 CPAD
_diffrn_detector_type            'PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            31499
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.476
_diffrn_reflns_theta_max         80.528
_diffrn_reflns_theta_full        67.750
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5643
_reflns_number_gt                5614
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_max     0.935
_reflns_Friedel_fraction_full    0.980

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+0.3540P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_extinction_coef       0.0090(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5643
_refine_ls_number_parameters     300
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0711
_refine_ls_wR_factor_gt          0.0709
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.41881(19) 0.38371(15) 0.40046(18) 0.0152(4) Uani 1 1 d . . . . .
C2A C 0.3751(2) 0.28034(16) 0.42858(19) 0.0168(4) Uani 1 1 d . . . . .
C3A C 0.2465(2) 0.26928(18) 0.4312(2) 0.0213(4) Uani 1 1 d . . . . .
H3A H 0.218040 0.199447 0.451745 0.026 Uiso 1 1 calc R U . . .
C4A C 0.1599(2) 0.35956(19) 0.4041(2) 0.0239(4) Uani 1 1 d . . . . .
H4A H 0.072753 0.351695 0.407441 0.029 Uiso 1 1 calc R U . . .
C5A C 0.1995(2) 0.46222(18) 0.3718(2) 0.0229(4) Uani 1 1 d . . . . .
H5A H 0.138828 0.523534 0.350545 0.027 Uiso 1 1 calc R U . . .
C6A C 0.3280(2) 0.47370(17) 0.3711(2) 0.0185(4) Uani 1 1 d . . . . .
H6A H 0.355480 0.543830 0.350431 0.022 Uiso 1 1 calc R U . . .
C7A C 0.5948(2) 0.38324(18) 0.25108(19) 0.0202(4) Uani 1 1 d . . . . .
C8A C 0.5527(3) 0.2626(2) 0.2126(2) 0.0287(5) Uani 1 1 d . . . . .
H8AA H 0.616599 0.212184 0.275158 0.043 Uiso 1 1 calc R U . . .
H8AB H 0.553112 0.248197 0.126832 0.043 Uiso 1 1 calc R U . . .
H8AC H 0.461531 0.250034 0.211328 0.043 Uiso 1 1 calc R U . . .
C9A C 0.7405(2) 0.4033(3) 0.2608(2) 0.0318(5) Uani 1 1 d . . . . .
H9AA H 0.767656 0.479587 0.289914 0.048 Uiso 1 1 calc R U . . .
H9AB H 0.745186 0.392174 0.176067 0.048 Uiso 1 1 calc R U . . .
H9AC H 0.801603 0.350777 0.322548 0.048 Uiso 1 1 calc R U . . .
C10A C 0.4981(3) 0.4637(2) 0.1529(2) 0.0337(5) Uani 1 1 d . . . . .
H10A H 0.406736 0.455006 0.152553 0.051 Uiso 1 1 calc R U . . .
H10B H 0.496876 0.447195 0.066957 0.051 Uiso 1 1 calc R U . . .
H10C H 0.528948 0.540343 0.176452 0.051 Uiso 1 1 calc R U . . .
C11A C 0.85410(19) 0.43200(16) 0.73077(18) 0.0161(4) Uani 1 1 d . . . . .
C12A C 0.76156(19) 0.43636(17) 0.79319(18) 0.0182(4) Uani 1 1 d . . . . .
C13A C 0.7763(2) 0.52172(18) 0.8817(2) 0.0216(4) Uani 1 1 d . . . . .
H13A H 0.713589 0.526116 0.923068 0.026 Uiso 1 1 calc R U . . .
C14A C 0.8788(2) 0.60058(17) 0.91193(18) 0.0207(4) Uani 1 1 d . . . . .
C15A C 0.9702(2) 0.59086(18) 0.85229(19) 0.0197(4) Uani 1 1 d . . . . .
H15A H 1.041240 0.643902 0.872932 0.024 Uiso 1 1 calc R U . . .
C16A C 0.96416(19) 0.50782(17) 0.76366(18) 0.0163(4) Uani 1 1 d . . . . .
C17A C 0.6507(2) 0.35051(19) 0.7783(2) 0.0232(4) Uani 1 1 d . . . . .
H17A H 0.640828 0.302542 0.702419 0.028 Uiso 1 1 calc R U . . .
C18A C 0.6936(3) 0.2761(2) 0.8977(2) 0.0360(6) Uani 1 1 d . . . . .
H18A H 0.775770 0.235157 0.905776 0.054 Uiso 1 1 calc R U . . .
H18B H 0.620852 0.223232 0.889482 0.054 Uiso 1 1 calc R U . . .
H18C H 0.711562 0.322193 0.974500 0.054 Uiso 1 1 calc R U . . .
C19A C 0.5139(2) 0.4058(3) 0.7531(3) 0.0365(6) Uani 1 1 d . . . . .
H19A H 0.517773 0.445653 0.830587 0.055 Uiso 1 1 calc R U . . .
H19B H 0.443189 0.348731 0.731167 0.055 Uiso 1 1 calc R U . . .
H19C H 0.493260 0.458400 0.681451 0.055 Uiso 1 1 calc R U . . .
C20A C 0.8984(2) 0.6940(2) 1.0095(2) 0.0259(5) Uani 1 1 d . . . . .
H20A H 0.993753 0.688423 1.073355 0.031 Uiso 1 1 calc R U . . .
C21A C 0.8076(3) 0.6868(2) 1.0850(3) 0.0372(6) Uani 1 1 d . . . . .
H21A H 0.712909 0.694381 1.026032 0.056 Uiso 1 1 calc R U . . .
H21B H 0.830588 0.746642 1.149006 0.056 Uiso 1 1 calc R U . . .
H21C H 0.820498 0.614646 1.128747 0.056 Uiso 1 1 calc R U . . .
C22A C 0.8847(3) 0.8073(2) 0.9439(2) 0.0320(5) Uani 1 1 d . . . . .
H22A H 0.948966 0.812063 0.900773 0.048 Uiso 1 1 calc R U . . .
H22B H 0.904032 0.866360 1.008570 0.048 Uiso 1 1 calc R U . . .
H22C H 0.792282 0.816054 0.880121 0.048 Uiso 1 1 calc R U . . .
C23A C 1.07994(19) 0.50643(18) 0.7146(2) 0.0195(4) Uani 1 1 d . . . . .
H23A H 1.087252 0.429158 0.684787 0.023 Uiso 1 1 calc R U . . .
C24A C 1.2169(2) 0.5368(2) 0.8203(3) 0.0330(5) Uani 1 1 d . . . . .
H24A H 1.218402 0.616435 0.839515 0.050 Uiso 1 1 calc R U . . .
H24B H 1.289870 0.519543 0.790446 0.050 Uiso 1 1 calc R U . . .
H24C H 1.229740 0.493770 0.898200 0.050 Uiso 1 1 calc R U . . .
C25A C 1.0494(3) 0.5845(2) 0.5995(2) 0.0300(5) Uani 1 1 d . . . . .
H25A H 0.963806 0.562676 0.531200 0.045 Uiso 1 1 calc R U . . .
H25B H 1.122624 0.579769 0.567240 0.045 Uiso 1 1 calc R U . . .
H25C H 1.042357 0.661036 0.626361 0.045 Uiso 1 1 calc R U . . .
N1A N 0.68142(15) 0.31941(15) 0.51465(14) 0.0159(3) Uani 1 1 d . . . . .
H1A H 0.638553 0.256893 0.514731 0.019 Uiso 1 1 calc R U . . .
O1A O 0.63112(15) 0.52930(12) 0.44856(15) 0.0205(3) Uani 1 1 d . . . . .
O2A O 0.46090(14) 0.19143(12) 0.45534(15) 0.0210(3) Uani 1 1 d . . . . .
H2A H 0.425123 0.136895 0.477052 0.031 Uiso 1 1 calc R U . . .
O3A O 0.92344(15) 0.34247(15) 0.55048(16) 0.0300(4) Uani 1 1 d . . . . .
O4A O 0.85266(17) 0.21831(13) 0.68745(16) 0.0279(4) Uani 1 1 d . . . . .
P1A P 0.58683(4) 0.41335(4) 0.40733(4) 0.01350(12) Uani 1 1 d . . . . .
S1A S 0.83854(4) 0.32165(4) 0.61953(4) 0.01665(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C2A 1.405(3) . ?
C1A C6A 1.406(3) . ?
C1A P1A 1.802(2) . ?
C2A O2A 1.365(2) . ?
C2A C3A 1.392(3) . ?
C3A C4A 1.382(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.396(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.382(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.531(3) . ?
C7A C10A 1.533(3) . ?
C7A C9A 1.537(3) . ?
C7A P1A 1.824(2) . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C11A C12A 1.413(3) . ?
C11A C16A 1.421(3) . ?
C11A S1A 1.785(2) . ?
C12A C13A 1.395(3) . ?
C12A C17A 1.531(3) . ?
C13A C14A 1.389(3) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.382(3) . ?
C14A C20A 1.526(3) . ?
C15A C16A 1.393(3) . ?
C15A H15A 0.9500 . ?
C16A C23A 1.533(3) . ?
C17A C19A 1.530(3) . ?
C17A C18A 1.530(3) . ?
C17A H17A 1.0000 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C20A C21A 1.513(3) . ?
C20A C22A 1.529(3) . ?
C20A H20A 1.0000 . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
C23A C25A 1.528(3) . ?
C23A C24A 1.537(3) . ?
C23A H23A 1.0000 . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
C25A H25A 0.9800 . ?
C25A H25B 0.9800 . ?
C25A H25C 0.9800 . ?
N1A S1A 1.6435(15) . ?
N1A P1A 1.6797(17) . ?
N1A H1A 0.8800 . ?
O1A P1A 1.4877(14) . ?
O2A H2A 0.8400 . ?
O3A S1A 1.4209(15) . ?
O4A S1A 1.4350(16) . ?

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
C2A C1A C6A 118.31(17) . . ?
C2A C1A P1A 125.16(14) . . ?
C6A C1A P1A 116.44(15) . . ?
O2A C2A C3A 120.41(18) . . ?
O2A C2A C1A 119.29(17) . . ?
C3A C2A C1A 120.29(18) . . ?
C4A C3A C2A 120.2(2) . . ?
C4A C3A H3A 119.9 . . ?
C2A C3A H3A 119.9 . . ?
C3A C4A C5A 120.49(19) . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A H4A 119.8 . . ?
C6A C5A C4A 119.29(19) . . ?
C6A C5A H5A 120.4 . . ?
C4A C5A H5A 120.4 . . ?
C5A C6A C1A 121.35(18) . . ?
C5A C6A H6A 119.3 . . ?
C1A C6A H6A 119.3 . . ?
C8A C7A C10A 110.45(19) . . ?
C8A C7A C9A 110.44(19) . . ?
C10A C7A C9A 109.84(19) . . ?
C8A C7A P1A 110.05(15) . . ?
C10A C7A P1A 107.53(15) . . ?
C9A C7A P1A 108.46(15) . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C7A C9A H9AA 109.5 . . ?
C7A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
C7A C9A H9AC 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C7A C10A H10A 109.5 . . ?
C7A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C7A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C12A C11A C16A 120.85(17) . . ?
C12A C11A S1A 118.52(14) . . ?
C16A C11A S1A 120.41(14) . . ?
C13A C12A C11A 118.01(18) . . ?
C13A C12A C17A 116.54(17) . . ?
C11A C12A C17A 125.33(17) . . ?
C14A C13A C12A 122.73(19) . . ?
C14A C13A H13A 118.6 . . ?
C12A C13A H13A 118.6 . . ?
C15A C14A C13A 117.39(19) . . ?
C15A C14A C20A 118.71(19) . . ?
C13A C14A C20A 123.86(19) . . ?
C14A C15A C16A 123.85(19) . . ?
C14A C15A H15A 118.1 . . ?
C16A C15A H15A 118.1 . . ?
C15A C16A C11A 117.01(17) . . ?
C15A C16A C23A 116.09(17) . . ?
C11A C16A C23A 126.88(17) . . ?
C19A C17A C18A 111.2(2) . . ?
C19A C17A C12A 111.8(2) . . ?
C18A C17A C12A 109.67(18) . . ?
C19A C17A H17A 108.0 . . ?
C18A C17A H17A 108.0 . . ?
C12A C17A H17A 108.0 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C17A C19A H19A 109.5 . . ?
C17A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C17A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C21A C20A C14A 114.7(2) . . ?
C21A C20A C22A 110.9(2) . . ?
C14A C20A C22A 110.30(18) . . ?
C21A C20A H20A 106.8 . . ?
C14A C20A H20A 106.8 . . ?
C22A C20A H20A 106.8 . . ?
C20A C21A H21A 109.5 . . ?
C20A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C20A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C20A C22A H22A 109.5 . . ?
C20A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C20A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C25A C23A C16A 110.80(16) . . ?
C25A C23A C24A 109.97(19) . . ?
C16A C23A C24A 112.39(17) . . ?
C25A C23A H23A 107.8 . . ?
C16A C23A H23A 107.8 . . ?
C24A C23A H23A 107.8 . . ?
C23A C24A H24A 109.5 . . ?
C23A C24A H24B 109.5 . . ?
H24A C24A H24B 109.5 . . ?
C23A C24A H24C 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
C23A C25A H25A 109.5 . . ?
C23A C25A H25B 109.5 . . ?
H25A C25A H25B 109.5 . . ?
C23A C25A H25C 109.5 . . ?
H25A C25A H25C 109.5 . . ?
H25B C25A H25C 109.5 . . ?
S1A N1A P1A 132.44(11) . . ?
S1A N1A H1A 113.8 . . ?
P1A N1A H1A 113.8 . . ?
C2A O2A H2A 109.5 . . ?
O1A P1A N1A 111.89(9) . . ?
O1A P1A C1A 113.09(8) . . ?
N1A P1A C1A 102.45(8) . . ?
O1A P1A C7A 111.06(9) . . ?
N1A P1A C7A 108.73(9) . . ?
C1A P1A C7A 109.21(9) . . ?
O3A S1A O4A 118.82(11) . . ?
O3A S1A N1A 107.55(9) . . ?
O4A S1A N1A 103.83(9) . . ?
O3A S1A C11A 109.96(9) . . ?
O4A S1A C11A 107.95(9) . . ?
N1A S1A C11A 108.16(9) . . ?

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
C6A C1A C2A O2A 178.99(17) . . . . ?
P1A C1A C2A O2A -4.6(3) . . . . ?
C6A C1A C2A C3A -2.1(3) . . . . ?
P1A C1A C2A C3A 174.29(16) . . . . ?
O2A C2A C3A C4A 180.0(2) . . . . ?
C1A C2A C3A C4A 1.1(3) . . . . ?
C2A C3A C4A C5A 1.0(3) . . . . ?
C3A C4A C5A C6A -2.0(4) . . . . ?
C4A C5A C6A C1A 0.9(3) . . . . ?
C2A C1A C6A C5A 1.1(3) . . . . ?
P1A C1A C6A C5A -175.61(17) . . . . ?
C16A C11A C12A C13A 4.1(3) . . . . ?
S1A C11A C12A C13A 178.81(15) . . . . ?
C16A C11A C12A C17A -171.80(19) . . . . ?
S1A C11A C12A C17A 2.9(3) . . . . ?
C11A C12A C13A C14A -1.1(3) . . . . ?
C17A C12A C13A C14A 175.22(19) . . . . ?
C12A C13A C14A C15A -1.3(3) . . . . ?
C12A C13A C14A C20A -179.2(2) . . . . ?
C13A C14A C15A C16A 0.6(3) . . . . ?
C20A C14A C15A C16A 178.69(19) . . . . ?
C14A C15A C16A C11A 2.3(3) . . . . ?
C14A C15A C16A C23A -176.18(19) . . . . ?
C12A C11A C16A C15A -4.7(3) . . . . ?
S1A C11A C16A C15A -179.25(14) . . . . ?
C12A C11A C16A C23A 173.59(18) . . . . ?
S1A C11A C16A C23A -1.0(3) . . . . ?
C13A C12A C17A C19A 51.9(3) . . . . ?
C11A C12A C17A C19A -132.1(2) . . . . ?
C13A C12A C17A C18A -72.0(3) . . . . ?
C11A C12A C17A C18A 104.0(2) . . . . ?
C15A C14A C20A C21A -170.6(2) . . . . ?
C13A C14A C20A C21A 7.3(3) . . . . ?
C15A C14A C20A C22A 63.4(3) . . . . ?
C13A C14A C20A C22A -118.7(2) . . . . ?
C15A C16A C23A C25A -86.2(2) . . . . ?
C11A C16A C23A C25A 95.5(2) . . . . ?
C15A C16A C23A C24A 37.2(3) . . . . ?
C11A C16A C23A C24A -141.0(2) . . . . ?
S1A N1A P1A O1A -27.52(16) . . . . ?
S1A N1A P1A C1A -148.96(13) . . . . ?
S1A N1A P1A C7A 95.53(15) . . . . ?
C2A C1A P1A O1A -146.37(16) . . . . ?
C6A C1A P1A O1A 30.07(18) . . . . ?
C2A C1A P1A N1A -25.76(18) . . . . ?
C6A C1A P1A N1A 150.69(15) . . . . ?
C2A C1A P1A C7A 89.41(18) . . . . ?
C6A C1A P1A C7A -94.15(16) . . . . ?
C8A C7A P1A O1A 178.37(14) . . . . ?
C10A C7A P1A O1A -61.28(18) . . . . ?
C9A C7A P1A O1A 57.46(18) . . . . ?
C8A C7A P1A N1A 54.83(16) . . . . ?
C10A C7A P1A N1A 175.18(16) . . . . ?
C9A C7A P1A N1A -66.09(18) . . . . ?
C8A C7A P1A C1A -56.23(16) . . . . ?
C10A C7A P1A C1A 64.12(18) . . . . ?
C9A C7A P1A C1A -177.14(16) . . . . ?
P1A N1A S1A O3A -57.46(16) . . . . ?
P1A N1A S1A O4A 175.77(13) . . . . ?
P1A N1A S1A C11A 61.26(15) . . . . ?
C12A C11A S1A O3A 169.61(15) . . . . ?
C16A C11A S1A O3A -15.70(19) . . . . ?
C12A C11A S1A O4A -59.33(17) . . . . ?
C16A C11A S1A O4A 115.36(17) . . . . ?
C12A C11A S1A N1A 52.43(17) . . . . ?
C16A C11A S1A N1A -132.88(15) . . . . ?

_refine_diff_density_max         0.346
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.036


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_compound_source        dichloromethane/pentane
####################################################################### 
# 
# 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_5c_253K
_database_code_depnum_ccdc_archive 'CCDC 1935844'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2019-06-24 deposited with the CCDC.	2019-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C29 H40 N O4 P S, C H4 O'
_chemical_formula_sum            'C30 H44 N O5 P S'
_chemical_formula_weight         561.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   10.5840(6)
_cell_length_b                   15.7917(8)
_cell_length_c                   18.4493(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3083.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    253.0(1)
_cell_measurement_reflns_used    9491
_cell_measurement_theta_min      3.68
_cell_measurement_theta_max      72.54

_exptl_crystal_description       lath
_exptl_crystal_colour            yellow
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.644
_exptl_crystal_size_mid          0.628
_exptl_crystal_size_min          0.384
_exptl_absorpt_coefficient_mu    1.721
_shelx_estimated_absorpt_T_min   0.404
_shelx_estimated_absorpt_T_max   0.558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6107
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'

_diffrn_ambient_temperature      253.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Cu)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_detector                 CPAD
_diffrn_detector_type            'PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            60068
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.684
_diffrn_reflns_theta_max         72.806
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             6006
_reflns_number_gt                5965
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.984

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+2.5741P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_extinction_coef       0.0130(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2577 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6006
_refine_ls_number_parameters     483
_refine_ls_number_restraints     981
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.4858(3) 0.2608(2) 0.1870(2) 0.0351(8) Uani 1 1 d . . . . .
C2A C 0.5386(4) 0.3330(3) 0.2157(2) 0.0424(9) Uani 1 1 d . . . . .
C3A C 0.6714(4) 0.3419(3) 0.2206(3) 0.0592(13) Uani 1 1 d . . . . .
H3A H 0.705388 0.391332 0.239775 0.071 Uiso 1 1 calc R U . . .
C4A C 0.7487(4) 0.2805(4) 0.1981(3) 0.0619(13) Uani 1 1 d . . . . .
H4A H 0.835585 0.287908 0.202208 0.074 Uiso 1 1 calc R U . . .
C5A C 0.7013(4) 0.2045(3) 0.1682(2) 0.0479(10) Uani 1 1 d . . . . .
C6A C 0.7844(5) 0.1396(4) 0.1455(3) 0.0592(13) Uani 1 1 d . . . . .
H6A H 0.871121 0.147180 0.150497 0.071 Uiso 1 1 calc R U . . .
C7A C 0.7403(6) 0.0670(4) 0.1167(3) 0.0662(15) Uani 1 1 d . . . . .
H7A H 0.795652 0.023784 0.103749 0.079 Uiso 1 1 calc R U . . .
C8A C 0.6101(6) 0.0575(3) 0.1066(3) 0.0615(13) Uani 1 1 d . . . . .
H8A H 0.579789 0.008211 0.085145 0.074 Uiso 1 1 calc R U . . .
C9A C 0.5260(5) 0.1190(3) 0.1274(3) 0.0504(11) Uani 1 1 d . . . . .
H9A H 0.440023 0.110965 0.119418 0.060 Uiso 1 1 calc R U . . .
C10A C 0.5681(4) 0.1941(3) 0.1607(2) 0.0385(9) Uani 1 1 d . . . . .
C11A C 0.2570(4) 0.2946(3) 0.1001(2) 0.0408(9) Uani 1 1 d . . . . .
C12A C 0.2863(6) 0.3892(3) 0.0992(3) 0.0594(13) Uani 1 1 d . . . . .
H12A H 0.375938 0.397488 0.102671 0.089 Uiso 1 1 calc R U . . .
H12B H 0.245451 0.416094 0.139590 0.089 Uiso 1 1 calc R U . . .
H12C H 0.255881 0.413602 0.054855 0.089 Uiso 1 1 calc R U . . .
C13A C 0.1135(5) 0.2816(4) 0.0956(3) 0.0671(15) Uani 1 1 d . . . . .
H13A H 0.083181 0.301849 0.049759 0.101 Uiso 1 1 calc R U . . .
H13B H 0.073150 0.312487 0.134046 0.101 Uiso 1 1 calc R U . . .
H13C H 0.094406 0.222463 0.100371 0.101 Uiso 1 1 calc R U . . .
C14A C 0.3237(6) 0.2522(4) 0.0369(2) 0.0686(15) Uani 1 1 d . . . . .
H14A H 0.297910 0.278436 -0.007639 0.103 Uiso 1 1 calc R U . . .
H14B H 0.302048 0.193142 0.035772 0.103 Uiso 1 1 calc R U . . .
H14C H 0.413471 0.258065 0.042572 0.103 Uiso 1 1 calc R U . . .
C15A C 0.1770(4) 0.2006(3) 0.3654(2) 0.0292(8) Uani 0.904(7) 1 d D U P A 1
C16A C 0.2612(4) 0.2224(3) 0.4219(2) 0.0327(9) Uani 0.904(7) 1 d D U P A 1
C17A C 0.2901(5) 0.1598(3) 0.4725(3) 0.0415(11) Uani 0.904(7) 1 d D U P A 1
H17A H 0.345421 0.172987 0.509974 0.050 Uiso 0.904(7) 1 calc R U P A 1
C18A C 0.2401(5) 0.0790(3) 0.4695(3) 0.0433(11) Uani 0.904(7) 1 d D U P A 1
C19A C 0.1602(5) 0.0599(3) 0.4127(3) 0.0413(11) Uani 0.904(7) 1 d D U P A 1
H19A H 0.127287 0.005422 0.409904 0.050 Uiso 0.904(7) 1 calc R U P A 1
C20A C 0.1260(4) 0.1181(3) 0.3592(2) 0.0321(9) Uani 0.904(7) 1 d D U P A 1
C21A C 0.3226(5) 0.3081(3) 0.4346(3) 0.0429(11) Uani 0.904(7) 1 d D U P A 1
H21A H 0.312664 0.341463 0.390134 0.051 Uiso 0.904(7) 1 calc R U P A 1
C22A C 0.2533(7) 0.3549(3) 0.4956(3) 0.0655(17) Uani 0.904(7) 1 d D U P A 1
H22A H 0.164824 0.358018 0.484440 0.098 Uiso 0.904(7) 1 calc R U P A 1
H22B H 0.264688 0.324798 0.540383 0.098 Uiso 0.904(7) 1 calc R U P A 1
H22C H 0.286940 0.411054 0.500304 0.098 Uiso 0.904(7) 1 calc R U P A 1
C23A C 0.4628(6) 0.3022(4) 0.4509(5) 0.078(2) Uani 0.904(7) 1 d D U P A 1
H23A H 0.496315 0.358026 0.458388 0.116 Uiso 0.904(7) 1 calc R U P A 1
H23B H 0.475442 0.268881 0.493807 0.116 Uiso 0.904(7) 1 calc R U P A 1
H23C H 0.505481 0.275994 0.410824 0.116 Uiso 0.904(7) 1 calc R U P A 1
C24A C 0.2750(6) 0.0113(4) 0.5243(3) 0.0597(15) Uani 0.904(7) 1 d D U P A 1
H24A H 0.213201 -0.034447 0.518802 0.072 Uiso 0.904(7) 1 calc R U P A 1
C25A C 0.2653(10) 0.0417(5) 0.6009(3) 0.090(2) Uani 0.904(7) 1 d D U P A 1
H25A H 0.288225 -0.003267 0.633285 0.136 Uiso 0.904(7) 1 calc R U P A 1
H25B H 0.321352 0.088823 0.607872 0.136 Uiso 0.904(7) 1 calc R U P A 1
H25C H 0.180075 0.059176 0.610610 0.136 Uiso 0.904(7) 1 calc R U P A 1
C26A C 0.4042(8) -0.0264(6) 0.5070(6) 0.117(4) Uani 0.904(7) 1 d D U P A 1
H26A H 0.405706 -0.044902 0.457426 0.175 Uiso 0.904(7) 1 calc R U P A 1
H26B H 0.468283 0.015782 0.514290 0.175 Uiso 0.904(7) 1 calc R U P A 1
H26C H 0.419907 -0.073746 0.538323 0.175 Uiso 0.904(7) 1 calc R U P A 1
C27A C 0.0346(4) 0.0870(3) 0.3005(3) 0.0389(10) Uani 0.904(7) 1 d D U P A 1
H27A H 0.048960 0.121176 0.256915 0.047 Uiso 0.904(7) 1 calc R U P A 1
C28A C -0.1017(5) 0.1027(4) 0.3257(3) 0.0524(14) Uani 0.904(7) 1 d D U P A 1
H28A H -0.111827 0.161302 0.338210 0.079 Uiso 0.904(7) 1 calc R U P A 1
H28B H -0.159052 0.088382 0.287314 0.079 Uiso 0.904(7) 1 calc R U P A 1
H28C H -0.119279 0.068169 0.367316 0.079 Uiso 0.904(7) 1 calc R U P A 1
C29A C 0.0538(8) -0.0057(4) 0.2802(4) 0.0679(19) Uani 0.904(7) 1 d D U P A 1
H29A H -0.005889 -0.021406 0.243384 0.102 Uiso 0.904(7) 1 calc R U P A 1
H29B H 0.138097 -0.013617 0.262164 0.102 Uiso 0.904(7) 1 calc R U P A 1
H29C H 0.041357 -0.040577 0.322228 0.102 Uiso 0.904(7) 1 calc R U P A 1
O3A O 0.0354(3) 0.2555(3) 0.2575(2) 0.0474(10) Uani 0.904(7) 1 d D U P A 1
O4A O 0.1123(4) 0.3589(2) 0.3458(2) 0.0424(9) Uani 0.904(7) 1 d D U P A 1
S1A S 0.13326(16) 0.28339(12) 0.30491(11) 0.0301(4) Uani 0.904(7) 1 d D U P A 1
N1A N 0.2594(3) 0.3036(2) 0.25440(16) 0.0338(7) Uani 1 1 d D U . . .
H1A H 0.301176 0.348556 0.265172 0.041 Uiso 0.904(7) 1 calc R U P A 1
H1B H 0.297371 0.351544 0.257951 0.041 Uiso 0.096(7) 1 calc R U P A 2
O1A O 0.2755(2) 0.15653(16) 0.19321(16) 0.0399(6) Uani 1 1 d . . . . .
O2A O 0.4647(3) 0.39752(19) 0.2405(2) 0.0519(8) Uani 1 1 d . . . . .
H2A H 0.503766 0.442249 0.237622 0.078 Uiso 1 1 calc R U . . .
P1A P 0.31489(8) 0.24598(6) 0.18431(5) 0.0300(2) Uani 1 1 d . . . . .
S1B S 0.161(2) 0.2930(12) 0.3118(11) 0.050(5) Uani 0.096(7) 1 d G U P A 2
O3B O 0.047(2) 0.2788(16) 0.2737(14) 0.046(6) Uani 0.096(7) 1 d G U P A 2
O4B O 0.169(3) 0.3663(11) 0.3567(14) 0.052(7) Uani 0.096(7) 1 d G U P A 2
C15B C 0.2018(19) 0.2022(10) 0.3644(10) 0.036(5) Uani 0.096(7) 1 d G U P A 2
C16B C 0.304(2) 0.2111(13) 0.4128(11) 0.041(5) Uani 0.096(7) 1 d DG U P A 2
C17B C 0.332(3) 0.1428(15) 0.4578(13) 0.044(6) Uani 0.096(7) 1 d G U P A 2
H17B H 0.399672 0.147646 0.489874 0.053 Uiso 0.096(7) 1 calc R U P A 2
C18B C 0.264(3) 0.0682(14) 0.4570(15) 0.049(5) Uani 0.096(7) 1 d DG U P A 2
C19B C 0.166(3) 0.0616(11) 0.4081(15) 0.043(6) Uani 0.096(7) 1 d G U P A 2
H19B H 0.119851 0.011423 0.406940 0.051 Uiso 0.096(7) 1 calc R U P A 2
C20B C 0.131(2) 0.1263(11) 0.3603(13) 0.039(5) Uani 0.096(7) 1 d DG U P A 2
C21B C 0.388(3) 0.2886(16) 0.4223(15) 0.054(6) Uani 0.096(7) 1 d DG U P A 2
H21B H 0.364060 0.327507 0.383216 0.065 Uiso 0.096(7) 1 calc R U P A 2
C24B C 0.298(4) -0.0063(17) 0.5052(19) 0.078(6) Uani 0.096(7) 1 d DG U P A 2
H24B H 0.218915 -0.038419 0.509104 0.094 Uiso 0.096(7) 1 calc R U P A 2
C27B C 0.018(3) 0.1095(16) 0.3106(17) 0.048(6) Uani 0.096(7) 1 d DG U P A 2
H27B H 0.000332 0.155717 0.276638 0.058 Uiso 0.096(7) 1 calc R U P A 2
C28B C -0.097(3) 0.082(5) 0.354(3) 0.058(8) Uani 0.096(7) 1 d D U P A 2
H28D H -0.125130 0.127825 0.384130 0.087 Uiso 0.096(7) 1 calc R U P A 2
H28E H -0.163327 0.065185 0.321958 0.087 Uiso 0.096(7) 1 calc R U P A 2
H28F H -0.074262 0.034593 0.384599 0.087 Uiso 0.096(7) 1 calc R U P A 2
C29B C 0.029(6) 0.023(3) 0.275(4) 0.058(8) Uani 0.096(7) 1 d D U P A 2
H29D H 0.098948 0.023119 0.241810 0.087 Uiso 0.096(7) 1 calc R U P A 2
H29E H 0.041437 -0.019452 0.311121 0.087 Uiso 0.096(7) 1 calc R U P A 2
H29F H -0.047627 0.011141 0.248480 0.087 Uiso 0.096(7) 1 calc R U P A 2
C22B C 0.355(6) 0.334(3) 0.493(2) 0.065(7) Uani 0.096(7) 1 d D U P A 2
H22D H 0.408035 0.383113 0.498150 0.098 Uiso 0.096(7) 1 calc R U P A 2
H22E H 0.267932 0.351890 0.491366 0.098 Uiso 0.096(7) 1 calc R U P A 2
H22F H 0.367468 0.296737 0.532971 0.098 Uiso 0.096(7) 1 calc R U P A 2
C23B C 0.525(3) 0.265(3) 0.408(4) 0.075(9) Uani 0.096(7) 1 d D U P A 2
H23D H 0.577835 0.313870 0.413964 0.112 Uiso 0.096(7) 1 calc R U P A 2
H23E H 0.551071 0.221671 0.441467 0.112 Uiso 0.096(7) 1 calc R U P A 2
H23F H 0.533533 0.243936 0.359274 0.112 Uiso 0.096(7) 1 calc R U P A 2
C25B C 0.323(8) 0.024(3) 0.582(2) 0.082(7) Uani 0.096(7) 1 d D U P A 2
H25D H 0.344364 -0.023827 0.612415 0.123 Uiso 0.096(7) 1 calc R U P A 2
H25E H 0.392002 0.063365 0.582359 0.123 Uiso 0.096(7) 1 calc R U P A 2
H25F H 0.248814 0.050907 0.601304 0.123 Uiso 0.096(7) 1 calc R U P A 2
C26B C 0.388(9) -0.067(4) 0.467(4) 0.098(10) Uani 0.096(7) 1 d D U P A 2
H26D H 0.407590 -0.113299 0.498617 0.147 Uiso 0.096(7) 1 calc R U P A 2
H26E H 0.348529 -0.088121 0.423732 0.147 Uiso 0.096(7) 1 calc R U P A 2
H26F H 0.464126 -0.037453 0.454417 0.147 Uiso 0.096(7) 1 calc R U P A 2
C1S C 0.5032(7) 0.5886(4) 0.1778(4) 0.0810(18) Uani 1 1 d . . . . .
H1S1 H 0.448295 0.624108 0.206008 0.121 Uiso 1 1 calc R U . . .
H1S2 H 0.453348 0.550804 0.148781 0.121 Uiso 1 1 calc R U . . .
H1S3 H 0.554584 0.623233 0.146833 0.121 Uiso 1 1 calc R U . . .
O1S O 0.5811(4) 0.5414(2) 0.2244(2) 0.0663(10) Uani 1 1 d . . . . .
H1S H 0.618741 0.573586 0.251785 0.099 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C2A 1.375(6) . ?
C1A C10A 1.450(5) . ?
C1A P1A 1.825(4) . ?
C2A O2A 1.364(5) . ?
C2A C3A 1.416(6) . ?
C3A C4A 1.334(7) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.414(7) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.414(7) . ?
C5A C10A 1.425(6) . ?
C6A C7A 1.347(9) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.399(9) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.373(6) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.408(6) . ?
C9A H9A 0.9300 . ?
C11A C14A 1.519(6) . ?
C11A C12A 1.526(6) . ?
C11A C13A 1.534(6) . ?
C11A P1A 1.839(4) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C15A C20A 1.414(5) . ?
C15A C16A 1.414(5) . ?
C15A S1A 1.780(4) . ?
C16A C17A 1.394(5) . ?
C16A C21A 1.519(5) . ?
C17A C18A 1.382(6) . ?
C17A H17A 0.9300 . ?
C18A C19A 1.380(6) . ?
C18A C24A 1.517(6) . ?
C19A C20A 1.396(6) . ?
C19A H19A 0.9300 . ?
C20A C27A 1.533(5) . ?
C21A C23A 1.517(6) . ?
C21A C22A 1.534(6) . ?
C21A H21A 0.9800 . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?
C23A H23A 0.9600 . ?
C23A H23B 0.9600 . ?
C23A H23C 0.9600 . ?
C24A C25A 1.496(7) . ?
C24A C26A 1.525(8) . ?
C24A H24A 0.9800 . ?
C25A H25A 0.9600 . ?
C25A H25B 0.9600 . ?
C25A H25C 0.9600 . ?
C26A H26A 0.9600 . ?
C26A H26B 0.9600 . ?
C26A H26C 0.9600 . ?
C27A C29A 1.526(6) . ?
C27A C28A 1.535(6) . ?
C27A H27A 0.9800 . ?
C28A H28A 0.9600 . ?
C28A H28B 0.9600 . ?
C28A H28C 0.9600 . ?
C29A H29A 0.9600 . ?
C29A H29B 0.9600 . ?
C29A H29C 0.9600 . ?
O3A S1A 1.425(4) . ?
O4A S1A 1.428(3) . ?
S1A N1A 1.659(4) . ?
N1A S1B 1.49(2) . ?
N1A P1A 1.687(3) . ?
N1A H1A 0.8600 . ?
N1A H1B 0.8600 . ?
O1A P1A 1.482(3) . ?
O2A H2A 0.8200 . ?
S1B O3B 1.4219 . ?
S1B O4B 1.4262 . ?
S1B C15B 1.7821 . ?
C15B C16B 1.4131 . ?
C15B C20B 1.4136 . ?
C16B C17B 1.3937 . ?
C16B C21B 1.5190 . ?
C17B C18B 1.3815 . ?
C17B H17B 0.9300 . ?
C18B C19B 1.3812 . ?
C18B C24B 1.5185 . ?
C19B C20B 1.3976 . ?
C19B H19B 0.9300 . ?
C20B C27B 1.5326 . ?
C21B C23B 1.526(11) . ?
C21B C22B 1.527(11) . ?
C21B H21B 0.9800 . ?
C24B C26B 1.523(11) . ?
C24B C25B 1.526(11) . ?
C24B H24B 0.9800 . ?
C27B C29B 1.522(11) . ?
C27B C28B 1.522(11) . ?
C27B H27B 0.9800 . ?
C28B H28D 0.9600 . ?
C28B H28E 0.9600 . ?
C28B H28F 0.9600 . ?
C29B H29D 0.9600 . ?
C29B H29E 0.9600 . ?
C29B H29F 0.9600 . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
C23B H23D 0.9600 . ?
C23B H23E 0.9600 . ?
C23B H23F 0.9600 . ?
C25B H25D 0.9600 . ?
C25B H25E 0.9600 . ?
C25B H25F 0.9600 . ?
C26B H26D 0.9600 . ?
C26B H26E 0.9600 . ?
C26B H26F 0.9600 . ?
C1S O1S 1.405(8) . ?
C1S H1S1 0.9600 . ?
C1S H1S2 0.9600 . ?
C1S H1S3 0.9600 . ?
O1S H1S 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A C1A C10A 119.1(3) . . ?
C2A C1A P1A 121.3(3) . . ?
C10A C1A P1A 119.6(3) . . ?
O2A C2A C1A 121.1(4) . . ?
O2A C2A C3A 118.2(4) . . ?
C1A C2A C3A 120.7(4) . . ?
C4A C3A C2A 121.1(5) . . ?
C4A C3A H3A 119.4 . . ?
C2A C3A H3A 119.4 . . ?
C3A C4A C5A 121.4(4) . . ?
C3A C4A H4A 119.3 . . ?
C5A C4A H4A 119.3 . . ?
C4A C5A C6A 120.7(4) . . ?
C4A C5A C10A 119.1(4) . . ?
C6A C5A C10A 120.2(5) . . ?
C7A C6A C5A 121.2(5) . . ?
C7A C6A H6A 119.4 . . ?
C5A C6A H6A 119.4 . . ?
C6A C7A C8A 119.0(5) . . ?
C6A C7A H7A 120.5 . . ?
C8A C7A H7A 120.5 . . ?
C9A C8A C7A 121.8(5) . . ?
C9A C8A H8A 119.1 . . ?
C7A C8A H8A 119.1 . . ?
C8A C9A C10A 120.8(5) . . ?
C8A C9A H9A 119.6 . . ?
C10A C9A H9A 119.6 . . ?
C9A C10A C5A 116.9(4) . . ?
C9A C10A C1A 124.5(4) . . ?
C5A C10A C1A 118.6(4) . . ?
C14A C11A C12A 109.2(4) . . ?
C14A C11A C13A 111.1(4) . . ?
C12A C11A C13A 109.3(4) . . ?
C14A C11A P1A 108.0(3) . . ?
C12A C11A P1A 110.5(3) . . ?
C13A C11A P1A 108.6(3) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C11A C14A H14A 109.5 . . ?
C11A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C11A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C20A C15A C16A 121.6(4) . . ?
C20A C15A S1A 121.8(3) . . ?
C16A C15A S1A 116.5(3) . . ?
C17A C16A C15A 117.3(4) . . ?
C17A C16A C21A 115.8(4) . . ?
C15A C16A C21A 126.9(4) . . ?
C18A C17A C16A 123.0(4) . . ?
C18A C17A H17A 118.5 . . ?
C16A C17A H17A 118.5 . . ?
C19A C18A C17A 117.8(4) . . ?
C19A C18A C24A 120.1(4) . . ?
C17A C18A C24A 122.1(4) . . ?
C18A C19A C20A 123.5(4) . . ?
C18A C19A H19A 118.3 . . ?
C20A C19A H19A 118.3 . . ?
C19A C20A C15A 116.8(4) . . ?
C19A C20A C27A 116.9(4) . . ?
C15A C20A C27A 126.3(4) . . ?
C23A C21A C16A 113.2(4) . . ?
C23A C21A C22A 110.6(5) . . ?
C16A C21A C22A 109.7(4) . . ?
C23A C21A H21A 107.7 . . ?
C16A C21A H21A 107.7 . . ?
C22A C21A H21A 107.7 . . ?
C21A C22A H22A 109.5 . . ?
C21A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C21A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C21A C23A H23A 109.5 . . ?
C21A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C21A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C25A C24A C18A 112.7(5) . . ?
C25A C24A C26A 112.6(7) . . ?
C18A C24A C26A 110.7(5) . . ?
C25A C24A H24A 106.8 . . ?
C18A C24A H24A 106.8 . . ?
C26A C24A H24A 106.8 . . ?
C24A C25A H25A 109.5 . . ?
C24A C25A H25B 109.5 . . ?
H25A C25A H25B 109.5 . . ?
C24A C25A H25C 109.5 . . ?
H25A C25A H25C 109.5 . . ?
H25B C25A H25C 109.5 . . ?
C24A C26A H26A 109.5 . . ?
C24A C26A H26B 109.5 . . ?
H26A C26A H26B 109.5 . . ?
C24A C26A H26C 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
C29A C27A C20A 113.4(4) . . ?
C29A C27A C28A 110.7(5) . . ?
C20A C27A C28A 109.1(4) . . ?
C29A C27A H27A 107.8 . . ?
C20A C27A H27A 107.8 . . ?
C28A C27A H27A 107.8 . . ?
C27A C28A H28A 109.5 . . ?
C27A C28A H28B 109.5 . . ?
H28A C28A H28B 109.5 . . ?
C27A C28A H28C 109.5 . . ?
H28A C28A H28C 109.5 . . ?
H28B C28A H28C 109.5 . . ?
C27A C29A H29A 109.5 . . ?
C27A C29A H29B 109.5 . . ?
H29A C29A H29B 109.5 . . ?
C27A C29A H29C 109.5 . . ?
H29A C29A H29C 109.5 . . ?
H29B C29A H29C 109.5 . . ?
O3A S1A O4A 118.0(2) . . ?
O3A S1A N1A 107.4(2) . . ?
O4A S1A N1A 105.1(2) . . ?
O3A S1A C15A 110.3(2) . . ?
O4A S1A C15A 108.87(19) . . ?
N1A S1A C15A 106.50(18) . . ?
S1B N1A P1A 136.5(8) . . ?
S1A N1A P1A 127.4(2) . . ?
S1A N1A H1A 116.3 . . ?
P1A N1A H1A 116.3 . . ?
S1B N1A H1B 111.7 . . ?
P1A N1A H1B 111.7 . . ?
C2A O2A H2A 109.5 . . ?
O1A P1A N1A 109.33(16) . . ?
O1A P1A C1A 113.45(16) . . ?
N1A P1A C1A 104.80(17) . . ?
O1A P1A C11A 113.44(19) . . ?
N1A P1A C11A 107.86(17) . . ?
C1A P1A C11A 107.48(18) . . ?
O3B S1B O4B 117.7 . . ?
O3B S1B N1A 105.1(10) . . ?
O4B S1B N1A 106.3(10) . . ?
O3B S1B C15B 110.3 . . ?
O4B S1B C15B 108.8 . . ?
N1A S1B C15B 108.1(10) . . ?
C16B C15B C20B 121.6 . . ?
C16B C15B S1B 116.6 . . ?
C20B C15B S1B 121.8 . . ?
C17B C16B C15B 117.5 . . ?
C17B C16B C21B 115.6 . . ?
C15B C16B C21B 126.9 . . ?
C18B C17B C16B 122.9 . . ?
C18B C17B H17B 118.6 . . ?
C16B C17B H17B 118.6 . . ?
C19B C18B C17B 117.7 . . ?
C19B C18B C24B 120.1 . . ?
C17B C18B C24B 122.1 . . ?
C18B C19B C20B 123.6 . . ?
C18B C19B H19B 118.2 . . ?
C20B C19B H19B 118.2 . . ?
C19B C20B C15B 116.6 . . ?
C19B C20B C27B 117.1 . . ?
C15B C20B C27B 126.2 . . ?
C16B C21B C23B 109.7(13) . . ?
C16B C21B C22B 110.2(13) . . ?
C23B C21B C22B 119(3) . . ?
C16B C21B H21B 105.7 . . ?
C23B C21B H21B 105.7 . . ?
C22B C21B H21B 105.7 . . ?
C18B C24B C26B 111.3(14) . . ?
C18B C24B C25B 110.3(14) . . ?
C26B C24B C25B 121(5) . . ?
C18B C24B H24B 104.0 . . ?
C26B C24B H24B 104.0 . . ?
C25B C24B H24B 104.0 . . ?
C29B C27B C28B 92(4) . . ?
C29B C27B C20B 110.9(14) . . ?
C28B C27B C20B 111.0(14) . . ?
C29B C27B H27B 113.7 . . ?
C28B C27B H27B 113.7 . . ?
C20B C27B H27B 113.7 . . ?
C27B C28B H28D 109.5 . . ?
C27B C28B H28E 109.5 . . ?
H28D C28B H28E 109.5 . . ?
C27B C28B H28F 109.5 . . ?
H28D C28B H28F 109.5 . . ?
H28E C28B H28F 109.5 . . ?
C27B C29B H29D 109.5 . . ?
C27B C29B H29E 109.5 . . ?
H29D C29B H29E 109.5 . . ?
C27B C29B H29F 109.5 . . ?
H29D C29B H29F 109.5 . . ?
H29E C29B H29F 109.5 . . ?
C21B C22B H22D 109.5 . . ?
C21B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C21B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C21B C23B H23D 109.5 . . ?
C21B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C21B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C24B C25B H25D 109.5 . . ?
C24B C25B H25E 109.5 . . ?
H25D C25B H25E 109.5 . . ?
C24B C25B H25F 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?
C24B C26B H26D 109.5 . . ?
C24B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C24B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
O1S C1S H1S1 109.5 . . ?
O1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
O1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C1S O1S H1S 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
C10A C1A C2A O2A 179.5(4) . . . . ?
P1A C1A C2A O2A -2.5(6) . . . . ?
C10A C1A C2A C3A -1.0(6) . . . . ?
P1A C1A C2A C3A 177.0(4) . . . . ?
O2A C2A C3A C4A 179.1(5) . . . . ?
C1A C2A C3A C4A -0.5(8) . . . . ?
C2A C3A C4A C5A 0.3(9) . . . . ?
C3A C4A C5A C6A -179.2(5) . . . . ?
C3A C4A C5A C10A 1.3(8) . . . . ?
C4A C5A C6A C7A -179.8(5) . . . . ?
C10A C5A C6A C7A -0.3(7) . . . . ?
C5A C6A C7A C8A 2.6(8) . . . . ?
C6A C7A C8A C9A -2.2(9) . . . . ?
C7A C8A C9A C10A -0.7(8) . . . . ?
C8A C9A C10A C5A 3.0(7) . . . . ?
C8A C9A C10A C1A -177.4(4) . . . . ?
C4A C5A C10A C9A 177.0(4) . . . . ?
C6A C5A C10A C9A -2.5(6) . . . . ?
C4A C5A C10A C1A -2.7(6) . . . . ?
C6A C5A C10A C1A 177.8(4) . . . . ?
C2A C1A C10A C9A -177.1(4) . . . . ?
P1A C1A C10A C9A 4.9(6) . . . . ?
C2A C1A C10A C5A 2.6(6) . . . . ?
P1A C1A C10A C5A -175.5(3) . . . . ?
C20A C15A C16A C17A -1.4(5) . . . . ?
S1A C15A C16A C17A 175.9(3) . . . . ?
C20A C15A C16A C21A 179.9(4) . . . . ?
S1A C15A C16A C21A -2.8(5) . . . . ?
C15A C16A C17A C18A -0.1(5) . . . . ?
C21A C16A C17A C18A 178.7(4) . . . . ?
C16A C17A C18A C19A 1.3(7) . . . . ?
C16A C17A C18A C24A 178.7(4) . . . . ?
C17A C18A C19A C20A -1.0(7) . . . . ?
C24A C18A C19A C20A -178.5(5) . . . . ?
C18A C19A C20A C15A -0.4(7) . . . . ?
C18A C19A C20A C27A -179.1(5) . . . . ?
C16A C15A C20A C19A 1.7(6) . . . . ?
S1A C15A C20A C19A -175.5(3) . . . . ?
C16A C15A C20A C27A -179.8(4) . . . . ?
S1A C15A C20A C27A 3.0(6) . . . . ?
C17A C16A C21A C23A 47.2(6) . . . . ?
C15A C16A C21A C23A -134.1(5) . . . . ?
C17A C16A C21A C22A -76.8(5) . . . . ?
C15A C16A C21A C22A 101.9(5) . . . . ?
C19A C18A C24A C25A -133.7(6) . . . . ?
C17A C18A C24A C25A 49.0(8) . . . . ?
C19A C18A C24A C26A 99.1(7) . . . . ?
C17A C18A C24A C26A -78.2(8) . . . . ?
C19A C20A C27A C29A -34.8(6) . . . . ?
C15A C20A C27A C29A 146.7(5) . . . . ?
C19A C20A C27A C28A 89.1(5) . . . . ?
C15A C20A C27A C28A -89.4(5) . . . . ?
C20A C15A S1A O3A 5.4(4) . . . . ?
C16A C15A S1A O3A -171.9(3) . . . . ?
C20A C15A S1A O4A 136.3(3) . . . . ?
C16A C15A S1A O4A -41.0(3) . . . . ?
C20A C15A S1A N1A -110.8(3) . . . . ?
C16A C15A S1A N1A 71.9(3) . . . . ?
O3A S1A N1A P1A -41.8(3) . . . . ?
O4A S1A N1A P1A -168.2(2) . . . . ?
C15A S1A N1A P1A 76.4(3) . . . . ?
S1B N1A P1A O1A -16.6(12) . . . . ?
S1A N1A P1A O1A -26.1(3) . . . . ?
S1B N1A P1A C1A -138.5(12) . . . . ?
S1A N1A P1A C1A -148.0(2) . . . . ?
S1B N1A P1A C11A 107.2(12) . . . . ?
S1A N1A P1A C11A 97.7(3) . . . . ?
C2A C1A P1A O1A -146.7(3) . . . . ?
C10A C1A P1A O1A 31.3(4) . . . . ?
C2A C1A P1A N1A -27.5(4) . . . . ?
C10A C1A P1A N1A 150.5(3) . . . . ?
C2A C1A P1A C11A 87.0(4) . . . . ?
C10A C1A P1A C11A -95.0(3) . . . . ?
C14A C11A P1A O1A -68.0(4) . . . . ?
C12A C11A P1A O1A 172.6(3) . . . . ?
C13A C11A P1A O1A 52.7(4) . . . . ?
C14A C11A P1A N1A 170.8(3) . . . . ?
C12A C11A P1A N1A 51.4(4) . . . . ?
C13A C11A P1A N1A -68.5(4) . . . . ?
C14A C11A P1A C1A 58.3(4) . . . . ?
C12A C11A P1A C1A -61.1(4) . . . . ?
C13A C11A P1A C1A 179.0(3) . . . . ?
P1A N1A S1B O3B -57.7(12) . . . . ?
P1A N1A S1B O4B 176.8(10) . . . . ?
P1A N1A S1B C15B 60.1(13) . . . . ?
O3B S1B C15B C16B -171.6 . . . . ?
O4B S1B C15B C16B -41.0 . . . . ?
N1A S1B C15B C16B 74.0(11) . . . . ?
O3B S1B C15B C20B 5.6 . . . . ?
O4B S1B C15B C20B 136.2 . . . . ?
N1A S1B C15B C20B -108.8(11) . . . . ?
C20B C15B C16B C17B -1.4 . . . . ?
S1B C15B C16B C17B 175.9 . . . . ?
C20B C15B C16B C21B 179.7 . . . . ?
S1B C15B C16B C21B -3.1 . . . . ?
C15B C16B C17B C18B -0.3 . . . . ?
C21B C16B C17B C18B 178.8 . . . . ?
C16B C17B C18B C19B 1.2 . . . . ?
C16B C17B C18B C24B 178.5 . . . . ?
C17B C18B C19B C20B -0.5 . . . . ?
C24B C18B C19B C20B -177.9 . . . . ?
C18B C19B C20B C15B -1.0 . . . . ?
C18B C19B C20B C27B -178.7 . . . . ?
C16B C15B C20B C19B 1.9 . . . . ?
S1B C15B C20B C19B -175.1 . . . . ?
C16B C15B C20B C27B 179.4 . . . . ?
S1B C15B C20B C27B 2.3 . . . . ?
C17B C16B C21B C23B 59(3) . . . . ?
C15B C16B C21B C23B -122(3) . . . . ?
C17B C16B C21B C22B -73(3) . . . . ?
C15B C16B C21B C22B 106(3) . . . . ?
C19B C18B C24B C26B 86(5) . . . . ?
C17B C18B C24B C26B -92(5) . . . . ?
C19B C18B C24B C25B -137(4) . . . . ?
C17B C18B C24B C25B 46(4) . . . . ?
C19B C20B C27B C29B -48(4) . . . . ?
C15B C20B C27B C29B 135(4) . . . . ?
C19B C20B C27B C28B 53(3) . . . . ?
C15B C20B C27B C28B -124(3) . . . . ?

_refine_diff_density_max         0.477
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.047


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/dichloromethane/pentane'
####################################################################### 
# 
# 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_11a_253K
_database_code_depnum_ccdc_archive 'CCDC 1935846'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2019-06-21 deposited with the CCDC.	2019-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C10 H12 Br N'
_chemical_formula_sum            'C10 H12 Br N'
_chemical_formula_weight         226.12

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'
Br Br -0.6763 1.2805 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   16.0321(5)
_cell_length_b                   6.1532(2)
_cell_length_c                   9.7828(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     965.06(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    253.0(1)
_cell_measurement_reflns_used    9863
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      79.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.294
_exptl_absorpt_coefficient_mu    5.338
_shelx_estimated_absorpt_T_min   0.266
_shelx_estimated_absorpt_T_max   0.303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5764
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'

_diffrn_ambient_temperature      253.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Cu)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_detector                 CPAD
_diffrn_detector_type            'PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            25154
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.297
_diffrn_reflns_theta_max         80.534
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2073
_reflns_number_gt                2050
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.993

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+5.0032P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick, 2015)'
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.050(18)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2073
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1582
_refine_ls_wR_factor_gt          0.1579
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2A C 0.3779(6) 0.4903(17) 0.9900(11) 0.051(2) Uani 1 1 d . . . . .
H2A H 0.423971 0.399580 1.022915 0.062 Uiso 1 1 calc R U . . .
C3A C 0.3025(6) 0.3451(18) 0.9588(9) 0.050(2) Uani 1 1 d . . . . .
H3A1 H 0.283776 0.274473 1.041991 0.059 Uiso 1 1 calc R U . . .
H3A2 H 0.256962 0.433203 0.924074 0.059 Uiso 1 1 calc R U . . .
C4A C 0.3265(7) 0.1734(17) 0.8527(11) 0.057(3) Uani 1 1 d . . . . .
H4A1 H 0.366104 0.072852 0.892918 0.069 Uiso 1 1 calc R U . . .
H4A2 H 0.277244 0.091624 0.826817 0.069 Uiso 1 1 calc R U . . .
C5A C 0.3670(6) 0.1699(16) 0.6005(10) 0.045(2) Uani 1 1 d . . . . .
H5A H 0.344252 0.031509 0.592179 0.054 Uiso 1 1 calc R U . . .
C6A C 0.4018(6) 0.2667(15) 0.4912(11) 0.048(2) Uani 1 1 d . . . . .
C7A C 0.4371(6) 0.4682(16) 0.4989(10) 0.045(2) Uani 1 1 d . . . . .
H7A H 0.461136 0.531696 0.422151 0.054 Uiso 1 1 calc R U . . .
C8A C 0.4364(5) 0.5750(15) 0.6215(10) 0.044(2) Uani 1 1 d . . . . .
H8A H 0.459435 0.713534 0.626453 0.053 Uiso 1 1 calc R U . . .
C9A C 0.4020(6) 0.4824(13) 0.7402(9) 0.0394(18) Uani 1 1 d . . . . .
C10A C 0.3650(5) 0.2754(15) 0.7253(10) 0.042(2) Uani 1 1 d . . . . .
C11A C 0.3591(7) 0.664(2) 1.0959(11) 0.063(3) Uani 1 1 d . . . . .
H11A H 0.409087 0.743966 1.116016 0.094 Uiso 1 1 calc R U . . .
H11B H 0.338674 0.597075 1.177883 0.094 Uiso 1 1 calc R U . . .
H11C H 0.317582 0.761851 1.060651 0.094 Uiso 1 1 calc R U . . .
Br1A Br 0.40196(9) 0.1104(3) 0.32166(13) 0.0760(6) Uani 1 1 d . . . . .
N1A N 0.4025(6) 0.5944(14) 0.8624(8) 0.0519(19) Uani 1 1 d G . . . .
H1A H 0.430596 0.713301 0.858930 0.062 Uiso 1 1 d G U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2A N1A 1.457(13) . ?
C2A C11A 1.520(14) . ?
C2A C3A 1.535(14) . ?
C2A H2A 0.9800 . ?
C3A C4A 1.531(15) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4A C10A 1.526(14) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A C6A 1.345(14) . ?
C5A C10A 1.383(13) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.365(13) . ?
C6A Br1A 1.918(9) . ?
C7A C8A 1.367(14) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.407(13) . ?
C8A H8A 0.9300 . ?
C9A N1A 1.380(11) . ?
C9A C10A 1.413(11) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
N1A H1A 0.8600 . ?

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
N1A C2A C11A 109.2(9) . . ?
N1A C2A C3A 107.4(8) . . ?
C11A C2A C3A 112.9(8) . . ?
N1A C2A H2A 109.1 . . ?
C11A C2A H2A 109.1 . . ?
C3A C2A H2A 109.1 . . ?
C4A C3A C2A 109.8(8) . . ?
C4A C3A H3A1 109.7 . . ?
C2A C3A H3A1 109.7 . . ?
C4A C3A H3A2 109.7 . . ?
C2A C3A H3A2 109.7 . . ?
H3A1 C3A H3A2 108.2 . . ?
C10A C4A C3A 111.8(8) . . ?
C10A C4A H4A1 109.3 . . ?
C3A C4A H4A1 109.3 . . ?
C10A C4A H4A2 109.3 . . ?
C3A C4A H4A2 109.3 . . ?
H4A1 C4A H4A2 107.9 . . ?
C6A C5A C10A 120.2(8) . . ?
C6A C5A H5A 119.9 . . ?
C10A C5A H5A 119.9 . . ?
C5A C6A C7A 122.0(9) . . ?
C5A C6A Br1A 117.8(7) . . ?
C7A C6A Br1A 120.2(8) . . ?
C6A C7A C8A 118.8(9) . . ?
C6A C7A H7A 120.6 . . ?
C8A C7A H7A 120.6 . . ?
C7A C8A C9A 122.2(8) . . ?
C7A C8A H8A 118.9 . . ?
C9A C8A H8A 118.9 . . ?
N1A C9A C8A 120.7(7) . . ?
N1A C9A C10A 122.8(9) . . ?
C8A C9A C10A 116.4(8) . . ?
C5A C10A C9A 120.3(9) . . ?
C5A C10A C4A 122.5(8) . . ?
C9A C10A C4A 117.1(9) . . ?
C2A C11A H11A 109.5 . . ?
C2A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C2A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C9A N1A C2A 121.4(8) . . ?
C9A N1A H1A 113.2 . . ?
C2A N1A H1A 123.3 . . ?

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
N1A C2A C3A C4A 60.2(10) . . . . ?
C11A C2A C3A C4A -179.5(9) . . . . ?
C2A C3A C4A C10A -53.4(11) . . . . ?
C10A C5A C6A C7A 1.0(15) . . . . ?
C10A C5A C6A Br1A -179.8(7) . . . . ?
C5A C6A C7A C8A -0.4(14) . . . . ?
Br1A C6A C7A C8A -179.6(7) . . . . ?
C6A C7A C8A C9A 1.3(14) . . . . ?
C7A C8A C9A N1A 179.9(9) . . . . ?
C7A C8A C9A C10A -2.5(13) . . . . ?
C6A C5A C10A C9A -2.3(14) . . . . ?
C6A C5A C10A C4A -179.9(9) . . . . ?
N1A C9A C10A C5A -179.4(9) . . . . ?
C8A C9A C10A C5A 2.9(12) . . . . ?
N1A C9A C10A C4A -1.7(13) . . . . ?
C8A C9A C10A C4A -179.4(9) . . . . ?
C3A C4A C10A C5A -158.6(9) . . . . ?
C3A C4A C10A C9A 23.7(12) . . . . ?
C8A C9A N1A C2A -171.4(8) . . . . ?
C10A C9A N1A C2A 11.1(15) . . . . ?
C11A C2A N1A C9A -162.8(10) . . . . ?
C3A C2A N1A C9A -40.1(12) . . . . ?

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.102


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/pentane'
####################################################################### 
# 
# 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_8d_253K
_database_code_depnum_ccdc_archive 'CCDC 1935845'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2019-06-21 deposited with the CCDC.	2019-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         '2(C15 H20 N O2 P), C H2 Cl2'
_chemical_formula_sum            'C31 H42 Cl2 N2 O4 P2'
_chemical_formula_weight         639.50

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+1/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+3/4'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   10.7127(2)
_cell_length_b                   10.7127(2)
_cell_length_c                   27.9476(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3207.32(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    253.0(1)
_cell_measurement_reflns_used    9300
_cell_measurement_theta_min      6.05
_cell_measurement_theta_max      72.46

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.221
_exptl_absorpt_coefficient_mu    3.070
_shelx_estimated_absorpt_T_min   0.446
_shelx_estimated_absorpt_T_max   0.550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6107
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause, Herbst-Irmer, Sheldrick & Stalke, 2015)'

_diffrn_ambient_temperature      253.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Incoatec Microfocus X-ray Source I\mS (Cu)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Bruker D8 Venture, Dual, Cu at zero, PHOTON II'
_diffrn_detector                 CPAD
_diffrn_detector_type            'PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            45989
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         4.420
_diffrn_reflns_theta_max         72.457
_diffrn_reflns_theta_full        67.750
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3167
_reflns_number_gt                3143
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+0.5247P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 
;
 Flack x determined using 1256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3167
_refine_ls_number_parameters     208
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0744
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.09889(16) 0.46342(16) 0.79114(6) 0.0295(4) Uani 1 1 d . . . . .
C2A C 0.01280(18) 0.40735(18) 0.76091(7) 0.0348(4) Uani 1 1 d . . . . .
C3A C 0.0050(2) 0.2758(2) 0.75620(8) 0.0449(5) Uani 1 1 d . . . . .
H3A H -0.050928 0.240806 0.734587 0.054 Uiso 1 1 calc R U . . .
C4A C 0.0789(2) 0.20114(19) 0.78315(8) 0.0469(5) Uani 1 1 d . . . . .
H4A H 0.073211 0.115008 0.779612 0.056 Uiso 1 1 calc R U . . .
C5A C 0.1643(2) 0.25098(18) 0.81645(8) 0.0388(4) Uani 1 1 d . . . . .
C6A C 0.2370(3) 0.1725(2) 0.84618(9) 0.0502(6) Uani 1 1 d . . . . .
H6A H 0.225968 0.086491 0.844426 0.060 Uiso 1 1 calc R U . . .
C7A C 0.3225(2) 0.2197(2) 0.87723(9) 0.0516(6) Uani 1 1 d . . . . .
H7A H 0.369574 0.166728 0.896465 0.062 Uiso 1 1 calc R U . . .
C8A C 0.3387(2) 0.3498(2) 0.87985(8) 0.0468(5) Uani 1 1 d . . . . .
H8A H 0.398604 0.382486 0.900428 0.056 Uiso 1 1 calc R U . . .
C9A C 0.26808(19) 0.42898(19) 0.85267(7) 0.0378(4) Uani 1 1 d . . . . .
H9A H 0.279821 0.514631 0.855696 0.045 Uiso 1 1 calc R U . . .
C10A C 0.17729(17) 0.38389(18) 0.81997(7) 0.0321(4) Uani 1 1 d . . . . .
C11A C -0.00654(18) 0.69372(18) 0.83408(7) 0.0344(4) Uani 1 1 d . . . . .
C12A C -0.1393(2) 0.6612(2) 0.81884(10) 0.0507(5) Uani 1 1 d . . . . .
H12A H -0.149100 0.572124 0.818342 0.076 Uiso 1 1 calc R U . . .
H12B H -0.154876 0.694160 0.787466 0.076 Uiso 1 1 calc R U . . .
H12C H -0.197453 0.696802 0.841123 0.076 Uiso 1 1 calc R U . . .
C13A C 0.0094(3) 0.8361(2) 0.83559(9) 0.0508(6) Uani 1 1 d . . . . .
H13A H -0.002461 0.869782 0.804086 0.076 Uiso 1 1 calc R U . . .
H13B H 0.091870 0.856138 0.846650 0.076 Uiso 1 1 calc R U . . .
H13C H -0.051150 0.871431 0.856979 0.076 Uiso 1 1 calc R U . . .
C14A C 0.0192(2) 0.6389(2) 0.88404(7) 0.0493(5) Uani 1 1 d . . . . .
H14A H 0.009160 0.549896 0.883079 0.074 Uiso 1 1 calc R U . . .
H14B H -0.038423 0.673845 0.906668 0.074 Uiso 1 1 calc R U . . .
H14C H 0.103039 0.658799 0.893518 0.074 Uiso 1 1 calc R U . . .
C15A C -0.1727(2) 0.4339(3) 0.71274(10) 0.0538(6) Uani 1 1 d . . . . .
H15A H -0.218050 0.383226 0.735122 0.081 Uiso 1 1 calc R U . . .
H15B H -0.148168 0.383905 0.685839 0.081 Uiso 1 1 calc R U . . .
H15C H -0.224943 0.501132 0.702003 0.081 Uiso 1 1 calc R U . . .
N1A N 0.08319(16) 0.69295(16) 0.73976(6) 0.0352(4) Uani 1 1 d G . . . .
H1AA H 0.027269 0.657146 0.720670 0.066(9) Uiso 1 1 d G . . . .
H1AB H 0.150261 0.713956 0.722812 0.050(7) Uiso 1 1 d G . . . .
O1A O 0.23916(12) 0.67681(12) 0.80877(5) 0.0331(3) Uani 1 1 d . . . . .
O2A O -0.06436(14) 0.48360(14) 0.73542(5) 0.0426(3) Uani 1 1 d . . . . .
P1A P 0.11297(4) 0.63480(4) 0.79310(2) 0.02598(13) Uani 1 1 d . . . . .
C1S C 0.4775(6) 0.5568(5) 0.7560(3) 0.0552(19) Uani 0.5 1 d D U P A -1
H1S1 H 0.404655 0.595282 0.770416 0.066 Uiso 0.5 1 calc R U P A -1
H1S2 H 0.520552 0.619844 0.737354 0.066 Uiso 0.5 1 calc R U P A -1
Cl1S Cl 0.57635(15) 0.50225(17) 0.80097(7) 0.0645(4) Uani 0.5 1 d D U P A -1
Cl2S Cl 0.4306(3) 0.4356(2) 0.71862(9) 0.1018(7) Uani 0.5 1 d D U P A -1


_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
C1A C2A 1.387(3) . ?
C1A C10A 1.442(3) . ?
C1A P1A 1.8430(17) . ?
C2A O2A 1.363(3) . ?
C2A C3A 1.417(3) . ?
C3A C4A 1.355(3) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.410(3) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.415(3) . ?
C5A C10A 1.434(3) . ?
C6A C7A 1.359(4) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.406(4) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.368(3) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.419(3) . ?
C9A H9A 0.9300 . ?
C11A C12A 1.525(3) . ?
C11A C13A 1.536(3) . ?
C11A C14A 1.540(3) . ?
C11A P1A 1.8302(19) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C14A H14A 0.9600 . ?
C14A H14B 0.9600 . ?
C14A H14C 0.9600 . ?
C15A O2A 1.426(2) . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
N1A P1A 1.6469(16) . ?
N1A H1AA 0.8891 . ?
N1A H1AB 0.8895 . ?
O1A P1A 1.4905(13) . ?
C1S Cl2S 1.742(5) . ?
C1S Cl1S 1.743(6) . ?
C1S H1S1 0.9700 . ?
C1S H1S2 0.9700 . ?

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
C2A C1A C10A 118.13(16) . . ?
C2A C1A P1A 120.25(14) . . ?
C10A C1A P1A 121.61(13) . . ?
O2A C2A C1A 117.50(17) . . ?
O2A C2A C3A 120.76(18) . . ?
C1A C2A C3A 121.7(2) . . ?
C4A C3A C2A 120.1(2) . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 121.50(19) . . ?
C3A C4A H4A 119.2 . . ?
C5A C4A H4A 119.2 . . ?
C4A C5A C6A 121.28(19) . . ?
C4A C5A C10A 118.95(19) . . ?
C6A C5A C10A 119.8(2) . . ?
C7A C6A C5A 121.6(2) . . ?
C7A C6A H6A 119.2 . . ?
C5A C6A H6A 119.2 . . ?
C6A C7A C8A 119.0(2) . . ?
C6A C7A H7A 120.5 . . ?
C8A C7A H7A 120.5 . . ?
C9A C8A C7A 121.2(2) . . ?
C9A C8A H8A 119.4 . . ?
C7A C8A H8A 119.4 . . ?
C8A C9A C10A 121.7(2) . . ?
C8A C9A H9A 119.1 . . ?
C10A C9A H9A 119.1 . . ?
C9A C10A C5A 116.64(18) . . ?
C9A C10A C1A 123.90(17) . . ?
C5A C10A C1A 119.46(18) . . ?
C12A C11A C13A 109.79(19) . . ?
C12A C11A C14A 109.48(18) . . ?
C13A C11A C14A 109.51(18) . . ?
C12A C11A P1A 113.50(14) . . ?
C13A C11A P1A 106.37(14) . . ?
C14A C11A P1A 108.09(14) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C11A C14A H14A 109.5 . . ?
C11A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C11A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
O2A C15A H15A 109.5 . . ?
O2A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
O2A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
P1A N1A H1AA 120.7 . . ?
P1A N1A H1AB 114.9 . . ?
H1AA N1A H1AB 109.5 . . ?
C2A O2A C15A 120.15(17) . . ?
O1A P1A N1A 109.12(8) . . ?
O1A P1A C11A 110.27(9) . . ?
N1A P1A C11A 107.49(9) . . ?
O1A P1A C1A 112.56(8) . . ?
N1A P1A C1A 109.51(9) . . ?
C11A P1A C1A 107.75(8) . . ?
Cl2S C1S Cl1S 111.0(3) . . ?
Cl2S C1S H1S1 109.4 . . ?
Cl1S C1S H1S1 109.4 . . ?
Cl2S C1S H1S2 109.4 . . ?
Cl1S C1S H1S2 109.4 . . ?
H1S1 C1S H1S2 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10A C1A C2A O2A 177.22(16) . . . . ?
P1A C1A C2A O2A -3.8(2) . . . . ?
C10A C1A C2A C3A -3.1(3) . . . . ?
P1A C1A C2A C3A 175.86(15) . . . . ?
O2A C2A C3A C4A -177.40(19) . . . . ?
C1A C2A C3A C4A 3.0(3) . . . . ?
C2A C3A C4A C5A 0.3(3) . . . . ?
C3A C4A C5A C6A 176.9(2) . . . . ?
C3A C4A C5A C10A -3.2(3) . . . . ?
C4A C5A C6A C7A 177.8(2) . . . . ?
C10A C5A C6A C7A -2.2(3) . . . . ?
C5A C6A C7A C8A 0.1(4) . . . . ?
C6A C7A C8A C9A 1.6(4) . . . . ?
C7A C8A C9A C10A -1.3(3) . . . . ?
C8A C9A C10A C5A -0.7(3) . . . . ?
C8A C9A C10A C1A 178.84(18) . . . . ?
C4A C5A C10A C9A -177.56(18) . . . . ?
C6A C5A C10A C9A 2.4(3) . . . . ?
C4A C5A C10A C1A 2.9(3) . . . . ?
C6A C5A C10A C1A -177.17(18) . . . . ?
C2A C1A C10A C9A -179.32(18) . . . . ?
P1A C1A C10A C9A 1.7(2) . . . . ?
C2A C1A C10A C5A 0.2(2) . . . . ?
P1A C1A C10A C5A -178.78(14) . . . . ?
C1A C2A O2A C15A -165.21(19) . . . . ?
C3A C2A O2A C15A 15.1(3) . . . . ?
C12A C11A P1A O1A 176.58(15) . . . . ?
C13A C11A P1A O1A 55.74(17) . . . . ?
C14A C11A P1A O1A -61.78(16) . . . . ?
C12A C11A P1A N1A 57.73(18) . . . . ?
C13A C11A P1A N1A -63.10(17) . . . . ?
C14A C11A P1A N1A 179.37(14) . . . . ?
C12A C11A P1A C1A -60.21(17) . . . . ?
C13A C11A P1A C1A 178.96(15) . . . . ?
C14A C11A P1A C1A 61.43(16) . . . . ?
C2A C1A P1A O1A -154.36(14) . . . . ?
C10A C1A P1A O1A 24.60(17) . . . . ?
C2A C1A P1A N1A -32.79(17) . . . . ?
C10A C1A P1A N1A 146.17(14) . . . . ?
C2A C1A P1A C11A 83.84(16) . . . . ?
C10A C1A P1A C11A -97.20(15) . . . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.033


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether/dichloromethane'
