# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_rousee1B_0m
_database_code_depnum_ccdc_archive 'CCDC 1496850'
_audit_update_record             
;
2016-07-29 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(E)-((1-fluoro-2-(naphthalen-2-yl)vinyl)diphenylphosphine borane'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 B F P'
_chemical_formula_sum            'C24 H21 B F P'
_chemical_formula_weight         370.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.7951(2)
_cell_length_b                   15.6260(3)
_cell_length_c                   13.7061(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.4951(13)
_cell_angle_gamma                90
_cell_volume                     1965.04(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9881
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      31.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   0.6605
_exptl_transmission_factor_max   0.7462
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Sadabs 2015/1'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34477
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.574
_diffrn_reflns_theta_max         31.587
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6564
_reflns_number_gt                5147
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+1.6357P] 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         6564
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_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 0.32387(4) 0.16964(2) 0.05829(2) 0.01721(8) Uani 1 1 d . . . . .
C4 C 0.44003(14) 0.12068(8) 0.45423(10) 0.0197(2) Uani 1 1 d . . . . .
H4 H 0.5246 0.0957 0.4473 0.024 Uiso 1 1 calc R U . . .
C5 C 0.42508(14) 0.12181(8) 0.55319(10) 0.0193(2) Uani 1 1 d . . . . .
C3 C 0.33451(14) 0.15498(8) 0.36737(10) 0.0194(2) Uani 1 1 d . . . . .
C6 C 0.53137(15) 0.08445(9) 0.64314(10) 0.0222(3) Uani 1 1 d . . . . .
H6 H 0.6163 0.0589 0.6375 0.027 Uiso 1 1 calc R U . . .
C1 C 0.27718(14) 0.17803(8) 0.17427(10) 0.0198(2) Uani 1 1 d . . . . .
C19 C 0.31212(13) 0.27861(8) 0.01137(9) 0.0177(2) Uani 1 1 d . . . . .
C2 C 0.36101(14) 0.15160(8) 0.26856(10) 0.0197(2) Uani 1 1 d . . . . .
H2 H 0.4514 0.1269 0.2724 0.024 Uiso 1 1 calc R U . . .
C24 C 0.36009(15) 0.34544(9) 0.08264(11) 0.0236(3) Uani 1 1 d . . . . .
H24 H 0.3891 0.3342 0.1552 0.028 Uiso 1 1 calc R U . . .
C12 C 0.20867(16) 0.19281(10) 0.37845(11) 0.0259(3) Uani 1 1 d . . . . .
H12 H 0.1348 0.2161 0.3193 0.031 Uiso 1 1 calc R U . . .
C13 C 0.17472(14) 0.11107(8) -0.03308(10) 0.0203(2) Uani 1 1 d . . . . .
C20 C 0.27052(15) 0.29565(9) -0.09507(10) 0.0216(2) Uani 1 1 d . . . . .
H20 H 0.2374 0.2505 -0.1441 0.026 Uiso 1 1 calc R U . . .
C9 C 0.28502(17) 0.16195(10) 0.66337(11) 0.0287(3) Uani 1 1 d . . . . .
H9 H 0.2034 0.1894 0.6720 0.034 Uiso 1 1 calc R U . . .
C10 C 0.30012(15) 0.16078(9) 0.56371(10) 0.0225(3) Uani 1 1 d . . . . .
C7 C 0.51191(16) 0.08524(10) 0.73653(11) 0.0270(3) Uani 1 1 d . . . . .
H7 H 0.5828 0.0596 0.7954 0.032 Uiso 1 1 calc R U . . .
C23 C 0.36555(17) 0.42839(9) 0.04781(12) 0.0285(3) Uani 1 1 d . . . . .
H23 H 0.3973 0.4739 0.0965 0.034 Uiso 1 1 calc R U . . .
C14 C 0.20101(18) 0.02929(10) -0.06250(12) 0.0291(3) Uani 1 1 d . . . . .
H14 H 0.2966 0.0060 -0.0370 0.035 Uiso 1 1 calc R U . . .
C22 C 0.32476(16) 0.44480(9) -0.05794(13) 0.0285(3) Uani 1 1 d . . . . .
H22 H 0.3291 0.5015 -0.0816 0.034 Uiso 1 1 calc R U . . .
C18 C 0.03427(16) 0.14510(10) -0.07114(12) 0.0281(3) Uani 1 1 d . . . . .
H18 H 0.0161 0.2009 -0.0511 0.034 Uiso 1 1 calc R U . . .
C11 C 0.19332(17) 0.19584(11) 0.47407(11) 0.0290(3) Uani 1 1 d . . . . .
H11 H 0.1092 0.2220 0.4803 0.035 Uiso 1 1 calc R U . . .
C21 C 0.27764(16) 0.37874(10) -0.12929(11) 0.0261(3) Uani 1 1 d . . . . .
H21 H 0.2501 0.3902 -0.2017 0.031 Uiso 1 1 calc R U . . .
C8 C 0.38810(18) 0.12359(11) 0.74686(11) 0.0304(3) Uani 1 1 d . . . . .
H8 H 0.3756 0.1229 0.8125 0.037 Uiso 1 1 calc R U . . .
C15 C 0.0860(2) -0.01816(11) -0.12958(14) 0.0405(4) Uani 1 1 d . . . . .
H15 H 0.1032 -0.0741 -0.1497 0.049 Uiso 1 1 calc R U . . .
C16 C -0.0526(2) 0.01563(12) -0.16688(13) 0.0410(4) Uani 1 1 d . . . . .
H16 H -0.1306 -0.0172 -0.2125 0.049 Uiso 1 1 calc R U . . .
C17 C -0.07867(18) 0.09714(12) -0.13822(13) 0.0367(4) Uani 1 1 d . . . . .
H17 H -0.1743 0.1203 -0.1646 0.044 Uiso 1 1 calc R U . . .
B1 B 0.51290(17) 0.12185(10) 0.08424(12) 0.0235(3) Uani 1 1 d . . . . .
H1A H 0.5317 0.1181 0.0187 0.035 Uiso 1 1 calc R U . . .
H1B H 0.5173 0.0645 0.1141 0.035 Uiso 1 1 calc R U . . .
H1C H 0.5867 0.1584 0.1333 0.035 Uiso 1 1 calc R U . . .
F1 F 0.14414(10) 0.21386(7) 0.15668(7) 0.0345(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
P1 C1 1.8063(13) . ?
P1 C13 1.8054(13) . ?
P1 C19 1.8094(13) . ?
P1 B1 1.9108(16) . ?
C4 C3 1.3825(18) . ?
C4 C5 1.4144(17) . ?
C4 H4 0.9500 . ?
C5 C10 1.4189(18) . ?
C5 C6 1.4304(18) . ?
C3 C12 1.4224(18) . ?
C3 C2 1.4663(17) . ?
C6 C7 1.3585(19) . ?
C6 H6 0.9500 . ?
C1 C2 1.3311(17) . ?
C1 F1 1.3601(15) . ?
C19 C24 1.3944(18) . ?
C19 C20 1.3960(17) . ?
C2 H2 0.9500 . ?
C24 C23 1.389(2) . ?
C24 H24 0.9500 . ?
C12 C11 1.3712(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(2) . ?
C13 C18 1.395(2) . ?
C20 C21 1.3905(19) . ?
C20 H20 0.9500 . ?
C9 C8 1.371(2) . ?
C9 C10 1.4246(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.4156(19) . ?
C7 C8 1.404(2) . ?
C7 H7 0.9500 . ?
C23 C22 1.386(2) . ?
C23 H23 0.9500 . ?
C14 C15 1.392(2) . ?
C14 H14 0.9500 . ?
C22 C21 1.385(2) . ?
C22 H22 0.9500 . ?
C18 C17 1.385(2) . ?
C18 H18 0.9500 . ?
C11 H11 0.9500 . ?
C21 H21 0.9500 . ?
C8 H8 0.9500 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
B1 H1A 0.9800 . ?
B1 H1B 0.9800 . ?
B1 H1C 0.9800 . ?

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
C1 P1 C13 104.74(6) . . ?
C1 P1 C19 103.91(6) . . ?
C13 P1 C19 107.17(6) . . ?
C1 P1 B1 113.07(6) . . ?
C13 P1 B1 115.28(7) . . ?
C19 P1 B1 111.77(6) . . ?
C3 C4 C5 121.58(12) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C10 119.05(12) . . ?
C4 C5 C6 122.21(12) . . ?
C10 C5 C6 118.75(12) . . ?
C4 C3 C12 118.93(12) . . ?
C4 C3 C2 117.43(12) . . ?
C12 C3 C2 123.63(12) . . ?
C7 C6 C5 120.57(13) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C2 C1 F1 121.79(12) . . ?
C2 C1 P1 124.88(10) . . ?
F1 C1 P1 113.33(9) . . ?
C24 C19 C20 119.52(12) . . ?
C24 C19 P1 119.46(10) . . ?
C20 C19 P1 120.66(10) . . ?
C1 C2 C3 129.57(12) . . ?
C1 C2 H2 115.2 . . ?
C3 C2 H2 115.2 . . ?
C23 C24 C19 120.15(13) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
C11 C12 C3 120.37(13) . . ?
C11 C12 H12 119.8 . . ?
C3 C12 H12 119.8 . . ?
C14 C13 C18 120.03(13) . . ?
C14 C13 P1 118.68(11) . . ?
C18 C13 P1 121.26(11) . . ?
C21 C20 C19 120.00(13) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C8 C9 C10 120.09(14) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 122.27(13) . . ?
C11 C10 C5 118.65(12) . . ?
C9 C10 C5 119.07(12) . . ?
C6 C7 C8 120.67(13) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C22 C23 C24 120.03(13) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C13 C14 C15 119.44(15) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C21 C22 C23 120.22(13) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C17 C18 C13 119.73(15) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C12 C11 C10 121.41(13) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C22 C21 C20 120.08(13) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C9 C8 C7 120.82(13) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C16 C15 C14 120.36(16) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.23(15) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.21(16) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
P1 B1 H1A 109.5 . . ?
P1 B1 H1B 109.5 . . ?
H1A B1 H1B 109.5 . . ?
P1 B1 H1C 109.5 . . ?
H1A B1 H1C 109.5 . . ?
H1B B1 H1C 109.5 . . ?

_refine_diff_density_max         0.647
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.059


####################################################################### 
# 
# 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_rousee2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1496851'
_audit_update_record             
;
2016-07-29 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(E)-((2-(4-chlorophenyl)-1 fluorovinyl)diphenyl phosphine borane'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 B Cl F P'
_chemical_formula_sum            'C20 H18 B Cl F P'
_chemical_formula_weight         354.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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                   8.8929(2)
_cell_length_b                   9.3285(2)
_cell_length_c                   12.0260(3)
_cell_angle_alpha                68.3220(10)
_cell_angle_beta                 83.0170(10)
_cell_angle_gamma                80.7320(10)
_cell_volume                     912.89(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9292
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      45.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.304
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33171
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.859
_diffrn_reflns_theta_max         36.318
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8837
_reflns_number_gt                7884
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0565P)²+0.1785P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8837
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.23347(2) 0.31741(2) 0.83278(2) 0.01499(4) Uani 1 1 d . . . . .
Cl1 Cl 0.89017(3) -0.07500(3) 0.39079(2) 0.03311(6) Uani 1 1 d . . . . .
F1 F 0.35755(6) 0.40482(6) 0.60759(4) 0.02713(11) Uani 1 1 d . . . . .
C3 C 0.56451(8) 0.10740(8) 0.64144(6) 0.01710(10) Uani 1 1 d . . . . .
C15 C 0.04993(7) 0.35727(8) 0.77082(6) 0.01614(10) Uani 1 1 d . . . . .
C9 C 0.27617(8) 0.49415(8) 0.84408(6) 0.01735(11) Uani 1 1 d . . . . .
C16 C -0.04974(8) 0.24473(9) 0.81916(7) 0.01972(12) Uani 1 1 d . . . . .
C2 C 0.46033(8) 0.15453(8) 0.72926(6) 0.01723(11) Uani 1 1 d . . . . .
C1 C 0.36598(8) 0.28554(8) 0.71547(6) 0.01676(10) Uani 1 1 d . . . . .
C8 C 0.66776(9) -0.02740(9) 0.68599(7) 0.02103(12) Uani 1 1 d . . . . .
C14 C 0.42915(9) 0.51396(9) 0.84110(8) 0.02252(13) Uani 1 1 d . . . . .
C20 C 0.01025(8) 0.49092(8) 0.67176(7) 0.02016(12) Uani 1 1 d . . . . .
C10 C 0.16124(9) 0.59958(10) 0.87127(8) 0.02352(13) Uani 1 1 d . . . . .
C4 C 0.56565(10) 0.18621(9) 0.51694(7) 0.02318(13) Uani 1 1 d . . . . .
C17 C -0.18753(9) 0.26495(10) 0.76840(8) 0.02532(14) Uani 1 1 d . . . . .
C6 C 0.76652(9) -0.00383(9) 0.48724(7) 0.02227(13) Uani 1 1 d . . . . .
C19 C -0.12746(9) 0.50962(9) 0.62117(7) 0.02291(13) Uani 1 1 d . . . . .
C7 C 0.76911(10) -0.08313(9) 0.60989(8) 0.02412(13) Uani 1 1 d . . . . .
C11 C 0.20020(12) 0.72289(10) 0.89617(8) 0.02898(16) Uani 1 1 d . . . . .
C5 C 0.66629(10) 0.13073(10) 0.43996(7) 0.02563(14) Uani 1 1 d . . . . .
C13 C 0.46650(11) 0.63720(10) 0.86664(9) 0.02820(16) Uani 1 1 d . . . . .
C12 C 0.35225(12) 0.74055(10) 0.89495(8) 0.02962(16) Uani 1 1 d . . . . .
C18 C -0.22556(9) 0.39647(11) 0.66901(8) 0.02510(14) Uani 1 1 d . . . . .
B1 B 0.25276(10) 0.14669(11) 0.98325(8) 0.02269(14) Uani 1 1 d . . . . .
H2 H 0.4611(14) 0.0789(15) 0.8113(12) 0.024(3) Uiso 1 1 d . . . . .
H4 H 0.4952(17) 0.2755(17) 0.4831(13) 0.036(4) Uiso 1 1 d . . . . .
H5 H 0.6634(16) 0.1846(17) 0.3549(13) 0.032(3) Uiso 1 1 d . . . . .
H8 H 0.6723(16) -0.0810(15) 0.7713(13) 0.029(3) Uiso 1 1 d . . . . .
H7 H 0.8365(17) -0.1781(18) 0.6414(14) 0.037(4) Uiso 1 1 d . . . . .
H14 H 0.5079(16) 0.4438(16) 0.8209(12) 0.029(3) Uiso 1 1 d . . . . .
H10 H 0.0566(18) 0.5866(19) 0.8713(15) 0.044(4) Uiso 1 1 d . . . . .
H11 H 0.1221(18) 0.7966(18) 0.9127(14) 0.041(4) Uiso 1 1 d . . . . .
H13 H 0.5731(19) 0.6480(19) 0.8633(15) 0.044(4) Uiso 1 1 d . . . . .
H12 H 0.3775(19) 0.8253(19) 0.9142(15) 0.044(4) Uiso 1 1 d . . . . .
H16 H -0.0267(15) 0.1562(15) 0.8865(12) 0.024(3) Uiso 1 1 d . . . . .
H17 H -0.2537(16) 0.1826(16) 0.8036(13) 0.032(3) Uiso 1 1 d . . . . .
H19 H -0.1525(16) 0.5980(16) 0.5537(13) 0.033(3) Uiso 1 1 d . . . . .
H20 H 0.0782(15) 0.5689(16) 0.6380(12) 0.028(3) Uiso 1 1 d . . . . .
H18 H -0.3179(17) 0.4061(17) 0.6348(14) 0.037(4) Uiso 1 1 d . . . . .
H1A H 0.2253(16) 0.0423(16) 0.9720(13) 0.035(4) Uiso 1 1 d . . . . .
H1B H 0.1713(18) 0.1868(18) 1.0470(14) 0.043(4) Uiso 1 1 d . . . . .
H1C H 0.3685(19) 0.1359(19) 1.0028(15) 0.047(4) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C15 1.8036(7) . ?
P1 C1 1.8056(7) . ?
P1 C9 1.8057(7) . ?
P1 B1 1.9232(9) . ?
Cl1 C6 1.7375(7) . ?
F1 C1 1.3628(8) . ?
C3 C8 1.4005(10) . ?
C3 C4 1.4027(10) . ?
C3 C2 1.4633(10) . ?
C15 C16 1.3962(10) . ?
C15 C20 1.4005(10) . ?
C9 C14 1.3965(10) . ?
C9 C10 1.3969(10) . ?
C16 C17 1.3900(11) . ?
C16 H16 0.934(13) . ?
C2 C1 1.3337(9) . ?
C2 H2 0.978(13) . ?
C8 C7 1.3858(11) . ?
C8 H8 0.963(14) . ?
C14 C13 1.3911(11) . ?
C14 H14 0.952(14) . ?
C20 C19 1.3907(10) . ?
C20 H20 0.961(13) . ?
C10 C11 1.3931(12) . ?
C10 H10 0.958(16) . ?
C4 C5 1.3890(11) . ?
C4 H4 0.947(15) . ?
C17 C18 1.3891(12) . ?
C17 H17 0.980(14) . ?
C6 C7 1.3857(12) . ?
C6 C5 1.3889(12) . ?
C19 C18 1.3900(12) . ?
C19 H19 0.937(14) . ?
C7 H7 0.961(15) . ?
C11 C12 1.3859(14) . ?
C11 H11 0.953(16) . ?
C5 H5 0.960(15) . ?
C13 C12 1.3859(14) . ?
C13 H13 0.964(16) . ?
C12 H12 0.967(17) . ?
C18 H18 0.939(15) . ?
B1 H1A 1.099(14) . ?
B1 H1B 1.115(16) . ?
B1 H1C 1.065(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 P1 C1 103.73(3) . . ?
C15 P1 C9 108.16(3) . . ?
C1 P1 C9 105.29(3) . . ?
C15 P1 B1 115.24(4) . . ?
C1 P1 B1 112.46(4) . . ?
C9 P1 B1 111.24(4) . . ?
C8 C3 C4 118.46(6) . . ?
C8 C3 C2 117.02(6) . . ?
C4 C3 C2 124.51(6) . . ?
C16 C15 C20 119.87(6) . . ?
C16 C15 P1 117.94(5) . . ?
C20 C15 P1 122.04(5) . . ?
C14 C9 C10 119.73(7) . . ?
C14 C9 P1 118.34(5) . . ?
C10 C9 P1 121.38(5) . . ?
C17 C16 C15 119.98(7) . . ?
C17 C16 H16 118.8(8) . . ?
C15 C16 H16 121.2(8) . . ?
C1 C2 C3 130.16(6) . . ?
C1 C2 H2 114.8(8) . . ?
C3 C2 H2 115.0(8) . . ?
C2 C1 F1 121.62(6) . . ?
C2 C1 P1 123.94(5) . . ?
F1 C1 P1 114.37(5) . . ?
C7 C8 C3 121.37(7) . . ?
C7 C8 H8 118.6(8) . . ?
C3 C8 H8 120.0(8) . . ?
C13 C14 C9 119.96(8) . . ?
C13 C14 H14 119.9(8) . . ?
C9 C14 H14 120.1(8) . . ?
C19 C20 C15 119.70(7) . . ?
C19 C20 H20 119.9(8) . . ?
C15 C20 H20 120.4(8) . . ?
C11 C10 C9 119.72(8) . . ?
C11 C10 H10 121.0(10) . . ?
C9 C10 H10 119.2(10) . . ?
C5 C4 C3 120.56(7) . . ?
C5 C4 H4 118.3(9) . . ?
C3 C4 H4 121.1(9) . . ?
C18 C17 C16 120.03(7) . . ?
C18 C17 H17 122.2(8) . . ?
C16 C17 H17 117.8(8) . . ?
C7 C6 C5 121.27(7) . . ?
C7 C6 Cl1 119.31(6) . . ?
C5 C6 Cl1 119.41(6) . . ?
C18 C19 C20 120.16(7) . . ?
C18 C19 H19 120.4(9) . . ?
C20 C19 H19 119.5(9) . . ?
C6 C7 C8 118.90(7) . . ?
C6 C7 H7 120.5(9) . . ?
C8 C7 H7 120.6(9) . . ?
C12 C11 C10 120.29(8) . . ?
C12 C11 H11 119.7(9) . . ?
C10 C11 H11 120.0(10) . . ?
C6 C5 C4 119.43(7) . . ?
C6 C5 H5 121.2(9) . . ?
C4 C5 H5 119.4(9) . . ?
C12 C13 C14 120.16(8) . . ?
C12 C13 H13 121.9(10) . . ?
C14 C13 H13 117.9(10) . . ?
C13 C12 C11 120.12(7) . . ?
C13 C12 H12 120.6(10) . . ?
C11 C12 H12 119.3(10) . . ?
C17 C18 C19 120.24(7) . . ?
C17 C18 H18 118.5(9) . . ?
C19 C18 H18 121.2(9) . . ?
P1 B1 H1A 108.5(8) . . ?
P1 B1 H1B 104.0(8) . . ?
H1A B1 H1B 114.0(11) . . ?
P1 B1 H1C 104.8(9) . . ?
H1A B1 H1C 112.4(12) . . ?
H1B B1 H1C 112.3(12) . . ?

_refine_diff_density_max         0.610
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_rousee3_0m
_database_code_depnum_ccdc_archive 'CCDC 1496852'
_audit_update_record             
;
2016-07-29 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(E)-((2-(3-chlorophenyl)-1 fluorovinyl)diphenyl phosphine borane'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 B Cl F P'
_chemical_formula_sum            'C20 H18 B Cl F P'
_chemical_formula_weight         354.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.8720(4)
_cell_length_b                   12.1211(4)
_cell_length_c                   13.7228(5)
_cell_angle_alpha                90
_cell_angle_beta                 112.1550(13)
_cell_angle_gamma                90
_cell_volume                     1828.93(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      33.63

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.29
_exptl_absorpt_coefficient_mu    0.303
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39693
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.501
_diffrn_reflns_theta_max         31.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6070
_reflns_number_gt                5333
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0483P)²+0.8431P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6070
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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 0.34576(2) 0.21246(2) 0.07137(2) 0.01692(7) Uani 1 1 d . . . . .
Cl1 Cl -0.23863(3) 0.21751(3) 0.14876(3) 0.02957(9) Uani 1 1 d . . . . .
C1 C 0.19168(10) 0.21585(9) 0.06712(9) 0.0206(2) Uani 1 1 d . . . . .
C14 C 0.51113(10) 0.05100(10) 0.17532(10) 0.0225(2) Uani 1 1 d . . . . .
C2 C 0.09976(10) 0.16087(10) -0.00293(9) 0.0198(2) Uani 1 1 d . . . . .
C5 C -0.18995(10) 0.17794(9) 0.04918(10) 0.0205(2) Uani 1 1 d . . . . .
C9 C 0.42763(10) 0.12715(9) 0.18384(9) 0.01829(19) Uani 1 1 d . . . . .
C16 C 0.51492(11) 0.37261(10) 0.18310(10) 0.0222(2) Uani 1 1 d . . . . .
C4 C -0.06741(10) 0.18571(10) 0.06695(9) 0.0205(2) Uani 1 1 d . . . . .
C3 C -0.02741(10) 0.15314(9) -0.01264(9) 0.0184(2) Uani 1 1 d . . . . .
C6 C -0.27491(11) 0.13984(10) -0.04496(10) 0.0240(2) Uani 1 1 d . . . . .
C7 C -0.23518(11) 0.10617(11) -0.12316(10) 0.0249(2) Uani 1 1 d . . . . .
C8 C -0.11242(11) 0.11133(10) -0.10693(9) 0.0226(2) Uani 1 1 d . . . . .
C15 C 0.40244(10) 0.35125(9) 0.10421(9) 0.0213(2) Uani 1 1 d . . . . .
C10 C 0.40559(14) 0.13270(11) 0.27671(10) 0.0287(3) Uani 1 1 d . . . . .
C11 C 0.46507(16) 0.06111(12) 0.35877(11) 0.0347(3) Uani 1 1 d . . . . .
C12 C 0.54705(13) -0.01570(11) 0.34918(10) 0.0306(3) Uani 1 1 d . . . . .
C17 C 0.55970(13) 0.48011(11) 0.20087(11) 0.0296(3) Uani 1 1 d . . . . .
C13 C 0.57066(12) -0.02040(11) 0.25809(11) 0.0280(3) Uani 1 1 d . . . . .
C18 C 0.49233(16) 0.56576(13) 0.13964(14) 0.0416(4) Uani 1 1 d . . . . .
C19 C 0.38215(19) 0.54408(14) 0.06009(17) 0.0556(5) Uani 1 1 d . . . . .
C20 C 0.33661(16) 0.43735(13) 0.04171(15) 0.0454(4) Uani 1 1 d . . . . .
B1 B 0.34945(12) 0.16213(12) -0.05993(11) 0.0236(2) Uani 1 1 d . . . . .
F1 F 0.17565(7) 0.27761(8) 0.14358(7) 0.0384(2) Uani 1 1 d . . . . .
H2 H 0.1214(15) 0.1229(14) -0.0560(13) 0.025(4) Uiso 1 1 d . . . . .
H4 H -0.0137(16) 0.2119(14) 0.1364(14) 0.031(4) Uiso 1 1 d . . . . .
H6 H -0.3611(15) 0.1396(14) -0.0515(13) 0.028(4) Uiso 1 1 d . . . . .
H8 H -0.0858(15) 0.0897(14) -0.1621(14) 0.028(4) Uiso 1 1 d . . . . .
H7 H -0.2905(17) 0.0791(16) -0.1869(15) 0.037(5) Uiso 1 1 d . . . . .
H16 H 0.5643(16) 0.3139(15) 0.2252(14) 0.029(4) Uiso 1 1 d . . . . .
H17 H 0.6365(18) 0.4949(17) 0.2521(16) 0.042(5) Uiso 1 1 d . . . . .
H20 H 0.259(2) 0.4206(19) -0.0125(17) 0.054(6) Uiso 1 1 d . . . . .
H18 H 0.523(2) 0.640(2) 0.1518(17) 0.054(6) Uiso 1 1 d . . . . .
H19 H 0.336(2) 0.604(2) 0.0166(19) 0.065(7) Uiso 1 1 d . . . . .
H14 H 0.5266(16) 0.0468(15) 0.1130(14) 0.034(5) Uiso 1 1 d . . . . .
H12 H 0.5870(18) -0.0660(17) 0.4044(16) 0.044(5) Uiso 1 1 d . . . . .
H13 H 0.6240(17) -0.0730(16) 0.2519(15) 0.036(5) Uiso 1 1 d . . . . .
H10 H 0.3524(19) 0.1809(18) 0.2833(16) 0.045(5) Uiso 1 1 d . . . . .
H11 H 0.453(2) 0.068(2) 0.4207(19) 0.060(6) Uiso 1 1 d . . . . .
H1A H 0.3120(17) 0.0761(16) -0.0710(15) 0.039(5) Uiso 1 1 d . . . . .
H1B H 0.4453(17) 0.1666(16) -0.0527(15) 0.039(5) Uiso 1 1 d . . . . .
H1C H 0.2872(17) 0.2195(15) -0.1153(15) 0.038(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C15 1.8048(12) . ?
P1 C9 1.8069(11) . ?
P1 C1 1.8085(12) . ?
P1 B1 1.9183(14) . ?
Cl1 C5 1.7398(12) . ?
C1 C2 1.3296(16) . ?
C1 F1 1.3595(13) . ?
C14 C13 1.3904(17) . ?
C14 C9 1.3913(16) . ?
C14 H14 0.941(18) . ?
C2 C3 1.4676(15) . ?
C2 H2 0.974(17) . ?
C5 C6 1.3846(17) . ?
C5 C4 1.3846(15) . ?
C9 C10 1.3960(16) . ?
C16 C15 1.3900(16) . ?
C16 C17 1.3936(18) . ?
C16 H16 0.964(18) . ?
C4 C3 1.4020(16) . ?
C4 H4 0.979(18) . ?
C3 C8 1.4017(16) . ?
C6 C7 1.3866(18) . ?
C6 H6 0.993(17) . ?
C7 C8 1.3903(16) . ?
C7 H7 0.933(19) . ?
C8 H8 0.960(17) . ?
C15 C20 1.3893(18) . ?
C10 C11 1.3856(19) . ?
C10 H10 0.89(2) . ?
C11 C12 1.388(2) . ?
C11 H11 0.92(2) . ?
C12 C13 1.381(2) . ?
C12 H12 0.95(2) . ?
C17 C18 1.384(2) . ?
C17 H17 0.93(2) . ?
C13 H13 0.925(19) . ?
C18 C19 1.376(2) . ?
C18 H18 0.96(2) . ?
C19 C20 1.388(2) . ?
C19 H19 0.97(3) . ?
C20 H20 0.96(2) . ?
B1 H1A 1.121(19) . ?
B1 H1B 1.105(19) . ?
B1 H1C 1.088(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 P1 C9 106.88(5) . . ?
C15 P1 C1 105.32(5) . . ?
C9 P1 C1 104.61(5) . . ?
C15 P1 B1 113.11(6) . . ?
C9 P1 B1 115.14(6) . . ?
C1 P1 B1 110.98(6) . . ?
C2 C1 F1 121.22(10) . . ?
C2 C1 P1 123.80(9) . . ?
F1 C1 P1 114.96(8) . . ?
C13 C14 C9 120.20(12) . . ?
C13 C14 H14 119.7(11) . . ?
C9 C14 H14 120.1(11) . . ?
C1 C2 C3 129.30(11) . . ?
C1 C2 H2 113.7(10) . . ?
C3 C2 H2 117.0(10) . . ?
C6 C5 C4 122.30(11) . . ?
C6 C5 Cl1 118.94(9) . . ?
C4 C5 Cl1 118.76(9) . . ?
C14 C9 C10 119.57(11) . . ?
C14 C9 P1 118.60(9) . . ?
C10 C9 P1 121.78(9) . . ?
C15 C16 C17 120.10(12) . . ?
C15 C16 H16 121.2(10) . . ?
C17 C16 H16 118.7(10) . . ?
C5 C4 C3 119.06(11) . . ?
C5 C4 H4 116.7(10) . . ?
C3 C4 H4 124.2(10) . . ?
C8 C3 C4 118.91(10) . . ?
C8 C3 C2 117.70(10) . . ?
C4 C3 C2 123.39(10) . . ?
C5 C6 C7 118.66(11) . . ?
C5 C6 H6 116.6(10) . . ?
C7 C6 H6 124.7(10) . . ?
C6 C7 C8 120.32(11) . . ?
C6 C7 H7 120.3(12) . . ?
C8 C7 H7 119.4(12) . . ?
C7 C8 C3 120.70(11) . . ?
C7 C8 H8 119.9(10) . . ?
C3 C8 H8 119.3(10) . . ?
C20 C15 C16 119.50(12) . . ?
C20 C15 P1 118.43(10) . . ?
C16 C15 P1 121.76(9) . . ?
C11 C10 C9 119.88(12) . . ?
C11 C10 H10 119.5(13) . . ?
C9 C10 H10 120.6(13) . . ?
C10 C11 C12 120.23(13) . . ?
C10 C11 H11 119.3(15) . . ?
C12 C11 H11 120.4(15) . . ?
C13 C12 C11 120.13(12) . . ?
C13 C12 H12 119.1(12) . . ?
C11 C12 H12 120.8(12) . . ?
C18 C17 C16 120.00(13) . . ?
C18 C17 H17 119.2(13) . . ?
C16 C17 H17 120.7(13) . . ?
C12 C13 C14 119.97(12) . . ?
C12 C13 H13 119.4(12) . . ?
C14 C13 H13 120.6(12) . . ?
C19 C18 C17 119.80(14) . . ?
C19 C18 H18 120.2(13) . . ?
C17 C18 H18 120.0(13) . . ?
C18 C19 C20 120.70(15) . . ?
C18 C19 H19 119.7(15) . . ?
C20 C19 H19 119.6(15) . . ?
C19 C20 C15 119.87(14) . . ?
C19 C20 H20 122.1(13) . . ?
C15 C20 H20 118.0(14) . . ?
P1 B1 H1A 105.9(10) . . ?
P1 B1 H1B 106.7(10) . . ?
H1A B1 H1B 113.6(14) . . ?
P1 B1 H1C 101.7(10) . . ?
H1A B1 H1C 111.7(14) . . ?
H1B B1 H1C 115.9(14) . . ?

_refine_diff_density_max         0.555
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.057

