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

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

data_1_b
_database_code_depnum_ccdc_archive 'CCDC 1828164'
_audit_update_record             
;
2018-03-07 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H17 Cl N2'
_chemical_formula_weight         188.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   11.5980(17)
_cell_length_b                   9.2935(14)
_cell_length_c                   9.4641(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1020.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1237
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      22.05

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.326
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6686
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABA
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6867
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.809
_diffrn_reflns_theta_max         25.243
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             1794
_reflns_number_gt                1555
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.953

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²+1.2467P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 596 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.45(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1794
_refine_ls_number_parameters     109
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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
C1 C 0.3119(8) 0.6292(8) 0.5806(8) 0.063(2) Uani 1 1 d . . . . .
H1A H 0.3341 0.7071 0.5146 0.075 Uiso 1 1 calc R U . . .
H1B H 0.2283 0.6382 0.6001 0.075 Uiso 1 1 calc R U . . .
C2 C 0.3743(8) 0.6433(8) 0.7075(11) 0.086(3) Uani 1 1 d . . . . .
H2A H 0.3459 0.7296 0.7581 0.103 Uiso 1 1 calc R U . . .
H2B H 0.4564 0.6603 0.6839 0.103 Uiso 1 1 calc R U . . .
C3 C 0.3673(8) 0.5168(9) 0.8059(7) 0.057(2) Uani 1 1 d . . . . .
H3A H 0.4322 0.5208 0.8737 0.069 Uiso 1 1 calc R U . . .
H3B H 0.2946 0.5219 0.8603 0.069 Uiso 1 1 calc R U . . .
N3 N 0.3716(5) 0.3808(6) 0.7282(5) 0.0384(14) Uani 1 1 d . . . . .
C5 C 0.3937(7) 0.2504(8) 0.8140(7) 0.053(2) Uani 1 1 d . . . . .
H5A H 0.3364 0.1757 0.7889 0.064 Uiso 1 1 calc R U . . .
H5B H 0.3833 0.2742 0.9151 0.064 Uiso 1 1 calc R U . . .
C6 C 0.5142(8) 0.1902(10) 0.7920(8) 0.060(2) Uani 1 1 d . . . . .
H6A H 0.5693 0.2713 0.7858 0.072 Uiso 1 1 calc R U . . .
H6B H 0.5355 0.1319 0.8756 0.072 Uiso 1 1 calc R U . . .
C7 C 0.5260(6) 0.0991(7) 0.6622(11) 0.066(2) Uani 1 1 d . . . . .
H7A H 0.4727 0.0163 0.6699 0.079 Uiso 1 1 calc R U . . .
H7B H 0.6055 0.0604 0.6583 0.079 Uiso 1 1 calc R U . . .
C8 C 0.5008(7) 0.1795(8) 0.5235(8) 0.054(2) Uani 1 1 d . . . . .
H8A H 0.5549 0.2614 0.5150 0.065 Uiso 1 1 calc R U . . .
H8B H 0.5155 0.1137 0.4432 0.065 Uiso 1 1 calc R U . . .
C9 C 0.3788(7) 0.2356(7) 0.5128(7) 0.0405(16) Uani 1 1 d . . . . .
H9A H 0.3594 0.2502 0.4120 0.049 Uiso 1 1 calc R U . . .
H9B H 0.3253 0.1622 0.5511 0.049 Uiso 1 1 calc R U . . .
Cl1 Cl 0.31415(11) 0.46243(13) 0.18443(19) 0.0363(3) Uani 1 1 d . . . . .
N1 N 0.3355(5) 0.4892(7) 0.5158(6) 0.0449(16) Uani 1 1 d . . . . .
H1 H 0.3329 0.4821 0.4231 0.054 Uiso 1 1 calc R U . . .
C10 C 0.3607(6) 0.3730(7) 0.5899(6) 0.0306(14) 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
C1 C2 1.409(12) . ?
C1 N1 1.465(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.502(12) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N3 1.464(10) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N3 C10 1.316(7) . ?
N3 C5 1.481(9) . ?
C5 C6 1.520(12) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.499(12) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.539(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.512(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.485(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N1 C10 1.320(9) . ?
N1 H1 0.8800 . ?

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
C2 C1 N1 110.1(7) . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
N1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.2 . . ?
C1 C2 C3 115.3(8) . . ?
C1 C2 H2A 108.4 . . ?
C3 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
C3 C2 H2B 108.4 . . ?
H2A C2 H2B 107.5 . . ?
N3 C3 C2 111.3(6) . . ?
N3 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
N3 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C10 N3 C3 122.9(7) . . ?
C10 N3 C5 121.1(7) . . ?
C3 N3 C5 115.9(5) . . ?
N3 C5 C6 112.7(6) . . ?
N3 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N3 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 113.9(6) . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 114.1(5) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 113.7(6) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 113.3(6) . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C10 N1 C1 123.1(6) . . ?
C10 N1 H1 118.5 . . ?
C1 N1 H1 118.5 . . ?
N3 C10 N1 120.3(7) . . ?
N3 C10 C9 121.5(7) . . ?
N1 C10 C9 118.2(5) . . ?

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_AG_AG_211_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 1828166'
_audit_update_record             
;
2018-03-07 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H43 N2 P'
_chemical_formula_weight         426.60

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'

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

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

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

_cell_length_a                   14.8002(11)
_cell_length_b                   10.1736(8)
_cell_length_c                   17.7991(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.3890(10)
_cell_angle_gamma                90
_cell_volume                     2571.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4251
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.74

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6899
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25599
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.330
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4656
_reflns_number_gt                3625
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0829P)²+3.6055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4656
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0601
_refine_ls_wR_factor_ref         0.1786
_refine_ls_wR_factor_gt          0.1644
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C 0.34738(19) 0.2831(3) 0.35369(15) 0.0278(6) Uani 1 1 d . . . . .
C2 C 0.39643(19) 0.2407(3) 0.29490(16) 0.0282(6) Uani 1 1 d . . . . .
C3 C 0.4167(2) 0.2457(3) 0.16970(18) 0.0399(7) Uani 1 1 d . . . . .
H3A H 0.4022 0.3078 0.1251 0.048 Uiso 1 1 calc R U . . .
H3B H 0.3957 0.1571 0.1489 0.048 Uiso 1 1 calc R U . . .
C4 C 0.5193(3) 0.2434(4) 0.2062(2) 0.0553(10) Uani 1 1 d . . . . .
H4A H 0.5419 0.3323 0.2251 0.066 Uiso 1 1 calc R U . . .
H4B H 0.5520 0.2157 0.1673 0.066 Uiso 1 1 calc R U . . .
C5 C 0.5409(2) 0.1452(4) 0.2757(2) 0.0504(9) Uani 1 1 d . . . . .
H5A H 0.5374 0.0541 0.2554 0.060 Uiso 1 1 calc R U . . .
H5B H 0.6056 0.1603 0.3098 0.060 Uiso 1 1 calc R U . . .
C6 C 0.4993(2) 0.1076(3) 0.40022(19) 0.0458(8) Uani 1 1 d . . . . .
H6A H 0.5413 0.0312 0.4023 0.055 Uiso 1 1 calc R U . . .
H6B H 0.4416 0.0755 0.4119 0.055 Uiso 1 1 calc R U . . .
C10 C 0.19374(17) 0.3421(3) 0.40453(14) 0.0217(5) Uani 1 1 d . . . . .
C11 C 0.18573(17) 0.2772(2) 0.47316(14) 0.0216(5) Uani 1 1 d . . . . .
C12 C 0.17357(19) 0.1264(3) 0.47859(16) 0.0268(6) Uani 1 1 d . . . . .
C13 C 0.2614(2) 0.0466(3) 0.47777(19) 0.0384(7) Uani 1 1 d . . . . .
H13A H 0.2493 -0.0470 0.4835 0.058 Uiso 1 1 calc R U . . .
H13B H 0.3148 0.0749 0.5212 0.058 Uiso 1 1 calc R U . . .
H13C H 0.2760 0.0610 0.4280 0.058 Uiso 1 1 calc R U . . .
C14 C 0.0902(2) 0.0823(3) 0.40937(18) 0.0378(7) Uani 1 1 d . . . . .
H14A H 0.1060 0.0963 0.3601 0.057 Uiso 1 1 calc R U . . .
H14B H 0.0341 0.1338 0.4091 0.057 Uiso 1 1 calc R U . . .
H14C H 0.0775 -0.0112 0.4150 0.057 Uiso 1 1 calc R U . . .
C15 C 0.1491(3) 0.0877(3) 0.55388(19) 0.0425(8) Uani 1 1 d . . . . .
H15A H 0.1366 -0.0069 0.5533 0.064 Uiso 1 1 calc R U . . .
H15B H 0.0930 0.1361 0.5570 0.064 Uiso 1 1 calc R U . . .
H15C H 0.2020 0.1093 0.5994 0.064 Uiso 1 1 calc R U . . .
C16 C 0.18059(17) 0.3545(3) 0.53674(14) 0.0224(5) Uani 1 1 d . . . . .
H16 H 0.1794 0.3117 0.5839 0.027 Uiso 1 1 calc R U . . .
C17 C 0.17714(17) 0.4906(3) 0.53420(14) 0.0211(5) Uani 1 1 d . . . . .
C18 C 0.17175(19) 0.5699(3) 0.60606(15) 0.0264(6) Uani 1 1 d . . . . .
C19 C 0.0869(3) 0.5232(4) 0.6319(2) 0.0620(11) Uani 1 1 d . . . . .
H19A H 0.0293 0.5343 0.5887 0.093 Uiso 1 1 calc R U . . .
H19B H 0.0821 0.5751 0.6770 0.093 Uiso 1 1 calc R U . . .
H19C H 0.0948 0.4301 0.6466 0.093 Uiso 1 1 calc R U . . .
C20 C 0.2611(3) 0.5454(4) 0.67378(18) 0.0495(9) Uani 1 1 d . . . . .
H20A H 0.2667 0.4513 0.6862 0.074 Uiso 1 1 calc R U . . .
H20B H 0.2572 0.5948 0.7200 0.074 Uiso 1 1 calc R U . . .
H20C H 0.3165 0.5744 0.6583 0.074 Uiso 1 1 calc R U . . .
C21 C 0.1629(3) 0.7164(3) 0.5901(2) 0.0514(9) Uani 1 1 d . . . . .
H21A H 0.2169 0.7469 0.5733 0.077 Uiso 1 1 calc R U . . .
H21B H 0.1614 0.7629 0.6379 0.077 Uiso 1 1 calc R U . . .
H21C H 0.1046 0.7342 0.5487 0.077 Uiso 1 1 calc R U . . .
C22 C 0.17370(17) 0.5494(3) 0.46344(14) 0.0227(5) Uani 1 1 d . . . . .
H22 H 0.1668 0.6422 0.4595 0.027 Uiso 1 1 calc R U . . .
C23 C 0.17971(17) 0.4800(3) 0.39747(14) 0.0217(5) Uani 1 1 d . . . . .
C24 C 0.1678(2) 0.5602(3) 0.32074(15) 0.0298(6) Uani 1 1 d . . . . .
C25 C 0.1157(3) 0.6900(3) 0.32324(19) 0.0463(9) Uani 1 1 d . . . . .
H25A H 0.1007 0.7323 0.2717 0.069 Uiso 1 1 calc R U . . .
H25B H 0.1559 0.7484 0.3625 0.069 Uiso 1 1 calc R U . . .
H25C H 0.0573 0.6722 0.3371 0.069 Uiso 1 1 calc R U . . .
C26 C 0.1074(2) 0.4865(4) 0.24893(17) 0.0463(8) Uani 1 1 d . . . . .
H26A H 0.0939 0.5445 0.2031 0.070 Uiso 1 1 calc R U . . .
H26B H 0.0481 0.4591 0.2585 0.070 Uiso 1 1 calc R U . . .
H26C H 0.1416 0.4088 0.2392 0.070 Uiso 1 1 calc R U . . .
C27 C 0.2634(2) 0.5952(3) 0.3087(2) 0.0447(8) Uani 1 1 d . . . . .
H27A H 0.2934 0.5153 0.2965 0.067 Uiso 1 1 calc R U . . .
H27B H 0.3036 0.6350 0.3566 0.067 Uiso 1 1 calc R U . . .
H27C H 0.2542 0.6576 0.2652 0.067 Uiso 1 1 calc R U . . .
N1 N 0.47367(19) 0.1614(3) 0.32137(15) 0.0443(7) Uani 1 1 d . . . . .
N2 N 0.36414(17) 0.2848(2) 0.22475(14) 0.0327(6) Uani 1 1 d . . . . .
P1 P 0.23154(5) 0.25173(7) 0.32826(4) 0.0256(2) Uani 1 1 d . . . . .
C7 C 0.5486(2) 0.2060(3) 0.46347(18) 0.0414(8) Uani 1 1 d . . . . .
H7A H 0.5443 0.1747 0.5150 0.050 Uiso 0.411(10) 1 calc R U P A 1
H7B H 0.6161 0.2111 0.4656 0.050 Uiso 0.411(10) 1 calc R U P A 1
H7C H 0.5918 0.2620 0.4439 0.050 Uiso 0.589(10) 1 calc R U P A 2
H7D H 0.5862 0.1584 0.5104 0.050 Uiso 0.589(10) 1 calc R U P A 2
C9 C 0.4063(2) 0.3586(4) 0.4238(2) 0.0498(9) Uani 1 1 d . . . . .
H9A H 0.3953 0.4535 0.4125 0.060 Uiso 0.411(10) 1 calc R U P A 1
H9B H 0.3819 0.3381 0.4689 0.060 Uiso 0.411(10) 1 calc R U P A 1
H9C H 0.4402 0.4280 0.4037 0.060 Uiso 0.589(10) 1 calc R U P A 2
H9D H 0.3622 0.4038 0.4479 0.060 Uiso 0.589(10) 1 calc R U P A 2
C8 C 0.5065(5) 0.3373(8) 0.4482(5) 0.035(3) Uani 0.411(10) 1 d . . P A 1
H8A H 0.5317 0.3891 0.4966 0.042 Uiso 0.411(10) 1 calc R U P A 1
H8B H 0.5317 0.3778 0.4077 0.042 Uiso 0.411(10) 1 calc R U P A 1
C8A C 0.4739(4) 0.2921(5) 0.4850(3) 0.0320(16) Uani 0.589(10) 1 d . . P A 2
H8A1 H 0.4391 0.2356 0.5126 0.038 Uiso 0.589(10) 1 calc R U P A 2
H8A2 H 0.5076 0.3591 0.5229 0.038 Uiso 0.589(10) 1 calc R U P A 2


_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
C1 C2 1.496(4) . ?
C1 C9 1.515(4) . ?
C1 P1 1.676(3) . ?
C2 N2 1.285(4) . ?
C2 N1 1.369(4) . ?
C3 N2 1.468(4) . ?
C3 C4 1.474(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.553(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.461(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N1 1.453(4) . ?
C6 C7 1.529(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C10 C23 1.418(4) . ?
C10 C11 1.423(3) . ?
C10 P1 1.852(3) . ?
C11 C16 1.397(3) . ?
C11 C12 1.551(4) . ?
C12 C15 1.535(4) . ?
C12 C13 1.536(4) . ?
C12 C14 1.544(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.387(4) . ?
C16 H16 0.9500 . ?
C17 C22 1.382(3) . ?
C17 C18 1.533(3) . ?
C18 C21 1.517(4) . ?
C18 C19 1.530(4) . ?
C18 C20 1.538(4) . ?
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 C23 1.395(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.557(3) . ?
C24 C27 1.532(4) . ?
C24 C26 1.533(4) . ?
C24 C25 1.536(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C7 C8 1.468(8) . ?
C7 C8A 1.541(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 H7C 0.9900 . ?
C7 H7D 0.9900 . ?
C9 C8A 1.425(6) . ?
C9 C8 1.439(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 H9C 0.9900 . ?
C9 H9D 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 116.3(2) . . ?
C2 C1 P1 114.69(19) . . ?
C9 C1 P1 128.8(2) . . ?
N2 C2 N1 125.8(3) . . ?
N2 C2 C1 117.3(2) . . ?
N1 C2 C1 116.9(2) . . ?
N2 C3 C4 112.6(3) . . ?
N2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 C5 108.4(3) . . ?
C3 C4 H4A 110.0 . . ?
C5 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
C5 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
N1 C5 C4 110.6(3) . . ?
N1 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N1 C6 C7 113.9(3) . . ?
N1 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
N1 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C23 C10 C11 119.3(2) . . ?
C23 C10 P1 119.53(19) . . ?
C11 C10 P1 120.96(19) . . ?
C16 C11 C10 118.1(2) . . ?
C16 C11 C12 118.2(2) . . ?
C10 C11 C12 123.5(2) . . ?
C15 C12 C13 106.4(2) . . ?
C15 C12 C14 106.8(2) . . ?
C13 C12 C14 109.1(2) . . ?
C15 C12 C11 111.6(2) . . ?
C13 C12 C11 114.1(2) . . ?
C14 C12 C11 108.6(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C11 123.1(2) . . ?
C17 C16 H16 118.5 . . ?
C11 C16 H16 118.5 . . ?
C22 C17 C16 117.0(2) . . ?
C22 C17 C18 122.4(2) . . ?
C16 C17 C18 120.5(2) . . ?
C21 C18 C19 109.1(3) . . ?
C21 C18 C17 112.5(2) . . ?
C19 C18 C17 109.2(2) . . ?
C21 C18 C20 108.4(3) . . ?
C19 C18 C20 108.2(3) . . ?
C17 C18 C20 109.5(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 C23 123.6(2) . . ?
C17 C22 H22 118.2 . . ?
C23 C22 H22 118.2 . . ?
C22 C23 C10 117.9(2) . . ?
C22 C23 C24 117.0(2) . . ?
C10 C23 C24 125.0(2) . . ?
C27 C24 C26 109.9(3) . . ?
C27 C24 C25 107.1(3) . . ?
C26 C24 C25 105.4(2) . . ?
C27 C24 C23 111.3(2) . . ?
C26 C24 C23 111.7(2) . . ?
C25 C24 C23 111.0(2) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C2 N1 C6 121.3(3) . . ?
C2 N1 C5 120.6(3) . . ?
C6 N1 C5 117.5(3) . . ?
C2 N2 C3 115.6(2) . . ?
C1 P1 C10 101.84(12) . . ?
C8 C7 C6 111.7(3) . . ?
C6 C7 C8A 109.1(3) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C6 C7 H7C 109.9 . . ?
C8A C7 H7C 109.9 . . ?
C6 C7 H7D 109.9 . . ?
C8A C7 H7D 109.9 . . ?
H7C C7 H7D 108.3 . . ?
C8A C9 C1 120.3(3) . . ?
C8 C9 C1 118.5(4) . . ?
C8 C9 H9A 107.7 . . ?
C1 C9 H9A 107.7 . . ?
C8 C9 H9B 107.7 . . ?
C1 C9 H9B 107.7 . . ?
H9A C9 H9B 107.1 . . ?
C8A C9 H9C 107.2 . . ?
C1 C9 H9C 107.2 . . ?
C8A C9 H9D 107.2 . . ?
C1 C9 H9D 107.2 . . ?
H9C C9 H9D 106.9 . . ?
C9 C8 C7 122.7(6) . . ?
C9 C8 H8A 106.6 . . ?
C7 C8 H8A 106.6 . . ?
C9 C8 H8B 106.6 . . ?
C7 C8 H8B 106.6 . . ?
H8A C8 H8B 106.6 . . ?
C9 C8A C7 118.6(4) . . ?
C9 C8A H8A1 107.7 . . ?
C7 C8A H8A1 107.7 . . ?
C9 C8A H8A2 107.7 . . ?
C7 C8A H8A2 107.7 . . ?
H8A1 C8A H8A2 107.1 . . ?

_refine_diff_density_max         0.957
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1828165'
_audit_update_record             
;
2018-03-07 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H44 F3 N2 O3 P S'
_chemical_formula_weight         576.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   17.1251(14)
_cell_length_b                   8.5823(6)
_cell_length_c                   20.7780(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.750(5)
_cell_angle_gamma                90
_cell_volume                     3032.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2460
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      22.09

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.209
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6037
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18447
_diffrn_reflns_av_unetI/netI     0.0714
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.974
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             5434
_reflns_number_gt                3707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0828P)²+3.7672P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5434
_refine_ls_number_parameters     412
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1894
_refine_ls_wR_factor_gt          0.1672
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
P1 P 0.71988(5) 0.48004(11) 0.40454(4) 0.0233(3) Uani 1 1 d . . . . .
N1 N 0.7743(2) 0.3386(4) 0.28063(15) 0.0317(8) Uani 1 1 d . . . . .
N2 N 0.89359(17) 0.2994(4) 0.34285(16) 0.0310(8) Uani 1 1 d . . . . .
C1 C 0.77589(19) 0.3207(4) 0.39671(18) 0.0252(8) Uani 1 1 d . . . . .
C2 C 0.8162(2) 0.3206(4) 0.33727(18) 0.0241(8) Uani 1 1 d . . . . .
C3 C 0.8094(2) 0.3486(6) 0.22018(19) 0.0452(12) Uani 1 1 d . . . . .
H3A H 0.8249 0.4574 0.2123 0.054 Uiso 1 1 calc R U . . .
H3B H 0.7711 0.3149 0.1835 0.054 Uiso 1 1 calc R U . . .
C4 C 0.8807(3) 0.2441(5) 0.2257(2) 0.0476(12) Uani 1 1 d . . . . .
H4A H 0.8639 0.1340 0.2276 0.057 Uiso 1 1 calc R U . . .
H4B H 0.9085 0.2570 0.1869 0.057 Uiso 1 1 calc R U . . .
C5 C 0.9355(2) 0.2823(5) 0.2851(2) 0.0402(11) Uani 1 1 d . . . . .
H5A H 0.9752 0.1985 0.2930 0.048 Uiso 1 1 calc R U . . .
H5B H 0.9635 0.3805 0.2779 0.048 Uiso 1 1 calc R U . . .
C6 C 0.9427(2) 0.3215(5) 0.4049(2) 0.0401(11) Uani 1 1 d . . . . .
H6A H 0.9253 0.4167 0.4260 0.048 Uiso 1 1 calc R U . . .
H6B H 0.9978 0.3379 0.3965 0.048 Uiso 1 1 calc R U . . .
C7 C 0.9399(2) 0.1842(6) 0.4513(2) 0.0525(13) Uani 1 1 d . . . . .
H7A H 0.9867 0.1880 0.4841 0.063 Uiso 1 1 calc R U . . .
H7B H 0.9421 0.0858 0.4267 0.063 Uiso 1 1 calc R U . . .
C8 C 0.8658(2) 0.1843(6) 0.4857(2) 0.0443(12) Uani 1 1 d . . . . .
H8A H 0.8672 0.0926 0.5148 0.053 Uiso 1 1 calc R U . . .
H8B H 0.8658 0.2789 0.5129 0.053 Uiso 1 1 calc R U . . .
C9 C 0.7899(2) 0.1800(5) 0.4393(2) 0.0317(9) Uani 1 1 d . . . . .
H9A H 0.7908 0.0866 0.4114 0.038 Uiso 1 1 calc R U . . .
H9B H 0.7451 0.1684 0.4650 0.038 Uiso 1 1 calc R U . . .
C10 C 0.68253(19) 0.4417(4) 0.48276(17) 0.0222(8) Uani 1 1 d . . . . .
C11 C 0.62199(19) 0.3315(4) 0.48842(17) 0.0215(8) Uani 1 1 d . . . . .
C12 C 0.61622(19) 0.2671(4) 0.54926(16) 0.0213(8) Uani 1 1 d . . . . .
H12 H 0.5786 0.1872 0.5529 0.026 Uiso 1 1 calc R U . . .
C13 C 0.6628(2) 0.3146(4) 0.60429(17) 0.0242(8) Uani 1 1 d . . . . .
C14 C 0.7118(2) 0.4420(4) 0.59848(17) 0.0255(8) Uani 1 1 d . . . . .
H14 H 0.7395 0.4845 0.6368 0.031 Uiso 1 1 calc R U . . .
C15 C 0.7224(2) 0.5098(4) 0.53960(17) 0.0243(8) Uani 1 1 d . . . . .
C16 C 0.5607(2) 0.2804(4) 0.43089(17) 0.0241(8) Uani 1 1 d . . . . .
C17 C 0.5882(2) 0.1375(5) 0.3956(2) 0.0367(10) Uani 1 1 d . . . . .
H17A H 0.5997 0.0522 0.4266 0.055 Uiso 1 1 calc R U . . .
H17B H 0.6357 0.1638 0.3758 0.055 Uiso 1 1 calc R U . . .
H17C H 0.5466 0.1051 0.3618 0.055 Uiso 1 1 calc R U . . .
C18 C 0.5415(2) 0.4140(5) 0.38224(19) 0.0345(10) Uani 1 1 d . . . . .
H18A H 0.4955 0.3858 0.3519 0.052 Uiso 1 1 calc R U . . .
H18B H 0.5866 0.4323 0.3582 0.052 Uiso 1 1 calc R U . . .
H18C H 0.5301 0.5089 0.4056 0.052 Uiso 1 1 calc R U . . .
C19 C 0.4824(2) 0.2423(5) 0.4561(2) 0.0372(10) Uani 1 1 d . . . . .
H19A H 0.4422 0.2224 0.4194 0.056 Uiso 1 1 calc R U . . .
H19B H 0.4661 0.3305 0.4814 0.056 Uiso 1 1 calc R U . . .
H19C H 0.4887 0.1495 0.4838 0.056 Uiso 1 1 calc R U . . .
C20 C 0.6608(2) 0.2371(4) 0.67021(18) 0.0282(9) Uani 1 1 d . . . . .
C21 C 0.6093(4) 0.0919(6) 0.6667(2) 0.0688(17) Uani 1 1 d . . . . .
H21A H 0.6297 0.0153 0.6380 0.103 Uiso 1 1 calc R U . . .
H21B H 0.5553 0.1198 0.6498 0.103 Uiso 1 1 calc R U . . .
H21C H 0.6099 0.0473 0.7102 0.103 Uiso 1 1 calc R U . . .
C22 C 0.6244(3) 0.3536(6) 0.7154(2) 0.0486(12) Uani 1 1 d . . . . .
H22A H 0.6211 0.3045 0.7576 0.073 Uiso 1 1 calc R U . . .
H22B H 0.5715 0.3832 0.6959 0.073 Uiso 1 1 calc R U . . .
H22C H 0.6575 0.4468 0.7213 0.073 Uiso 1 1 calc R U . . .
C23 C 0.7433(3) 0.2006(7) 0.7005(2) 0.0554(14) Uani 1 1 d . . . . .
H23A H 0.7415 0.1558 0.7437 0.083 Uiso 1 1 calc R U . . .
H23B H 0.7745 0.2966 0.7042 0.083 Uiso 1 1 calc R U . . .
H23C H 0.7675 0.1258 0.6732 0.083 Uiso 1 1 calc R U . . .
C24 C 0.7719(2) 0.6619(5) 0.53905(19) 0.0338(10) Uani 1 1 d . . . . .
C25 C 0.7255(3) 0.7872(5) 0.4988(2) 0.0416(11) Uani 1 1 d . . . . .
H25A H 0.7550 0.8852 0.5022 0.062 Uiso 1 1 calc R U . . .
H25B H 0.6745 0.8025 0.5150 0.062 Uiso 1 1 calc R U . . .
H25C H 0.7171 0.7543 0.4533 0.062 Uiso 1 1 calc R U . . .
C26 C 0.8511(2) 0.6356(6) 0.5130(2) 0.0449(11) Uani 1 1 d . . . . .
H26A H 0.8419 0.5983 0.4682 0.067 Uiso 1 1 calc R U . . .
H26B H 0.8815 0.5578 0.5399 0.067 Uiso 1 1 calc R U . . .
H26C H 0.8803 0.7339 0.5144 0.067 Uiso 1 1 calc R U . . .
C27 C 0.7907(3) 0.7292(5) 0.6080(2) 0.0551(14) Uani 1 1 d . . . . .
H27A H 0.8190 0.8281 0.6060 0.083 Uiso 1 1 calc R U . . .
H27B H 0.8236 0.6553 0.6351 0.083 Uiso 1 1 calc R U . . .
H27C H 0.7416 0.7470 0.6269 0.083 Uiso 1 1 calc R U . . .
S1 S 0.58682(6) 0.27546(12) 0.18084(5) 0.0344(3) Uani 1 1 d . . . . .
C1C C 0.4810(3) 0.2726(6) 0.1797(2) 0.0462(12) Uani 1 1 d . . . . .
F1 F 0.4469(5) 0.1593(11) 0.1435(7) 0.076(5) Uani 0.54(3) 1 d D . P A 1
F2 F 0.4469(5) 0.4018(11) 0.1566(7) 0.070(4) Uani 0.54(3) 1 d D . P A 1
F3 F 0.4564(6) 0.254(2) 0.2378(4) 0.086(6) Uani 0.54(3) 1 d D . P A 1
F1A F 0.4483(8) 0.263(5) 0.1203(5) 0.168(14) Uani 0.46(3) 1 d D . P A 2
F2A F 0.4559(8) 0.4035(13) 0.2020(15) 0.106(8) Uani 0.46(3) 1 d D . P A 2
F3A F 0.4580(7) 0.1640(18) 0.2120(13) 0.105(9) Uani 0.46(3) 1 d D . P A 2
O1 O 0.6108(6) 0.1290(11) 0.2047(10) 0.123(8) Uani 0.59(2) 1 d D . P B 1
O2 O 0.5946(5) 0.297(2) 0.1152(3) 0.106(7) Uani 0.59(2) 1 d D . P B 1
O3 O 0.6094(4) 0.3986(11) 0.2230(6) 0.064(4) Uani 0.59(2) 1 d D . P B 1
O1A O 0.6136(5) 0.276(3) 0.2481(4) 0.079(9) Uani 0.41(2) 1 d D . P B 2
O2A O 0.6070(6) 0.4087(15) 0.1467(9) 0.082(8) Uani 0.41(2) 1 d D . P B 2
O3A O 0.6042(8) 0.1355(17) 0.1519(9) 0.078(6) Uani 0.41(2) 1 d D . P B 2
H1A H 0.723(2) 0.339(5) 0.2787(18) 0.032(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.689(4) . ?
P1 C10 1.845(4) . ?
N1 C2 1.313(5) . ?
N1 C3 1.458(5) . ?
N1 H1A 0.87(4) . ?
N2 C2 1.330(4) . ?
N2 C6 1.466(5) . ?
N2 C5 1.476(5) . ?
C1 C2 1.484(5) . ?
C1 C9 1.501(5) . ?
C3 C4 1.509(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.496(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.526(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.528(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.525(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.418(5) . ?
C10 C11 1.419(5) . ?
C11 C12 1.394(5) . ?
C11 C16 1.558(5) . ?
C12 C13 1.377(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(5) . ?
C13 C20 1.527(5) . ?
C14 C15 1.385(5) . ?
C14 H14 0.9500 . ?
C15 C24 1.558(5) . ?
C16 C17 1.531(5) . ?
C16 C19 1.532(5) . ?
C16 C18 1.538(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C23 1.512(6) . ?
C20 C21 1.522(6) . ?
C20 C22 1.552(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.528(6) . ?
C24 C26 1.533(6) . ?
C24 C27 1.544(6) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
S1 O3A 1.391(11) . ?
S1 O1 1.395(9) . ?
S1 O3 1.398(6) . ?
S1 O2 1.399(7) . ?
S1 O2A 1.410(8) . ?
S1 O1A 1.419(7) . ?
S1 C1C 1.809(5) . ?
C1C F3A 1.240(11) . ?
C1C F1A 1.296(11) . ?
C1C F2A 1.308(12) . ?
C1C F2 1.317(9) . ?
C1C F1 1.323(9) . ?
C1C F3 1.333(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C10 101.55(17) . . ?
C2 N1 C3 122.8(3) . . ?
C2 N1 H1A 119(3) . . ?
C3 N1 H1A 118(3) . . ?
C2 N2 C6 121.5(3) . . ?
C2 N2 C5 121.2(3) . . ?
C6 N2 C5 116.3(3) . . ?
C2 C1 C9 115.6(3) . . ?
C2 C1 P1 114.0(3) . . ?
C9 C1 P1 130.4(3) . . ?
N1 C2 N2 121.9(3) . . ?
N1 C2 C1 119.2(3) . . ?
N2 C2 C1 118.9(3) . . ?
N1 C3 C4 108.2(4) . . ?
N1 C3 H3A 110.1 . . ?
C4 C3 H3A 110.1 . . ?
N1 C3 H3B 110.1 . . ?
C4 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C5 C4 C3 110.9(3) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N2 C5 C4 112.0(3) . . ?
N2 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N2 C6 C7 113.4(4) . . ?
N2 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N2 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 112.7(4) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C7 113.4(4) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C1 C9 C8 114.8(3) . . ?
C1 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C1 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C15 C10 C11 119.4(3) . . ?
C15 C10 P1 118.5(2) . . ?
C11 C10 P1 121.6(3) . . ?
C12 C11 C10 118.0(3) . . ?
C12 C11 C16 118.1(3) . . ?
C10 C11 C16 123.8(3) . . ?
C13 C12 C11 122.7(3) . . ?
C13 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C12 C13 C14 117.2(3) . . ?
C12 C13 C20 122.9(3) . . ?
C14 C13 C20 119.9(3) . . ?
C15 C14 C13 123.3(3) . . ?
C15 C14 H14 118.4 . . ?
C13 C14 H14 118.4 . . ?
C14 C15 C10 117.6(3) . . ?
C14 C15 C24 119.1(3) . . ?
C10 C15 C24 123.2(3) . . ?
C17 C16 C19 108.9(3) . . ?
C17 C16 C18 109.7(3) . . ?
C19 C16 C18 104.8(3) . . ?
C17 C16 C11 112.1(3) . . ?
C19 C16 C11 109.6(3) . . ?
C18 C16 C11 111.6(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C23 C20 C21 111.0(4) . . ?
C23 C20 C13 110.2(3) . . ?
C21 C20 C13 112.9(3) . . ?
C23 C20 C22 107.7(4) . . ?
C21 C20 C22 106.5(4) . . ?
C13 C20 C22 108.4(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C26 109.6(3) . . ?
C25 C24 C27 106.5(4) . . ?
C26 C24 C27 106.6(4) . . ?
C25 C24 C15 110.2(3) . . ?
C26 C24 C15 112.6(3) . . ?
C27 C24 C15 111.2(3) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O1 S1 O3 114.3(6) . . ?
O1 S1 O2 114.0(7) . . ?
O3 S1 O2 117.5(7) . . ?
O3A S1 O2A 113.9(7) . . ?
O3A S1 O1A 111.5(9) . . ?
O2A S1 O1A 115.1(8) . . ?
O3A S1 C1C 104.3(6) . . ?
O1 S1 C1C 104.1(5) . . ?
O3 S1 C1C 102.8(3) . . ?
O2 S1 C1C 101.5(4) . . ?
O2A S1 C1C 107.9(5) . . ?
O1A S1 C1C 102.8(4) . . ?
F3A C1C F1A 110.0(11) . . ?
F3A C1C F2A 108.4(9) . . ?
F1A C1C F2A 105.4(11) . . ?
F2 C1C F1 105.3(6) . . ?
F2 C1C F3 104.7(7) . . ?
F1 C1C F3 105.3(7) . . ?
F3A C1C S1 112.6(6) . . ?
F1A C1C S1 109.5(7) . . ?
F2A C1C S1 110.8(7) . . ?
F2 C1C S1 113.2(5) . . ?
F1 C1C S1 113.1(5) . . ?
F3 C1C S1 114.3(5) . . ?

_refine_diff_density_max         1.248
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1828169'
_audit_update_record             
;
2018-03-07 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C55 H90 Cl2 F12 N4 P4'
_chemical_formula_weight         1230.08

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   28.528(5)
_cell_length_b                   8.5749(15)
_cell_length_c                   27.535(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.543(3)
_cell_angle_gamma                90
_cell_volume                     6077.4(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5270
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      24.86

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             2600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.288
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5338
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47806
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_av_R_equivalents  0.0975
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         0.791
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10694
_reflns_number_gt                6946
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0942P)²+23.1852P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10694
_refine_ls_number_parameters     720
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0804
_refine_ls_wR_factor_ref         0.2261
_refine_ls_wR_factor_gt          0.1960
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.08207(5) 0.66621(16) 0.19145(5) 0.0166(3) Uani 1 1 d . . . . .
P2 P 0.42294(5) 0.70828(16) 0.31190(5) 0.0174(3) Uani 1 1 d . . . . .
N1 N -0.00312(16) 0.8026(5) 0.22177(18) 0.0218(10) Uani 1 1 d . . . . .
N2 N -0.05377(14) 0.8178(5) 0.13014(16) 0.0154(9) Uani 1 1 d . . . . .
N3 N 0.50309(15) 0.5699(5) 0.27556(17) 0.0207(10) Uani 1 1 d D . . . .
N4 N 0.55695(14) 0.5508(5) 0.36612(16) 0.0189(9) Uani 1 1 d . . . . .
C1 C 0.04077(18) 0.8174(6) 0.1639(2) 0.0198(11) Uani 1 1 d . . . . .
C2 C -0.00787(17) 0.8105(6) 0.1723(2) 0.0171(11) Uani 1 1 d . . . . .
C3 C -0.04828(19) 0.7914(7) 0.2337(2) 0.0248(12) Uani 1 1 d . . . . .
H3A H -0.0392 0.8284 0.2707 0.030 Uiso 1 1 calc R U . . .
H3B H -0.0601 0.6818 0.2307 0.030 Uiso 1 1 calc R U . . .
C4 C -0.09100(18) 0.8929(7) 0.1930(2) 0.0233(12) Uani 1 1 d . . . . .
H4A H -0.1229 0.8842 0.1986 0.028 Uiso 1 1 calc R U . . .
H4B H -0.0799 1.0035 0.1978 0.028 Uiso 1 1 calc R U . . .
C5 C -0.10198(17) 0.8395(6) 0.1365(2) 0.0199(11) Uani 1 1 d . . . . .
H5A H -0.1214 0.7399 0.1288 0.024 Uiso 1 1 calc R U . . .
H5B H -0.1241 0.9179 0.1102 0.024 Uiso 1 1 calc R U . . .
C6 C -0.05970(19) 0.7932(6) 0.07508(19) 0.0207(11) Uani 1 1 d . . . . .
H6A H -0.0965 0.7686 0.0516 0.025 Uiso 1 1 calc R U . . .
H6B H -0.0386 0.7019 0.0748 0.025 Uiso 1 1 calc R U . . .
C7 C -0.04344(18) 0.9332(6) 0.0517(2) 0.0216(12) Uani 1 1 d . . . . .
H7A H -0.0569 1.0295 0.0610 0.026 Uiso 1 1 calc R U . . .
H7B H -0.0595 0.9242 0.0120 0.026 Uiso 1 1 calc R U . . .
C8 C 0.01541(19) 0.9477(7) 0.0721(2) 0.0237(12) Uani 1 1 d . . . . .
H8A H 0.0230 1.0424 0.0561 0.028 Uiso 1 1 calc R U . . .
H8B H 0.0282 0.8568 0.0591 0.028 Uiso 1 1 calc R U . . .
C9 C 0.04574(18) 0.9572(6) 0.1336(2) 0.0192(11) Uani 1 1 d . . . . .
H9A H 0.0830 0.9727 0.1426 0.023 Uiso 1 1 calc R U . . .
H9B H 0.0338 1.0503 0.1463 0.023 Uiso 1 1 calc R U . . .
C10 C 0.13489(17) 0.7141(5) 0.17207(18) 0.0131(10) Uani 1 1 d . . . . .
C11 C 0.13393(17) 0.6438(6) 0.12495(19) 0.0164(11) Uani 1 1 d . . . . .
C12 C 0.10603(18) 0.4876(6) 0.1015(2) 0.0190(11) Uani 1 1 d . . . . .
C13 C 0.1200(2) 0.3640(7) 0.1457(2) 0.0314(14) Uani 1 1 d . . . . .
H13A H 0.1058 0.3947 0.1710 0.047 Uiso 1 1 calc R U . . .
H13B H 0.1579 0.3549 0.1649 0.047 Uiso 1 1 calc R U . . .
H13C H 0.1052 0.2634 0.1294 0.047 Uiso 1 1 calc R U . . .
C14 C 0.0473(2) 0.5036(7) 0.0713(2) 0.0386(16) Uani 1 1 d . . . . .
H14A H 0.0323 0.4046 0.0537 0.058 Uiso 1 1 calc R U . . .
H14B H 0.0387 0.5858 0.0441 0.058 Uiso 1 1 calc R U . . .
H14C H 0.0329 0.5309 0.0967 0.058 Uiso 1 1 calc R U . . .
C15 C 0.1245(3) 0.4197(7) 0.0602(3) 0.0415(16) Uani 1 1 d . . . . .
H15A H 0.1114 0.3130 0.0507 0.062 Uiso 1 1 calc R U . . .
H15B H 0.1625 0.4190 0.0761 0.062 Uiso 1 1 calc R U . . .
H15C H 0.1111 0.4845 0.0276 0.062 Uiso 1 1 calc R U . . .
C16 C 0.16214(17) 0.7165(6) 0.10072(19) 0.0184(11) Uani 1 1 d . . . . .
H16 H 0.1608 0.6733 0.0684 0.022 Uiso 1 1 calc R U . . .
C17 C 0.19230(17) 0.8495(6) 0.12165(19) 0.0160(11) Uani 1 1 d . . . . .
C18 C 0.21972(19) 0.9277(6) 0.0910(2) 0.0208(11) Uani 1 1 d . . . . .
C19 C 0.1789(2) 0.9757(7) 0.0351(2) 0.0307(14) Uani 1 1 d . . . . .
H19A H 0.1596 0.8833 0.0158 0.046 Uiso 1 1 calc R U . . .
H19B H 0.1962 1.0237 0.0149 0.046 Uiso 1 1 calc R U . . .
H19C H 0.1548 1.0508 0.0389 0.046 Uiso 1 1 calc R U . . .
C20 C 0.2587(2) 0.8152(8) 0.0854(2) 0.0354(15) Uani 1 1 d . . . . .
H20A H 0.2873 0.7959 0.1209 0.053 Uiso 1 1 calc R U . . .
H20B H 0.2726 0.8611 0.0617 0.053 Uiso 1 1 calc R U . . .
H20C H 0.2413 0.7165 0.0700 0.053 Uiso 1 1 calc R U . . .
C21 C 0.2492(2) 1.0754(7) 0.1194(2) 0.0313(14) Uani 1 1 d . . . . .
H21A H 0.2250 1.1487 0.1239 0.047 Uiso 1 1 calc R U . . .
H21B H 0.2647 1.1241 0.0976 0.047 Uiso 1 1 calc R U . . .
H21C H 0.2766 1.0476 0.1547 0.047 Uiso 1 1 calc R U . . .
C22 C 0.19803(16) 0.8990(6) 0.17168(19) 0.0142(10) Uani 1 1 d . . . . .
H22 H 0.2214 0.9823 0.1886 0.017 Uiso 1 1 calc R U . . .
C23 C 0.17113(17) 0.8328(6) 0.19873(18) 0.0136(10) Uani 1 1 d . . . . .
C24 C 0.18518(17) 0.8886(6) 0.2571(2) 0.0180(11) Uani 1 1 d . . . . .
C25 C 0.24210(19) 0.9430(8) 0.2844(2) 0.0333(15) Uani 1 1 d . . . . .
H25A H 0.2458 1.0400 0.2675 0.050 Uiso 1 1 calc R U . . .
H25B H 0.2645 0.8625 0.2803 0.050 Uiso 1 1 calc R U . . .
H25C H 0.2522 0.9613 0.3227 0.050 Uiso 1 1 calc R U . . .
C26 C 0.1821(2) 0.7538(6) 0.2922(2) 0.0241(12) Uani 1 1 d . . . . .
H26A H 0.1963 0.7876 0.3298 0.036 Uiso 1 1 calc R U . . .
H26B H 0.2022 0.6650 0.2890 0.036 Uiso 1 1 calc R U . . .
H26C H 0.1457 0.7226 0.2802 0.036 Uiso 1 1 calc R U . . .
C27 C 0.1510(2) 1.0231(7) 0.2583(2) 0.0277(13) Uani 1 1 d . . . . .
H27A H 0.1625 1.0591 0.2955 0.042 Uiso 1 1 calc R U . . .
H27B H 0.1148 0.9879 0.2442 0.042 Uiso 1 1 calc R U . . .
H27C H 0.1536 1.1089 0.2361 0.042 Uiso 1 1 calc R U . . .
C28 C 0.46383(18) 0.5560(6) 0.3372(2) 0.0176(11) Uani 1 1 d . . . . .
C29 C 0.51023(18) 0.5607(6) 0.3259(2) 0.0185(11) Uani 1 1 d . . . . .
C30 C 0.5463(2) 0.5822(7) 0.2603(2) 0.0281(13) Uani 1 1 d . . . . .
H30A H 0.5571 0.6924 0.2616 0.034 Uiso 1 1 calc R U . . .
H30B H 0.5356 0.5426 0.2233 0.034 Uiso 1 1 calc R U . . .
C31 C 0.5913(2) 0.4844(7) 0.3004(2) 0.0275(13) Uani 1 1 d . . . . .
H31A H 0.5815 0.3728 0.2959 0.033 Uiso 1 1 calc R U . . .
H31B H 0.6222 0.4975 0.2933 0.033 Uiso 1 1 calc R U . . .
C32 C 0.60406(19) 0.5343(7) 0.3569(2) 0.0268(13) Uani 1 1 d . . . . .
H32A H 0.6275 0.4564 0.3823 0.032 Uiso 1 1 calc R U . . .
H32B H 0.6227 0.6353 0.3641 0.032 Uiso 1 1 calc R U . . .
C33 C 0.56507(19) 0.5758(7) 0.4221(2) 0.0235(12) Uani 1 1 d . . . . .
H33A H 0.5444 0.6674 0.4232 0.028 Uiso 1 1 calc R U . . .
H33B H 0.6021 0.6009 0.4442 0.028 Uiso 1 1 calc R U . . .
C34 C 0.55057(19) 0.4391(7) 0.4471(2) 0.0252(12) Uani 1 1 d . . . . .
H34A H 0.5686 0.4487 0.4867 0.030 Uiso 1 1 calc R U . . .
H34B H 0.5629 0.3420 0.4368 0.030 Uiso 1 1 calc R U . . .
C35 C 0.49218(19) 0.4264(6) 0.4299(2) 0.0213(11) Uani 1 1 d . . . . .
H35A H 0.4807 0.5186 0.4435 0.026 Uiso 1 1 calc R U . . .
H35B H 0.4854 0.3327 0.4469 0.026 Uiso 1 1 calc R U . . .
C36 C 0.45993(18) 0.4158(6) 0.3690(2) 0.0187(11) Uani 1 1 d . . . . .
H36A H 0.4709 0.3219 0.3557 0.022 Uiso 1 1 calc R U . . .
H36B H 0.4230 0.4013 0.3616 0.022 Uiso 1 1 calc R U . . .
C37 C 0.37272(17) 0.6651(6) 0.33534(19) 0.0156(10) Uani 1 1 d . . . . .
C38 C 0.37576(17) 0.7416(6) 0.38213(19) 0.0151(10) Uani 1 1 d . . . . .
C39 C 0.40616(19) 0.8954(6) 0.4048(2) 0.0214(12) Uani 1 1 d . . . . .
C40 C 0.3875(2) 1.0200(6) 0.3606(2) 0.0289(13) Uani 1 1 d . . . . .
H40A H 0.3499 1.0342 0.3473 0.043 Uiso 1 1 calc R U . . .
H40B H 0.3955 0.9868 0.3309 0.043 Uiso 1 1 calc R U . . .
H40C H 0.4052 1.1188 0.3753 0.043 Uiso 1 1 calc R U . . .
C41 C 0.46549(19) 0.8786(7) 0.4278(2) 0.0296(13) Uani 1 1 d . . . . .
H41A H 0.4752 0.8517 0.3988 0.044 Uiso 1 1 calc R U . . .
H41B H 0.4771 0.7960 0.4551 0.044 Uiso 1 1 calc R U . . .
H41C H 0.4820 0.9774 0.4443 0.044 Uiso 1 1 calc R U . . .
C42 C 0.3964(2) 0.9602(7) 0.4516(2) 0.0317(14) Uani 1 1 d . . . . .
H42A H 0.4146 1.0599 0.4635 0.048 Uiso 1 1 calc R U . . .
H42B H 0.4093 0.8859 0.4816 0.048 Uiso 1 1 calc R U . . .
H42C H 0.3590 0.9763 0.4396 0.048 Uiso 1 1 calc R U . . .
C43 C 0.34725(17) 0.6771(6) 0.4080(2) 0.0179(11) Uani 1 1 d . . . . .
H43 H 0.3495 0.7247 0.4400 0.021 Uiso 1 1 calc R U . . .
C44 C 0.31611(17) 0.5471(6) 0.38849(19) 0.0171(11) Uani 1 1 d . . . . .
C45 C 0.29233(19) 0.4624(6) 0.4220(2) 0.0215(12) Uani 1 1 d . . . . .
C46 C 0.3253(2) 0.3131(7) 0.4434(2) 0.0311(14) Uani 1 1 d . . . . .
H46A H 0.3204 0.2445 0.4131 0.047 Uiso 1 1 calc R U . . .
H46B H 0.3143 0.2587 0.4680 0.047 Uiso 1 1 calc R U . . .
H46C H 0.3620 0.3415 0.4626 0.047 Uiso 1 1 calc R U . . .
C47 C 0.2962(2) 0.5582(7) 0.4704(2) 0.0342(14) Uani 1 1 d . . . . .
H47A H 0.2848 0.4946 0.4929 0.051 Uiso 1 1 calc R U . . .
H47B H 0.2739 0.6506 0.4578 0.051 Uiso 1 1 calc R U . . .
H47C H 0.3322 0.5909 0.4916 0.051 Uiso 1 1 calc R U . . .
C48 C 0.2355(2) 0.4180(8) 0.3874(2) 0.0375(16) Uani 1 1 d . . . . .
H48A H 0.2334 0.3486 0.3583 0.056 Uiso 1 1 calc R U . . .
H48B H 0.2152 0.5125 0.3721 0.056 Uiso 1 1 calc R U . . .
H48C H 0.2215 0.3644 0.4098 0.056 Uiso 1 1 calc R U . . .
C49 C 0.30850(17) 0.4892(6) 0.33868(19) 0.0163(11) Uani 1 1 d . . . . .
H49 H 0.2846 0.4060 0.3235 0.020 Uiso 1 1 calc R U . . .
C50 C 0.33464(17) 0.5486(6) 0.30990(19) 0.0156(11) Uani 1 1 d . . . . .
C51 C 0.31866(18) 0.4876(6) 0.2519(2) 0.0189(11) Uani 1 1 d . . . . .
C52 C 0.35331(19) 0.3550(6) 0.2490(2) 0.0244(12) Uani 1 1 d . . . . .
H52A H 0.3542 0.2713 0.2737 0.037 Uiso 1 1 calc R U . . .
H52B H 0.3886 0.3944 0.2594 0.037 Uiso 1 1 calc R U . . .
H52C H 0.3393 0.3144 0.2122 0.037 Uiso 1 1 calc R U . . .
C53 C 0.3182(2) 0.6210(7) 0.2145(2) 0.0269(13) Uani 1 1 d . . . . .
H53A H 0.3032 0.5838 0.1772 0.040 Uiso 1 1 calc R U . . .
H53B H 0.3538 0.6570 0.2248 0.040 Uiso 1 1 calc R U . . .
H53C H 0.2972 0.7075 0.2177 0.040 Uiso 1 1 calc R U . . .
C54 C 0.2626(2) 0.4263(8) 0.2275(2) 0.0332(14) Uani 1 1 d . . . . .
H54A H 0.2517 0.4013 0.1894 0.050 Uiso 1 1 calc R U . . .
H54B H 0.2396 0.5063 0.2307 0.050 Uiso 1 1 calc R U . . .
H54C H 0.2608 0.3322 0.2468 0.050 Uiso 1 1 calc R U . . .
C1S C 0.2400(3) -0.0302(8) 0.4824(3) 0.0479(18) Uani 1 1 d . . . . .
H1S1 H 0.2742 -0.0689 0.5090 0.057 Uiso 1 1 calc R U . . .
H1S2 H 0.2136 -0.1087 0.4798 0.057 Uiso 1 1 calc R U . . .
Cl1S Cl 0.22598(8) 0.1455(2) 0.50634(8) 0.0596(5) Uani 1 1 d . . . . .
Cl2S Cl 0.24131(7) -0.0144(2) 0.42126(7) 0.0508(5) Uani 1 1 d . . . . .
P1C P 0.08056(5) 0.84264(16) 0.37937(6) 0.0223(3) Uani 1 1 d . . . . .
F1C F 0.08960(13) 0.8649(5) 0.32661(14) 0.0496(10) Uani 1 1 d . . . . .
F2C F 0.04220(12) 0.7009(4) 0.35025(14) 0.0383(9) Uani 1 1 d . . . . .
F3C F 0.03254(12) 0.9598(4) 0.35453(15) 0.0455(10) Uani 1 1 d . . . . .
F4C F 0.07002(17) 0.8181(5) 0.43128(15) 0.0604(12) Uani 1 1 d . . . . .
F5C F 0.11805(14) 0.9834(4) 0.40789(15) 0.0481(10) Uani 1 1 d . . . . .
F6C F 0.12766(13) 0.7243(4) 0.40349(14) 0.0461(10) Uani 1 1 d . . . . .
P2C P 0.40786(6) 0.52419(18) 0.12062(6) 0.0276(4) Uani 1 1 d . . . . .
F7C F 0.4066(3) 0.4488(10) 0.07034(19) 0.152(4) Uani 1 1 d . . . . .
F8C F 0.45563(17) 0.6242(7) 0.1303(3) 0.143(3) Uani 1 1 d . . . . .
F9C F 0.44674(17) 0.3918(4) 0.15682(16) 0.0649(13) Uani 1 1 d . . . . .
F10C F 0.40897(19) 0.5922(9) 0.17396(18) 0.114(2) Uani 1 1 d . . . . .
F11C F 0.35979(19) 0.4241(7) 0.1133(2) 0.118(3) Uani 1 1 d . . . . .
F12C F 0.37000(14) 0.6570(5) 0.08592(18) 0.0605(12) Uani 1 1 d . . . . .
H3H H 0.4712(13) 0.554(10) 0.251(2) 0.08(3) Uiso 1 1 d D . . . .
H1H H 0.027(2) 0.820(7) 0.247(2) 0.030(16) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.695(5) . ?
P1 C10 1.849(5) . ?
P2 C28 1.688(5) . ?
P2 C37 1.845(5) . ?
N1 C2 1.312(6) . ?
N1 C3 1.463(6) . ?
N1 H1H 0.85(6) . ?
N2 C2 1.324(6) . ?
N2 C6 1.466(6) . ?
N2 C5 1.472(6) . ?
N3 C29 1.314(6) . ?
N3 C30 1.467(6) . ?
N3 H3H 0.88(2) . ?
N4 C29 1.318(6) . ?
N4 C33 1.472(6) . ?
N4 C32 1.479(6) . ?
C1 C2 1.502(6) . ?
C1 C9 1.503(7) . ?
C3 C4 1.524(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.518(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.525(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.529(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.536(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C23 1.410(7) . ?
C10 C11 1.420(7) . ?
C11 C16 1.395(7) . ?
C11 C12 1.549(7) . ?
C12 C14 1.523(7) . ?
C12 C13 1.532(7) . ?
C12 C15 1.557(7) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.395(7) . ?
C16 H16 0.9500 . ?
C17 C22 1.382(7) . ?
C17 C18 1.532(7) . ?
C18 C20 1.530(7) . ?
C18 C19 1.531(7) . ?
C18 C21 1.534(8) . ?
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 C23 1.400(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.554(7) . ?
C24 C27 1.520(7) . ?
C24 C26 1.534(7) . ?
C24 C25 1.539(7) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.484(6) . ?
C28 C36 1.520(7) . ?
C30 C31 1.532(8) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.497(8) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.504(8) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.527(7) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.528(7) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.415(7) . ?
C37 C50 1.418(7) . ?
C38 C43 1.404(7) . ?
C38 C39 1.554(7) . ?
C39 C40 1.532(7) . ?
C39 C42 1.536(7) . ?
C39 C41 1.537(7) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 C44 1.381(7) . ?
C43 H43 0.9500 . ?
C44 C49 1.385(7) . ?
C44 C45 1.543(7) . ?
C45 C47 1.529(8) . ?
C45 C48 1.533(7) . ?
C45 C46 1.547(7) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 C50 1.397(7) . ?
C49 H49 0.9500 . ?
C50 C51 1.551(7) . ?
C51 C52 1.531(7) . ?
C51 C53 1.534(7) . ?
C51 C54 1.535(7) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C1S Cl2S 1.706(7) . ?
C1S Cl1S 1.758(7) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
P1C F5C 1.579(4) . ?
P1C F6C 1.583(3) . ?
P1C F1C 1.592(4) . ?
P1C F3C 1.595(3) . ?
P1C F4C 1.596(4) . ?
P1C F2C 1.601(3) . ?
P2C F7C 1.514(5) . ?
P2C F8C 1.533(5) . ?
P2C F11C 1.556(5) . ?
P2C F10C 1.568(5) . ?
P2C F12C 1.577(4) . ?
P2C F9C 1.600(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 C10 101.4(2) . . ?
C28 P2 C37 101.7(2) . . ?
C2 N1 C3 122.0(4) . . ?
C2 N1 H1H 118(4) . . ?
C3 N1 H1H 119(4) . . ?
C2 N2 C6 121.9(4) . . ?
C2 N2 C5 121.6(4) . . ?
C6 N2 C5 116.4(4) . . ?
C29 N3 C30 122.6(4) . . ?
C29 N3 H3H 117(5) . . ?
C30 N3 H3H 120(5) . . ?
C29 N4 C33 121.1(4) . . ?
C29 N4 C32 121.7(4) . . ?
C33 N4 C32 116.8(4) . . ?
C2 C1 C9 115.5(4) . . ?
C2 C1 P1 114.3(4) . . ?
C9 C1 P1 130.1(4) . . ?
N1 C2 N2 122.2(4) . . ?
N1 C2 C1 118.2(4) . . ?
N2 C2 C1 119.6(4) . . ?
N1 C3 C4 107.5(4) . . ?
N1 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
N1 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C5 C4 C3 109.1(4) . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N2 C5 C4 111.7(4) . . ?
N2 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
N2 C6 C7 113.7(4) . . ?
N2 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
N2 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 113.3(4) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 C9 114.6(4) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C1 C9 C8 115.3(4) . . ?
C1 C9 H9A 108.4 . . ?
C8 C9 H9A 108.4 . . ?
C1 C9 H9B 108.4 . . ?
C8 C9 H9B 108.4 . . ?
H9A C9 H9B 107.5 . . ?
C23 C10 C11 120.2(4) . . ?
C23 C10 P1 121.1(3) . . ?
C11 C10 P1 118.2(3) . . ?
C16 C11 C10 117.3(4) . . ?
C16 C11 C12 119.0(4) . . ?
C10 C11 C12 123.5(4) . . ?
C14 C12 C13 110.1(5) . . ?
C14 C12 C11 113.4(4) . . ?
C13 C12 C11 110.8(4) . . ?
C14 C12 C15 105.9(5) . . ?
C13 C12 C15 105.5(5) . . ?
C11 C12 C15 110.7(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 C17 123.2(5) . . ?
C11 C16 H16 118.4 . . ?
C17 C16 H16 118.4 . . ?
C22 C17 C16 116.7(4) . . ?
C22 C17 C18 123.1(4) . . ?
C16 C17 C18 120.0(4) . . ?
C20 C18 C19 109.9(5) . . ?
C20 C18 C17 110.2(4) . . ?
C19 C18 C17 108.9(4) . . ?
C20 C18 C21 108.0(4) . . ?
C19 C18 C21 107.6(5) . . ?
C17 C18 C21 112.2(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 C23 123.3(4) . . ?
C17 C22 H22 118.3 . . ?
C23 C22 H22 118.3 . . ?
C22 C23 C10 117.6(4) . . ?
C22 C23 C24 118.0(4) . . ?
C10 C23 C24 124.4(4) . . ?
C27 C24 C26 110.2(4) . . ?
C27 C24 C25 108.1(5) . . ?
C26 C24 C25 104.9(4) . . ?
C27 C24 C23 112.0(4) . . ?
C26 C24 C23 111.1(4) . . ?
C25 C24 C23 110.2(4) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C36 115.8(4) . . ?
C29 C28 P2 114.4(4) . . ?
C36 C28 P2 129.8(4) . . ?
N3 C29 N4 122.1(4) . . ?
N3 C29 C28 118.4(4) . . ?
N4 C29 C28 119.5(4) . . ?
N3 C30 C31 107.5(4) . . ?
N3 C30 H30A 110.2 . . ?
C31 C30 H30A 110.2 . . ?
N3 C30 H30B 110.2 . . ?
C31 C30 H30B 110.2 . . ?
H30A C30 H30B 108.5 . . ?
C32 C31 C30 110.2(5) . . ?
C32 C31 H31A 109.6 . . ?
C30 C31 H31A 109.6 . . ?
C32 C31 H31B 109.6 . . ?
C30 C31 H31B 109.6 . . ?
H31A C31 H31B 108.1 . . ?
N4 C32 C31 111.9(4) . . ?
N4 C32 H32A 109.2 . . ?
C31 C32 H32A 109.2 . . ?
N4 C32 H32B 109.2 . . ?
C31 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
N4 C33 C34 114.5(4) . . ?
N4 C33 H33A 108.6 . . ?
C34 C33 H33A 108.6 . . ?
N4 C33 H33B 108.6 . . ?
C34 C33 H33B 108.6 . . ?
H33A C33 H33B 107.6 . . ?
C33 C34 C35 113.1(4) . . ?
C33 C34 H34A 109.0 . . ?
C35 C34 H34A 109.0 . . ?
C33 C34 H34B 109.0 . . ?
C35 C34 H34B 109.0 . . ?
H34A C34 H34B 107.8 . . ?
C34 C35 C36 113.9(4) . . ?
C34 C35 H35A 108.8 . . ?
C36 C35 H35A 108.8 . . ?
C34 C35 H35B 108.8 . . ?
C36 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
C28 C36 C35 115.3(4) . . ?
C28 C36 H36A 108.5 . . ?
C35 C36 H36A 108.5 . . ?
C28 C36 H36B 108.5 . . ?
C35 C36 H36B 108.5 . . ?
H36A C36 H36B 107.5 . . ?
C38 C37 C50 120.6(4) . . ?
C38 C37 P2 118.3(4) . . ?
C50 C37 P2 120.9(4) . . ?
C43 C38 C37 117.2(4) . . ?
C43 C38 C39 118.4(4) . . ?
C37 C38 C39 124.3(4) . . ?
C40 C39 C42 106.7(5) . . ?
C40 C39 C41 109.7(5) . . ?
C42 C39 C41 104.7(4) . . ?
C40 C39 C38 109.3(4) . . ?
C42 C39 C38 111.9(4) . . ?
C41 C39 C38 114.3(4) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 C38 122.5(5) . . ?
C44 C43 H43 118.7 . . ?
C38 C43 H43 118.7 . . ?
C43 C44 C49 118.3(4) . . ?
C43 C44 C45 121.5(4) . . ?
C49 C44 C45 120.1(5) . . ?
C47 C45 C48 109.5(5) . . ?
C47 C45 C44 112.6(4) . . ?
C48 C45 C44 111.4(4) . . ?
C47 C45 C46 108.1(5) . . ?
C48 C45 C46 109.7(5) . . ?
C44 C45 C46 105.4(4) . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C44 C49 C50 122.4(5) . . ?
C44 C49 H49 118.8 . . ?
C50 C49 H49 118.8 . . ?
C49 C50 C37 117.3(4) . . ?
C49 C50 C51 118.0(4) . . ?
C37 C50 C51 124.6(4) . . ?
C52 C51 C53 109.8(4) . . ?
C52 C51 C54 107.3(4) . . ?
C53 C51 C54 104.8(4) . . ?
C52 C51 C50 113.2(4) . . ?
C53 C51 C50 110.7(4) . . ?
C54 C51 C50 110.7(4) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C51 C53 H53A 109.5 . . ?
C51 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C51 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C51 C54 H54A 109.5 . . ?
C51 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C51 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
Cl2S C1S Cl1S 114.0(4) . . ?
Cl2S C1S H1S1 108.7 . . ?
Cl1S C1S H1S1 108.7 . . ?
Cl2S C1S H1S2 108.7 . . ?
Cl1S C1S H1S2 108.7 . . ?
H1S1 C1S H1S2 107.6 . . ?
F5C P1C F6C 90.63(19) . . ?
F5C P1C F1C 91.2(2) . . ?
F6C P1C F1C 91.0(2) . . ?
F5C P1C F3C 90.2(2) . . ?
F6C P1C F3C 179.1(2) . . ?
F1C P1C F3C 88.9(2) . . ?
F5C P1C F4C 90.2(2) . . ?
F6C P1C F4C 89.6(2) . . ?
F1C P1C F4C 178.4(2) . . ?
F3C P1C F4C 90.5(2) . . ?
F5C P1C F2C 179.6(2) . . ?
F6C P1C F2C 89.81(19) . . ?
F1C P1C F2C 88.8(2) . . ?
F3C P1C F2C 89.32(19) . . ?
F4C P1C F2C 89.8(2) . . ?
F7C P2C F8C 93.9(5) . . ?
F7C P2C F11C 88.5(5) . . ?
F8C P2C F11C 177.5(4) . . ?
F7C P2C F10C 176.5(5) . . ?
F8C P2C F10C 88.3(4) . . ?
F11C P2C F10C 89.3(4) . . ?
F7C P2C F12C 90.8(3) . . ?
F8C P2C F12C 91.5(2) . . ?
F11C P2C F12C 89.1(3) . . ?
F10C P2C F12C 91.8(3) . . ?
F7C P2C F9C 90.2(3) . . ?
F8C P2C F9C 87.9(2) . . ?
F11C P2C F9C 91.4(3) . . ?
F10C P2C F9C 87.2(3) . . ?
F12C P2C F9C 178.9(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C36 H36A F8C 0.99 2.59 3.467(7) 147.4 2_645
C34 H34B F8C 0.99 2.52 3.397(7) 147.6 2_645
C32 H32B F11C 0.99 2.55 3.490(8) 158.6 2_655
C31 H31A F10C 0.99 2.52 3.437(9) 153.8 2_645
C9 H9B F2C 0.99 2.56 3.438(6) 147.9 2
C7 H7A F4C 0.99 2.53 3.463(7) 158.0 2
C5 H5A F5C 0.99 2.44 3.248(6) 138.5 2_545
C3 H3A F3C 0.99 2.59 3.443(7) 144.3 .

_refine_diff_density_max         0.927
_refine_diff_density_min         -0.920
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_1_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1828167'
_audit_update_record             
;
2018-03-07 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H43 Cl2 N2 P Pd'
_chemical_formula_weight         603.90

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   17.6070(7)
_cell_length_b                   10.5766(4)
_cell_length_c                   15.3298(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.971(3)
_cell_angle_gamma                90
_cell_volume                     2833.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2360
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      18.37

_exptl_crystal_description       Plate
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.918
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6500
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36641
_diffrn_reflns_av_unetI/netI     0.0916
_diffrn_reflns_av_R_equivalents  0.1382
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.251
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4988
_reflns_number_gt                2919
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+3.6257P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4988
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1353
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
Pd1 Pd 0.39249(3) 0.62301(5) 0.37308(3) 0.04121(18) Uani 1 1 d . . . . .
P1 P 0.30745(9) 0.47832(17) 0.33524(12) 0.0423(4) Uani 1 1 d . . . . .
Cl1 Cl 0.49039(10) 0.77206(18) 0.39954(14) 0.0668(6) Uani 1 1 d . . . . .
Cl2 Cl 0.30217(11) 0.77190(18) 0.39624(14) 0.0677(6) Uani 1 1 d . . . . .
N1 N 0.4633(3) 0.4702(5) 0.3608(3) 0.0444(14) Uani 1 1 d . . . . .
N2 N 0.4789(3) 0.2509(5) 0.3569(3) 0.0448(14) Uani 1 1 d . . . . .
C9 C 0.4352(3) 0.3547(6) 0.3498(4) 0.0406(16) Uani 1 1 d . . . . .
C10 C 0.2063(3) 0.4704(6) 0.3006(4) 0.0380(15) Uani 1 1 d . . . . .
C15 C 0.1562(4) 0.4388(6) 0.3632(4) 0.0425(16) Uani 1 1 d . . . . .
C1 C 0.3517(4) 0.3430(6) 0.3242(4) 0.0431(17) Uani 1 1 d . . . . .
C23 C 0.1733(4) 0.4342(7) 0.4641(4) 0.0517(18) Uani 1 1 d . . . . .
C13 C 0.0527(4) 0.4243(7) 0.2428(5) 0.0516(19) Uani 1 1 d . . . . .
C12 C 0.1033(4) 0.4606(6) 0.1855(5) 0.0502(18) Uani 1 1 d . . . . .
H12 H 0.0847 0.4676 0.1262 0.060 Uiso 1 1 calc R U . . .
C11 C 0.1790(3) 0.4872(6) 0.2102(4) 0.0412(16) Uani 1 1 d . . . . .
C17 C 0.2527(4) 0.6747(7) 0.1670(5) 0.061(2) Uani 1 1 d . . . . .
H17A H 0.2093 0.7273 0.1734 0.092 Uiso 1 1 calc R U . . .
H17B H 0.2807 0.7096 0.1227 0.092 Uiso 1 1 calc R U . . .
H17C H 0.2853 0.6707 0.2218 0.092 Uiso 1 1 calc R U . . .
C5 C 0.4546(4) 0.1194(6) 0.3702(5) 0.0565(19) Uani 1 1 d . . . . .
H5A H 0.4953 0.0767 0.4072 0.068 Uiso 1 1 calc R U . . .
H5B H 0.4486 0.0770 0.3137 0.068 Uiso 1 1 calc R U . . .
C8 C 0.5452(3) 0.4840(7) 0.3845(5) 0.0507(18) Uani 1 1 d . . . . .
H8A H 0.5579 0.4714 0.4473 0.061 Uiso 1 1 calc R U . . .
H8B H 0.5609 0.5686 0.3702 0.061 Uiso 1 1 calc R U . . .
C16 C 0.2253(4) 0.5415(7) 0.1398(4) 0.0492(18) Uani 1 1 d . . . . .
C7 C 0.5867(4) 0.3879(7) 0.3350(5) 0.0567(19) Uani 1 1 d . . . . .
H7A H 0.5744 0.4006 0.2722 0.068 Uiso 1 1 calc R U . . .
H7B H 0.6415 0.3973 0.3499 0.068 Uiso 1 1 calc R U . . .
C20 C -0.0323(4) 0.3994(9) 0.2089(5) 0.071(3) Uani 1 1 d . . . . .
C14 C 0.0801(4) 0.4167(7) 0.3299(5) 0.0529(19) Uani 1 1 d . . . . .
H14 H 0.0460 0.3955 0.3693 0.063 Uiso 1 1 calc R U . . .
C6 C 0.5621(4) 0.2581(7) 0.3600(5) 0.057(2) Uani 1 1 d . . . . .
H6A H 0.5793 0.1963 0.3200 0.068 Uiso 1 1 calc R U . . .
H6B H 0.5856 0.2380 0.4188 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3824(4) 0.1038(7) 0.4107(5) 0.066(2) Uani 1 1 d . . . . .
H4A H 0.3814 0.1660 0.4570 0.079 Uiso 1 1 calc R U . . .
H4B H 0.3823 0.0207 0.4375 0.079 Uiso 1 1 calc R U . . .
C3 C 0.3106(4) 0.1178(7) 0.3465(6) 0.070(2) Uani 1 1 d . . . . .
H3A H 0.3011 0.0396 0.3141 0.084 Uiso 1 1 calc R U . . .
H3B H 0.2674 0.1330 0.3789 0.084 Uiso 1 1 calc R U . . .
C2 C 0.3164(4) 0.2242(6) 0.2830(5) 0.0559(19) Uani 1 1 d . . . . .
H2A H 0.2655 0.2440 0.2546 0.067 Uiso 1 1 calc R U . . .
H2B H 0.3466 0.1962 0.2378 0.067 Uiso 1 1 calc R U . . .
C18 C 0.1753(4) 0.5570(9) 0.0507(5) 0.080(3) Uani 1 1 d . . . . .
H18A H 0.1555 0.4761 0.0308 0.120 Uiso 1 1 calc R U . . .
H18B H 0.2057 0.5913 0.0084 0.120 Uiso 1 1 calc R U . . .
H18C H 0.1337 0.6133 0.0574 0.120 Uiso 1 1 calc R U . . .
C19 C 0.2934(4) 0.4604(8) 0.1216(5) 0.079(3) Uani 1 1 d . . . . .
H19A H 0.3299 0.4569 0.1734 0.119 Uiso 1 1 calc R U . . .
H19B H 0.3169 0.4969 0.0743 0.119 Uiso 1 1 calc R U . . .
H19C H 0.2761 0.3765 0.1058 0.119 Uiso 1 1 calc R U . . .
C25 C 0.2537(5) 0.4319(14) 0.5048(6) 0.139(5) Uani 1 1 d . . . . .
H25A H 0.2780 0.3565 0.4871 0.209 Uiso 1 1 calc R U . . .
H25B H 0.2552 0.4330 0.5676 0.209 Uiso 1 1 calc R U . . .
H25C H 0.2800 0.5046 0.4861 0.209 Uiso 1 1 calc R U . . .
C21 C -0.0370(5) 0.3060(12) 0.1329(8) 0.147(5) Uani 1 1 d . . . . .
H21A H -0.0011 0.2386 0.1474 0.221 Uiso 1 1 calc R U . . .
H21B H -0.0249 0.3485 0.0810 0.221 Uiso 1 1 calc R U . . .
H21C H -0.0878 0.2719 0.1225 0.221 Uiso 1 1 calc R U . . .
C24 C 0.1358(7) 0.3210(11) 0.4992(6) 0.155(6) Uani 1 1 d . . . . .
H24A H 0.1564 0.2454 0.4766 0.232 Uiso 1 1 calc R U . . .
H24B H 0.0816 0.3244 0.4813 0.232 Uiso 1 1 calc R U . . .
H24C H 0.1453 0.3207 0.5622 0.232 Uiso 1 1 calc R U . . .
C22 C -0.0685(5) 0.5181(12) 0.1698(10) 0.162(6) Uani 1 1 d . . . . .
H22A H -0.1164 0.4979 0.1357 0.243 Uiso 1 1 calc R U . . .
H22B H -0.0351 0.5569 0.1327 0.243 Uiso 1 1 calc R U . . .
H22C H -0.0773 0.5755 0.2161 0.243 Uiso 1 1 calc R U . . .
C00W C 0.1383(8) 0.5492(13) 0.4985(7) 0.185(7) Uani 1 1 d . . . . .
H00A H 0.1447 0.5470 0.5616 0.277 Uiso 1 1 calc R U . . .
H00B H 0.0847 0.5515 0.4773 0.277 Uiso 1 1 calc R U . . .
H00C H 0.1628 0.6232 0.4788 0.277 Uiso 1 1 calc R U . . .
C26 C -0.0757(6) 0.3499(19) 0.2761(8) 0.243(11) Uani 1 1 d . . . . .
H26A H -0.0839 0.4159 0.3170 0.365 Uiso 1 1 calc R U . . .
H26B H -0.0478 0.2821 0.3067 0.365 Uiso 1 1 calc R U . . .
H26C H -0.1242 0.3191 0.2491 0.365 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
Pd1 N1 2.064(5) . ?
Pd1 P1 2.1700(18) . ?
Pd1 Cl2 2.2960(18) . ?
Pd1 Cl1 2.3348(18) . ?
P1 C1 1.648(6) . ?
P1 C10 1.797(6) . ?
N1 C9 1.320(8) . ?
N1 C8 1.450(7) . ?
N2 C9 1.338(8) . ?
N2 C6 1.461(8) . ?
N2 C5 1.476(8) . ?
C9 C1 1.481(8) . ?
C10 C15 1.420(8) . ?
C10 C11 1.422(8) . ?
C15 C14 1.395(8) . ?
C15 C23 1.540(9) . ?
C1 C2 1.505(8) . ?
C23 C25 1.475(10) . ?
C23 C00W 1.489(12) . ?
C23 C24 1.500(11) . ?
C13 C14 1.366(9) . ?
C13 C12 1.379(9) . ?
C13 C20 1.547(9) . ?
C12 C11 1.371(8) . ?
C12 H12 0.9300 . ?
C11 C16 1.541(9) . ?
C17 C16 1.530(9) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C5 C4 1.490(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C8 C7 1.510(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C16 C19 1.526(9) . ?
C16 C18 1.541(9) . ?
C7 C6 1.504(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C20 C26 1.453(12) . ?
C20 C22 1.499(13) . ?
C20 C21 1.522(13) . ?
C14 H14 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 C3 1.511(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 C2 1.500(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C00W H00A 0.9600 . ?
C00W H00B 0.9600 . ?
C00W H00C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
N1 Pd1 P1 80.11(15) . . ?
N1 Pd1 Cl2 171.36(16) . . ?
P1 Pd1 Cl2 93.25(7) . . ?
N1 Pd1 Cl1 95.92(15) . . ?
P1 Pd1 Cl1 173.44(7) . . ?
Cl2 Pd1 Cl1 91.18(7) . . ?
C1 P1 C10 113.1(3) . . ?
C1 P1 Pd1 108.7(2) . . ?
C10 P1 Pd1 137.6(2) . . ?
C9 N1 C8 118.1(5) . . ?
C9 N1 Pd1 121.0(4) . . ?
C8 N1 Pd1 119.4(4) . . ?
C9 N2 C6 121.6(6) . . ?
C9 N2 C5 127.7(5) . . ?
C6 N2 C5 110.5(5) . . ?
N1 C9 N2 123.1(6) . . ?
N1 C9 C1 117.1(6) . . ?
N2 C9 C1 119.7(6) . . ?
C15 C10 C11 121.6(5) . . ?
C15 C10 P1 119.1(5) . . ?
C11 C10 P1 119.2(5) . . ?
C14 C15 C10 116.2(6) . . ?
C14 C15 C23 115.1(6) . . ?
C10 C15 C23 128.6(6) . . ?
C9 C1 C2 121.8(5) . . ?
C9 C1 P1 111.5(4) . . ?
C2 C1 P1 126.3(5) . . ?
C25 C23 C00W 106.3(9) . . ?
C25 C23 C24 106.1(8) . . ?
C00W C23 C24 107.8(9) . . ?
C25 C23 C15 119.1(6) . . ?
C00W C23 C15 106.9(7) . . ?
C24 C23 C15 110.2(6) . . ?
C14 C13 C12 117.5(6) . . ?
C14 C13 C20 122.1(6) . . ?
C12 C13 C20 120.4(7) . . ?
C11 C12 C13 124.2(6) . . ?
C11 C12 H12 117.9 . . ?
C13 C12 H12 117.9 . . ?
C12 C11 C10 116.5(6) . . ?
C12 C11 C16 117.6(6) . . ?
C10 C11 C16 125.7(5) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C5 C4 116.0(6) . . ?
N2 C5 H5A 108.3 . . ?
C4 C5 H5A 108.3 . . ?
N2 C5 H5B 108.3 . . ?
C4 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
N1 C8 C7 109.5(5) . . ?
N1 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C19 C16 C17 109.8(6) . . ?
C19 C16 C18 106.0(6) . . ?
C17 C16 C18 105.7(6) . . ?
C19 C16 C11 114.3(6) . . ?
C17 C16 C11 109.2(6) . . ?
C18 C16 C11 111.5(5) . . ?
C6 C7 C8 108.3(6) . . ?
C6 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C26 C20 C22 110.5(10) . . ?
C26 C20 C21 108.9(10) . . ?
C22 C20 C21 104.9(9) . . ?
C26 C20 C13 113.2(7) . . ?
C22 C20 C13 109.8(7) . . ?
C21 C20 C13 109.1(7) . . ?
C13 C14 C15 123.9(6) . . ?
C13 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?
N2 C6 C7 111.0(5) . . ?
N2 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C5 C4 C3 114.0(7) . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C2 C3 C4 112.3(6) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C3 C2 C1 114.2(6) . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C00W H00A 109.5 . . ?
C23 C00W H00B 109.5 . . ?
H00A C00W H00B 109.5 . . ?
C23 C00W H00C 109.5 . . ?
H00A C00W H00C 109.5 . . ?
H00B C00W H00C 109.5 . . ?
C20 C26 H26A 109.5 . . ?
C20 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C20 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_refine_diff_density_max         0.749
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_AG_AG_116_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1828168'
_audit_update_record             
;
2018-03-07 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H46 Cl N2 O P'
_chemical_formula_weight         481.08

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

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

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

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

_cell_length_a                   37.4034(9)
_cell_length_b                   8.1220(2)
_cell_length_c                   19.1281(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.542(2)
_cell_angle_gamma                90
_cell_volume                     5540.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4085
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      20.89

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_F_000             2096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.216
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7088
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38412
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.180
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5165
_reflns_number_gt                3753
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0855P)²+8.3832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5165
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1681
_refine_ls_wR_factor_gt          0.1499
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C1 C 0.33123(8) 0.6189(4) 0.24463(15) 0.0285(6) Uani 1 1 d . . . . .
C2 C 0.35028(9) 0.7725(4) 0.22815(16) 0.0350(7) Uani 1 1 d . . . . .
H2A H 0.3335 0.8673 0.2273 0.042 Uiso 1 1 calc R U . . .
H2B H 0.3734 0.7904 0.2694 0.042 Uiso 1 1 calc R U . . .
C3 C 0.36069(11) 0.7752(5) 0.1585(2) 0.0508(9) Uani 1 1 d . . . . .
H3A H 0.3786 0.6846 0.1601 0.061 Uiso 1 1 calc R U . . .
H3B H 0.3738 0.8800 0.1562 0.061 Uiso 1 1 calc R U . . .
C4 C 0.32802(9) 0.7581(4) 0.08835(17) 0.0402(8) Uani 1 1 d . . . . .
H4A H 0.3106 0.8517 0.0842 0.048 Uiso 1 1 calc R U . . .
H4B H 0.3376 0.7608 0.0454 0.048 Uiso 1 1 calc R U . . .
C5 C 0.30735(9) 0.5981(4) 0.08863(17) 0.0368(7) Uani 1 1 d . . . . .
H5A H 0.2939 0.5673 0.0374 0.044 Uiso 1 1 calc R U . . .
H5B H 0.3259 0.5105 0.1095 0.044 Uiso 1 1 calc R U . . .
C6 C 0.29117(8) 0.6003(3) 0.20263(16) 0.0277(6) Uani 1 1 d . . . . .
C7 C 0.22654(9) 0.5597(5) 0.20260(19) 0.0448(9) Uani 1 1 d . . . . .
H7A H 0.2119 0.5960 0.2351 0.054 Uiso 1 1 calc R U . . .
H7B H 0.2209 0.4422 0.1904 0.054 Uiso 1 1 calc R U . . .
C8 C 0.21611(8) 0.6612(4) 0.13361(19) 0.0417(8) Uani 1 1 d . . . . .
H8A H 0.2197 0.7796 0.1462 0.050 Uiso 1 1 calc R U . . .
H8B H 0.1894 0.6434 0.1061 0.050 Uiso 1 1 calc R U . . .
C9 C 0.24040(9) 0.6118(5) 0.08705(18) 0.0454(9) Uani 1 1 d . . . . .
H9A H 0.2324 0.5023 0.0652 0.054 Uiso 1 1 calc R U . . .
H9B H 0.2370 0.6919 0.0465 0.054 Uiso 1 1 calc R U . . .
C10 C 0.39844(7) 0.5284(3) 0.34510(15) 0.0242(6) Uani 1 1 d . . . . .
C11 C 0.42509(8) 0.4523(3) 0.31640(15) 0.0246(6) Uani 1 1 d . . . . .
C12 C 0.46124(7) 0.5187(3) 0.33539(15) 0.0251(6) Uani 1 1 d . . . . .
H12 H 0.4790 0.4707 0.3149 0.030 Uiso 1 1 calc R U . . .
C13 C 0.47237(7) 0.6508(3) 0.38251(15) 0.0245(6) Uani 1 1 d . . . . .
C14 C 0.44671(7) 0.7114(3) 0.41600(15) 0.0259(6) Uani 1 1 d . . . . .
H14 H 0.4545 0.7971 0.4511 0.031 Uiso 1 1 calc R U . . .
C15 C 0.41019(7) 0.6518(3) 0.40016(15) 0.0247(6) Uani 1 1 d . . . . .
C16 C 0.41777(8) 0.2899(3) 0.27123(16) 0.0280(6) Uani 1 1 d . . . . .
C17 C 0.45302(9) 0.2282(4) 0.25475(18) 0.0360(7) Uani 1 1 d . . . . .
H17A H 0.4732 0.2136 0.3008 0.054 Uiso 1 1 calc R U . . .
H17B H 0.4607 0.3088 0.2240 0.054 Uiso 1 1 calc R U . . .
H17C H 0.4477 0.1226 0.2289 0.054 Uiso 1 1 calc R U . . .
C18 C 0.38791(9) 0.3047(4) 0.19618(16) 0.0371(7) Uani 1 1 d . . . . .
H18A H 0.3871 0.2024 0.1685 0.056 Uiso 1 1 calc R U . . .
H18B H 0.3942 0.3968 0.1690 0.056 Uiso 1 1 calc R U . . .
H18C H 0.3634 0.3242 0.2031 0.056 Uiso 1 1 calc R U . . .
C19 C 0.40631(9) 0.1562(4) 0.31676(18) 0.0363(7) Uani 1 1 d . . . . .
H19A H 0.4035 0.0510 0.2906 0.054 Uiso 1 1 calc R U . . .
H19B H 0.3824 0.1864 0.3245 0.054 Uiso 1 1 calc R U . . .
H19C H 0.4257 0.1458 0.3643 0.054 Uiso 1 1 calc R U . . .
C20 C 0.38611(8) 0.7119(3) 0.44838(15) 0.0276(6) Uani 1 1 d . . . . .
C21 C 0.40992(9) 0.8069(4) 0.51603(17) 0.0394(8) Uani 1 1 d . . . . .
H21A H 0.4193 0.9084 0.5002 0.059 Uiso 1 1 calc R U . . .
H21B H 0.4311 0.7384 0.5433 0.059 Uiso 1 1 calc R U . . .
H21C H 0.3945 0.8343 0.5476 0.059 Uiso 1 1 calc R U . . .
C22 C 0.36932(9) 0.5646(4) 0.47737(17) 0.0343(7) Uani 1 1 d . . . . .
H22A H 0.3572 0.6028 0.5132 0.052 Uiso 1 1 calc R U . . .
H22B H 0.3893 0.4866 0.5010 0.052 Uiso 1 1 calc R U . . .
H22C H 0.3508 0.5102 0.4365 0.052 Uiso 1 1 calc R U . . .
C23 C 0.35479(8) 0.8317(4) 0.40831(17) 0.0329(7) Uani 1 1 d . . . . .
H23A H 0.3369 0.7746 0.3674 0.049 Uiso 1 1 calc R U . . .
H23B H 0.3657 0.9251 0.3895 0.049 Uiso 1 1 calc R U . . .
H23C H 0.3418 0.8716 0.4425 0.049 Uiso 1 1 calc R U . . .
C24 C 0.51153(7) 0.7269(3) 0.40124(16) 0.0271(6) Uani 1 1 d . . . . .
C25 C 0.53710(8) 0.6371(4) 0.36512(19) 0.0400(8) Uani 1 1 d . . . . .
H25A H 0.5402 0.5225 0.3819 0.060 Uiso 1 1 calc R U . . .
H25B H 0.5617 0.6912 0.3785 0.060 Uiso 1 1 calc R U . . .
H25C H 0.5259 0.6398 0.3117 0.060 Uiso 1 1 calc R U . . .
C26 C 0.50765(9) 0.9060(4) 0.37404(19) 0.0384(8) Uani 1 1 d . . . . .
H26A H 0.4962 0.9077 0.3207 0.058 Uiso 1 1 calc R U . . .
H26B H 0.5325 0.9573 0.3867 0.058 Uiso 1 1 calc R U . . .
H26C H 0.4917 0.9671 0.3974 0.058 Uiso 1 1 calc R U . . .
C27 C 0.53036(8) 0.7241(4) 0.48459(16) 0.0373(7) Uani 1 1 d . . . . .
H27A H 0.5150 0.7861 0.5089 0.056 Uiso 1 1 calc R U . . .
H27B H 0.5553 0.7745 0.4961 0.056 Uiso 1 1 calc R U . . .
H27C H 0.5328 0.6099 0.5020 0.056 Uiso 1 1 calc R U . . .
Cl1 Cl 0.26161(2) 0.60501(10) 0.39794(4) 0.0369(2) Uani 1 1 d . . . . .
N1 N 0.26667(7) 0.5807(3) 0.23962(15) 0.0345(6) Uani 1 1 d . . . . .
N2 N 0.28042(7) 0.6055(3) 0.13042(13) 0.0307(6) Uani 1 1 d . . . . .
O1 O 0.19113(8) 0.6918(3) 0.45344(16) 0.0560(7) Uani 1 1 d D . . . .
P1 P 0.34860(2) 0.47124(9) 0.30710(4) 0.0277(2) Uani 1 1 d . . . . .
H1N H 0.2740(11) 0.585(5) 0.298(2) 0.061(11) Uiso 1 1 d . . . . .
H1S H 0.2060(12) 0.750(5) 0.493(2) 0.087(16) Uiso 1 1 d D . . . .
H2S H 0.2078(11) 0.671(5) 0.427(2) 0.065(13) Uiso 1 1 d 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
C1 C6 1.479(4) . ?
C1 C2 1.516(4) . ?
C1 P1 1.680(3) . ?
C2 C3 1.497(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.525(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.512(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N2 1.464(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N2 1.318(4) . ?
C6 N1 1.326(4) . ?
C7 N1 1.464(4) . ?
C7 C8 1.505(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.506(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.477(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.416(4) . ?
C10 C15 1.424(4) . ?
C10 P1 1.844(3) . ?
C11 C12 1.398(4) . ?
C11 C16 1.556(4) . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(4) . ?
C13 C24 1.529(4) . ?
C14 C15 1.394(4) . ?
C14 H14 0.9500 . ?
C15 C20 1.549(4) . ?
C16 C17 1.530(4) . ?
C16 C19 1.531(4) . ?
C16 C18 1.535(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C22 1.531(4) . ?
C20 C23 1.538(4) . ?
C20 C21 1.539(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.524(4) . ?
C24 C26 1.537(4) . ?
C24 C27 1.537(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N1 H1N 1.07(4) . ?
O1 H1S 0.93(3) . ?
O1 H2S 0.92(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 115.7(2) . . ?
C6 C1 P1 115.1(2) . . ?
C2 C1 P1 129.1(2) . . ?
C3 C2 C1 117.5(3) . . ?
C3 C2 H2A 107.9 . . ?
C1 C2 H2A 107.9 . . ?
C3 C2 H2B 107.9 . . ?
C1 C2 H2B 107.9 . . ?
H2A C2 H2B 107.2 . . ?
C2 C3 C4 115.3(3) . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C3 110.5(3) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N2 C5 C4 113.8(3) . . ?
N2 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
N2 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N2 C6 N1 121.4(3) . . ?
N2 C6 C1 120.4(3) . . ?
N1 C6 C1 118.2(3) . . ?
N1 C7 C8 108.5(3) . . ?
N1 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
N1 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C7 C8 C9 109.2(3) . . ?
C7 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
N2 C9 C8 111.5(3) . . ?
N2 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C15 119.8(2) . . ?
C11 C10 P1 118.9(2) . . ?
C15 C10 P1 121.2(2) . . ?
C12 C11 C10 118.0(2) . . ?
C12 C11 C16 117.8(2) . . ?
C10 C11 C16 123.9(2) . . ?
C13 C12 C11 123.1(3) . . ?
C13 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C12 C13 C14 117.4(2) . . ?
C12 C13 C24 123.1(2) . . ?
C14 C13 C24 119.5(2) . . ?
C15 C14 C13 122.9(3) . . ?
C15 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
C14 C15 C10 118.0(2) . . ?
C14 C15 C20 118.0(2) . . ?
C10 C15 C20 123.8(2) . . ?
C17 C16 C19 106.9(2) . . ?
C17 C16 C18 105.2(2) . . ?
C19 C16 C18 109.8(2) . . ?
C17 C16 C11 112.0(2) . . ?
C19 C16 C11 108.5(2) . . ?
C18 C16 C11 114.2(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C20 C23 109.9(2) . . ?
C22 C20 C21 106.5(2) . . ?
C23 C20 C21 105.2(2) . . ?
C22 C20 C15 110.2(2) . . ?
C23 C20 C15 113.2(2) . . ?
C21 C20 C15 111.4(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C13 112.8(2) . . ?
C25 C24 C26 107.9(3) . . ?
C13 C24 C26 108.5(2) . . ?
C25 C24 C27 108.0(2) . . ?
C13 C24 C27 110.1(2) . . ?
C26 C24 C27 109.4(2) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C6 N1 C7 121.9(3) . . ?
C6 N1 H1N 124(2) . . ?
C7 N1 H1N 114(2) . . ?
C6 N2 C5 121.9(2) . . ?
C6 N2 C9 121.8(3) . . ?
C5 N2 C9 116.3(2) . . ?
H1S O1 H2S 102(4) . . ?
C1 P1 C10 103.24(13) . . ?

_refine_diff_density_max         1.139
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.073

