# 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_180119b
_database_code_depnum_ccdc_archive 'CCDC 1828876'
loop_
_audit_author_name
_audit_author_address
'Ye Jingjing'
;Liaocheng University
China
;
_audit_update_record             
;
2018-03-12 deposited with the CCDC.	2020-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H27 N0 O P'
_chemical_formula_weight         314.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   5.6725(4)
_cell_length_b                   16.4065(13)
_cell_length_c                   39.935(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3716.6(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2787
_cell_measurement_theta_min      2.481
_cell_measurement_theta_max      19.3875

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9389
_exptl_absorpt_correction_T_max  0.9499
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;
_chemical_absolute_configuration S
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18751
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_sigmaI/netI    0.1161
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         25.02
_reflns_number_total             6557
_reflns_number_gt                3903
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+1.4540P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.14(15)
_refine_ls_number_reflns         6557
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1685
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.3313(2) 0.53082(9) 0.89890(3) 0.0579(4) Uani 1 1 d . . .
P2 P 0.1217(2) 0.26875(8) 0.85437(3) 0.0556(4) Uani 1 1 d . . .
O1 O 0.5817(5) 0.5521(3) 0.90330(8) 0.0950(14) Uani 1 1 d . . .
O2 O -0.1332(6) 0.2607(3) 0.85845(8) 0.0888(12) Uani 1 1 d . . .
C1 C 0.2415(7) 0.5288(3) 0.85593(11) 0.0468(11) Uani 1 1 d . . .
C2 C 0.0268(8) 0.4924(3) 0.84635(11) 0.0493(11) Uani 1 1 d . . .
H2 H -0.0771 0.4742 0.8627 0.059 Uiso 1 1 calc R . .
C3 C -0.0303(8) 0.4838(3) 0.81345(11) 0.0553(12) Uani 1 1 d . . .
H3 H -0.1717 0.4587 0.8078 0.066 Uiso 1 1 calc R . .
C4 C 0.1196(8) 0.5121(3) 0.78779(10) 0.0486(11) Uani 1 1 d . . .
C5 C 0.0668(10) 0.5053(3) 0.75356(12) 0.0683(15) Uani 1 1 d . . .
H5 H -0.0734 0.4805 0.7471 0.082 Uiso 1 1 calc R . .
C6 C 0.2142(12) 0.5338(4) 0.72974(14) 0.0854(18) Uani 1 1 d . . .
H6 H 0.1768 0.5277 0.7072 0.103 Uiso 1 1 calc R . .
C7 C 0.4238(11) 0.5727(4) 0.73919(14) 0.0825(18) Uani 1 1 d . . .
H7 H 0.5234 0.5930 0.7227 0.099 Uiso 1 1 calc R . .
C8 C 0.4852(10) 0.5813(3) 0.77217(12) 0.0658(14) Uani 1 1 d . . .
H8 H 0.6252 0.6071 0.7780 0.079 Uiso 1 1 calc R . .
C9 C 0.3332(8) 0.5504(3) 0.79732(10) 0.0495(11) Uani 1 1 d . . .
C10 C 0.3910(8) 0.5564(3) 0.83176(10) 0.0495(11) Uani 1 1 d . . .
H10 H 0.5339 0.5797 0.8380 0.059 Uiso 1 1 calc R . .
C11 C 0.1271(8) 0.5944(2) 0.92145(9) 0.0445(10) Uani 1 1 d . . .
H11 H -0.0311 0.5719 0.9181 0.053 Uiso 1 1 calc R . .
C12 C 0.1282(11) 0.6808(3) 0.90694(11) 0.0664(14) Uani 1 1 d . . .
H12A H 0.2852 0.7036 0.9091 0.080 Uiso 1 1 calc R . .
H12B H 0.0910 0.6781 0.8833 0.080 Uiso 1 1 calc R . .
C13 C -0.0442(12) 0.7362(3) 0.92386(13) 0.0879(19) Uani 1 1 d . . .
H13 H -0.2019 0.7136 0.9201 0.106 Uiso 1 1 calc R . .
C14 C -0.0034(14) 0.7373(3) 0.96137(13) 0.097(2) Uani 1 1 d . . .
H14A H -0.1244 0.7701 0.9720 0.117 Uiso 1 1 calc R . .
H14B H 0.1481 0.7623 0.9660 0.117 Uiso 1 1 calc R . .
C15 C -0.0080(11) 0.6520(3) 0.97596(12) 0.0799(17) Uani 1 1 d . . .
H15A H -0.1641 0.6289 0.9729 0.096 Uiso 1 1 calc R . .
H15B H 0.0229 0.6549 0.9998 0.096 Uiso 1 1 calc R . .
C16 C 0.1746(9) 0.5956(3) 0.95953(10) 0.0538(12) Uani 1 1 d . . .
H16 H 0.3292 0.6211 0.9628 0.065 Uiso 1 1 calc R . .
C17 C -0.0413(18) 0.8222(3) 0.90890(17) 0.149(4) Uani 1 1 d . . .
H17A H -0.0498 0.8187 0.8849 0.224 Uiso 1 1 calc R . .
H17B H 0.1019 0.8493 0.9152 0.224 Uiso 1 1 calc R . .
H17C H -0.1740 0.8524 0.9172 0.224 Uiso 1 1 calc R . .
C18 C 0.1856(10) 0.5115(3) 0.97599(12) 0.0677(14) Uani 1 1 d . . .
H18 H 0.3026 0.4799 0.9634 0.081 Uiso 1 1 calc R . .
C19 C -0.0450(12) 0.4645(4) 0.97378(16) 0.104(2) Uani 1 1 d . . .
H19A H -0.0925 0.4602 0.9508 0.157 Uiso 1 1 calc R . .
H19B H -0.1646 0.4926 0.9863 0.157 Uiso 1 1 calc R . .
H19C H -0.0235 0.4109 0.9829 0.157 Uiso 1 1 calc R . .
C20 C 0.2745(12) 0.5161(4) 1.01194(13) 0.109(2) Uani 1 1 d . . .
H20A H 0.2934 0.4619 1.0207 0.164 Uiso 1 1 calc R . .
H20B H 0.1626 0.5453 1.0254 0.164 Uiso 1 1 calc R . .
H20C H 0.4234 0.5438 1.0124 0.164 Uiso 1 1 calc R . .
C21 C 0.2127(7) 0.2793(3) 0.81157(10) 0.0463(11) Uani 1 1 d . . .
C22 C 0.4303(8) 0.3160(3) 0.80412(11) 0.0547(12) Uani 1 1 d . . .
H22 H 0.5289 0.3334 0.8213 0.066 Uiso 1 1 calc R . .
C23 C 0.4960(9) 0.3259(3) 0.77137(12) 0.0616(13) Uani 1 1 d . . .
H23 H 0.6380 0.3517 0.7666 0.074 Uiso 1 1 calc R . .
C24 C 0.3551(9) 0.2981(3) 0.74497(11) 0.0528(12) Uani 1 1 d . . .
C25 C 0.4198(10) 0.3062(3) 0.71112(12) 0.0712(15) Uani 1 1 d . . .
H25 H 0.5605 0.3322 0.7057 0.085 Uiso 1 1 calc R . .
C26 C 0.2817(11) 0.2769(4) 0.68623(13) 0.0860(18) Uani 1 1 d . . .
H26 H 0.3294 0.2819 0.6640 0.103 Uiso 1 1 calc R . .
C27 C 0.0694(10) 0.2394(4) 0.69380(12) 0.0815(17) Uani 1 1 d . . .
H27 H -0.0265 0.2203 0.6766 0.098 Uiso 1 1 calc R . .
C28 C 0.0005(10) 0.2303(3) 0.72621(11) 0.0690(14) Uani 1 1 d . . .
H28 H -0.1404 0.2038 0.7310 0.083 Uiso 1 1 calc R . .
C29 C 0.1396(8) 0.2606(3) 0.75232(10) 0.0470(10) Uani 1 1 d . . .
C30 C 0.0730(8) 0.2521(3) 0.78661(10) 0.0503(11) Uani 1 1 d . . .
H30 H -0.0698 0.2274 0.7919 0.060 Uiso 1 1 calc R . .
C31 C 0.2917(8) 0.1878(3) 0.87178(10) 0.0505(12) Uani 1 1 d . . .
H31 H 0.4584 0.2015 0.8687 0.061 Uiso 1 1 calc R . .
C32 C 0.2459(11) 0.1093(3) 0.85321(12) 0.0749(17) Uani 1 1 d . . .
H32A H 0.0802 0.0957 0.8554 0.090 Uiso 1 1 calc R . .
H32B H 0.2780 0.1180 0.8296 0.090 Uiso 1 1 calc R . .
C33 C 0.3894(16) 0.0385(3) 0.86508(14) 0.111(3) Uani 1 1 d . . .
H33 H 0.5560 0.0515 0.8614 0.134 Uiso 1 1 calc R . .
C34 C 0.3538(17) 0.0261(4) 0.90216(14) 0.131(3) Uani 1 1 d . . .
H34A H 0.4583 -0.0166 0.9100 0.157 Uiso 1 1 calc R . .
H34B H 0.1929 0.0088 0.9063 0.157 Uiso 1 1 calc R . .
C35 C 0.4029(14) 0.1042(4) 0.92158(14) 0.103(2) Uani 1 1 d . . .
H35A H 0.3742 0.0947 0.9452 0.124 Uiso 1 1 calc R . .
H35B H 0.5675 0.1188 0.9189 0.124 Uiso 1 1 calc R . .
C36 C 0.2504(9) 0.1746(3) 0.90984(10) 0.0570(13) Uani 1 1 d . . .
H36 H 0.0863 0.1568 0.9123 0.068 Uiso 1 1 calc R . .
C37 C 0.332(2) -0.0394(4) 0.84528(17) 0.191(5) Uani 1 1 d . . .
H37A H 0.3548 -0.0296 0.8218 0.286 Uiso 1 1 calc R . .
H37B H 0.1707 -0.0546 0.8492 0.286 Uiso 1 1 calc R . .
H37C H 0.4339 -0.0827 0.8524 0.286 Uiso 1 1 calc R . .
C38 C 0.2777(9) 0.2513(3) 0.93113(10) 0.0641(15) Uani 1 1 d . . .
H38 H 0.1736 0.2928 0.9215 0.077 Uiso 1 1 calc R . .
C39 C 0.5253(11) 0.2869(4) 0.93153(16) 0.106(2) Uani 1 1 d . . .
H39A H 0.5774 0.2958 0.9090 0.160 Uiso 1 1 calc R . .
H39B H 0.6304 0.2496 0.9425 0.160 Uiso 1 1 calc R . .
H39C H 0.5242 0.3378 0.9434 0.160 Uiso 1 1 calc R . .
C40 C 0.1927(12) 0.2359(4) 0.96730(11) 0.099(2) Uani 1 1 d . . .
H40A H 0.1989 0.2860 0.9797 0.148 Uiso 1 1 calc R . .
H40B H 0.2929 0.1962 0.9778 0.148 Uiso 1 1 calc R . .
H40C H 0.0336 0.2161 0.9669 0.148 Uiso 1 1 calc R . .
H1 H 0.292(8) 0.454(3) 0.9097(11) 0.086(15) Uiso 1 1 d . . .
H21 H 0.232(7) 0.341(2) 0.8678(9) 0.052(12) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.473(3) . ?
P1 C1 1.790(4) . ?
P1 C11 1.801(4) . ?
P2 O2 1.461(4) . ?
P2 C31 1.783(4) . ?
P2 C21 1.794(4) . ?
C1 C10 1.362(6) . ?
C1 C2 1.409(6) . ?
C2 C3 1.361(5) . ?
C3 C4 1.410(6) . ?
C4 C5 1.404(6) . ?
C4 C9 1.417(6) . ?
C5 C6 1.350(7) . ?
C6 C7 1.401(8) . ?
C7 C8 1.370(7) . ?
C8 C9 1.418(6) . ?
C9 C10 1.417(6) . ?
C11 C12 1.532(6) . ?
C11 C16 1.544(5) . ?
C12 C13 1.496(7) . ?
C13 C14 1.516(7) . ?
C13 C17 1.533(7) . ?
C14 C15 1.517(7) . ?
C15 C16 1.536(7) . ?
C16 C18 1.530(6) . ?
C18 C19 1.522(7) . ?
C18 C20 1.524(7) . ?
C21 C30 1.349(5) . ?
C21 C22 1.405(6) . ?
C22 C23 1.370(6) . ?
C23 C24 1.399(6) . ?
C24 C29 1.400(6) . ?
C24 C25 1.407(6) . ?
C25 C26 1.354(7) . ?
C26 C27 1.385(8) . ?
C27 C28 1.360(7) . ?
C28 C29 1.399(6) . ?
C29 C30 1.427(5) . ?
C31 C32 1.508(6) . ?
C31 C36 1.553(6) . ?
C32 C33 1.495(7) . ?
C33 C34 1.508(7) . ?
C33 C37 1.538(9) . ?
C34 C35 1.523(8) . ?
C35 C36 1.516(7) . ?
C36 C38 1.526(6) . ?
C38 C39 1.521(8) . ?
C38 C40 1.543(6) . ?

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
O1 P1 C1 113.2(2) . . ?
O1 P1 C11 115.1(2) . . ?
C1 P1 C11 107.9(2) . . ?
O2 P2 C31 115.1(2) . . ?
O2 P2 C21 113.6(2) . . ?
C31 P2 C21 106.7(2) . . ?
C10 C1 C2 119.1(4) . . ?
C10 C1 P1 119.7(3) . . ?
C2 C1 P1 120.9(3) . . ?
C3 C2 C1 120.8(4) . . ?
C2 C3 C4 121.6(4) . . ?
C5 C4 C3 123.6(5) . . ?
C5 C4 C9 118.6(4) . . ?
C3 C4 C9 117.8(4) . . ?
C6 C5 C4 121.8(5) . . ?
C5 C6 C7 119.5(5) . . ?
C8 C7 C6 121.5(5) . . ?
C7 C8 C9 119.3(5) . . ?
C4 C9 C10 119.3(4) . . ?
C4 C9 C8 119.2(4) . . ?
C10 C9 C8 121.4(5) . . ?
C1 C10 C9 121.4(4) . . ?
C12 C11 C16 111.1(3) . . ?
C12 C11 P1 110.1(3) . . ?
C16 C11 P1 112.8(3) . . ?
C13 C12 C11 112.8(4) . . ?
C12 C13 C14 110.7(5) . . ?
C12 C13 C17 112.1(6) . . ?
C14 C13 C17 111.8(5) . . ?
C13 C14 C15 111.4(4) . . ?
C14 C15 C16 112.3(5) . . ?
C18 C16 C15 112.8(4) . . ?
C18 C16 C11 114.7(4) . . ?
C15 C16 C11 108.1(4) . . ?
C19 C18 C20 111.3(5) . . ?
C19 C18 C16 113.4(4) . . ?
C20 C18 C16 112.0(4) . . ?
C30 C21 C22 120.1(4) . . ?
C30 C21 P2 120.2(3) . . ?
C22 C21 P2 119.7(3) . . ?
C23 C22 C21 119.5(4) . . ?
C22 C23 C24 121.7(5) . . ?
C29 C24 C23 118.9(4) . . ?
C29 C24 C25 118.1(4) . . ?
C23 C24 C25 123.0(5) . . ?
C26 C25 C24 121.4(5) . . ?
C25 C26 C27 120.0(5) . . ?
C28 C27 C26 120.4(5) . . ?
C27 C28 C29 120.5(5) . . ?
C24 C29 C28 119.5(4) . . ?
C24 C29 C30 118.4(4) . . ?
C28 C29 C30 122.1(4) . . ?
C21 C30 C29 121.4(4) . . ?
C32 C31 C36 109.6(4) . . ?
C32 C31 P2 110.6(3) . . ?
C36 C31 P2 113.8(3) . . ?
C33 C32 C31 114.4(5) . . ?
C32 C33 C34 110.0(5) . . ?
C32 C33 C37 111.5(6) . . ?
C34 C33 C37 111.4(6) . . ?
C33 C34 C35 111.2(5) . . ?
C36 C35 C34 112.2(5) . . ?
C35 C36 C38 113.4(4) . . ?
C35 C36 C31 108.8(4) . . ?
C38 C36 C31 114.5(4) . . ?
C39 C38 C36 114.6(4) . . ?
C39 C38 C40 109.9(5) . . ?
C36 C38 C40 110.8(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_180922c
_database_code_depnum_ccdc_archive 'CCDC 1877581'
loop_
_audit_author_name
_audit_author_address
'Bingxia Yan'
;Liaocheng Universuity
China
;
_audit_update_record             
;
2018-11-07 deposited with the CCDC.	2020-05-28 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            'C34 H44 B O2 P'
_chemical_formula_weight         526.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   8.8610(7)
_cell_length_b                   8.9222(8)
_cell_length_c                   11.1927(9)
_cell_angle_alpha                76.371(2)
_cell_angle_beta                 78.494(2)
_cell_angle_gamma                65.5380(10)
_cell_volume                     777.57(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1234
_cell_measurement_theta_min      2.542
_cell_measurement_theta_max      20.257

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   0.970
_exptl_transmission_factor_max   0.978
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3976
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.542
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.601
_diffrn_reflns_point_group_measured_fraction_full 0.585
_reflns_number_total             3310
_reflns_number_gt                2525
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.227
_reflns_Friedel_fraction_max     0.223
_reflns_Friedel_fraction_full    0.217

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0556P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 445 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.28(13)
_chemical_absolute_configuration R
_refine_ls_number_reflns         3310
_refine_ls_number_parameters     348
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.953
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.91050(14) 0.16241(13) 0.42528(10) 0.0508(3) Uani 1 1 d . . . . .
B1 B 1.0194(8) 0.2410(8) 0.5114(6) 0.0712(17) Uani 1 1 d . . . . .
H1A H 1.0532 0.3245 0.4562 0.107 Uiso 1 1 calc R U . . .
H1B H 1.1159 0.1495 0.5420 0.107 Uiso 1 1 calc R U . . .
H1C H 0.9442 0.2886 0.5795 0.107 Uiso 1 1 calc R U . . .
O1 O 0.7599(4) 0.3109(3) 0.3516(2) 0.0527(8) Uani 1 1 d . . . . .
O2 O 1.0672(4) 0.4782(5) 0.1707(3) 0.0732(10) Uani 1 1 d D . . . .
H2 H 1.1818 0.4449 0.1488 0.088 Uiso 1 1 d R U . . .
C1 C 0.7026(8) 0.4063(6) -0.1497(5) 0.0688(15) Uani 1 1 d . . . . .
H1 H 0.7573 0.3643 -0.2219 0.083 Uiso 1 1 calc R U . . .
C2 C 0.5348(9) 0.4508(7) -0.1242(6) 0.0800(17) Uani 1 1 d . . . . .
H2A H 0.4762 0.4372 -0.1784 0.096 Uiso 1 1 calc R U . . .
C3 C 0.4498(6) 0.5167(6) -0.0175(5) 0.0689(15) Uani 1 1 d . . . . .
H3 H 0.3347 0.5481 -0.0016 0.083 Uiso 1 1 calc R U . . .
C4 C 0.5351(6) 0.5357(6) 0.0646(4) 0.0581(13) Uani 1 1 d . . . . .
H4 H 0.4773 0.5780 0.1362 0.070 Uiso 1 1 calc R U . . .
C5 C 0.7099(6) 0.4911(5) 0.0408(4) 0.0456(10) Uani 1 1 d . . . . .
C6 C 0.7954(6) 0.4231(5) -0.0677(4) 0.0523(12) Uani 1 1 d . . . . .
C7 C 0.9702(7) 0.3778(6) -0.0925(4) 0.0636(14) Uani 1 1 d . . . . .
H7 H 1.0267 0.3349 -0.1641 0.076 Uiso 1 1 calc R U . . .
C8 C 1.0568(6) 0.3962(6) -0.0129(4) 0.0627(13) Uani 1 1 d . . . . .
H8 H 1.1719 0.3646 -0.0299 0.075 Uiso 1 1 calc R U . . .
C9 C 0.9724(6) 0.4631(5) 0.0958(4) 0.0525(12) Uani 1 1 d D . . . .
C10 C 0.8033(5) 0.5100(5) 0.1234(4) 0.0430(10) Uani 1 1 d . . . . .
C11 C 0.6398(6) 0.8729(6) 0.1195(5) 0.0629(13) Uani 1 1 d . . . . .
H11 H 0.6905 0.8306 0.0468 0.076 Uiso 1 1 calc R U . . .
C12 C 0.5656(7) 1.0427(6) 0.1151(5) 0.0771(16) Uani 1 1 d . . . . .
H12 H 0.5681 1.1141 0.0400 0.093 Uiso 1 1 calc R U . . .
C13 C 0.4866(7) 1.1088(6) 0.2226(6) 0.0769(17) Uani 1 1 d . . . . .
H13 H 0.4370 1.2240 0.2188 0.092 Uiso 1 1 calc R U . . .
C14 C 0.4813(6) 1.0069(6) 0.3323(5) 0.0649(14) Uani 1 1 d . . . . .
H14 H 0.4272 1.0527 0.4032 0.078 Uiso 1 1 calc R U . . .
C15 C 0.5581(6) 0.8296(5) 0.3406(4) 0.0502(11) Uani 1 1 d . . . . .
C16 C 0.6407(6) 0.7612(5) 0.2322(4) 0.0473(11) Uani 1 1 d . . . . .
C17 C 0.7157(6) 0.5828(5) 0.2380(4) 0.0435(11) Uani 1 1 d . . . . .
C18 C 0.7035(6) 0.4829(5) 0.3503(4) 0.0478(11) Uani 1 1 d . . . . .
C19 C 0.6246(6) 0.5492(6) 0.4586(4) 0.0615(14) Uani 1 1 d . . . . .
H19 H 0.6200 0.4782 0.5336 0.074 Uiso 1 1 calc R U . . .
C20 C 0.5544(7) 0.7190(6) 0.4538(4) 0.0629(13) Uani 1 1 d . . . . .
H20 H 0.5035 0.7622 0.5261 0.076 Uiso 1 1 calc R U . . .
C21 C 1.0470(6) 0.0657(6) 0.2993(4) 0.0564(12) Uani 1 1 d . . . . .
H21A H 1.1042 0.1381 0.2548 0.068 Uiso 1 1 calc R U . . .
H21B H 1.1311 -0.0378 0.3346 0.068 Uiso 1 1 calc R U . . .
C22 C 0.9728(6) 0.0252(6) 0.2040(4) 0.0602(13) Uani 1 1 d . . . . .
H22A H 0.8915 0.1276 0.1645 0.072 Uiso 1 1 calc R U . . .
H22B H 0.9155 -0.0481 0.2460 0.072 Uiso 1 1 calc R U . . .
C23 C 1.1096(7) -0.0599(7) 0.1044(5) 0.0833(18) Uani 1 1 d . . . . .
H23A H 1.1764 0.0067 0.0715 0.100 Uiso 1 1 calc R U . . .
H23B H 1.1823 -0.1684 0.1436 0.100 Uiso 1 1 calc R U . . .
C24 C 1.0449(9) -0.0838(8) -0.0024(6) 0.104(2) Uani 1 1 d . . . . .
H24A H 0.9996 -0.1686 0.0258 0.155 Uiso 1 1 calc R U . . .
H24B H 1.1348 -0.1174 -0.0670 0.155 Uiso 1 1 calc R U . . .
H24C H 0.9593 0.0194 -0.0338 0.155 Uiso 1 1 calc R U . . .
C25 C 0.8069(6) 0.0261(5) 0.5220(4) 0.0492(11) Uani 1 1 d . . . . .
H25 H 0.7867 -0.0338 0.4678 0.059 Uiso 1 1 calc R U . . .
C26 C 0.9148(6) -0.1055(6) 0.6217(4) 0.0616(13) Uani 1 1 d . . . . .
H26 H 0.9321 -0.0426 0.6750 0.074 Uiso 1 1 calc R U . . .
C27 C 0.8138(8) -0.2051(7) 0.7043(6) 0.0850(18) Uani 1 1 d . . . . .
H27A H 0.7924 -0.2679 0.6543 0.102 Uiso 1 1 calc R U . . .
H27B H 0.8800 -0.2845 0.7681 0.102 Uiso 1 1 calc R U . . .
C28 C 0.6483(7) -0.0941(7) 0.7653(5) 0.0767(16) Uani 1 1 d . . . . .
H28A H 0.5894 -0.1626 0.8145 0.092 Uiso 1 1 calc R U . . .
H28B H 0.6691 -0.0371 0.8202 0.092 Uiso 1 1 calc R U . . .
C29 C 0.5403(6) 0.0347(6) 0.6684(4) 0.0588(13) Uani 1 1 d . . . . .
H29 H 0.5151 -0.0259 0.6177 0.071 Uiso 1 1 calc R U . . .
C30 C 0.6369(6) 0.1341(6) 0.5835(4) 0.0525(11) Uani 1 1 d . . . . .
H30A H 0.6548 0.2018 0.6313 0.063 Uiso 1 1 calc R U . . .
H30B H 0.5690 0.2095 0.5193 0.063 Uiso 1 1 calc R U . . .
C31 C 0.3756(7) 0.1486(7) 0.7283(5) 0.0767(16) Uani 1 1 d . . . . .
H31A H 0.3971 0.2043 0.7827 0.115 Uiso 1 1 calc R U . . .
H31B H 0.3136 0.0832 0.7748 0.115 Uiso 1 1 calc R U . . .
H31C H 0.3121 0.2301 0.6653 0.115 Uiso 1 1 calc R U . . .
C32 C 1.0897(6) -0.2222(7) 0.5731(5) 0.0691(15) Uani 1 1 d . . . . .
H32 H 1.1443 -0.1503 0.5202 0.083 Uiso 1 1 calc R U . . .
C33 C 1.0883(9) -0.3394(8) 0.4929(7) 0.109(2) Uani 1 1 d . . . . .
H33A H 1.0531 -0.4244 0.5443 0.164 Uiso 1 1 calc R U . . .
H33B H 1.1984 -0.3907 0.4521 0.164 Uiso 1 1 calc R U . . .
H33C H 1.0123 -0.2764 0.4320 0.164 Uiso 1 1 calc R U . . .
C34 C 1.1969(8) -0.3218(9) 0.6791(6) 0.113(2) Uani 1 1 d . . . . .
H34A H 1.2130 -0.2461 0.7189 0.169 Uiso 1 1 calc R U . . .
H34B H 1.3032 -0.3965 0.6466 0.169 Uiso 1 1 calc R U . . .
H34C H 1.1414 -0.3851 0.7381 0.169 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 O1 1.636(3) . ?
P1 C21 1.795(5) . ?
P1 C25 1.844(5) . ?
P1 B1 1.898(5) . ?
O1 C18 1.401(5) . ?
O2 C9 1.362(5) . ?
C1 C2 1.358(8) . ?
C1 C6 1.417(7) . ?
C2 C3 1.395(8) . ?
C3 C4 1.378(6) . ?
C4 C5 1.416(6) . ?
C5 C6 1.420(6) . ?
C5 C10 1.436(6) . ?
C6 C7 1.415(7) . ?
C7 C8 1.363(7) . ?
C8 C9 1.416(6) . ?
C9 C10 1.369(6) . ?
C10 C17 1.500(6) . ?
C11 C12 1.372(7) . ?
C11 C16 1.410(6) . ?
C12 C13 1.393(8) . ?
C13 C14 1.349(7) . ?
C14 C15 1.428(6) . ?
C15 C20 1.414(6) . ?
C15 C16 1.416(6) . ?
C16 C17 1.439(6) . ?
C17 C18 1.372(6) . ?
C18 C19 1.402(6) . ?
C19 C20 1.371(6) . ?
C21 C22 1.536(6) . ?
C22 C23 1.545(7) . ?
C23 C24 1.516(7) . ?
C25 C30 1.539(6) . ?
C25 C26 1.555(6) . ?
C26 C32 1.541(7) . ?
C26 C27 1.545(8) . ?
C27 C28 1.521(7) . ?
C28 C29 1.526(6) . ?
C29 C31 1.522(7) . ?
C29 C30 1.526(6) . ?
C32 C33 1.536(8) . ?
C32 C34 1.534(7) . ?

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
O1 P1 C21 100.80(19) . . ?
O1 P1 C25 102.87(19) . . ?
C21 P1 C25 110.6(2) . . ?
O1 P1 B1 114.0(2) . . ?
C21 P1 B1 111.7(3) . . ?
C25 P1 B1 115.6(2) . . ?
C18 O1 P1 126.8(3) . . ?
C2 C1 C6 120.9(5) . . ?
C1 C2 C3 120.5(5) . . ?
C4 C3 C2 120.5(5) . . ?
C3 C4 C5 120.5(4) . . ?
C4 C5 C6 118.6(4) . . ?
C4 C5 C10 122.2(4) . . ?
C6 C5 C10 119.2(4) . . ?
C7 C6 C1 121.8(5) . . ?
C7 C6 C5 119.1(4) . . ?
C1 C6 C5 119.0(5) . . ?
C8 C7 C6 120.9(4) . . ?
C7 C8 C9 120.3(5) . . ?
O2 C9 C10 122.0(4) . . ?
O2 C9 C8 116.9(4) . . ?
C10 C9 C8 121.1(4) . . ?
C9 C10 C5 119.5(4) . . ?
C9 C10 C17 120.3(4) . . ?
C5 C10 C17 120.2(4) . . ?
C12 C11 C16 121.3(5) . . ?
C11 C12 C13 120.3(5) . . ?
C14 C13 C12 120.5(5) . . ?
C13 C14 C15 120.7(5) . . ?
C20 C15 C16 118.6(4) . . ?
C20 C15 C14 122.3(4) . . ?
C16 C15 C14 119.2(4) . . ?
C11 C16 C15 117.9(4) . . ?
C11 C16 C17 121.9(4) . . ?
C15 C16 C17 120.1(4) . . ?
C18 C17 C16 118.3(4) . . ?
C18 C17 C10 121.5(4) . . ?
C16 C17 C10 120.2(4) . . ?
C17 C18 C19 122.1(4) . . ?
C17 C18 O1 117.4(4) . . ?
C19 C18 O1 120.3(4) . . ?
C20 C19 C18 119.9(4) . . ?
C19 C20 C15 121.1(4) . . ?
C22 C21 P1 119.0(3) . . ?
C21 C22 C23 111.4(4) . . ?
C24 C23 C22 114.8(5) . . ?
C30 C25 C26 110.3(4) . . ?
C30 C25 P1 109.5(3) . . ?
C26 C25 P1 112.7(3) . . ?
C32 C26 C27 111.6(4) . . ?
C32 C26 C25 116.0(4) . . ?
C27 C26 C25 109.2(4) . . ?
C28 C27 C26 112.9(5) . . ?
C29 C28 C27 110.9(4) . . ?
C28 C29 C31 111.5(4) . . ?
C28 C29 C30 110.1(4) . . ?
C31 C29 C30 111.7(4) . . ?
C29 C30 C25 114.4(4) . . ?
C33 C32 C34 110.7(5) . . ?
C33 C32 C26 114.2(5) . . ?
C34 C32 C26 111.3(5) . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.034

_shelxl_version_number           2014/6



