# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1945773'
loop_
_audit_author_name
_audit_author_address
'Zeyan Zeyan Zhuang'
;South China University of Technology
China
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2020-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H27 N2 O2 P'
_chemical_formula_sum            'C33 H27 N2 O2 P'
_chemical_formula_weight         514.53

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   10.6898(7)
_cell_length_b                   11.7750(8)
_cell_length_c                   11.9913(7)
_cell_angle_alpha                71.708(2)
_cell_angle_beta                 65.4407(19)
_cell_angle_gamma                89.239(2)
_cell_volume                     1291.40(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5820
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.09

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6722
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'TWINABS (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4543
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.114
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_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             4543
_reflns_number_gt                3587
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+1.7064P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4543
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.8250(3) 0.6784(3) 0.3871(3) 0.0216(7) Uani 1 1 d . . . . .
C2 C 0.9081(3) 0.7689(3) 0.3803(3) 0.0205(7) Uani 1 1 d . . . . .
C3 C 0.8337(3) 0.8586(3) 0.4389(3) 0.0210(7) Uani 1 1 d . . . . .
C4 C 0.6882(3) 0.8325(3) 0.4957(3) 0.0231(7) Uani 1 1 d . . . . .
C5 C 0.6042(4) 0.9076(3) 0.5520(3) 0.0271(8) Uani 1 1 d . . . . .
H5 H 0.5061 0.8883 0.5910 0.033 Uiso 1 1 calc R U . . .
C6 C 0.6647(4) 1.0122(3) 0.5510(4) 0.0290(8) Uani 1 1 d . . . . .
H6 H 0.6078 1.0651 0.5888 0.035 Uiso 1 1 calc R U . . .
C7 C 0.8067(4) 1.0385(3) 0.4952(4) 0.0298(8) Uani 1 1 d . . . . .
H7 H 0.8472 1.1102 0.4944 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8924(4) 0.9623(3) 0.4398(3) 0.0261(8) Uani 1 1 d . . . . .
H8 H 0.9904 0.9811 0.4029 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6662(4) 0.5689(4) 0.6905(4) 0.0436(11) Uani 1 1 d . . . . .
H9A H 0.6935 0.6446 0.6991 0.052 Uiso 1 1 calc R U . . .
H9B H 0.7517 0.5363 0.6461 0.052 Uiso 1 1 calc R U . . .
C10 C 0.5791(5) 0.4795(4) 0.8220(4) 0.0548(13) Uani 1 1 d . . . . .
H10A H 0.4943 0.5120 0.8650 0.082 Uiso 1 1 calc R U . . .
H10B H 0.6314 0.4636 0.8746 0.082 Uiso 1 1 calc R U . . .
H10C H 0.5545 0.4041 0.8128 0.082 Uiso 1 1 calc R U . . .
C11 C 0.9107(3) 0.3902(3) 0.2278(3) 0.0229(8) Uani 1 1 d . . . . .
C12 C 1.0176(3) 0.4791(3) 0.1939(3) 0.0253(8) Uani 1 1 d . . . . .
H12 H 1.1090 0.4769 0.1333 0.030 Uiso 1 1 calc R U . . .
C13 C 0.9927(3) 0.5702(3) 0.2471(3) 0.0253(8) Uani 1 1 d . . . . .
H13 H 1.0679 0.6288 0.2231 0.030 Uiso 1 1 calc R U . . .
C14 C 0.8596(3) 0.5788(3) 0.3355(3) 0.0202(7) Uani 1 1 d . . . . .
C15 C 0.7539(3) 0.4873(3) 0.3702(3) 0.0259(8) Uani 1 1 d . . . . .
H15 H 0.6624 0.4891 0.4306 0.031 Uiso 1 1 calc R U . . .
C16 C 0.7787(3) 0.3953(3) 0.3195(4) 0.0279(8) Uani 1 1 d . . . . .
H16 H 0.7047 0.3340 0.3473 0.033 Uiso 1 1 calc R U . . .
C17 C 1.0741(3) 0.2679(3) 0.1201(3) 0.0241(8) Uani 1 1 d . . . . .
C18 C 1.1415(4) 0.2769(4) -0.0090(4) 0.0338(9) Uani 1 1 d . . . . .
H18 H 1.0964 0.3041 -0.0643 0.041 Uiso 1 1 calc R U . . .
C19 C 1.2745(4) 0.2465(4) -0.0587(4) 0.0352(9) Uani 1 1 d . . . . .
H19 H 1.3199 0.2517 -0.1474 0.042 Uiso 1 1 calc R U . . .
C20 C 1.3404(4) 0.2087(3) 0.0211(4) 0.0315(9) Uani 1 1 d . . . . .
H20 H 1.4321 0.1890 -0.0129 0.038 Uiso 1 1 calc R U . . .
C21 C 1.2733(4) 0.1996(3) 0.1506(4) 0.0296(8) Uani 1 1 d . . . . .
H21 H 1.3187 0.1727 0.2056 0.036 Uiso 1 1 calc R U . . .
C22 C 1.1406(3) 0.2292(3) 0.2007(3) 0.0250(8) Uani 1 1 d . . . . .
H22 H 1.0950 0.2232 0.2897 0.030 Uiso 1 1 calc R U . . .
C23 C 0.8319(3) 0.2401(3) 0.1573(3) 0.0246(8) Uani 1 1 d . . . . .
C24 C 0.7325(4) 0.3010(3) 0.1262(3) 0.0292(8) Uani 1 1 d . . . . .
H24 H 0.7349 0.3852 0.1115 0.035 Uiso 1 1 calc R U . . .
C25 C 0.6300(4) 0.2401(4) 0.1162(4) 0.0344(9) Uani 1 1 d . . . . .
H25 H 0.5622 0.2828 0.0953 0.041 Uiso 1 1 calc R U . . .
C26 C 0.6253(4) 0.1182(4) 0.1364(4) 0.0360(9) Uani 1 1 d . . . . .
H26 H 0.5539 0.0767 0.1304 0.043 Uiso 1 1 calc R U . . .
C27 C 0.7244(4) 0.0568(4) 0.1651(4) 0.0389(10) Uani 1 1 d . . . . .
H27 H 0.7220 -0.0272 0.1783 0.047 Uiso 1 1 calc R U . . .
C28 C 0.8282(4) 0.1173(3) 0.1752(4) 0.0317(9) Uani 1 1 d . . . . .
H28 H 0.8969 0.0746 0.1942 0.038 Uiso 1 1 calc R U . . .
C29 C 1.2825(4) 0.8969(3) 0.1610(4) 0.0328(9) Uani 1 1 d . . . . .
H29 H 1.3338 0.9598 0.0805 0.039 Uiso 1 1 calc R U . . .
C30 C 1.1398(4) 0.8786(3) 0.2072(4) 0.0304(9) Uani 1 1 d . . . . .
H30 H 1.0953 0.9278 0.1594 0.037 Uiso 1 1 calc R U . . .
C31 C 1.0629(3) 0.7872(3) 0.3242(3) 0.0205(7) Uani 1 1 d . . . . .
C32 C 1.1347(3) 0.7182(3) 0.3888(3) 0.0252(8) Uani 1 1 d . . . . .
H32 H 1.0863 0.6541 0.4689 0.030 Uiso 1 1 calc R U . . .
C33 C 1.2778(4) 0.7443(4) 0.3347(4) 0.0322(9) Uani 1 1 d . . . . .
H33 H 1.3253 0.6969 0.3805 0.039 Uiso 1 1 calc R U . . .
N1 N 0.9363(3) 0.2998(3) 0.1707(3) 0.0274(7) Uani 1 1 d . . . . .
N2 N 1.3529(3) 0.8321(3) 0.2223(3) 0.0330(8) Uani 1 1 d . . . . .
O1 O 0.5499(2) 0.6994(2) 0.4158(3) 0.0356(7) Uani 1 1 d . . . . .
O2 O 0.5870(2) 0.5932(2) 0.6148(2) 0.0302(6) Uani 1 1 d . . . . .
P1 P 0.64489(9) 0.69607(9) 0.47616(9) 0.0238(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.358(5) . ?
C1 C14 1.466(5) . ?
C1 P1 1.819(3) . ?
C2 C3 1.490(5) . ?
C2 C31 1.494(4) . ?
C3 C8 1.385(5) . ?
C3 C4 1.406(4) . ?
C4 C5 1.376(5) . ?
C4 P1 1.788(3) . ?
C5 C6 1.392(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.374(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 O2 1.446(5) . ?
C9 C10 1.492(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.395(5) . ?
C11 C16 1.398(5) . ?
C11 N1 1.404(4) . ?
C12 C13 1.382(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.403(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.404(5) . ?
C15 C16 1.373(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.378(5) . ?
C17 C22 1.389(5) . ?
C17 N1 1.437(4) . ?
C18 C19 1.386(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.377(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.380(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.387(5) . ?
C23 C28 1.392(5) . ?
C23 N1 1.416(4) . ?
C24 C25 1.382(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.377(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.376(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.393(5) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 N2 1.335(5) . ?
C29 C30 1.383(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.385(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.390(5) . ?
C32 C33 1.385(5) . ?
C32 H32 0.9500 . ?
C33 N2 1.334(5) . ?
C33 H33 0.9500 . ?
O1 P1 1.466(3) . ?
O2 P1 1.586(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
C2 C1 C14 130.7(3) . . ?
C2 C1 P1 108.6(2) . . ?
C14 C1 P1 120.7(2) . . ?
C1 C2 C3 115.1(3) . . ?
C1 C2 C31 127.9(3) . . ?
C3 C2 C31 117.0(3) . . ?
C8 C3 C4 118.8(3) . . ?
C8 C3 C2 127.1(3) . . ?
C4 C3 C2 114.0(3) . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 P1 130.5(3) . . ?
C3 C4 P1 108.3(2) . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 121.3(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C3 C8 C7 119.5(3) . . ?
C3 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
O2 C9 C10 108.9(3) . . ?
O2 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
O2 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 117.5(3) . . ?
C12 C11 N1 120.6(3) . . ?
C16 C11 N1 121.9(3) . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 121.9(3) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 116.2(3) . . ?
C15 C14 C1 119.4(3) . . ?
C13 C14 C1 124.3(3) . . ?
C16 C15 C14 122.0(3) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C11 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C18 C17 C22 119.7(3) . . ?
C18 C17 N1 120.0(3) . . ?
C22 C17 N1 120.2(3) . . ?
C17 C18 C19 120.5(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 119.7(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.0(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C17 119.6(3) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
C24 C23 C28 118.6(3) . . ?
C24 C23 N1 121.7(3) . . ?
C28 C23 N1 119.7(3) . . ?
C25 C24 C23 120.6(4) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C24 120.6(4) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C27 C26 C25 119.7(3) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 C28 120.2(4) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 120.4(3) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
N2 C29 C30 124.2(4) . . ?
N2 C29 H29 117.9 . . ?
C30 C29 H29 117.9 . . ?
C29 C30 C31 119.0(4) . . ?
C29 C30 H30 120.5 . . ?
C31 C30 H30 120.5 . . ?
C30 C31 C32 117.6(3) . . ?
C30 C31 C2 120.3(3) . . ?
C32 C31 C2 122.1(3) . . ?
C33 C32 C31 119.0(3) . . ?
C33 C32 H32 120.5 . . ?
C31 C32 H32 120.5 . . ?
N2 C33 C32 123.9(3) . . ?
N2 C33 H33 118.0 . . ?
C32 C33 H33 118.0 . . ?
C11 N1 C23 122.6(3) . . ?
C11 N1 C17 119.4(3) . . ?
C23 N1 C17 118.0(3) . . ?
C33 N2 C29 116.3(3) . . ?
C9 O2 P1 120.9(2) . . ?
O1 P1 O2 110.78(15) . . ?
O1 P1 C4 117.23(16) . . ?
O2 P1 C4 107.58(14) . . ?
O1 P1 C1 118.70(15) . . ?
O2 P1 C1 106.95(15) . . ?
C4 P1 C1 93.97(15) . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.060

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

data_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1945775'
loop_
_audit_author_name
_audit_author_address
'Zeyan Zeyan Zhuang'
;South China University of Technology
China
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2020-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H27 N2 O2 P'
_chemical_formula_sum            'C33 H27 N2 O2 P'
_chemical_formula_weight         514.53

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   9.1957(6)
_cell_length_b                   10.8410(7)
_cell_length_c                   13.3381(8)
_cell_angle_alpha                100.850(2)
_cell_angle_beta                 100.343(2)
_cell_angle_gamma                93.057(2)
_cell_volume                     1279.46(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2513
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      24.84

_exptl_crystal_description       sheet
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6510
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12612
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.261
_diffrn_reflns_theta_max         25.353
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4637
_reflns_number_gt                2840
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0235P)²+0.4096P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4637
_refine_ls_number_parameters     428
_refine_ls_number_restraints     299
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.021
_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
C1 C 1.0709(3) 0.8370(2) 0.37083(18) 0.0245(6) Uani 1 1 d D . . . .
C2 C 1.0133(3) 0.8684(2) 0.27981(18) 0.0237(6) Uani 1 1 d . . . . .
C3 C 1.1188(3) 0.9510(2) 0.24168(19) 0.0244(6) Uani 1 1 d . . . . .
C4 C 1.2610(3) 0.9742(2) 0.30440(19) 0.0245(6) Uani 1 1 d . . . . .
C5 C 1.3692(3) 1.0532(2) 0.2834(2) 0.0322(7) Uani 1 1 d . . . . .
H5 H 1.4657 1.0669 0.3257 0.039 Uiso 1 1 calc R U . . .
C6 C 1.3351(3) 1.1123(2) 0.1996(2) 0.0342(7) Uani 1 1 d . . . . .
H6 H 1.4084 1.1674 0.1845 0.041 Uiso 1 1 calc R U . . .
C7 C 1.1957(3) 1.0915(2) 0.1384(2) 0.0339(7) Uani 1 1 d . . . . .
H7 H 1.1734 1.1332 0.0816 0.041 Uiso 1 1 calc R U . . .
C8 C 1.0857(3) 1.0101(2) 0.15798(19) 0.0290(6) Uani 1 1 d . . . . .
H8 H 0.9899 0.9955 0.1146 0.035 Uiso 1 1 calc R U . . .
C17 C 0.5708(3) 0.7359(2) 0.11667(19) 0.0253(6) Uani 1 1 d . . . . .
C18 C 0.6894(3) 0.7238(2) 0.06473(19) 0.0256(6) Uani 1 1 d . . . . .
H18 H 0.6729 0.6832 -0.0065 0.031 Uiso 1 1 calc R U . . .
C19 C 0.8317(3) 0.7710(2) 0.11681(18) 0.0246(6) Uani 1 1 d . . . . .
H19 H 0.9117 0.7632 0.0805 0.029 Uiso 1 1 calc R U . . .
C20 C 0.8590(3) 0.8295(2) 0.22160(18) 0.0235(6) Uani 1 1 d . . . . .
C21 C 0.7393(3) 0.8433(2) 0.27240(19) 0.0280(6) Uani 1 1 d . . . . .
H21 H 0.7552 0.8843 0.3435 0.034 Uiso 1 1 calc R U . . .
C22 C 0.5971(3) 0.7972(2) 0.21966(19) 0.0296(7) Uani 1 1 d . . . . .
H22 H 0.5163 0.8081 0.2550 0.036 Uiso 1 1 calc R U . . .
C23 C 0.3624(3) 0.7280(2) -0.02693(18) 0.0247(6) Uani 1 1 d . . . . .
C24 C 0.2898(3) 0.6441(3) -0.11583(19) 0.0313(7) Uani 1 1 d . . . . .
H24 H 0.2809 0.5562 -0.1164 0.038 Uiso 1 1 calc R U . . .
C25 C 0.2306(3) 0.6883(3) -0.2035(2) 0.0400(8) Uani 1 1 d . . . . .
H25 H 0.1797 0.6307 -0.2639 0.048 Uiso 1 1 calc R U . . .
C26 C 0.2446(3) 0.8155(3) -0.2041(2) 0.0400(8) Uani 1 1 d . . . . .
H26 H 0.2058 0.8453 -0.2652 0.048 Uiso 1 1 calc R U . . .
C27 C 0.3151(3) 0.8987(3) -0.1156(2) 0.0366(7) Uani 1 1 d . . . . .
H27 H 0.3240 0.9865 -0.1152 0.044 Uiso 1 1 calc R U . . .
C28 C 0.3728(3) 0.8555(2) -0.0277(2) 0.0309(7) Uani 1 1 d . . . . .
H28 H 0.4204 0.9139 0.0332 0.037 Uiso 1 1 calc R U . . .
C29 C 0.3386(3) 0.6094(2) 0.11168(19) 0.0259(6) Uani 1 1 d . . . . .
C30 C 0.4062(3) 0.5367(2) 0.1792(2) 0.0314(7) Uani 1 1 d . . . . .
H30 H 0.5113 0.5378 0.1940 0.038 Uiso 1 1 calc R U . . .
C31 C 0.3216(3) 0.4633(3) 0.2248(2) 0.0390(7) Uani 1 1 d . . . . .
H31 H 0.3692 0.4154 0.2718 0.047 Uiso 1 1 calc R U . . .
C32 C 0.1692(3) 0.4581(3) 0.2034(2) 0.0436(8) Uani 1 1 d . . . . .
H32 H 0.1114 0.4060 0.2341 0.052 Uiso 1 1 calc R U . . .
C33 C 0.1019(3) 0.5298(3) 0.1367(2) 0.0418(8) Uani 1 1 d . . . . .
H33 H -0.0033 0.5271 0.1214 0.050 Uiso 1 1 calc R U . . .
C34 C 0.1851(3) 0.6056(2) 0.0915(2) 0.0328(7) Uani 1 1 d . . . . .
H34 H 0.1369 0.6555 0.0465 0.039 Uiso 1 1 calc R U . . .
N2 N 0.4254(2) 0.6838(2) 0.06375(16) 0.0298(5) Uani 1 1 d . . . . .
O1 O 1.31229(19) 0.96927(16) 0.51788(13) 0.0358(5) Uani 1 1 d . . . . .
P1 P 1.26458(8) 0.89522(7) 0.41161(5) 0.02801(19) Uani 1 1 d D . . . .
O2 O 1.3565(7) 0.7793(5) 0.3840(4) 0.0288(14) Uani 0.792(7) 1 d D U P A 1
C9 C 1.4749(4) 0.7400(4) 0.4536(3) 0.0327(11) Uani 0.792(7) 1 d D U P A 1
H9A H 1.5370 0.8155 0.4964 0.039 Uiso 0.792(7) 1 calc R U P A 1
H9B H 1.5381 0.6892 0.4123 0.039 Uiso 0.792(7) 1 calc R U P A 1
C10 C 1.4195(6) 0.6640(4) 0.5237(3) 0.0565(15) Uani 0.792(7) 1 d D U P A 1
H10A H 1.3630 0.7160 0.5686 0.085 Uiso 0.792(7) 1 calc R U P A 1
H10B H 1.5039 0.6356 0.5669 0.085 Uiso 0.792(7) 1 calc R U P A 1
H10C H 1.3551 0.5906 0.4818 0.085 Uiso 0.792(7) 1 calc R U P A 1
O2' O 1.327(3) 0.763(2) 0.3894(18) 0.038(6) Uani 0.208(7) 1 d D U P A 2
C9' C 1.3704(17) 0.6906(14) 0.4677(12) 0.043(4) Uani 0.208(7) 1 d D U P A 2
H9'1 H 1.3143 0.6063 0.4470 0.052 Uiso 0.208(7) 1 calc R U P A 2
H9'2 H 1.3464 0.7333 0.5343 0.052 Uiso 0.208(7) 1 calc R U P A 2
C10' C 1.5356(16) 0.6756(17) 0.4823(14) 0.066(5) Uani 0.208(7) 1 d D U P A 2
H10D H 1.5620 0.6461 0.4143 0.099 Uiso 0.208(7) 1 calc R U P A 2
H10E H 1.5601 0.6139 0.5264 0.099 Uiso 0.208(7) 1 calc R U P A 2
H10F H 1.5913 0.7570 0.5155 0.099 Uiso 0.208(7) 1 calc R U P A 2
C13 C 0.9916(14) 0.7626(9) 0.4295(8) 0.028(3) Uani 0.62(2) 1 d D U P B 3
C14 C 0.9107(12) 0.6474(7) 0.3847(7) 0.035(2) Uani 0.62(2) 1 d D U P B 3
H14 H 0.9086 0.6105 0.3140 0.041 Uiso 0.62(2) 1 calc R U P B 3
C15 C 0.8334(14) 0.5871(8) 0.4438(7) 0.042(2) Uani 0.62(2) 1 d D U P B 3
H15 H 0.7809 0.5076 0.4116 0.051 Uiso 0.62(2) 1 calc R U P B 3
N1 N 0.8271(12) 0.6320(10) 0.5428(7) 0.038(2) Uani 0.62(2) 1 d D U P B 3
C11 C 0.911(2) 0.7402(12) 0.5865(11) 0.038(3) Uani 0.62(2) 1 d D U P B 3
H11 H 0.9145 0.7723 0.6583 0.045 Uiso 0.62(2) 1 calc R U P B 3
C12 C 0.9930(17) 0.8084(12) 0.5349(7) 0.027(3) Uani 0.62(2) 1 d D U P B 3
H12 H 1.0494 0.8852 0.5705 0.033 Uiso 0.62(2) 1 calc R U P B 3
C13' C 1.000(2) 0.7618(14) 0.4334(12) 0.026(4) Uani 0.38(2) 1 d D U P B 4
C14' C 0.9625(19) 0.6329(11) 0.4004(11) 0.033(3) Uani 0.38(2) 1 d D U P B 4
H14' H 0.9807 0.5898 0.3356 0.039 Uiso 0.38(2) 1 calc R U P B 4
C15' C 0.898(2) 0.5685(12) 0.4641(10) 0.039(3) Uani 0.38(2) 1 d D U P B 4
H15' H 0.8703 0.4808 0.4393 0.047 Uiso 0.38(2) 1 calc R U P B 4
N1' N 0.873(2) 0.6198(17) 0.5573(12) 0.042(3) Uani 0.38(2) 1 d D U P B 4
C11' C 0.903(4) 0.7454(19) 0.5873(17) 0.037(4) Uani 0.38(2) 1 d D U P B 4
H11' H 0.8763 0.7869 0.6499 0.044 Uiso 0.38(2) 1 calc R U P B 4
C12' C 0.971(3) 0.816(2) 0.5298(13) 0.031(4) Uani 0.38(2) 1 d D U P B 4
H12' H 0.9993 0.9035 0.5569 0.037 Uiso 0.38(2) 1 calc R U P B 4


_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
C1 C2 1.347(3) . ?
C1 C13 1.475(7) . ?
C1 C13' 1.479(11) . ?
C1 P1 1.808(3) . ?
C2 C20 1.487(3) . ?
C2 C3 1.503(3) . ?
C3 C8 1.384(3) . ?
C3 C4 1.403(3) . ?
C4 C5 1.379(3) . ?
C4 P1 1.796(3) . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.373(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.399(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C17 C22 1.381(3) . ?
C17 C18 1.392(3) . ?
C17 N2 1.427(3) . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.394(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(3) . ?
C21 C22 1.386(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C28 1.383(3) . ?
C23 C24 1.387(3) . ?
C23 N2 1.422(3) . ?
C24 C25 1.380(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.379(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.375(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.372(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C34 1.385(3) . ?
C29 C30 1.392(3) . ?
C29 N2 1.416(3) . ?
C30 C31 1.377(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.375(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.375(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.382(4) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
O1 P1 1.4687(17) . ?
P1 O2' 1.568(16) . ?
P1 O2 1.575(4) . ?
O2 C9 1.437(5) . ?
C9 C10 1.493(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O2' C9' 1.434(17) . ?
C9' C10' 1.518(16) . ?
C9' H9'1 0.9900 . ?
C9' H9'2 0.9900 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
C13 C14 1.390(8) . ?
C13 C12 1.398(8) . ?
C14 C15 1.378(7) . ?
C14 H14 0.9500 . ?
C15 N1 1.331(8) . ?
C15 H15 0.9500 . ?
N1 C11 1.341(10) . ?
C11 C12 1.381(8) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13' C12' 1.387(12) . ?
C13' C14' 1.388(12) . ?
C14' C15' 1.385(11) . ?
C14' H14' 0.9500 . ?
C15' N1' 1.330(11) . ?
C15' H15' 0.9500 . ?
N1' C11' 1.345(13) . ?
C11' C12' 1.384(12) . ?
C11' H11' 0.9500 . ?
C12' H12' 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
C2 C1 C13 126.0(5) . . ?
C2 C1 C13' 129.1(8) . . ?
C2 C1 P1 110.6(2) . . ?
C13 C1 P1 123.5(5) . . ?
C13' C1 P1 120.2(8) . . ?
C1 C2 C20 124.6(2) . . ?
C1 C2 C3 113.8(2) . . ?
C20 C2 C3 121.7(2) . . ?
C8 C3 C4 119.3(2) . . ?
C8 C3 C2 126.7(2) . . ?
C4 C3 C2 113.8(2) . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 P1 129.8(2) . . ?
C3 C4 P1 108.74(18) . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 121.3(3) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 118.9(2) . . ?
C3 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C22 C17 C18 118.9(2) . . ?
C22 C17 N2 121.1(2) . . ?
C18 C17 N2 119.9(2) . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 121.0(2) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C21 118.5(2) . . ?
C19 C20 C2 120.8(2) . . ?
C21 C20 C2 120.6(2) . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C17 C22 C21 121.2(2) . . ?
C17 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C28 C23 C24 119.0(2) . . ?
C28 C23 N2 120.4(2) . . ?
C24 C23 N2 120.7(2) . . ?
C25 C24 C23 119.9(3) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C27 C26 C25 119.4(3) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C23 120.8(2) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?
C34 C29 C30 118.5(2) . . ?
C34 C29 N2 121.1(2) . . ?
C30 C29 N2 120.4(2) . . ?
C31 C30 C29 120.4(3) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C30 121.0(3) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C31 C32 C33 118.8(3) . . ?
C31 C32 H32 120.6 . . ?
C33 C32 H32 120.6 . . ?
C32 C33 C34 120.9(3) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 H33 119.5 . . ?
C33 C34 C29 120.4(3) . . ?
C33 C34 H34 119.8 . . ?
C29 C34 H34 119.8 . . ?
C29 N2 C23 121.4(2) . . ?
C29 N2 C17 119.8(2) . . ?
C23 N2 C17 117.8(2) . . ?
O1 P1 O2' 115.9(8) . . ?
O1 P1 O2 114.6(2) . . ?
O1 P1 C4 118.63(11) . . ?
O2' P1 C4 111.8(9) . . ?
O2 P1 C4 103.9(2) . . ?
O1 P1 C1 117.38(11) . . ?
O2' P1 C1 95.8(11) . . ?
O2 P1 C1 106.5(3) . . ?
C4 P1 C1 92.94(12) . . ?
C9 O2 P1 125.9(4) . . ?
O2 C9 C10 112.5(5) . . ?
O2 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
O2 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9' O2' P1 123.9(17) . . ?
O2' C9' C10' 110.8(15) . . ?
O2' C9' H9'1 109.5 . . ?
C10' C9' H9'1 109.5 . . ?
O2' C9' H9'2 109.5 . . ?
C10' C9' H9'2 109.5 . . ?
H9'1 C9' H9'2 108.1 . . ?
C9' C10' H10D 109.5 . . ?
C9' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C9' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C14 C13 C12 116.7(7) . . ?
C14 C13 C1 123.2(7) . . ?
C12 C13 C1 120.1(7) . . ?
C15 C14 C13 119.5(7) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
N1 C15 C14 124.8(7) . . ?
N1 C15 H15 117.6 . . ?
C14 C15 H15 117.6 . . ?
C15 N1 C11 115.1(8) . . ?
N1 C11 C12 124.9(10) . . ?
N1 C11 H11 117.5 . . ?
C12 C11 H11 117.5 . . ?
C11 C12 C13 118.8(9) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12' C13' C14' 116.7(11) . . ?
C12' C13' C1 121.3(11) . . ?
C14' C13' C1 121.9(11) . . ?
C15' C14' C13' 118.6(11) . . ?
C15' C14' H14' 120.7 . . ?
C13' C14' H14' 120.7 . . ?
N1' C15' C14' 125.0(12) . . ?
N1' C15' H15' 117.5 . . ?
C14' C15' H15' 117.5 . . ?
C15' N1' C11' 116.3(14) . . ?
N1' C11' C12' 122.1(16) . . ?
N1' C11' H11' 119.0 . . ?
C12' C11' H11' 119.0 . . ?
C11' C12' C13' 121.0(15) . . ?
C11' C12' H12' 119.5 . . ?
C13' C12' H12' 119.5 . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.051

