# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_1123-3b
_database_code_depnum_ccdc_archive 'CCDC 2278978'
_audit_update_record             
;
2023-07-03 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-12-19
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H22 N O2 P'
_chemical_formula_sum            'C28 H22 N O2 P'
_chemical_formula_weight         435.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   15.6642(18)
_cell_length_b                   9.2490(10)
_cell_length_c                   18.762(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.668(10)
_cell_angle_gamma                90
_cell_volume                     2709.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2294
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.6230
_cell_measurement_theta_min      2.7280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.068
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0717
_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       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12345
_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         2.178
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  24.00   1.00    8.00    --  -11.59 -99.00 -90.00   26
  2  ω     -9.00  86.00   1.00    8.00    --   11.74  37.00-150.00   95
  3  ω    -55.00  27.00   1.00    8.00    --   11.74 -57.00  60.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0391614000
_diffrn_orient_matrix_UB_12      0.0280360000
_diffrn_orient_matrix_UB_13      0.0159834000
_diffrn_orient_matrix_UB_21      -0.0176179000
_diffrn_orient_matrix_UB_22      0.0018168000
_diffrn_orient_matrix_UB_23      0.0336167000
_diffrn_orient_matrix_UB_31      0.0148735000
_diffrn_orient_matrix_UB_32      -0.0713959000
_diffrn_orient_matrix_UB_33      0.0071500000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2653
_reflns_number_total             4758
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4758
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0784
_refine_ls_restrained_S_all      1.090
_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)+(0.1124P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2080
_refine_ls_wR_factor_ref         0.2425
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 C20, C21
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C19, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C18, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C17, C18
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C20 \\sim C21: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C19 \\sim C20: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C18 \\sim C19: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C17 \\sim C18: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
4.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C9(H9), C15(H15), C14(H14), C22(H22), C24(H24), C28(H28),
 C18(H18), C25(H25), C21(H21), C26(H26), C20(H20), C19(H19), C2(H2), C27(H27),
 C6(H6), C3(H3), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.73783(7) 0.35350(11) 0.48684(6) 0.0619(3) Uani 1 1 d . . . . .
O2 O 0.70106(17) 0.3103(3) 0.41496(15) 0.0751(8) Uani 1 1 d . . . . .
O1 O 0.58718(19) 0.4291(3) 0.71496(16) 0.0788(8) Uani 1 1 d . . . . .
N1 N 0.55166(17) 0.5904(3) 0.62606(17) 0.0560(8) Uani 1 1 d . . . . .
C10 C 0.6628(2) 0.4454(4) 0.5407(2) 0.0557(9) Uani 1 1 d . . . . .
C11 C 0.6158(2) 0.5711(4) 0.5125(2) 0.0541(9) Uani 1 1 d . . . . .
C12 C 0.5605(2) 0.6411(4) 0.5568(2) 0.0534(9) Uani 1 1 d . . . . .
C8 C 0.5953(2) 0.4710(4) 0.6537(2) 0.0566(10) Uani 1 1 d . . . . .
C16 C 0.6227(3) 0.6241(4) 0.4438(2) 0.0644(10) Uani 1 1 d . . . . .
H16 H 0.658925 0.577570 0.414247 0.077 Uiso 1 1 calc R U . . .
C13 C 0.5149(2) 0.7625(4) 0.5312(2) 0.0657(11) Uani 1 1 d . . . . .
H13 H 0.478398 0.809921 0.560145 0.079 Uiso 1 1 calc R U . . .
C9 C 0.6517(2) 0.3997(4) 0.6066(2) 0.0597(10) Uani 1 1 d . . . . .
H9 H 0.681415 0.317911 0.623476 0.072 Uiso 1 1 calc R U . . .
C23 C 0.7739(3) 0.1994(4) 0.5389(2) 0.0664(11) Uani 1 1 d . . . . .
C17 C 0.8229(3) 0.4801(5) 0.4848(3) 0.0763(10) Uani 1 1 d . U . . .
C15 C 0.5777(3) 0.7428(4) 0.4184(2) 0.0719(11) Uani 1 1 d . . . . .
H15 H 0.582653 0.776827 0.372298 0.086 Uiso 1 1 calc R U . . .
C7 C 0.4958(3) 0.6646(5) 0.6730(2) 0.0730(12) Uani 1 1 d . . . . .
H7A H 0.486586 0.602248 0.713188 0.088 Uiso 1 1 calc R U . . .
H7B H 0.440692 0.681456 0.646899 0.088 Uiso 1 1 calc R U . . .
C14 C 0.5240(3) 0.8114(4) 0.4640(2) 0.0733(12) Uani 1 1 d . . . . .
H14 H 0.493650 0.893045 0.447823 0.088 Uiso 1 1 calc R U . . .
C22 C 0.8533(3) 0.5605(5) 0.5450(3) 0.0820(13) Uani 1 1 d . . . . .
H22 H 0.828993 0.546797 0.588038 0.098 Uiso 1 1 calc R U . . .
C24 C 0.8398(3) 0.2014(5) 0.5923(2) 0.0769(12) Uani 1 1 d . . . . .
H24 H 0.870087 0.286492 0.602112 0.092 Uiso 1 1 calc R U . . .
C1 C 0.5310(4) 0.8054(5) 0.7005(2) 0.0846(15) Uani 1 1 d . . . . .
C28 C 0.7304(3) 0.0713(5) 0.5238(3) 0.0871(14) Uani 1 1 d . . . . .
H28 H 0.686902 0.067406 0.487076 0.104 Uiso 1 1 calc R U . . .
C18 C 0.8593(3) 0.5057(5) 0.4216(3) 0.0855(9) Uani 1 1 d . U . . .
H18 H 0.840371 0.453394 0.381043 0.103 Uiso 1 1 calc R U . . .
C25 C 0.8615(3) 0.0771(6) 0.6315(3) 0.0902(14) Uani 1 1 d . . . . .
H25 H 0.906152 0.078191 0.667363 0.108 Uiso 1 1 calc R U . . .
C21 C 0.9181(3) 0.6588(5) 0.5415(3) 0.0945(11) Uani 1 1 d . U . . .
H21 H 0.939282 0.708663 0.582203 0.113 Uiso 1 1 calc R U . . .
C26 C 0.8155(4) -0.0471(6) 0.6162(3) 0.1068(18) Uani 1 1 d . . . . .
H26 H 0.828660 -0.129990 0.642930 0.128 Uiso 1 1 calc R U . . .
C20 C 0.9519(3) 0.6830(6) 0.4763(3) 0.0952(10) Uani 1 1 d . U . . .
H20 H 0.994713 0.752063 0.473547 0.114 Uiso 1 1 calc R U . . .
C19 C 0.9244(3) 0.6092(5) 0.4171(3) 0.0920(9) Uani 1 1 d . U . . .
H19 H 0.947932 0.626334 0.373970 0.110 Uiso 1 1 calc R U . . .
C2 C 0.6171(5) 0.8301(6) 0.7135(3) 0.1068(18) Uani 1 1 d . . . . .
H2 H 0.655566 0.756720 0.704909 0.128 Uiso 1 1 calc R U . . .
C27 C 0.7524(4) -0.0518(6) 0.5641(4) 0.1103(18) Uani 1 1 d . . . . .
H27 H 0.722830 -0.137782 0.554613 0.132 Uiso 1 1 calc R U . . .
C6 C 0.4771(5) 0.9174(8) 0.7143(3) 0.160(3) Uani 1 1 d . . . . .
H6 H 0.418538 0.904255 0.704163 0.192 Uiso 1 1 calc R U . . .
C3 C 0.6484(6) 0.9626(8) 0.7392(4) 0.161(3) Uani 1 1 d . . . . .
H3 H 0.706799 0.977728 0.749152 0.194 Uiso 1 1 calc R U . . .
C5 C 0.5057(11) 1.0494(15) 0.7425(7) 0.233(9) Uani 1 1 d . . . . .
H5 H 0.468566 1.121042 0.755921 0.279 Uiso 1 1 calc R U . . .
C4 C 0.5928(12) 1.0658(10) 0.7489(6) 0.226(8) Uani 1 1 d . . . . .
H4 H 0.614361 1.156914 0.761195 0.272 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 O2 1.478(3) . ?
P1 C10 1.821(4) . ?
P1 C23 1.794(4) . ?
P1 C17 1.777(5) . ?
O1 C8 1.229(4) . ?
N1 C12 1.400(5) . ?
N1 C8 1.378(5) . ?
N1 C7 1.461(5) . ?
C10 C11 1.453(5) . ?
C10 C9 1.333(5) . ?
C11 C12 1.406(5) . ?
C11 C16 1.392(5) . ?
C12 C13 1.394(5) . ?
C8 C9 1.457(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.369(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.357(5) . ?
C9 H9 0.9300 . ?
C23 C24 1.378(6) . ?
C23 C28 1.384(6) . ?
C17 C22 1.403(6) . ?
C17 C18 1.376(6) . ?
C15 H15 0.9300 . ?
C15 C14 1.400(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C1 1.490(7) . ?
C14 H14 0.9300 . ?
C22 H22 0.9300 . ?
C22 C21 1.368(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.392(6) . ?
C1 C2 1.370(7) . ?
C1 C6 1.374(7) . ?
C28 H28 0.9300 . ?
C28 C27 1.395(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.407(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.374(7) . ?
C21 H21 0.9300 . ?
C21 C20 1.390(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.333(7) . ?
C20 H20 0.9300 . ?
C20 C19 1.344(7) . ?
C19 H19 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.391(8) . ?
C27 H27 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.391(16) . ?
C3 H3 0.9300 . ?
C3 C4 1.314(13) . ?
C5 H5 0.9300 . ?
C5 C4 1.368(19) . ?
C4 H4 0.9300 . ?

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
O2 P1 C10 114.29(17) . . ?
O2 P1 C23 111.36(18) . . ?
O2 P1 C17 113.3(2) . . ?
C23 P1 C10 104.92(18) . . ?
C17 P1 C10 102.90(18) . . ?
C17 P1 C23 109.4(2) . . ?
C12 N1 C7 120.7(3) . . ?
C8 N1 C12 122.3(3) . . ?
C8 N1 C7 116.9(3) . . ?
C11 C10 P1 120.2(3) . . ?
C9 C10 P1 120.4(3) . . ?
C9 C10 C11 119.4(3) . . ?
C12 C11 C10 118.2(3) . . ?
C16 C11 C10 122.9(3) . . ?
C16 C11 C12 118.9(3) . . ?
N1 C12 C11 120.4(3) . . ?
C13 C12 N1 120.2(3) . . ?
C13 C12 C11 119.4(4) . . ?
O1 C8 N1 121.3(3) . . ?
O1 C8 C9 122.5(3) . . ?
N1 C8 C9 116.2(3) . . ?
C11 C16 H16 119.1 . . ?
C15 C16 C11 121.8(4) . . ?
C15 C16 H16 119.1 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 H13 120.1 . . ?
C10 C9 C8 123.4(3) . . ?
C10 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
C24 C23 P1 124.7(3) . . ?
C24 C23 C28 119.2(4) . . ?
C28 C23 P1 116.1(3) . . ?
C22 C17 P1 122.6(3) . . ?
C18 C17 P1 119.7(4) . . ?
C18 C17 C22 117.7(4) . . ?
C16 C15 H15 121.0 . . ?
C16 C15 C14 118.0(4) . . ?
C14 C15 H15 121.0 . . ?
N1 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
N1 C7 C1 113.4(3) . . ?
H7A C7 H7B 107.7 . . ?
C1 C7 H7A 108.9 . . ?
C1 C7 H7B 108.9 . . ?
C13 C14 C15 122.0(4) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C17 C22 H22 119.4 . . ?
C21 C22 C17 121.3(5) . . ?
C21 C22 H22 119.4 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.6(5) . . ?
C25 C24 H24 119.7 . . ?
C2 C1 C7 122.6(4) . . ?
C2 C1 C6 116.9(6) . . ?
C6 C1 C7 120.6(6) . . ?
C23 C28 H28 120.3 . . ?
C23 C28 C27 119.5(5) . . ?
C27 C28 H28 120.3 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.5(5) . . ?
C19 C18 H18 119.3 . . ?
C24 C25 H25 120.7 . . ?
C26 C25 C24 118.6(5) . . ?
C26 C25 H25 120.7 . . ?
C22 C21 H21 120.4 . . ?
C22 C21 C20 119.1(5) . . ?
C20 C21 H21 120.4 . . ?
C25 C26 H26 119.1 . . ?
C27 C26 C25 121.7(5) . . ?
C27 C26 H26 119.1 . . ?
C21 C20 H20 119.2 . . ?
C19 C20 C21 121.7(5) . . ?
C19 C20 H20 119.2 . . ?
C18 C19 H19 120.6 . . ?
C20 C19 C18 118.8(5) . . ?
C20 C19 H19 120.6 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.5(7) . . ?
C3 C2 H2 119.3 . . ?
C28 C27 H27 119.8 . . ?
C26 C27 C28 120.4(5) . . ?
C26 C27 H27 119.8 . . ?
C1 C6 H6 118.3 . . ?
C1 C6 C5 123.4(9) . . ?
C5 C6 H6 118.3 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.0(10) . . ?
C4 C3 H3 121.0 . . ?
C6 C5 H5 122.6 . . ?
C4 C5 C6 114.8(10) . . ?
C4 C5 H5 122.6 . . ?
C3 C4 C5 125.0(13) . . ?
C3 C4 H4 117.5 . . ?
C5 C4 H4 117.5 . . ?

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 C10 C11 C12 -178.2(3) . . . . ?
P1 C10 C11 C16 2.3(5) . . . . ?
P1 C10 C9 C8 177.6(3) . . . . ?
P1 C23 C24 C25 177.8(3) . . . . ?
P1 C23 C28 C27 -177.3(4) . . . . ?
P1 C17 C22 C21 -179.0(4) . . . . ?
P1 C17 C18 C19 177.4(3) . . . . ?
O2 P1 C10 C11 -53.3(3) . . . . ?
O2 P1 C10 C9 127.8(3) . . . . ?
O2 P1 C23 C24 151.4(3) . . . . ?
O2 P1 C23 C28 -29.5(4) . . . . ?
O2 P1 C17 C22 164.7(3) . . . . ?
O2 P1 C17 C18 -12.9(4) . . . . ?
O1 C8 C9 C10 -178.4(4) . . . . ?
N1 C12 C13 C14 179.8(4) . . . . ?
N1 C8 C9 C10 0.9(5) . . . . ?
N1 C7 C1 C2 -31.8(6) . . . . ?
N1 C7 C1 C6 148.3(4) . . . . ?
C10 P1 C23 C24 -84.5(4) . . . . ?
C10 P1 C23 C28 94.7(3) . . . . ?
C10 P1 C17 C22 40.8(4) . . . . ?
C10 P1 C17 C18 -136.8(3) . . . . ?
C10 C11 C12 N1 0.2(5) . . . . ?
C10 C11 C12 C13 179.6(3) . . . . ?
C10 C11 C16 C15 180.0(4) . . . . ?
C11 C10 C9 C8 -1.3(6) . . . . ?
C11 C12 C13 C14 0.3(6) . . . . ?
C11 C16 C15 C14 0.4(6) . . . . ?
C12 N1 C8 O1 179.4(3) . . . . ?
C12 N1 C8 C9 0.0(5) . . . . ?
C12 N1 C7 C1 -72.7(5) . . . . ?
C12 C11 C16 C15 0.5(6) . . . . ?
C12 C13 C14 C15 0.6(6) . . . . ?
C8 N1 C12 C11 -0.5(5) . . . . ?
C8 N1 C12 C13 -179.9(3) . . . . ?
C8 N1 C7 C1 106.4(4) . . . . ?
C16 C11 C12 N1 179.7(3) . . . . ?
C16 C11 C12 C13 -0.9(5) . . . . ?
C16 C15 C14 C13 -0.9(6) . . . . ?
C9 C10 C11 C12 0.7(5) . . . . ?
C9 C10 C11 C16 -178.8(4) . . . . ?
C23 P1 C10 C11 -175.6(3) . . . . ?
C23 P1 C10 C9 5.6(4) . . . . ?
C23 P1 C17 C22 -70.4(4) . . . . ?
C23 P1 C17 C18 112.0(4) . . . . ?
C23 C24 C25 C26 -0.4(7) . . . . ?
C23 C28 C27 C26 -0.9(9) . . . . ?
C17 P1 C10 C11 70.0(3) . . . . ?
C17 P1 C10 C9 -108.9(3) . . . . ?
C17 P1 C23 C24 25.3(4) . . . . ?
C17 P1 C23 C28 -155.5(3) . . . . ?
C17 C22 C21 C20 2.5(7) . . . . ?
C17 C18 C19 C20 0.8(7) . . . . ?
C7 N1 C12 C11 178.5(3) . . . . ?
C7 N1 C12 C13 -0.9(5) . . . . ?
C7 N1 C8 O1 0.3(5) . . . . ?
C7 N1 C8 C9 -179.1(3) . . . . ?
C7 C1 C2 C3 179.9(5) . . . . ?
C7 C1 C6 C5 177.6(8) . . . . ?
C22 C17 C18 C19 -0.3(6) . . . . ?
C22 C21 C20 C19 -2.1(7) . . . . ?
C24 C23 C28 C27 1.9(7) . . . . ?
C24 C25 C26 C27 1.4(8) . . . . ?
C1 C2 C3 C4 -1.9(10) . . . . ?
C1 C6 C5 C4 6.4(17) . . . . ?
C28 C23 C24 C25 -1.3(6) . . . . ?
C18 C17 C22 C21 -1.4(7) . . . . ?
C25 C26 C27 C28 -0.8(9) . . . . ?
C21 C20 C19 C18 0.4(7) . . . . ?
C2 C1 C6 C5 -2.4(10) . . . . ?
C2 C3 C4 C5 6.7(17) . . . . ?
C6 C1 C2 C3 -0.1(8) . . . . ?
C6 C5 C4 C3 -9(2) . . . . ?

_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 0.387 -0.186 0.887 667.7 237.9 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2019-12-18
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.368
_oxdiff_exptl_absorpt_empirical_full_min 0.531
####################################################################### 
# 
# 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_4488
_database_code_depnum_ccdc_archive 'CCDC 2278979'
_audit_update_record             
;
2023-07-03 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_audit_creation_date             2021-06-20
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H2 Cl2, 3(C23 H20 N O2 P)'
_chemical_formula_sum            'C70 H62 Cl2 N3 O6 P3'
_chemical_formula_weight         1205.03
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.6477(5)
_cell_length_b                   15.5381(8)
_cell_length_c                   20.6214(9)
_cell_angle_alpha                101.740(4)
_cell_angle_beta                 97.775(4)
_cell_angle_gamma                91.950(4)
_cell_volume                     2992.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5722
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.1460
_cell_measurement_theta_min      2.8870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_unetI/netI     0.0924
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21889
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.033
_diffrn_reflns_theta_min         2.212
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  33.00   1.00    1.00    --  -40.73  38.00 120.00   98
  2  ω    -68.00  32.00   1.00    1.00    --  -40.73  57.00 -30.00  100
  3  ω     23.00  93.00   1.00    1.00    --   40.73-125.00 150.00   70
  4  ω     28.00  71.00   1.00    1.00    --   40.73-125.00  30.00   43
  5  ω     32.00 137.00   1.00    1.00    --  108.20 -77.00  90.00  105
  6  ω     69.00 118.00   1.00    1.00    --  108.20-125.00 -30.00   49
  7  ω     84.00 109.00   1.00    1.00    --  108.20 -95.00 -60.00   25
  8  ω     74.00  99.00   1.00    1.00    --  108.20 -95.00-150.00   25
  9  ω     93.00 120.00   1.00    1.00    --  108.20-125.00-180.00   27
 10  ω     45.00 134.00   1.00    1.00    --  108.20 -45.00-180.00   89
 11  ω     97.00 178.00   1.00    1.00    --  108.20  45.00 -90.00   81
 12  ω    115.00 154.00   1.00    1.00    --  108.20 125.00-180.00   39
 13  ω    103.00 139.00   1.00    1.00    --  108.20 125.00 -90.00   36
 14  ω     94.00 121.00   1.00    1.00    --  108.20 125.00 -30.00   27
 15  ω     94.00 163.00   1.00    1.00    --  108.20 125.00  90.00   69
 16  ω     78.00 174.00   1.00    1.00    --  108.20  77.00 150.00   96
 17  ω     29.00 105.00   1.00    1.00    --  108.20 -95.00  30.00   76
 18  ω     80.00 178.00   1.00    1.00    --  108.20  61.00-150.00   98
 19  ω   -110.00 -18.00   1.00    1.00    --  -40.73 -57.00-180.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1540495000
_diffrn_orient_matrix_UB_12      -0.0192777000
_diffrn_orient_matrix_UB_13      0.0075034000
_diffrn_orient_matrix_UB_21      -0.0456615000
_diffrn_orient_matrix_UB_22      0.0680641000
_diffrn_orient_matrix_UB_23      -0.0422231000
_diffrn_orient_matrix_UB_31      -0.0161923000
_diffrn_orient_matrix_UB_32      -0.0727452000
_diffrn_orient_matrix_UB_33      -0.0640993000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8074
_reflns_number_total             11794
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.820
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     782
_refine_ls_number_reflns         11794
_refine_ls_number_restraints     59
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0825
_refine_ls_restrained_S_all      1.035
_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)+(0.1062P)²+4.0815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2108
_refine_ls_wR_factor_ref         0.2425
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C36, C37, C38, C33
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C37 \\sim C36 \\sim C38 \\sim C33: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004 within 2A
4. Rigid body (RIGU) restrains
 C33, C38, C37, C36, C35, C34
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(H36A)=Sof(C70)=Sof(H70)=Sof(C69)=Sof(H69)=1-FVAR(1)
 Sof(H36)=Sof(C37)=Sof(H37)=Sof(C38)=Sof(H38)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), C27(H27),
  C28(H28), C31(H31), C34(H34), C35(H35), C36(H36), C36(H36A), C37(H37),
 C38(H38), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44), C00S(H00S),
 C48(H48), C49(H49), C52(H52), C56(H56), C57(H57), C58(H58), C59(H59), C60(H60),
  C62(H62), C63(H63), C64(H64), C65(H65), C66(H66), C70(H70), C69(H69)
6.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C45(H45A,H45B,H45C), C46(H46A,H46B,
 H46C), C67(H67A,H67B,H67C), C68(H68A,H68B,H68C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.13025(14) 0.70341(10) 0.73830(7) 0.0563(4) Uani 1 1 d . . . . .
Cl2 Cl 0.18706(15) 0.78667(12) 0.62932(9) 0.0704(5) Uani 1 1 d . . . . .
C1S C 0.2468(5) 0.7133(3) 0.6799(3) 0.0464(12) Uani 1 1 d . . . . .
H1SA H 0.339188 0.734306 0.703912 0.056 Uiso 1 1 calc R U . . .
H1SB H 0.254483 0.655912 0.651933 0.056 Uiso 1 1 calc R U . . .
P1 P 0.24280(10) 0.42520(7) 0.57850(5) 0.0279(2) Uani 1 1 d . . . . .
O1 O 0.5734(3) 0.1897(2) 0.63350(16) 0.0367(7) Uani 1 1 d . . . . .
O2 O 0.2726(3) 0.5223(2) 0.59099(16) 0.0361(7) Uani 1 1 d . . . . .
N1 N 0.3797(3) 0.4151(2) 0.70379(17) 0.0292(7) Uani 1 1 d . . . . .
C1 C 0.4813(4) 0.3835(3) 0.7471(2) 0.0283(8) Uani 1 1 d . . . . .
C2 C 0.5510(4) 0.3082(3) 0.7240(2) 0.0278(8) Uani 1 1 d . . . . .
C3 C 0.6559(4) 0.2804(3) 0.7679(2) 0.0316(9) Uani 1 1 d . . . . .
H3 H 0.703661 0.231456 0.751738 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6905(5) 0.3221(3) 0.8333(2) 0.0349(10) Uani 1 1 d . . . . .
C5 C 0.6175(5) 0.3970(3) 0.8563(2) 0.0351(10) Uani 1 1 d . . . . .
H5 H 0.638729 0.426533 0.900737 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5159(5) 0.4274(3) 0.8147(2) 0.0353(10) Uani 1 1 d . . . . .
H6 H 0.469859 0.477041 0.831200 0.042 Uiso 1 1 calc R U . . .
C7 C 0.3556(4) 0.3739(3) 0.6377(2) 0.0274(8) Uani 1 1 d . . . . .
C8 C 0.4180(4) 0.2993(3) 0.6134(2) 0.0299(9) Uani 1 1 d . . . . .
H8 H 0.395634 0.273379 0.568144 0.036 Uiso 1 1 calc R U . . .
C9 C 0.5173(4) 0.2584(3) 0.6546(2) 0.0296(9) Uani 1 1 d . . . . .
C10 C 0.2753(4) 0.3733(3) 0.4965(2) 0.0308(9) Uani 1 1 d . . . . .
C11 C 0.1719(4) 0.3252(3) 0.4476(2) 0.0340(9) Uani 1 1 d . . . . .
H11 H 0.084701 0.311902 0.458906 0.041 Uiso 1 1 calc R U . . .
C12 C 0.1972(5) 0.2970(3) 0.3826(2) 0.0398(11) Uani 1 1 d . . . . .
H12 H 0.127771 0.263900 0.350752 0.048 Uiso 1 1 calc R U . . .
C13 C 0.3258(5) 0.3177(3) 0.3644(2) 0.0407(11) Uani 1 1 d . . . . .
H13 H 0.341261 0.300622 0.320174 0.049 Uiso 1 1 calc R U . . .
C14 C 0.4307(5) 0.3641(3) 0.4126(2) 0.0407(11) Uani 1 1 d . . . . .
H14 H 0.518177 0.376348 0.401200 0.049 Uiso 1 1 calc R U . . .
C15 C 0.4056(5) 0.3922(3) 0.4777(2) 0.0348(10) Uani 1 1 d . . . . .
H15 H 0.476129 0.424132 0.509581 0.042 Uiso 1 1 calc R U . . .
C16 C 0.0649(4) 0.3929(3) 0.5844(2) 0.0300(9) Uani 1 1 d . . . . .
C17 C 0.0283(5) 0.3093(3) 0.5949(2) 0.0344(9) Uani 1 1 d . . . . .
H17 H 0.096708 0.270404 0.602846 0.041 Uiso 1 1 calc R U . . .
C18 C -0.1131(5) 0.2859(3) 0.5933(2) 0.0422(11) Uani 1 1 d . . . . .
H18 H -0.139310 0.230233 0.599349 0.051 Uiso 1 1 calc R U . . .
C19 C -0.2140(5) 0.3434(4) 0.5828(3) 0.0541(14) Uani 1 1 d . . . . .
H19 H -0.307955 0.326419 0.581275 0.065 Uiso 1 1 calc R U . . .
C20 C -0.1761(5) 0.4283(4) 0.5743(3) 0.0561(15) Uani 1 1 d . . . . .
H20 H -0.244235 0.467945 0.568298 0.067 Uiso 1 1 calc R U . . .
C21 C -0.0360(5) 0.4521(4) 0.5751(3) 0.0434(12) Uani 1 1 d . . . . .
H21 H -0.009870 0.507933 0.569385 0.052 Uiso 1 1 calc R U . . .
C22 C 0.8032(5) 0.2908(3) 0.8796(2) 0.0411(11) Uani 1 1 d . . . . .
H22A H 0.762079 0.271297 0.914429 0.062 Uiso 1 1 calc R U . . .
H22B H 0.872001 0.338354 0.899179 0.062 Uiso 1 1 calc R U . . .
H22C H 0.847136 0.242943 0.854782 0.062 Uiso 1 1 calc R U . . .
C23 C 0.3058(5) 0.4915(3) 0.7318(2) 0.0341(10) Uani 1 1 d . . . . .
H23A H 0.367969 0.543499 0.741280 0.051 Uiso 1 1 calc R U . . .
H23B H 0.274455 0.482958 0.772459 0.051 Uiso 1 1 calc R U . . .
H23C H 0.226379 0.498245 0.700181 0.051 Uiso 1 1 calc R U . . .
P2 P 0.54484(11) 0.93793(7) 0.74843(6) 0.0310(3) Uani 1 1 d . . . . .
O3 O 0.1969(4) 1.1518(2) 0.67332(16) 0.0457(9) Uani 1 1 d . . . . .
O6 O 0.5159(3) 0.8418(2) 0.74170(17) 0.0402(8) Uani 1 1 d . . . . .
N2 N 0.4421(4) 0.9461(2) 0.61717(18) 0.0293(7) Uani 1 1 d . . . . .
C24 C 0.2691(4) 1.0469(3) 0.5860(2) 0.0283(8) Uani 1 1 d . . . . .
C25 C 0.1802(4) 1.0747(3) 0.5359(2) 0.0319(9) Uani 1 1 d . . . . .
H25 H 0.124470 1.121153 0.548342 0.038 Uiso 1 1 calc R U . . .
C26 C 0.1718(5) 1.0366(3) 0.4698(2) 0.0339(9) Uani 1 1 d . . . . .
C27 C 0.2558(5) 0.9656(3) 0.4524(2) 0.0355(10) Uani 1 1 d . . . . .
H27 H 0.250364 0.937464 0.407656 0.043 Uiso 1 1 calc R U . . .
C28 C 0.3457(5) 0.9368(3) 0.5001(2) 0.0339(9) Uani 1 1 d . . . . .
H28 H 0.401634 0.890560 0.487201 0.041 Uiso 1 1 calc R U . . .
C29 C 0.3534(4) 0.9767(3) 0.5677(2) 0.0276(8) Uani 1 1 d . . . . .
C30 C 0.4414(4) 0.9838(3) 0.6833(2) 0.0287(8) Uani 1 1 d . . . . .
C31 C 0.3625(4) 1.0524(3) 0.7024(2) 0.0309(9) Uani 1 1 d . . . . .
H31 H 0.367816 1.076540 0.747848 0.037 Uiso 1 1 calc R U . . .
C32 C 0.2709(4) 1.0898(3) 0.6560(2) 0.0321(9) Uani 1 1 d . . . . .
C33 C 0.5014(5) 0.9987(4) 0.8263(3) 0.0463(9) Uani 1 1 d . U . . .
C34 C 0.5688(6) 1.0764(5) 0.8620(3) 0.0621(15) Uani 1 1 d . . . . .
H34 H 0.641887 1.101272 0.845403 0.074 Uiso 1 1 calc R U . . .
C35 C 0.5307(7) 1.1190(5) 0.9226(3) 0.0686(16) Uani 1 1 d . . . . .
H35 H 0.576995 1.172013 0.945900 0.082 Uiso 1 1 calc R U . . .
C36 C 0.4257(7) 1.0822(5) 0.9470(3) 0.0675(12) Uani 1 1 d . U . . .
H36 H 0.411931 1.102187 0.991139 0.081 Uiso 0.606(17) 1 calc R U P A 1
H36A H 0.373944 1.115968 0.976441 0.081 Uiso 0.394(17) 1 calc R U P A 2
C37 C 0.3325(13) 1.0097(8) 0.9028(5) 0.0593(13) Uani 0.606(17) 1 d . U P A 1
H37 H 0.247196 0.992651 0.914182 0.071 Uiso 0.606(17) 1 calc R U P A 1
C38 C 0.3773(12) 0.9684(9) 0.8441(6) 0.0518(12) Uani 0.606(17) 1 d . U P A 1
H38 H 0.324498 0.920385 0.816389 0.062 Uiso 0.606(17) 1 calc R U P A 1
C39 C 0.7252(4) 0.9697(3) 0.7478(2) 0.0287(8) Uani 1 1 d . . . . .
C40 C 0.8268(4) 0.9152(3) 0.7672(2) 0.0337(9) Uani 1 1 d . . . . .
H40 H 0.800681 0.861731 0.777207 0.040 Uiso 1 1 calc R U . . .
C41 C 0.9688(5) 0.9410(3) 0.7718(2) 0.0392(11) Uani 1 1 d . . . . .
H41 H 1.037448 0.904808 0.784710 0.047 Uiso 1 1 calc R U . . .
C42 C 1.0064(5) 1.0210(3) 0.7568(2) 0.0390(11) Uani 1 1 d . . . . .
H42 H 1.100678 1.038640 0.760424 0.047 Uiso 1 1 calc R U . . .
C43 C 0.9061(5) 1.0742(3) 0.7367(2) 0.0410(11) Uani 1 1 d . . . . .
H43 H 0.933085 1.127458 0.726748 0.049 Uiso 1 1 calc R U . . .
C44 C 0.7642(5) 1.0493(3) 0.7310(2) 0.0324(9) Uani 1 1 d . . . . .
H44 H 0.696412 1.084956 0.716341 0.039 Uiso 1 1 calc R U . . .
C45 C 0.0740(5) 1.0684(4) 0.4170(2) 0.0422(11) Uani 1 1 d . . . . .
H45A H 0.128039 1.094156 0.389203 0.063 Uiso 1 1 calc R U . . .
H45B H 0.016801 1.111679 0.438410 0.063 Uiso 1 1 calc R U . . .
H45C H 0.015173 1.019541 0.390049 0.063 Uiso 1 1 calc R U . . .
C46 C 0.5259(5) 0.8712(3) 0.5959(2) 0.0354(10) Uani 1 1 d . . . . .
H46A H 0.464544 0.820148 0.575284 0.053 Uiso 1 1 calc R U . . .
H46B H 0.584704 0.859438 0.634097 0.053 Uiso 1 1 calc R U . . .
H46C H 0.583152 0.884854 0.564238 0.053 Uiso 1 1 calc R U . . .
P3 P 0.84504(11) 0.70136(7) 0.87604(6) 0.0309(3) Uani 1 1 d . . . . .
O4 O 1.1951(4) 0.5270(2) 0.99751(16) 0.0416(8) Uani 1 1 d . . . . .
O5 O 0.8549(4) 0.7306(2) 0.81239(16) 0.0423(8) Uani 1 1 d . . . . .
N3 N 0.9232(4) 0.5314(2) 0.82685(17) 0.0309(8) Uani 1 1 d . . . . .
C00S C 1.1914(4) 0.3881(3) 0.8851(2) 0.0304(9) Uani 1 1 d . . . . .
H00S H 1.254469 0.387473 0.923337 0.036 Uiso 1 1 calc R U . . .
C47 C 1.0076(4) 0.4609(3) 0.8279(2) 0.0289(9) Uani 1 1 d . . . . .
C48 C 1.0029(5) 0.3911(3) 0.7724(2) 0.0333(9) Uani 1 1 d . . . . .
H48 H 0.940163 0.390803 0.733879 0.040 Uiso 1 1 calc R U . . .
C49 C 1.0904(5) 0.3226(3) 0.7740(2) 0.0358(10) Uani 1 1 d . . . . .
H49 H 1.084983 0.277063 0.736562 0.043 Uiso 1 1 calc R U . . .
C50 C 1.1873(5) 0.3202(3) 0.8309(2) 0.0320(9) Uani 1 1 d . . . . .
C51 C 1.1039(4) 0.4589(3) 0.8855(2) 0.0285(8) Uani 1 1 d . . . . .
C52 C 1.0276(4) 0.6000(3) 0.9380(2) 0.0314(9) Uani 1 1 d . . . . .
H52 H 1.032785 0.647969 0.973729 0.038 Uiso 1 1 calc R U . . .
C53 C 1.1145(4) 0.5282(3) 0.9454(2) 0.0300(9) Uani 1 1 d . . . . .
C54 C 0.9390(4) 0.6011(3) 0.8816(2) 0.0277(8) Uani 1 1 d . . . . .
C55 C 0.6693(4) 0.6804(3) 0.8909(2) 0.0305(9) Uani 1 1 d . . . . .
C56 C 0.6394(5) 0.6263(3) 0.9346(2) 0.0320(9) Uani 1 1 d . . . . .
H56 H 0.709511 0.595371 0.953385 0.038 Uiso 1 1 calc R U . . .
C57 C 0.5029(5) 0.6193(3) 0.9496(2) 0.0403(11) Uani 1 1 d . . . . .
H57 H 0.481919 0.583643 0.978650 0.048 Uiso 1 1 calc R U . . .
C58 C 0.3998(5) 0.6649(4) 0.9216(3) 0.0488(13) Uani 1 1 d . . . . .
H58 H 0.309766 0.660834 0.932523 0.059 Uiso 1 1 calc R U . . .
C59 C 0.4283(5) 0.7170(4) 0.8774(3) 0.0497(13) Uani 1 1 d . . . . .
H59 H 0.357069 0.746710 0.858156 0.060 Uiso 1 1 calc R U . . .
C60 C 0.5631(5) 0.7248(3) 0.8616(2) 0.0392(10) Uani 1 1 d . . . . .
H60 H 0.582267 0.759501 0.831690 0.047 Uiso 1 1 calc R U . . .
C61 C 0.9263(4) 0.7825(3) 0.9480(2) 0.0334(9) Uani 1 1 d . . . . .
C62 C 0.8819(6) 0.7950(4) 1.0101(3) 0.0496(13) Uani 1 1 d . . . . .
H62 H 0.806102 0.760380 1.016197 0.060 Uiso 1 1 calc R U . . .
C63 C 0.9493(6) 0.8589(4) 1.0638(3) 0.0545(14) Uani 1 1 d . . . . .
H63 H 0.917950 0.866591 1.105190 0.065 Uiso 1 1 calc R U . . .
C64 C 1.0580(7) 0.9089(4) 1.0562(3) 0.0638(17) Uani 1 1 d . . . . .
H64 H 1.101971 0.951816 1.091987 0.077 Uiso 1 1 calc R U . . .
C65 C 1.1045(10) 0.8972(6) 0.9963(4) 0.121(4) Uani 1 1 d . . . . .
H65 H 1.181498 0.931899 0.991516 0.145 Uiso 1 1 calc R U . . .
C66 C 1.0396(8) 0.8343(6) 0.9413(4) 0.093(3) Uani 1 1 d . . . . .
H66 H 1.072905 0.827377 0.900432 0.111 Uiso 1 1 calc R U . . .
C67 C 1.2841(5) 0.2461(3) 0.8317(2) 0.0401(11) Uani 1 1 d . . . . .
H67A H 1.342975 0.245014 0.797638 0.060 Uiso 1 1 calc R U . . .
H67B H 1.229586 0.191053 0.823388 0.060 Uiso 1 1 calc R U . . .
H67C H 1.341284 0.254927 0.874712 0.060 Uiso 1 1 calc R U . . .
C68 C 0.8223(5) 0.5301(3) 0.7665(2) 0.0384(10) Uani 1 1 d . . . . .
H68A H 0.871936 0.536295 0.730244 0.058 Uiso 1 1 calc R U . . .
H68B H 0.762187 0.577798 0.775003 0.058 Uiso 1 1 calc R U . . .
H68C H 0.766908 0.475176 0.754900 0.058 Uiso 1 1 calc R U . . .
C70 C 0.400(2) 0.9984(17) 0.9276(11) 0.096(9) Uani 0.394(17) 1 d . . P A 2
H70 H 0.366960 0.965856 0.956062 0.115 Uiso 0.394(17) 1 calc R U P A 2
C69 C 0.423(2) 0.9575(13) 0.8649(11) 0.064(5) Uani 0.394(17) 1 d . . P A 2
H69 H 0.384895 0.900366 0.847482 0.077 Uiso 0.394(17) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1S 1.779(6) . ?
Cl2 C1S 1.757(6) . ?
C1S H1SA 0.9700 . ?
C1S H1SB 0.9700 . ?
P1 O2 1.490(3) . ?
P1 C7 1.845(4) . ?
P1 C10 1.792(5) . ?
P1 C16 1.799(4) . ?
O1 C9 1.239(5) . ?
N1 C1 1.405(5) . ?
N1 C7 1.368(5) . ?
N1 C23 1.464(5) . ?
C1 C2 1.400(6) . ?
C1 C6 1.412(6) . ?
C2 C3 1.404(6) . ?
C2 C9 1.470(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.363(6) . ?
C4 C5 1.413(6) . ?
C4 C22 1.508(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.361(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.444(6) . ?
C10 C11 1.394(6) . ?
C10 C15 1.403(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.390(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.402(6) . ?
C16 C21 1.383(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.394(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.407(8) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(7) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
P2 O6 1.485(3) . ?
P2 C30 1.839(4) . ?
P2 C33 1.799(5) . ?
P2 C39 1.795(4) . ?
O3 C32 1.242(5) . ?
N2 C29 1.409(5) . ?
N2 C30 1.372(5) . ?
N2 C46 1.468(5) . ?
C24 C25 1.398(6) . ?
C24 C29 1.403(6) . ?
C24 C32 1.459(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.363(6) . ?
C26 C27 1.408(6) . ?
C26 C45 1.513(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.377(6) . ?
C28 H28 0.9300 . ?
C28 C29 1.398(6) . ?
C30 C31 1.354(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.437(6) . ?
C33 C34 1.370(9) . ?
C33 C38 1.393(13) . ?
C33 C69 1.399(17) . ?
C34 H34 0.9300 . ?
C34 C35 1.391(8) . ?
C35 H35 0.9300 . ?
C35 C36 1.349(10) . ?
C36 H36 0.9300 . ?
C36 H36A 0.9300 . ?
C36 C37 1.483(14) . ?
C36 C70 1.29(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.381(15) . ?
C38 H38 0.9300 . ?
C39 C40 1.389(6) . ?
C39 C44 1.404(6) . ?
C40 H40 0.9300 . ?
C40 C41 1.399(6) . ?
C41 H41 0.9300 . ?
C41 C42 1.389(7) . ?
C42 H42 0.9300 . ?
C42 C43 1.369(7) . ?
C43 H43 0.9300 . ?
C43 C44 1.392(6) . ?
C44 H44 0.9300 . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
P3 O5 1.487(3) . ?
P3 C54 1.844(4) . ?
P3 C55 1.794(4) . ?
P3 C61 1.807(5) . ?
O4 C53 1.242(5) . ?
N3 C47 1.389(5) . ?
N3 C54 1.384(5) . ?
N3 C68 1.468(5) . ?
C00S H00S 0.9300 . ?
C00S C50 1.367(6) . ?
C00S C51 1.409(6) . ?
C47 C48 1.402(6) . ?
C47 C51 1.412(6) . ?
C48 H48 0.9300 . ?
C48 C49 1.383(6) . ?
C49 H49 0.9300 . ?
C49 C50 1.406(6) . ?
C50 C67 1.508(6) . ?
C51 C53 1.455(6) . ?
C52 H52 0.9300 . ?
C52 C53 1.438(6) . ?
C52 C54 1.351(6) . ?
C55 C56 1.402(6) . ?
C55 C60 1.394(6) . ?
C56 H56 0.9300 . ?
C56 C57 1.399(6) . ?
C57 H57 0.9300 . ?
C57 C58 1.373(7) . ?
C58 H58 0.9300 . ?
C58 C59 1.383(8) . ?
C59 H59 0.9300 . ?
C59 C60 1.390(7) . ?
C60 H60 0.9300 . ?
C61 C62 1.384(7) . ?
C61 C66 1.373(7) . ?
C62 H62 0.9300 . ?
C62 C63 1.396(7) . ?
C63 H63 0.9300 . ?
C63 C64 1.330(9) . ?
C64 H64 0.9300 . ?
C64 C65 1.351(10) . ?
C65 H65 0.9300 . ?
C65 C66 1.396(10) . ?
C66 H66 0.9300 . ?
C67 H67A 0.9600 . ?
C67 H67B 0.9600 . ?
C67 H67C 0.9600 . ?
C68 H68A 0.9600 . ?
C68 H68B 0.9600 . ?
C68 H68C 0.9600 . ?
C70 H70 0.9300 . ?
C70 C69 1.37(3) . ?
C69 H69 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 C1S H1SA 109.4 . . ?
Cl1 C1S H1SB 109.4 . . ?
Cl2 C1S Cl1 111.0(3) . . ?
Cl2 C1S H1SA 109.4 . . ?
Cl2 C1S H1SB 109.4 . . ?
H1SA C1S H1SB 108.0 . . ?
O2 P1 C7 112.29(18) . . ?
O2 P1 C10 110.92(19) . . ?
O2 P1 C16 113.82(19) . . ?
C10 P1 C7 106.11(19) . . ?
C10 P1 C16 106.82(19) . . ?
C16 P1 C7 106.41(19) . . ?
C1 N1 C23 118.0(3) . . ?
C7 N1 C1 118.8(3) . . ?
C7 N1 C23 123.2(4) . . ?
N1 C1 C6 120.7(4) . . ?
C2 C1 N1 120.8(4) . . ?
C2 C1 C6 118.6(4) . . ?
C1 C2 C3 119.3(4) . . ?
C1 C2 C9 121.2(4) . . ?
C3 C2 C9 119.5(4) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 C2 122.7(4) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 C5 117.3(4) . . ?
C3 C4 C22 121.8(4) . . ?
C5 C4 C22 120.9(4) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.8(4) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
N1 C7 P1 118.7(3) . . ?
C8 C7 P1 118.8(3) . . ?
C8 C7 N1 122.4(4) . . ?
C7 C8 H8 118.5 . . ?
C7 C8 C9 123.0(4) . . ?
C9 C8 H8 118.5 . . ?
O1 C9 C2 122.6(4) . . ?
O1 C9 C8 123.8(4) . . ?
C8 C9 C2 113.5(4) . . ?
C11 C10 P1 123.2(3) . . ?
C11 C10 C15 118.1(4) . . ?
C15 C10 P1 118.2(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.5(4) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(4) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.1(4) . . ?
C14 C15 H15 119.4 . . ?
C17 C16 P1 121.4(3) . . ?
C21 C16 P1 117.6(3) . . ?
C21 C16 C17 121.0(4) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 C16 118.3(4) . . ?
C18 C17 H17 120.8 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.1(5) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(5) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.3(5) . . ?
C21 C20 H20 120.3 . . ?
C16 C21 C20 120.0(5) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C4 C22 H22A 109.5 . . ?
C4 C22 H22B 109.5 . . ?
C4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 P2 C30 113.79(19) . . ?
O6 P2 C33 111.1(2) . . ?
O6 P2 C39 114.05(19) . . ?
C33 P2 C30 105.0(2) . . ?
C39 P2 C30 106.57(19) . . ?
C39 P2 C33 105.7(2) . . ?
C29 N2 C46 118.4(3) . . ?
C30 N2 C29 119.2(3) . . ?
C30 N2 C46 122.4(4) . . ?
C25 C24 C29 119.0(4) . . ?
C25 C24 C32 119.8(4) . . ?
C29 C24 C32 121.2(4) . . ?
C24 C25 H25 118.6 . . ?
C26 C25 C24 122.8(4) . . ?
C26 C25 H25 118.6 . . ?
C25 C26 C27 117.5(4) . . ?
C25 C26 C45 121.3(4) . . ?
C27 C26 C45 121.2(4) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 C26 121.4(4) . . ?
C28 C27 H27 119.3 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.3(4) . . ?
C29 C28 H28 119.8 . . ?
C24 C29 N2 120.3(4) . . ?
C28 C29 N2 120.8(4) . . ?
C28 C29 C24 118.9(4) . . ?
N2 C30 P2 119.5(3) . . ?
C31 C30 P2 118.7(3) . . ?
C31 C30 N2 121.8(4) . . ?
C30 C31 H31 118.3 . . ?
C30 C31 C32 123.4(4) . . ?
C32 C31 H31 118.3 . . ?
O3 C32 C24 122.3(4) . . ?
O3 C32 C31 123.6(4) . . ?
C31 C32 C24 114.1(4) . . ?
C34 C33 P2 124.9(4) . . ?
C34 C33 C38 119.8(7) . . ?
C34 C33 C69 112.3(10) . . ?
C38 C33 P2 114.6(7) . . ?
C69 C33 P2 120.4(10) . . ?
C33 C34 H34 119.2 . . ?
C33 C34 C35 121.7(6) . . ?
C35 C34 H34 119.2 . . ?
C34 C35 H35 120.5 . . ?
C36 C35 C34 119.0(7) . . ?
C36 C35 H35 120.5 . . ?
C35 C36 H36 120.2 . . ?
C35 C36 H36A 121.5 . . ?
C35 C36 C37 119.5(7) . . ?
C37 C36 H36 120.2 . . ?
C70 C36 C35 117.1(10) . . ?
C70 C36 H36A 121.5 . . ?
C36 C37 H37 121.3 . . ?
C38 C37 C36 117.4(10) . . ?
C38 C37 H37 121.3 . . ?
C33 C38 H38 119.9 . . ?
C37 C38 C33 120.1(11) . . ?
C37 C38 H38 119.9 . . ?
C40 C39 P2 118.3(3) . . ?
C40 C39 C44 120.3(4) . . ?
C44 C39 P2 121.4(3) . . ?
C39 C40 H40 120.1 . . ?
C39 C40 C41 119.7(4) . . ?
C41 C40 H40 120.1 . . ?
C40 C41 H41 120.2 . . ?
C42 C41 C40 119.5(4) . . ?
C42 C41 H41 120.2 . . ?
C41 C42 H42 119.6 . . ?
C43 C42 C41 120.7(4) . . ?
C43 C42 H42 119.6 . . ?
C42 C43 H43 119.6 . . ?
C42 C43 C44 120.8(4) . . ?
C44 C43 H43 119.6 . . ?
C39 C44 H44 120.5 . . ?
C43 C44 C39 118.9(4) . . ?
C43 C44 H44 120.5 . . ?
C26 C45 H45A 109.5 . . ?
C26 C45 H45B 109.5 . . ?
C26 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
N2 C46 H46A 109.5 . . ?
N2 C46 H46B 109.5 . . ?
N2 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O5 P3 C54 112.45(19) . . ?
O5 P3 C55 114.5(2) . . ?
O5 P3 C61 111.8(2) . . ?
C55 P3 C54 107.2(2) . . ?
C55 P3 C61 105.7(2) . . ?
C61 P3 C54 104.50(19) . . ?
C47 N3 C68 118.4(4) . . ?
C54 N3 C47 119.3(3) . . ?
C54 N3 C68 122.3(4) . . ?
C50 C00S H00S 118.7 . . ?
C50 C00S C51 122.7(4) . . ?
C51 C00S H00S 118.7 . . ?
N3 C47 C48 122.0(4) . . ?
N3 C47 C51 120.1(4) . . ?
C48 C47 C51 117.9(4) . . ?
C47 C48 H48 119.5 . . ?
C49 C48 C47 120.9(4) . . ?
C49 C48 H48 119.5 . . ?
C48 C49 H49 119.2 . . ?
C48 C49 C50 121.7(4) . . ?
C50 C49 H49 119.2 . . ?
C00S C50 C49 117.4(4) . . ?
C00S C50 C67 121.4(4) . . ?
C49 C50 C67 121.2(4) . . ?
C00S C51 C47 119.4(4) . . ?
C00S C51 C53 119.2(4) . . ?
C47 C51 C53 121.4(4) . . ?
C53 C52 H52 118.4 . . ?
C54 C52 H52 118.4 . . ?
C54 C52 C53 123.1(4) . . ?
O4 C53 C51 122.9(4) . . ?
O4 C53 C52 123.0(4) . . ?
C52 C53 C51 114.0(4) . . ?
N3 C54 P3 119.4(3) . . ?
C52 C54 P3 118.7(3) . . ?
C52 C54 N3 121.8(4) . . ?
C56 C55 P3 121.6(3) . . ?
C60 C55 P3 118.1(4) . . ?
C60 C55 C56 120.1(4) . . ?
C55 C56 H56 120.4 . . ?
C57 C56 C55 119.3(4) . . ?
C57 C56 H56 120.4 . . ?
C56 C57 H57 120.0 . . ?
C58 C57 C56 120.1(5) . . ?
C58 C57 H57 120.0 . . ?
C57 C58 H58 119.6 . . ?
C57 C58 C59 120.9(5) . . ?
C59 C58 H58 119.6 . . ?
C58 C59 H59 120.0 . . ?
C58 C59 C60 120.1(5) . . ?
C60 C59 H59 120.0 . . ?
C55 C60 H60 120.2 . . ?
C59 C60 C55 119.6(5) . . ?
C59 C60 H60 120.2 . . ?
C62 C61 P3 123.6(4) . . ?
C66 C61 P3 118.6(4) . . ?
C66 C61 C62 117.8(5) . . ?
C61 C62 H62 119.6 . . ?
C61 C62 C63 120.8(5) . . ?
C63 C62 H62 119.6 . . ?
C62 C63 H63 119.8 . . ?
C64 C63 C62 120.5(6) . . ?
C64 C63 H63 119.8 . . ?
C63 C64 H64 120.1 . . ?
C63 C64 C65 119.8(6) . . ?
C65 C64 H64 120.1 . . ?
C64 C65 H65 119.3 . . ?
C64 C65 C66 121.4(7) . . ?
C66 C65 H65 119.3 . . ?
C61 C66 C65 119.6(6) . . ?
C61 C66 H66 120.2 . . ?
C65 C66 H66 120.2 . . ?
C50 C67 H67A 109.5 . . ?
C50 C67 H67B 109.5 . . ?
C50 C67 H67C 109.5 . . ?
H67A C67 H67B 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
N3 C68 H68A 109.5 . . ?
N3 C68 H68B 109.5 . . ?
N3 C68 H68C 109.5 . . ?
H68A C68 H68B 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 109.5 . . ?
C36 C70 H70 120.2 . . ?
C36 C70 C69 119.6(16) . . ?
C69 C70 H70 120.2 . . ?
C33 C69 H69 118.9 . . ?
C70 C69 C33 122.2(19) . . ?
C70 C69 H69 118.9 . . ?

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 C7 C8 C9 174.5(3) . . . . ?
P1 C10 C11 C12 170.9(4) . . . . ?
P1 C10 C15 C14 -171.2(4) . . . . ?
P1 C16 C17 C18 -174.6(3) . . . . ?
P1 C16 C21 C20 175.4(4) . . . . ?
O2 P1 C7 N1 42.3(4) . . . . ?
O2 P1 C7 C8 -134.0(3) . . . . ?
O2 P1 C10 C11 -119.1(4) . . . . ?
O2 P1 C10 C15 51.8(4) . . . . ?
O2 P1 C16 C17 -159.9(3) . . . . ?
O2 P1 C16 C21 23.0(4) . . . . ?
N1 C1 C2 C3 177.5(4) . . . . ?
N1 C1 C2 C9 -1.9(6) . . . . ?
N1 C1 C6 C5 -178.6(4) . . . . ?
N1 C7 C8 C9 -1.6(6) . . . . ?
C1 N1 C7 P1 -170.7(3) . . . . ?
C1 N1 C7 C8 5.4(6) . . . . ?
C1 C2 C3 C4 2.1(7) . . . . ?
C1 C2 C9 O1 -177.1(4) . . . . ?
C1 C2 C9 C8 5.3(6) . . . . ?
C2 C1 C6 C5 0.9(7) . . . . ?
C2 C3 C4 C5 -0.9(7) . . . . ?
C2 C3 C4 C22 179.7(4) . . . . ?
C3 C2 C9 O1 3.5(6) . . . . ?
C3 C2 C9 C8 -174.1(4) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C1 0.3(7) . . . . ?
C6 C1 C2 C3 -2.1(6) . . . . ?
C6 C1 C2 C9 178.6(4) . . . . ?
C7 P1 C10 C11 118.7(4) . . . . ?
C7 P1 C10 C15 -70.4(4) . . . . ?
C7 P1 C16 C17 -35.7(4) . . . . ?
C7 P1 C16 C21 147.2(4) . . . . ?
C7 N1 C1 C2 -3.6(6) . . . . ?
C7 N1 C1 C6 175.9(4) . . . . ?
C7 C8 C9 O1 178.8(4) . . . . ?
C7 C8 C9 C2 -3.6(6) . . . . ?
C9 C2 C3 C4 -178.6(4) . . . . ?
C10 P1 C7 N1 163.6(3) . . . . ?
C10 P1 C7 C8 -12.7(4) . . . . ?
C10 P1 C16 C17 77.3(4) . . . . ?
C10 P1 C16 C21 -99.8(4) . . . . ?
C10 C11 C12 C13 -1.3(7) . . . . ?
C11 C10 C15 C14 0.1(7) . . . . ?
C11 C12 C13 C14 2.5(7) . . . . ?
C12 C13 C14 C15 -2.4(7) . . . . ?
C13 C14 C15 C10 1.1(7) . . . . ?
C15 C10 C11 C12 0.0(7) . . . . ?
C16 P1 C7 N1 -82.9(3) . . . . ?
C16 P1 C7 C8 100.8(4) . . . . ?
C16 P1 C10 C11 5.5(4) . . . . ?
C16 P1 C10 C15 176.4(3) . . . . ?
C16 C17 C18 C19 -1.1(7) . . . . ?
C17 C16 C21 C20 -1.7(8) . . . . ?
C17 C18 C19 C20 -0.8(8) . . . . ?
C18 C19 C20 C21 1.5(9) . . . . ?
C19 C20 C21 C16 -0.3(9) . . . . ?
C21 C16 C17 C18 2.4(7) . . . . ?
C22 C4 C5 C6 179.1(5) . . . . ?
C23 N1 C1 C2 177.0(4) . . . . ?
C23 N1 C1 C6 -3.4(6) . . . . ?
C23 N1 C7 P1 8.6(5) . . . . ?
C23 N1 C7 C8 -175.2(4) . . . . ?
P2 C30 C31 C32 -175.9(3) . . . . ?
P2 C33 C34 C35 -178.9(5) . . . . ?
P2 C33 C38 C37 -180.0(8) . . . . ?
P2 C33 C69 C70 172.8(13) . . . . ?
P2 C39 C40 C41 -175.6(3) . . . . ?
P2 C39 C44 C43 174.7(3) . . . . ?
O6 P2 C30 N2 -52.9(4) . . . . ?
O6 P2 C30 C31 124.8(3) . . . . ?
O6 P2 C33 C34 148.3(5) . . . . ?
O6 P2 C33 C38 -41.2(7) . . . . ?
O6 P2 C33 C69 -12.6(13) . . . . ?
O6 P2 C39 C40 -24.6(4) . . . . ?
O6 P2 C39 C44 158.2(3) . . . . ?
N2 C30 C31 C32 1.8(7) . . . . ?
C24 C25 C26 C27 0.9(7) . . . . ?
C24 C25 C26 C45 179.9(4) . . . . ?
C25 C24 C29 N2 -178.8(4) . . . . ?
C25 C24 C29 C28 0.0(6) . . . . ?
C25 C24 C32 O3 -1.0(7) . . . . ?
C25 C24 C32 C31 177.5(4) . . . . ?
C25 C26 C27 C28 -1.5(7) . . . . ?
C26 C27 C28 C29 1.4(7) . . . . ?
C27 C28 C29 N2 178.2(4) . . . . ?
C27 C28 C29 C24 -0.7(6) . . . . ?
C29 N2 C30 P2 174.5(3) . . . . ?
C29 N2 C30 C31 -3.1(6) . . . . ?
C29 C24 C25 C26 -0.2(7) . . . . ?
C29 C24 C32 O3 -179.8(4) . . . . ?
C29 C24 C32 C31 -1.2(6) . . . . ?
C30 P2 C33 C34 -88.3(5) . . . . ?
C30 P2 C33 C38 82.2(7) . . . . ?
C30 P2 C33 C69 110.8(12) . . . . ?
C30 P2 C39 C40 -151.1(3) . . . . ?
C30 P2 C39 C44 31.8(4) . . . . ?
C30 N2 C29 C24 2.3(6) . . . . ?
C30 N2 C29 C28 -176.6(4) . . . . ?
C30 C31 C32 O3 179.0(4) . . . . ?
C30 C31 C32 C24 0.4(6) . . . . ?
C32 C24 C25 C26 -178.9(4) . . . . ?
C32 C24 C29 N2 -0.1(6) . . . . ?
C32 C24 C29 C28 178.8(4) . . . . ?
C33 P2 C30 N2 -174.6(3) . . . . ?
C33 P2 C30 C31 3.2(4) . . . . ?
C33 P2 C39 C40 97.7(4) . . . . ?
C33 P2 C39 C44 -79.5(4) . . . . ?
C33 C34 C35 C36 0.8(10) . . . . ?
C34 C33 C38 C37 -8.9(13) . . . . ?
C34 C33 C69 C70 10(2) . . . . ?
C34 C35 C36 C37 -13.9(12) . . . . ?
C34 C35 C36 C70 24.3(15) . . . . ?
C35 C36 C37 C38 15.5(15) . . . . ?
C35 C36 C70 C69 -32(2) . . . . ?
C36 C37 C38 C33 -3.9(15) . . . . ?
C36 C70 C69 C33 15(3) . . . . ?
C38 C33 C34 C35 11.1(11) . . . . ?
C39 P2 C30 N2 73.7(4) . . . . ?
C39 P2 C30 C31 -108.6(4) . . . . ?
C39 P2 C33 C34 24.1(6) . . . . ?
C39 P2 C33 C38 -165.4(7) . . . . ?
C39 P2 C33 C69 -136.8(12) . . . . ?
C39 C40 C41 C42 0.1(7) . . . . ?
C40 C39 C44 C43 -2.4(6) . . . . ?
C40 C41 C42 C43 -1.0(7) . . . . ?
C41 C42 C43 C44 0.2(7) . . . . ?
C42 C43 C44 C39 1.5(7) . . . . ?
C44 C39 C40 C41 1.7(7) . . . . ?
C45 C26 C27 C28 179.5(4) . . . . ?
C46 N2 C29 C24 178.6(4) . . . . ?
C46 N2 C29 C28 -0.3(6) . . . . ?
C46 N2 C30 P2 -1.6(5) . . . . ?
C46 N2 C30 C31 -179.3(4) . . . . ?
P3 C55 C56 C57 173.6(3) . . . . ?
P3 C55 C60 C59 -173.6(4) . . . . ?
P3 C61 C62 C63 180.0(4) . . . . ?
P3 C61 C66 C65 -179.8(8) . . . . ?
O5 P3 C54 N3 -45.1(4) . . . . ?
O5 P3 C54 C52 131.2(4) . . . . ?
O5 P3 C55 C56 158.5(3) . . . . ?
O5 P3 C55 C60 -26.2(4) . . . . ?
O5 P3 C61 C62 149.0(4) . . . . ?
O5 P3 C61 C66 -31.8(6) . . . . ?
N3 C47 C48 C49 178.4(4) . . . . ?
N3 C47 C51 C00S -178.3(4) . . . . ?
N3 C47 C51 C53 2.0(6) . . . . ?
C00S C51 C53 O4 -1.9(7) . . . . ?
C00S C51 C53 C52 175.6(4) . . . . ?
C47 N3 C54 P3 171.6(3) . . . . ?
C47 N3 C54 C52 -4.5(6) . . . . ?
C47 C48 C49 C50 -0.2(7) . . . . ?
C47 C51 C53 O4 177.8(4) . . . . ?
C47 C51 C53 C52 -4.8(6) . . . . ?
C48 C47 C51 C00S 0.3(6) . . . . ?
C48 C47 C51 C53 -179.4(4) . . . . ?
C48 C49 C50 C00S 0.5(7) . . . . ?
C48 C49 C50 C67 -178.9(4) . . . . ?
C50 C00S C51 C47 0.0(6) . . . . ?
C50 C00S C51 C53 179.7(4) . . . . ?
C51 C00S C50 C49 -0.3(7) . . . . ?
C51 C00S C50 C67 179.0(4) . . . . ?
C51 C47 C48 C49 -0.2(6) . . . . ?
C53 C52 C54 P3 -174.8(3) . . . . ?
C53 C52 C54 N3 1.4(7) . . . . ?
C54 P3 C55 C56 33.0(4) . . . . ?
C54 P3 C55 C60 -151.7(4) . . . . ?
C54 P3 C61 C62 -89.1(4) . . . . ?
C54 P3 C61 C66 90.1(6) . . . . ?
C54 N3 C47 C48 -175.8(4) . . . . ?
C54 N3 C47 C51 2.8(6) . . . . ?
C54 C52 C53 O4 -179.4(4) . . . . ?
C54 C52 C53 C51 3.1(6) . . . . ?
C55 P3 C54 N3 81.6(4) . . . . ?
C55 P3 C54 C52 -102.1(4) . . . . ?
C55 P3 C61 C62 23.9(5) . . . . ?
C55 P3 C61 C66 -156.9(6) . . . . ?
C55 C56 C57 C58 0.2(7) . . . . ?
C56 C55 C60 C59 1.7(7) . . . . ?
C56 C57 C58 C59 1.2(8) . . . . ?
C57 C58 C59 C60 -1.1(9) . . . . ?
C58 C59 C60 C55 -0.4(8) . . . . ?
C60 C55 C56 C57 -1.6(7) . . . . ?
C61 P3 C54 N3 -166.5(3) . . . . ?
C61 P3 C54 C52 9.8(4) . . . . ?
C61 P3 C55 C56 -78.1(4) . . . . ?
C61 P3 C55 C60 97.2(4) . . . . ?
C61 C62 C63 C64 -0.2(10) . . . . ?
C62 C61 C66 C65 -0.5(12) . . . . ?
C62 C63 C64 C65 -0.7(12) . . . . ?
C63 C64 C65 C66 0.9(16) . . . . ?
C64 C65 C66 C61 -0.3(17) . . . . ?
C66 C61 C62 C63 0.8(9) . . . . ?
C68 N3 C47 C48 2.7(6) . . . . ?
C68 N3 C47 C51 -178.7(4) . . . . ?
C68 N3 C54 P3 -6.8(5) . . . . ?
C68 N3 C54 C52 177.0(4) . . . . ?
C69 C33 C34 C35 -16.6(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.366
_oxdiff_exptl_absorpt_empirical_full_min 0.397
