# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2389827'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2024-10-09 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_audit_creation_date             2023-08-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C34 H37 N2 P2), Cl, C H2 Cl2'
_chemical_formula_sum            'C18 H20.50 Cl3 N P'
_chemical_formula_weight         388.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.434(3)
_cell_length_b                   9.825(2)
_cell_length_c                   22.843(6)
_cell_angle_alpha                78.484(15)
_cell_angle_beta                 81.149(19)
_cell_angle_gamma                67.190(15)
_cell_volume                     1905.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3227
_cell_measurement_temperature    149.89
_cell_measurement_theta_max      26.10
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.849
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       blocks
_exptl_crystal_F_000             806
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1235
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            28713
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         0.913
_diffrn_ambient_temperature      149.89
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4423
_reflns_number_total             6719
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         6719
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0777P)²+0.0410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1702
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C40(H40A,H40B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), C31(H31), C34(H34), C38(H38), C39(H39)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C33(H33A,H33B,H33C), C35(H35A,H35B,
 H35C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.31238(12) 0.30155(10) 0.17660(5) 0.0168(3) Uani 1 1 d . . . . .
P2 P 0.56119(12) 0.18173(10) 0.30503(5) 0.0167(3) Uani 1 1 d . . . . .
N2 N 0.5268(4) 0.3572(3) 0.27657(15) 0.0205(8) Uani 1 1 d . . . . .
N3 N 0.2172(4) 0.3001(3) 0.12248(15) 0.0222(8) Uani 1 1 d . . . . .
C4 C 0.1670(5) 0.4047(4) 0.22819(19) 0.0198(9) Uani 1 1 d . . . . .
C5 C 0.3873(5) 0.0045(4) 0.19241(18) 0.0190(9) Uani 1 1 d . . . . .
H5 H 0.323236 0.033646 0.160343 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4565(5) 0.3744(4) 0.14085(18) 0.0198(9) Uani 1 1 d . . . . .
C7 C 0.5079(5) 0.0695(4) 0.26345(18) 0.0185(9) Uani 1 1 d . . . . .
C8 C 0.8624(5) 0.0327(4) 0.25758(19) 0.0242(10) Uani 1 1 d . . . . .
H8 H 0.816481 0.041672 0.222100 0.029 Uiso 1 1 calc R U . . .
C9 C 0.8378(5) 0.0741(4) 0.3596(2) 0.0257(10) Uani 1 1 d . . . . .
H9 H 0.776389 0.111539 0.394069 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5703(5) -0.0827(4) 0.28632(18) 0.0210(9) Uani 1 1 d . . . . .
H10 H 0.633304 -0.114039 0.318855 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4128(4) 0.1142(4) 0.21499(17) 0.0162(9) Uani 1 1 d . . . . .
C12 C 0.7684(5) 0.0879(4) 0.30767(18) 0.0189(9) Uani 1 1 d . . . . .
C13 C 0.4196(5) 0.5281(4) 0.12122(19) 0.0249(10) Uani 1 1 d . . . . .
H13 H 0.319601 0.597870 0.130718 0.030 Uiso 1 1 calc R U . . .
C14 C 0.0799(5) 0.5559(4) 0.2109(2) 0.0256(10) Uani 1 1 d . . . . .
H14 H 0.100683 0.606225 0.172447 0.031 Uiso 1 1 calc R U . . .
C15 C 0.6521(5) 0.4060(4) 0.2455(2) 0.0263(10) Uani 1 1 d . . . . .
H15A H 0.696068 0.437121 0.274356 0.039 Uiso 1 1 calc R U . . .
H15B H 0.610885 0.490298 0.213787 0.039 Uiso 1 1 calc R U . . .
H15C H 0.732691 0.323134 0.227906 0.039 Uiso 1 1 calc R U . . .
C16 C 0.3920(5) 0.4838(4) 0.2981(2) 0.0245(10) Uani 1 1 d . . . . .
H16A H 0.314601 0.445795 0.320846 0.037 Uiso 1 1 calc R U . . .
H16B H 0.346659 0.556991 0.263558 0.037 Uiso 1 1 calc R U . . .
H16C H 0.426371 0.531563 0.323859 0.037 Uiso 1 1 calc R U . . .
C17 C 0.4659(5) 0.1716(4) 0.37880(18) 0.0197(9) Uani 1 1 d . . . . .
C18 C 0.1324(5) 0.3301(4) 0.28364(19) 0.0229(10) Uani 1 1 d . . . . .
H18 H 0.190031 0.226748 0.294704 0.027 Uiso 1 1 calc R U . . .
C19 C 0.6032(5) 0.2726(4) 0.12554(18) 0.0219(10) Uani 1 1 d . . . . .
H19 H 0.627965 0.168603 0.138576 0.026 Uiso 1 1 calc R U . . .
C20 C 0.3781(5) 0.0828(4) 0.39904(19) 0.0250(10) Uani 1 1 d . . . . .
H20 H 0.365849 0.024268 0.373133 0.030 Uiso 1 1 calc R U . . .
C21 C 0.7119(5) 0.3235(5) 0.0915(2) 0.0334(11) Uani 1 1 d . . . . .
H21 H 0.811033 0.254306 0.080498 0.040 Uiso 1 1 calc R U . . .
C22 C 0.5430(5) -0.1888(4) 0.26291(19) 0.0229(10) Uani 1 1 d . . . . .
H22 H 0.586366 -0.291309 0.279562 0.027 Uiso 1 1 calc R U . . .
C23 C 0.9971(5) 0.0051(5) 0.3603(2) 0.0356(12) Uani 1 1 d . . . . .
H23 H 1.043905 -0.005051 0.395670 0.043 Uiso 1 1 calc R U . . .
C24 C 0.4529(5) -0.1458(4) 0.21544(19) 0.0224(10) Uani 1 1 d . . . . .
H24 H 0.435870 -0.218586 0.198638 0.027 Uiso 1 1 calc R U . . .
C25 C 0.0137(5) 0.4068(5) 0.3229(2) 0.0305(11) Uani 1 1 d . . . . .
H25 H -0.010306 0.356080 0.360710 0.037 Uiso 1 1 calc R U . . .
C26 C 1.0881(5) -0.0486(5) 0.3106(2) 0.0327(11) Uani 1 1 d . . . . .
H26 H 1.196841 -0.095158 0.311686 0.039 Uiso 1 1 calc R U . . .
C27 C 1.0199(5) -0.0343(4) 0.2585(2) 0.0294(11) Uani 1 1 d . . . . .
H27 H 1.082017 -0.070713 0.223953 0.035 Uiso 1 1 calc R U . . .
C28 C 0.4839(5) 0.2577(4) 0.41728(19) 0.0271(11) Uani 1 1 d . . . . .
H28 H 0.541770 0.320052 0.403520 0.033 Uiso 1 1 calc R U . . .
C29 C 0.4165(5) 0.2507(5) 0.4754(2) 0.0325(12) Uani 1 1 d . . . . .
H29 H 0.431284 0.305643 0.502170 0.039 Uiso 1 1 calc R U . . .
C30 C -0.0375(5) 0.6313(5) 0.2507(2) 0.0334(12) Uani 1 1 d . . . . .
H30 H -0.096393 0.734330 0.239732 0.040 Uiso 1 1 calc R U . . .
C31 C 0.3087(5) 0.0802(5) 0.4571(2) 0.0354(12) Uani 1 1 d . . . . .
H31 H 0.247962 0.020549 0.470981 0.042 Uiso 1 1 calc R U . . .
C33 C 0.0630(5) 0.2927(5) 0.1338(2) 0.0303(11) Uani 1 1 d . . . . .
H33A H 0.023389 0.306534 0.175294 0.046 Uiso 1 1 calc R U . . .
H33B H 0.068833 0.195020 0.127226 0.046 Uiso 1 1 calc R U . . .
H33C H -0.006393 0.371651 0.106379 0.046 Uiso 1 1 calc R U . . .
C34 C 0.5319(5) 0.5760(5) 0.0877(2) 0.0333(11) Uani 1 1 d . . . . .
H34 H 0.508956 0.679724 0.074524 0.040 Uiso 1 1 calc R U . . .
C35 C 0.2944(6) 0.2581(5) 0.06428(19) 0.0336(11) Uani 1 1 d . . . . .
H35A H 0.228026 0.319770 0.032377 0.050 Uiso 1 1 calc R U . . .
H35B H 0.314278 0.152486 0.064253 0.050 Uiso 1 1 calc R U . . .
H35C H 0.392378 0.273885 0.057375 0.050 Uiso 1 1 calc R U . . .
C37 C -0.0693(5) 0.5572(5) 0.3065(2) 0.0315(11) Uani 1 1 d . . . . .
H37A H -0.057983 0.610201 0.336989 0.038 Uiso 1 1 calc R U . . .
H37B H -0.179556 0.570196 0.309647 0.038 Uiso 1 1 calc R U . . .
C38 C 0.3279(6) 0.1644(5) 0.4947(2) 0.0363(12) Uani 1 1 d . . . . .
H38 H 0.279487 0.162923 0.534392 0.044 Uiso 1 1 calc R U . . .
C39 C 0.6769(6) 0.4743(5) 0.0734(2) 0.0364(12) Uani 1 1 d . . . . .
H39 H 0.753054 0.508760 0.050789 0.044 Uiso 1 1 calc R U . . .
Cl1 Cl 0.17304(15) -0.08907(12) 0.10556(6) 0.0384(3) Uani 1 1 d . . . . .
Cl2 Cl 0.99549(15) 0.33208(13) -0.04097(6) 0.0396(3) Uani 1 1 d . . . . .
Cl4 Cl 1.2814(2) 0.12217(18) -0.08909(9) 0.0816(6) Uani 1 1 d . . . . .
C40 C 1.1071(5) 0.1401(5) -0.0434(2) 0.0332(11) Uani 1 1 d . . . . .
H40A H 1.130588 0.086882 -0.002365 0.040 Uiso 1 1 calc R U . . .
H40B H 1.047926 0.094501 -0.059915 0.040 Uiso 1 1 calc R U . . .
Cl5 Cl 0.41496(15) 0.41019(13) 0.60284(5) 0.0367(3) Uani 1 1 d . . . . .
Cl3 Cl 0.09197(17) 0.60533(14) 0.42932(6) 0.0517(4) Uani 1 1 d . . . . .
Cl6 Cl 0.11366(16) 0.78973(13) 0.51099(6) 0.0434(4) Uani 1 1 d . . . . .
C2 C 0.2071(6) 0.6212(5) 0.4795(2) 0.0409(13) Uani 1 1 d . . . . .
H2A H 0.307076 0.619929 0.458090 0.049 Uiso 1 1 calc R U . . .
H2B H 0.228338 0.534497 0.512103 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 N3 1.641(3) . ?
P1 C4 1.788(4) . ?
P1 C6 1.791(4) . ?
P1 C11 1.820(4) . ?
P2 N2 1.638(3) . ?
P2 C7 1.835(4) . ?
P2 C12 1.814(4) . ?
P2 C17 1.787(4) . ?
N2 C15 1.476(5) . ?
N2 C16 1.493(5) . ?
N3 C33 1.465(5) . ?
N3 C35 1.468(5) . ?
C4 C14 1.399(5) . ?
C4 C18 1.391(6) . ?
C5 H5 0.9500 . ?
C5 C11 1.395(5) . ?
C5 C24 1.386(5) . ?
C6 C13 1.404(5) . ?
C6 C19 1.398(6) . ?
C7 C10 1.398(5) . ?
C7 C11 1.424(6) . ?
C8 H8 0.9500 . ?
C8 C12 1.397(6) . ?
C8 C27 1.374(6) . ?
C9 H9 0.9500 . ?
C9 C12 1.399(6) . ?
C9 C23 1.390(6) . ?
C10 H10 0.9500 . ?
C10 C22 1.383(5) . ?
C13 H13 0.9500 . ?
C13 C34 1.387(6) . ?
C14 H14 0.9500 . ?
C14 C30 1.387(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C20 1.394(6) . ?
C17 C28 1.404(6) . ?
C18 H18 0.9500 . ?
C18 C25 1.390(6) . ?
C19 H19 0.9500 . ?
C19 C21 1.380(6) . ?
C20 H20 0.9500 . ?
C20 C31 1.386(6) . ?
C21 H21 0.9500 . ?
C21 C39 1.376(6) . ?
C22 H22 0.9500 . ?
C22 C24 1.378(6) . ?
C23 H23 0.9500 . ?
C23 C26 1.376(6) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C25 C37 1.382(6) . ?
C26 H26 0.9500 . ?
C26 C27 1.395(6) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.382(6) . ?
C29 H29 0.9500 . ?
C29 C38 1.377(7) . ?
C30 H30 0.9500 . ?
C30 C37 1.387(6) . ?
C31 H31 0.9500 . ?
C31 C38 1.380(7) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34 0.9500 . ?
C34 C39 1.382(7) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
Cl2 C40 1.776(4) . ?
Cl4 C40 1.773(5) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
Cl3 C2 1.762(5) . ?
Cl6 C2 1.785(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 P1 C4 104.62(19) . . ?
N3 P1 C6 105.76(18) . . ?
N3 P1 C11 112.07(17) . . ?
C4 P1 C6 118.44(18) . . ?
C4 P1 C11 108.81(18) . . ?
C6 P1 C11 107.18(18) . . ?
N2 P2 C7 117.83(17) . . ?
N2 P2 C12 107.62(18) . . ?
N2 P2 C17 109.23(17) . . ?
C12 P2 C7 104.04(18) . . ?
C17 P2 C7 107.50(19) . . ?
C17 P2 C12 110.43(19) . . ?
C15 N2 P2 121.0(3) . . ?
C15 N2 C16 111.9(3) . . ?
C16 N2 P2 123.3(3) . . ?
C33 N3 P1 122.1(3) . . ?
C33 N3 C35 112.9(3) . . ?
C35 N3 P1 122.3(3) . . ?
C14 C4 P1 120.2(3) . . ?
C18 C4 P1 119.2(3) . . ?
C18 C4 C14 120.3(4) . . ?
C11 C5 H5 119.1 . . ?
C24 C5 H5 119.1 . . ?
C24 C5 C11 121.9(4) . . ?
C13 C6 P1 121.5(3) . . ?
C19 C6 P1 118.0(3) . . ?
C19 C6 C13 120.0(4) . . ?
C10 C7 P2 111.4(3) . . ?
C10 C7 C11 118.2(3) . . ?
C11 C7 P2 130.4(3) . . ?
C12 C8 H8 119.3 . . ?
C27 C8 H8 119.3 . . ?
C27 C8 C12 121.5(4) . . ?
C12 C9 H9 120.2 . . ?
C23 C9 H9 120.2 . . ?
C23 C9 C12 119.6(4) . . ?
C7 C10 H10 119.1 . . ?
C22 C10 C7 121.8(4) . . ?
C22 C10 H10 119.1 . . ?
C5 C11 P1 112.5(3) . . ?
C5 C11 C7 118.6(3) . . ?
C7 C11 P1 128.9(3) . . ?
C8 C12 P2 121.0(3) . . ?
C8 C12 C9 118.6(4) . . ?
C9 C12 P2 120.3(3) . . ?
C6 C13 H13 120.6 . . ?
C34 C13 C6 118.8(4) . . ?
C34 C13 H13 120.6 . . ?
C4 C14 H14 120.5 . . ?
C30 C14 C4 119.0(4) . . ?
C30 C14 H14 120.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C20 C17 P2 123.2(3) . . ?
C20 C17 C28 119.9(4) . . ?
C28 C17 P2 116.8(3) . . ?
C4 C18 H18 120.0 . . ?
C25 C18 C4 120.0(4) . . ?
C25 C18 H18 120.0 . . ?
C6 C19 H19 120.0 . . ?
C21 C19 C6 119.9(4) . . ?
C21 C19 H19 120.0 . . ?
C17 C20 H20 120.1 . . ?
C31 C20 C17 119.7(4) . . ?
C31 C20 H20 120.1 . . ?
C19 C21 H21 120.0 . . ?
C39 C21 C19 120.1(4) . . ?
C39 C21 H21 120.0 . . ?
C10 C22 H22 120.0 . . ?
C24 C22 C10 120.0(4) . . ?
C24 C22 H22 120.0 . . ?
C9 C23 H23 119.5 . . ?
C26 C23 C9 121.1(4) . . ?
C26 C23 H23 119.5 . . ?
C5 C24 H24 120.3 . . ?
C22 C24 C5 119.5(4) . . ?
C22 C24 H24 120.3 . . ?
C18 C25 H25 120.2 . . ?
C37 C25 C18 119.6(4) . . ?
C37 C25 H25 120.2 . . ?
C23 C26 H26 120.1 . . ?
C23 C26 C27 119.7(4) . . ?
C27 C26 H26 120.1 . . ?
C8 C27 C26 119.6(4) . . ?
C8 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C17 C28 H28 120.4 . . ?
C29 C28 C17 119.3(4) . . ?
C29 C28 H28 120.4 . . ?
C28 C29 H29 119.8 . . ?
C38 C29 C28 120.4(4) . . ?
C38 C29 H29 119.8 . . ?
C14 C30 H30 119.8 . . ?
C37 C30 C14 120.5(4) . . ?
C37 C30 H30 119.8 . . ?
C20 C31 H31 120.0 . . ?
C38 C31 C20 119.9(5) . . ?
C38 C31 H31 120.0 . . ?
N3 C33 H33A 109.5 . . ?
N3 C33 H33B 109.5 . . ?
N3 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C13 C34 H34 119.7 . . ?
C39 C34 C13 120.6(4) . . ?
C39 C34 H34 119.7 . . ?
N3 C35 H35A 109.5 . . ?
N3 C35 H35B 109.5 . . ?
N3 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C25 C37 C30 120.5(4) . . ?
C25 C37 H37A 107.2 . . ?
C25 C37 H37B 107.2 . . ?
C30 C37 H37A 107.2 . . ?
C30 C37 H37B 107.2 . . ?
H37A C37 H37B 106.8 . . ?
C29 C38 C31 120.7(4) . . ?
C29 C38 H38 119.6 . . ?
C31 C38 H38 119.6 . . ?
C21 C39 C34 120.6(5) . . ?
C21 C39 H39 119.7 . . ?
C34 C39 H39 119.7 . . ?
Cl2 C40 H40A 109.7 . . ?
Cl2 C40 H40B 109.7 . . ?
Cl4 C40 Cl2 109.6(2) . . ?
Cl4 C40 H40A 109.7 . . ?
Cl4 C40 H40B 109.7 . . ?
H40A C40 H40B 108.2 . . ?
Cl3 C2 Cl6 111.1(3) . . ?
Cl3 C2 H2A 109.4 . . ?
Cl3 C2 H2B 109.4 . . ?
Cl6 C2 H2A 109.4 . . ?
Cl6 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C4 C14 C30 176.7(3) . . . . ?
P1 C4 C18 C25 -176.2(3) . . . . ?
P1 C6 C13 C34 -172.6(3) . . . . ?
P1 C6 C19 C21 172.0(3) . . . . ?
P2 C7 C10 C22 178.6(3) . . . . ?
P2 C7 C11 P1 1.0(6) . . . . ?
P2 C7 C11 C5 -178.1(3) . . . . ?
P2 C17 C20 C31 179.5(3) . . . . ?
P2 C17 C28 C29 -178.1(3) . . . . ?
N2 P2 C7 C10 168.4(3) . . . . ?
N2 P2 C7 C11 -13.8(5) . . . . ?
N2 P2 C12 C8 -84.3(3) . . . . ?
N2 P2 C12 C9 93.4(3) . . . . ?
N2 P2 C17 C20 133.2(3) . . . . ?
N2 P2 C17 C28 -47.4(4) . . . . ?
N3 P1 C4 C14 -64.4(4) . . . . ?
N3 P1 C4 C18 110.0(3) . . . . ?
N3 P1 C6 C13 77.6(4) . . . . ?
N3 P1 C6 C19 -93.8(3) . . . . ?
N3 P1 C11 C5 -1.5(4) . . . . ?
N3 P1 C11 C7 179.3(3) . . . . ?
C4 P1 N3 C33 -34.9(3) . . . . ?
C4 P1 N3 C35 165.2(3) . . . . ?
C4 P1 C6 C13 -39.2(4) . . . . ?
C4 P1 C6 C19 149.4(3) . . . . ?
C4 P1 C11 C5 113.7(3) . . . . ?
C4 P1 C11 C7 -65.5(4) . . . . ?
C4 C14 C30 C37 -1.0(7) . . . . ?
C4 C18 C25 C37 -0.1(6) . . . . ?
C6 P1 N3 C33 -160.7(3) . . . . ?
C6 P1 N3 C35 39.4(3) . . . . ?
C6 P1 C4 C14 53.0(4) . . . . ?
C6 P1 C4 C18 -132.6(3) . . . . ?
C6 P1 C11 C5 -117.1(3) . . . . ?
C6 P1 C11 C7 63.7(4) . . . . ?
C6 C13 C34 C39 0.7(7) . . . . ?
C6 C19 C21 C39 1.0(7) . . . . ?
C7 P2 N2 C15 -102.7(3) . . . . ?
C7 P2 N2 C16 101.1(3) . . . . ?
C7 P2 C12 C8 41.4(4) . . . . ?
C7 P2 C12 C9 -140.9(3) . . . . ?
C7 P2 C17 C20 4.3(4) . . . . ?
C7 P2 C17 C28 -176.3(3) . . . . ?
C7 C10 C22 C24 0.5(7) . . . . ?
C9 C23 C26 C27 -0.2(7) . . . . ?
C10 C7 C11 P1 178.7(3) . . . . ?
C10 C7 C11 C5 -0.4(6) . . . . ?
C10 C22 C24 C5 -1.5(6) . . . . ?
C11 P1 N3 C33 82.9(3) . . . . ?
C11 P1 N3 C35 -77.1(3) . . . . ?
C11 P1 C4 C14 175.7(3) . . . . ?
C11 P1 C4 C18 -9.9(4) . . . . ?
C11 P1 C6 C13 -162.6(3) . . . . ?
C11 P1 C6 C19 25.9(4) . . . . ?
C11 C5 C24 C22 1.6(6) . . . . ?
C11 C7 C10 C22 0.5(6) . . . . ?
C12 P2 N2 C15 14.4(4) . . . . ?
C12 P2 N2 C16 -141.8(3) . . . . ?
C12 P2 C7 C10 49.4(3) . . . . ?
C12 P2 C7 C11 -132.8(4) . . . . ?
C12 P2 C17 C20 -108.6(4) . . . . ?
C12 P2 C17 C28 70.8(3) . . . . ?
C12 C8 C27 C26 0.3(6) . . . . ?
C12 C9 C23 C26 0.6(7) . . . . ?
C13 C6 C19 C21 0.4(6) . . . . ?
C13 C34 C39 C21 0.7(7) . . . . ?
C14 C4 C18 C25 -1.8(6) . . . . ?
C14 C30 C37 C25 -1.0(7) . . . . ?
C17 P2 N2 C15 134.3(3) . . . . ?
C17 P2 N2 C16 -21.8(4) . . . . ?
C17 P2 C7 C10 -67.8(3) . . . . ?
C17 P2 C7 C11 110.1(4) . . . . ?
C17 P2 C12 C8 156.5(3) . . . . ?
C17 P2 C12 C9 -25.8(4) . . . . ?
C17 C20 C31 C38 -0.6(6) . . . . ?
C17 C28 C29 C38 -2.3(6) . . . . ?
C18 C4 C14 C30 2.4(6) . . . . ?
C18 C25 C37 C30 1.5(7) . . . . ?
C19 C6 C13 C34 -1.3(6) . . . . ?
C19 C21 C39 C34 -1.6(7) . . . . ?
C20 C17 C28 C29 1.3(6) . . . . ?
C20 C31 C38 C29 -0.5(7) . . . . ?
C23 C9 C12 P2 -178.4(3) . . . . ?
C23 C9 C12 C8 -0.6(6) . . . . ?
C23 C26 C27 C8 -0.3(7) . . . . ?
C24 C5 C11 P1 -179.8(3) . . . . ?
C24 C5 C11 C7 -0.6(6) . . . . ?
C27 C8 C12 P2 177.9(3) . . . . ?
C27 C8 C12 C9 0.1(6) . . . . ?
C28 C17 C20 C31 0.1(6) . . . . ?
C28 C29 C38 C31 1.9(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2389828'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2024-10-09 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_audit_creation_date             2023-08-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 N P2, Cl'
_chemical_formula_sum            'C30 H24 Cl N P2'
_chemical_formula_weight         495.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   16.6188(12)
_cell_length_b                   8.6367(5)
_cell_length_c                   18.7451(13)
_cell_angle_alpha                90
_cell_angle_beta                 111.367(4)
_cell_angle_gamma                90
_cell_volume                     2505.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9220
_cell_measurement_temperature    149.46
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            42597
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.405
_diffrn_ambient_temperature      149.46
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3638
_reflns_number_total             4414
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4414
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0302P)²+1.4918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0792
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.30112(3) 0.33701(5) 0.03149(3) 0.01837(12) Uani 1 1 d . . . . .
P2 P 0.17191(3) 0.36206(5) -0.10477(3) 0.01831(12) Uani 1 1 d . . . . .
Cl3 Cl -0.02386(3) 0.75996(6) -0.26877(3) 0.03071(13) Uani 1 1 d . . . . .
C2 C 0.17979(12) 0.3829(2) -0.19698(10) 0.0200(4) Uani 1 1 d . . . . .
C3 C 0.41446(11) 0.3339(2) 0.05055(10) 0.0206(4) Uani 1 1 d . . . . .
C4 C 0.28925(11) 0.6638(2) 0.06189(10) 0.0214(4) Uani 1 1 d . . . . .
H4 H 0.334737 0.655869 0.110416 0.026 Uiso 1 1 calc R U . . .
C5 C 0.28449(12) 0.2558(2) 0.11307(10) 0.0206(4) Uani 1 1 d . . . . .
C6 C 0.06562(11) 0.2947(2) -0.11764(10) 0.0200(4) Uani 1 1 d . . . . .
C7 C 0.15244(12) 0.6885(2) -0.08148(10) 0.0214(4) Uani 1 1 d . . . . .
H7 H 0.105944 0.696864 -0.129358 0.026 Uiso 1 1 calc R U . . .
C8 C 0.01663(12) 0.3639(2) -0.08005(11) 0.0292(5) Uani 1 1 d . . . . .
H8 H 0.036083 0.456780 -0.051915 0.035 Uiso 1 1 calc R U . . .
C9 C 0.25510(12) 0.3413(2) -0.20818(11) 0.0251(4) Uani 1 1 d . . . . .
H9 H 0.300751 0.292011 -0.168270 0.030 Uiso 1 1 calc R U . . .
C10 C 0.25967(11) 0.5338(2) 0.01578(10) 0.0183(4) Uani 1 1 d . . . . .
C11 C 0.03590(12) 0.1601(2) -0.15984(11) 0.0251(4) Uani 1 1 d . . . . .
H11 H 0.068514 0.113869 -0.186576 0.030 Uiso 1 1 calc R U . . .
C12 C 0.19184(11) 0.5466(2) -0.05546(10) 0.0183(4) Uani 1 1 d . . . . .
C13 C -0.04099(13) 0.0935(2) -0.16297(12) 0.0318(5) Uani 1 1 d . . . . .
H13 H -0.060972 0.000999 -0.191367 0.038 Uiso 1 1 calc R U . . .
C14 C 0.47159(12) 0.4027(2) 0.11688(11) 0.0272(4) Uani 1 1 d . . . . .
H14 H 0.451197 0.444280 0.154093 0.033 Uiso 1 1 calc R U . . .
C15 C 0.11257(12) 0.4551(2) -0.25564(10) 0.0242(4) Uani 1 1 d . . . . .
H15 H 0.060730 0.482393 -0.248327 0.029 Uiso 1 1 calc R U . . .
C16 C 0.19746(14) 0.4452(2) -0.33508(11) 0.0311(5) Uani 1 1 d . . . . .
H16 H 0.203723 0.467583 -0.382410 0.037 Uiso 1 1 calc R U . . .
C17 C -0.06043(13) 0.2973(3) -0.08365(12) 0.0350(5) Uani 1 1 d . . . . .
H17 H -0.093984 0.344426 -0.058030 0.042 Uiso 1 1 calc R U . . .
C18 C 0.34305(12) 0.1498(2) 0.16043(11) 0.0272(4) Uani 1 1 d . . . . .
H18 H 0.394717 0.125865 0.152095 0.033 Uiso 1 1 calc R U . . .
C19 C 0.44452(13) 0.2712(2) -0.00321(11) 0.0291(5) Uani 1 1 d . . . . .
H19 H 0.405409 0.222710 -0.047886 0.035 Uiso 1 1 calc R U . . .
C20 C 0.18312(12) 0.8178(2) -0.03536(11) 0.0254(4) Uani 1 1 d . . . . .
H20 H 0.157699 0.916135 -0.052178 0.031 Uiso 1 1 calc R U . . .
C21 C 0.19238(14) 0.2209(2) 0.18560(12) 0.0337(5) Uani 1 1 d . . . . .
H21 H 0.141083 0.245030 0.194559 0.040 Uiso 1 1 calc R U . . .
C22 C 0.26339(13) 0.3718(2) -0.27771(11) 0.0302(5) Uani 1 1 d . . . . .
H22 H 0.314426 0.342168 -0.285854 0.036 Uiso 1 1 calc R U . . .
C23 C 0.20875(13) 0.2903(2) 0.12546(11) 0.0289(5) Uani 1 1 d . . . . .
H23 H 0.168335 0.361341 0.092793 0.035 Uiso 1 1 calc R U . . .
C24 C 0.53173(13) 0.2793(3) 0.00835(13) 0.0365(5) Uani 1 1 d . . . . .
H24 H 0.552563 0.237290 -0.028484 0.044 Uiso 1 1 calc R U . . .
C25 C 0.25055(12) 0.8049(2) 0.03507(11) 0.0252(4) Uani 1 1 d . . . . .
H25 H 0.270510 0.894969 0.065471 0.030 Uiso 1 1 calc R U . . .
C26 C 0.12212(14) 0.4865(2) -0.32428(11) 0.0302(5) Uani 1 1 d . . . . .
H26 H 0.076942 0.536654 -0.364252 0.036 Uiso 1 1 calc R U . . .
C27 C 0.55858(13) 0.4097(2) 0.12781(13) 0.0352(5) Uani 1 1 d . . . . .
H27 H 0.598206 0.456657 0.172718 0.042 Uiso 1 1 calc R U . . .
C28 C 0.25096(15) 0.1167(2) 0.23226(12) 0.0353(5) Uani 1 1 d . . . . .
H28 H 0.239794 0.069940 0.273579 0.042 Uiso 1 1 calc R U . . .
C29 C 0.58783(13) 0.3487(3) 0.07356(13) 0.0382(6) Uani 1 1 d . . . . .
H29 H 0.647535 0.354675 0.081413 0.046 Uiso 1 1 calc R U . . .
C30 C -0.08857(13) 0.1620(2) -0.12458(12) 0.0344(5) Uani 1 1 d . . . . .
H30 H -0.141123 0.115768 -0.126326 0.041 Uiso 1 1 calc R U . . .
C31 C 0.32564(14) 0.0794(3) 0.21986(11) 0.0356(5) Uani 1 1 d . . . . .
H31 H 0.364893 0.005919 0.251817 0.043 Uiso 1 1 calc R U . . .
N1 N 0.24643(9) 0.25354(17) -0.04823(8) 0.0215(3) 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 P2 2.6806(7) . ?
P1 C3 1.7849(18) . ?
P1 C5 1.7929(18) . ?
P1 C10 1.8173(18) . ?
P1 N1 1.6092(15) . ?
P2 C2 1.7894(18) . ?
P2 C6 1.7905(18) . ?
P2 C12 1.8115(18) . ?
P2 N1 1.6059(15) . ?
C2 C9 1.390(3) . ?
C2 C15 1.397(3) . ?
C3 C14 1.393(3) . ?
C3 C19 1.388(3) . ?
C4 H4 0.9500 . ?
C4 C10 1.393(2) . ?
C4 C25 1.384(3) . ?
C5 C18 1.394(3) . ?
C5 C23 1.393(3) . ?
C6 C8 1.391(3) . ?
C6 C11 1.392(3) . ?
C7 H7 0.9500 . ?
C7 C12 1.392(2) . ?
C7 C20 1.390(3) . ?
C8 H8 0.9500 . ?
C8 C17 1.383(3) . ?
C9 H9 0.9500 . ?
C9 C22 1.385(3) . ?
C10 C12 1.403(2) . ?
C11 H11 0.9500 . ?
C11 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C13 C30 1.381(3) . ?
C14 H14 0.9500 . ?
C14 C27 1.385(3) . ?
C15 H15 0.9500 . ?
C15 C26 1.380(3) . ?
C16 H16 0.9500 . ?
C16 C22 1.378(3) . ?
C16 C26 1.386(3) . ?
C17 H17 0.9500 . ?
C17 C30 1.382(3) . ?
C18 H18 0.9500 . ?
C18 C31 1.389(3) . ?
C19 H19 0.9500 . ?
C19 C24 1.387(3) . ?
C20 H20 0.9500 . ?
C20 C25 1.390(3) . ?
C21 H21 0.9500 . ?
C21 C23 1.389(3) . ?
C21 C28 1.379(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C24 C29 1.375(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C27 C29 1.382(3) . ?
C28 H28 0.9500 . ?
C28 C31 1.381(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?

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
C3 P1 P2 127.77(6) . . ?
C3 P1 C5 107.63(8) . . ?
C3 P1 C10 110.88(8) . . ?
C5 P1 P2 121.69(6) . . ?
C5 P1 C10 109.69(8) . . ?
C10 P1 P2 69.23(6) . . ?
N1 P1 P2 33.47(5) . . ?
N1 P1 C3 112.15(8) . . ?
N1 P1 C5 113.98(8) . . ?
N1 P1 C10 102.47(8) . . ?
C2 P2 P1 127.84(6) . . ?
C2 P2 C6 108.57(8) . . ?
C2 P2 C12 109.89(8) . . ?
C6 P2 P1 120.70(6) . . ?
C6 P2 C12 110.02(8) . . ?
C12 P2 P1 69.56(6) . . ?
N1 P2 P1 33.55(5) . . ?
N1 P2 C2 112.70(8) . . ?
N1 P2 C6 112.65(8) . . ?
N1 P2 C12 102.89(8) . . ?
C9 C2 P2 120.44(14) . . ?
C9 C2 C15 120.18(17) . . ?
C15 C2 P2 119.10(14) . . ?
C14 C3 P1 119.91(14) . . ?
C19 C3 P1 119.57(14) . . ?
C19 C3 C14 120.41(17) . . ?
C10 C4 H4 120.9 . . ?
C25 C4 H4 120.9 . . ?
C25 C4 C10 118.16(17) . . ?
C18 C5 P1 120.75(14) . . ?
C23 C5 P1 119.21(14) . . ?
C23 C5 C18 119.86(17) . . ?
C8 C6 P2 121.56(14) . . ?
C8 C6 C11 119.64(17) . . ?
C11 C6 P2 118.44(14) . . ?
C12 C7 H7 121.0 . . ?
C20 C7 H7 121.0 . . ?
C20 C7 C12 118.05(17) . . ?
C6 C8 H8 120.0 . . ?
C17 C8 C6 119.97(18) . . ?
C17 C8 H8 120.0 . . ?
C2 C9 H9 120.1 . . ?
C22 C9 C2 119.78(18) . . ?
C22 C9 H9 120.1 . . ?
C4 C10 P1 128.77(14) . . ?
C4 C10 C12 120.44(17) . . ?
C12 C10 P1 110.70(13) . . ?
C6 C11 H11 119.9 . . ?
C13 C11 C6 120.19(18) . . ?
C13 C11 H11 119.9 . . ?
C7 C12 P2 128.39(14) . . ?
C7 C12 C10 121.00(16) . . ?
C10 C12 P2 110.52(13) . . ?
C11 C13 H13 120.2 . . ?
C30 C13 C11 119.66(18) . . ?
C30 C13 H13 120.2 . . ?
C3 C14 H14 120.5 . . ?
C27 C14 C3 119.06(19) . . ?
C27 C14 H14 120.5 . . ?
C2 C15 H15 120.3 . . ?
C26 C15 C2 119.42(18) . . ?
C26 C15 H15 120.3 . . ?
C22 C16 H16 119.7 . . ?
C22 C16 C26 120.53(18) . . ?
C26 C16 H16 119.7 . . ?
C8 C17 H17 120.0 . . ?
C30 C17 C8 119.91(19) . . ?
C30 C17 H17 120.0 . . ?
C5 C18 H18 120.1 . . ?
C31 C18 C5 119.82(19) . . ?
C31 C18 H18 120.1 . . ?
C3 C19 H19 120.0 . . ?
C24 C19 C3 119.93(19) . . ?
C24 C19 H19 120.0 . . ?
C7 C20 H20 119.6 . . ?
C7 C20 C25 120.82(18) . . ?
C25 C20 H20 119.6 . . ?
C23 C21 H21 120.2 . . ?
C28 C21 H21 120.2 . . ?
C28 C21 C23 119.65(19) . . ?
C9 C22 H22 120.0 . . ?
C16 C22 C9 119.90(18) . . ?
C16 C22 H22 120.0 . . ?
C5 C23 H23 120.0 . . ?
C21 C23 C5 119.95(19) . . ?
C21 C23 H23 120.0 . . ?
C19 C24 H24 120.3 . . ?
C29 C24 C19 119.5(2) . . ?
C29 C24 H24 120.3 . . ?
C4 C25 C20 121.51(17) . . ?
C4 C25 H25 119.2 . . ?
C20 C25 H25 119.2 . . ?
C15 C26 C16 120.17(19) . . ?
C15 C26 H26 119.9 . . ?
C16 C26 H26 119.9 . . ?
C14 C27 H27 119.9 . . ?
C29 C27 C14 120.2(2) . . ?
C29 C27 H27 119.9 . . ?
C21 C28 H28 119.5 . . ?
C21 C28 C31 121.03(19) . . ?
C31 C28 H28 119.5 . . ?
C24 C29 C27 120.94(19) . . ?
C24 C29 H29 119.5 . . ?
C27 C29 H29 119.5 . . ?
C13 C30 C17 120.62(19) . . ?
C13 C30 H30 119.7 . . ?
C17 C30 H30 119.7 . . ?
C18 C31 H31 120.2 . . ?
C28 C31 C18 119.7(2) . . ?
C28 C31 H31 120.2 . . ?
P2 N1 P1 112.98(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 P2 C2 C9 19.79(18) . . . . ?
P1 P2 C2 C15 -154.16(12) . . . . ?
P1 P2 C6 C8 65.68(17) . . . . ?
P1 P2 C6 C11 -107.41(14) . . . . ?
P1 P2 C12 C7 176.72(18) . . . . ?
P1 P2 C12 C10 0.21(10) . . . . ?
P1 C3 C14 C27 -175.06(15) . . . . ?
P1 C3 C19 C24 174.90(15) . . . . ?
P1 C5 C18 C31 -175.11(15) . . . . ?
P1 C5 C23 C21 176.01(15) . . . . ?
P1 C10 C12 P2 -0.31(15) . . . . ?
P1 C10 C12 C7 -177.12(14) . . . . ?
P2 P1 C3 C14 144.75(12) . . . . ?
P2 P1 C3 C19 -31.33(18) . . . . ?
P2 P1 C5 C18 135.58(13) . . . . ?
P2 P1 C5 C23 -39.45(17) . . . . ?
P2 P1 C10 C4 -176.31(17) . . . . ?
P2 P1 C10 C12 0.21(10) . . . . ?
P2 C2 C9 C22 -173.80(14) . . . . ?
P2 C2 C15 C26 173.10(14) . . . . ?
P2 C6 C8 C17 -171.88(16) . . . . ?
P2 C6 C11 C13 171.76(15) . . . . ?
C2 P2 C6 C8 -132.14(16) . . . . ?
C2 P2 C6 C11 54.77(17) . . . . ?
C2 P2 C12 C7 52.58(18) . . . . ?
C2 P2 C12 C10 -123.94(13) . . . . ?
C2 P2 N1 P1 124.91(10) . . . . ?
C2 C9 C22 C16 0.9(3) . . . . ?
C2 C15 C26 C16 0.7(3) . . . . ?
C3 P1 C5 C18 -26.50(17) . . . . ?
C3 P1 C5 C23 158.47(15) . . . . ?
C3 P1 C10 C4 -52.50(18) . . . . ?
C3 P1 C10 C12 124.02(13) . . . . ?
C3 P1 N1 P2 -125.69(10) . . . . ?
C3 C14 C27 C29 -0.2(3) . . . . ?
C3 C19 C24 C29 0.5(3) . . . . ?
C4 C10 C12 P2 176.54(13) . . . . ?
C4 C10 C12 C7 -0.3(3) . . . . ?
C5 P1 C3 C14 -54.60(17) . . . . ?
C5 P1 C3 C19 129.33(15) . . . . ?
C5 P1 C10 C4 66.24(18) . . . . ?
C5 P1 C10 C12 -117.24(13) . . . . ?
C5 P1 N1 P2 111.70(10) . . . . ?
C5 C18 C31 C28 -1.0(3) . . . . ?
C6 P2 C2 C9 -140.75(15) . . . . ?
C6 P2 C2 C15 45.30(17) . . . . ?
C6 P2 C12 C7 -66.91(18) . . . . ?
C6 P2 C12 C10 116.58(13) . . . . ?
C6 P2 N1 P1 -111.82(10) . . . . ?
C6 C8 C17 C30 0.0(3) . . . . ?
C6 C11 C13 C30 0.6(3) . . . . ?
C7 C20 C25 C4 -0.2(3) . . . . ?
C8 C6 C11 C13 -1.5(3) . . . . ?
C8 C17 C30 C13 -0.9(3) . . . . ?
C9 C2 C15 C26 -0.9(3) . . . . ?
C10 P1 C3 C14 65.38(17) . . . . ?
C10 P1 C3 C19 -110.69(16) . . . . ?
C10 P1 C5 C18 -147.23(15) . . . . ?
C10 P1 C5 C23 37.74(17) . . . . ?
C10 P1 N1 P2 -6.73(11) . . . . ?
C10 C4 C25 C20 0.9(3) . . . . ?
C11 C6 C8 C17 1.1(3) . . . . ?
C11 C13 C30 C17 0.6(3) . . . . ?
C12 P2 C2 C9 98.88(16) . . . . ?
C12 P2 C2 C15 -75.07(16) . . . . ?
C12 P2 C6 C8 -11.85(19) . . . . ?
C12 P2 C6 C11 175.06(14) . . . . ?
C12 P2 N1 P1 6.60(11) . . . . ?
C12 C7 C20 C25 -0.7(3) . . . . ?
C14 C3 C19 C24 -1.2(3) . . . . ?
C14 C27 C29 C24 -0.4(3) . . . . ?
C15 C2 C9 C22 0.1(3) . . . . ?
C18 C5 C23 C21 0.9(3) . . . . ?
C19 C3 C14 C27 1.0(3) . . . . ?
C19 C24 C29 C27 0.3(3) . . . . ?
C20 C7 C12 P2 -175.23(14) . . . . ?
C20 C7 C12 C10 1.0(3) . . . . ?
C21 C28 C31 C18 1.3(3) . . . . ?
C22 C16 C26 C15 0.3(3) . . . . ?
C23 C5 C18 C31 -0.1(3) . . . . ?
C23 C21 C28 C31 -0.4(3) . . . . ?
C25 C4 C10 P1 175.56(14) . . . . ?
C25 C4 C10 C12 -0.7(3) . . . . ?
C26 C16 C22 C9 -1.1(3) . . . . ?
C28 C21 C23 C5 -0.7(3) . . . . ?
N1 P1 C3 C14 179.27(14) . . . . ?
N1 P1 C3 C19 3.19(18) . . . . ?
N1 P1 C5 C18 98.55(16) . . . . ?
N1 P1 C5 C23 -76.48(16) . . . . ?
N1 P1 C10 C4 -172.34(16) . . . . ?
N1 P1 C10 C12 4.17(14) . . . . ?
N1 P2 C2 C9 -15.23(18) . . . . ?
N1 P2 C2 C15 170.82(14) . . . . ?
N1 P2 C6 C8 102.31(17) . . . . ?
N1 P2 C6 C11 -70.78(16) . . . . ?
N1 P2 C12 C7 172.84(16) . . . . ?
N1 P2 C12 C10 -3.68(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2389829'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2024-10-09 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_audit_creation_date             2023-08-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Cl2 P2, 2(B Cl F3), C H2 Cl2'
_chemical_formula_sum            'C31 H26 B2 Cl6 F6 P2'
_chemical_formula_weight         808.78
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.0219(5)
_cell_length_b                   35.5977(17)
_cell_length_c                   11.0777(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.014(3)
_cell_angle_gamma                90
_cell_volume                     3513.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9372
_cell_measurement_temperature    150.01
_cell_measurement_theta_max      25.44
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            41734
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.144
_diffrn_ambient_temperature      150.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5066
_reflns_number_total             6187
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.205
_refine_diff_density_min         -1.148
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         6187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+10.1084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1525
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C23(H23), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37),
 C39(H39), C41(H41)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.07555(11) 0.08762(3) 0.54649(8) 0.0208(2) Uani 1 1 d . . . . .
P2 P 0.26499(11) 0.13361(3) 0.31284(8) 0.0208(2) Uani 1 1 d . . . . .
Cl1 Cl 0.13755(11) 0.04912(3) 0.43407(9) 0.0295(2) Uani 1 1 d . . . . .
Cl2 Cl 0.42187(10) 0.11442(3) 0.44457(8) 0.0282(2) Uani 1 1 d . . . . .
C8 C 0.0293(4) 0.13118(10) 0.4659(3) 0.0207(8) Uani 1 1 d . . . . .
C9 C 0.1060(4) 0.15000(10) 0.3793(3) 0.0216(8) Uani 1 1 d . . . . .
C10 C 0.3120(5) 0.06949(11) 0.1850(4) 0.0310(9) Uani 1 1 d . . . . .
H10 H 0.410152 0.068990 0.231017 0.037 Uiso 1 1 calc R U . . .
C11 C -0.0890(4) 0.06803(10) 0.5937(3) 0.0234(8) Uani 1 1 d . . . . .
C12 C 0.2210(4) 0.09335(10) 0.6725(3) 0.0223(8) Uani 1 1 d . . . . .
C13 C 0.3499(4) 0.17135(11) 0.2427(3) 0.0261(8) Uani 1 1 d . . . . .
C14 C 0.2769(4) 0.06117(11) 0.7368(4) 0.0283(9) Uani 1 1 d . . . . .
H14 H 0.238417 0.037041 0.712274 0.034 Uiso 1 1 calc R U . . .
C15 C 0.2104(4) 0.09729(11) 0.2051(3) 0.0233(8) Uani 1 1 d . . . . .
C16 C -0.0958(4) 0.14862(11) 0.5008(4) 0.0277(9) Uani 1 1 d . . . . .
H16 H -0.146099 0.136671 0.559532 0.033 Uiso 1 1 calc R U . . .
C17 C 0.0494(5) 0.18407(11) 0.3320(4) 0.0297(9) Uani 1 1 d . . . . .
H17 H 0.098765 0.196659 0.273935 0.036 Uiso 1 1 calc R U . . .
C18 C 0.2790(5) 0.12878(11) 0.7067(3) 0.0293(9) Uani 1 1 d . . . . .
H18 H 0.241910 0.150493 0.662039 0.035 Uiso 1 1 calc R U . . .
C19 C 0.0668(5) 0.09840(13) 0.1384(4) 0.0332(10) Uani 1 1 d . . . . .
H19 H -0.002193 0.117395 0.153115 0.040 Uiso 1 1 calc R U . . .
C20 C -0.1053(5) 0.06722(13) 0.7164(4) 0.0361(10) Uani 1 1 d . . . . .
H20 H -0.030184 0.077607 0.776837 0.043 Uiso 1 1 calc R U . . .
C21 C 0.4374(5) 0.19746(12) 0.3147(4) 0.0390(11) Uani 1 1 d . . . . .
H21 H 0.449902 0.195739 0.401328 0.047 Uiso 1 1 calc R U . . .
C22 C -0.3413(5) 0.03593(13) 0.6620(4) 0.0368(10) Uani 1 1 d . . . . .
H22 H -0.427224 0.024403 0.685814 0.044 Uiso 1 1 calc R U . . .
C23 C 0.2675(5) 0.04263(12) 0.0969(4) 0.0375(10) Uani 1 1 d . . . . .
H23 H 0.335205 0.023282 0.082701 0.045 Uiso 1 1 calc R U . . .
C25 C 0.4452(5) 0.10025(13) 0.8712(4) 0.0361(10) Uani 1 1 d . . . . .
H25 H 0.521870 0.102749 0.940028 0.043 Uiso 1 1 calc R U . . .
C27 C -0.1992(5) 0.05314(12) 0.5052(4) 0.0312(9) Uani 1 1 d . . . . .
H27 H -0.187738 0.053732 0.421455 0.037 Uiso 1 1 calc R U . . .
C28 C -0.2323(6) 0.05109(16) 0.7490(4) 0.0491(13) Uani 1 1 d . . . . .
H28 H -0.244624 0.050459 0.832612 0.059 Uiso 1 1 calc R U . . .
C29 C 0.0261(5) 0.07118(14) 0.0497(4) 0.0413(11) Uani 1 1 d . . . . .
H29 H -0.071530 0.071617 0.002808 0.050 Uiso 1 1 calc R U . . .
C30 C -0.3259(5) 0.03747(12) 0.5403(4) 0.0337(10) Uani 1 1 d . . . . .
H30 H -0.402914 0.027686 0.480104 0.040 Uiso 1 1 calc R U . . .
C31 C -0.1489(5) 0.18286(12) 0.4525(4) 0.0339(10) Uani 1 1 d . . . . .
H31 H -0.234123 0.194162 0.478150 0.041 Uiso 1 1 calc R U . . .
C32 C 0.3911(5) 0.13183(13) 0.8065(4) 0.0380(10) Uani 1 1 d . . . . .
H32 H 0.431293 0.155814 0.830806 0.046 Uiso 1 1 calc R U . . .
C33 C 0.3893(5) 0.06508(13) 0.8369(4) 0.0342(10) Uani 1 1 d . . . . .
H33 H 0.427806 0.043548 0.881922 0.041 Uiso 1 1 calc R U . . .
C34 C -0.0773(5) 0.20036(12) 0.3670(4) 0.0368(10) Uani 1 1 d . . . . .
H34 H -0.114401 0.223542 0.332019 0.044 Uiso 1 1 calc R U . . .
C35 C 0.1257(5) 0.04362(13) 0.0293(4) 0.0382(11) Uani 1 1 d . . . . .
H35 H 0.096670 0.025155 -0.031743 0.046 Uiso 1 1 calc R U . . .
C36 C 0.4846(6) 0.22843(14) 0.1338(5) 0.0555(15) Uani 1 1 d . . . . .
H36 H 0.531570 0.248139 0.096005 0.067 Uiso 1 1 calc R U . . .
C37 C 0.5062(6) 0.22597(13) 0.2594(5) 0.0493(13) Uani 1 1 d . . . . .
H37 H 0.567845 0.243745 0.307647 0.059 Uiso 1 1 calc R U . . .
C39 C 0.3969(7) 0.20310(15) 0.0623(5) 0.0597(16) Uani 1 1 d . . . . .
H39 H 0.382045 0.205577 -0.024120 0.072 Uiso 1 1 calc R U . . .
C41 C 0.3299(6) 0.17383(13) 0.1159(4) 0.0421(11) Uani 1 1 d . . . . .
H41 H 0.271085 0.155724 0.066830 0.051 Uiso 1 1 calc R U . . .
F51 F 0.6026(3) 0.02328(7) 0.2372(2) 0.0385(6) Uani 1 1 d . . . . .
F1 F 0.8476(3) 0.02554(7) 0.2148(2) 0.0401(6) Uani 1 1 d . . . . .
F6 F 0.6661(3) 0.03510(7) 0.0497(2) 0.0446(7) Uani 1 1 d . . . . .
B26 B 0.7051(5) 0.03983(12) 0.1729(4) 0.0262(9) Uani 1 1 d . . . . .
F7 F 0.5786(3) 0.18600(9) 0.6252(3) 0.0557(8) Uani 1 1 d . . . . .
F24 F 0.5862(4) 0.25013(9) 0.5955(3) 0.0733(10) Uani 1 1 d . . . . .
F38 F 0.5399(6) 0.22354(11) 0.7799(3) 0.1066(17) Uani 1 1 d . . . . .
B42 B 0.5186(9) 0.21954(17) 0.6541(6) 0.0578(17) Uani 1 1 d . . . . .
Cl66 Cl 0.00398(19) 0.16942(4) 0.84342(15) 0.0706(4) Uani 1 1 d . . . . .
Cl57 Cl -0.22535(17) 0.16306(5) 1.00212(17) 0.0743(5) Uani 1 1 d . . . . .
C40 C -0.1426(7) 0.19219(17) 0.9038(6) 0.0671(16) Uani 1 1 d . . . . .
H40A H -0.102247 0.214910 0.949005 0.081 Uiso 1 1 calc R U . . .
H40B H -0.220320 0.200346 0.835640 0.081 Uiso 1 1 calc R U . . .
Cl3 Cl 0.3220(2) 0.22125(5) 0.60869(19) 0.0858(5) Uani 1 1 d . . . . .
Cl4 Cl 0.70158(16) 0.09246(4) 0.20587(12) 0.0553(3) 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 Cl1 1.9901(13) . ?
P1 C8 1.805(4) . ?
P1 C11 1.791(4) . ?
P1 C12 1.771(4) . ?
P2 Cl2 1.9881(13) . ?
P2 C9 1.809(4) . ?
P2 C13 1.784(4) . ?
P2 C15 1.776(4) . ?
C8 C9 1.433(5) . ?
C8 C16 1.395(5) . ?
C9 C17 1.386(5) . ?
C10 H10 0.9500 . ?
C10 C15 1.390(5) . ?
C10 C23 1.381(6) . ?
C11 C20 1.391(5) . ?
C11 C27 1.387(5) . ?
C12 C14 1.401(5) . ?
C12 C18 1.395(5) . ?
C13 C21 1.388(6) . ?
C13 C41 1.390(6) . ?
C14 H14 0.9500 . ?
C14 C33 1.388(6) . ?
C15 C19 1.388(6) . ?
C16 H16 0.9500 . ?
C16 C31 1.386(6) . ?
C17 H17 0.9500 . ?
C17 C34 1.391(6) . ?
C18 H18 0.9500 . ?
C18 C32 1.381(6) . ?
C19 H19 0.9500 . ?
C19 C29 1.388(6) . ?
C20 H20 0.9500 . ?
C20 C28 1.379(6) . ?
C21 H21 0.9500 . ?
C21 C37 1.382(6) . ?
C22 H22 0.9500 . ?
C22 C28 1.375(6) . ?
C22 C30 1.379(6) . ?
C23 H23 0.9500 . ?
C23 C35 1.378(7) . ?
C25 H25 0.9500 . ?
C25 C32 1.380(6) . ?
C25 C33 1.380(6) . ?
C27 H27 0.9500 . ?
C27 C30 1.381(6) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C29 C35 1.373(7) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C31 C34 1.376(6) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C36 C37 1.377(8) . ?
C36 C39 1.367(8) . ?
C37 H37 0.9500 . ?
C39 H39 0.9500 . ?
C39 C41 1.384(7) . ?
C41 H41 0.9500 . ?
F51 B26 1.385(5) . ?
F1 B26 1.393(5) . ?
F6 B26 1.366(5) . ?
B26 Cl4 1.910(5) . ?
F7 B42 1.369(7) . ?
F24 B42 1.450(7) . ?
F38 B42 1.384(7) . ?
B42 Cl3 1.767(8) . ?
Cl66 C40 1.769(6) . ?
Cl57 C40 1.753(6) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 P1 Cl1 110.35(12) . . ?
C11 P1 Cl1 103.97(13) . . ?
C11 P1 C8 109.94(17) . . ?
C12 P1 Cl1 109.05(13) . . ?
C12 P1 C8 112.10(17) . . ?
C12 P1 C11 111.13(17) . . ?
C9 P2 Cl2 109.33(12) . . ?
C13 P2 Cl2 105.88(14) . . ?
C13 P2 C9 110.91(17) . . ?
C15 P2 Cl2 109.48(13) . . ?
C15 P2 C9 110.74(17) . . ?
C15 P2 C13 110.38(17) . . ?
C9 C8 P1 129.3(3) . . ?
C16 C8 P1 112.3(3) . . ?
C16 C8 C9 118.3(3) . . ?
C8 C9 P2 128.2(3) . . ?
C17 C9 P2 113.4(3) . . ?
C17 C9 C8 118.3(3) . . ?
C15 C10 H10 120.7 . . ?
C23 C10 H10 120.7 . . ?
C23 C10 C15 118.7(4) . . ?
C20 C11 P1 120.9(3) . . ?
C27 C11 P1 118.6(3) . . ?
C27 C11 C20 120.5(4) . . ?
C14 C12 P1 118.0(3) . . ?
C18 C12 P1 121.2(3) . . ?
C18 C12 C14 120.7(4) . . ?
C21 C13 P2 119.9(3) . . ?
C21 C13 C41 120.7(4) . . ?
C41 C13 P2 119.4(3) . . ?
C12 C14 H14 120.5 . . ?
C33 C14 C12 119.0(4) . . ?
C33 C14 H14 120.5 . . ?
C10 C15 P2 120.4(3) . . ?
C19 C15 P2 118.3(3) . . ?
C19 C15 C10 121.2(4) . . ?
C8 C16 H16 119.0 . . ?
C31 C16 C8 122.0(4) . . ?
C31 C16 H16 119.0 . . ?
C9 C17 H17 119.0 . . ?
C9 C17 C34 122.0(4) . . ?
C34 C17 H17 119.0 . . ?
C12 C18 H18 120.5 . . ?
C32 C18 C12 119.0(4) . . ?
C32 C18 H18 120.5 . . ?
C15 C19 H19 120.7 . . ?
C29 C19 C15 118.6(4) . . ?
C29 C19 H19 120.7 . . ?
C11 C20 H20 120.5 . . ?
C28 C20 C11 119.0(4) . . ?
C28 C20 H20 120.5 . . ?
C13 C21 H21 120.3 . . ?
C37 C21 C13 119.4(4) . . ?
C37 C21 H21 120.3 . . ?
C28 C22 H22 120.0 . . ?
C28 C22 C30 120.0(4) . . ?
C30 C22 H22 120.0 . . ?
C10 C23 H23 119.7 . . ?
C35 C23 C10 120.6(4) . . ?
C35 C23 H23 119.7 . . ?
C32 C25 H25 119.6 . . ?
C32 C25 C33 120.8(4) . . ?
C33 C25 H25 119.6 . . ?
C11 C27 H27 120.4 . . ?
C30 C27 C11 119.3(4) . . ?
C30 C27 H27 120.4 . . ?
C20 C28 H28 119.6 . . ?
C22 C28 C20 120.8(4) . . ?
C22 C28 H28 119.6 . . ?
C19 C29 H29 119.7 . . ?
C35 C29 C19 120.6(4) . . ?
C35 C29 H29 119.7 . . ?
C22 C30 C27 120.4(4) . . ?
C22 C30 H30 119.8 . . ?
C27 C30 H30 119.8 . . ?
C16 C31 H31 120.2 . . ?
C34 C31 C16 119.5(4) . . ?
C34 C31 H31 120.2 . . ?
C18 C32 H32 119.8 . . ?
C25 C32 C18 120.4(4) . . ?
C25 C32 H32 119.8 . . ?
C14 C33 H33 120.0 . . ?
C25 C33 C14 120.0(4) . . ?
C25 C33 H33 120.0 . . ?
C17 C34 H34 120.1 . . ?
C31 C34 C17 119.9(4) . . ?
C31 C34 H34 120.1 . . ?
C23 C35 H35 119.8 . . ?
C29 C35 C23 120.3(4) . . ?
C29 C35 H35 119.8 . . ?
C37 C36 H36 119.3 . . ?
C39 C36 H36 119.3 . . ?
C39 C36 C37 121.4(4) . . ?
C21 C37 H37 120.2 . . ?
C36 C37 C21 119.5(5) . . ?
C36 C37 H37 120.2 . . ?
C36 C39 H39 120.0 . . ?
C36 C39 C41 120.0(5) . . ?
C41 C39 H39 120.0 . . ?
C13 C41 H41 120.5 . . ?
C39 C41 C13 119.0(5) . . ?
C39 C41 H41 120.5 . . ?
F51 B26 F1 109.2(3) . . ?
F51 B26 Cl4 106.7(3) . . ?
F1 B26 Cl4 109.7(3) . . ?
F6 B26 F51 111.9(3) . . ?
F6 B26 F1 111.5(3) . . ?
F6 B26 Cl4 107.6(3) . . ?
F7 B42 F24 109.9(5) . . ?
F7 B42 F38 109.1(5) . . ?
F7 B42 Cl3 112.3(5) . . ?
F24 B42 Cl3 108.7(4) . . ?
F38 B42 F24 111.8(5) . . ?
F38 B42 Cl3 105.0(5) . . ?
Cl66 C40 H40A 109.1 . . ?
Cl66 C40 H40B 109.1 . . ?
Cl57 C40 Cl66 112.3(3) . . ?
Cl57 C40 H40A 109.1 . . ?
Cl57 C40 H40B 109.1 . . ?
H40A C40 H40B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C8 C9 P2 6.2(5) . . . . ?
P1 C8 C9 C17 -178.3(3) . . . . ?
P1 C8 C16 C31 178.5(3) . . . . ?
P1 C11 C20 C28 -178.5(4) . . . . ?
P1 C11 C27 C30 179.1(3) . . . . ?
P1 C12 C14 C33 -179.1(3) . . . . ?
P1 C12 C18 C32 179.2(3) . . . . ?
P2 C9 C17 C34 176.7(3) . . . . ?
P2 C13 C21 C37 178.2(4) . . . . ?
P2 C13 C41 C39 -179.6(4) . . . . ?
P2 C15 C19 C29 176.8(3) . . . . ?
Cl1 P1 C8 C9 -43.1(4) . . . . ?
Cl1 P1 C8 C16 140.3(3) . . . . ?
Cl1 P1 C11 C20 132.0(3) . . . . ?
Cl1 P1 C11 C27 -47.2(3) . . . . ?
Cl1 P1 C12 C14 -52.1(3) . . . . ?
Cl1 P1 C12 C18 127.6(3) . . . . ?
Cl2 P2 C9 C8 -48.3(4) . . . . ?
Cl2 P2 C9 C17 136.1(3) . . . . ?
Cl2 P2 C13 C21 -43.7(4) . . . . ?
Cl2 P2 C13 C41 135.1(3) . . . . ?
Cl2 P2 C15 C10 -29.6(3) . . . . ?
Cl2 P2 C15 C19 153.1(3) . . . . ?
C8 P1 C11 C20 -109.9(4) . . . . ?
C8 P1 C11 C27 71.0(3) . . . . ?
C8 P1 C12 C14 -174.6(3) . . . . ?
C8 P1 C12 C18 5.1(4) . . . . ?
C8 C9 C17 C34 0.6(6) . . . . ?
C8 C16 C31 C34 0.2(7) . . . . ?
C9 P2 C13 C21 74.8(4) . . . . ?
C9 P2 C13 C41 -106.4(4) . . . . ?
C9 P2 C15 C10 -150.3(3) . . . . ?
C9 P2 C15 C19 32.5(4) . . . . ?
C9 C8 C16 C31 1.4(6) . . . . ?
C9 C17 C34 C31 1.0(7) . . . . ?
C10 C15 C19 C29 -0.4(6) . . . . ?
C10 C23 C35 C29 -0.7(7) . . . . ?
C11 P1 C8 C9 -157.2(3) . . . . ?
C11 P1 C8 C16 26.2(3) . . . . ?
C11 P1 C12 C14 61.9(3) . . . . ?
C11 P1 C12 C18 -118.4(3) . . . . ?
C11 C20 C28 C22 0.1(8) . . . . ?
C11 C27 C30 C22 -1.3(6) . . . . ?
C12 P1 C8 C9 78.7(4) . . . . ?
C12 P1 C8 C16 -98.0(3) . . . . ?
C12 P1 C11 C20 14.8(4) . . . . ?
C12 P1 C11 C27 -164.3(3) . . . . ?
C12 C14 C33 C25 -0.5(6) . . . . ?
C12 C18 C32 C25 0.2(6) . . . . ?
C13 P2 C9 C8 -164.6(3) . . . . ?
C13 P2 C9 C17 19.7(3) . . . . ?
C13 P2 C15 C10 86.5(3) . . . . ?
C13 P2 C15 C19 -90.7(3) . . . . ?
C13 C21 C37 C36 1.2(7) . . . . ?
C14 C12 C18 C32 -1.0(6) . . . . ?
C15 P2 C9 C8 72.4(4) . . . . ?
C15 P2 C9 C17 -103.2(3) . . . . ?
C15 P2 C13 C21 -162.1(3) . . . . ?
C15 P2 C13 C41 16.7(4) . . . . ?
C15 C10 C23 C35 0.7(6) . . . . ?
C15 C19 C29 C35 0.4(7) . . . . ?
C16 C8 C9 P2 -177.3(3) . . . . ?
C16 C8 C9 C17 -1.8(5) . . . . ?
C16 C31 C34 C17 -1.5(7) . . . . ?
C18 C12 C14 C33 1.2(6) . . . . ?
C19 C29 C35 C23 0.1(7) . . . . ?
C20 C11 C27 C30 0.0(6) . . . . ?
C21 C13 C41 C39 -0.9(7) . . . . ?
C23 C10 C15 P2 -177.3(3) . . . . ?
C23 C10 C15 C19 -0.1(6) . . . . ?
C27 C11 C20 C28 0.6(7) . . . . ?
C28 C22 C30 C27 2.0(7) . . . . ?
C30 C22 C28 C20 -1.4(8) . . . . ?
C32 C25 C33 C14 -0.3(7) . . . . ?
C33 C25 C32 C18 0.5(7) . . . . ?
C36 C39 C41 C13 1.7(8) . . . . ?
C37 C36 C39 C41 -1.2(9) . . . . ?
C39 C36 C37 C21 -0.3(8) . . . . ?
C41 C13 C21 C37 -0.6(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 2389830'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2024-10-09 deposited with the CCDC.	2024-11-13 downloaded from the CCDC.
;
_audit_creation_date             2023-08-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C27 H27 N P2, 2(B C24 F20), [+ solvents]2[C5H12]'
_chemical_formula_sum            'C75 H27 B2 F40 N P2'
_chemical_formula_weight         1785.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.5651(11)
_cell_length_b                   21.2162(11)
_cell_length_c                   23.6425(16)
_cell_angle_alpha                90
_cell_angle_beta                 101.146(6)
_cell_angle_gamma                90
_cell_volume                     7660.3(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5930
_cell_measurement_temperature    149.99
_cell_measurement_theta_max      21.29
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       shard
_exptl_crystal_F_000             3536
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1777
_diffrn_reflns_av_unetI/netI     0.1247
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            47683
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.643
_diffrn_ambient_temperature      149.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3990
_reflns_number_total             6750
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         6750
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0840P)²+4.5544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1973
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H2A(0.5) H2B(0.5) H2C(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
3.b Aromatic/amide H refined with riding coordinates:
 C30(H30), C34(H34), C46(H46), C48(H48), C50(H50), C52(H52), C55(H55),
 C56(H56), C57(H57), C60(H60)
3.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.52902(7) 0.29079(5) 0.31092(5) 0.0310(3) Uani 1 1 d . . . . .
C17 C 0.6446(3) 0.29481(18) 0.3359(2) 0.0327(10) Uani 1 1 d . . . . .
N21 N 0.500000 0.3317(2) 0.250000 0.0313(12) Uani 1 2 d S T P . .
C26 C 0.4948(3) 0.21448(18) 0.28154(18) 0.0329(10) Uani 1 1 d . . . . .
H26A H 0.531429 0.181025 0.303276 0.039 Uiso 1 1 calc R U . . .
H26B H 0.432927 0.206647 0.284068 0.039 Uiso 1 1 calc R U . . .
C30 C 0.6990(3) 0.30786(18) 0.2962(2) 0.0366(11) Uani 1 1 d . . . . .
H30 H 0.674459 0.317988 0.257295 0.044 Uiso 1 1 calc R U . . .
C33 C 0.4713(3) 0.32035(19) 0.36257(19) 0.0342(10) Uani 1 1 d . . . . .
C34 C 0.3858(3) 0.29962(19) 0.36466(19) 0.0355(11) Uani 1 1 d . . . . .
H34 H 0.361837 0.264139 0.342607 0.043 Uiso 1 1 calc R U . . .
C46 C 0.7880(3) 0.3057(2) 0.3148(2) 0.0423(12) Uani 1 1 d . . . . .
H46 H 0.825414 0.314451 0.288444 0.051 Uiso 1 1 calc R U . . .
C48 C 0.3373(3) 0.3307(2) 0.3985(2) 0.0410(11) Uani 1 1 d . . . . .
H48 H 0.280180 0.316219 0.400354 0.049 Uiso 1 1 calc R U . . .
C50 C 0.8243(3) 0.2909(2) 0.3714(2) 0.0474(13) Uani 1 1 d . . . . .
H50 H 0.886154 0.289734 0.383634 0.057 Uiso 1 1 calc R U . . .
C52 C 0.3710(3) 0.3831(2) 0.4301(2) 0.0519(13) Uani 1 1 d . . . . .
H52 H 0.336662 0.404371 0.453254 0.062 Uiso 1 1 calc R U . . .
C55 C 0.4550(3) 0.4048(2) 0.4282(2) 0.0540(14) Uani 1 1 d . . . . .
H55 H 0.477621 0.441047 0.449591 0.065 Uiso 1 1 calc R U . . .
C56 C 0.5049(3) 0.3732(2) 0.3950(2) 0.0440(12) Uani 1 1 d . . . . .
H56 H 0.562464 0.387457 0.394107 0.053 Uiso 1 1 calc R U . . .
C57 C 0.7708(3) 0.2779(2) 0.4098(2) 0.0484(13) Uani 1 1 d . . . . .
H57 H 0.796024 0.267404 0.448501 0.058 Uiso 1 1 calc R U . . .
C60 C 0.6813(3) 0.2799(2) 0.3929(2) 0.0418(12) Uani 1 1 d . . . . .
H60 H 0.644797 0.271105 0.419855 0.050 Uiso 1 1 calc R U . . .
F1 F 0.43101(15) 0.10201(11) 0.35213(11) 0.0407(6) Uani 1 1 d . . . . .
F2 F 0.08114(16) 0.01012(11) 0.33456(12) 0.0485(7) Uani 1 1 d . . . . .
F3 F 0.22814(16) 0.14920(12) 0.47222(12) 0.0476(7) Uani 1 1 d . . . . .
F4 F 0.28788(16) 0.16306(11) 0.28499(11) 0.0434(7) Uani 1 1 d . . . . .
F5 F 0.22834(17) -0.05302(10) 0.31368(11) 0.0432(7) Uani 1 1 d . . . . .
F6 F 0.50975(17) 0.23597(12) 0.51063(13) 0.0578(8) Uani 1 1 d . . . . .
F7 F 0.40135(17) -0.10818(12) 0.47154(12) 0.0541(8) Uani 1 1 d . . . . .
F8 F 0.19321(17) 0.21804(11) 0.36434(13) 0.0522(8) Uani 1 1 d . . . . .
F9 F 0.54705(16) 0.17515(13) 0.41653(12) 0.0514(7) Uani 1 1 d . . . . .
F10 F 0.38180(16) -0.01429(11) 0.39604(11) 0.0432(7) Uani 1 1 d . . . . .
F11 F 0.11270(15) 0.03972(12) 0.44976(12) 0.0469(7) Uani 1 1 d . . . . .
F12 F 0.2401(2) -0.07680(13) 0.20648(12) 0.0661(9) Uani 1 1 d . . . . .
F13 F 0.3057(2) 0.13685(13) 0.17821(12) 0.0624(8) Uani 1 1 d . . . . .
F14 F 0.13398(18) -0.05351(13) 0.52443(13) 0.0586(8) Uani 1 1 d . . . . .
F15 F 0.34834(18) 0.22048(13) 0.53795(13) 0.0582(8) Uani 1 1 d . . . . .
F16 F 0.27638(19) -0.13080(13) 0.53668(13) 0.0629(8) Uani 1 1 d . . . . .
F18 F -0.07854(17) 0.05626(14) 0.30164(15) 0.0739(10) Uani 1 1 d . . . . .
C19 C 0.3210(3) 0.12383(18) 0.40754(19) 0.0317(10) Uani 1 1 d . . . . .
F20 F 0.0327(2) 0.26275(13) 0.33036(17) 0.0824(11) Uani 1 1 d . . . . .
C22 C 0.4682(3) 0.1681(2) 0.4315(2) 0.0375(11) Uani 1 1 d . . . . .
F23 F -0.10587(19) 0.18376(15) 0.29805(18) 0.0926(13) Uani 1 1 d . . . . .
F25 F 0.2800(2) 0.01711(15) 0.13588(13) 0.0760(10) Uani 1 1 d . . . . .
C27 C 0.2603(3) 0.05637(19) 0.30733(19) 0.0349(10) Uani 1 1 d . . . . .
C28 C 0.2456(3) 0.01743(18) 0.41676(19) 0.0315(10) Uani 1 1 d . . . . .
C29 C 0.2775(3) 0.10148(19) 0.2678(2) 0.0377(11) Uani 1 1 d . . . . .
C31 C 0.3177(3) -0.02240(19) 0.4271(2) 0.0352(10) Uani 1 1 d . . . . .
C32 C 0.2482(3) -0.00336(19) 0.2824(2) 0.0373(11) Uani 1 1 d . . . . .
C35 C 0.3298(3) -0.07144(19) 0.4658(2) 0.0368(11) Uani 1 1 d . . . . .
C36 C 0.1866(3) 0.0040(2) 0.4525(2) 0.0368(11) Uani 1 1 d . . . . .
C37 C 0.4045(3) 0.13124(19) 0.39780(19) 0.0331(10) Uani 1 1 d . . . . .
C38 C 0.2668(3) -0.0823(2) 0.4987(2) 0.0418(12) Uani 1 1 d . . . . .
C39 C 0.3680(3) 0.1916(2) 0.4918(2) 0.0424(12) Uani 1 1 d . . . . .
B40 B 0.2438(3) 0.0772(2) 0.3716(2) 0.0306(11) Uani 1 1 d . . . . .
C41 C 0.1955(3) -0.0444(2) 0.4921(2) 0.0399(11) Uani 1 1 d . . . . .
C42 C 0.1466(3) 0.11064(19) 0.3547(2) 0.0361(11) Uani 1 1 d . . . . .
C43 C 0.0726(3) 0.0745(2) 0.3358(2) 0.0441(12) Uani 1 1 d . . . . .
C44 C 0.3070(3) 0.1548(2) 0.4566(2) 0.0388(11) Uani 1 1 d . . . . .
C45 C 0.2857(3) 0.0898(2) 0.2126(2) 0.0442(12) Uani 1 1 d . . . . .
C47 C 0.4489(3) 0.1991(2) 0.4784(2) 0.0421(12) Uani 1 1 d . . . . .
C49 C 0.1279(3) 0.1746(2) 0.3501(2) 0.0468(13) Uani 1 1 d . . . . .
C51 C -0.0258(3) 0.1604(3) 0.3172(3) 0.0656(17) Uani 1 1 d . . . . .
C53 C 0.2540(3) -0.0171(2) 0.2262(2) 0.0468(12) Uani 1 1 d . . . . .
C54 C 0.2737(3) 0.0296(2) 0.1906(2) 0.0504(13) Uani 1 1 d . . . . .
C58 C 0.0449(3) 0.2000(2) 0.3328(3) 0.0595(16) Uani 1 1 d . . . . .
C59 C -0.0111(3) 0.0969(2) 0.3187(2) 0.0566(15) Uani 1 1 d . . . . .
C2 C 0.500000 0.4026(3) 0.250000 0.0401(16) Uiso 1 2 d S . P . .
H2A H 0.453852 0.417998 0.269400 0.060 Uiso 0.5 1 calc R U P A -1
H2B H 0.489190 0.417998 0.210173 0.060 Uiso 0.5 1 calc R U P A -1
H2C H 0.556958 0.417998 0.270427 0.060 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C17 1.784(4) . ?
P1 N21 1.667(3) . ?
P1 C26 1.801(4) . ?
P1 C33 1.765(4) . ?
C17 C30 1.408(6) . ?
C17 C60 1.395(6) . ?
N21 C2 1.505(7) . ?
C26 C26 1.531(8) 2_655 ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C30 H30 0.9500 . ?
C30 C46 1.372(6) . ?
C33 C34 1.411(6) . ?
C33 C56 1.402(6) . ?
C34 H34 0.9500 . ?
C34 C48 1.371(6) . ?
C46 H46 0.9500 . ?
C46 C50 1.383(7) . ?
C48 H48 0.9500 . ?
C48 C52 1.383(6) . ?
C50 H50 0.9500 . ?
C50 C57 1.374(7) . ?
C52 H52 0.9500 . ?
C52 C55 1.395(7) . ?
C55 H55 0.9500 . ?
C55 C56 1.380(6) . ?
C56 H56 0.9500 . ?
C57 H57 0.9500 . ?
C57 C60 1.373(6) . ?
C60 H60 0.9500 . ?
F1 C37 1.376(5) . ?
F2 C43 1.373(5) . ?
F3 C44 1.354(5) . ?
F4 C29 1.369(5) . ?
F5 C32 1.356(5) . ?
F6 C47 1.345(5) . ?
F7 C35 1.345(5) . ?
F8 C49 1.365(5) . ?
F9 C22 1.349(5) . ?
F10 C31 1.359(5) . ?
F11 C36 1.369(5) . ?
F12 C53 1.352(5) . ?
F13 C45 1.361(5) . ?
F14 C41 1.350(5) . ?
F15 C39 1.338(5) . ?
F16 C38 1.354(5) . ?
F18 C59 1.359(5) . ?
C19 C37 1.373(6) . ?
C19 B40 1.659(6) . ?
C19 C44 1.386(6) . ?
F20 C58 1.345(5) . ?
C22 C37 1.387(6) . ?
C22 C47 1.373(7) . ?
F23 C51 1.337(5) . ?
F25 C54 1.342(6) . ?
C27 C29 1.400(6) . ?
C27 C32 1.395(6) . ?
C27 B40 1.649(7) . ?
C28 C31 1.388(6) . ?
C28 C36 1.392(6) . ?
C28 B40 1.654(6) . ?
C29 C45 1.357(6) . ?
C31 C35 1.375(6) . ?
C32 C53 1.381(7) . ?
C35 C38 1.384(6) . ?
C36 C41 1.377(6) . ?
C38 C41 1.355(6) . ?
C39 C44 1.378(6) . ?
C39 C47 1.364(7) . ?
B40 C42 1.649(6) . ?
C42 C43 1.384(6) . ?
C42 C49 1.388(6) . ?
C43 C59 1.372(6) . ?
C45 C54 1.379(7) . ?
C49 C58 1.386(6) . ?
C51 C58 1.377(7) . ?
C51 C59 1.365(7) . ?
C53 C54 1.374(7) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 P1 C26 112.03(19) . . ?
N21 P1 C17 110.43(16) . . ?
N21 P1 C26 97.13(19) . . ?
N21 P1 C33 108.87(17) . . ?
C33 P1 C17 111.7(2) . . ?
C33 P1 C26 115.7(2) . . ?
C30 C17 P1 119.1(3) . . ?
C60 C17 P1 120.5(3) . . ?
C60 C17 C30 120.2(4) . . ?
P1 N21 P1 117.3(3) . 2_655 ?
C2 N21 P1 121.36(13) . 2_655 ?
C2 N21 P1 121.36(13) . . ?
P1 C26 H26A 110.3 . . ?
P1 C26 H26B 110.3 . . ?
C26 C26 P1 107.24(18) 2_655 . ?
C26 C26 H26A 110.3 2_655 . ?
C26 C26 H26B 110.3 2_655 . ?
H26A C26 H26B 108.5 . . ?
C17 C30 H30 120.7 . . ?
C46 C30 C17 118.7(5) . . ?
C46 C30 H30 120.7 . . ?
C34 C33 P1 121.5(3) . . ?
C56 C33 P1 118.5(3) . . ?
C56 C33 C34 119.0(4) . . ?
C33 C34 H34 120.0 . . ?
C48 C34 C33 120.0(4) . . ?
C48 C34 H34 120.0 . . ?
C30 C46 H46 119.5 . . ?
C30 C46 C50 121.1(5) . . ?
C50 C46 H46 119.5 . . ?
C34 C48 H48 119.7 . . ?
C34 C48 C52 120.5(4) . . ?
C52 C48 H48 119.7 . . ?
C46 C50 H50 120.1 . . ?
C57 C50 C46 119.9(4) . . ?
C57 C50 H50 120.1 . . ?
C48 C52 H52 119.7 . . ?
C48 C52 C55 120.5(5) . . ?
C55 C52 H52 119.7 . . ?
C52 C55 H55 120.3 . . ?
C56 C55 C52 119.5(4) . . ?
C56 C55 H55 120.3 . . ?
C33 C56 H56 119.7 . . ?
C55 C56 C33 120.5(4) . . ?
C55 C56 H56 119.7 . . ?
C50 C57 H57 119.6 . . ?
C60 C57 C50 120.9(5) . . ?
C60 C57 H57 119.6 . . ?
C17 C60 H60 120.3 . . ?
C57 C60 C17 119.4(5) . . ?
C57 C60 H60 120.3 . . ?
C37 C19 B40 126.7(4) . . ?
C37 C19 C44 113.1(4) . . ?
C44 C19 B40 119.8(4) . . ?
F9 C22 C37 119.9(4) . . ?
F9 C22 C47 120.7(4) . . ?
C47 C22 C37 119.4(4) . . ?
C29 C27 B40 121.1(4) . . ?
C32 C27 C29 111.5(4) . . ?
C32 C27 B40 126.8(4) . . ?
C31 C28 C36 112.0(4) . . ?
C31 C28 B40 119.5(4) . . ?
C36 C28 B40 128.2(4) . . ?
F4 C29 C27 118.7(4) . . ?
C45 C29 F4 115.6(4) . . ?
C45 C29 C27 125.7(4) . . ?
F10 C31 C28 118.8(4) . . ?
F10 C31 C35 115.8(4) . . ?
C35 C31 C28 125.4(4) . . ?
F5 C32 C27 120.2(4) . . ?
F5 C32 C53 115.1(4) . . ?
C53 C32 C27 124.8(4) . . ?
F7 C35 C31 120.7(4) . . ?
F7 C35 C38 120.6(4) . . ?
C31 C35 C38 118.7(4) . . ?
F11 C36 C28 120.3(4) . . ?
F11 C36 C41 114.7(4) . . ?
C41 C36 C28 125.0(4) . . ?
F1 C37 C22 114.5(4) . . ?
C19 C37 F1 121.2(4) . . ?
C19 C37 C22 124.3(4) . . ?
F16 C38 C35 120.0(4) . . ?
F16 C38 C41 120.7(4) . . ?
C41 C38 C35 119.3(4) . . ?
F15 C39 C44 120.8(4) . . ?
F15 C39 C47 120.1(4) . . ?
C47 C39 C44 119.0(4) . . ?
C27 B40 C19 113.9(4) . . ?
C27 B40 C28 113.8(3) . . ?
C27 B40 C42 101.1(3) . . ?
C28 B40 C19 101.9(3) . . ?
C42 B40 C19 113.9(3) . . ?
C42 B40 C28 112.7(4) . . ?
F14 C41 C36 120.2(4) . . ?
F14 C41 C38 120.2(4) . . ?
C38 C41 C36 119.6(4) . . ?
C43 C42 B40 120.4(4) . . ?
C43 C42 C49 111.6(4) . . ?
C49 C42 B40 127.5(4) . . ?
F2 C43 C42 118.7(4) . . ?
F2 C43 C59 115.4(4) . . ?
C59 C43 C42 125.9(4) . . ?
F3 C44 C19 118.9(4) . . ?
F3 C44 C39 116.1(4) . . ?
C39 C44 C19 125.0(4) . . ?
F13 C45 C54 118.9(4) . . ?
C29 C45 F13 121.0(4) . . ?
C29 C45 C54 120.1(4) . . ?
F6 C47 C22 119.7(4) . . ?
F6 C47 C39 121.2(4) . . ?
C39 C47 C22 119.1(4) . . ?
F8 C49 C42 120.4(4) . . ?
F8 C49 C58 114.7(4) . . ?
C58 C49 C42 124.9(4) . . ?
F23 C51 C58 120.7(5) . . ?
F23 C51 C59 121.0(5) . . ?
C59 C51 C58 118.2(4) . . ?
F12 C53 C32 119.7(4) . . ?
F12 C53 C54 120.2(4) . . ?
C54 C53 C32 120.1(4) . . ?
F25 C54 C45 121.1(5) . . ?
F25 C54 C53 121.0(4) . . ?
C53 C54 C45 117.8(5) . . ?
F20 C58 C49 120.9(5) . . ?
F20 C58 C51 119.5(4) . . ?
C51 C58 C49 119.6(4) . . ?
F18 C59 C43 120.2(4) . . ?
F18 C59 C51 120.2(4) . . ?
C51 C59 C43 119.6(4) . . ?
N21 C2 H2A 109.5 . . ?
N21 C2 H2B 109.5 . . ?
N21 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C17 C30 C46 -174.6(3) . . . . ?
P1 C17 C60 C57 174.3(3) . . . . ?
P1 C33 C34 C48 -169.1(3) . . . . ?
P1 C33 C56 C55 168.4(4) . . . . ?
C17 P1 N21 P1 106.66(16) . . . 2_655 ?
C17 P1 N21 C2 -73.34(16) . . . . ?
C17 P1 C26 C26 -84.9(4) . . . 2_655 ?
C17 P1 C33 C34 -153.3(3) . . . . ?
C17 P1 C33 C56 38.3(4) . . . . ?
C17 C30 C46 C50 0.1(6) . . . . ?
N21 P1 C17 C30 -23.6(4) . . . . ?
N21 P1 C17 C60 162.0(3) . . . . ?
N21 P1 C26 C26 30.6(4) . . . 2_655 ?
N21 P1 C33 C34 84.5(4) . . . . ?
N21 P1 C33 C56 -83.9(4) . . . . ?
C26 P1 C17 C30 83.5(4) . . . . ?
C26 P1 C17 C60 -90.9(4) . . . . ?
C26 P1 N21 P1 -10.08(14) . . . 2_655 ?
C26 P1 N21 C2 169.92(14) . . . . ?
C26 P1 C33 C34 -23.5(4) . . . . ?
C26 P1 C33 C56 168.0(3) . . . . ?
C30 C17 C60 C57 -0.1(6) . . . . ?
C30 C46 C50 C57 0.3(7) . . . . ?
C33 P1 C17 C30 -144.9(3) . . . . ?
C33 P1 C17 C60 40.7(4) . . . . ?
C33 P1 N21 P1 -130.39(16) . . . 2_655 ?
C33 P1 N21 C2 49.61(16) . . . . ?
C33 P1 C26 C26 145.5(3) . . . 2_655 ?
C33 C34 C48 C52 1.1(7) . . . . ?
C34 C33 C56 C55 -0.4(7) . . . . ?
C34 C48 C52 C55 -0.4(8) . . . . ?
C46 C50 C57 C60 -0.5(7) . . . . ?
C48 C52 C55 C56 -0.7(8) . . . . ?
C50 C57 C60 C17 0.5(7) . . . . ?
C52 C55 C56 C33 1.1(8) . . . . ?
C56 C33 C34 C48 -0.7(6) . . . . ?
C60 C17 C30 C46 -0.2(6) . . . . ?
F2 C43 C59 F18 -0.4(8) . . . . ?
F2 C43 C59 C51 -178.4(5) . . . . ?
F4 C29 C45 F13 1.9(6) . . . . ?
F4 C29 C45 C54 -178.0(4) . . . . ?
F5 C32 C53 F12 0.0(6) . . . . ?
F5 C32 C53 C54 179.9(4) . . . . ?
F7 C35 C38 F16 -0.8(7) . . . . ?
F7 C35 C38 C41 179.9(4) . . . . ?
F8 C49 C58 F20 0.6(8) . . . . ?
F8 C49 C58 C51 179.6(5) . . . . ?
F9 C22 C37 F1 3.0(5) . . . . ?
F9 C22 C37 C19 -176.4(4) . . . . ?
F9 C22 C47 F6 -1.4(6) . . . . ?
F9 C22 C47 C39 179.1(4) . . . . ?
F10 C31 C35 F7 0.0(6) . . . . ?
F10 C31 C35 C38 -179.9(4) . . . . ?
F11 C36 C41 F14 -0.1(6) . . . . ?
F11 C36 C41 C38 -179.3(4) . . . . ?
F12 C53 C54 F25 -0.4(8) . . . . ?
F12 C53 C54 C45 178.9(4) . . . . ?
F13 C45 C54 F25 -1.0(7) . . . . ?
F13 C45 C54 C53 179.6(4) . . . . ?
F15 C39 C44 F3 -1.2(6) . . . . ?
F15 C39 C44 C19 179.1(4) . . . . ?
F15 C39 C47 F6 -0.8(7) . . . . ?
F15 C39 C47 C22 178.8(4) . . . . ?
F16 C38 C41 F14 1.8(7) . . . . ?
F16 C38 C41 C36 -179.0(4) . . . . ?
C19 B40 C42 C43 -166.3(4) . . . . ?
C19 B40 C42 C49 22.3(7) . . . . ?
F23 C51 C58 F20 1.9(9) . . . . ?
F23 C51 C58 C49 -177.2(6) . . . . ?
F23 C51 C59 F18 -1.2(9) . . . . ?
F23 C51 C59 C43 176.8(5) . . . . ?
C27 C29 C45 F13 -177.5(4) . . . . ?
C27 C29 C45 C54 2.6(7) . . . . ?
C27 C32 C53 F12 -179.3(4) . . . . ?
C27 C32 C53 C54 0.6(8) . . . . ?
C27 B40 C42 C43 71.1(5) . . . . ?
C27 B40 C42 C49 -100.4(5) . . . . ?
C28 C31 C35 F7 178.5(4) . . . . ?
C28 C31 C35 C38 -1.5(7) . . . . ?
C28 C36 C41 F14 -179.6(4) . . . . ?
C28 C36 C41 C38 1.1(7) . . . . ?
C28 B40 C42 C43 -50.8(6) . . . . ?
C28 B40 C42 C49 137.7(5) . . . . ?
C29 C27 C32 F5 -178.0(4) . . . . ?
C29 C27 C32 C53 1.2(6) . . . . ?
C29 C27 B40 C19 -51.5(5) . . . . ?
C29 C27 B40 C28 -167.7(4) . . . . ?
C29 C27 B40 C42 71.2(5) . . . . ?
C29 C45 C54 F25 178.9(4) . . . . ?
C29 C45 C54 C53 -0.4(7) . . . . ?
C31 C28 C36 F11 178.0(4) . . . . ?
C31 C28 C36 C41 -2.5(6) . . . . ?
C31 C28 B40 C19 -68.8(5) . . . . ?
C31 C28 B40 C27 54.3(5) . . . . ?
C31 C28 B40 C42 168.7(4) . . . . ?
C31 C35 C38 F16 179.1(4) . . . . ?
C31 C35 C38 C41 -0.2(7) . . . . ?
C32 C27 C29 F4 177.8(4) . . . . ?
C32 C27 C29 C45 -2.8(6) . . . . ?
C32 C27 B40 C19 137.7(4) . . . . ?
C32 C27 B40 C28 21.4(6) . . . . ?
C32 C27 B40 C42 -99.7(5) . . . . ?
C32 C53 C54 F25 179.7(5) . . . . ?
C32 C53 C54 C45 -1.0(8) . . . . ?
C35 C38 C41 F14 -178.9(4) . . . . ?
C35 C38 C41 C36 0.3(7) . . . . ?
C36 C28 C31 F10 -178.9(4) . . . . ?
C36 C28 C31 C35 2.6(6) . . . . ?
C36 C28 B40 C19 103.6(5) . . . . ?
C36 C28 B40 C27 -133.3(4) . . . . ?
C36 C28 B40 C42 -18.9(6) . . . . ?
C37 C19 B40 C27 -20.2(6) . . . . ?
C37 C19 B40 C28 102.9(5) . . . . ?
C37 C19 B40 C42 -135.5(4) . . . . ?
C37 C19 C44 F3 -177.4(4) . . . . ?
C37 C19 C44 C39 2.2(6) . . . . ?
C37 C22 C47 F6 -178.7(4) . . . . ?
C37 C22 C47 C39 1.7(7) . . . . ?
B40 C19 C37 F1 4.7(6) . . . . ?
B40 C19 C37 C22 -175.9(4) . . . . ?
B40 C19 C44 F3 -3.8(6) . . . . ?
B40 C19 C44 C39 175.9(4) . . . . ?
B40 C27 C29 F4 5.6(6) . . . . ?
B40 C27 C29 C45 -175.0(4) . . . . ?
B40 C27 C32 F5 -6.4(6) . . . . ?
B40 C27 C32 C53 172.8(4) . . . . ?
B40 C28 C31 F10 -5.4(6) . . . . ?
B40 C28 C31 C35 176.2(4) . . . . ?
B40 C28 C36 F11 5.1(6) . . . . ?
B40 C28 C36 C41 -175.3(4) . . . . ?
B40 C42 C43 F2 3.7(7) . . . . ?
B40 C42 C43 C59 -177.6(5) . . . . ?
B40 C42 C49 F8 -5.1(8) . . . . ?
B40 C42 C49 C58 176.4(5) . . . . ?
C42 C43 C59 F18 -179.2(5) . . . . ?
C42 C43 C59 C51 2.8(9) . . . . ?
C42 C49 C58 F20 179.1(5) . . . . ?
C42 C49 C58 C51 -1.9(9) . . . . ?
C43 C42 C49 F8 -177.2(4) . . . . ?
C43 C42 C49 C58 4.4(8) . . . . ?
C44 C19 C37 F1 177.8(4) . . . . ?
C44 C19 C37 C22 -2.8(6) . . . . ?
C44 C19 B40 C27 167.2(4) . . . . ?
C44 C19 B40 C28 -69.8(4) . . . . ?
C44 C19 B40 C42 51.9(5) . . . . ?
C44 C39 C47 F6 178.1(4) . . . . ?
C44 C39 C47 C22 -2.3(7) . . . . ?
C47 C22 C37 F1 -179.6(4) . . . . ?
C47 C22 C37 C19 1.0(7) . . . . ?
C47 C39 C44 F3 179.9(4) . . . . ?
C47 C39 C44 C19 0.2(7) . . . . ?
C49 C42 C43 F2 176.4(4) . . . . ?
C49 C42 C43 C59 -4.9(8) . . . . ?
C58 C51 C59 F18 -177.7(5) . . . . ?
C58 C51 C59 C43 0.3(9) . . . . ?
C59 C51 C58 F20 178.3(6) . . . . ?
C59 C51 C58 C49 -0.7(9) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.056 0.152 0.067 21.3 1.3 '1 ?'
2 -0.056 0.152 0.433 21.3 1.3 '1 ?'
3 0.000 0.500 0.104 502.5 116.4 '4 C5H12'
4 0.056 0.848 0.567 21.3 1.3 '1 ?'
5 -0.056 0.848 0.933 21.3 1.3 '1 ?'
6 0.500 0.000 -0.703 502.5 116.4 '4 C5H12'
7 0.444 0.348 0.933 21.3 1.3 '1 ?'
8 0.444 0.652 0.433 21.3 1.3 '1 ?'
9 0.556 0.348 0.567 21.3 1.3 '1 ?'
10 0.556 0.652 0.067 21.3 1.3 '1 ?'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
