# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_111103A
_database_code_depnum_ccdc_archive 'CCDC 1969435'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2020-05-17 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N2 O6 P'
_chemical_formula_weight         464.40

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'
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'
N N 0.0061 0.0033 '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                   17.6881(6)
_cell_length_b                   7.5408(2)
_cell_length_c                   17.2621(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.021(4)
_cell_angle_gamma                90
_cell_volume                     2213.03(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4796
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      32.556
_diffrn_orient_matrix_ub_11      0.0217612608
_diffrn_orient_matrix_ub_12      0.0323515892
_diffrn_orient_matrix_ub_13      -0.0259391218
_diffrn_orient_matrix_ub_21      0.0353951302
_diffrn_orient_matrix_ub_22      -0.0105113770
_diffrn_orient_matrix_ub_23      0.0312664004
_diffrn_orient_matrix_ub_31      0.0038093643
_diffrn_orient_matrix_ub_32      -0.0877073348
_diffrn_orient_matrix_ub_33      -0.0133307626

_exptl_crystal_description       'flat rod'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -1 0.1742
0 1 1 0.239
-7 0 5 0.0467
7 0 -5 0.0097
2 0 -6 0.0323
-2 0 6 0.0661
5 0 1 0.0462
-5 0 -1 0.0754
_exptl_absorpt_coefficient_mu    0.169
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   
;
  CrysAlisPro, Oxford Diffraction Ltd.,
      Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
      (compiled Nov  6 2009,16:24:50)
Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S.
       (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            11997
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.877
_diffrn_reflns_theta_max         32.587
_diffrn_reflns_theta_full        31.000
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3760
_reflns_number_gt                2592
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0400P)²+0.9500P] 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         3760
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.500000 0.44867(6) 0.250000 0.01382(10) Uani 1 2 d S T P . .
C11 C 0.43612(7) 0.30403(15) 0.28504(7) 0.0145(2) Uani 1 1 d . . . . .
C12 C 0.47036(7) 0.17243(16) 0.34108(7) 0.0172(2) Uani 1 1 d . . . . .
H12 H 0.525936 0.164957 0.361483 0.021 Uiso 1 1 calc R U . . .
C13 C 0.42247(7) 0.05308(17) 0.36656(7) 0.0196(2) Uani 1 1 d . . . . .
H13 H 0.445164 -0.035542 0.405073 0.024 Uiso 1 1 calc R U . . .
C14 C 0.34112(7) 0.06347(17) 0.33557(7) 0.0210(3) Uani 1 1 d . . . . .
H14 H 0.308415 -0.017600 0.353464 0.025 Uiso 1 1 calc R U . . .
C15 C 0.30757(7) 0.19102(18) 0.27889(8) 0.0227(3) Uani 1 1 d . . . . .
H15 H 0.252052 0.195579 0.257256 0.027 Uiso 1 1 calc R U . . .
C16 C 0.35479(7) 0.31246(17) 0.25352(7) 0.0194(3) Uani 1 1 d . . . . .
H16 H 0.331727 0.400655 0.214929 0.023 Uiso 1 1 calc R U . . .
C31 C 0.55544(7) 0.59037(15) 0.32816(7) 0.0152(2) Uani 1 1 d . . . . .
C32 C 0.60096(7) 0.72349(17) 0.30643(8) 0.0202(3) Uani 1 1 d . . . . .
H32 H 0.601159 0.736699 0.251755 0.024 Uiso 1 1 calc R U . . .
C33 C 0.64566(8) 0.83578(18) 0.36482(8) 0.0236(3) Uani 1 1 d . . . . .
H33 H 0.676932 0.925518 0.350350 0.028 Uiso 1 1 calc R U . . .
C34 C 0.64468(8) 0.81686(18) 0.44474(8) 0.0237(3) Uani 1 1 d . . . . .
H34 H 0.675595 0.893467 0.484821 0.028 Uiso 1 1 calc R U . . .
C35 C 0.59890(8) 0.68702(18) 0.46613(8) 0.0235(3) Uani 1 1 d . . . . .
H35 H 0.598283 0.675581 0.520763 0.028 Uiso 1 1 calc R U . . .
C36 C 0.55384(7) 0.57332(17) 0.40821(7) 0.0193(2) Uani 1 1 d . . . . .
H36 H 0.522210 0.484735 0.422950 0.023 Uiso 1 1 calc R U . . .
N1 N 0.16551(7) 0.19094(15) 0.05933(7) 0.0240(2) Uani 1 1 d . . . . .
O11 O 0.24030(6) 0.18375(15) 0.06174(6) 0.0318(2) Uani 1 1 d . . . . .
O12 O 0.14590(6) 0.12125(14) 0.11503(6) 0.0332(3) Uani 1 1 d . . . . .
O13 O 0.12003(6) 0.26863(13) 0.00260(6) 0.0290(2) Uani 1 1 d . . . . .
H11 H 0.248(3) 0.230(5) 0.017(2) 0.031(10) Uiso 0.5 1 d . . P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C31 1.7870(12) . ?
P1 C31 1.7871(12) 6_656 ?
P1 C11 1.7914(12) 6_656 ?
P1 C11 1.7915(12) . ?
C11 C16 1.3920(17) . ?
C11 C12 1.4015(16) . ?
C12 C13 1.3880(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3920(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3835(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3892(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C31 C36 1.3958(16) . ?
C31 C32 1.4012(17) . ?
C32 C33 1.3850(17) . ?
C32 H32 0.9500 . ?
C33 C34 1.3919(18) . ?
C33 H33 0.9500 . ?
C34 C35 1.3841(19) . ?
C34 H34 0.9500 . ?
C35 C36 1.3894(17) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
N1 O12 1.2269(14) . ?
N1 O13 1.2307(14) . ?
N1 O11 1.3132(15) . ?
O11 H11 0.88(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
C31 P1 C31 106.56(8) . 6_656 ?
C31 P1 C11 110.68(5) . 6_656 ?
C31 P1 C11 112.02(5) 6_656 6_656 ?
C31 P1 C11 112.02(5) . . ?
C31 P1 C11 110.68(5) 6_656 . ?
C11 P1 C11 104.99(8) 6_656 . ?
C16 C11 C12 120.34(11) . . ?
C16 C11 P1 121.36(9) . . ?
C12 C11 P1 118.13(9) . . ?
C13 C12 C11 119.51(11) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 119.88(12) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.47(11) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.22(11) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 119.55(11) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
C36 C31 C32 120.08(11) . . ?
C36 C31 P1 122.38(9) . . ?
C32 C31 P1 117.54(9) . . ?
C33 C32 C31 119.87(11) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C34 119.86(12) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C35 C34 C33 120.34(12) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C36 120.41(12) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 119.42(12) . . ?
C35 C36 H36 120.3 . . ?
C31 C36 H36 120.3 . . ?
O12 N1 O13 124.30(12) . . ?
O12 N1 O11 117.25(11) . . ?
O13 N1 O11 118.44(11) . . ?
N1 O11 H11 110(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C31 P1 C11 C16 117.47(10) . . . . ?
C31 P1 C11 C16 -1.29(12) 6_656 . . . ?
C11 P1 C11 C16 -122.35(11) 6_656 . . . ?
C31 P1 C11 C12 -67.17(10) . . . . ?
C31 P1 C11 C12 174.06(9) 6_656 . . . ?
C11 P1 C11 C12 53.00(8) 6_656 . . . ?
C16 C11 C12 C13 -1.63(18) . . . . ?
P1 C11 C12 C13 -177.03(9) . . . . ?
C11 C12 C13 C14 0.84(18) . . . . ?
C12 C13 C14 C15 0.61(19) . . . . ?
C13 C14 C15 C16 -1.3(2) . . . . ?
C14 C15 C16 C11 0.51(19) . . . . ?
C12 C11 C16 C15 0.95(18) . . . . ?
P1 C11 C16 C15 176.20(10) . . . . ?
C31 P1 C31 C36 127.52(12) 6_656 . . . ?
C11 P1 C31 C36 -110.45(11) 6_656 . . . ?
C11 P1 C31 C36 6.35(12) . . . . ?
C31 P1 C31 C32 -51.76(8) 6_656 . . . ?
C11 P1 C31 C32 70.27(11) 6_656 . . . ?
C11 P1 C31 C32 -172.93(9) . . . . ?
C36 C31 C32 C33 1.35(19) . . . . ?
P1 C31 C32 C33 -179.35(10) . . . . ?
C31 C32 C33 C34 -0.5(2) . . . . ?
C32 C33 C34 C35 -0.4(2) . . . . ?
C33 C34 C35 C36 0.4(2) . . . . ?
C34 C35 C36 C31 0.4(2) . . . . ?
C32 C31 C36 C35 -1.27(18) . . . . ?
P1 C31 C36 C35 179.47(10) . . . . ?

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
_geom_hbond_publ_flag
O11 H11^a O11 0.88(3) 1.58(3) 2.462(2) 179(5) 7 yes

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.327
_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_110301A
_database_code_depnum_ccdc_archive 'CCDC 1969437'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2020-05-17 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 P, C2 F6 N O4 S2'
_chemical_formula_sum            'C26 H20 F6 N O4 P S2'
_chemical_formula_weight         619.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   22.2823(3)
_cell_length_b                   7.3469(1)
_cell_length_c                   16.0521(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.053(1)
_cell_angle_gamma                90
_cell_volume                     2607.94(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7049
_cell_measurement_theta_min      4.589
_cell_measurement_theta_max      67.137
_diffrn_orient_matrix_UB_11      -0.0146134
_diffrn_orient_matrix_UB_12      0.0700085
_diffrn_orient_matrix_UB_13      -0.0906416
_diffrn_orient_matrix_UB_21      -0.0034456
_diffrn_orient_matrix_UB_22      -0.1975499
_diffrn_orient_matrix_UB_23      -0.0324369
_diffrn_orient_matrix_UB_31      -0.0680487
_diffrn_orient_matrix_UB_32      -0.0050882
_diffrn_orient_matrix_UB_33      0.0089900

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.152
_shelx_estimated_absorpt_T_min   0.616
_shelx_estimated_absorpt_T_max   0.743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            9481
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.998
_diffrn_reflns_theta_max         67.246
_diffrn_reflns_theta_full        67.246
_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             2314
_reflns_number_gt                2150
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0350P)²+3.7500P] 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         2314
_refine_ls_number_parameters     249
_refine_ls_number_restraints     110
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.027
_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 0.000000 0.35661(7) 0.250000 0.01578(14) Uani 1 2 d S T P . .
C11 C 0.04811(6) 0.5028(2) 0.31843(9) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.05328(7) 0.4855(2) 0.40564(9) 0.0218(3) Uani 1 1 d . . . . .
H12 H 0.031851 0.392691 0.430730 0.026 Uiso 1 1 calc R U . . .
C13 C 0.09018(7) 0.6058(2) 0.45528(10) 0.0270(4) Uani 1 1 d . . . . .
H13 H 0.093680 0.595787 0.514685 0.032 Uiso 1 1 calc R U . . .
C14 C 0.12190(7) 0.7403(2) 0.41883(11) 0.0278(4) Uani 1 1 d . . . . .
H14 H 0.147483 0.820797 0.453216 0.033 Uiso 1 1 calc R U . . .
C15 C 0.11633(7) 0.7574(2) 0.33201(11) 0.0271(4) Uani 1 1 d . . . . .
H15 H 0.137971 0.850011 0.307111 0.032 Uiso 1 1 calc R U . . .
C16 C 0.07937(7) 0.6401(2) 0.28191(10) 0.0237(3) Uani 1 1 d . . . . .
H16 H 0.075232 0.652766 0.222584 0.028 Uiso 1 1 calc R U . . .
C21 C 0.04268(7) 0.2099(2) 0.19001(9) 0.0178(3) Uani 1 1 d . . . . .
C22 C 0.10518(7) 0.2247(2) 0.19142(9) 0.0217(3) Uani 1 1 d . . . . .
H22 H 0.127149 0.314983 0.224815 0.026 Uiso 1 1 calc R U . . .
C23 C 0.13488(7) 0.1050(2) 0.14307(10) 0.0268(4) Uani 1 1 d . . . . .
H23 H 0.177423 0.113938 0.143217 0.032 Uiso 1 1 calc R U . . .
C24 C 0.10269(8) -0.0269(2) 0.09479(10) 0.0269(4) Uani 1 1 d . . . . .
H24 H 0.123232 -0.106590 0.061251 0.032 Uiso 1 1 calc R U . . .
C25 C 0.04081(8) -0.0436(2) 0.09501(10) 0.0252(3) Uani 1 1 d . . . . .
H25 H 0.019242 -0.136130 0.062617 0.030 Uiso 1 1 calc R U . . .
C26 C 0.01031(7) 0.0744(2) 0.14237(9) 0.0214(3) Uani 1 1 d . . . . .
H26 H -0.032164 0.063541 0.142519 0.026 Uiso 1 1 calc R U . . .
S1 S 0.2793(2) 0.7513(8) 0.0813(4) 0.0335(11) Uani 0.5 1 d . U P A -1
C1 C 0.2326(6) 0.5717(16) 0.1359(8) 0.0268(8) Uani 0.5 1 d . U P A -1
N1 N 0.23182(11) 0.8414(3) 0.01576(15) 0.0208(5) Uani 0.5 1 d . . P A -1
O1 O 0.33127(11) 0.6752(3) 0.06462(18) 0.0240(5) Uani 0.5 1 d . . P A -1
O2 O 0.28592(11) 0.8949(3) 0.15471(14) 0.0317(5) Uani 0.5 1 d . . P A -1
F1 F 0.26708(10) 0.5156(3) 0.20179(13) 0.0392(5) Uani 0.5 1 d . . P A -1
F2 F 0.22695(12) 0.4396(3) 0.07833(16) 0.0435(5) Uani 0.5 1 d . . P A -1
F3 F 0.18281(12) 0.6341(5) 0.1504(2) 0.0541(8) Uani 0.5 1 d . . P A -1
O1' O 0.16165(11) 0.8097(4) -0.11234(19) 0.0282(6) Uani 0.5 1 d . . P A -1
O2' O 0.24521(11) 0.5868(3) -0.09042(14) 0.0287(5) Uani 0.5 1 d . . P A -1
F1' F 0.32668(10) 0.9038(4) -0.10462(16) 0.0321(5) Uani 0.5 1 d . . P A -1
F2' F 0.26202(12) 0.8710(5) -0.21428(14) 0.0584(7) Uani 0.5 1 d . . P A -1
F3' F 0.25220(11) 1.0890(3) -0.1274(2) 0.0484(6) Uani 0.5 1 d . . P A -1
S2 S 0.22268(19) 0.7537(6) -0.0847(3) 0.0208(8) Uani 0.5 1 d . . P A -1
C2 C 0.2643(6) 0.9118(17) -0.1295(8) 0.0285(9) Uani 0.5 1 d . . P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C21 1.7941(15) . ?
P1 C21 1.7941(15) 2 ?
P1 C11 1.7943(15) 2 ?
P1 C11 1.7943(15) . ?
C11 C16 1.395(2) . ?
C11 C12 1.396(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.394(2) . ?
C21 C26 1.400(2) . ?
C22 C23 1.393(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
S1 O1 1.342(6) . ?
S1 N1 1.546(6) . ?
S1 O2 1.575(7) . ?
S1 C1 1.954(10) . ?
C1 F3 1.248(13) . ?
C1 F1 1.295(14) . ?
C1 F2 1.336(15) . ?
N1 S2 1.725(6) . ?
O1' S2 1.438(4) . ?
O2' S2 1.333(5) . ?
F1' C2 1.399(13) . ?
F2' C2 1.389(14) . ?
F3' C2 1.331(13) . ?
S2 C2 1.700(10) . ?

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
C21 P1 C21 106.13(10) . 2 ?
C21 P1 C11 110.32(7) . 2 ?
C21 P1 C11 111.84(7) 2 2 ?
C21 P1 C11 111.84(7) . . ?
C21 P1 C11 110.32(7) 2 . ?
C11 P1 C11 106.49(10) 2 . ?
C16 C11 C12 120.19(14) . . ?
C16 C11 P1 117.84(11) . . ?
C12 C11 P1 121.94(12) . . ?
C13 C12 C11 119.17(15) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 120.52(15) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.06(15) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.07(15) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 119.97(15) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C22 C21 C26 120.73(14) . . ?
C22 C21 P1 122.58(12) . . ?
C26 C21 P1 116.67(11) . . ?
C23 C22 C21 118.92(15) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C24 C23 C22 120.33(15) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 120.51(15) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.14(15) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 119.34(14) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?
O1 S1 N1 125.3(5) . . ?
O1 S1 O2 115.1(4) . . ?
N1 S1 O2 102.5(3) . . ?
O1 S1 C1 109.2(5) . . ?
N1 S1 C1 103.7(5) . . ?
O2 S1 C1 97.1(5) . . ?
F3 C1 F1 114.6(10) . . ?
F3 C1 F2 112.7(10) . . ?
F1 C1 F2 109.3(9) . . ?
F3 C1 S1 111.7(8) . . ?
F1 C1 S1 106.6(8) . . ?
F2 C1 S1 101.0(7) . . ?
S1 N1 S2 117.9(3) . . ?
O2' S2 O1' 126.3(4) . . ?
O2' S2 C2 111.7(6) . . ?
O1' S2 C2 102.6(5) . . ?
O2' S2 N1 113.9(3) . . ?
O1' S2 N1 100.4(3) . . ?
C2 S2 N1 97.6(6) . . ?
F3' C2 F2' 104.6(7) . . ?
F3' C2 F1' 103.4(8) . . ?
F2' C2 F1' 100.7(8) . . ?
F3' C2 S2 122.4(9) . . ?
F2' C2 S2 108.1(8) . . ?
F1' C2 S2 115.2(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 P1 C11 C16 69.33(13) . . . . ?
C21 P1 C11 C16 -172.79(11) 2 . . . ?
C11 P1 C11 C16 -51.24(10) 2 . . . ?
C21 P1 C11 C12 -112.62(13) . . . . ?
C21 P1 C11 C12 5.26(15) 2 . . . ?
C11 P1 C11 C12 126.81(14) 2 . . . ?
C16 C11 C12 C13 -0.4(2) . . . . ?
P1 C11 C12 C13 -178.43(12) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C11 -0.7(2) . . . . ?
C12 C11 C16 C15 1.1(2) . . . . ?
P1 C11 C16 C15 179.16(12) . . . . ?
C21 P1 C21 C22 -126.62(14) 2 . . . ?
C11 P1 C21 C22 112.05(12) 2 . . . ?
C11 P1 C21 C22 -6.27(14) . . . . ?
C21 P1 C21 C26 51.86(10) 2 . . . ?
C11 P1 C21 C26 -69.47(13) 2 . . . ?
C11 P1 C21 C26 172.21(11) . . . . ?
C26 C21 C22 C23 1.5(2) . . . . ?
P1 C21 C22 C23 179.87(11) . . . . ?
C21 C22 C23 C24 -0.3(2) . . . . ?
C22 C23 C24 C25 -1.1(2) . . . . ?
C23 C24 C25 C26 1.3(2) . . . . ?
C24 C25 C26 C21 -0.2(2) . . . . ?
C22 C21 C26 C25 -1.2(2) . . . . ?
P1 C21 C26 C25 -179.72(11) . . . . ?
O1 S1 N1 S2 32.7(7) . . . . ?
O2 S1 N1 S2 166.24(18) . . . . ?
C1 S1 N1 S2 -93.2(6) . . . . ?
S1 N1 S2 O2' 17.7(6) . . . . ?
S1 N1 S2 O1' 155.4(2) . . . . ?
S1 N1 S2 C2 -100.2(6) . . . . ?
O2' S2 C2 F3' -176.4(9) . . . . ?
O1' S2 C2 F3' 45.6(12) . . . . ?
N1 S2 C2 F3' -56.8(11) . . . . ?
O2' S2 C2 F2' 62.2(9) . . . . ?
O1' S2 C2 F2' -75.8(9) . . . . ?
N1 S2 C2 F2' -178.3(7) . . . . ?
O2' S2 C2 F1' -49.5(11) . . . . ?
O1' S2 C2 F1' 172.6(8) . . . . ?
N1 S2 C2 F1' 70.1(10) . . . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_160808o
_database_code_depnum_ccdc_archive 'CCDC 1969436'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-12-02 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;

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

# 6. CRYSTALLOGRAPHY

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 P, C4 N3'
_chemical_formula_sum            'C28 H20 N3 P'
_chemical_formula_weight         429.44

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           54
_space_group_name_H-M_alt        'P c c a'
_space_group_name_Hall           '-P 2a 2ac'

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

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

_cell_length_a                   17.4408(2)
_cell_length_b                   6.7914(1)
_cell_length_c                   18.9369(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2243.03(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11529
_cell_measurement_theta_min      4.657
_cell_measurement_theta_max      67.218
_diffrn_orient_matrix_UB_11      0.0858909
_diffrn_orient_matrix_UB_12      -0.0463237
_diffrn_orient_matrix_UB_13      -0.0094348
_diffrn_orient_matrix_UB_21      -0.0016776
_diffrn_orient_matrix_UB_22      -0.1274419
_diffrn_orient_matrix_UB_23      0.0672473
_diffrn_orient_matrix_UB_31      -0.0206871
_diffrn_orient_matrix_UB_32      -0.1818589
_diffrn_orient_matrix_UB_33      -0.0447401

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.236
_shelx_estimated_absorpt_T_min   0.724
_shelx_estimated_absorpt_T_max   0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93753
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            19058
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.072
_diffrn_reflns_theta_max         67.312
_diffrn_reflns_theta_full        67.312
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2015
_reflns_number_gt                1862
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0650P)²+0.8100P] 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         2015
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.000000 0.53541(7) 0.250000 0.02691(18) Uani 1 2 d S T P . .
C111 C 0.06264(8) 0.37891(19) 0.30005(7) 0.0286(3) Uani 1 1 d . . . . .
C112 C 0.14197(8) 0.3914(2) 0.29483(7) 0.0323(3) Uani 1 1 d . . . . .
H112 H 0.164998 0.483963 0.263758 0.039 Uiso 1 1 calc R U . . .
C113 C 0.18724(9) 0.2671(2) 0.33558(8) 0.0383(4) Uani 1 1 d . . . . .
H113 H 0.241511 0.275733 0.332692 0.046 Uiso 1 1 calc R U . . .
C114 C 0.15386(9) 0.1311(2) 0.38024(8) 0.0382(4) Uani 1 1 d . . . . .
H114 H 0.185250 0.047893 0.408350 0.046 Uiso 1 1 calc R U . . .
C115 C 0.07479(9) 0.1156(2) 0.38420(7) 0.0363(3) Uani 1 1 d . . . . .
H115 H 0.052041 0.020102 0.414275 0.044 Uiso 1 1 calc R U . . .
C116 C 0.02902(8) 0.2391(2) 0.34442(7) 0.0340(3) Uani 1 1 d . . . . .
H116 H -0.025220 0.228961 0.347222 0.041 Uiso 1 1 calc R U . . .
C121 C 0.05425(8) 0.69009(19) 0.19146(7) 0.0307(3) Uani 1 1 d . . . . .
C122 C 0.10245(8) 0.8322(2) 0.22095(8) 0.0375(3) Uani 1 1 d . . . . .
H122 H 0.105924 0.845739 0.270777 0.045 Uiso 1 1 calc R U . . .
C123 C 0.14514(9) 0.9533(2) 0.17725(10) 0.0467(4) Uani 1 1 d . . . . .
H123 H 0.178235 1.049714 0.197078 0.056 Uiso 1 1 calc R U . . .
C124 C 0.13963(10) 0.9341(2) 0.10484(10) 0.0509(5) Uani 1 1 d . . . . .
H124 H 0.168974 1.017512 0.074988 0.061 Uiso 1 1 calc R U . . .
C125 C 0.09180(10) 0.7946(3) 0.07561(9) 0.0485(4) Uani 1 1 d . . . . .
H125 H 0.088542 0.782178 0.025729 0.058 Uiso 1 1 calc R U . . .
C126 C 0.04834(8) 0.6721(2) 0.11856(8) 0.0381(4) Uani 1 1 d . . . . .
H126 H 0.014959 0.576989 0.098342 0.046 Uiso 1 1 calc R U . . .
C1 C 0.250000 0.500000 0.52175(11) 0.0361(5) Uani 1 2 d S T P . .
N11 N 0.250000 0.500000 0.65667(10) 0.0633(7) Uani 1 2 d S T P . .
C11 C 0.250000 0.500000 0.59608(11) 0.0422(5) Uani 1 2 d S T P . .
C12 C 0.19059(10) 0.5964(2) 0.48541(8) 0.0407(4) Uani 1 1 d . . . . .
N12 N 0.14121(10) 0.6776(2) 0.45688(9) 0.0621(4) 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
P1 C111 1.7949(13) . ?
P1 C111 1.7950(13) 3 ?
P1 C121 1.7965(13) 3 ?
P1 C121 1.7966(13) . ?
C111 C112 1.390(2) . ?
C111 C116 1.3969(19) . ?
C112 C113 1.390(2) . ?
C113 C114 1.381(2) . ?
C114 C115 1.385(2) . ?
C115 C116 1.381(2) . ?
C121 C126 1.390(2) . ?
C121 C122 1.397(2) . ?
C122 C123 1.384(2) . ?
C123 C124 1.381(3) . ?
C124 C125 1.378(3) . ?
C125 C126 1.389(2) . ?
C1 C12 1.4057(19) 2_565 ?
C1 C12 1.4057(19) . ?
C1 C11 1.407(3) . ?
N11 C11 1.147(3) . ?
C12 N12 1.157(2) . ?

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
C111 P1 C111 107.38(8) . 3 ?
C111 P1 C121 109.93(6) . 3 ?
C111 P1 C121 110.58(6) 3 3 ?
C111 P1 C121 110.58(6) . . ?
C111 P1 C121 109.93(6) 3 . ?
C121 P1 C121 108.43(9) 3 . ?
C112 C111 C116 120.16(13) . . ?
C112 C111 P1 122.15(10) . . ?
C116 C111 P1 117.68(11) . . ?
C111 C112 C113 119.26(13) . . ?
C114 C113 C112 120.46(13) . . ?
C113 C114 C115 120.24(14) . . ?
C116 C115 C114 119.98(14) . . ?
C115 C116 C111 119.88(13) . . ?
C126 C121 C122 120.18(13) . . ?
C126 C121 P1 121.50(11) . . ?
C122 C121 P1 118.32(11) . . ?
C123 C122 C121 119.71(15) . . ?
C124 C123 C122 120.00(16) . . ?
C125 C124 C123 120.40(14) . . ?
C124 C125 C126 120.46(15) . . ?
C125 C126 C121 119.25(15) . . ?
C12 C1 C12 121.38(19) 2_565 . ?
C12 C1 C11 119.31(9) 2_565 . ?
C12 C1 C11 119.31(9) . . ?
N11 C11 C1 180.0 . . ?
N12 C12 C1 178.51(18) . . ?

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_090720g
_database_code_depnum_ccdc_archive 'CCDC 1969439'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-12-02 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;

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

# 6. CRYSTALLOGRAPHY

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 P, C2 N3'
_chemical_formula_sum            'C27 H22 N3 P'
_chemical_formula_weight         419.44

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

_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                   11.2149(4)
_cell_length_b                   16.9072(5)
_cell_length_c                   11.7093(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.094(3)
_cell_angle_gamma                90
_cell_volume                     2207.68(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8759
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      67.2

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.239
_shelx_estimated_absorpt_T_min   0.657
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8633
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            24169
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.611
_diffrn_reflns_theta_max         67.315
_diffrn_reflns_theta_full        67.315
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3959
_reflns_number_gt                3298
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0500P)²+1.4500P] 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         3959
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.29988(4) 0.25707(3) 0.30497(4) 0.02191(14) Uani 1 1 d . . . . .
C10 C 0.36007(16) 0.26450(11) 0.45442(16) 0.0251(4) Uani 1 1 d . . . . .
H10A H 0.447976 0.272121 0.459022 0.030 Uiso 1 1 calc R U . . .
H10B H 0.325269 0.311443 0.489035 0.030 Uiso 1 1 calc R U . . .
C11 C 0.36664(16) 0.17302(11) 0.24374(15) 0.0242(4) Uani 1 1 d . . . . .
C12 C 0.4705(2) 0.18412(13) 0.18995(19) 0.0374(5) Uani 1 1 d . . . . .
H12 H 0.501375 0.235856 0.181346 0.045 Uiso 1 1 calc R U . . .
C13 C 0.5284(2) 0.11933(14) 0.1492(2) 0.0438(6) Uani 1 1 d . . . . .
H13 H 0.599763 0.126568 0.113411 0.053 Uiso 1 1 calc R U . . .
C14 C 0.4826(2) 0.04397(13) 0.16038(19) 0.0400(5) Uani 1 1 d . . . . .
H14 H 0.520982 -0.000113 0.129697 0.048 Uiso 1 1 calc R U . . .
C15 C 0.38145(19) 0.03275(12) 0.2160(2) 0.0379(5) Uani 1 1 d . . . . .
H15 H 0.350896 -0.019096 0.224329 0.045 Uiso 1 1 calc R U . . .
C16 C 0.32438(17) 0.09694(11) 0.25958(18) 0.0304(4) Uani 1 1 d . . . . .
H16 H 0.256443 0.088987 0.300264 0.036 Uiso 1 1 calc R U . . .
C21 C 0.13929(16) 0.24945(11) 0.29774(15) 0.0228(4) Uani 1 1 d . . . . .
C22 C 0.08110(17) 0.30468(11) 0.36176(17) 0.0274(4) Uani 1 1 d . . . . .
H22 H 0.125453 0.345541 0.402549 0.033 Uiso 1 1 calc R U . . .
C23 C -0.04194(17) 0.29910(12) 0.36500(17) 0.0296(4) Uani 1 1 d . . . . .
H23 H -0.082104 0.336480 0.407897 0.035 Uiso 1 1 calc R U . . .
C24 C -0.10664(16) 0.23907(12) 0.30577(17) 0.0283(4) Uani 1 1 d . . . . .
H24 H -0.190376 0.234376 0.310582 0.034 Uiso 1 1 calc R U . . .
C25 C -0.04939(17) 0.18605(11) 0.23972(17) 0.0278(4) Uani 1 1 d . . . . .
H25 H -0.094336 0.145969 0.197732 0.033 Uiso 1 1 calc R U . . .
C26 C 0.07381(16) 0.19135(11) 0.23471(16) 0.0253(4) Uani 1 1 d . . . . .
H26 H 0.112906 0.155499 0.188525 0.030 Uiso 1 1 calc R U . . .
C31 C 0.33975(16) 0.34473(11) 0.23047(16) 0.0253(4) Uani 1 1 d . . . . .
C32 C 0.40151(16) 0.40605(11) 0.28815(17) 0.0269(4) Uani 1 1 d . . . . .
H32 H 0.423910 0.402387 0.368528 0.032 Uiso 1 1 calc R U . . .
C33 C 0.43076(18) 0.47312(11) 0.22822(19) 0.0318(4) Uani 1 1 d . . . . .
H33 H 0.473547 0.515273 0.267459 0.038 Uiso 1 1 calc R U . . .
C34 C 0.39737(19) 0.47822(12) 0.1114(2) 0.0362(5) Uani 1 1 d . . . . .
H34 H 0.417124 0.524089 0.070527 0.043 Uiso 1 1 calc R U . . .
C35 C 0.3352(2) 0.41682(13) 0.05361(19) 0.0382(5) Uani 1 1 d . . . . .
H35 H 0.312756 0.420842 -0.026719 0.046 Uiso 1 1 calc R U . . .
C36 C 0.30566(19) 0.34966(12) 0.11219(18) 0.0319(4) Uani 1 1 d . . . . .
H36 H 0.262907 0.307587 0.072699 0.038 Uiso 1 1 calc R U . . .
C41 C 0.33354(16) 0.19193(11) 0.52224(16) 0.0253(4) Uani 1 1 d . . . . .
C42 C 0.4160(2) 0.13072(13) 0.53585(18) 0.0347(5) Uani 1 1 d . . . . .
H42 H 0.488310 0.133898 0.500586 0.042 Uiso 1 1 calc R U . . .
C43 C 0.3933(2) 0.06468(13) 0.60087(19) 0.0436(6) Uani 1 1 d . . . . .
H43 H 0.449606 0.022530 0.608800 0.052 Uiso 1 1 calc R U . . .
C44 C 0.2897(2) 0.06008(13) 0.65382(18) 0.0422(5) Uani 1 1 d . . . . .
H44 H 0.275355 0.015332 0.699512 0.051 Uiso 1 1 calc R U . . .
C45 C 0.2067(2) 0.12026(13) 0.64060(18) 0.0377(5) Uani 1 1 d . . . . .
H45 H 0.134951 0.116893 0.676718 0.045 Uiso 1 1 calc R U . . .
C46 C 0.22803(18) 0.18595(12) 0.57442(17) 0.0302(4) Uani 1 1 d . . . . .
H46 H 0.170137 0.227087 0.564704 0.036 Uiso 1 1 calc R U . . .
N1 N 0.66152(15) 0.29661(11) 0.43797(16) 0.0362(4) Uani 1 1 d . . . . .
N2 N 0.72693(16) 0.55571(11) 0.45248(16) 0.0360(4) Uani 1 1 d . . . . .
N3 N 0.63141(16) 0.43194(10) 0.50685(15) 0.0334(4) Uani 1 1 d . . . . .
C1 C 0.65342(16) 0.36197(12) 0.46620(16) 0.0275(4) Uani 1 1 d . . . . .
C2 C 0.68545(17) 0.49532(12) 0.47396(17) 0.0284(4) 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
P1 C11 1.7911(18) . ?
P1 C21 1.7986(18) . ?
P1 C31 1.8000(18) . ?
P1 C10 1.8120(19) . ?
C10 C41 1.508(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.390(3) . ?
C11 C12 1.395(3) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C26 1.391(3) . ?
C21 C22 1.401(3) . ?
C22 C23 1.388(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.390(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.392(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.383(3) . ?
C31 C36 1.400(3) . ?
C32 C33 1.391(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.382(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.386(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.385(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.386(3) . ?
C41 C46 1.392(3) . ?
C42 C43 1.390(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.377(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.376(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.389(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
N1 C1 1.160(3) . ?
N2 C2 1.161(3) . ?
N3 C1 1.308(3) . ?
N3 C2 1.309(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
C11 P1 C21 112.54(9) . . ?
C11 P1 C31 108.87(9) . . ?
C21 P1 C31 109.59(8) . . ?
C11 P1 C10 108.23(8) . . ?
C21 P1 C10 108.60(8) . . ?
C31 P1 C10 108.95(9) . . ?
C41 C10 P1 112.21(13) . . ?
C41 C10 H10A 109.2 . . ?
P1 C10 H10A 109.2 . . ?
C41 C10 H10B 109.2 . . ?
P1 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C16 C11 C12 119.85(18) . . ?
C16 C11 P1 121.19(14) . . ?
C12 C11 P1 118.60(15) . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.17(19) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 119.90(19) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C26 C21 C22 120.32(17) . . ?
C26 C21 P1 123.05(14) . . ?
C22 C21 P1 116.62(14) . . ?
C23 C22 C21 119.37(18) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 120.27(18) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 120.19(17) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.19(18) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 119.58(17) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C32 C31 C36 120.58(17) . . ?
C32 C31 P1 121.20(15) . . ?
C36 C31 P1 118.21(15) . . ?
C31 C32 C33 119.84(19) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C34 C33 C32 119.8(2) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C33 C34 C35 120.40(19) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C36 C35 C34 120.4(2) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C31 119.0(2) . . ?
C35 C36 H36 120.5 . . ?
C31 C36 H36 120.5 . . ?
C42 C41 C46 118.89(18) . . ?
C42 C41 C10 120.11(17) . . ?
C46 C41 C10 120.98(17) . . ?
C41 C42 C43 120.3(2) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 H42 119.9 . . ?
C44 C43 C42 120.3(2) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C45 C44 C43 120.0(2) . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 120.0(2) . . ?
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C45 C46 C41 120.49(19) . . ?
C45 C46 H46 119.8 . . ?
C41 C46 H46 119.8 . . ?
C1 N3 C2 121.47(17) . . ?
N1 C1 N3 171.4(2) . . ?
N2 C2 N3 173.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 P1 C10 C41 -60.06(15) . . . . ?
C21 P1 C10 C41 62.39(15) . . . . ?
C31 P1 C10 C41 -178.30(12) . . . . ?
C21 P1 C11 C16 -39.18(18) . . . . ?
C31 P1 C11 C16 -160.88(15) . . . . ?
C10 P1 C11 C16 80.83(17) . . . . ?
C21 P1 C11 C12 147.67(16) . . . . ?
C31 P1 C11 C12 25.98(19) . . . . ?
C10 P1 C11 C12 -92.31(17) . . . . ?
C16 C11 C12 C13 2.2(3) . . . . ?
P1 C11 C12 C13 175.47(18) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 -2.4(4) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C11 2.3(3) . . . . ?
C12 C11 C16 C15 -3.8(3) . . . . ?
P1 C11 C16 C15 -176.85(16) . . . . ?
C11 P1 C21 C26 -10.06(18) . . . . ?
C31 P1 C21 C26 111.23(16) . . . . ?
C10 P1 C21 C26 -129.86(16) . . . . ?
C11 P1 C21 C22 168.55(14) . . . . ?
C31 P1 C21 C22 -70.17(16) . . . . ?
C10 P1 C21 C22 48.74(16) . . . . ?
C26 C21 C22 C23 2.3(3) . . . . ?
P1 C21 C22 C23 -176.33(15) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
C22 C23 C24 C25 -2.3(3) . . . . ?
C23 C24 C25 C26 1.7(3) . . . . ?
C22 C21 C26 C25 -2.9(3) . . . . ?
P1 C21 C26 C25 175.62(14) . . . . ?
C24 C25 C26 C21 0.9(3) . . . . ?
C11 P1 C31 C32 -120.77(15) . . . . ?
C21 P1 C31 C32 115.76(16) . . . . ?
C10 P1 C31 C32 -2.93(17) . . . . ?
C11 P1 C31 C36 59.77(17) . . . . ?
C21 P1 C31 C36 -63.71(17) . . . . ?
C10 P1 C31 C36 177.60(14) . . . . ?
C36 C31 C32 C33 -0.4(3) . . . . ?
P1 C31 C32 C33 -179.83(14) . . . . ?
C31 C32 C33 C34 0.3(3) . . . . ?
C32 C33 C34 C35 -0.2(3) . . . . ?
C33 C34 C35 C36 0.1(3) . . . . ?
C34 C35 C36 C31 -0.1(3) . . . . ?
C32 C31 C36 C35 0.3(3) . . . . ?
P1 C31 C36 C35 179.76(15) . . . . ?
P1 C10 C41 C42 93.24(19) . . . . ?
P1 C10 C41 C46 -88.37(19) . . . . ?
C46 C41 C42 C43 -0.2(3) . . . . ?
C10 C41 C42 C43 178.26(19) . . . . ?
C41 C42 C43 C44 -1.0(3) . . . . ?
C42 C43 C44 C45 1.3(3) . . . . ?
C43 C44 C45 C46 -0.4(3) . . . . ?
C44 C45 C46 C41 -0.8(3) . . . . ?
C42 C41 C46 C45 1.1(3) . . . . ?
C10 C41 C46 C45 -177.35(18) . . . . ?

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_110301f
_database_code_depnum_ccdc_archive 'CCDC 1969440'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-12-02 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;

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


# 6. CRYSTALLOGRAPHY

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 P, C2 F6 N O4 S2'
_chemical_formula_sum            'C27 H22 F6 N O4 P S2'
_chemical_formula_weight         633.54

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

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

_cell_length_a                   19.7732(6)
_cell_length_b                   8.4372(2)
_cell_length_c                   16.5014(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2752.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13213
_cell_measurement_theta_min      3.595
_cell_measurement_theta_max      32.5426
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0225087589
_diffrn_orient_matrix_ub_12      -0.0367615962
_diffrn_orient_matrix_ub_13      0.0158117813
_diffrn_orient_matrix_ub_21      0.0190861144
_diffrn_orient_matrix_ub_22      -0.0167506571
_diffrn_orient_matrix_ub_23      -0.031953415
_diffrn_orient_matrix_ub_31      0.0785428545
_diffrn_orient_matrix_ub_32      0.0146106225
_diffrn_orient_matrix_ub_33      0.0032622916

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0344
-1 0 -1 0.0406
-2 0 -1 0.0631
3 0 1 0.0269
0 1 0 0.1615
0 -1 0 0.2536
1 2 -23 0.0873
1 0 -23 0.0726
_exptl_absorpt_coefficient_mu    0.328
_shelx_estimated_absorpt_T_min   0.875
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   
;
       CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_reflns_number            31268
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.604
_diffrn_reflns_theta_max         32.653
_diffrn_reflns_theta_full        32.000
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.945
_reflns_number_total             9173
_reflns_number_gt                7256
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.848
_reflns_Friedel_fraction_max     0.861
_reflns_Friedel_fraction_full    0.903

_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0291P)²] 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 2769 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         9173
_refine_ls_number_parameters     370
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0612
_refine_ls_wR_factor_gt          0.0593
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_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 0.11681(2) 0.67384(5) 0.46475(3) 0.01394(10) Uani 1 1 d . . . . .
C10 C 0.08979(10) 0.8781(2) 0.47566(13) 0.0171(4) Uani 1 1 d . . . . .
H10A H 0.056806 0.903536 0.432437 0.021 Uiso 1 1 calc R U . . .
H10B H 0.066742 0.891136 0.528501 0.021 Uiso 1 1 calc R U . . .
C21 C 0.18353(10) 0.6345(2) 0.53583(13) 0.0147(4) Uani 1 1 d . . . . .
C22 C 0.16664(11) 0.5796(2) 0.61243(14) 0.0209(4) Uani 1 1 d . . . . .
H22 H 0.120719 0.558725 0.625593 0.025 Uiso 1 1 calc R U . . .
C23 C 0.21685(12) 0.5551(3) 0.66984(15) 0.0266(5) Uani 1 1 d . . . . .
H23 H 0.205275 0.517316 0.722278 0.032 Uiso 1 1 calc R U . . .
C24 C 0.28349(11) 0.5854(3) 0.65091(15) 0.0253(5) Uani 1 1 d . . . . .
H24 H 0.317748 0.567562 0.690221 0.030 Uiso 1 1 calc R U . . .
C25 C 0.30071(11) 0.6418(3) 0.57506(14) 0.0233(5) Uani 1 1 d . . . . .
H25 H 0.346742 0.662602 0.562443 0.028 Uiso 1 1 calc R U . . .
C26 C 0.25089(10) 0.6681(2) 0.51708(13) 0.0200(4) Uani 1 1 d . . . . .
H26 H 0.262576 0.708584 0.465222 0.024 Uiso 1 1 calc R U . . .
C31 C 0.14194(10) 0.6393(2) 0.36175(12) 0.0148(4) Uani 1 1 d . . . . .
C32 C 0.19318(10) 0.5331(2) 0.34174(16) 0.0207(4) Uani 1 1 d . . . . .
H32 H 0.219916 0.486315 0.383148 0.025 Uiso 1 1 calc R U . . .
C33 C 0.20510(11) 0.4959(3) 0.26083(14) 0.0238(5) Uani 1 1 d . . . . .
H33 H 0.240441 0.424589 0.246973 0.029 Uiso 1 1 calc R U . . .
C34 C 0.16582(11) 0.5621(2) 0.20079(14) 0.0233(5) Uani 1 1 d . . . . .
H34 H 0.173224 0.533678 0.145788 0.028 Uiso 1 1 calc R U . . .
C35 C 0.11562(11) 0.6697(2) 0.22029(14) 0.0234(5) Uani 1 1 d . . . . .
H35 H 0.089599 0.717366 0.178480 0.028 Uiso 1 1 calc R U . . .
C36 C 0.10317(10) 0.7082(2) 0.30020(14) 0.0196(4) Uani 1 1 d . . . . .
H36 H 0.068333 0.781285 0.313389 0.024 Uiso 1 1 calc R U . . .
C41 C 0.04750(10) 0.5434(2) 0.48611(12) 0.0156(4) Uani 1 1 d . . . . .
C42 C 0.06047(11) 0.3810(2) 0.49321(15) 0.0226(5) Uani 1 1 d . . . . .
H42 H 0.105537 0.342618 0.489779 0.027 Uiso 1 1 calc R U . . .
C43 C 0.00762(11) 0.2767(3) 0.50521(15) 0.0256(5) Uani 1 1 d . . . . .
H43 H 0.016512 0.166787 0.511516 0.031 Uiso 1 1 calc R U . . .
C44 C -0.05817(11) 0.3317(3) 0.50807(13) 0.0227(5) Uani 1 1 d . . . . .
H44 H -0.094401 0.259110 0.515230 0.027 Uiso 1 1 calc R U . . .
C45 C -0.07141(11) 0.4910(3) 0.50061(14) 0.0237(5) Uani 1 1 d . . . . .
H45 H -0.116771 0.527900 0.502517 0.028 Uiso 1 1 calc R U . . .
C46 C -0.01858(10) 0.5988(2) 0.49024(14) 0.0210(4) Uani 1 1 d . . . . .
H46 H -0.027719 0.709077 0.486041 0.025 Uiso 1 1 calc R U . . .
C111 C 0.14863(10) 0.9930(2) 0.47080(14) 0.0161(4) Uani 1 1 d . . . . .
C112 C 0.17504(11) 1.0570(2) 0.54165(14) 0.0214(5) Uani 1 1 d . . . . .
H112 H 0.157246 1.025383 0.592628 0.026 Uiso 1 1 calc R U . . .
C113 C 0.22723(11) 1.1667(2) 0.53840(16) 0.0239(5) Uani 1 1 d . . . . .
H113 H 0.243846 1.212996 0.586950 0.029 Uiso 1 1 calc R U . . .
C114 C 0.25517(10) 1.2088(2) 0.46444(17) 0.0267(5) Uani 1 1 d . . . . .
H114 H 0.291687 1.281866 0.462219 0.032 Uiso 1 1 calc R U . . .
C115 C 0.22962(13) 1.1440(3) 0.39407(16) 0.0300(6) Uani 1 1 d . . . . .
H115 H 0.248927 1.172112 0.343348 0.036 Uiso 1 1 calc R U . . .
C116 C 0.17603(12) 1.0382(3) 0.39666(14) 0.0250(5) Uani 1 1 d . . . . .
H116 H 0.157986 0.996468 0.347752 0.030 Uiso 1 1 calc R U . . .
N1 N 0.02148(8) 0.99231(19) 0.80684(11) 0.0187(4) Uani 1 1 d . . . . .
S1 S 0.09330(2) 1.02214(5) 0.84586(3) 0.01643(10) Uani 1 1 d . . . . .
O11 O 0.14569(7) 0.91369(16) 0.82531(10) 0.0235(3) Uani 1 1 d . . . . .
O12 O 0.08332(8) 1.06186(17) 0.92943(10) 0.0263(4) Uani 1 1 d . . . . .
C1 C 0.11898(11) 1.2117(2) 0.79994(15) 0.0224(4) Uani 1 1 d . . . . .
F11 F 0.07019(7) 1.31870(15) 0.80763(10) 0.0372(4) Uani 1 1 d . . . . .
F12 F 0.17358(7) 1.26775(15) 0.83682(10) 0.0360(3) Uani 1 1 d . . . . .
F13 F 0.13257(8) 1.19615(15) 0.72184(9) 0.0378(3) Uani 1 1 d . . . . .
S2 S 0.00961(3) 0.90329(6) 0.72398(4) 0.02048(11) Uani 1 1 d . . . . .
O21 O 0.06683(9) 0.89098(19) 0.67187(10) 0.0319(4) Uani 1 1 d . . . . .
O22 O -0.05323(9) 0.9550(2) 0.69098(13) 0.0458(5) Uani 1 1 d . . . . .
C2 C -0.00610(14) 0.6992(3) 0.75614(16) 0.0332(6) Uani 1 1 d . . . . .
F21 F -0.01367(9) 0.60882(17) 0.69049(10) 0.0484(4) Uani 1 1 d . . . . .
F22 F 0.04493(9) 0.64384(16) 0.79865(11) 0.0497(4) Uani 1 1 d . . . . .
F23 F -0.06196(9) 0.69074(19) 0.80020(10) 0.0540(5) 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
P1 C41 1.793(2) . ?
P1 C31 1.795(2) . ?
P1 C21 1.796(2) . ?
P1 C10 1.8132(18) . ?
C10 C111 1.517(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C21 C22 1.387(3) . ?
C21 C26 1.397(3) . ?
C22 C23 1.388(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.391(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.392(3) . ?
C31 C36 1.399(3) . ?
C32 C33 1.392(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.377(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.380(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C46 1.390(3) . ?
C41 C42 1.398(3) . ?
C42 C43 1.380(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.382(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.375(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.396(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C111 C112 1.389(3) . ?
C111 C116 1.391(3) . ?
C112 C113 1.387(3) . ?
C112 H112 0.9500 . ?
C113 C114 1.386(4) . ?
C113 H113 0.9500 . ?
C114 C115 1.379(4) . ?
C114 H114 0.9500 . ?
C115 C116 1.386(3) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
N1 S2 1.5777(19) . ?
N1 S1 1.5794(17) . ?
S1 O11 1.4232(15) . ?
S1 O12 1.4329(17) . ?
S1 C1 1.841(2) . ?
C1 F13 1.323(3) . ?
C1 F12 1.327(2) . ?
C1 F11 1.328(3) . ?
S2 O21 1.4249(18) . ?
S2 O22 1.4251(18) . ?
S2 C2 1.828(2) . ?
C2 F22 1.315(3) . ?
C2 F23 1.324(3) . ?
C2 F21 1.333(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
C41 P1 C31 107.35(9) . . ?
C41 P1 C21 108.63(9) . . ?
C31 P1 C21 112.64(9) . . ?
C41 P1 C10 109.80(9) . . ?
C31 P1 C10 109.27(9) . . ?
C21 P1 C10 109.11(9) . . ?
C111 C10 P1 112.11(13) . . ?
C111 C10 H10A 109.2 . . ?
P1 C10 H10A 109.2 . . ?
C111 C10 H10B 109.2 . . ?
P1 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C22 C21 C26 120.0(2) . . ?
C22 C21 P1 118.69(16) . . ?
C26 C21 P1 121.22(16) . . ?
C21 C22 C23 120.0(2) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 120.1(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.3(2) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C26 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 119.4(2) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?
C32 C31 C36 119.6(2) . . ?
C32 C31 P1 122.06(17) . . ?
C36 C31 P1 117.93(15) . . ?
C33 C32 C31 119.7(2) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C34 C33 C32 120.2(2) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 120.2(2) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C36 C35 C34 120.3(2) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C31 119.88(19) . . ?
C35 C36 H36 120.1 . . ?
C31 C36 H36 120.1 . . ?
C46 C41 C42 119.87(18) . . ?
C46 C41 P1 121.45(15) . . ?
C42 C41 P1 118.54(15) . . ?
C43 C42 C41 119.8(2) . . ?
C43 C42 H42 120.1 . . ?
C41 C42 H42 120.1 . . ?
C42 C43 C44 120.2(2) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C45 C44 C43 120.3(2) . . ?
C45 C44 H44 119.9 . . ?
C43 C44 H44 119.9 . . ?
C44 C45 C46 120.4(2) . . ?
C44 C45 H45 119.8 . . ?
C46 C45 H45 119.8 . . ?
C41 C46 C45 119.36(19) . . ?
C41 C46 H46 120.3 . . ?
C45 C46 H46 120.3 . . ?
C112 C111 C116 119.16(18) . . ?
C112 C111 C10 119.5(2) . . ?
C116 C111 C10 121.4(2) . . ?
C113 C112 C111 120.4(2) . . ?
C113 C112 H112 119.8 . . ?
C111 C112 H112 119.8 . . ?
C114 C113 C112 120.1(2) . . ?
C114 C113 H113 119.9 . . ?
C112 C113 H113 119.9 . . ?
C115 C114 C113 119.57(19) . . ?
C115 C114 H114 120.2 . . ?
C113 C114 H114 120.2 . . ?
C114 C115 C116 120.6(2) . . ?
C114 C115 H115 119.7 . . ?
C116 C115 H115 119.7 . . ?
C115 C116 C111 120.1(2) . . ?
C115 C116 H116 120.0 . . ?
C111 C116 H116 120.0 . . ?
S2 N1 S1 124.26(11) . . ?
O11 S1 O12 118.68(10) . . ?
O11 S1 N1 117.06(9) . . ?
O12 S1 N1 107.80(10) . . ?
O11 S1 C1 105.05(10) . . ?
O12 S1 C1 103.35(10) . . ?
N1 S1 C1 102.63(10) . . ?
F13 C1 F12 108.47(19) . . ?
F13 C1 F11 107.94(18) . . ?
F12 C1 F11 107.74(17) . . ?
F13 C1 S1 111.78(14) . . ?
F12 C1 S1 110.22(15) . . ?
F11 C1 S1 110.56(16) . . ?
O21 S2 O22 118.95(12) . . ?
O21 S2 N1 116.07(9) . . ?
O22 S2 N1 108.36(10) . . ?
O21 S2 C2 103.97(11) . . ?
O22 S2 C2 104.56(12) . . ?
N1 S2 C2 102.83(11) . . ?
F22 C2 F23 109.2(2) . . ?
F22 C2 F21 108.4(2) . . ?
F23 C2 F21 108.8(2) . . ?
F22 C2 S2 111.05(16) . . ?
F23 C2 S2 110.60(18) . . ?
F21 C2 S2 108.78(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C41 P1 C10 C111 171.38(15) . . . . ?
C31 P1 C10 C111 -71.13(17) . . . . ?
C21 P1 C10 C111 52.42(18) . . . . ?
C41 P1 C21 C22 -29.77(18) . . . . ?
C31 P1 C21 C22 -148.55(15) . . . . ?
C10 P1 C21 C22 89.92(17) . . . . ?
C41 P1 C21 C26 154.56(16) . . . . ?
C31 P1 C21 C26 35.78(18) . . . . ?
C10 P1 C21 C26 -85.75(18) . . . . ?
C26 C21 C22 C23 -1.3(3) . . . . ?
P1 C21 C22 C23 -177.03(17) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C23 C24 C25 C26 -0.1(3) . . . . ?
C24 C25 C26 C21 -1.1(3) . . . . ?
C22 C21 C26 C25 1.8(3) . . . . ?
P1 C21 C26 C25 177.41(16) . . . . ?
C41 P1 C31 C32 -93.53(17) . . . . ?
C21 P1 C31 C32 26.01(19) . . . . ?
C10 P1 C31 C32 147.45(16) . . . . ?
C41 P1 C31 C36 79.01(16) . . . . ?
C21 P1 C31 C36 -161.46(14) . . . . ?
C10 P1 C31 C36 -40.02(17) . . . . ?
C36 C31 C32 C33 -0.4(3) . . . . ?
P1 C31 C32 C33 172.05(16) . . . . ?
C31 C32 C33 C34 -0.9(3) . . . . ?
C32 C33 C34 C35 2.0(3) . . . . ?
C33 C34 C35 C36 -1.9(3) . . . . ?
C34 C35 C36 C31 0.7(3) . . . . ?
C32 C31 C36 C35 0.4(3) . . . . ?
P1 C31 C36 C35 -172.27(15) . . . . ?
C31 P1 C41 C46 -104.65(18) . . . . ?
C21 P1 C41 C46 133.28(17) . . . . ?
C10 P1 C41 C46 14.0(2) . . . . ?
C31 P1 C41 C42 71.00(19) . . . . ?
C21 P1 C41 C42 -51.1(2) . . . . ?
C10 P1 C41 C42 -170.32(17) . . . . ?
C46 C41 C42 C43 -0.7(3) . . . . ?
P1 C41 C42 C43 -176.46(18) . . . . ?
C41 C42 C43 C44 1.7(4) . . . . ?
C42 C43 C44 C45 -1.3(4) . . . . ?
C43 C44 C45 C46 -0.1(4) . . . . ?
C42 C41 C46 C45 -0.7(3) . . . . ?
P1 C41 C46 C45 174.92(17) . . . . ?
C44 C45 C46 C41 1.1(3) . . . . ?
P1 C10 C111 C112 -101.20(19) . . . . ?
P1 C10 C111 C116 80.0(2) . . . . ?
C116 C111 C112 C113 1.2(3) . . . . ?
C10 C111 C112 C113 -177.66(18) . . . . ?
C111 C112 C113 C114 -2.5(3) . . . . ?
C112 C113 C114 C115 1.6(3) . . . . ?
C113 C114 C115 C116 0.5(3) . . . . ?
C114 C115 C116 C111 -1.7(4) . . . . ?
C112 C111 C116 C115 0.9(3) . . . . ?
C10 C111 C116 C115 179.7(2) . . . . ?
S2 N1 S1 O11 -26.20(17) . . . . ?
S2 N1 S1 O12 -163.10(12) . . . . ?
S2 N1 S1 C1 88.21(14) . . . . ?
O11 S1 C1 F13 52.98(18) . . . . ?
O12 S1 C1 F13 178.06(16) . . . . ?
N1 S1 C1 F13 -69.90(17) . . . . ?
O11 S1 C1 F12 -67.73(18) . . . . ?
O12 S1 C1 F12 57.34(18) . . . . ?
N1 S1 C1 F12 169.38(15) . . . . ?
O11 S1 C1 F11 173.26(15) . . . . ?
O12 S1 C1 F11 -61.67(17) . . . . ?
N1 S1 C1 F11 50.37(18) . . . . ?
S1 N1 S2 O21 -18.54(17) . . . . ?
S1 N1 S2 O22 -155.45(14) . . . . ?
S1 N1 S2 C2 94.23(15) . . . . ?
O21 S2 C2 F22 63.78(19) . . . . ?
O22 S2 C2 F22 -170.77(18) . . . . ?
N1 S2 C2 F22 -57.63(19) . . . . ?
O21 S2 C2 F23 -174.87(18) . . . . ?
O22 S2 C2 F23 -49.4(2) . . . . ?
N1 S2 C2 F23 63.7(2) . . . . ?
O21 S2 C2 F21 -55.5(2) . . . . ?
O22 S2 C2 F21 70.0(2) . . . . ?
N1 S2 C2 F21 -176.89(17) . . . . ?

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
_geom_hbond_publ_flag
C10 H10B O21 0.99 2.37 3.271(3) 151.7 . yes
C26 H26 F12 0.95 2.52 3.433(3) 162.2 3_544 yes
C36 H36 N1 0.95 2.61 3.532(3) 163.5 2_574 yes
C46 H46 O12 0.95 2.41 3.292(3) 154.1 2_574 yes

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_090604j
_database_code_depnum_ccdc_archive 'CCDC 1969438'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2019-12-02 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;

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

# 6. CRYSTALLOGRAPHY

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 P, C N S'
_chemical_formula_sum            'C26 H22 N P S'
_chemical_formula_weight         411.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.8950(4)
_cell_length_b                   12.8564(5)
_cell_length_c                   18.7165(9)
_cell_angle_alpha                70.204(4)
_cell_angle_beta                 84.593(4)
_cell_angle_gamma                76.784(4)
_cell_volume                     2180.60(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3679
_cell_measurement_theta_min      2.9320
_cell_measurement_theta_max      28.2460
_diffrn_orient_matrix_UB_11      0.0488276
_diffrn_orient_matrix_UB_12      -0.0475322
_diffrn_orient_matrix_UB_13      0.0214141
_diffrn_orient_matrix_UB_21      -0.0183861
_diffrn_orient_matrix_UB_22      0.0164907
_diffrn_orient_matrix_UB_23      0.0327484
_diffrn_orient_matrix_UB_31      -0.0519747
_diffrn_orient_matrix_UB_32      -0.0326427
_diffrn_orient_matrix_UB_33      0.0095796

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0263 -0.0000 -0.0000 1.0000 0.0214 0.0327 0.0096
0 0 -1 0.0185 0.0000 0.0000 -1.0000 -0.0214 -0.0327 -0.0096
-1 -1 0 0.1093 -1.0000 -1.0000 0.0000 -0.0013 0.0019 0.0846
1 1 0 0.0969 1.0000 1.0000 -0.0000 0.0013 -0.0019 -0.0846
0 -1 0 0.0572 -0.0000 -1.0000 0.0000 0.0475 -0.0165 0.0326
-1 0 0 0.1295 -1.0000 -0.0000 -0.0000 -0.0488 0.0184 0.0520
1 0 0 0.1230 1.0000 0.0000 0.0000 0.0488 -0.0184 -0.0520
0 1 1 0.0284 -0.0000 1.0000 1.0000 -0.0261 0.0492 -0.0231
0 -1 -1 0.0406 0.0000 -1.0000 -1.0000 0.0261 -0.0492 0.0231
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur-S'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0009
_diffrn_reflns_number            18157
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.911
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8913
_reflns_number_gt                5838
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_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)+(0.0450P)²+1.5000P] 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         8913
_refine_ls_number_parameters     523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.32908(8) 0.19761(7) 0.36079(5) 0.0243(2) Uani 1 1 d . . . . .
C1 C 0.1976(3) 0.2726(3) 0.28960(17) 0.0252(7) Uani 1 1 d . . . . .
H1A H 0.179077 0.219439 0.265759 0.030 Uiso 1 1 calc R U . . .
H1B H 0.110521 0.298927 0.314949 0.030 Uiso 1 1 calc R U . . .
C111 C 0.2368(3) 0.3734(3) 0.22798(17) 0.0247(7) Uani 1 1 d . . . . .
C112 C 0.3026(3) 0.3584(3) 0.16237(17) 0.0265(7) Uani 1 1 d . . . . .
H112 H 0.326901 0.285013 0.157841 0.032 Uiso 1 1 calc R U . . .
C113 C 0.3329(3) 0.4500(3) 0.10347(19) 0.0332(9) Uani 1 1 d . . . . .
H113 H 0.377688 0.439368 0.058533 0.040 Uiso 1 1 calc R U . . .
C114 C 0.2984(3) 0.5570(3) 0.1097(2) 0.0353(9) Uani 1 1 d . . . . .
H114 H 0.318808 0.619759 0.068964 0.042 Uiso 1 1 calc R U . . .
C115 C 0.2344(3) 0.5729(3) 0.1752(2) 0.0330(8) Uani 1 1 d . . . . .
H115 H 0.212119 0.646262 0.179816 0.040 Uiso 1 1 calc R U . . .
C116 C 0.2027(3) 0.4813(3) 0.23415(19) 0.0292(8) Uani 1 1 d . . . . .
H116 H 0.157457 0.492309 0.278905 0.035 Uiso 1 1 calc R U . . .
C121 C 0.3497(3) 0.2811(3) 0.41724(17) 0.0255(7) Uani 1 1 d . . . . .
C122 C 0.2310(3) 0.3443(3) 0.44064(18) 0.0293(8) Uani 1 1 d . . . . .
H122 H 0.142971 0.350150 0.421513 0.035 Uiso 1 1 calc R U . . .
C123 C 0.2412(4) 0.3983(3) 0.49155(19) 0.0345(8) Uani 1 1 d . . . . .
H123 H 0.160251 0.441310 0.507586 0.041 Uiso 1 1 calc R U . . .
C124 C 0.3700(4) 0.3898(3) 0.5194(2) 0.0359(9) Uani 1 1 d . . . . .
H124 H 0.376921 0.427781 0.554085 0.043 Uiso 1 1 calc R U . . .
C125 C 0.4881(4) 0.3263(3) 0.49693(19) 0.0347(9) Uani 1 1 d . . . . .
H125 H 0.575749 0.320695 0.516318 0.042 Uiso 1 1 calc R U . . .
C126 C 0.4792(3) 0.2711(3) 0.44654(18) 0.0297(8) Uani 1 1 d . . . . .
H126 H 0.560208 0.226505 0.431756 0.036 Uiso 1 1 calc R U . . .
C131 C 0.2669(3) 0.0767(3) 0.42249(18) 0.0267(7) Uani 1 1 d . . . . .
C132 C 0.2692(3) 0.0521(3) 0.50116(19) 0.0326(8) Uani 1 1 d . . . . .
H132 H 0.309198 0.095847 0.521956 0.039 Uiso 1 1 calc R U . . .
C133 C 0.2124(3) -0.0366(3) 0.5483(2) 0.0343(9) Uani 1 1 d . . . . .
H133 H 0.212596 -0.053295 0.601777 0.041 Uiso 1 1 calc R U . . .
C134 C 0.1560(3) -0.1008(3) 0.51877(19) 0.0317(8) Uani 1 1 d . . . . .
H134 H 0.118457 -0.161906 0.552114 0.038 Uiso 1 1 calc R U . . .
C135 C 0.1527(3) -0.0779(3) 0.44078(19) 0.0319(8) Uani 1 1 d . . . . .
H135 H 0.113514 -0.122944 0.420792 0.038 Uiso 1 1 calc R U . . .
C136 C 0.2078(3) 0.0121(3) 0.39232(19) 0.0305(8) Uani 1 1 d . . . . .
H136 H 0.205209 0.029496 0.338862 0.037 Uiso 1 1 calc R U . . .
C141 C 0.4925(3) 0.1586(3) 0.31588(17) 0.0242(7) Uani 1 1 d . . . . .
C142 C 0.5388(3) 0.0501(3) 0.31244(19) 0.0325(8) Uani 1 1 d . . . . .
H142 H 0.484310 -0.005356 0.334057 0.039 Uiso 1 1 calc R U . . .
C143 C 0.6658(3) 0.0230(3) 0.2771(2) 0.0373(9) Uani 1 1 d . . . . .
H143 H 0.697303 -0.050849 0.273911 0.045 Uiso 1 1 calc R U . . .
C144 C 0.7462(3) 0.1032(3) 0.24662(18) 0.0329(8) Uani 1 1 d . . . . .
H144 H 0.833160 0.083775 0.223054 0.039 Uiso 1 1 calc R U . . .
C145 C 0.7012(3) 0.2105(3) 0.25018(17) 0.0317(8) Uani 1 1 d . . . . .
H145 H 0.757488 0.264851 0.229625 0.038 Uiso 1 1 calc R U . . .
C146 C 0.5741(3) 0.2396(3) 0.28364(17) 0.0290(8) Uani 1 1 d . . . . .
H146 H 0.541926 0.314505 0.284793 0.035 Uiso 1 1 calc R U . . .
P2 P 0.67978(7) 0.73892(7) 0.15750(4) 0.01885(19) Uani 1 1 d . . . . .
C2 C 0.6113(3) 0.8610(2) 0.07741(16) 0.0212(7) Uani 1 1 d . . . . .
H2A H 0.578677 0.926805 0.095402 0.025 Uiso 1 1 calc R U . . .
H2B H 0.687843 0.877968 0.040149 0.025 Uiso 1 1 calc R U . . .
C211 C 0.4926(3) 0.8484(2) 0.03698(16) 0.0193(7) Uani 1 1 d . . . . .
C212 C 0.3552(3) 0.8799(3) 0.05874(17) 0.0242(7) Uani 1 1 d . . . . .
H212 H 0.334019 0.905473 0.101356 0.029 Uiso 1 1 calc R U . . .
C213 C 0.2481(3) 0.8737(3) 0.01731(17) 0.0249(7) Uani 1 1 d . . . . .
H213 H 0.154091 0.894506 0.032197 0.030 Uiso 1 1 calc R U . . .
C214 C 0.2787(3) 0.8375(3) -0.04499(18) 0.0256(7) Uani 1 1 d . . . . .
H214 H 0.205691 0.834272 -0.073178 0.031 Uiso 1 1 calc R U . . .
C215 C 0.4157(3) 0.8060(3) -0.06650(17) 0.0251(7) Uani 1 1 d . . . . .
H215 H 0.436527 0.780699 -0.109235 0.030 Uiso 1 1 calc R U . . .
C216 C 0.5225(3) 0.8114(2) -0.02554(17) 0.0221(7) Uani 1 1 d . . . . .
H216 H 0.616371 0.789632 -0.040358 0.027 Uiso 1 1 calc R U . . .
C221 C 0.7455(3) 0.6172(2) 0.12873(16) 0.0187(7) Uani 1 1 d . . . . .
C222 C 0.8879(3) 0.5819(3) 0.11974(17) 0.0258(7) Uani 1 1 d . . . . .
H222 H 0.949974 0.622324 0.128920 0.031 Uiso 1 1 calc R U . . .
C223 C 0.9392(3) 0.4878(3) 0.09738(19) 0.0310(8) Uani 1 1 d . . . . .
H223 H 1.036505 0.463678 0.091381 0.037 Uiso 1 1 calc R U . . .
C224 C 0.8496(3) 0.4291(3) 0.08380(17) 0.0283(8) Uani 1 1 d . . . . .
H224 H 0.885221 0.364652 0.068370 0.034 Uiso 1 1 calc R U . . .
C225 C 0.7071(3) 0.4641(3) 0.09271(17) 0.0260(7) Uani 1 1 d . . . . .
H225 H 0.645637 0.422811 0.084024 0.031 Uiso 1 1 calc R U . . .
C226 C 0.6547(3) 0.5584(3) 0.11407(17) 0.0227(7) Uani 1 1 d . . . . .
H226 H 0.557199 0.583274 0.118806 0.027 Uiso 1 1 calc R U . . .
C231 C 0.8158(3) 0.7732(3) 0.19658(17) 0.0217(7) Uani 1 1 d . . . . .
C232 C 0.8863(3) 0.8563(3) 0.15255(19) 0.0275(8) Uani 1 1 d . . . . .
H232 H 0.866058 0.893259 0.100241 0.033 Uiso 1 1 calc R U . . .
C233 C 0.9862(3) 0.8846(3) 0.1856(2) 0.0337(8) Uani 1 1 d . . . . .
H233 H 1.035086 0.940796 0.155918 0.040 Uiso 1 1 calc R U . . .
C234 C 1.0145(3) 0.8310(3) 0.2618(2) 0.0375(9) Uani 1 1 d . . . . .
H234 H 1.080934 0.852388 0.284439 0.045 Uiso 1 1 calc R U . . .
C235 C 0.9478(3) 0.7471(3) 0.3053(2) 0.0371(9) Uani 1 1 d . . . . .
H235 H 0.969840 0.709487 0.357376 0.045 Uiso 1 1 calc R U . . .
C236 C 0.8480(3) 0.7176(3) 0.27271(19) 0.0300(8) Uani 1 1 d . . . . .
H236 H 0.801847 0.659493 0.302400 0.036 Uiso 1 1 calc R U . . .
C241 C 0.5480(3) 0.7106(3) 0.22941(16) 0.0201(7) Uani 1 1 d . . . . .
C242 C 0.4637(3) 0.8024(3) 0.24732(18) 0.0247(7) Uani 1 1 d . . . . .
H242 H 0.474472 0.877327 0.220160 0.030 Uiso 1 1 calc R U . . .
C243 C 0.3651(3) 0.7829(3) 0.30479(18) 0.0299(8) Uani 1 1 d . . . . .
H243 H 0.309094 0.844834 0.317675 0.036 Uiso 1 1 calc R U . . .
C244 C 0.3464(3) 0.6747(3) 0.34380(18) 0.0297(8) Uani 1 1 d . . . . .
H244 H 0.276216 0.662646 0.382175 0.036 Uiso 1 1 calc R U . . .
C245 C 0.4301(3) 0.5846(3) 0.32684(17) 0.0299(8) Uani 1 1 d . . . . .
H245 H 0.418634 0.509965 0.354338 0.036 Uiso 1 1 calc R U . . .
C246 C 0.5314(3) 0.6018(3) 0.26967(17) 0.0233(7) Uani 1 1 d . . . . .
H246 H 0.589039 0.539144 0.258312 0.028 Uiso 1 1 calc R U . . .
S1 S 0.09566(8) 0.16357(8) 0.06307(5) 0.0337(2) Uani 1 1 d . . . . .
C11 C 0.1803(3) 0.1067(3) 0.1440(2) 0.0285(8) Uani 1 1 d . . . . .
N11 N 0.2404(3) 0.0660(3) 0.20014(18) 0.0435(8) Uani 1 1 d . . . . .
S2 S 0.14973(10) 0.59446(8) 0.64751(6) 0.0464(3) Uani 1 1 d . . . . .
C21 C 0.1283(3) 0.6320(3) 0.5549(2) 0.0366(9) Uani 1 1 d . . . . .
N21 N 0.1088(3) 0.6612(3) 0.4894(2) 0.0474(9) 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
P1 C131 1.793(3) . ?
P1 C121 1.794(3) . ?
P1 C141 1.797(3) . ?
P1 C1 1.811(3) . ?
C1 C111 1.514(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C111 C112 1.386(4) . ?
C111 C116 1.393(5) . ?
C112 C113 1.383(4) . ?
C112 H112 0.9500 . ?
C113 C114 1.382(5) . ?
C113 H113 0.9500 . ?
C114 C115 1.381(5) . ?
C114 H114 0.9500 . ?
C115 C116 1.388(4) . ?
C115 H115 0.9500 . ?
C116 H116 0.9500 . ?
C121 C122 1.393(4) . ?
C121 C126 1.403(4) . ?
C122 C123 1.378(5) . ?
C122 H122 0.9500 . ?
C123 C124 1.389(5) . ?
C123 H123 0.9500 . ?
C124 C125 1.384(5) . ?
C124 H124 0.9500 . ?
C125 C126 1.378(5) . ?
C125 H125 0.9500 . ?
C126 H126 0.9500 . ?
C131 C136 1.397(5) . ?
C131 C132 1.399(4) . ?
C132 C133 1.384(5) . ?
C132 H132 0.9500 . ?
C133 C134 1.369(5) . ?
C133 H133 0.9500 . ?
C134 C135 1.390(5) . ?
C134 H134 0.9500 . ?
C135 C136 1.394(4) . ?
C135 H135 0.9500 . ?
C136 H136 0.9500 . ?
C141 C142 1.387(5) . ?
C141 C146 1.402(5) . ?
C142 C143 1.391(5) . ?
C142 H142 0.9500 . ?
C143 C144 1.382(5) . ?
C143 H143 0.9500 . ?
C144 C145 1.372(5) . ?
C144 H144 0.9500 . ?
C145 C146 1.382(4) . ?
C145 H145 0.9500 . ?
C146 H146 0.9500 . ?
P2 C241 1.788(3) . ?
P2 C221 1.790(3) . ?
P2 C231 1.793(3) . ?
P2 C2 1.812(3) . ?
C2 C211 1.522(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C211 C216 1.390(4) . ?
C211 C212 1.391(4) . ?
C212 C213 1.402(4) . ?
C212 H212 0.9500 . ?
C213 C214 1.380(5) . ?
C213 H213 0.9500 . ?
C214 C215 1.386(4) . ?
C214 H214 0.9500 . ?
C215 C216 1.390(4) . ?
C215 H215 0.9500 . ?
C216 H216 0.9500 . ?
C221 C222 1.391(4) . ?
C221 C226 1.397(4) . ?
C222 C223 1.385(5) . ?
C222 H222 0.9500 . ?
C223 C224 1.378(5) . ?
C223 H223 0.9500 . ?
C224 C225 1.391(4) . ?
C224 H224 0.9500 . ?
C225 C226 1.379(4) . ?
C225 H225 0.9500 . ?
C226 H226 0.9500 . ?
C231 C236 1.391(4) . ?
C231 C232 1.394(4) . ?
C232 C233 1.388(5) . ?
C232 H232 0.9500 . ?
C233 C234 1.381(5) . ?
C233 H233 0.9500 . ?
C234 C235 1.375(5) . ?
C234 H234 0.9500 . ?
C235 C236 1.391(5) . ?
C235 H235 0.9500 . ?
C236 H236 0.9500 . ?
C241 C246 1.385(4) . ?
C241 C242 1.402(4) . ?
C242 C243 1.380(4) . ?
C242 H242 0.9500 . ?
C243 C244 1.380(5) . ?
C243 H243 0.9500 . ?
C244 C245 1.375(5) . ?
C244 H244 0.9500 . ?
C245 C246 1.392(4) . ?
C245 H245 0.9500 . ?
C246 H246 0.9500 . ?
S1 C11 1.654(4) . ?
C11 N11 1.156(4) . ?
S2 C21 1.655(4) . ?
C21 N21 1.176(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C131 P1 C121 107.60(15) . . ?
C131 P1 C141 112.23(15) . . ?
C121 P1 C141 109.23(15) . . ?
C131 P1 C1 106.03(15) . . ?
C121 P1 C1 111.80(15) . . ?
C141 P1 C1 109.93(14) . . ?
C111 C1 P1 113.9(2) . . ?
C111 C1 H1A 108.8 . . ?
P1 C1 H1A 108.8 . . ?
C111 C1 H1B 108.8 . . ?
P1 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C112 C111 C116 119.3(3) . . ?
C112 C111 C1 119.0(3) . . ?
C116 C111 C1 121.6(3) . . ?
C113 C112 C111 120.2(3) . . ?
C113 C112 H112 119.9 . . ?
C111 C112 H112 119.9 . . ?
C114 C113 C112 120.2(3) . . ?
C114 C113 H113 119.9 . . ?
C112 C113 H113 119.9 . . ?
C115 C114 C113 120.1(3) . . ?
C115 C114 H114 119.9 . . ?
C113 C114 H114 119.9 . . ?
C114 C115 C116 119.8(3) . . ?
C114 C115 H115 120.1 . . ?
C116 C115 H115 120.1 . . ?
C115 C116 C111 120.3(3) . . ?
C115 C116 H116 119.9 . . ?
C111 C116 H116 119.9 . . ?
C122 C121 C126 119.9(3) . . ?
C122 C121 P1 118.3(2) . . ?
C126 C121 P1 121.2(2) . . ?
C123 C122 C121 120.0(3) . . ?
C123 C122 H122 120.0 . . ?
C121 C122 H122 120.0 . . ?
C122 C123 C124 120.0(3) . . ?
C122 C123 H123 120.0 . . ?
C124 C123 H123 120.0 . . ?
C125 C124 C123 120.3(4) . . ?
C125 C124 H124 119.9 . . ?
C123 C124 H124 119.9 . . ?
C126 C125 C124 120.3(3) . . ?
C126 C125 H125 119.8 . . ?
C124 C125 H125 119.8 . . ?
C125 C126 C121 119.5(3) . . ?
C125 C126 H126 120.2 . . ?
C121 C126 H126 120.2 . . ?
C136 C131 C132 120.1(3) . . ?
C136 C131 P1 120.3(2) . . ?
C132 C131 P1 119.4(3) . . ?
C133 C132 C131 119.1(4) . . ?
C133 C132 H132 120.4 . . ?
C131 C132 H132 120.4 . . ?
C134 C133 C132 120.8(3) . . ?
C134 C133 H133 119.6 . . ?
C132 C133 H133 119.6 . . ?
C133 C134 C135 121.1(3) . . ?
C133 C134 H134 119.5 . . ?
C135 C134 H134 119.5 . . ?
C134 C135 C136 119.0(4) . . ?
C134 C135 H135 120.5 . . ?
C136 C135 H135 120.5 . . ?
C135 C136 C131 119.9(3) . . ?
C135 C136 H136 120.0 . . ?
C131 C136 H136 120.0 . . ?
C142 C141 C146 119.6(3) . . ?
C142 C141 P1 121.1(3) . . ?
C146 C141 P1 119.3(2) . . ?
C141 C142 C143 119.5(3) . . ?
C141 C142 H142 120.2 . . ?
C143 C142 H142 120.2 . . ?
C144 C143 C142 120.3(3) . . ?
C144 C143 H143 119.9 . . ?
C142 C143 H143 119.9 . . ?
C145 C144 C143 120.4(3) . . ?
C145 C144 H144 119.8 . . ?
C143 C144 H144 119.8 . . ?
C144 C145 C146 120.1(3) . . ?
C144 C145 H145 120.0 . . ?
C146 C145 H145 120.0 . . ?
C145 C146 C141 120.1(3) . . ?
C145 C146 H146 120.0 . . ?
C141 C146 H146 120.0 . . ?
C241 P2 C221 109.89(14) . . ?
C241 P2 C231 107.83(14) . . ?
C221 P2 C231 110.37(13) . . ?
C241 P2 C2 110.21(13) . . ?
C221 P2 C2 111.05(14) . . ?
C231 P2 C2 107.42(14) . . ?
C211 C2 P2 115.2(2) . . ?
C211 C2 H2A 108.5 . . ?
P2 C2 H2A 108.5 . . ?
C211 C2 H2B 108.5 . . ?
P2 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C216 C211 C212 119.8(3) . . ?
C216 C211 C2 119.1(3) . . ?
C212 C211 C2 121.0(3) . . ?
C211 C212 C213 119.5(3) . . ?
C211 C212 H212 120.2 . . ?
C213 C212 H212 120.2 . . ?
C214 C213 C212 120.3(3) . . ?
C214 C213 H213 119.9 . . ?
C212 C213 H213 119.9 . . ?
C213 C214 C215 120.1(3) . . ?
C213 C214 H214 119.9 . . ?
C215 C214 H214 119.9 . . ?
C214 C215 C216 120.0(3) . . ?
C214 C215 H215 120.0 . . ?
C216 C215 H215 120.0 . . ?
C211 C216 C215 120.3(3) . . ?
C211 C216 H216 119.9 . . ?
C215 C216 H216 119.9 . . ?
C222 C221 C226 119.8(3) . . ?
C222 C221 P2 119.7(2) . . ?
C226 C221 P2 120.5(2) . . ?
C223 C222 C221 119.9(3) . . ?
C223 C222 H222 120.0 . . ?
C221 C222 H222 120.0 . . ?
C224 C223 C222 120.3(3) . . ?
C224 C223 H223 119.9 . . ?
C222 C223 H223 119.9 . . ?
C223 C224 C225 120.0(3) . . ?
C223 C224 H224 120.0 . . ?
C225 C224 H224 120.0 . . ?
C226 C225 C224 120.3(3) . . ?
C226 C225 H225 119.8 . . ?
C224 C225 H225 119.8 . . ?
C225 C226 C221 119.7(3) . . ?
C225 C226 H226 120.1 . . ?
C221 C226 H226 120.1 . . ?
C236 C231 C232 120.0(3) . . ?
C236 C231 P2 118.9(2) . . ?
C232 C231 P2 121.1(2) . . ?
C233 C232 C231 119.5(3) . . ?
C233 C232 H232 120.2 . . ?
C231 C232 H232 120.2 . . ?
C234 C233 C232 119.9(3) . . ?
C234 C233 H233 120.0 . . ?
C232 C233 H233 120.0 . . ?
C235 C234 C233 121.0(3) . . ?
C235 C234 H234 119.5 . . ?
C233 C234 H234 119.5 . . ?
C234 C235 C236 119.6(3) . . ?
C234 C235 H235 120.2 . . ?
C236 C235 H235 120.2 . . ?
C235 C236 C231 120.0(3) . . ?
C235 C236 H236 120.0 . . ?
C231 C236 H236 120.0 . . ?
C246 C241 C242 119.6(3) . . ?
C246 C241 P2 122.3(2) . . ?
C242 C241 P2 118.0(2) . . ?
C243 C242 C241 119.4(3) . . ?
C243 C242 H242 120.3 . . ?
C241 C242 H242 120.3 . . ?
C242 C243 C244 121.0(3) . . ?
C242 C243 H243 119.5 . . ?
C244 C243 H243 119.5 . . ?
C245 C244 C243 119.6(3) . . ?
C245 C244 H244 120.2 . . ?
C243 C244 H244 120.2 . . ?
C244 C245 C246 120.5(3) . . ?
C244 C245 H245 119.7 . . ?
C246 C245 H245 119.7 . . ?
C241 C246 C245 119.8(3) . . ?
C241 C246 H246 120.1 . . ?
C245 C246 H246 120.1 . . ?
N11 C11 S1 179.2(3) . . ?
N21 C21 S2 177.7(3) . . ?

_refine_diff_density_max         1.287
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_080528b7
_database_code_depnum_ccdc_archive 'CCDC 1986139'
loop_
_audit_author_name
_audit_author_address
'Alexandre N. Sobolev'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2020-02-25 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          '203-206 C'
_chemical_formula_moiety         'C25 H22 P, B F4'
_chemical_formula_sum            'C25 H22 B F4 P'
_chemical_formula_weight         440.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   9.5047(2)
_cell_length_b                   21.5886(5)
_cell_length_c                   11.1289(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.748(3)
_cell_angle_gamma                90
_cell_volume                     2174.89(1)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14894
_cell_measurement_theta_min      2.8248
_cell_measurement_theta_max      32.1858

_exptl_crystal_description       blade
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur-S, Sapphire3 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0009
_diffrn_reflns_number            49312
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         32.258
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7373
_reflns_number_gt                6785
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0300P)²+7.1000P] 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         7373
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0786
_refine_ls_wR_factor_ref         0.1698
_refine_ls_wR_factor_gt          0.1660
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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 0.56883(6) 0.13987(3) 0.63979(6) 0.01720(12) Uani 1 1 d . . . . .
C1 C 0.4708(2) 0.06698(10) 0.6019(2) 0.0180(4) Uani 1 1 d . . . . .
H1A H 0.417167 0.066058 0.510468 0.022 Uiso 1 1 calc R U . . .
H1B H 0.543517 0.032729 0.620192 0.022 Uiso 1 1 calc R U . . .
C11 C 0.6669(2) 0.14133(11) 0.8043(2) 0.0194(4) Uani 1 1 d . . . . .
C12 C 0.8154(3) 0.12285(11) 0.8439(2) 0.0219(4) Uani 1 1 d . . . . .
H12 H 0.865824 0.115684 0.783438 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8884(3) 0.11509(12) 0.9710(2) 0.0246(5) Uani 1 1 d . . . . .
H13 H 0.989074 0.102736 0.997672 0.030 Uiso 1 1 calc R U . . .
C14 C 0.8155(3) 0.12522(12) 1.0598(2) 0.0266(5) Uani 1 1 d . . . . .
H14 H 0.866359 0.119807 1.146973 0.032 Uiso 1 1 calc R U . . .
C15 C 0.6678(3) 0.14332(12) 1.0215(2) 0.0269(5) Uani 1 1 d . . . . .
H15 H 0.618305 0.150358 1.082617 0.032 Uiso 1 1 calc R U . . .
C16 C 0.5929(3) 0.15110(11) 0.8943(2) 0.0234(5) Uani 1 1 d . . . . .
H16 H 0.491840 0.162992 0.868167 0.028 Uiso 1 1 calc R U . . .
C21 C 0.6974(2) 0.14687(10) 0.5510(2) 0.0183(4) Uani 1 1 d . . . . .
C22 C 0.7108(3) 0.10111(11) 0.4671(2) 0.0229(4) Uani 1 1 d . . . . .
H22 H 0.651787 0.064790 0.456056 0.028 Uiso 1 1 calc R U . . .
C23 C 0.8115(3) 0.10879(12) 0.3991(2) 0.0255(5) Uani 1 1 d . . . . .
H23 H 0.820689 0.077743 0.341510 0.031 Uiso 1 1 calc R U . . .
C24 C 0.8979(3) 0.16185(12) 0.4160(2) 0.0256(5) Uani 1 1 d . . . . .
H24 H 0.966459 0.166879 0.369975 0.031 Uiso 1 1 calc R U . . .
C25 C 0.8848(3) 0.20757(12) 0.4995(3) 0.0276(5) Uani 1 1 d . . . . .
H25 H 0.944123 0.243781 0.510407 0.033 Uiso 1 1 calc R U . . .
C26 C 0.7844(3) 0.20035(11) 0.5673(3) 0.0253(5) Uani 1 1 d . . . . .
H26 H 0.775093 0.231623 0.624490 0.030 Uiso 1 1 calc R U . . .
C31 C 0.4426(3) 0.20372(11) 0.5945(2) 0.0215(4) Uani 1 1 d . . . . .
C32 C 0.3426(3) 0.20253(12) 0.4725(3) 0.0267(5) Uani 1 1 d . . . . .
H32 H 0.336379 0.167046 0.420704 0.032 Uiso 1 1 calc R U . . .
C33 C 0.2522(3) 0.25361(14) 0.4274(3) 0.0342(6) Uani 1 1 d . . . . .
H33 H 0.183895 0.252994 0.344849 0.041 Uiso 1 1 calc R U . . .
C34 C 0.2622(3) 0.30533(14) 0.5036(4) 0.0397(7) Uani 1 1 d . . . . .
H34 H 0.201147 0.340256 0.472479 0.048 Uiso 1 1 calc R U . . .
C35 C 0.3600(4) 0.30651(13) 0.6241(3) 0.0387(7) Uani 1 1 d . . . . .
H35 H 0.364938 0.341993 0.675680 0.046 Uiso 1 1 calc R U . . .
C36 C 0.4520(3) 0.25585(12) 0.6707(3) 0.0297(5) Uani 1 1 d . . . . .
H36 H 0.520155 0.256872 0.753354 0.036 Uiso 1 1 calc R U . . .
C41 C 0.3619(2) 0.05617(10) 0.6745(2) 0.0178(4) Uani 1 1 d . . . . .
C42 C 0.2133(3) 0.07168(12) 0.6213(2) 0.0232(4) Uani 1 1 d . . . . .
H42 H 0.180598 0.089823 0.539691 0.028 Uiso 1 1 calc R U . . .
C43 C 0.1128(3) 0.06064(13) 0.6876(3) 0.0269(5) Uani 1 1 d . . . . .
H43 H 0.011490 0.070613 0.650292 0.032 Uiso 1 1 calc R U . . .
C44 C 0.1600(3) 0.03517(12) 0.8076(3) 0.0260(5) Uani 1 1 d . . . . .
H44 H 0.091464 0.028441 0.853084 0.031 Uiso 1 1 calc R U . . .
C45 C 0.3074(3) 0.01955(12) 0.8611(2) 0.0239(5) Uani 1 1 d . . . . .
H45 H 0.339869 0.002110 0.943376 0.029 Uiso 1 1 calc R U . . .
C46 C 0.4085(3) 0.02939(11) 0.7943(2) 0.0216(4) Uani 1 1 d . . . . .
H46 H 0.508994 0.017852 0.830569 0.026 Uiso 1 1 calc R U . . .
B1 B 0.2207(3) 0.05262(12) 0.2513(3) 0.0207(5) Uani 1 1 d . . . . .
F1 F 0.20196(19) 0.00124(8) 0.31879(17) 0.0361(4) Uani 1 1 d . . . . .
F2 F 0.37044(16) 0.07129(7) 0.29901(15) 0.0274(3) Uani 1 1 d . . . . .
F3 F 0.1902(2) 0.03882(9) 0.12451(16) 0.0391(4) Uani 1 1 d . . . . .
F4 F 0.13282(18) 0.10155(8) 0.26775(17) 0.0347(4) 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
P1 C11 1.784(2) . ?
P1 C31 1.796(2) . ?
P1 C21 1.797(2) . ?
P1 C1 1.812(2) . ?
C1 C41 1.513(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C11 C12 1.402(3) . ?
C11 C16 1.404(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.391(3) . ?
C21 C26 1.399(3) . ?
C22 C23 1.399(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.394(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.396(3) . ?
C31 C32 1.399(4) . ?
C32 C33 1.394(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.387(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.380(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.398(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.395(3) . ?
C41 C46 1.396(3) . ?
C42 C43 1.394(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.387(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.387(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.398(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
B1 F1 1.381(3) . ?
B1 F3 1.384(3) . ?
B1 F4 1.393(3) . ?
B1 F2 1.417(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
C11 P1 C31 111.72(11) . . ?
C11 P1 C21 109.46(10) . . ?
C31 P1 C21 106.80(10) . . ?
C11 P1 C1 108.95(11) . . ?
C31 P1 C1 110.43(11) . . ?
C21 P1 C1 109.44(10) . . ?
C41 C1 P1 113.40(15) . . ?
C41 C1 H1A 108.9 . . ?
P1 C1 H1A 108.9 . . ?
C41 C1 H1B 108.9 . . ?
P1 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C12 C11 C16 119.6(2) . . ?
C12 C11 P1 118.55(17) . . ?
C16 C11 P1 121.07(18) . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C22 C21 C26 120.1(2) . . ?
C22 C21 P1 121.74(17) . . ?
C26 C21 P1 118.14(17) . . ?
C21 C22 C23 119.8(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 119.9(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C25 C24 C23 120.5(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.0(2) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 119.8(2) . . ?
C25 C26 H26 120.1 . . ?
C21 C26 H26 120.1 . . ?
C36 C31 C32 120.2(2) . . ?
C36 C31 P1 122.3(2) . . ?
C32 C31 P1 117.16(19) . . ?
C33 C32 C31 119.8(3) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C34 C33 C32 119.8(3) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C35 C34 C33 120.6(3) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 120.4(3) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C31 C36 C35 119.2(3) . . ?
C31 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C42 C41 C46 119.3(2) . . ?
C42 C41 C1 120.4(2) . . ?
C46 C41 C1 120.3(2) . . ?
C43 C42 C41 120.2(2) . . ?
C43 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C44 C43 C42 120.3(2) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C43 C44 C45 119.9(2) . . ?
C43 C44 H44 120.1 . . ?
C45 C44 H44 120.1 . . ?
C44 C45 C46 120.2(2) . . ?
C44 C45 H45 119.9 . . ?
C46 C45 H45 119.9 . . ?
C41 C46 C45 120.1(2) . . ?
C41 C46 H46 120.0 . . ?
C45 C46 H46 120.0 . . ?
F1 B1 F3 111.1(2) . . ?
F1 B1 F4 110.8(2) . . ?
F3 B1 F4 110.5(2) . . ?
F1 B1 F2 107.8(2) . . ?
F3 B1 F2 108.5(2) . . ?
F4 B1 F2 108.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 P1 C1 C41 59.11(19) . . . . ?
C31 P1 C1 C41 -63.94(19) . . . . ?
C21 P1 C1 C41 178.76(16) . . . . ?
C31 P1 C11 C12 -143.03(18) . . . . ?
C21 P1 C11 C12 -24.9(2) . . . . ?
C1 P1 C11 C12 94.7(2) . . . . ?
C31 P1 C11 C16 47.0(2) . . . . ?
C21 P1 C11 C16 165.04(19) . . . . ?
C1 P1 C11 C16 -75.3(2) . . . . ?
C16 C11 C12 C13 -0.7(4) . . . . ?
P1 C11 C12 C13 -170.91(19) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C11 -0.7(4) . . . . ?
C12 C11 C16 C15 1.0(4) . . . . ?
P1 C11 C16 C15 170.88(19) . . . . ?
C11 P1 C21 C22 119.9(2) . . . . ?
C31 P1 C21 C22 -119.0(2) . . . . ?
C1 P1 C21 C22 0.6(2) . . . . ?
C11 P1 C21 C26 -60.6(2) . . . . ?
C31 P1 C21 C26 60.5(2) . . . . ?
C1 P1 C21 C26 -179.91(19) . . . . ?
C26 C21 C22 C23 -0.1(4) . . . . ?
P1 C21 C22 C23 179.4(2) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C23 C24 C25 C26 0.1(4) . . . . ?
C24 C25 C26 C21 0.1(4) . . . . ?
C22 C21 C26 C25 -0.1(4) . . . . ?
P1 C21 C26 C25 -179.6(2) . . . . ?
C11 P1 C31 C36 16.5(2) . . . . ?
C21 P1 C31 C36 -103.1(2) . . . . ?
C1 P1 C31 C36 138.0(2) . . . . ?
C11 P1 C31 C32 -170.18(18) . . . . ?
C21 P1 C31 C32 70.2(2) . . . . ?
C1 P1 C31 C32 -48.8(2) . . . . ?
C36 C31 C32 C33 -0.1(4) . . . . ?
P1 C31 C32 C33 -173.5(2) . . . . ?
C31 C32 C33 C34 0.2(4) . . . . ?
C32 C33 C34 C35 -0.6(4) . . . . ?
C33 C34 C35 C36 0.8(4) . . . . ?
C32 C31 C36 C35 0.3(4) . . . . ?
P1 C31 C36 C35 173.4(2) . . . . ?
C34 C35 C36 C31 -0.7(4) . . . . ?
P1 C1 C41 C42 95.2(2) . . . . ?
P1 C1 C41 C46 -86.1(2) . . . . ?
C46 C41 C42 C43 0.2(4) . . . . ?
C1 C41 C42 C43 178.9(2) . . . . ?
C41 C42 C43 C44 1.1(4) . . . . ?
C42 C43 C44 C45 -1.2(4) . . . . ?
C43 C44 C45 C46 0.0(4) . . . . ?
C42 C41 C46 C45 -1.4(4) . . . . ?
C1 C41 C46 C45 179.9(2) . . . . ?
C44 C45 C46 C41 1.3(4) . . . . ?

_refine_diff_density_max         0.677
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.070

