# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_exp_5923
_audit_block_doi                 10.5517/ccdc.csd.cc23btcn
_database_code_depnum_ccdc_archive 'CCDC 1946811'
loop_
_audit_author_name
_audit_author_address
'Jian Hao'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;
_audit_creation_date             2019-04-08
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            '1,2-oxaphosphinine 2-oxide'
_chemical_name_systematic        
;
 rel-(R,R,R)-2-ethoxy-3-(4-bromophenyl)-4,6-diphenyl-3,4-dihydro-1,2-oxaphosphinine 2-oxide
;
_chemical_formula_moiety         'C24 H22 Br O3 P'
_chemical_formula_sum            'C24 H22 Br O3 P'
_chemical_formula_weight         469.30
_chemical_melting_point          '218-220 deg'
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'
Br Br -0.2901 2.4595 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6694(3)
_cell_length_b                   10.1505(3)
_cell_length_c                   17.4217(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.448(3)
_cell_angle_gamma                90.00
_cell_volume                     2050.55(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2921
_cell_measurement_temperature    110.15(10)
_cell_measurement_theta_max      28.7660
_cell_measurement_theta_min      3.6790
_exptl_absorpt_coefficient_mu    2.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10391
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.99
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.15(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.8572
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   21.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647   57.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega    3.00   86.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   57.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -57.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
  4 omega   25.00   57.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -99.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00    6.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  -99.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -81.00  -17.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  -77.0000  -90.0000 64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0001575000
_diffrn_orient_matrix_UB_12      -0.0666810000
_diffrn_orient_matrix_UB_13      -0.0121969000
_diffrn_orient_matrix_UB_21      0.0370115000
_diffrn_orient_matrix_UB_22      0.0168434000
_diffrn_orient_matrix_UB_23      -0.0281005000
_diffrn_orient_matrix_UB_31      0.0487042000
_diffrn_orient_matrix_UB_32      -0.0125523000
_diffrn_orient_matrix_UB_33      0.0271769000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3422
_reflns_number_total             4023
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0266P)²+0.5631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0723
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Br1 Br 0.05377(2) 0.65616(2) 0.090469(14) 0.01820(9) Uani 1 1 d . . .
P1 P 0.27014(5) 1.29373(7) 0.01419(3) 0.01238(15) Uani 1 1 d . . .
C5 C 0.0359(2) 1.0638(3) 0.09517(12) 0.0132(5) Uani 1 1 d . . .
H5 H -0.0208 1.1270 0.0994 0.016 Uiso 1 1 calc R . .
O1 O 0.39579(13) 1.25060(17) 0.05396(9) 0.0146(4) Uani 1 1 d . . .
O2 O 0.25135(14) 1.23612(17) -0.06321(9) 0.0152(4) Uani 1 1 d . . .
C3 C 0.0923(2) 0.8388(2) 0.09135(13) 0.0135(5) Uani 1 1 d . . .
O3 O 0.26820(14) 1.44839(17) 0.01924(9) 0.0167(4) Uani 1 1 d . . .
C14 C 0.1595(2) 1.1608(2) 0.26794(13) 0.0144(5) Uani 1 1 d . . .
H14 H 0.2138 1.0988 0.2567 0.017 Uiso 1 1 calc R . .
C11 C -0.0034(2) 1.3440(3) 0.30178(14) 0.0194(6) Uani 1 1 d . . .
H11 H -0.0582 1.4056 0.3129 0.023 Uiso 1 1 calc R . .
C18 C 0.6037(2) 1.1336(2) 0.10126(14) 0.0151(5) Uani 1 1 d . . .
H18 H 0.5680 1.1190 0.0515 0.018 Uiso 1 1 calc R . .
C19 C 0.7134(2) 1.0842(3) 0.12262(14) 0.0178(6) Uani 1 1 d . . .
H19 H 0.7502 1.0354 0.0874 0.021 Uiso 1 1 calc R . .
C16 C 0.4258(2) 1.2479(2) 0.13430(13) 0.0126(5) Uani 1 1 d . . .
C7 C 0.1742(2) 1.2508(2) 0.08419(13) 0.0122(5) Uani 1 1 d . . .
H7 H 0.1009 1.2957 0.0689 0.015 Uiso 1 1 calc R . .
C6 C 0.1485(2) 1.1043(2) 0.08661(12) 0.0116(5) Uani 1 1 d . . .
C15 C 0.3496(2) 1.2718(2) 0.18398(13) 0.0128(5) Uani 1 1 d . . .
H15 H 0.3757 1.2631 0.2362 0.015 Uiso 1 1 calc R . .
C9 C 0.15016(19) 1.2797(2) 0.22737(13) 0.0113(5) Uani 1 1 d . . .
C10 C 0.0680(2) 1.3703(3) 0.24495(14) 0.0159(6) Uani 1 1 d . . .
H10 H 0.0606 1.4498 0.2183 0.019 Uiso 1 1 calc R . .
C4 C 0.0071(2) 0.9316(2) 0.09742(13) 0.0139(5) Uani 1 1 d . . .
H4 H -0.0680 0.9058 0.1029 0.017 Uiso 1 1 calc R . .
C1 C 0.2318(2) 1.0073(2) 0.08206(13) 0.0144(5) Uani 1 1 d . . .
H1 H 0.3075 1.0321 0.0776 0.017 Uiso 1 1 calc R . .
C22 C 0.6041(2) 1.2298(3) 0.22723(14) 0.0165(6) Uani 1 1 d . . .
H22 H 0.5681 1.2793 0.2625 0.020 Uiso 1 1 calc R . .
C13 C 0.0887(2) 1.1342(3) 0.32476(13) 0.0171(6) Uani 1 1 d . . .
H13 H 0.0957 1.0548 0.3515 0.021 Uiso 1 1 calc R . .
C8 C 0.2258(2) 1.3112(2) 0.16435(13) 0.0121(5) Uani 1 1 d . . .
H8 H 0.2248 1.4072 0.1581 0.015 Uiso 1 1 calc R . .
C23 C 0.3059(2) 1.5315(3) -0.04157(14) 0.0207(6) Uani 1 1 d . . .
H23A H 0.3612 1.4837 -0.0686 0.025 Uiso 1 1 calc R . .
H23B H 0.3437 1.6095 -0.0188 0.025 Uiso 1 1 calc R . .
C20 C 0.7686(2) 1.1071(3) 0.19618(14) 0.0185(6) Uani 1 1 d . . .
H20 H 0.8417 1.0726 0.2107 0.022 Uiso 1 1 calc R . .
C21 C 0.7140(2) 1.1816(3) 0.24787(14) 0.0187(6) Uani 1 1 d . . .
H21 H 0.7515 1.1992 0.2967 0.022 Uiso 1 1 calc R . .
C2 C 0.2045(2) 0.8748(2) 0.08407(13) 0.0144(5) Uani 1 1 d . . .
H2 H 0.2609 0.8110 0.0806 0.017 Uiso 1 1 calc R . .
C24 C 0.2050(2) 1.5713(3) -0.09780(14) 0.0245(6) Uani 1 1 d . . .
H24A H 0.1699 1.4942 -0.1222 0.037 Uiso 1 1 calc R . .
H24B H 0.2309 1.6282 -0.1364 0.037 Uiso 1 1 calc R . .
H24C H 0.1496 1.6171 -0.0709 0.037 Uiso 1 1 calc R . .
C17 C 0.5464(2) 1.2050(2) 0.15362(13) 0.0125(5) Uani 1 1 d . . .
C12 C 0.0072(2) 1.2261(3) 0.34182(14) 0.0186(6) Uani 1 1 d . . .
H12 H -0.0402 1.2085 0.3801 0.022 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.907(2) . ?
P1 O1 1.6105(16) . ?
P1 O2 1.4634(17) . ?
P1 O3 1.5727(18) . ?
P1 C7 1.799(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.400(3) . ?
C5 C4 1.385(3) . ?
O1 C16 1.404(3) . ?
C3 C4 1.383(3) . ?
C3 C2 1.378(3) . ?
O3 C23 1.460(3) . ?
C14 H14 0.9300 . ?
C14 C9 1.396(3) . ?
C14 C13 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.389(3) . ?
C11 C12 1.384(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(3) . ?
C18 C17 1.393(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(3) . ?
C16 C15 1.331(3) . ?
C16 C17 1.476(3) . ?
C7 H7 0.9800 . ?
C7 C6 1.519(3) . ?
C7 C8 1.581(3) . ?
C6 C1 1.393(3) . ?
C15 H15 0.9300 . ?
C15 C8 1.501(3) . ?
C9 C10 1.388(3) . ?
C9 C8 1.518(3) . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.384(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.382(3) . ?
C22 C17 1.403(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.387(4) . ?
C8 H8 0.9800 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.500(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(4) . ?
C21 H21 0.9300 . ?
C2 H2 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C12 H12 0.9300 . ?

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 C7 104.36(10) . . ?
O2 P1 O1 108.83(9) . . ?
O2 P1 O3 116.67(10) . . ?
O2 P1 C7 119.17(11) . . ?
O3 P1 O1 105.39(9) . . ?
O3 P1 C7 100.95(10) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(2) . . ?
C16 O1 P1 123.16(14) . . ?
C4 C3 Br1 119.47(18) . . ?
C2 C3 Br1 118.84(19) . . ?
C2 C3 C4 121.7(2) . . ?
C23 O3 P1 121.90(15) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C9 120.8(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 119.9(2) . . ?
C19 C18 H18 119.7 . . ?
C19 C18 C17 120.6(2) . . ?
C17 C18 H18 119.7 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
O1 C16 C17 110.95(19) . . ?
C15 C16 O1 122.3(2) . . ?
C15 C16 C17 126.5(2) . . ?
P1 C7 H7 107.1 . . ?
C6 C7 P1 113.35(16) . . ?
C6 C7 H7 107.1 . . ?
C6 C7 C8 114.35(19) . . ?
C8 C7 P1 107.51(16) . . ?
C8 C7 H7 107.1 . . ?
C5 C6 C7 118.8(2) . . ?
C1 C6 C5 117.9(2) . . ?
C1 C6 C7 123.3(2) . . ?
C16 C15 H15 116.7 . . ?
C16 C15 C8 126.6(2) . . ?
C8 C15 H15 116.7 . . ?
C14 C9 C8 122.0(2) . . ?
C10 C9 C14 118.5(2) . . ?
C10 C9 C8 119.5(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H10 119.5 . . ?
C5 C4 H4 120.7 . . ?
C3 C4 C5 118.6(2) . . ?
C3 C4 H4 120.7 . . ?
C6 C1 H1 119.3 . . ?
C2 C1 C6 121.4(2) . . ?
C2 C1 H1 119.3 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C17 120.7(2) . . ?
C17 C22 H22 119.6 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C7 C8 H8 106.8 . . ?
C15 C8 C7 111.00(19) . . ?
C15 C8 C9 113.68(19) . . ?
C15 C8 H8 106.8 . . ?
C9 C8 C7 111.27(19) . . ?
C9 C8 H8 106.8 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 C24 110.5(2) . . ?
H23A C23 H23B 108.1 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.5(2) . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C18 C17 C16 121.3(2) . . ?
C18 C17 C22 118.4(2) . . ?
C22 C17 C16 120.2(2) . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C3 C4 C5 -177.71(16) . . . . ?
Br1 C3 C2 C1 177.83(17) . . . . ?
P1 O1 C16 C15 5.0(3) . . . . ?
P1 O1 C16 C17 -179.76(16) . . . . ?
P1 O3 C23 C24 94.5(2) . . . . ?
P1 C7 C6 C5 -139.84(18) . . . . ?
P1 C7 C6 C1 41.3(3) . . . . ?
P1 C7 C8 C15 -52.3(2) . . . . ?
P1 C7 C8 C9 -179.94(16) . . . . ?
C5 C6 C1 C2 1.5(3) . . . . ?
O1 P1 O3 C23 89.64(17) . . . . ?
O1 P1 C7 C6 -76.81(17) . . . . ?
O1 P1 C7 C8 50.57(17) . . . . ?
O1 C16 C15 C8 -3.5(4) . . . . ?
O1 C16 C17 C18 -21.2(3) . . . . ?
O1 C16 C17 C22 162.1(2) . . . . ?
O2 P1 O1 C16 -156.87(17) . . . . ?
O2 P1 O3 C23 -31.2(2) . . . . ?
O2 P1 C7 C6 44.8(2) . . . . ?
O2 P1 C7 C8 172.22(15) . . . . ?
O3 P1 O1 C16 77.27(18) . . . . ?
O3 P1 C7 C6 174.00(15) . . . . ?
O3 P1 C7 C8 -58.61(17) . . . . ?
C14 C9 C10 C11 0.2(4) . . . . ?
C14 C9 C8 C7 84.2(3) . . . . ?
C14 C9 C8 C15 -42.0(3) . . . . ?
C14 C13 C12 C11 0.2(4) . . . . ?
C18 C19 C20 C21 -1.0(4) . . . . ?
C19 C18 C17 C16 -174.3(2) . . . . ?
C19 C18 C17 C22 2.4(4) . . . . ?
C19 C20 C21 C22 1.8(4) . . . . ?
C16 C15 C8 C7 30.8(3) . . . . ?
C16 C15 C8 C9 157.2(2) . . . . ?
C7 P1 O1 C16 -28.6(2) . . . . ?
C7 P1 O3 C23 -161.98(17) . . . . ?
C7 C6 C1 C2 -179.7(2) . . . . ?
C6 C5 C4 C3 0.3(3) . . . . ?
C6 C7 C8 C15 74.5(2) . . . . ?
C6 C7 C8 C9 -53.1(3) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C15 C16 C17 C18 153.8(3) . . . . ?
C15 C16 C17 C22 -22.9(4) . . . . ?
C9 C14 C13 C12 0.1(4) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C10 C9 C8 C7 -95.0(3) . . . . ?
C10 C9 C8 C15 138.8(2) . . . . ?
C4 C5 C6 C7 179.7(2) . . . . ?
C4 C5 C6 C1 -1.4(3) . . . . ?
C4 C3 C2 C1 -0.6(4) . . . . ?
C13 C14 C9 C10 -0.3(3) . . . . ?
C13 C14 C9 C8 -179.5(2) . . . . ?
C8 C7 C6 C5 96.4(2) . . . . ?
C8 C7 C6 C1 -82.4(3) . . . . ?
C8 C9 C10 C11 179.4(2) . . . . ?
C21 C22 C17 C18 -1.7(4) . . . . ?
C21 C22 C17 C16 175.1(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C17 C16 C15 C8 -177.9(2) . . . . ?
C17 C22 C21 C20 -0.4(4) . . . . ?
C12 C11 C10 C9 0.1(4) . . . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_exp_5719
_audit_block_doi                 10.5517/ccdc.csd.cc23bvv5
_database_code_depnum_ccdc_archive 'CCDC 1946857'
loop_
_audit_author_name
_audit_author_address
'Jian Hao'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;
_audit_creation_date             2018-12-12
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            '1,2-oxaphosphinine 2-oxide'
_chemical_name_systematic        
;
 rel-(2R,3S,4R)-2-ethoxy-4,6-diphenyl-3-(4-(trifluoromethyl)phenyl)-3,4-dihydro-1,2-oxaphosphinine 2-oxide 
;
_chemical_formula_moiety         'C25 H22 F3 O3 P'
_chemical_formula_sum            'C25 H22 F3 O3 P'
_chemical_formula_weight         458.40
_chemical_melting_point          '199-201 deg'
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'
F F 0.0171 0.0103 '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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y, x-y, z'
3 '-x+y, -x, z'
4 'x+2/3, y+1/3, z+1/3'
5 '-y+2/3, x-y+1/3, z+1/3'
6 '-x+y+2/3, -x+1/3, z+1/3'
7 'x+1/3, y+2/3, z+2/3'
8 '-y+1/3, x-y+2/3, z+2/3'
9 '-x+y+1/3, -x+2/3, z+2/3'
10 '-x, -y, -z'
11 'y, -x+y, -z'
12 'x-y, x, -z'
13 '-x+2/3, -y+1/3, -z+1/3'
14 'y+2/3, -x+y+1/3, -z+1/3'
15 'x-y+2/3, x+1/3, -z+1/3'
16 '-x+1/3, -y+2/3, -z+2/3'
17 'y+1/3, -x+y+2/3, -z+2/3'
18 'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   17.8304(14)
_cell_length_b                   17.8304(14)
_cell_length_c                   36.593(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     10075(5)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    2493
_cell_measurement_temperature    108.05(10)
_cell_measurement_theta_max      28.7850
_cell_measurement_theta_min      4.0410
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             4284
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            8699
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.45
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      108.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.8404
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -34.00   29.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -37.0000 -180.0000 63

#__ type_ start__ end____ width___ exp.time_
  2 omega   -2.00   63.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772    0.0000 -180.0000 65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0075939000
_diffrn_orient_matrix_UB_12      -0.0382042000
_diffrn_orient_matrix_UB_13      -0.0091848000
_diffrn_orient_matrix_UB_21      -0.0267390000
_diffrn_orient_matrix_UB_22      -0.0253974000
_diffrn_orient_matrix_UB_23      0.0146251000
_diffrn_orient_matrix_UB_31      -0.0365288000
_diffrn_orient_matrix_UB_32      -0.0023660000
_diffrn_orient_matrix_UB_33      -0.0088177000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3362
_reflns_number_total             4388
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4388
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0350P)²+14.0742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1102
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.91339(4) 0.52972(4) 0.026542(16) 0.02713(16) Uani 1 1 d . A .
F2 F 0.90591(10) 0.26352(9) 0.17977(4) 0.0453(4) Uani 1 1 d . . .
F3 F 0.85823(11) 0.33648(9) 0.20785(4) 0.0499(4) Uani 1 1 d . . .
O1 O 0.95386(10) 0.60285(9) -0.00453(4) 0.0292(4) Uani 1 1 d . . .
O2 O 0.87844(10) 0.44470(9) 0.00944(4) 0.0323(4) Uani 1 1 d . . .
O3 O 0.84809(10) 0.54699(10) 0.04824(4) 0.0315(4) Uani 1 1 d DU . .
F1 F 0.78264(9) 0.24827(9) 0.16535(4) 0.0495(4) Uani 1 1 d . . .
C13 C 0.94471(14) 0.71284(14) -0.05370(6) 0.0259(5) Uani 1 1 d . A .
H13 H 0.9063 0.6535 -0.0548 0.031 Uiso 1 1 calc R . .
C1 C 1.00057(13) 0.69058(13) 0.00565(6) 0.0246(5) Uani 1 1 d . A .
C7 C 0.88151(14) 0.44032(14) 0.14510(6) 0.0256(5) Uani 1 1 d . A .
H7 H 0.8434 0.4409 0.1623 0.031 Uiso 1 1 calc R . .
C5 C 0.97069(13) 0.50223(13) 0.09162(6) 0.0222(5) Uani 1 1 d . A .
C18 C 1.12910(14) 0.69845(13) 0.08417(6) 0.0252(5) Uani 1 1 d . . .
C4 C 0.99962(14) 0.56285(13) 0.05902(6) 0.0247(5) Uani 1 1 d . . .
H4 H 1.0460 0.5580 0.0469 0.030 Uiso 1 1 calc R A .
C8 C 0.90598(14) 0.37806(14) 0.14711(6) 0.0253(5) Uani 1 1 d . . .
C3 C 1.03734(14) 0.66009(13) 0.06941(6) 0.0251(5) Uani 1 1 d . A .
H3 H 1.0013 0.6626 0.0891 0.030 Uiso 1 1 calc R . .
C19 C 1.19566(14) 0.70951(14) 0.06101(6) 0.0304(5) Uani 1 1 d . . .
H19 H 1.1829 0.6905 0.0369 0.036 Uiso 1 1 calc R . .
C10 C 0.99734(16) 0.44218(17) 0.09493(7) 0.0374(6) Uani 1 1 d . . .
H10 H 1.0373 0.4430 0.0784 0.045 Uiso 1 1 calc R A .
C6 C 0.91343(14) 0.50175(14) 0.11759(6) 0.0257(5) Uani 1 1 d . . .
H6 H 0.8964 0.5432 0.1164 0.031 Uiso 1 1 calc R A .
C2 C 1.03652(13) 0.71547(14) 0.03834(6) 0.0261(5) Uani 1 1 d . . .
H2 H 1.0650 0.7748 0.0427 0.031 Uiso 1 1 calc R A .
C14 C 0.94479(15) 0.76574(15) -0.08144(6) 0.0313(5) Uani 1 1 d . . .
H14 H 0.9072 0.7417 -0.1011 0.038 Uiso 1 1 calc R . .
C12 C 1.00139(13) 0.74714(14) -0.02418(6) 0.0272(5) Uani 1 1 d . . .
C11 C 0.86442(15) 0.30744(14) 0.17482(7) 0.0323(5) Uani 1 1 d . . .
C20 C 1.28022(15) 0.74806(14) 0.07296(7) 0.0350(6) Uani 1 1 d . . .
H20 H 1.3241 0.7562 0.0569 0.042 Uiso 1 1 calc R . .
C9 C 0.96565(17) 0.38048(17) 0.12247(7) 0.0424(7) Uani 1 1 d . A .
H9 H 0.9847 0.3407 0.1243 0.051 Uiso 1 1 calc R . .
C23 C 1.14914(16) 0.72506(14) 0.12025(6) 0.0324(5) Uani 1 1 d . . .
H23 H 1.1054 0.7172 0.1363 0.039 Uiso 1 1 calc R . .
C21 C 1.29955(16) 0.77457(15) 0.10898(8) 0.0399(6) Uani 1 1 d . . .
H21 H 1.3564 0.7998 0.1173 0.048 Uiso 1 1 calc R . .
C15 C 1.00059(16) 0.85408(17) -0.07988(7) 0.0439(7) Uani 1 1 d . A .
H15 H 1.0009 0.8897 -0.0985 0.053 Uiso 1 1 calc R . .
C17 C 1.05727(16) 0.83669(16) -0.02300(7) 0.0457(7) Uani 1 1 d . A .
H17 H 1.0956 0.8610 -0.0036 0.055 Uiso 1 1 calc R . .
C22 C 1.23454(17) 0.76356(15) 0.13257(7) 0.0398(6) Uani 1 1 d . . .
H22 H 1.2476 0.7818 0.1567 0.048 Uiso 1 1 calc R . .
C16 C 1.05617(18) 0.88937(18) -0.05037(8) 0.0543(8) Uani 1 1 d . . .
H16 H 1.0930 0.9490 -0.0490 0.065 Uiso 1 1 calc R A .
C25 C 0.7270(2) 0.5546(3) 0.06101(11) 0.0427(9) Uani 0.651(3) 1 d P A 1
H25A H 0.7109 0.5117 0.0798 0.064 Uiso 0.651(3) 1 calc PR A 1
H25B H 0.6758 0.5516 0.0510 0.064 Uiso 0.651(3) 1 calc PR A 1
H25C H 0.7635 0.6111 0.0712 0.064 Uiso 0.651(3) 1 calc PR A 1
C24 C 0.7743(3) 0.5382(3) 0.03190(12) 0.0327(10) Uani 0.651(3) 1 d PDU A 1
H24A H 0.7393 0.4804 0.0220 0.039 Uiso 0.651(3) 1 calc PR A 1
H24B H 0.7893 0.5798 0.0122 0.039 Uiso 0.651(3) 1 calc PR A 1
C26 C 0.7469(5) 0.4973(5) 0.0415(2) 0.0327(10) Uani 0.349(3) 1 d PDU A 2
H26A H 0.7259 0.5380 0.0422 0.039 Uiso 0.349(3) 1 calc PR A 2
H26B H 0.7343 0.4705 0.0175 0.039 Uiso 0.349(3) 1 calc PR A 2
C27 C 0.7014(4) 0.4285(5) 0.07043(19) 0.0427(9) Uani 0.349(3) 1 d P A 2
H27A H 0.6405 0.3964 0.0652 0.064 Uiso 0.349(3) 1 calc PR A 2
H27B H 0.7105 0.4555 0.0940 0.064 Uiso 0.349(3) 1 calc PR A 2
H27C H 0.7243 0.3899 0.0705 0.064 Uiso 0.349(3) 1 calc PR A 2


_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 1.6042(16) . ?
P1 O2 1.4606(16) . ?
P1 O3 1.5618(16) . ?
P1 C4 1.794(2) . ?
F2 C11 1.332(3) . ?
F3 C11 1.341(3) . ?
O1 C1 1.406(2) . ?
O3 C24 1.381(4) . ?
O3 C26 1.582(7) . ?
F1 C11 1.349(3) . ?
C13 C14 1.385(3) . ?
C13 C12 1.394(3) . ?
C1 C2 1.324(3) . ?
C1 C12 1.481(3) . ?
C7 C8 1.383(3) . ?
C7 C6 1.383(3) . ?
C5 C4 1.517(3) . ?
C5 C10 1.377(3) . ?
C5 C6 1.392(3) . ?
C18 C3 1.522(3) . ?
C18 C19 1.390(3) . ?
C18 C23 1.388(3) . ?
C4 C3 1.561(3) . ?
C8 C11 1.493(3) . ?
C8 C9 1.379(3) . ?
C3 C2 1.511(3) . ?
C19 C20 1.379(3) . ?
C10 C9 1.387(3) . ?
C14 C15 1.381(3) . ?
C12 C17 1.398(3) . ?
C20 C21 1.385(4) . ?
C23 C22 1.396(3) . ?
C21 C22 1.378(4) . ?
C15 C16 1.386(4) . ?
C17 C16 1.380(3) . ?
C25 C24 1.476(6) . ?
C26 C27 1.514(10) . ?

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 C4 103.82(9) . . ?
O2 P1 O1 108.97(9) . . ?
O2 P1 O3 116.69(9) . . ?
O2 P1 C4 118.44(10) . . ?
O3 P1 O1 106.07(9) . . ?
O3 P1 C4 101.48(10) . . ?
C1 O1 P1 119.47(13) . . ?
P1 O3 C26 124.3(3) . . ?
C24 O3 P1 121.3(2) . . ?
C24 O3 C26 27.6(3) . . ?
C14 C13 C12 121.0(2) . . ?
O1 C1 C12 111.15(18) . . ?
C2 C1 O1 122.04(19) . . ?
C2 C1 C12 126.8(2) . . ?
C8 C7 C6 120.3(2) . . ?
C10 C5 C4 119.8(2) . . ?
C10 C5 C6 118.2(2) . . ?
C6 C5 C4 121.91(19) . . ?
C19 C18 C3 119.81(19) . . ?
C23 C18 C3 121.8(2) . . ?
C23 C18 C19 118.4(2) . . ?
C5 C4 P1 110.88(14) . . ?
C5 C4 C3 113.84(17) . . ?
C3 C4 P1 110.45(15) . . ?
C7 C8 C11 119.4(2) . . ?
C9 C8 C7 119.2(2) . . ?
C9 C8 C11 121.4(2) . . ?
C18 C3 C4 110.78(18) . . ?
C2 C3 C18 109.44(17) . . ?
C2 C3 C4 113.77(17) . . ?
C20 C19 C18 121.4(2) . . ?
C5 C10 C9 121.2(2) . . ?
C7 C6 C5 120.8(2) . . ?
C1 C2 C3 128.45(19) . . ?
C15 C14 C13 120.1(2) . . ?
C13 C12 C1 120.94(19) . . ?
C13 C12 C17 118.1(2) . . ?
C17 C12 C1 120.9(2) . . ?
F2 C11 F3 106.36(19) . . ?
F2 C11 F1 106.02(18) . . ?
F2 C11 C8 113.6(2) . . ?
F3 C11 F1 105.54(19) . . ?
F3 C11 C8 112.86(18) . . ?
F1 C11 C8 111.82(19) . . ?
C19 C20 C21 119.7(2) . . ?
C8 C9 C10 120.1(2) . . ?
C18 C23 C22 120.4(2) . . ?
C22 C21 C20 120.0(2) . . ?
C14 C15 C16 119.6(2) . . ?
C16 C17 C12 120.7(2) . . ?
C21 C22 C23 120.1(2) . . ?
C17 C16 C15 120.4(2) . . ?
O3 C24 C25 105.8(3) . . ?
C27 C26 O3 110.1(6) . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
