# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_BSYU001
_database_code_depnum_ccdc_archive 'CCDC 1898220'
loop_
_audit_author_name
_audit_author_address
'Chau Ming So'
;The Hong Kong Polytechnic University
Hong Kong
;
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2020-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H39 N2 P'
_chemical_formula_weight         446.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   15.0158(12)
_cell_length_b                   15.6985(10)
_cell_length_c                   21.9190(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5166.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    585
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6423
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            93019
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.094
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4669
_reflns_number_gt                3583
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0628P)²+1.9578P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0065(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4669
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.89431(3) 0.15221(3) 0.31614(2) 0.04215(17) Uani 1 1 d . . . . .
N1 N 0.83609(11) -0.00558(9) 0.21324(6) 0.0466(4) Uani 1 1 d . . . . .
N2 N 1.07309(12) -0.17907(10) 0.38246(7) 0.0513(4) Uani 1 1 d . . . . .
C1 C 0.83065(14) 0.01082(11) 0.15156(8) 0.0483(5) Uani 1 1 d . . . . .
C2 C 0.75605(17) 0.01329(13) 0.11372(10) 0.0634(6) Uani 1 1 d . . . . .
H2A H 0.6991 0.0036 0.1288 0.076 Uiso 1 1 calc R U . . .
C3 C 0.7707(2) 0.03070(15) 0.05290(11) 0.0758(7) Uani 1 1 d . . . . .
H3A H 0.7224 0.0331 0.0264 0.091 Uiso 1 1 calc R U . . .
C4 C 0.8547(2) 0.04452(16) 0.03060(10) 0.0756(7) Uani 1 1 d . . . . .
H4A H 0.8620 0.0560 -0.0107 0.091 Uiso 1 1 calc R U . . .
C5 C 0.92821(18) 0.04192(14) 0.06743(9) 0.0650(6) Uani 1 1 d . . . . .
H5A H 0.9847 0.0514 0.0514 0.078 Uiso 1 1 calc R U . . .
C6 C 0.91684(15) 0.02473(12) 0.12985(8) 0.0501(5) Uani 1 1 d . . . . .
C7 C 0.97481(15) 0.01575(12) 0.18076(8) 0.0505(5) Uani 1 1 d . . . . .
H7A H 1.0365 0.0208 0.1800 0.061 Uiso 1 1 calc R U . . .
C8 C 0.92447(13) -0.00141(11) 0.23061(8) 0.0431(4) Uani 1 1 d . . . . .
C9 C 0.76142(15) -0.02626(15) 0.25090(10) 0.0655(6) Uani 1 1 d . . . . .
H9A H 0.7812 -0.0350 0.2921 0.098 Uiso 1 1 calc R U . . .
H9B H 0.7192 0.0197 0.2499 0.098 Uiso 1 1 calc R U . . .
H9C H 0.7337 -0.0773 0.2360 0.098 Uiso 1 1 calc R U . . .
C10 C 0.95190(12) -0.01467(11) 0.29511(7) 0.0402(4) Uani 1 1 d . . . . .
C11 C 0.99650(12) -0.08909(11) 0.30963(8) 0.0425(4) Uani 1 1 d . . . . .
H11A H 1.0077 -0.1285 0.2789 0.051 Uiso 1 1 calc R U . . .
C12 C 1.02549(12) -0.10713(11) 0.36931(8) 0.0412(4) Uani 1 1 d . . . . .
C13 C 1.00254(13) -0.04747(11) 0.41436(8) 0.0464(5) Uani 1 1 d . . . . .
H13A H 1.0174 -0.0581 0.4548 0.056 Uiso 1 1 calc R U . . .
C14 C 0.95860(13) 0.02624(11) 0.39954(8) 0.0457(5) Uani 1 1 d . . . . .
H14A H 0.9446 0.0642 0.4307 0.055 Uiso 1 1 calc R U . . .
C15 C 0.93388(12) 0.04697(11) 0.34008(7) 0.0400(4) Uani 1 1 d . . . . .
C16 C 1.08550(15) -0.24437(13) 0.33684(10) 0.0620(6) Uani 1 1 d . . . . .
H16A H 1.1202 -0.2900 0.3537 0.093 Uiso 1 1 calc R U . . .
H16B H 1.0285 -0.2658 0.3242 0.093 Uiso 1 1 calc R U . . .
H16C H 1.1160 -0.2207 0.3023 0.093 Uiso 1 1 calc R U . . .
C17 C 1.10223(15) -0.19639(15) 0.44391(9) 0.0624(6) Uani 1 1 d . . . . .
H17A H 1.1345 -0.2492 0.4447 0.094 Uiso 1 1 calc R U . . .
H17B H 1.1403 -0.1511 0.4576 0.094 Uiso 1 1 calc R U . . .
H17C H 1.0514 -0.2004 0.4703 0.094 Uiso 1 1 calc R U . . .
C18 C 0.99623(13) 0.21802(11) 0.32995(8) 0.0451(4) Uani 1 1 d . . . . .
H18A H 0.9836 0.2737 0.3118 0.054 Uiso 1 1 calc R U . . .
C19 C 1.07532(14) 0.18245(13) 0.29431(10) 0.0567(5) Uani 1 1 d . . . . .
H19A H 1.0924 0.1279 0.3115 0.068 Uiso 1 1 calc R U . . .
H19B H 1.0578 0.1732 0.2522 0.068 Uiso 1 1 calc R U . . .
C20 C 1.15488(15) 0.24260(16) 0.29614(11) 0.0701(6) Uani 1 1 d . . . . .
H20A H 1.2050 0.2160 0.2758 0.084 Uiso 1 1 calc R U . . .
H20B H 1.1403 0.2944 0.2742 0.084 Uiso 1 1 calc R U . . .
C21 C 1.18085(16) 0.26474(15) 0.36064(12) 0.0736(7) Uani 1 1 d . . . . .
H21A H 1.2277 0.3073 0.3599 0.088 Uiso 1 1 calc R U . . .
H21B H 1.2041 0.2144 0.3807 0.088 Uiso 1 1 calc R U . . .
C22 C 1.10253(16) 0.29855(15) 0.39646(11) 0.0709(7) Uani 1 1 d . . . . .
H22A H 1.0838 0.3526 0.3793 0.085 Uiso 1 1 calc R U . . .
H22B H 1.1206 0.3085 0.4384 0.085 Uiso 1 1 calc R U . . .
C23 C 1.02445(15) 0.23632(13) 0.39544(9) 0.0588(5) Uani 1 1 d . . . . .
H23A H 1.0417 0.1836 0.4153 0.071 Uiso 1 1 calc R U . . .
H23B H 0.9747 0.2604 0.4178 0.071 Uiso 1 1 calc R U . . .
C24 C 0.82006(13) 0.18594(11) 0.37903(8) 0.0461(4) Uani 1 1 d . . . . .
H24A H 0.8527 0.1815 0.4176 0.055 Uiso 1 1 calc R U . . .
C25 C 0.73805(15) 0.12944(14) 0.38247(11) 0.0652(6) Uani 1 1 d . . . . .
H25A H 0.7561 0.0714 0.3913 0.078 Uiso 1 1 calc R U . . .
H25B H 0.7080 0.1296 0.3433 0.078 Uiso 1 1 calc R U . . .
C26 C 0.67415(17) 0.16007(18) 0.43155(14) 0.0851(8) Uani 1 1 d . . . . .
H26A H 0.6212 0.1247 0.4312 0.102 Uiso 1 1 calc R U . . .
H26B H 0.7021 0.1543 0.4712 0.102 Uiso 1 1 calc R U . . .
C27 C 0.64792(19) 0.2522(2) 0.42149(14) 0.0918(9) Uani 1 1 d . . . . .
H27A H 0.6139 0.2566 0.3840 0.110 Uiso 1 1 calc R U . . .
H27B H 0.6101 0.2707 0.4548 0.110 Uiso 1 1 calc R U . . .
C28 C 0.72791(18) 0.30947(16) 0.41764(12) 0.0766(7) Uani 1 1 d . . . . .
H28A H 0.7577 0.3108 0.4569 0.092 Uiso 1 1 calc R U . . .
H28B H 0.7087 0.3669 0.4080 0.092 Uiso 1 1 calc R U . . .
C29 C 0.79274(16) 0.27908(13) 0.36927(10) 0.0611(6) Uani 1 1 d . . . . .
H29A H 0.8455 0.3147 0.3701 0.073 Uiso 1 1 calc R U . . .
H29B H 0.7654 0.2849 0.3294 0.073 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C15 1.8325(17) . ?
P1 C24 1.8504(19) . ?
P1 C18 1.8711(19) . ?
N1 C1 1.379(2) . ?
N1 C8 1.382(2) . ?
N1 C9 1.430(3) . ?
N2 C12 1.367(2) . ?
N2 C17 1.442(2) . ?
N2 C16 1.444(2) . ?
C1 C2 1.394(3) . ?
C1 C6 1.396(3) . ?
C2 C3 1.378(3) . ?
C3 C4 1.371(4) . ?
C4 C5 1.368(3) . ?
C5 C6 1.405(3) . ?
C6 C7 1.422(3) . ?
C7 C8 1.356(3) . ?
C8 C10 1.487(2) . ?
C10 C11 1.384(2) . ?
C10 C15 1.408(2) . ?
C11 C12 1.407(2) . ?
C12 C13 1.404(2) . ?
C13 C14 1.371(3) . ?
C14 C15 1.394(2) . ?
C18 C23 1.524(3) . ?
C18 C19 1.527(3) . ?
C19 C20 1.523(3) . ?
C20 C21 1.507(3) . ?
C21 C22 1.510(3) . ?
C22 C23 1.526(3) . ?
C24 C25 1.520(3) . ?
C24 C29 1.534(3) . ?
C25 C26 1.520(3) . ?
C26 C27 1.514(4) . ?
C27 C28 1.503(4) . ?
C28 C29 1.516(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 P1 C24 103.89(8) . . ?
C15 P1 C18 100.73(8) . . ?
C24 P1 C18 102.37(8) . . ?
C1 N1 C8 108.55(16) . . ?
C1 N1 C9 124.21(16) . . ?
C8 N1 C9 127.20(16) . . ?
C12 N2 C17 120.75(16) . . ?
C12 N2 C16 120.52(15) . . ?
C17 N2 C16 118.28(16) . . ?
N1 C1 C2 129.5(2) . . ?
N1 C1 C6 107.98(16) . . ?
C2 C1 C6 122.52(18) . . ?
C3 C2 C1 116.9(2) . . ?
C4 C3 C2 121.5(2) . . ?
C5 C4 C3 121.8(2) . . ?
C4 C5 C6 118.9(2) . . ?
C1 C6 C5 118.34(19) . . ?
C1 C6 C7 106.52(17) . . ?
C5 C6 C7 135.1(2) . . ?
C8 C7 C6 108.11(19) . . ?
C7 C8 N1 108.82(16) . . ?
C7 C8 C10 129.76(18) . . ?
N1 C8 C10 121.41(16) . . ?
C11 C10 C15 120.82(15) . . ?
C11 C10 C8 118.09(15) . . ?
C15 C10 C8 121.09(15) . . ?
C10 C11 C12 122.23(15) . . ?
N2 C12 C13 122.08(16) . . ?
N2 C12 C11 121.59(15) . . ?
C13 C12 C11 116.33(16) . . ?
C14 C13 C12 120.97(16) . . ?
C13 C14 C15 123.14(16) . . ?
C14 C15 C10 116.31(16) . . ?
C14 C15 P1 124.38(13) . . ?
C10 C15 P1 118.79(12) . . ?
C23 C18 C19 109.54(17) . . ?
C23 C18 P1 118.94(13) . . ?
C19 C18 P1 110.57(13) . . ?
C20 C19 C18 111.70(17) . . ?
C21 C20 C19 111.75(19) . . ?
C20 C21 C22 111.54(19) . . ?
C21 C22 C23 111.45(19) . . ?
C18 C23 C22 110.36(17) . . ?
C25 C24 C29 110.28(17) . . ?
C25 C24 P1 110.99(13) . . ?
C29 C24 P1 109.28(13) . . ?
C24 C25 C26 111.23(18) . . ?
C27 C26 C25 111.3(2) . . ?
C28 C27 C26 111.8(2) . . ?
C27 C28 C29 111.3(2) . . ?
C28 C29 C24 111.98(18) . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.035

_shelxl_version_number           2014/6



