# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_170915c_sq_d
_database_code_depnum_ccdc_archive 'CCDC 1920863'
loop_
_audit_author_name
_audit_author_address
'Changqiu Zhao'
;Liaocheng University
China
;
_audit_update_record             
;
2019-06-05 deposited with the CCDC.	2020-03-24 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            'C37 H40 O2 P2'
_chemical_formula_weight         578.63

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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   12.9764(11)
_cell_length_b                   14.3781(12)
_cell_length_c                   17.5765(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3279.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3285
_cell_measurement_theta_min      2.318
_cell_measurement_theta_max      21.236

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   0.932
_exptl_transmission_factor_max   0.951
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.310
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.951
_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            16603
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.317
_diffrn_reflns_theta_max         25.015
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             5766
_reflns_number_gt                3586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.969

_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-2014/6 (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)+(0.0480P)²] 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_abs_structure_details 
;
 Flack x determined using 1199 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(7)
_chemical_absolute_configuration R/S
_refine_ls_number_reflns         5766
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_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 0.52553(10) 0.36671(9) 0.71968(7) 0.0395(4) Uani 1 1 d . . . . .
P2 P 0.81167(10) 0.40278(10) 0.54249(7) 0.0448(4) Uani 1 1 d . . . . .
O1 O 0.5555(2) 0.4656(2) 0.71811(19) 0.0469(9) Uani 1 1 d . . . . .
O2 O 0.8631(3) 0.3948(3) 0.46792(18) 0.0631(11) Uani 1 1 d . . . . .
C1 C 0.5905(4) 0.3022(4) 0.7939(3) 0.0428(13) Uani 1 1 d . . . . .
C2 C 0.6512(4) 0.3490(4) 0.8461(3) 0.0519(15) Uani 1 1 d . . . . .
H2 H 0.6592 0.4131 0.8417 0.062 Uiso 1 1 calc R U . . .
C3 C 0.6997(4) 0.3027(5) 0.9043(3) 0.0649(17) Uani 1 1 d . . . . .
H3 H 0.7387 0.3353 0.9399 0.078 Uiso 1 1 calc R U . . .
C4 C 0.6901(5) 0.2074(5) 0.9095(3) 0.0736(19) Uani 1 1 d . . . . .
H4 H 0.7243 0.1754 0.9479 0.088 Uiso 1 1 calc R U . . .
C5 C 0.6295(5) 0.1590(4) 0.8575(3) 0.0679(18) Uani 1 1 d . . . . .
H5 H 0.6223 0.0948 0.8614 0.082 Uiso 1 1 calc R U . . .
C6 C 0.5803(4) 0.2072(4) 0.8003(3) 0.0527(15) Uani 1 1 d . . . . .
H6 H 0.5396 0.1751 0.7656 0.063 Uiso 1 1 calc R U . . .
C7 C 0.3876(3) 0.3478(3) 0.7288(3) 0.0350(12) Uani 1 1 d . . . . .
H7 H 0.3772 0.2858 0.7506 0.042 Uiso 1 1 calc R U . . .
C8 C 0.3382(3) 0.4198(4) 0.7836(3) 0.0465(13) Uani 1 1 d . . . . .
H8 H 0.3511 0.4813 0.7614 0.056 Uiso 1 1 calc R U . . .
C9 C 0.2218(4) 0.4069(4) 0.7849(3) 0.0598(15) Uani 1 1 d . . . . .
H9A H 0.2060 0.3477 0.8086 0.072 Uiso 1 1 calc R U . . .
H9B H 0.1915 0.4555 0.8159 0.072 Uiso 1 1 calc R U . . .
C10 C 0.1729(4) 0.4095(4) 0.7066(3) 0.0598(15) Uani 1 1 d . . . . .
H10A H 0.0993 0.3989 0.7113 0.072 Uiso 1 1 calc R U . . .
H10B H 0.1829 0.4706 0.6844 0.072 Uiso 1 1 calc R U . . .
C11 C 0.2182(4) 0.3372(4) 0.6546(3) 0.0476(14) Uani 1 1 d . . . . .
H11 H 0.2045 0.2759 0.6768 0.057 Uiso 1 1 calc R U . . .
C12 C 0.3341(4) 0.3502(3) 0.6508(3) 0.0420(13) Uani 1 1 d . . . . .
H12A H 0.3487 0.4094 0.6266 0.050 Uiso 1 1 calc R U . . .
H12B H 0.3631 0.3017 0.6190 0.050 Uiso 1 1 calc R U . . .
C13 C 0.3845(4) 0.4212(5) 0.8628(3) 0.077(2) Uani 1 1 d . . . . .
H13 H 0.4592 0.4275 0.8560 0.093 Uiso 1 1 calc R U . . .
C14 C 0.3678(6) 0.3324(6) 0.9083(4) 0.112(3) Uani 1 1 d . . . . .
H14A H 0.2954 0.3237 0.9171 0.167 Uiso 1 1 calc R U . . .
H14B H 0.4029 0.3372 0.9563 0.167 Uiso 1 1 calc R U . . .
H14C H 0.3945 0.2804 0.8804 0.167 Uiso 1 1 calc R U . . .
C15 C 0.3489(6) 0.5087(6) 0.9061(4) 0.151(4) Uani 1 1 d . . . . .
H15A H 0.3534 0.5619 0.8732 0.226 Uiso 1 1 calc R U . . .
H15B H 0.3923 0.5181 0.9497 0.226 Uiso 1 1 calc R U . . .
H15C H 0.2789 0.5007 0.9225 0.226 Uiso 1 1 calc R U . . .
C16 C 0.1714(4) 0.3395(5) 0.5763(3) 0.079(2) Uani 1 1 d . . . . .
H16A H 0.0980 0.3326 0.5802 0.118 Uiso 1 1 calc R U . . .
H16B H 0.1992 0.2896 0.5464 0.118 Uiso 1 1 calc R U . . .
H16C H 0.1872 0.3978 0.5524 0.118 Uiso 1 1 calc R U . . .
C17 C 0.5624(4) 0.3081(3) 0.6329(3) 0.0385(12) Uani 1 1 d . . . . .
H17 H 0.5429 0.2469 0.6239 0.046 Uiso 1 1 calc R U . . .
C18 C 0.6168(4) 0.3538(3) 0.5836(3) 0.0383(12) Uani 1 1 d . . . . .
C19 C 0.6718(3) 0.4034(3) 0.5362(3) 0.0378(12) Uani 1 1 d . . . . .
C20 C 0.6246(4) 0.4692(3) 0.4804(3) 0.0389(13) Uani 1 1 d . . . . .
C21 C 0.6477(4) 0.4619(4) 0.4035(3) 0.0501(14) Uani 1 1 d . . . . .
H21 H 0.6932 0.4165 0.3864 0.060 Uiso 1 1 calc R U . . .
C22 C 0.6026(5) 0.5228(4) 0.3527(4) 0.0618(17) Uani 1 1 d . . . . .
H22 H 0.6175 0.5181 0.3011 0.074 Uiso 1 1 calc R U . . .
C23 C 0.5363(5) 0.5898(5) 0.3774(4) 0.0650(17) Uani 1 1 d . . . . .
H23 H 0.5062 0.6304 0.3427 0.078 Uiso 1 1 calc R U . . .
C24 C 0.5142(4) 0.5973(4) 0.4527(4) 0.0725(18) Uani 1 1 d . . . . .
H24 H 0.4695 0.6436 0.4693 0.087 Uiso 1 1 calc R U . . .
C25 C 0.5575(4) 0.5367(4) 0.5049(3) 0.0547(15) Uani 1 1 d . . . . .
H25 H 0.5412 0.5417 0.5563 0.066 Uiso 1 1 calc R U . . .
C26 C 0.8432(4) 0.5087(3) 0.5913(3) 0.0440(14) Uani 1 1 d . . . . .
C27 C 0.9361(5) 0.5492(4) 0.5749(4) 0.0712(18) Uani 1 1 d . . . . .
H27 H 0.9785 0.5237 0.5378 0.085 Uiso 1 1 calc R U . . .
C28 C 0.9671(5) 0.6290(5) 0.6141(4) 0.086(2) Uani 1 1 d . . . . .
H28 H 1.0299 0.6568 0.6027 0.103 Uiso 1 1 calc R U . . .
C29 C 0.9055(6) 0.6659(4) 0.6689(4) 0.080(2) Uani 1 1 d . . . . .
H29 H 0.9272 0.7180 0.6958 0.096 Uiso 1 1 calc R U . . .
C30 C 0.8108(5) 0.6262(4) 0.6846(3) 0.0671(17) Uani 1 1 d . . . . .
H30 H 0.7681 0.6520 0.7215 0.081 Uiso 1 1 calc R U . . .
C31 C 0.7803(4) 0.5482(4) 0.6452(3) 0.0524(15) Uani 1 1 d . . . . .
H31 H 0.7162 0.5219 0.6553 0.063 Uiso 1 1 calc R U . . .
C32 C 0.8439(4) 0.3083(3) 0.6041(3) 0.0409(13) Uani 1 1 d . . . . .
C33 C 0.8841(4) 0.2277(4) 0.5720(3) 0.0566(15) Uani 1 1 d . . . . .
H33 H 0.8952 0.2251 0.5197 0.068 Uiso 1 1 calc R U . . .
C34 C 0.9076(5) 0.1517(4) 0.6165(4) 0.0664(18) Uani 1 1 d . . . . .
H34 H 0.9345 0.0983 0.5942 0.080 Uiso 1 1 calc R U . . .
C35 C 0.8917(4) 0.1547(5) 0.6925(4) 0.0667(18) Uani 1 1 d . . . . .
H35 H 0.9065 0.1029 0.7223 0.080 Uiso 1 1 calc R U . . .
C36 C 0.8531(4) 0.2350(4) 0.7264(3) 0.0646(17) Uani 1 1 d . . . . .
H36 H 0.8437 0.2376 0.7788 0.077 Uiso 1 1 calc R U . . .
C37 C 0.8291(4) 0.3103(4) 0.6819(3) 0.0502(14) Uani 1 1 d . . . . .
H37 H 0.8024 0.3636 0.7045 0.060 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 1.474(3) . ?
P1 C1 1.808(5) . ?
P1 C17 1.807(5) . ?
P1 C7 1.817(4) . ?
P2 O2 1.475(3) . ?
P2 C32 1.787(5) . ?
P2 C26 1.795(5) . ?
P2 C19 1.819(5) . ?
C1 C6 1.377(7) . ?
C1 C2 1.384(7) . ?
C2 C3 1.374(7) . ?
C3 C4 1.379(7) . ?
C4 C5 1.393(8) . ?
C5 C6 1.378(7) . ?
C7 C12 1.538(6) . ?
C7 C8 1.553(6) . ?
C8 C13 1.517(7) . ?
C8 C9 1.522(7) . ?
C9 C10 1.516(7) . ?
C10 C11 1.503(7) . ?
C11 C16 1.505(7) . ?
C11 C12 1.516(6) . ?
C13 C14 1.523(9) . ?
C13 C15 1.542(9) . ?
C17 C18 1.296(6) . ?
C18 C19 1.307(7) . ?
C19 C20 1.495(6) . ?
C20 C25 1.374(7) . ?
C20 C21 1.388(7) . ?
C21 C22 1.381(7) . ?
C22 C23 1.362(8) . ?
C23 C24 1.357(8) . ?
C24 C25 1.386(7) . ?
C26 C27 1.370(7) . ?
C26 C31 1.374(7) . ?
C27 C28 1.396(8) . ?
C28 C29 1.358(8) . ?
C29 C30 1.384(8) . ?
C30 C31 1.376(7) . ?
C32 C37 1.381(6) . ?
C32 C33 1.391(7) . ?
C33 C34 1.378(7) . ?
C34 C35 1.353(8) . ?
C35 C36 1.392(8) . ?
C36 C37 1.371(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 C1 112.6(2) . . ?
O1 P1 C17 111.3(2) . . ?
C1 P1 C17 104.3(2) . . ?
O1 P1 C7 113.9(2) . . ?
C1 P1 C7 108.6(2) . . ?
C17 P1 C7 105.4(2) . . ?
O2 P2 C32 112.0(2) . . ?
O2 P2 C26 112.8(2) . . ?
C32 P2 C26 107.5(2) . . ?
O2 P2 C19 113.4(2) . . ?
C32 P2 C19 105.9(2) . . ?
C26 P2 C19 104.6(2) . . ?
C6 C1 C2 118.8(5) . . ?
C6 C1 P1 121.5(4) . . ?
C2 C1 P1 119.6(4) . . ?
C3 C2 C1 121.3(6) . . ?
C2 C3 C4 119.3(6) . . ?
C3 C4 C5 120.3(6) . . ?
C6 C5 C4 119.3(6) . . ?
C1 C6 C5 121.0(5) . . ?
C12 C7 C8 110.5(4) . . ?
C12 C7 P1 111.3(3) . . ?
C8 C7 P1 111.2(3) . . ?
C13 C8 C9 112.4(4) . . ?
C13 C8 C7 114.5(4) . . ?
C9 C8 C7 109.8(4) . . ?
C10 C9 C8 113.5(4) . . ?
C11 C10 C9 111.7(4) . . ?
C10 C11 C16 112.5(4) . . ?
C10 C11 C12 109.3(4) . . ?
C16 C11 C12 110.9(5) . . ?
C11 C12 C7 113.9(4) . . ?
C8 C13 C14 114.5(6) . . ?
C8 C13 C15 110.2(6) . . ?
C14 C13 C15 112.4(6) . . ?
C18 C17 P1 118.2(4) . . ?
C17 C18 C19 177.1(5) . . ?
C18 C19 C20 122.7(4) . . ?
C18 C19 P2 120.3(4) . . ?
C20 C19 P2 116.8(3) . . ?
C25 C20 C21 119.7(5) . . ?
C25 C20 C19 120.0(5) . . ?
C21 C20 C19 120.2(5) . . ?
C22 C21 C20 119.3(5) . . ?
C23 C22 C21 120.7(6) . . ?
C24 C23 C22 120.0(6) . . ?
C23 C24 C25 120.7(6) . . ?
C20 C25 C24 119.5(6) . . ?
C27 C26 C31 119.5(5) . . ?
C27 C26 P2 117.5(5) . . ?
C31 C26 P2 123.0(4) . . ?
C26 C27 C28 120.0(6) . . ?
C29 C28 C27 120.1(6) . . ?
C28 C29 C30 120.2(6) . . ?
C31 C30 C29 119.4(6) . . ?
C26 C31 C30 120.9(5) . . ?
C37 C32 C33 118.1(5) . . ?
C37 C32 P2 123.5(4) . . ?
C33 C32 P2 118.3(4) . . ?
C34 C33 C32 120.9(5) . . ?
C35 C34 C33 120.1(6) . . ?
C34 C35 C36 120.3(6) . . ?
C37 C36 C35 119.5(6) . . ?
C36 C37 C32 121.1(5) . . ?

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_190113g_sq
_database_code_depnum_ccdc_archive 'CCDC 1920865'
loop_
_audit_author_name
_audit_author_address
'Changqiu Zhao'
;Liaocheng University
China
;
_audit_update_record             
;
2019-06-05 deposited with the CCDC.	2020-03-24 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            'C38 H42 O2 P2'
_chemical_formula_weight         592.65

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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   13.2801(12)
_cell_length_b                   14.3298(13)
_cell_length_c                   17.9616(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3418.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3433
_cell_measurement_theta_min      2.379
_cell_measurement_theta_max      20.150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.390
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.940
_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            16613
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.379
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             6010
_reflns_number_gt                3754
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.964

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0300P)²] 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_abs_structure_details 
;
 Flack x determined using 1283 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(6)
_chemical_absolute_configuration R
_refine_ls_number_reflns         6010
_refine_ls_number_parameters     383
_refine_ls_number_restraints     228
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0805
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.042
_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 0.52245(9) 0.60471(9) 0.29443(6) 0.0384(3) Uani 1 1 d . . . . .
P2 P 0.80883(9) 0.58700(10) 0.46560(6) 0.0470(4) Uani 1 1 d . . . . .
O1 O 0.5548(2) 0.50545(19) 0.30085(16) 0.0436(8) Uani 1 1 d . . . . .
O2 O 0.8605(2) 0.5983(3) 0.53804(15) 0.0628(10) Uani 1 1 d . . . . .
C1 C 0.5816(3) 0.6649(3) 0.2185(2) 0.0388(11) Uani 1 1 d . U . . .
C2 C 0.6491(3) 0.6187(3) 0.1730(2) 0.0482(13) Uani 1 1 d . U . . .
H2 H 0.6643 0.5564 0.1821 0.058 Uiso 1 1 calc R U . . .
C3 C 0.6945(4) 0.6646(4) 0.1139(3) 0.0559(14) Uani 1 1 d . U . . .
H3 H 0.7390 0.6318 0.0836 0.067 Uiso 1 1 calc R U . . .
C4 C 0.6758(4) 0.7564(4) 0.0988(3) 0.0563(14) Uani 1 1 d . U . . .
C5 C 0.6085(4) 0.8028(4) 0.1440(3) 0.0552(14) Uani 1 1 d . U . . .
H5 H 0.5938 0.8651 0.1344 0.066 Uiso 1 1 calc R U . . .
C6 C 0.5622(3) 0.7585(3) 0.2037(3) 0.0503(12) Uani 1 1 d . U . . .
H6 H 0.5179 0.7915 0.2340 0.060 Uiso 1 1 calc R U . . .
C7 C 0.7274(4) 0.8049(4) 0.0352(3) 0.0850(19) Uani 1 1 d . U . . .
H7A H 0.6960 0.7872 -0.0108 0.128 Uiso 1 1 calc R U . . .
H7B H 0.7972 0.7874 0.0342 0.128 Uiso 1 1 calc R U . . .
H7C H 0.7220 0.8712 0.0416 0.128 Uiso 1 1 calc R U . . .
C8 C 0.3877(3) 0.6204(3) 0.2854(2) 0.0401(12) Uani 1 1 d . U . . .
H8 H 0.3766 0.6801 0.2602 0.048 Uiso 1 1 calc R U . . .
C9 C 0.3388(3) 0.5438(3) 0.2372(2) 0.0452(12) Uani 1 1 d . U . . .
H9 H 0.3473 0.4851 0.2645 0.054 Uiso 1 1 calc R U . . .
C10 C 0.2255(3) 0.5611(4) 0.2321(2) 0.0611(15) Uani 1 1 d . U . . .
H10A H 0.2137 0.6194 0.2060 0.073 Uiso 1 1 calc R U . . .
H10B H 0.1948 0.5114 0.2032 0.073 Uiso 1 1 calc R U . . .
C11 C 0.1757(4) 0.5654(4) 0.3078(3) 0.0670(15) Uani 1 1 d . U . . .
H11A H 0.1044 0.5776 0.3016 0.080 Uiso 1 1 calc R U . . .
H11B H 0.1830 0.5055 0.3324 0.080 Uiso 1 1 calc R U . . .
C12 C 0.2213(4) 0.6403(4) 0.3558(3) 0.0573(14) Uani 1 1 d . U . . .
H12 H 0.2099 0.7002 0.3309 0.069 Uiso 1 1 calc R U . . .
C13 C 0.3354(3) 0.6263(4) 0.3623(2) 0.0505(13) Uani 1 1 d . U . . .
H13A H 0.3640 0.6778 0.3902 0.061 Uiso 1 1 calc R U . . .
H13B H 0.3486 0.5693 0.3898 0.061 Uiso 1 1 calc R U . . .
C14 C 0.3879(4) 0.5292(4) 0.1606(2) 0.0538(14) Uani 1 1 d . U . . .
H14 H 0.4607 0.5254 0.1691 0.065 Uiso 1 1 calc R U . . .
C15 C 0.3708(5) 0.6105(5) 0.1076(2) 0.092(2) Uani 1 1 d . U . . .
H15A H 0.3007 0.6142 0.0951 0.138 Uiso 1 1 calc R U . . .
H15B H 0.4097 0.6011 0.0632 0.138 Uiso 1 1 calc R U . . .
H15C H 0.3914 0.6675 0.1312 0.138 Uiso 1 1 calc R U . . .
C16 C 0.3561(4) 0.4359(4) 0.1263(3) 0.092(2) Uani 1 1 d . U . . .
H16A H 0.3613 0.3876 0.1631 0.138 Uiso 1 1 calc R U . . .
H16B H 0.3994 0.4215 0.0850 0.138 Uiso 1 1 calc R U . . .
H16C H 0.2878 0.4402 0.1092 0.138 Uiso 1 1 calc R U . . .
C17 C 0.1735(4) 0.6461(5) 0.4331(3) 0.093(2) Uani 1 1 d . U . . .
H17A H 0.1032 0.6605 0.4282 0.140 Uiso 1 1 calc R U . . .
H17B H 0.2062 0.6941 0.4614 0.140 Uiso 1 1 calc R U . . .
H17C H 0.1811 0.5873 0.4580 0.140 Uiso 1 1 calc R U . . .
C18 C 0.5602(3) 0.6718(3) 0.3752(2) 0.0420(12) Uani 1 1 d . U . . .
H18 H 0.5389 0.7332 0.3811 0.050 Uiso 1 1 calc R U . . .
C19 C 0.6173(4) 0.6326(3) 0.4246(2) 0.0383(12) Uani 1 1 d . U . . .
C20 C 0.8372(4) 0.4782(3) 0.4207(2) 0.0460(13) Uani 1 1 d . U . . .
C21 C 0.9312(4) 0.4398(4) 0.4330(3) 0.0754(17) Uani 1 1 d . U . . .
H21 H 0.9754 0.4678 0.4664 0.090 Uiso 1 1 calc R U . . .
C22 C 0.9597(5) 0.3591(5) 0.3955(4) 0.096(2) Uani 1 1 d . U . . .
H22 H 1.0225 0.3328 0.4047 0.115 Uiso 1 1 calc R U . . .
C23 C 0.8968(5) 0.3184(4) 0.3458(4) 0.0785(18) Uani 1 1 d . U . . .
H23 H 0.9175 0.2657 0.3197 0.094 Uiso 1 1 calc R U . . .
C24 C 0.8029(4) 0.3546(4) 0.3339(3) 0.0668(15) Uani 1 1 d . U . . .
H24 H 0.7591 0.3253 0.3011 0.080 Uiso 1 1 calc R U . . .
C25 C 0.7731(4) 0.4349(4) 0.3707(3) 0.0548(13) Uani 1 1 d . U . . .
H25 H 0.7096 0.4598 0.3617 0.066 Uiso 1 1 calc R U . . .
C26 C 0.8421(3) 0.6775(3) 0.4005(2) 0.0423(12) Uani 1 1 d . U . . .
C27 C 0.8901(4) 0.7563(4) 0.4287(3) 0.0605(15) Uani 1 1 d . U . . .
H27 H 0.9035 0.7608 0.4794 0.073 Uiso 1 1 calc R U . . .
C28 C 0.9178(4) 0.8273(4) 0.3816(3) 0.0752(17) Uani 1 1 d . U . . .
H28 H 0.9491 0.8802 0.4007 0.090 Uiso 1 1 calc R U . . .
C29 C 0.8995(4) 0.8206(4) 0.3064(3) 0.0715(16) Uani 1 1 d . U . . .
H29 H 0.9192 0.8684 0.2746 0.086 Uiso 1 1 calc R U . . .
C30 C 0.8518(4) 0.7429(4) 0.2787(3) 0.0620(15) Uani 1 1 d . U . . .
H30 H 0.8382 0.7386 0.2280 0.074 Uiso 1 1 calc R U . . .
C31 C 0.8241(4) 0.6712(3) 0.3257(3) 0.0530(14) Uani 1 1 d . U . . .
H31 H 0.7930 0.6183 0.3064 0.064 Uiso 1 1 calc R U . . .
C32 C 0.6723(3) 0.5888(3) 0.4730(2) 0.0394(11) Uani 1 1 d . U . . .
C33 C 0.6265(3) 0.5316(3) 0.5342(3) 0.0436(12) Uani 1 1 d . U . . .
C34 C 0.5591(4) 0.4621(4) 0.5172(3) 0.0571(14) Uani 1 1 d . U . . .
H34 H 0.5432 0.4498 0.4677 0.068 Uiso 1 1 calc R U . . .
C35 C 0.5151(4) 0.4104(4) 0.5730(3) 0.0744(16) Uani 1 1 d . U . . .
H35 H 0.4704 0.3629 0.5609 0.089 Uiso 1 1 calc R U . . .
C36 C 0.5366(4) 0.4284(4) 0.6455(3) 0.0699(16) Uani 1 1 d . U . . .
H36 H 0.5054 0.3940 0.6829 0.084 Uiso 1 1 calc R U . . .
C37 C 0.6040(4) 0.4970(4) 0.6636(3) 0.0586(15) Uani 1 1 d . U . . .
H37 H 0.6194 0.5086 0.7132 0.070 Uiso 1 1 calc R U . . .
C38 C 0.6492(4) 0.5492(3) 0.6082(2) 0.0499(13) Uani 1 1 d . U . . .
H38 H 0.6948 0.5959 0.6206 0.060 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 1.490(3) . ?
P1 C18 1.811(5) . ?
P1 C1 1.795(4) . ?
P1 C8 1.811(4) . ?
P2 O2 1.480(3) . ?
P2 C20 1.795(5) . ?
P2 C32 1.818(4) . ?
P2 C26 1.801(5) . ?
C1 C2 1.382(6) . ?
C1 C6 1.391(6) . ?
C2 C3 1.387(6) . ?
C3 C4 1.366(7) . ?
C4 C5 1.380(6) . ?
C4 C7 1.502(6) . ?
C5 C6 1.390(6) . ?
C8 C13 1.547(5) . ?
C8 C9 1.541(6) . ?
C9 C14 1.536(6) . ?
C9 C10 1.528(6) . ?
C10 C11 1.514(6) . ?
C11 C12 1.503(6) . ?
C12 C17 1.529(6) . ?
C12 C13 1.534(6) . ?
C14 C15 1.521(7) . ?
C14 C16 1.531(7) . ?
C18 C19 1.296(6) . ?
C19 C32 1.297(6) . ?
C20 C25 1.386(6) . ?
C20 C21 1.382(6) . ?
C21 C22 1.391(7) . ?
C22 C23 1.354(8) . ?
C23 C24 1.367(7) . ?
C24 C25 1.383(6) . ?
C26 C27 1.392(6) . ?
C26 C31 1.368(6) . ?
C27 C28 1.374(7) . ?
C28 C29 1.376(7) . ?
C29 C30 1.374(7) . ?
C30 C31 1.380(6) . ?
C32 C33 1.499(6) . ?
C33 C34 1.373(6) . ?
C33 C38 1.388(5) . ?
C34 C35 1.376(6) . ?
C35 C36 1.358(7) . ?
C36 C37 1.370(7) . ?
C37 C38 1.380(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 C18 111.4(2) . . ?
O1 P1 C1 113.0(2) . . ?
C18 P1 C1 103.47(19) . . ?
O1 P1 C8 114.19(19) . . ?
C18 P1 C8 106.2(2) . . ?
C1 P1 C8 107.8(2) . . ?
O2 P2 C20 113.1(2) . . ?
O2 P2 C32 113.34(19) . . ?
C20 P2 C32 104.8(2) . . ?
O2 P2 C26 112.2(2) . . ?
C20 P2 C26 106.4(2) . . ?
C32 P2 C26 106.4(2) . . ?
C2 C1 C6 118.0(4) . . ?
C2 C1 P1 120.2(4) . . ?
C6 C1 P1 121.8(4) . . ?
C1 C2 C3 120.5(5) . . ?
C4 C3 C2 122.0(5) . . ?
C3 C4 C5 117.7(5) . . ?
C3 C4 C7 120.9(5) . . ?
C5 C4 C7 121.3(5) . . ?
C6 C5 C4 121.4(5) . . ?
C5 C6 C1 120.4(4) . . ?
C13 C8 C9 110.6(4) . . ?
C13 C8 P1 111.8(3) . . ?
C9 C8 P1 112.2(3) . . ?
C14 C9 C8 114.9(4) . . ?
C14 C9 C10 112.7(4) . . ?
C8 C9 C10 109.5(4) . . ?
C11 C10 C9 112.5(4) . . ?
C12 C11 C10 111.7(4) . . ?
C11 C12 C17 113.1(4) . . ?
C11 C12 C13 110.3(4) . . ?
C17 C12 C13 110.4(4) . . ?
C8 C13 C12 112.5(4) . . ?
C15 C14 C9 113.1(4) . . ?
C15 C14 C16 112.1(4) . . ?
C9 C14 C16 111.3(4) . . ?
C19 C18 P1 118.7(4) . . ?
C18 C19 C32 176.7(5) . . ?
C25 C20 C21 118.7(5) . . ?
C25 C20 P2 123.5(4) . . ?
C21 C20 P2 117.6(4) . . ?
C20 C21 C22 119.9(6) . . ?
C23 C22 C21 120.7(6) . . ?
C24 C23 C22 120.1(6) . . ?
C23 C24 C25 120.2(6) . . ?
C24 C25 C20 120.4(5) . . ?
C27 C26 C31 119.4(5) . . ?
C27 C26 P2 117.4(4) . . ?
C31 C26 P2 123.2(4) . . ?
C26 C27 C28 119.9(5) . . ?
C29 C28 C27 120.4(5) . . ?
C28 C29 C30 119.6(5) . . ?
C31 C30 C29 120.3(5) . . ?
C26 C31 C30 120.3(5) . . ?
C19 C32 C33 121.8(4) . . ?
C19 C32 P2 121.3(3) . . ?
C33 C32 P2 116.8(3) . . ?
C34 C33 C38 119.1(4) . . ?
C34 C33 C32 119.9(4) . . ?
C38 C33 C32 121.0(4) . . ?
C33 C34 C35 120.4(5) . . ?
C36 C35 C34 120.5(5) . . ?
C35 C36 C37 120.0(5) . . ?
C36 C37 C38 120.2(5) . . ?
C37 C38 C33 119.8(5) . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.043

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_180113g
_database_code_depnum_ccdc_archive 'CCDC 1920864'
loop_
_audit_author_name
_audit_author_address
'Changqiu Zhao'
;Liaocheng University
China
;
_audit_update_record             
;
2019-06-05 deposited with the CCDC.	2020-03-24 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            'C26 H33 O3 P'
_chemical_formula_weight         424.49

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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   8.8154(7)
_cell_length_b                   11.3911(9)
_cell_length_c                   24.121(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2422.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3164
_cell_measurement_theta_min      2.455
_cell_measurement_theta_max      21.927

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   0.955
_exptl_transmission_factor_max   0.966
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.967
_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            11725
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.459
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             4272
_reflns_number_gt                3059
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.971

_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 SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0513P)²+0.1562P] 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_abs_structure_details 
;
 Flack x determined using 1080 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(7)
_chemical_absolute_configuration R
_refine_ls_number_reflns         4272
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.64625(11) 0.65025(8) 0.76456(4) 0.0393(3) Uani 1 1 d . . . . .
O1 O 0.5669(3) 0.7541(2) 0.74153(12) 0.0525(8) Uani 1 1 d . . . . .
O2 O 0.6459(3) 0.4180(2) 0.75782(12) 0.0527(7) Uani 1 1 d . . . . .
H2 H 0.5895 0.3610 0.7551 0.079 Uiso 1 1 calc R U . . .
O3 O 0.7903(3) 0.6541(3) 0.40600(12) 0.0650(8) Uani 1 1 d . . . . .
C1 C 0.8454(4) 0.6511(3) 0.74832(14) 0.0414(9) Uani 1 1 d . . . . .
C2 C 0.9431(4) 0.5656(4) 0.7679(2) 0.0556(11) Uani 1 1 d . . . . .
H2A H 0.9065 0.5057 0.7904 0.067 Uiso 1 1 calc R U . . .
C3 C 1.0953(5) 0.5694(4) 0.7540(2) 0.0693(15) Uani 1 1 d . . . . .
H3 H 1.1608 0.5117 0.7671 0.083 Uiso 1 1 calc R U . . .
C4 C 1.1488(6) 0.6557(5) 0.7217(2) 0.0746(14) Uani 1 1 d . . . . .
H4 H 1.2517 0.6579 0.7132 0.090 Uiso 1 1 calc R U . . .
C5 C 1.0557(6) 0.7398(4) 0.7013(2) 0.0716(15) Uani 1 1 d . . . . .
H5 H 1.0945 0.7988 0.6787 0.086 Uiso 1 1 calc R U . . .
C6 C 0.9007(5) 0.7378(4) 0.71413(18) 0.0549(12) Uani 1 1 d . . . . .
H6 H 0.8359 0.7945 0.6997 0.066 Uiso 1 1 calc R U . . .
C7 C 0.6161(4) 0.6323(3) 0.83882(15) 0.0429(10) Uani 1 1 d . . . . .
H7 H 0.6899 0.5751 0.8527 0.051 Uiso 1 1 calc R U . . .
C8 C 0.6373(5) 0.7486(3) 0.87131(17) 0.0507(10) Uani 1 1 d . . . . .
H8 H 0.5602 0.8030 0.8573 0.061 Uiso 1 1 calc R U . . .
C9 C 0.5997(6) 0.7268(4) 0.93251(18) 0.0656(14) Uani 1 1 d . . . . .
H9A H 0.6718 0.6711 0.9477 0.079 Uiso 1 1 calc R U . . .
H9B H 0.6101 0.7998 0.9529 0.079 Uiso 1 1 calc R U . . .
C10 C 0.4403(6) 0.6797(5) 0.9402(2) 0.0779(16) Uani 1 1 d . . . . .
H10A H 0.4216 0.6670 0.9794 0.093 Uiso 1 1 calc R U . . .
H10B H 0.3679 0.7374 0.9270 0.093 Uiso 1 1 calc R U . . .
C11 C 0.4172(5) 0.5658(4) 0.90922(18) 0.0589(12) Uani 1 1 d . . . . .
H11 H 0.4886 0.5082 0.9244 0.071 Uiso 1 1 calc R U . . .
C12 C 0.4553(4) 0.5825(4) 0.84831(17) 0.0528(11) Uani 1 1 d . . . . .
H12A H 0.3817 0.6354 0.8319 0.063 Uiso 1 1 calc R U . . .
H12B H 0.4468 0.5075 0.8295 0.063 Uiso 1 1 calc R U . . .
C13 C 0.7910(5) 0.8098(4) 0.86379(19) 0.0566(12) Uani 1 1 d . . . . .
H13 H 0.8075 0.8173 0.8238 0.068 Uiso 1 1 calc R U . . .
C14 C 0.9263(5) 0.7427(5) 0.8869(2) 0.0761(15) Uani 1 1 d . . . . .
H14A H 1.0183 0.7825 0.8770 0.114 Uiso 1 1 calc R U . . .
H14B H 0.9274 0.6647 0.8718 0.114 Uiso 1 1 calc R U . . .
H14C H 0.9184 0.7384 0.9266 0.114 Uiso 1 1 calc R U . . .
C15 C 0.7883(6) 0.9344(4) 0.8873(2) 0.0778(16) Uani 1 1 d . . . . .
H15A H 0.7815 0.9310 0.9270 0.117 Uiso 1 1 calc R U . . .
H15B H 0.7021 0.9758 0.8728 0.117 Uiso 1 1 calc R U . . .
H15C H 0.8796 0.9747 0.8769 0.117 Uiso 1 1 calc R U . . .
C16 C 0.2574(6) 0.5161(5) 0.9162(2) 0.0901(18) Uani 1 1 d . . . . .
H16A H 0.2367 0.5045 0.9549 0.135 Uiso 1 1 calc R U . . .
H16B H 0.2501 0.4424 0.8971 0.135 Uiso 1 1 calc R U . . .
H16C H 0.1850 0.5702 0.9010 0.135 Uiso 1 1 calc R U . . .
C17 C 0.5802(4) 0.5147(3) 0.73083(17) 0.0433(10) Uani 1 1 d . . . . .
H17 H 0.4697 0.5097 0.7344 0.052 Uiso 1 1 calc R U . . .
C18 C 0.6193(5) 0.5232(4) 0.67190(18) 0.0492(10) Uani 1 1 d . . . . .
C19 C 0.6562(5) 0.5405(4) 0.62516(18) 0.0516(10) Uani 1 1 d . . . . .
C20 C 0.6959(5) 0.5675(4) 0.56895(17) 0.0506(11) Uani 1 1 d . . . . .
C21 C 0.6095(5) 0.5285(4) 0.52510(18) 0.0603(12) Uani 1 1 d . . . . .
H21 H 0.5269 0.4799 0.5320 0.072 Uiso 1 1 calc R U . . .
C22 C 0.6422(5) 0.5594(4) 0.47150(18) 0.0592(11) Uani 1 1 d . . . . .
H22 H 0.5816 0.5325 0.4426 0.071 Uiso 1 1 calc R U . . .
C23 C 0.7654(5) 0.6307(4) 0.46044(17) 0.0485(10) Uani 1 1 d . . . . .
C24 C 0.8532(6) 0.6702(4) 0.50361(17) 0.0649(13) Uani 1 1 d . . . . .
H24 H 0.9363 0.7183 0.4967 0.078 Uiso 1 1 calc R U . . .
C25 C 0.8182(5) 0.6389(4) 0.55678(18) 0.0654(13) Uani 1 1 d . . . . .
H25 H 0.8786 0.6664 0.5856 0.078 Uiso 1 1 calc R U . . .
C26 C 0.9090(6) 0.7331(5) 0.3924(2) 0.0759(15) Uani 1 1 d . . . . .
H26A H 0.8858 0.8095 0.4070 0.114 Uiso 1 1 calc R U . . .
H26B H 0.9192 0.7378 0.3529 0.114 Uiso 1 1 calc R U . . .
H26C H 1.0024 0.7056 0.4083 0.114 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 1.482(3) . ?
P1 C1 1.799(4) . ?
P1 C7 1.823(4) . ?
P1 C17 1.840(4) . ?
O2 C17 1.405(4) . ?
O3 C23 1.358(5) . ?
O3 C26 1.419(5) . ?
C1 C6 1.376(5) . ?
C1 C2 1.383(5) . ?
C2 C3 1.384(6) . ?
C3 C4 1.340(6) . ?
C4 C5 1.355(7) . ?
C5 C6 1.401(6) . ?
C7 C12 1.544(5) . ?
C7 C8 1.550(5) . ?
C8 C9 1.533(6) . ?
C8 C13 1.535(6) . ?
C9 C10 1.516(7) . ?
C10 C11 1.511(7) . ?
C11 C12 1.519(6) . ?
C11 C16 1.527(7) . ?
C13 C14 1.523(6) . ?
C13 C15 1.529(6) . ?
C17 C18 1.466(6) . ?
C18 C19 1.190(5) . ?
C19 C20 1.434(6) . ?
C20 C21 1.377(6) . ?
C20 C25 1.382(6) . ?
C21 C22 1.371(6) . ?
C22 C23 1.381(6) . ?
C23 C24 1.373(6) . ?
C24 C25 1.366(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 112.00(17) . . ?
O1 P1 C7 112.91(18) . . ?
C1 P1 C7 110.91(17) . . ?
O1 P1 C17 110.79(17) . . ?
C1 P1 C17 102.52(17) . . ?
C7 P1 C17 107.11(18) . . ?
C23 O3 C26 117.8(4) . . ?
C6 C1 C2 119.3(4) . . ?
C6 C1 P1 118.7(3) . . ?
C2 C1 P1 122.0(3) . . ?
C1 C2 C3 120.0(4) . . ?
C4 C3 C2 120.3(5) . . ?
C3 C4 C5 121.1(5) . . ?
C4 C5 C6 119.9(5) . . ?
C1 C6 C5 119.4(4) . . ?
C12 C7 C8 110.4(3) . . ?
C12 C7 P1 108.7(3) . . ?
C8 C7 P1 112.5(3) . . ?
C9 C8 C13 112.2(4) . . ?
C9 C8 C7 108.8(3) . . ?
C13 C8 C7 115.8(3) . . ?
C10 C9 C8 112.1(4) . . ?
C11 C10 C9 111.6(4) . . ?
C10 C11 C12 110.0(4) . . ?
C10 C11 C16 112.9(4) . . ?
C12 C11 C16 110.9(4) . . ?
C11 C12 C7 113.1(3) . . ?
C14 C13 C15 110.0(4) . . ?
C14 C13 C8 114.8(4) . . ?
C15 C13 C8 111.4(4) . . ?
O2 C17 C18 113.9(3) . . ?
O2 C17 P1 108.8(2) . . ?
C18 C17 P1 107.4(3) . . ?
C19 C18 C17 173.7(5) . . ?
C18 C19 C20 176.7(5) . . ?
C21 C20 C25 117.3(4) . . ?
C21 C20 C19 121.5(4) . . ?
C25 C20 C19 121.2(4) . . ?
C22 C21 C20 121.7(4) . . ?
C21 C22 C23 119.9(4) . . ?
O3 C23 C24 125.3(4) . . ?
O3 C23 C22 115.4(4) . . ?
C24 C23 C22 119.3(4) . . ?
C25 C24 C23 119.9(4) . . ?
C24 C25 C20 121.9(4) . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.041

_shelxl_version_number           2014/6

