# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

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

data_cain71_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc250xz3
_database_code_depnum_ccdc_archive 'CCDC 1996895'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0DT01367F 2020
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2020-12-19 deposited with the CCDC.	2021-01-05 downloaded from the CCDC.
;
_audit_creation_date             2018-06-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H23 Cl N P'
_chemical_formula_sum            'C19 H23 Cl N P'
_chemical_formula_weight         331.80
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.7432(6)
_cell_length_b                   10.4564(5)
_cell_length_c                   15.0518(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.441(3)
_cell_angle_gamma                90
_cell_volume                     1781.52(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9779
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.325
_cell_measurement_theta_min      3.907
_shelx_estimated_absorpt_T_max   0.530
_shelx_estimated_absorpt_T_min   0.470
_exptl_absorpt_coefficient_mu    2.698
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0761 before and 0.0654 after correction. The Ratio of minimum to maximum transmission is 0.8215. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14613
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.234
_diffrn_reflns_theta_min         3.905
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker Pt135'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3142
_reflns_number_total             3381
_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       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.147
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.045
_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)+(0.0578P)²+2.2681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1256
_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 Ternary CH refined with riding coordinates:
 C14(H14), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.86040(5) 0.56498(5) 0.53932(4) 0.02981(18) Uani 1 1 d . . . . .
P1 P 0.70398(5) 0.47849(5) 0.44991(3) 0.01936(16) Uani 1 1 d . . . . .
N1 N 0.73466(14) 0.45405(16) 0.34923(11) 0.0155(3) Uani 1 1 d . . . . .
C1 C 0.80141(19) 0.33700(19) 0.33869(13) 0.0188(4) Uani 1 1 d . . . . .
H1A H 0.884628 0.357771 0.341789 0.023 Uiso 1 1 calc R . . . .
H1B H 0.765067 0.294165 0.279242 0.023 Uiso 1 1 calc R . . . .
C2 C 0.79377(17) 0.25311(19) 0.41909(13) 0.0165(4) Uani 1 1 d . . . . .
C3 C 0.83039(18) 0.1261(2) 0.43239(14) 0.0197(4) Uani 1 1 d . . . . .
H3 H 0.867396 0.085558 0.390926 0.024 Uiso 1 1 calc R . . . .
C4 C 0.81187(19) 0.0598(2) 0.50731(14) 0.0228(5) Uani 1 1 d . . . . .
H4 H 0.835829 -0.027031 0.516685 0.027 Uiso 1 1 calc R . . . .
C5 C 0.75867(19) 0.1190(2) 0.56882(14) 0.0248(5) Uani 1 1 d . . . . .
H5 H 0.745181 0.071707 0.618964 0.030 Uiso 1 1 calc R . . . .
C6 C 0.72513(18) 0.2467(2) 0.55737(14) 0.0218(4) Uani 1 1 d . . . . .
H6 H 0.690483 0.287822 0.600072 0.026 Uiso 1 1 calc R . . . .
C7 C 0.74328(17) 0.31351(19) 0.48204(13) 0.0173(4) Uani 1 1 d . . . . .
C8 C 0.69440(17) 0.53655(18) 0.27048(13) 0.0148(4) Uani 1 1 d . . . . .
C9 C 0.77333(17) 0.62387(19) 0.24763(13) 0.0170(4) Uani 1 1 d . . . . .
C10 C 0.73188(19) 0.6984(2) 0.16840(14) 0.0202(4) Uani 1 1 d . . . . .
H10 H 0.783932 0.757140 0.151141 0.024 Uiso 1 1 calc R . . . .
C11 C 0.61647(19) 0.6884(2) 0.11462(14) 0.0224(4) Uani 1 1 d . . . . .
H11 H 0.590014 0.740219 0.061255 0.027 Uiso 1 1 calc R . . . .
C12 C 0.53956(18) 0.6028(2) 0.13861(14) 0.0203(4) Uani 1 1 d . . . . .
H12 H 0.460334 0.597085 0.101706 0.024 Uiso 1 1 calc R . . . .
C13 C 0.57695(18) 0.52461(19) 0.21646(14) 0.0167(4) Uani 1 1 d . . . . .
C14 C 0.89902(18) 0.6407(2) 0.30634(15) 0.0211(4) Uani 1 1 d . . . . .
H14 H 0.914189 0.575275 0.356613 0.025 Uiso 1 1 calc R . . . .
C15 C 0.9884(2) 0.6197(3) 0.24984(18) 0.0330(5) Uani 1 1 d . . . . .
H15A H 0.977771 0.533933 0.222591 0.050 Uiso 1 1 calc GR . . . .
H15B H 1.068765 0.627878 0.290098 0.050 Uiso 1 1 calc GR . . . .
H15C H 0.975871 0.683806 0.200699 0.050 Uiso 1 1 calc GR . . . .
C16 C 0.9151(2) 0.7738(2) 0.35106(19) 0.0349(6) Uani 1 1 d . . . . .
H16A H 0.903524 0.839323 0.302941 0.052 Uiso 1 1 calc GR . . . .
H16B H 0.994955 0.781121 0.392230 0.052 Uiso 1 1 calc GR . . . .
H16C H 0.856980 0.785822 0.386534 0.052 Uiso 1 1 calc GR . . . .
C17 C 0.48962(18) 0.4318(2) 0.24008(14) 0.0200(4) Uani 1 1 d . . . . .
H17 H 0.534612 0.374118 0.290235 0.024 Uiso 1 1 calc R . . . .
C18 C 0.3990(2) 0.5060(2) 0.27721(17) 0.0270(5) Uani 1 1 d . . . . .
H18A H 0.439415 0.548611 0.334995 0.040 Uiso 1 1 calc GR . . . .
H18B H 0.339844 0.446527 0.288465 0.040 Uiso 1 1 calc GR . . . .
H18C H 0.359921 0.570198 0.231847 0.040 Uiso 1 1 calc GR . . . .
C19 C 0.42850(19) 0.3482(2) 0.15759(16) 0.0258(5) Uani 1 1 d . . . . .
H19A H 0.380683 0.402268 0.108467 0.039 Uiso 1 1 calc GR . . . .
H19B H 0.377440 0.285772 0.176705 0.039 Uiso 1 1 calc GR . . . .
H19C H 0.488257 0.303124 0.134810 0.039 Uiso 1 1 calc GR . . . .


_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 P1 2.1649(8) . ?
P1 N1 1.6681(16) . ?
P1 C7 1.818(2) . ?
N1 C1 1.485(3) . ?
N1 C8 1.440(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.517(3) . ?
C2 C3 1.394(3) . ?
C2 C7 1.395(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(3) . ?
C8 C9 1.408(3) . ?
C8 C13 1.408(3) . ?
C9 C10 1.399(3) . ?
C9 C14 1.515(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.400(3) . ?
C13 C17 1.521(3) . ?
C14 H14 1.0000 . ?
C14 C15 1.533(3) . ?
C14 C16 1.536(3) . ?
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 H17 1.0000 . ?
C17 C18 1.538(3) . ?
C17 C19 1.532(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
N1 P1 Cl1 106.02(6) . . ?
N1 P1 C7 89.74(9) . . ?
C7 P1 Cl1 96.76(6) . . ?
C1 N1 P1 118.12(13) . . ?
C8 N1 P1 123.57(13) . . ?
C8 N1 C1 118.22(15) . . ?
N1 C1 H1A 110.9 . . ?
N1 C1 H1B 110.9 . . ?
N1 C1 C2 104.27(16) . . ?
H1A C1 H1B 108.9 . . ?
C2 C1 H1A 110.9 . . ?
C2 C1 H1B 110.9 . . ?
C3 C2 C1 125.74(18) . . ?
C3 C2 C7 120.29(18) . . ?
C7 C2 C1 113.96(18) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.88(19) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.8(2) . . ?
C7 C6 H6 120.6 . . ?
C2 C7 P1 111.88(15) . . ?
C6 C7 P1 127.46(16) . . ?
C6 C7 C2 120.64(19) . . ?
C9 C8 N1 119.77(17) . . ?
C9 C8 C13 121.60(18) . . ?
C13 C8 N1 118.60(17) . . ?
C8 C9 C14 122.36(18) . . ?
C10 C9 C8 117.87(18) . . ?
C10 C9 C14 119.76(18) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.34(19) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.05(19) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 120.94(19) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C17 122.63(18) . . ?
C12 C13 C8 118.19(18) . . ?
C12 C13 C17 119.17(18) . . ?
C9 C14 H14 108.2 . . ?
C9 C14 C15 111.38(18) . . ?
C9 C14 C16 110.33(18) . . ?
C15 C14 H14 108.2 . . ?
C15 C14 C16 110.5(2) . . ?
C16 C14 H14 108.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17 107.9 . . ?
C13 C17 C18 109.74(17) . . ?
C13 C17 C19 111.97(17) . . ?
C18 C17 H17 107.9 . . ?
C19 C17 H17 107.9 . . ?
C19 C17 C18 111.24(17) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_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_cain94_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc26vyjk
_database_code_depnum_ccdc_archive 'CCDC 2051689'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0DT01367F 2020
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2020-12-19 deposited with the CCDC.	2021-01-05 downloaded from the CCDC.
;
_audit_creation_date             2020-09-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C43 H77 I N P3 Pd2'
_chemical_formula_sum            'C43 H77 I N P3 Pd2'
_chemical_formula_weight         1040.66
_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'
I I -0.4742 1.8119 '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'
Pd Pd -0.9988 1.0072 '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                   13.6610(2)
_cell_length_b                   23.3921(3)
_cell_length_c                   15.1918(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.8940(10)
_cell_angle_gamma                90
_cell_volume                     4645.17(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.776
_shelx_estimated_absorpt_T_min   0.659
_exptl_absorpt_coefficient_mu    1.571
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0797 before and 0.0684 after correction.
The Ratio of minimum to maximum transmission is 0.8790.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38348
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_min         1.649
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_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                9880
_reflns_number_total             11515
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         11515
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0166P)²+2.6677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0769
_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 Ternary CH refined with riding coordinates:
 C17(H17), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Me refined with riding coordinates:
 C31(H31A,H31B,H31C)
2.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C11(H11), C2(H2), C4(H4), C3(H3), C5(H5)
2.e Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C35(H35A,H35B,
 H35C), C33(H33A,H33B,H33C), C38(H38A,H38B,H38C), C21(H21A,H21B,H21C), C19(H19A,
 H19B,H19C), C29(H29A,H29B,H29C), C39(H39A,H39B,H39C), C37(H37A,H37B,H37C),
 C15(H15A,H15B,H15C), C34(H34A,H34B,H34C), C30(H30A,H30B,H30C), C18(H18A,H18B,
 H18C), C25(H25A,H25B,H25C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C26(H26A,
 H26B,H26C), C27(H27A,H27B,H27C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I1 I 0.71995(2) 0.50502(2) 0.87903(2) 0.01363(5) Uani 1 1 d . . . . .
Pd1 Pd 0.64325(2) 0.61326(2) 0.82638(2) 0.00969(5) Uani 1 1 d . . . . .
Pd2 Pd 0.78344(2) 0.57174(2) 0.75746(2) 0.00912(5) Uani 1 1 d . . . . .
P1 P 0.69125(5) 0.64952(3) 0.70817(5) 0.00995(13) Uani 1 1 d . . . . .
P3 P 0.93954(5) 0.54944(3) 0.73012(5) 0.01064(13) Uani 1 1 d . . . . .
P2 P 0.57689(5) 0.66801(3) 0.92543(5) 0.01269(13) Uani 1 1 d . . . . .
N1 N 0.61488(16) 0.66696(8) 0.60160(15) 0.0122(4) Uani 1 1 d . . . . .
C8 C 0.55588(19) 0.62820(10) 0.53227(19) 0.0131(5) Uani 1 1 d . . . . .
C13 C 0.5802(2) 0.62262(10) 0.44814(19) 0.0140(5) Uani 1 1 d . . . . .
C28 C 0.5375(2) 0.74450(11) 0.8847(2) 0.0171(6) Uani 1 1 d . . . . .
C7 C 0.6021(2) 0.72902(10) 0.58159(19) 0.0157(5) Uani 1 1 d . . . . .
H7A H 0.534621 0.742291 0.585328 0.019 Uiso 1 1 calc R U . . .
H7B H 0.607329 0.737315 0.519205 0.019 Uiso 1 1 calc R U . . .
C9 C 0.4718(2) 0.59878(10) 0.54588(19) 0.0139(5) Uani 1 1 d . . . . .
C1 C 0.74261(19) 0.72111(10) 0.72149(18) 0.0117(5) Uani 1 1 d . . . . .
C40 C 0.9195(2) 0.48360(10) 0.6530(2) 0.0145(5) Uani 1 1 d . . . . .
C10 C 0.4165(2) 0.56178(11) 0.4769(2) 0.0180(6) Uani 1 1 d . . . . .
H10 H 0.360961 0.540829 0.486603 0.022 Uiso 1 1 calc R U . . .
C32 C 0.9924(2) 0.60957(10) 0.67143(19) 0.0134(5) Uani 1 1 d . . . . .
C43 C 0.8580(2) 0.50159(12) 0.5555(2) 0.0192(6) Uani 1 1 d . . . . .
H43A H 0.797762 0.523439 0.558222 0.029 Uiso 1 1 calc R U . . .
H43B H 0.836100 0.467449 0.517485 0.029 Uiso 1 1 calc R U . . .
H43C H 0.900910 0.525363 0.528509 0.029 Uiso 1 1 calc R U . . .
C17 C 0.6670(2) 0.65445(11) 0.4242(2) 0.0167(5) Uani 1 1 d . . . . .
H17 H 0.713163 0.671189 0.481976 0.020 Uiso 1 1 calc R U . . .
C41 C 1.0162(2) 0.45113(11) 0.6482(2) 0.0205(6) Uani 1 1 d . . . . .
H41A H 1.061245 0.477224 0.627667 0.031 Uiso 1 1 calc R U . . .
H41B H 0.996429 0.419317 0.604695 0.031 Uiso 1 1 calc R U . . .
H41C H 1.052372 0.436221 0.709328 0.031 Uiso 1 1 calc R U . . .
C6 C 0.6867(2) 0.75798(10) 0.65318(19) 0.0140(5) Uani 1 1 d . . . . .
C42 C 0.8495(2) 0.44169(11) 0.6852(2) 0.0191(6) Uani 1 1 d . . . . .
H42A H 0.886784 0.425798 0.745237 0.029 Uiso 1 1 calc R U . . .
H42B H 0.828604 0.410612 0.640344 0.029 Uiso 1 1 calc R U . . .
H42C H 0.788719 0.462058 0.690287 0.029 Uiso 1 1 calc R U . . .
C12 C 0.5211(2) 0.58594(11) 0.3808(2) 0.0167(5) Uani 1 1 d . . . . .
H12 H 0.536411 0.582129 0.324001 0.020 Uiso 1 1 calc R U . . .
C11 C 0.4401(2) 0.55480(11) 0.3954(2) 0.0178(6) Uani 1 1 d . . . . .
H11 H 0.401783 0.529182 0.349749 0.021 Uiso 1 1 calc R U . . .
C2 C 0.8240(2) 0.74191(11) 0.79241(19) 0.0151(5) Uani 1 1 d . . . . .
H2 H 0.862649 0.716773 0.838675 0.018 Uiso 1 1 calc R U . . .
C35 C 0.9015(2) 0.63662(11) 0.5980(2) 0.0178(6) Uani 1 1 d . . . . .
H35A H 0.879310 0.610899 0.545038 0.027 Uiso 1 1 calc R U . . .
H35B H 0.922620 0.673290 0.578242 0.027 Uiso 1 1 calc R U . . .
H35C H 0.844684 0.642855 0.624239 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7919(2) 0.83626(11) 0.7269(2) 0.0209(6) Uani 1 1 d . . . . .
H4 H 0.808967 0.875713 0.729391 0.025 Uiso 1 1 calc R U . . .
C36 C 1.0418(2) 0.53215(11) 0.8419(2) 0.0177(6) Uani 1 1 d . . . . .
C20 C 0.6865(2) 0.67262(12) 1.0378(2) 0.0203(6) Uani 1 1 d . . . . .
C3 C 0.8484(2) 0.79958(11) 0.7951(2) 0.0201(6) Uani 1 1 d . . . . .
H3 H 0.903653 0.814067 0.843428 0.024 Uiso 1 1 calc R U . . .
C33 C 1.0740(2) 0.59234(12) 0.6247(2) 0.0190(6) Uani 1 1 d . . . . .
H33A H 1.130750 0.573069 0.669521 0.028 Uiso 1 1 calc R U . . .
H33B H 1.099593 0.626613 0.601540 0.028 Uiso 1 1 calc R U . . .
H33C H 1.043693 0.566383 0.573423 0.028 Uiso 1 1 calc R U . . .
C38 C 1.1526(2) 0.52971(13) 0.8365(2) 0.0224(6) Uani 1 1 d . . . . .
H38A H 1.158144 0.499958 0.792801 0.034 Uiso 1 1 calc R U . . .
H38B H 1.198975 0.520835 0.897435 0.034 Uiso 1 1 calc R U . . .
H38C H 1.171100 0.566775 0.815868 0.034 Uiso 1 1 calc R U . . .
C21 C 0.7874(2) 0.68297(14) 1.0137(2) 0.0253(7) Uani 1 1 d . . . . .
H21A H 0.796123 0.653271 0.971042 0.038 Uiso 1 1 calc R U . . .
H21B H 0.845026 0.681621 1.069965 0.038 Uiso 1 1 calc R U . . .
H21C H 0.785190 0.720564 0.984682 0.038 Uiso 1 1 calc R U . . .
C24 C 0.4622(2) 0.63405(11) 0.9540(2) 0.0222(6) Uani 1 1 d . . . . .
C19 C 0.6260(2) 0.70356(12) 0.3551(2) 0.0223(6) Uani 1 1 d . . . . .
H19A H 0.579406 0.687941 0.298484 0.033 Uiso 1 1 calc R U . . .
H19B H 0.683389 0.722676 0.340873 0.033 Uiso 1 1 calc R U . . .
H19C H 0.589172 0.731184 0.382232 0.033 Uiso 1 1 calc R U . . .
C14 C 0.4305(2) 0.60917(10) 0.6277(2) 0.0151(5) Uani 1 1 d . . . . .
H14 H 0.483143 0.631116 0.675163 0.018 Uiso 1 1 calc R U . . .
C29 C 0.6331(2) 0.77947(11) 0.8886(2) 0.0214(6) Uani 1 1 d . . . . .
H29A H 0.670052 0.787924 0.952817 0.032 Uiso 1 1 calc R U . . .
H29B H 0.613162 0.815342 0.854773 0.032 Uiso 1 1 calc R U . . .
H29C H 0.677518 0.757585 0.860570 0.032 Uiso 1 1 calc R U . . .
C39 C 1.0184(2) 0.47372(12) 0.8790(2) 0.0208(6) Uani 1 1 d . . . . .
H39A H 0.946761 0.472778 0.879123 0.031 Uiso 1 1 calc R U . . .
H39B H 1.063023 0.468288 0.941785 0.031 Uiso 1 1 calc R U . . .
H39C H 1.030655 0.443083 0.839438 0.031 Uiso 1 1 calc R U . . .
C37 C 1.0347(2) 0.57693(13) 0.9140(2) 0.0229(6) Uani 1 1 d . . . . .
H37A H 1.052431 0.614673 0.895165 0.034 Uiso 1 1 calc R U . . .
H37B H 1.082276 0.566851 0.973782 0.034 Uiso 1 1 calc R U . . .
H37C H 0.964728 0.577794 0.918910 0.034 Uiso 1 1 calc R U . . .
C5 C 0.7110(2) 0.81608(11) 0.6554(2) 0.0191(6) Uani 1 1 d . . . . .
H5 H 0.672862 0.841258 0.608934 0.023 Uiso 1 1 calc R U . . .
C31 C 0.4764(2) 0.77698(11) 0.9386(2) 0.0235(6) Uani 1 1 d . . . . .
H31A H 0.414508 0.755385 0.937164 0.035 Uiso 1 1 calc R U . . .
H31B H 0.518424 0.781707 1.002525 0.035 Uiso 1 1 calc R U . . .
H31C H 0.457247 0.814651 0.910690 0.035 Uiso 1 1 calc R U . . .
C15 C 0.4083(2) 0.55385(11) 0.6720(2) 0.0219(6) Uani 1 1 d . . . . .
H15A H 0.363604 0.529374 0.624761 0.033 Uiso 1 1 calc R U . . .
H15B H 0.374369 0.562912 0.718922 0.033 Uiso 1 1 calc R U . . .
H15C H 0.472671 0.533806 0.700630 0.033 Uiso 1 1 calc R U . . .
C34 C 1.0365(2) 0.65775(11) 0.7408(2) 0.0211(6) Uani 1 1 d . . . . .
H34A H 0.986796 0.667876 0.773572 0.032 Uiso 1 1 calc R U . . .
H34B H 1.050588 0.691342 0.707909 0.032 Uiso 1 1 calc R U . . .
H34C H 1.100036 0.644682 0.785055 0.032 Uiso 1 1 calc R U . . .
C30 C 0.4757(2) 0.74275(12) 0.7825(2) 0.0230(6) Uani 1 1 d . . . . .
H30A H 0.515606 0.723260 0.747346 0.035 Uiso 1 1 calc R U . . .
H30B H 0.460433 0.781851 0.759465 0.035 Uiso 1 1 calc R U . . .
H30C H 0.411541 0.722009 0.775611 0.035 Uiso 1 1 calc R U . . .
C18 C 0.7303(2) 0.61483(13) 0.3818(2) 0.0211(6) Uani 1 1 d . . . . .
H18A H 0.750197 0.580743 0.420411 0.032 Uiso 1 1 calc R U . . .
H18B H 0.791857 0.634965 0.377991 0.032 Uiso 1 1 calc R U . . .
H18C H 0.689452 0.603426 0.320007 0.032 Uiso 1 1 calc R U . . .
C25 C 0.4770(3) 0.56837(12) 0.9559(3) 0.0274(7) Uani 1 1 d . . . . .
H25A H 0.484337 0.555618 0.896663 0.041 Uiso 1 1 calc R U . . .
H25B H 0.417378 0.549739 0.966890 0.041 Uiso 1 1 calc R U . . .
H25C H 0.538625 0.558198 1.005185 0.041 Uiso 1 1 calc R U . . .
C16 C 0.3338(2) 0.64620(12) 0.5959(2) 0.0216(6) Uani 1 1 d . . . . .
H16A H 0.350826 0.682763 0.572426 0.032 Uiso 1 1 calc R U . . .
H16B H 0.306561 0.653185 0.647877 0.032 Uiso 1 1 calc R U . . .
H16C H 0.282254 0.626300 0.546943 0.032 Uiso 1 1 calc R U . . .
C23 C 0.6768(2) 0.71877(13) 1.1078(2) 0.0257(7) Uani 1 1 d . . . . .
H23A H 0.676498 0.756767 1.080499 0.039 Uiso 1 1 calc R U . . .
H23B H 0.734943 0.715746 1.163438 0.039 Uiso 1 1 calc R U . . .
H23C H 0.612956 0.713020 1.123647 0.039 Uiso 1 1 calc R U . . .
C26 C 0.4423(3) 0.65244(13) 1.0447(3) 0.0313(8) Uani 1 1 d . . . . .
H26A H 0.499287 0.639898 1.096806 0.047 Uiso 1 1 calc R U . . .
H26B H 0.378648 0.634966 1.049016 0.047 Uiso 1 1 calc R U . . .
H26C H 0.436313 0.694162 1.046004 0.047 Uiso 1 1 calc R U . . .
C27 C 0.3652(2) 0.64572(13) 0.8753(3) 0.0311(8) Uani 1 1 d . . . . .
H27A H 0.347169 0.686264 0.875253 0.047 Uiso 1 1 calc R U . . .
H27B H 0.308977 0.622349 0.883478 0.047 Uiso 1 1 calc R U . . .
H27C H 0.377393 0.636011 0.816568 0.047 Uiso 1 1 calc R U . . .
C22 C 0.7011(3) 0.61433(13) 1.0875(2) 0.0292(7) Uani 1 1 d . . . . .
H22A H 0.641083 0.605911 1.108217 0.044 Uiso 1 1 calc R U . . .
H22B H 0.762252 0.615688 1.140749 0.044 Uiso 1 1 calc R U . . .
H22C H 0.709284 0.584370 1.045088 0.044 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
I1 Pd1 2.7678(2) . ?
I1 Pd2 2.7441(2) . ?
Pd1 Pd2 2.6215(3) . ?
Pd1 P1 2.2491(7) . ?
Pd1 P2 2.3494(7) . ?
Pd2 P1 2.2157(6) . ?
Pd2 P3 2.3467(7) . ?
P1 N1 1.701(2) . ?
P1 C1 1.804(2) . ?
P3 C40 1.906(3) . ?
P3 C32 1.915(3) . ?
P3 C36 1.903(3) . ?
P2 C28 1.919(3) . ?
P2 C20 1.919(3) . ?
P2 C24 1.916(3) . ?
N1 C8 1.445(3) . ?
N1 C7 1.483(3) . ?
C8 C13 1.417(4) . ?
C8 C9 1.405(4) . ?
C13 C17 1.530(4) . ?
C13 C12 1.398(4) . ?
C28 C29 1.528(4) . ?
C28 C31 1.531(4) . ?
C28 C30 1.536(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.499(4) . ?
C9 C10 1.399(4) . ?
C9 C14 1.526(4) . ?
C1 C6 1.394(4) . ?
C1 C2 1.392(4) . ?
C40 C43 1.534(4) . ?
C40 C41 1.544(4) . ?
C40 C42 1.545(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.377(4) . ?
C32 C35 1.543(4) . ?
C32 C33 1.539(4) . ?
C32 C34 1.541(4) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C17 H17 1.0000 . ?
C17 C19 1.547(4) . ?
C17 C18 1.531(4) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C6 C5 1.397(3) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C11 1.395(4) . ?
C11 H11 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.387(3) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C3 1.393(4) . ?
C4 C5 1.388(4) . ?
C36 C38 1.540(4) . ?
C36 C39 1.546(4) . ?
C36 C37 1.539(4) . ?
C20 C21 1.545(4) . ?
C20 C23 1.547(4) . ?
C20 C22 1.543(4) . ?
C3 H3 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C24 C25 1.549(4) . ?
C24 C26 1.541(4) . ?
C24 C27 1.530(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C14 H14 1.0000 . ?
C14 C15 1.529(4) . ?
C14 C16 1.536(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C5 H5 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
Pd2 I1 Pd1 56.795(6) . . ?
Pd2 Pd1 I1 61.146(6) . . ?
P1 Pd1 I1 113.708(17) . . ?
P1 Pd1 Pd2 53.457(17) . . ?
P1 Pd1 P2 124.20(2) . . ?
P2 Pd1 I1 119.846(19) . . ?
P2 Pd1 Pd2 156.989(19) . . ?
Pd1 Pd2 I1 62.059(7) . . ?
P1 Pd2 I1 115.765(19) . . ?
P1 Pd2 Pd1 54.638(18) . . ?
P1 Pd2 P3 125.40(2) . . ?
P3 Pd2 I1 118.288(17) . . ?
P3 Pd2 Pd1 163.728(19) . . ?
Pd2 P1 Pd1 71.90(2) . . ?
N1 P1 Pd1 127.58(8) . . ?
N1 P1 Pd2 130.52(8) . . ?
N1 P1 C1 89.72(11) . . ?
C1 P1 Pd1 117.04(9) . . ?
C1 P1 Pd2 124.05(9) . . ?
C40 P3 Pd2 108.24(8) . . ?
C40 P3 C32 108.26(12) . . ?
C32 P3 Pd2 113.81(8) . . ?
C36 P3 Pd2 111.02(9) . . ?
C36 P3 C40 108.29(12) . . ?
C36 P3 C32 107.06(12) . . ?
C28 P2 Pd1 115.20(9) . . ?
C28 P2 C20 107.93(13) . . ?
C20 P2 Pd1 104.70(9) . . ?
C24 P2 Pd1 114.37(9) . . ?
C24 P2 C28 106.78(12) . . ?
C24 P2 C20 107.45(14) . . ?
C8 N1 P1 126.95(16) . . ?
C8 N1 C7 117.2(2) . . ?
C7 N1 P1 115.65(17) . . ?
C13 C8 N1 119.2(2) . . ?
C9 C8 N1 120.5(2) . . ?
C9 C8 C13 120.2(2) . . ?
C8 C13 C17 124.8(2) . . ?
C12 C13 C8 118.6(2) . . ?
C12 C13 C17 116.6(2) . . ?
C29 C28 P2 109.29(19) . . ?
C29 C28 C31 107.8(2) . . ?
C29 C28 C30 105.4(2) . . ?
C31 C28 P2 115.8(2) . . ?
C31 C28 C30 109.2(2) . . ?
C30 C28 P2 108.75(18) . . ?
N1 C7 H7A 110.6 . . ?
N1 C7 H7B 110.6 . . ?
N1 C7 C6 105.9(2) . . ?
H7A C7 H7B 108.7 . . ?
C6 C7 H7A 110.6 . . ?
C6 C7 H7B 110.6 . . ?
C8 C9 C14 123.6(2) . . ?
C10 C9 C8 118.6(3) . . ?
C10 C9 C14 117.5(2) . . ?
C6 C1 P1 112.32(19) . . ?
C2 C1 P1 127.5(2) . . ?
C2 C1 C6 120.1(2) . . ?
C43 C40 P3 108.21(17) . . ?
C43 C40 C41 109.0(2) . . ?
C43 C40 C42 105.3(2) . . ?
C41 C40 P3 117.04(19) . . ?
C41 C40 C42 108.6(2) . . ?
C42 C40 P3 108.05(18) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 122.0(3) . . ?
C11 C10 H10 119.0 . . ?
C35 C32 P3 107.73(17) . . ?
C33 C32 P3 116.34(17) . . ?
C33 C32 C35 108.3(2) . . ?
C33 C32 C34 108.4(2) . . ?
C34 C32 P3 110.12(19) . . ?
C34 C32 C35 105.5(2) . . ?
C40 C43 H43A 109.5 . . ?
C40 C43 H43B 109.5 . . ?
C40 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C13 C17 H17 108.4 . . ?
C13 C17 C19 111.7(2) . . ?
C13 C17 C18 112.1(2) . . ?
C19 C17 H17 108.4 . . ?
C18 C17 H17 108.4 . . ?
C18 C17 C19 107.6(2) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C1 C6 C7 113.6(2) . . ?
C1 C6 C5 120.6(3) . . ?
C5 C6 C7 125.8(2) . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C13 C12 H12 119.3 . . ?
C11 C12 C13 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C10 C11 C12 119.0(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 121.0(2) . . ?
C38 C36 P3 116.0(2) . . ?
C38 C36 C39 107.3(2) . . ?
C39 C36 P3 109.68(19) . . ?
C37 C36 P3 107.95(18) . . ?
C37 C36 C38 109.3(2) . . ?
C37 C36 C39 106.3(2) . . ?
C21 C20 P2 108.5(2) . . ?
C21 C20 C23 108.3(2) . . ?
C23 C20 P2 116.8(2) . . ?
C22 C20 P2 110.0(2) . . ?
C22 C20 C21 104.9(3) . . ?
C22 C20 C23 107.8(2) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C25 C24 P2 107.69(19) . . ?
C26 C24 P2 117.1(2) . . ?
C26 C24 C25 108.5(3) . . ?
C27 C24 P2 109.1(2) . . ?
C27 C24 C25 105.7(2) . . ?
C27 C24 C26 108.2(3) . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C14 H14 108.1 . . ?
C9 C14 C15 113.0(2) . . ?
C9 C14 C16 108.7(2) . . ?
C15 C14 H14 108.1 . . ?
C15 C14 C16 110.7(2) . . ?
C16 C14 H14 108.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C6 C5 H5 120.7 . . ?
C4 C5 C6 118.6(3) . . ?
C4 C5 H5 120.7 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
Pd1 P1 N1 C8 -66.6(2) . . . . ?
Pd1 P1 N1 C7 108.33(18) . . . . ?
Pd1 P1 C1 C6 -121.57(18) . . . . ?
Pd1 P1 C1 C2 54.5(3) . . . . ?
Pd2 P1 N1 C8 31.6(3) . . . . ?
Pd2 P1 N1 C7 -153.50(15) . . . . ?
Pd2 P1 C1 C6 152.79(15) . . . . ?
Pd2 P1 C1 C2 -31.1(3) . . . . ?
P1 N1 C8 C13 -115.8(2) . . . . ?
P1 N1 C8 C9 67.8(3) . . . . ?
P1 N1 C7 C6 16.6(3) . . . . ?
P1 C1 C6 C7 -3.9(3) . . . . ?
P1 C1 C6 C5 175.9(2) . . . . ?
P1 C1 C2 C3 -175.2(2) . . . . ?
N1 P1 C1 C6 11.4(2) . . . . ?
N1 P1 C1 C2 -172.4(2) . . . . ?
N1 C8 C13 C17 0.9(4) . . . . ?
N1 C8 C13 C12 -178.6(2) . . . . ?
N1 C8 C9 C10 179.8(2) . . . . ?
N1 C8 C9 C14 6.0(4) . . . . ?
N1 C7 C6 C1 -7.3(3) . . . . ?
N1 C7 C6 C5 172.9(3) . . . . ?
C8 N1 C7 C6 -167.9(2) . . . . ?
C8 C13 C17 C19 -105.1(3) . . . . ?
C8 C13 C17 C18 134.1(3) . . . . ?
C8 C13 C12 C11 -0.5(4) . . . . ?
C8 C9 C10 C11 -2.1(4) . . . . ?
C8 C9 C14 C15 -134.6(3) . . . . ?
C8 C9 C14 C16 102.1(3) . . . . ?
C13 C8 C9 C10 3.4(4) . . . . ?
C13 C8 C9 C14 -170.4(2) . . . . ?
C13 C12 C11 C10 1.8(4) . . . . ?
C7 N1 C8 C13 69.4(3) . . . . ?
C7 N1 C8 C9 -107.1(3) . . . . ?
C7 C6 C5 C4 179.9(3) . . . . ?
C9 C8 C13 C17 177.3(2) . . . . ?
C9 C8 C13 C12 -2.1(4) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C1 P1 N1 C8 168.7(2) . . . . ?
C1 P1 N1 C7 -16.4(2) . . . . ?
C1 C6 C5 C4 0.1(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C10 C9 C14 C15 51.6(3) . . . . ?
C10 C9 C14 C16 -71.8(3) . . . . ?
C17 C13 C12 C11 180.0(2) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C12 C13 C17 C19 74.4(3) . . . . ?
C12 C13 C17 C18 -46.5(3) . . . . ?
C2 C1 C6 C7 179.7(2) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C14 C9 C10 C11 172.1(2) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?

_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_cain83_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc250y05
_database_code_depnum_ccdc_archive 'CCDC 1996896'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0DT01367F 2020
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2020-12-19 deposited with the CCDC.	2021-01-05 downloaded from the CCDC.
;
_audit_creation_date             2019-10-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H23 Cl0.25 I0.75 N P'
_chemical_formula_sum            'C19 H23 Cl0.25 I0.75 N P'
_chemical_formula_weight         400.39
_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'
I I -0.4742 1.8119 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4221(5)
_cell_length_b                   9.8317(8)
_cell_length_c                   20.1049(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.724(3)
_cell_angle_gamma                90
_cell_volume                     1823.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1719
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   0.740
_shelx_estimated_absorpt_T_min   0.713
_exptl_absorpt_coefficient_mu    1.454
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0759 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.9065.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16478
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.345
_diffrn_reflns_theta_min         2.069
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4004
_reflns_number_total             4539
_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       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         4539
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.154
_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)+(0.0147P)²+1.6457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0635
_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. Uiso/Uaniso restraints and constraints
Uanis(I1) = Uanis(Cl1)
3. Others
 Sof(Cl1)=1-FVAR(1)
 Sof(I1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C14(H14), C17(H17)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12)
4.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I1 I 0.77243(5) 0.39402(4) 0.50057(2) 0.02007(8) Uani 0.749(2) 1 d . . P A 1
Cl1 Cl 0.7701(7) 0.4151(5) 0.4899(3) 0.02007(8) Uani 0.251(2) 1 d . . P A 2
P1 P 0.63697(6) 0.54129(6) 0.40054(3) 0.01728(14) Uani 1 1 d . . . . .
N1 N 0.74682(19) 0.56643(17) 0.34640(8) 0.0147(4) Uani 1 1 d . . . . .
C1 C 0.6860(2) 0.7061(2) 0.43854(10) 0.0171(4) Uani 1 1 d . . . . .
C2 C 0.6252(3) 0.7727(2) 0.48750(11) 0.0230(5) Uani 1 1 d . . . . .
H2 H 0.552279 0.730202 0.506688 0.028 Uiso 1 1 calc R . . . .
C3 C 0.6743(3) 0.9030(2) 0.50740(12) 0.0267(5) Uani 1 1 d . . . . .
H3 H 0.633296 0.950376 0.540135 0.032 Uiso 1 1 calc R . . . .
C4 C 0.7820(3) 0.9647(2) 0.48019(12) 0.0268(5) Uani 1 1 d . . . . .
H4 H 0.813942 1.053648 0.494368 0.032 Uiso 1 1 calc R . . . .
C5 C 0.8436(3) 0.8970(2) 0.43227(11) 0.0224(5) Uani 1 1 d . . . . .
H5 H 0.918714 0.938366 0.414220 0.027 Uiso 1 1 calc R . . . .
C6 C 0.7936(2) 0.7681(2) 0.41124(10) 0.0170(4) Uani 1 1 d . . . . .
C7 C 0.8439(2) 0.6849(2) 0.35780(10) 0.0170(4) Uani 1 1 d . . . . .
H7A H 0.836738 0.738046 0.315420 0.020 Uiso 1 1 calc R . . . .
H7B H 0.945710 0.655820 0.373680 0.020 Uiso 1 1 calc R . . . .
C8 C 0.7474(2) 0.4820(2) 0.28787(10) 0.0149(4) Uani 1 1 d . . . . .
C9 C 0.8603(2) 0.3881(2) 0.28846(10) 0.0172(4) Uani 1 1 d . . . . .
C10 C 0.8576(3) 0.3100(2) 0.23039(12) 0.0231(5) Uani 1 1 d . . . . .
H10 H 0.933986 0.247419 0.229457 0.028 Uiso 1 1 calc R . . . .
C11 C 0.7466(3) 0.3214(2) 0.17422(11) 0.0260(5) Uani 1 1 d . . . . .
H11 H 0.746174 0.266321 0.135378 0.031 Uiso 1 1 calc R . . . .
C12 C 0.6357(3) 0.4135(2) 0.17469(11) 0.0214(5) Uani 1 1 d . . . . .
H12 H 0.558732 0.419937 0.136131 0.026 Uiso 1 1 calc R . . . .
C13 C 0.6347(2) 0.4973(2) 0.23066(10) 0.0158(4) Uani 1 1 d . . . . .
C14 C 0.9810(2) 0.3664(2) 0.34997(11) 0.0203(5) Uani 1 1 d . . . . .
H14 H 0.963673 0.428596 0.386871 0.024 Uiso 1 1 calc R . . . .
C15 C 1.1283(3) 0.4012(3) 0.33411(14) 0.0308(6) Uani 1 1 d . . . . .
H15A H 1.148982 0.339300 0.299056 0.046 Uiso 1 1 calc GR . . . .
H15B H 1.203521 0.391498 0.375370 0.046 Uiso 1 1 calc GR . . . .
H15C H 1.127174 0.495126 0.317696 0.046 Uiso 1 1 calc GR . . . .
C16 C 0.9805(3) 0.2201(2) 0.37580(14) 0.0307(6) Uani 1 1 d . . . . .
H16A H 1.009900 0.158199 0.342841 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.882725 0.196189 0.381577 0.046 Uiso 1 1 calc GR . . . .
H16C H 1.048479 0.212053 0.419515 0.046 Uiso 1 1 calc GR . . . .
C17 C 0.5111(2) 0.5968(2) 0.22799(10) 0.0180(4) Uani 1 1 d . . . . .
H17 H 0.537389 0.660144 0.267486 0.022 Uiso 1 1 calc R . . . .
C18 C 0.3738(3) 0.5195(3) 0.23541(12) 0.0252(5) Uani 1 1 d . . . . .
H18A H 0.348539 0.453607 0.198320 0.038 Uiso 1 1 calc GR . . . .
H18B H 0.293849 0.584002 0.233610 0.038 Uiso 1 1 calc GR . . . .
H18C H 0.391418 0.471512 0.279033 0.038 Uiso 1 1 calc GR . . . .
C19 C 0.4823(3) 0.6822(2) 0.16285(12) 0.0243(5) Uani 1 1 d . . . . .
H19A H 0.572555 0.725993 0.157181 0.037 Uiso 1 1 calc GR . . . .
H19B H 0.409708 0.751989 0.165974 0.037 Uiso 1 1 calc GR . . . .
H19C H 0.446367 0.623234 0.123763 0.037 Uiso 1 1 calc GR . . . .


_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
I1 P1 2.5937(7) . ?
Cl1 P1 2.329(5) . ?
P1 N1 1.6657(17) . ?
P1 C1 1.811(2) . ?
N1 C7 1.470(3) . ?
N1 C8 1.441(2) . ?
C1 C2 1.398(3) . ?
C1 C6 1.388(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C6 C7 1.501(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.407(3) . ?
C8 C13 1.405(3) . ?
C9 C10 1.393(3) . ?
C9 C14 1.515(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.396(3) . ?
C13 C17 1.514(3) . ?
C14 H14 1.0000 . ?
C14 C15 1.525(3) . ?
C14 C16 1.530(3) . ?
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 H17 1.0000 . ?
C17 C18 1.533(3) . ?
C17 C19 1.533(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
N1 P1 I1 108.43(7) . . ?
N1 P1 Cl1 105.93(17) . . ?
N1 P1 C1 90.23(9) . . ?
C1 P1 I1 97.42(7) . . ?
C1 P1 Cl1 95.74(16) . . ?
C7 N1 P1 117.72(13) . . ?
C8 N1 P1 123.64(14) . . ?
C8 N1 C7 118.59(16) . . ?
C2 C1 P1 127.62(18) . . ?
C6 C1 P1 111.72(15) . . ?
C6 C1 C2 120.6(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 113.95(18) . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 C7 125.3(2) . . ?
N1 C7 C6 105.45(16) . . ?
N1 C7 H7A 110.7 . . ?
N1 C7 H7B 110.7 . . ?
C6 C7 H7A 110.7 . . ?
C6 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C9 C8 N1 119.95(19) . . ?
C13 C8 N1 118.64(18) . . ?
C13 C8 C9 121.39(18) . . ?
C8 C9 C14 122.69(18) . . ?
C10 C9 C8 118.0(2) . . ?
C10 C9 C14 119.28(19) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.5(2) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.3(2) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C17 123.07(18) . . ?
C12 C13 C8 117.99(19) . . ?
C12 C13 C17 118.9(2) . . ?
C9 C14 H14 108.1 . . ?
C9 C14 C15 111.21(19) . . ?
C9 C14 C16 110.8(2) . . ?
C15 C14 H14 108.1 . . ?
C15 C14 C16 110.3(2) . . ?
C16 C14 H14 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17 108.0 . . ?
C13 C17 C18 109.54(18) . . ?
C13 C17 C19 112.68(17) . . ?
C18 C17 H17 108.0 . . ?
C19 C17 H17 108.0 . . ?
C19 C17 C18 110.41(19) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_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_cain92_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc26vykl
_database_code_depnum_ccdc_archive 'CCDC 2051690'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0DT01367F 2020
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2020-12-19 deposited with the CCDC.	2021-01-05 downloaded from the CCDC.
;
_audit_creation_date             2020-08-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H46 N2 O0.38 P2'
_chemical_formula_sum            'C38 H46 N2 O0.38 P2'
_chemical_formula_weight         598.87
_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'
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                   11.6914(5)
_cell_length_b                   12.0731(5)
_cell_length_c                   13.1054(6)
_cell_angle_alpha                95.100(2)
_cell_angle_beta                 94.213(2)
_cell_angle_gamma                113.203(2)
_cell_volume                     1681.56(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4609
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.59
_cell_measurement_theta_min      9.89
_shelx_estimated_absorpt_T_max   0.697
_shelx_estimated_absorpt_T_min   0.673
_exptl_absorpt_coefficient_mu    1.388
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0613 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.8789.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             642
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15973
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.328
_diffrn_reflns_theta_min         3.410
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5452
_reflns_number_total             6003
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6003
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.038
_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)+(0.0512P)²+0.6308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0976
_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 Ternary CH refined with riding coordinates:
 C14(H14), C17(H17), C33(H33), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C21(H21), C22(H22), C5(H5), C29(H29), C2(H2), C30(H30), C4(H4),
 C12(H12), C23(H23), C31(H31), C11(H11), C24(H24), C3(H3)
2.d Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C), C19(H19A,H19B,H19C), C16(H16A,H16B,H16C), C15(H15A,H15B,
 H15C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C18(H18A,H18B,H18C), C34(H34A,
 H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
P2 P 0.53298(3) 0.44471(3) 0.70843(3) 0.01445(10) Uani 1 1 d . . . . .
P1 P 0.70496(3) 0.46470(3) 0.81496(3) 0.01845(11) Uani 1 1 d . . . . .
N2 N 0.41385(11) 0.35091(10) 0.76809(9) 0.0144(2) Uani 1 1 d . . . . .
N1 N 0.79812(11) 0.42615(11) 0.73851(9) 0.0149(2) Uani 1 1 d . . . . .
C27 C 0.32743(12) 0.23551(12) 0.71539(10) 0.0140(3) Uani 1 1 d . . . . .
C25 C 0.42477(13) 0.54426(13) 0.83788(11) 0.0172(3) Uani 1 1 d . . . . .
C28 C 0.24429(13) 0.22964(13) 0.62925(10) 0.0160(3) Uani 1 1 d . . . . .
C8 C 0.79426(13) 0.30550(13) 0.72131(11) 0.0150(3) Uani 1 1 d . . . . .
C20 C 0.50940(13) 0.57659(13) 0.76489(11) 0.0158(3) Uani 1 1 d . . . . .
C10 C 0.73499(14) 0.11541(14) 0.61205(12) 0.0216(3) Uani 1 1 d . . . . .
H10 H 0.696515 0.064849 0.548719 0.026 Uiso 1 1 calc R . . . .
C21 C 0.55909(14) 0.69510(13) 0.74053(12) 0.0205(3) Uani 1 1 d . . . . .
H21 H 0.617017 0.716913 0.691071 0.025 Uiso 1 1 calc R . . . .
C9 C 0.73600(13) 0.23195(13) 0.62677(11) 0.0169(3) Uani 1 1 d . . . . .
C13 C 0.85064(13) 0.26304(13) 0.79872(11) 0.0170(3) Uani 1 1 d . . . . .
C6 C 0.90017(13) 0.64140(13) 0.75630(10) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.80604(13) 0.62430(13) 0.82009(11) 0.0165(3) Uani 1 1 d . . . . .
C7 C 0.90023(14) 0.52589(13) 0.70297(11) 0.0173(3) Uani 1 1 d . . . . .
H7A H 0.886319 0.522974 0.627165 0.021 Uiso 1 1 calc R . . . .
H7B H 0.981384 0.520472 0.721211 0.021 Uiso 1 1 calc R . . . .
C14 C 0.67661(14) 0.27634(14) 0.54133(11) 0.0194(3) Uani 1 1 d . . . . .
H14 H 0.676089 0.355845 0.569551 0.023 Uiso 1 1 calc R . . . .
C32 C 0.32858(13) 0.12895(13) 0.75042(11) 0.0156(3) Uani 1 1 d . . . . .
C22 C 0.52302(15) 0.78110(14) 0.78935(13) 0.0254(3) Uani 1 1 d . . . . .
H22 H 0.555777 0.861988 0.772814 0.030 Uiso 1 1 calc R . . . .
C5 C 0.98474(15) 0.75862(14) 0.74683(12) 0.0217(3) Uani 1 1 d . . . . .
H5 H 1.047983 0.770793 0.702260 0.026 Uiso 1 1 calc R . . . .
C29 C 0.16948(14) 0.11558(14) 0.57490(11) 0.0199(3) Uani 1 1 d . . . . .
H29 H 0.114199 0.110030 0.515944 0.024 Uiso 1 1 calc R . . . .
C26 C 0.37667(14) 0.41167(13) 0.85367(11) 0.0188(3) Uani 1 1 d . . . . .
H26A H 0.414290 0.402257 0.920773 0.023 Uiso 1 1 calc R . . . .
H26B H 0.284360 0.376716 0.852322 0.023 Uiso 1 1 calc R . . . .
C2 C 0.79868(14) 0.72396(14) 0.87813(11) 0.0204(3) Uani 1 1 d . . . . .
H2 H 0.735879 0.712138 0.923085 0.024 Uiso 1 1 calc R . . . .
C30 C 0.17449(14) 0.01051(14) 0.60542(11) 0.0216(3) Uani 1 1 d . . . . .
H30 H 0.124845 -0.066037 0.566367 0.026 Uiso 1 1 calc R . . . .
C17 C 0.91973(14) 0.34234(14) 0.89943(11) 0.0199(3) Uani 1 1 d . . . . .
H17 H 0.907495 0.419895 0.901178 0.024 Uiso 1 1 calc R . . . .
C4 C 0.97593(15) 0.85776(14) 0.80310(12) 0.0244(3) Uani 1 1 d . . . . .
H4 H 1.032828 0.937862 0.796359 0.029 Uiso 1 1 calc R . . . .
C12 C 0.84632(14) 0.14554(14) 0.78042(12) 0.0221(3) Uani 1 1 d . . . . .
H12 H 0.883252 0.115444 0.832143 0.027 Uiso 1 1 calc R . . . .
C23 C 0.43927(16) 0.74900(15) 0.86216(13) 0.0273(4) Uani 1 1 d . . . . .
H23 H 0.414969 0.808307 0.895048 0.033 Uiso 1 1 calc R . . . .
C33 C 0.23321(14) 0.34212(13) 0.59429(11) 0.0189(3) Uani 1 1 d . . . . .
H33 H 0.284156 0.412714 0.647447 0.023 Uiso 1 1 calc R . . . .
C35 C 0.09725(14) 0.33088(15) 0.58623(12) 0.0242(3) Uani 1 1 d . . . . .
H35A H 0.046924 0.267891 0.529463 0.036 Uiso 1 1 calc GR . . . .
H35B H 0.095255 0.408773 0.573046 0.036 Uiso 1 1 calc GR . . . .
H35C H 0.062812 0.308791 0.651033 0.036 Uiso 1 1 calc GR . . . .
C31 C 0.25213(14) 0.01729(13) 0.69313(11) 0.0192(3) Uani 1 1 d . . . . .
H31 H 0.253354 -0.055359 0.714655 0.023 Uiso 1 1 calc R . . . .
C19 C 0.86817(16) 0.28230(16) 0.99383(12) 0.0278(4) Uani 1 1 d . . . . .
H19A H 0.777452 0.259325 0.988246 0.042 Uiso 1 1 calc GR . . . .
H19B H 0.908495 0.339567 1.056507 0.042 Uiso 1 1 calc GR . . . .
H19C H 0.885558 0.209567 0.997147 0.042 Uiso 1 1 calc GR . . . .
C36 C 0.40728(14) 0.13233(13) 0.84906(11) 0.0196(3) Uani 1 1 d . . . . .
H36 H 0.453681 0.219153 0.879778 0.024 Uiso 1 1 calc R . . . .
C16 C 0.54059(15) 0.18813(16) 0.50565(13) 0.0274(4) Uani 1 1 d . . . . .
H16A H 0.538951 0.111448 0.472405 0.041 Uiso 1 1 calc GR . . . .
H16B H 0.502476 0.223845 0.456353 0.041 Uiso 1 1 calc GR . . . .
H16C H 0.493370 0.172707 0.565369 0.041 Uiso 1 1 calc GR . . . .
C11 C 0.78899(15) 0.07217(14) 0.68797(13) 0.0240(3) Uani 1 1 d . . . . .
H11 H 0.786737 -0.007523 0.676727 0.029 Uiso 1 1 calc R . . . .
C24 C 0.39029(15) 0.63096(14) 0.88774(12) 0.0239(3) Uani 1 1 d . . . . .
H24 H 0.334089 0.609974 0.938554 0.029 Uiso 1 1 calc R . . . .
C15 C 0.75372(16) 0.29809(15) 0.44962(12) 0.0253(3) Uani 1 1 d . . . . .
H15A H 0.839857 0.356037 0.473335 0.038 Uiso 1 1 calc GR . . . .
H15B H 0.716268 0.331074 0.397408 0.038 Uiso 1 1 calc GR . . . .
H15C H 0.754277 0.221048 0.419563 0.038 Uiso 1 1 calc GR . . . .
C3 C 0.88422(15) 0.84002(14) 0.86911(12) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.880152 0.908114 0.908417 0.027 Uiso 1 1 calc R . . . .
C37 C 0.32224(17) 0.06470(18) 0.92672(13) 0.0342(4) Uani 1 1 d . . . . .
H37A H 0.259934 0.098696 0.937715 0.051 Uiso 1 1 calc GR . . . .
H37B H 0.372977 0.073848 0.992356 0.051 Uiso 1 1 calc GR . . . .
H37C H 0.279429 -0.021695 0.899772 0.051 Uiso 1 1 calc GR . . . .
C38 C 0.50333(16) 0.07921(16) 0.82767(14) 0.0303(4) Uani 1 1 d . . . . .
H38A H 0.459914 -0.004794 0.794285 0.045 Uiso 1 1 calc GR . . . .
H38B H 0.550990 0.080601 0.892839 0.045 Uiso 1 1 calc GR . . . .
H38C H 0.560714 0.127730 0.782148 0.045 Uiso 1 1 calc GR . . . .
C18 C 1.06045(14) 0.37387(15) 0.90309(12) 0.0245(3) Uani 1 1 d . . . . .
H18A H 1.074969 0.299181 0.901688 0.037 Uiso 1 1 calc GR . . . .
H18B H 1.104409 0.427981 0.966644 0.037 Uiso 1 1 calc GR . . . .
H18C H 1.092005 0.414621 0.843294 0.037 Uiso 1 1 calc GR . . . .
C34 C 0.28663(16) 0.36890(16) 0.49160(13) 0.0278(4) Uani 1 1 d . . . . .
H34A H 0.373074 0.375144 0.497867 0.042 Uiso 1 1 calc GR . . . .
H34B H 0.285422 0.445694 0.474061 0.042 Uiso 1 1 calc GR . . . .
H34C H 0.235578 0.302987 0.437180 0.042 Uiso 1 1 calc GR . . . .
O1 O 0.6733(2) 0.4146(2) 0.89894(19) 0.0190(10) Uani 0.382(5) 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
P2 P1 2.2793(5) . ?
P2 N2 1.7053(12) . ?
P2 C20 1.8235(14) . ?
P1 N1 1.6981(12) . ?
P1 C1 1.8124(15) . ?
P1 O1 1.310(2) . ?
N2 C27 1.4340(18) . ?
N2 C26 1.4702(18) . ?
N1 C8 1.4363(18) . ?
N1 C7 1.4631(18) . ?
C27 C28 1.4123(19) . ?
C27 C32 1.4085(19) . ?
C25 C20 1.395(2) . ?
C25 C26 1.513(2) . ?
C25 C24 1.391(2) . ?
C28 C29 1.398(2) . ?
C28 C33 1.5203(19) . ?
C8 C9 1.411(2) . ?
C8 C13 1.410(2) . ?
C20 C21 1.393(2) . ?
C10 H10 0.9500 . ?
C10 C9 1.398(2) . ?
C10 C11 1.386(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(2) . ?
C9 C14 1.520(2) . ?
C13 C17 1.523(2) . ?
C13 C12 1.398(2) . ?
C6 C1 1.393(2) . ?
C6 C7 1.5036(19) . ?
C6 C5 1.394(2) . ?
C1 C2 1.401(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C14 H14 1.0000 . ?
C14 C16 1.533(2) . ?
C14 C15 1.535(2) . ?
C32 C31 1.397(2) . ?
C32 C36 1.5185(19) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.392(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.385(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.387(2) . ?
C17 H17 1.0000 . ?
C17 C19 1.531(2) . ?
C17 C18 1.531(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.390(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.387(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.393(2) . ?
C33 H33 1.0000 . ?
C33 C35 1.536(2) . ?
C33 C34 1.532(2) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C31 H31 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C36 H36 1.0000 . ?
C36 C37 1.532(2) . ?
C36 C38 1.527(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C11 H11 0.9500 . ?
C24 H24 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C3 H3 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
N2 P2 P1 101.90(4) . . ?
N2 P2 C20 90.64(6) . . ?
C20 P2 P1 99.23(5) . . ?
N1 P1 P2 105.89(4) . . ?
N1 P1 C1 90.58(6) . . ?
C1 P1 P2 102.93(5) . . ?
O1 P1 P2 111.38(12) . . ?
O1 P1 N1 121.29(12) . . ?
O1 P1 C1 121.64(13) . . ?
C27 N2 P2 120.58(9) . . ?
C27 N2 C26 120.15(11) . . ?
C26 N2 P2 115.06(9) . . ?
C8 N1 P1 123.52(9) . . ?
C8 N1 C7 118.87(11) . . ?
C7 N1 P1 116.84(9) . . ?
C28 C27 N2 120.30(12) . . ?
C32 C27 N2 118.69(12) . . ?
C32 C27 C28 121.01(13) . . ?
C20 C25 C26 114.24(12) . . ?
C24 C25 C20 120.01(14) . . ?
C24 C25 C26 125.74(14) . . ?
C27 C28 C33 122.49(13) . . ?
C29 C28 C27 118.24(13) . . ?
C29 C28 C33 119.28(12) . . ?
C9 C8 N1 119.67(12) . . ?
C13 C8 N1 119.37(12) . . ?
C13 C8 C9 120.95(13) . . ?
C25 C20 P2 110.73(11) . . ?
C21 C20 P2 128.64(11) . . ?
C21 C20 C25 120.57(13) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C11 C10 C9 121.33(14) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.30(14) . . ?
C22 C21 H21 120.4 . . ?
C8 C9 C14 122.01(12) . . ?
C10 C9 C8 118.25(13) . . ?
C10 C9 C14 119.74(13) . . ?
C8 C13 C17 122.22(13) . . ?
C12 C13 C8 118.54(13) . . ?
C12 C13 C17 119.21(13) . . ?
C1 C6 C7 114.47(13) . . ?
C1 C6 C5 119.92(14) . . ?
C5 C6 C7 125.60(13) . . ?
C6 C1 P1 111.37(10) . . ?
C6 C1 C2 120.43(14) . . ?
C2 C1 P1 128.20(12) . . ?
N1 C7 C6 106.34(11) . . ?
N1 C7 H7A 110.5 . . ?
N1 C7 H7B 110.5 . . ?
C6 C7 H7A 110.5 . . ?
C6 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C9 C14 H14 107.8 . . ?
C9 C14 C16 111.76(13) . . ?
C9 C14 C15 111.07(12) . . ?
C16 C14 H14 107.8 . . ?
C16 C14 C15 110.42(12) . . ?
C15 C14 H14 107.8 . . ?
C27 C32 C36 122.00(13) . . ?
C31 C32 C27 118.26(13) . . ?
C31 C32 C36 119.72(13) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.10(15) . . ?
C23 C22 H22 119.9 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.57(14) . . ?
C4 C5 H5 120.2 . . ?
C28 C29 H29 119.4 . . ?
C30 C29 C28 121.20(13) . . ?
C30 C29 H29 119.4 . . ?
N2 C26 C25 105.93(11) . . ?
N2 C26 H26A 110.6 . . ?
N2 C26 H26B 110.6 . . ?
C25 C26 H26A 110.6 . . ?
C25 C26 H26B 110.6 . . ?
H26A C26 H26B 108.7 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.12(14) . . ?
C3 C2 H2 120.4 . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.85(14) . . ?
C31 C30 H30 120.1 . . ?
C13 C17 H17 107.9 . . ?
C13 C17 C19 112.03(13) . . ?
C13 C17 C18 110.16(12) . . ?
C19 C17 H17 107.9 . . ?
C19 C17 C18 110.84(12) . . ?
C18 C17 H17 107.9 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.28(14) . . ?
C3 C4 H4 119.9 . . ?
C13 C12 H12 119.5 . . ?
C11 C12 C13 121.08(14) . . ?
C11 C12 H12 119.5 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.90(14) . . ?
C24 C23 H23 119.6 . . ?
C28 C33 H33 107.7 . . ?
C28 C33 C35 111.77(12) . . ?
C28 C33 C34 111.16(12) . . ?
C35 C33 H33 107.7 . . ?
C34 C33 H33 107.7 . . ?
C34 C33 C35 110.50(12) . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C32 C31 H31 119.4 . . ?
C30 C31 C32 121.25(13) . . ?
C30 C31 H31 119.4 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C32 C36 H36 108.1 . . ?
C32 C36 C37 109.99(12) . . ?
C32 C36 C38 111.40(13) . . ?
C37 C36 H36 108.1 . . ?
C38 C36 H36 108.1 . . ?
C38 C36 C37 110.90(13) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C11 C12 119.84(14) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C25 C24 C23 119.12(15) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C3 C4 120.62(14) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

_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_cain89_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc26vyhj
_database_code_depnum_ccdc_archive 'CCDC 2051688'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0DT01367F 2020
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2020-12-19 deposited with the CCDC.	2021-01-05 downloaded from the CCDC.
;
_audit_creation_date             2020-06-18
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H30 N P'
_chemical_formula_sum            'C26 H30 N P'
_chemical_formula_weight         387.48
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1766(2)
_cell_length_b                   20.7413(4)
_cell_length_c                   11.3263(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.8390(10)
_cell_angle_gamma                90
_cell_volume                     2248.82(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3379
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      4.62
_shelx_estimated_absorpt_T_max   0.857
_shelx_estimated_absorpt_T_min   0.712
_exptl_absorpt_coefficient_mu    1.140
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0507 before and 0.0380 after correction.
The Ratio of minimum to maximum transmission is 0.8663.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12696
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.474
_diffrn_reflns_theta_min         4.263
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3776
_reflns_number_total             4100
_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       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.059
_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)+(0.0514P)²+0.8380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0954
_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 Ternary CH refined with riding coordinates:
 C21(H21), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C9(H9), C13(H13), C4(H4), C12(H12), C3(H3), C17(H17),
 C10(H10), C19(H19), C18(H18)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,
 H25C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.52330(3) 0.67320(2) 0.53048(3) 0.01586(11) Uani 1 1 d . . . . .
N1 N 0.42839(10) 0.69033(5) 0.62507(9) 0.0165(2) Uani 1 1 d . . . . .
C8 C 0.65401(12) 0.61288(6) 0.61595(12) 0.0174(3) Uani 1 1 d . . . . .
C5 C 0.64728(14) 0.83692(6) 0.72528(13) 0.0213(3) Uani 1 1 d . . . . .
H5 H 0.621949 0.858253 0.788621 0.026 Uiso 1 1 calc R . . . .
C6 C 0.58328(12) 0.77926(6) 0.67415(11) 0.0175(3) Uani 1 1 d . . . . .
C2 C 0.72501(13) 0.77355(7) 0.54085(12) 0.0208(3) Uani 1 1 d . . . . .
H2 H 0.752116 0.751848 0.478892 0.025 Uiso 1 1 calc R . . . .
C16 C 0.17611(13) 0.68318(6) 0.51147(12) 0.0196(3) Uani 1 1 d . . . . .
C15 C 0.29574(13) 0.66084(6) 0.60767(11) 0.0171(3) Uani 1 1 d . . . . .
C21 C 0.18142(13) 0.73991(7) 0.42855(12) 0.0216(3) Uani 1 1 d . . . . .
H21 H 0.278945 0.757191 0.458914 0.026 Uiso 1 1 calc R . . . .
C1 C 0.62245(12) 0.74745(6) 0.58280(11) 0.0169(3) Uani 1 1 d . . . . .
C9 C 0.74527(14) 0.62030(6) 0.73899(13) 0.0222(3) Uani 1 1 d . . . . .
H9 H 0.747032 0.659837 0.781851 0.027 Uiso 1 1 calc R . . . .
C7 C 0.46869(13) 0.74647(6) 0.70743(12) 0.0187(3) Uani 1 1 d . . . . .
H7A H 0.502667 0.732977 0.796565 0.022 Uiso 1 1 calc R . . . .
H7B H 0.388192 0.775870 0.693458 0.022 Uiso 1 1 calc R . . . .
C20 C 0.28685(14) 0.61111(6) 0.68870(12) 0.0213(3) Uani 1 1 d . . . . .
C11 C 0.83408(14) 0.51210(6) 0.73873(14) 0.0246(3) Uani 1 1 d . . . . .
C13 C 0.65594(14) 0.55468(6) 0.55536(13) 0.0219(3) Uani 1 1 d . . . . .
H13 H 0.595212 0.548889 0.471351 0.026 Uiso 1 1 calc R . . . .
C24 C 0.41367(14) 0.58937(6) 0.79796(12) 0.0230(3) Uani 1 1 d . . . . .
H24 H 0.492559 0.618967 0.801731 0.028 Uiso 1 1 calc R . . . .
C4 C 0.74880(14) 0.86296(7) 0.68255(13) 0.0243(3) Uani 1 1 d . . . . .
H4 H 0.792437 0.902530 0.716438 0.029 Uiso 1 1 calc R . . . .
C12 C 0.74501(14) 0.50484(6) 0.61538(14) 0.0257(3) Uani 1 1 d . . . . .
H12 H 0.745061 0.465653 0.571973 0.031 Uiso 1 1 calc R . . . .
C3 C 0.78697(14) 0.83161(7) 0.59073(13) 0.0239(3) Uani 1 1 d . . . . .
H3 H 0.855995 0.850055 0.561873 0.029 Uiso 1 1 calc R . . . .
C17 C 0.04910(14) 0.65253(8) 0.49458(13) 0.0264(3) Uani 1 1 d . . . . .
H17 H -0.032273 0.666375 0.428998 0.032 Uiso 1 1 calc R . . . .
C10 C 0.83310(14) 0.57056(7) 0.79896(13) 0.0251(3) Uani 1 1 d . . . . .
H10 H 0.893983 0.576378 0.882898 0.030 Uiso 1 1 calc R . . . .
C19 C 0.15707(16) 0.58226(7) 0.66840(13) 0.0295(3) Uani 1 1 d . . . . .
H19 H 0.149325 0.548290 0.721914 0.035 Uiso 1 1 calc R . . . .
C26 C 0.38846(18) 0.59487(8) 0.92312(13) 0.0360(4) Uani 1 1 d . . . . .
H26A H 0.361469 0.639186 0.934367 0.054 Uiso 1 1 calc GR . . . .
H26B H 0.474268 0.583642 0.991768 0.054 Uiso 1 1 calc GR . . . .
H26C H 0.313485 0.565304 0.923493 0.054 Uiso 1 1 calc GR . . . .
C22 C 0.14759(16) 0.71939(8) 0.29200(13) 0.0305(3) Uani 1 1 d . . . . .
H22A H 0.212150 0.685253 0.287138 0.046 Uiso 1 1 calc GR . . . .
H22B H 0.157421 0.756494 0.242084 0.046 Uiso 1 1 calc GR . . . .
H22C H 0.051476 0.703232 0.259103 0.046 Uiso 1 1 calc GR . . . .
C23 C 0.08384(18) 0.79419(8) 0.43759(16) 0.0382(4) Uani 1 1 d . . . . .
H23A H -0.012914 0.778764 0.406864 0.057 Uiso 1 1 calc GR . . . .
H23B H 0.093509 0.830790 0.386429 0.057 Uiso 1 1 calc GR . . . .
H23C H 0.108321 0.807837 0.525261 0.057 Uiso 1 1 calc GR . . . .
C25 C 0.45876(17) 0.52118(7) 0.77888(14) 0.0312(3) Uani 1 1 d . . . . .
H25A H 0.382488 0.491038 0.772470 0.047 Uiso 1 1 calc GR . . . .
H25B H 0.541200 0.509159 0.850356 0.047 Uiso 1 1 calc GR . . . .
H25C H 0.481579 0.519520 0.701543 0.047 Uiso 1 1 calc GR . . . .
C18 C 0.03946(15) 0.60231(8) 0.57160(14) 0.0327(4) Uani 1 1 d . . . . .
H18 H -0.047717 0.581623 0.558101 0.039 Uiso 1 1 calc R . . . .
C14 C 0.92897(17) 0.45809(7) 0.80643(17) 0.0370(4) Uani 1 1 d . . . . .
H14A H 0.885045 0.434353 0.857990 0.056 Uiso 1 1 calc GR . . . .
H14B H 1.018267 0.476021 0.860353 0.056 Uiso 1 1 calc GR . . . .
H14C H 0.945293 0.428779 0.744958 0.056 Uiso 1 1 calc GR . . . .


_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 N1 1.7058(11) . ?
P1 C8 1.8433(13) . ?
P1 C1 1.8263(13) . ?
N1 C15 1.4335(16) . ?
N1 C7 1.4608(16) . ?
C8 C9 1.3963(18) . ?
C8 C13 1.3920(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3907(18) . ?
C5 C4 1.390(2) . ?
C6 C1 1.3945(18) . ?
C6 C7 1.5043(17) . ?
C2 H2 0.9500 . ?
C2 C1 1.3946(18) . ?
C2 C3 1.3875(19) . ?
C16 C15 1.4084(18) . ?
C16 C21 1.5180(18) . ?
C16 C17 1.3940(19) . ?
C15 C20 1.4038(18) . ?
C21 H21 1.0000 . ?
C21 C22 1.5266(19) . ?
C21 C23 1.527(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.3830(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C20 C24 1.5220(18) . ?
C20 C19 1.3962(19) . ?
C11 C12 1.392(2) . ?
C11 C10 1.393(2) . ?
C11 C14 1.5076(19) . ?
C13 H13 0.9500 . ?
C13 C12 1.391(2) . ?
C24 H24 1.0000 . ?
C24 C26 1.528(2) . ?
C24 C25 1.525(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.389(2) . ?
C12 H12 0.9500 . ?
C3 H3 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.383(2) . ?
C10 H10 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.384(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C18 H18 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
N1 P1 C8 105.85(5) . . ?
N1 P1 C1 89.35(5) . . ?
C1 P1 C8 100.44(5) . . ?
C15 N1 P1 122.16(8) . . ?
C15 N1 C7 118.37(10) . . ?
C7 N1 P1 118.10(8) . . ?
C9 C8 P1 124.49(10) . . ?
C13 C8 P1 117.26(10) . . ?
C13 C8 C9 118.15(12) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.18(13) . . ?
C5 C6 C1 120.29(12) . . ?
C5 C6 C7 125.30(12) . . ?
C1 C6 C7 114.40(11) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C3 C2 C1 119.17(12) . . ?
C15 C16 C21 122.05(11) . . ?
C17 C16 C15 118.29(12) . . ?
C17 C16 C21 119.65(12) . . ?
C16 C15 N1 119.50(11) . . ?
C20 C15 N1 119.36(11) . . ?
C20 C15 C16 121.13(12) . . ?
C16 C21 H21 107.7 . . ?
C16 C21 C22 111.56(11) . . ?
C16 C21 C23 111.68(11) . . ?
C22 C21 H21 107.7 . . ?
C22 C21 C23 110.19(12) . . ?
C23 C21 H21 107.7 . . ?
C6 C1 P1 111.97(9) . . ?
C6 C1 C2 120.31(12) . . ?
C2 C1 P1 127.71(10) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.53(12) . . ?
C10 C9 H9 119.7 . . ?
N1 C7 C6 105.89(10) . . ?
N1 C7 H7A 110.6 . . ?
N1 C7 H7B 110.6 . . ?
C6 C7 H7A 110.6 . . ?
C6 C7 H7B 110.6 . . ?
H7A C7 H7B 108.7 . . ?
C15 C20 C24 121.62(12) . . ?
C19 C20 C15 118.32(12) . . ?
C19 C20 C24 120.04(12) . . ?
C12 C11 C10 118.38(12) . . ?
C12 C11 C14 121.11(13) . . ?
C10 C11 C14 120.50(13) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.29(12) . . ?
C12 C13 H13 119.4 . . ?
C20 C24 H24 107.4 . . ?
C20 C24 C26 111.66(12) . . ?
C20 C24 C25 111.87(12) . . ?
C26 C24 H24 107.4 . . ?
C25 C24 H24 107.4 . . ?
C25 C24 C26 110.74(12) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.56(12) . . ?
C3 C4 H4 119.7 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.31(12) . . ?
C13 C12 H12 119.8 . . ?
C2 C3 C4 120.48(12) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.18(13) . . ?
C18 C17 H17 119.4 . . ?
C9 C10 C11 121.31(13) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C20 C19 H19 119.4 . . ?
C18 C19 C20 121.13(13) . . ?
C18 C19 H19 119.4 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C17 C18 C19 119.89(13) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_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_cain79_0m_a_sq
_audit_block_doi                 10.5517/ccdc.csd.cc250xy2
_database_code_depnum_ccdc_archive 'CCDC 1996894'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0DT01367F 2020
loop_
_audit_author_name
_audit_author_address
'Arnold L. Rheingold'
;University of California, San Diego
United States of America
;
_audit_update_record             
;
2020-12-19 deposited with the CCDC.	2021-01-05 downloaded from the CCDC.
;
_audit_creation_date             2019-04-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H28 N P'
_chemical_formula_sum            'C27 H28 N P'
_chemical_formula_weight         397.47
_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'
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                   8.4342(5)
_cell_length_b                   10.7526(6)
_cell_length_c                   14.1948(8)
_cell_angle_alpha                97.641(2)
_cell_angle_beta                 103.063(2)
_cell_angle_gamma                90.538(2)
_cell_volume                     1241.83(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3654
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.615
_cell_measurement_theta_min      2.254
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.777
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_av_unetI/netI     0.0975
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15194
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_min         1.487
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4282
_reflns_number_total             6203
_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       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         6203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      0.986
_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)+(0.0735P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1567
_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 Ternary CH refined with riding coordinates:
 C22(H22), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C19(H19), C20(H20), C18(H18), C11(H11), C13(H13), C12(H12), C3(H3),
 C5(H5), C4(H4), C1(H1), C2(H2)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C26(H26A,H26B,
 H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.69084(6) 0.50467(4) 0.79083(3) 0.01827(14) Uani 1 1 d . . . . .
N1 N 0.85250(17) 0.47374(13) 0.73981(10) 0.0172(3) Uani 1 1 d . . . . .
C16 C 1.0174(2) 0.50042(16) 0.79445(12) 0.0166(4) Uani 1 1 d . . . . .
C17 C 1.1005(2) 0.61096(16) 0.78668(13) 0.0186(4) Uani 1 1 d . . . . .
C14 C 0.6388(2) 0.39668(16) 0.60517(13) 0.0188(4) Uani 1 1 d . . . . .
C9 C 0.5540(2) 0.43093(15) 0.67757(13) 0.0182(4) Uani 1 1 d . . . . .
C21 C 1.0930(2) 0.41475(17) 0.85639(13) 0.0206(4) Uani 1 1 d . . . . .
C10 C 0.3872(2) 0.40766(16) 0.65975(14) 0.0216(4) Uani 1 1 d . . . . .
H10 H 0.3300 0.4306 0.7095 0.026 Uiso 1 1 calc R . . . .
C22 C 1.0244(2) 0.70440(16) 0.72036(13) 0.0207(4) Uani 1 1 d . . . . .
H22 H 0.9072 0.6780 0.6934 0.025 Uiso 1 1 calc R . . . .
C7 C 0.6274(2) 0.77833(18) 0.79531(15) 0.0246(4) Uani 1 1 d . . . . .
C6 C 0.6040(2) 0.91118(18) 0.81025(16) 0.0284(5) Uani 1 1 d . . . . .
C25 C 1.0070(2) 0.29560(17) 0.86771(14) 0.0258(4) Uani 1 1 d . . . . .
H25 H 0.8971 0.2875 0.8219 0.031 Uiso 1 1 calc R . . . .
C19 C 1.3355(2) 0.5523(2) 0.90219(15) 0.0295(5) Uani 1 1 d . . . . .
H19 H 1.4442 0.5699 0.9390 0.035 Uiso 1 1 calc R . . . .
C20 C 1.2511(2) 0.44333(19) 0.90955(14) 0.0279(5) Uani 1 1 d . . . . .
H20 H 1.3032 0.3873 0.9521 0.033 Uiso 1 1 calc R . . . .
C18 C 1.2601(2) 0.63468(18) 0.84086(14) 0.0235(4) Uani 1 1 d . . . . .
H18 H 1.3180 0.7087 0.8356 0.028 Uiso 1 1 calc R . . . .
C8 C 0.6479(2) 0.66645(17) 0.78283(14) 0.0220(4) Uani 1 1 d . . . . .
C15 C 0.8193(2) 0.42903(17) 0.63522(13) 0.0220(4) Uani 1 1 d . . . . .
H15A H 0.8824 0.3541 0.6221 0.026 Uiso 1 1 calc R . . . .
H15B H 0.8483 0.4953 0.5991 0.026 Uiso 1 1 calc R . . . .
C11 C 0.3054(2) 0.35035(17) 0.56826(15) 0.0256(4) Uani 1 1 d . . . . .
H11 H 0.1910 0.3340 0.5551 0.031 Uiso 1 1 calc R . . . .
C13 C 0.5551(2) 0.33920(17) 0.51316(14) 0.0247(4) Uani 1 1 d . . . . .
H13 H 0.6118 0.3159 0.4632 0.030 Uiso 1 1 calc R . . . .
C12 C 0.3892(2) 0.31661(17) 0.49564(15) 0.0270(4) Uani 1 1 d . . . . .
H12 H 0.3314 0.2775 0.4332 0.032 Uiso 1 1 calc R . . . .
C24 C 1.0320(3) 0.83777(17) 0.77642(15) 0.0295(5) Uani 1 1 d . . . . .
H24A H 0.9840 0.8361 0.8330 0.044 Uiso 1 1 calc GR . . . .
H24B H 0.9711 0.8936 0.7333 0.044 Uiso 1 1 calc GR . . . .
H24C H 1.1459 0.8686 0.7986 0.044 Uiso 1 1 calc GR . . . .
C23 C 1.1062(3) 0.70414(19) 0.63465(14) 0.0294(5) Uani 1 1 d . . . . .
H23A H 1.2208 0.7321 0.6592 0.044 Uiso 1 1 calc GR . . . .
H23B H 1.0508 0.7612 0.5907 0.044 Uiso 1 1 calc GR . . . .
H23C H 1.0995 0.6190 0.5990 0.044 Uiso 1 1 calc GR . . . .
C3 C 0.5616(3) 1.1685(2) 0.8373(2) 0.0480(7) Uani 1 1 d . . . . .
H3 H 0.5432 1.2559 0.8468 0.058 Uiso 1 1 calc R . . . .
C5 C 0.6242(3) 0.9766(2) 0.90136(19) 0.0485(7) Uani 1 1 d . . . . .
H5 H 0.6541 0.9337 0.9567 0.058 Uiso 1 1 calc R . . . .
C4 C 0.6019(4) 1.1047(2) 0.9150(2) 0.0547(7) Uani 1 1 d . . . . .
H4 H 0.6150 1.1481 0.9793 0.066 Uiso 1 1 calc R . . . .
C27 C 0.9855(3) 0.2975(2) 0.97055(17) 0.0508(7) Uani 1 1 d . . . . .
H27A H 1.0920 0.3112 1.0165 0.076 Uiso 1 1 calc GR . . . .
H27B H 0.9360 0.2170 0.9767 0.076 Uiso 1 1 calc GR . . . .
H27C H 0.9146 0.3655 0.9853 0.076 Uiso 1 1 calc GR . . . .
C1 C 0.5662(4) 0.9771(2) 0.7309(2) 0.0649(9) Uani 1 1 d . . . . .
H1 H 0.5529 0.9342 0.6664 0.078 Uiso 1 1 calc R . . . .
C26 C 1.1042(4) 0.1799(2) 0.8426(2) 0.0697(9) Uani 1 1 d . . . . .
H26A H 1.1204 0.1780 0.7762 0.105 Uiso 1 1 calc GR . . . .
H26B H 1.0436 0.1033 0.8467 0.105 Uiso 1 1 calc GR . . . .
H26C H 1.2103 0.1849 0.8890 0.105 Uiso 1 1 calc GR . . . .
C2 C 0.5476(4) 1.1065(3) 0.7459(2) 0.0738(10) Uani 1 1 d . . . . .
H2 H 0.5250 1.1517 0.6915 0.089 Uiso 1 1 calc R . . . .


_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 N1 1.6986(15) . ?
P1 C9 1.8305(18) . ?
P1 C8 1.7932(19) . ?
N1 C16 1.437(2) . ?
N1 C15 1.461(2) . ?
C16 C17 1.404(2) . ?
C16 C21 1.414(2) . ?
C17 C22 1.516(2) . ?
C17 C18 1.393(3) . ?
C14 C9 1.393(3) . ?
C14 C15 1.509(3) . ?
C14 C13 1.395(3) . ?
C9 C10 1.386(3) . ?
C21 C25 1.511(3) . ?
C21 C20 1.385(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(3) . ?
C22 H22 1.0000 . ?
C22 C24 1.538(3) . ?
C22 C23 1.528(3) . ?
C7 C6 1.438(3) . ?
C7 C8 1.212(3) . ?
C6 C5 1.361(3) . ?
C6 C1 1.389(3) . ?
C25 H25 1.0000 . ?
C25 C27 1.509(3) . ?
C25 C26 1.543(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.394(3) . ?
C19 C18 1.383(3) . ?
C20 H20 0.9500 . ?
C18 H18 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.378(3) . ?
C12 H12 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.356(4) . ?
C3 C2 1.357(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C1 H1 0.9500 . ?
C1 C2 1.395(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C2 H2 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
N1 P1 C9 89.64(8) . . ?
N1 P1 C8 106.70(8) . . ?
C8 P1 C9 99.89(8) . . ?
C16 N1 P1 121.93(11) . . ?
C16 N1 C15 120.02(14) . . ?
C15 N1 P1 117.82(12) . . ?
C17 C16 N1 119.93(15) . . ?
C17 C16 C21 120.99(16) . . ?
C21 C16 N1 119.08(16) . . ?
C16 C17 C22 122.57(16) . . ?
C18 C17 C16 118.68(16) . . ?
C18 C17 C22 118.74(17) . . ?
C9 C14 C15 114.70(16) . . ?
C9 C14 C13 119.80(17) . . ?
C13 C14 C15 125.48(17) . . ?
C14 C9 P1 111.26(14) . . ?
C10 C9 P1 127.91(15) . . ?
C10 C9 C14 120.84(17) . . ?
C16 C21 C25 122.58(16) . . ?
C20 C21 C16 118.10(17) . . ?
C20 C21 C25 119.31(16) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 118.92(18) . . ?
C11 C10 H10 120.5 . . ?
C17 C22 H22 108.0 . . ?
C17 C22 C24 111.66(15) . . ?
C17 C22 C23 110.89(15) . . ?
C24 C22 H22 108.0 . . ?
C23 C22 H22 108.0 . . ?
C23 C22 C24 110.20(15) . . ?
C8 C7 C6 179.7(2) . . ?
C5 C6 C7 121.7(2) . . ?
C5 C6 C1 118.1(2) . . ?
C1 C6 C7 120.1(2) . . ?
C21 C25 H25 108.8 . . ?
C21 C25 C26 110.62(19) . . ?
C27 C25 C21 111.40(16) . . ?
C27 C25 H25 108.8 . . ?
C27 C25 C26 108.5(2) . . ?
C26 C25 H25 108.8 . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.52(18) . . ?
C21 C20 C19 121.60(18) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.11(18) . . ?
C19 C18 H18 119.4 . . ?
C7 C8 P1 168.38(18) . . ?
N1 C15 C14 105.40(15) . . ?
N1 C15 H15A 110.7 . . ?
N1 C15 H15B 110.7 . . ?
C14 C15 H15A 110.7 . . ?
C14 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.49(18) . . ?
C12 C11 H11 119.8 . . ?
C14 C13 H13 120.4 . . ?
C12 C13 C14 119.17(18) . . ?
C12 C13 H13 120.4 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.78(18) . . ?
C13 C12 H12 119.6 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C6 C5 H5 119.4 . . ?
C6 C5 C4 121.3(2) . . ?
C4 C5 H5 119.4 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C2 119.9(3) . . ?
C2 C1 H1 120.1 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 13 0 ' '
2 0.002 0.000 0.500 165 49 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
