# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_210717f
_database_code_depnum_ccdc_archive 'CCDC 2098034'
loop_
_audit_author_name
_audit_author_address
'Xiaowu Wang'
;Qingdao University of Science and Technology
China
;
_audit_update_record             
;
2021-07-21 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 Br P'
_chemical_formula_weight         383.25

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'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8668(11)
_cell_length_b                   9.9356(9)
_cell_length_c                   17.4186(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.376(4)
_cell_angle_gamma                90.00
_cell_volume                     1813.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2007
_cell_measurement_theta_min      2.342
_cell_measurement_theta_max      26.817

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      1.404
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    2.352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5908
_exptl_absorpt_correction_T_max  0.8341
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8673
_diffrn_reflns_av_R_equivalents  0.1065
_diffrn_reflns_av_sigmaI/netI    0.0995
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3195
_reflns_number_gt                1898
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0732P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0040(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3195
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1626
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.61724(6) 0.86267(7) 0.16686(4) 0.0603(3) Uani 1 1 d . . .
P1 P 0.23264(15) 0.67959(17) 0.46873(9) 0.0458(4) Uani 1 1 d . . .
C1 C 0.2796(8) 0.3186(9) 0.5519(6) 0.097(3) Uani 1 1 d . . .
H1A H 0.3080 0.2782 0.5115 0.116 Uiso 1 1 calc R . .
H1B H 0.2484 0.2658 0.5867 0.116 Uiso 1 1 calc R . .
C2 C 0.2834(7) 0.4479(9) 0.5596(4) 0.071(2) Uani 1 1 d . . .
H2 H 0.2543 0.4849 0.6006 0.086 Uiso 1 1 calc R . .
C3 C 0.3305(5) 0.5404(7) 0.5082(4) 0.0531(16) Uani 1 1 d . . .
H3A H 0.3448 0.4890 0.4641 0.064 Uiso 1 1 calc R . .
H3B H 0.4127 0.5746 0.5384 0.064 Uiso 1 1 calc R . .
C4 C 0.1853(5) 0.7651(6) 0.5455(3) 0.0480(15) Uani 1 1 d . . .
C5 C 0.0591(6) 0.7980(7) 0.5402(4) 0.0604(18) Uani 1 1 d . . .
H5 H -0.0055 0.7692 0.4969 0.072 Uiso 1 1 calc R . .
C6 C 0.0306(7) 0.8720(8) 0.5985(5) 0.076(2) Uani 1 1 d . . .
H6 H -0.0538 0.8952 0.5945 0.091 Uiso 1 1 calc R . .
C7 C 0.1238(7) 0.9125(8) 0.6628(4) 0.070(2) Uani 1 1 d . . .
H7 H 0.1030 0.9623 0.7028 0.084 Uiso 1 1 calc R . .
C8 C 0.2472(7) 0.8806(8) 0.6688(4) 0.068(2) Uani 1 1 d . . .
H8 H 0.3109 0.9104 0.7124 0.082 Uiso 1 1 calc R . .
C9 C 0.2787(6) 0.8053(7) 0.6116(4) 0.0595(18) Uani 1 1 d . . .
H9 H 0.3633 0.7810 0.6172 0.071 Uiso 1 1 calc R . .
C10 C 0.0953(5) 0.6324(6) 0.3931(3) 0.0447(15) Uani 1 1 d . . .
C11 C 0.0228(6) 0.7313(7) 0.3472(4) 0.0601(18) Uani 1 1 d . . .
H11 H 0.0476 0.8208 0.3559 0.072 Uiso 1 1 calc R . .
C12 C -0.0848(7) 0.7000(9) 0.2894(4) 0.074(2) Uani 1 1 d . . .
H12 H -0.1333 0.7676 0.2587 0.089 Uiso 1 1 calc R . .
C13 C -0.1207(6) 0.5694(10) 0.2769(4) 0.073(2) Uani 1 1 d . . .
H13 H -0.1948 0.5477 0.2380 0.088 Uiso 1 1 calc R . .
C14 C -0.0498(7) 0.4706(8) 0.3204(4) 0.068(2) Uani 1 1 d . . .
H14 H -0.0745 0.3813 0.3104 0.082 Uiso 1 1 calc R . .
C15 C 0.0581(6) 0.5007(7) 0.3790(3) 0.0582(17) Uani 1 1 d . . .
H15 H 0.1059 0.4322 0.4092 0.070 Uiso 1 1 calc R . .
C16 C 0.3200(5) 0.7931(7) 0.4255(3) 0.0480(16) Uani 1 1 d . . .
C17 C 0.3249(6) 0.9274(7) 0.4411(4) 0.0613(18) Uani 1 1 d . . .
H17 H 0.2862 0.9615 0.4787 0.074 Uiso 1 1 calc R . .
C18 C 0.3867(7) 1.0133(8) 0.4017(5) 0.073(2) Uani 1 1 d . . .
H18 H 0.3903 1.1050 0.4126 0.088 Uiso 1 1 calc R . .
C19 C 0.4425(7) 0.9623(9) 0.3465(5) 0.074(2) Uani 1 1 d . . .
H19 H 0.4832 1.0201 0.3192 0.089 Uiso 1 1 calc R . .
C20 C 0.4395(8) 0.8293(9) 0.3309(5) 0.080(2) Uani 1 1 d . . .
H20 H 0.4780 0.7956 0.2932 0.096 Uiso 1 1 calc R . .
C21 C 0.3797(7) 0.7446(9) 0.3708(4) 0.073(2) Uani 1 1 d . . .
H21 H 0.3793 0.6526 0.3609 0.088 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
P1 C16 1.766(6) . ?
P1 C3 1.769(6) . ?
P1 C4 1.771(6) . ?
P1 C10 1.773(6) . ?
C1 C2 1.292(10) . ?
C1 H1A 0.9300 . ?
C1 H1B 0.9300 . ?
C2 C3 1.466(9) . ?
C2 H2 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.378(8) . ?
C4 C5 1.389(8) . ?
C5 C6 1.355(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.356(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.355(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.359(8) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.372(8) . ?
C10 C11 1.375(8) . ?
C11 C12 1.362(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.356(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.349(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.361(9) . ?
C16 C21 1.374(9) . ?
C17 C18 1.376(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.363(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.347(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.361(10) . ?
C20 H20 0.9300 . ?
C21 H21 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
C16 P1 C3 109.2(3) . . ?
C16 P1 C4 108.2(3) . . ?
C3 P1 C4 110.3(3) . . ?
C16 P1 C10 107.1(3) . . ?
C3 P1 C10 112.5(3) . . ?
C4 P1 C10 109.4(3) . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 C3 124.5(8) . . ?
C1 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C2 C3 P1 117.1(5) . . ?
C2 C3 H3A 108.0 . . ?
P1 C3 H3A 108.0 . . ?
C2 C3 H3B 108.0 . . ?
P1 C3 H3B 108.0 . . ?
H3A C3 H3B 107.3 . . ?
C9 C4 C5 118.8(6) . . ?
C9 C4 P1 118.3(5) . . ?
C5 C4 P1 122.8(5) . . ?
C6 C5 C4 119.8(6) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.7(7) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.1(7) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.6(6) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 120.0(6) . . ?
C8 C9 H9 120.0 . . ?
C4 C9 H9 120.0 . . ?
C15 C10 C11 118.8(6) . . ?
C15 C10 P1 122.4(5) . . ?
C11 C10 P1 118.8(5) . . ?
C12 C11 C10 120.9(7) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 119.4(7) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.6(6) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.6(7) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 119.7(7) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
C17 C16 C21 118.8(6) . . ?
C17 C16 P1 122.6(5) . . ?
C21 C16 P1 118.6(6) . . ?
C16 C17 C18 120.4(7) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.3(8) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C20 C19 C18 121.0(7) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 119.5(8) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C16 121.0(8) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?

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
C1 C2 C3 P1 130.8(8) . . . . ?
C16 P1 C3 C2 168.8(5) . . . . ?
C4 P1 C3 C2 50.1(6) . . . . ?
C10 P1 C3 C2 -72.4(6) . . . . ?
C16 P1 C4 C9 -66.3(6) . . . . ?
C3 P1 C4 C9 53.1(6) . . . . ?
C10 P1 C4 C9 177.4(5) . . . . ?
C16 P1 C4 C5 111.0(6) . . . . ?
C3 P1 C4 C5 -129.6(6) . . . . ?
C10 P1 C4 C5 -5.3(7) . . . . ?
C9 C4 C5 C6 2.1(11) . . . . ?
P1 C4 C5 C6 -175.2(6) . . . . ?
C4 C5 C6 C7 -1.2(12) . . . . ?
C5 C6 C7 C8 0.8(13) . . . . ?
C6 C7 C8 C9 -1.5(13) . . . . ?
C7 C8 C9 C4 2.4(12) . . . . ?
C5 C4 C9 C8 -2.7(10) . . . . ?
P1 C4 C9 C8 174.7(6) . . . . ?
C16 P1 C10 C15 132.2(5) . . . . ?
C3 P1 C10 C15 12.1(6) . . . . ?
C4 P1 C10 C15 -110.8(5) . . . . ?
C16 P1 C10 C11 -48.4(6) . . . . ?
C3 P1 C10 C11 -168.4(5) . . . . ?
C4 P1 C10 C11 68.6(5) . . . . ?
C15 C10 C11 C12 0.6(10) . . . . ?
P1 C10 C11 C12 -178.8(5) . . . . ?
C10 C11 C12 C13 0.0(10) . . . . ?
C11 C12 C13 C14 -1.0(11) . . . . ?
C12 C13 C14 C15 1.4(11) . . . . ?
C13 C14 C15 C10 -0.7(10) . . . . ?
C11 C10 C15 C14 -0.2(9) . . . . ?
P1 C10 C15 C14 179.2(5) . . . . ?
C3 P1 C16 C17 -131.2(5) . . . . ?
C4 P1 C16 C17 -11.2(6) . . . . ?
C10 P1 C16 C17 106.6(5) . . . . ?
C3 P1 C16 C21 52.3(6) . . . . ?
C4 P1 C16 C21 172.3(5) . . . . ?
C10 P1 C16 C21 -69.9(6) . . . . ?
C21 C16 C17 C18 1.1(10) . . . . ?
P1 C16 C17 C18 -175.4(5) . . . . ?
C16 C17 C18 C19 0.3(10) . . . . ?
C17 C18 C19 C20 -1.0(11) . . . . ?
C18 C19 C20 C21 0.1(12) . . . . ?
C19 C20 C21 C16 1.4(12) . . . . ?
C17 C16 C21 C20 -2.0(10) . . . . ?
P1 C16 C21 C20 174.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.677
_refine_diff_density_min         -1.583
_refine_diff_density_rms         0.118
####################################################################### 
# 
# 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_210717g
_database_code_depnum_ccdc_archive 'CCDC 2098035'
loop_
_audit_author_name
_audit_author_address
'Xiaowu Wang'
;Qingdao University of Science and Technology
China
;
_audit_update_record             
;
2021-07-21 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Br P'
_chemical_formula_weight         397.28

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'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.3364(13)
_cell_length_b                   10.3332(12)
_cell_length_c                   18.1348(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.699(3)
_cell_angle_gamma                90.00
_cell_volume                     2054.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2429
_cell_measurement_theta_min      2.496
_cell_measurement_theta_max      24.193

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      1.284
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    2.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4903
_exptl_absorpt_correction_T_max  0.6038
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8905
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_sigmaI/netI    0.0857
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3614
_reflns_number_gt                2251
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0684P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3614
_refine_ls_number_parameters     224
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.050
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.61447(5) 0.37338(5) 0.16811(3) 0.0562(2) Uani 1 1 d . . .
P1 P 0.22971(11) 0.19346(11) 0.46233(6) 0.0388(3) Uani 1 1 d . . .
C1 C 0.3186(13) -0.2429(12) 0.5339(7) 0.103(4) Uani 0.583(9) 1 d PDU A 1
H1A H 0.2969 -0.2198 0.4827 0.124 Uiso 0.583(9) 1 calc PR A 1
H1B H 0.3434 -0.3271 0.5480 0.124 Uiso 0.583(9) 1 calc PR A 1
C2 C 0.3142(16) -0.1557(9) 0.5870(7) 0.093(3) Uani 0.583(9) 1 d PDU A 1
H2 H 0.3357 -0.1782 0.6383 0.111 Uiso 0.583(9) 1 calc PR A 1
C1' C 0.2887(19) -0.2688(14) 0.5836(11) 0.103(4) Uani 0.417(9) 1 d PD A 2
H1'1 H 0.2483 -0.2706 0.6223 0.124 Uiso 0.417(9) 1 calc PR A 2
H1'2 H 0.3172 -0.3453 0.5673 0.124 Uiso 0.417(9) 1 calc PR A 2
C2' C 0.306(2) -0.1585(10) 0.5522(11) 0.093(3) Uani 0.417(9) 1 d PD A 2
H2' H 0.3468 -0.1684 0.5143 0.111 Uiso 0.417(9) 1 calc PR A 2
C3 C 0.2738(6) -0.0203(5) 0.5630(3) 0.0713(17) Uani 1 1 d DU . .
H3A H 0.2885 0.0312 0.6091 0.086 Uiso 0.583(9) 1 calc PR A 1
H3B H 0.1861 -0.0233 0.5423 0.086 Uiso 0.583(9) 1 calc PR A 1
H3'A H 0.3146 0.0047 0.6147 0.086 Uiso 0.417(9) 1 d PR A 2
H3'B H 0.1871 -0.0049 0.5550 0.086 Uiso 0.417(9) 1 d PR A 2
C4 C 0.3266(4) 0.0576(4) 0.5050(2) 0.0475(12) Uani 1 1 d . A .
H4A H 0.3364 -0.0002 0.4648 0.057 Uiso 1 1 calc R . .
H4B H 0.4067 0.0902 0.5308 0.057 Uiso 1 1 calc R . .
C5 C 0.1839(4) 0.2810(4) 0.5386(2) 0.0399(11) Uani 1 1 d . . .
C6 C 0.0605(5) 0.3085(5) 0.5353(3) 0.0574(14) Uani 1 1 d . . .
H6 H -0.0011 0.2809 0.4940 0.069 Uiso 1 1 calc R . .
C7 C 0.0317(6) 0.3787(5) 0.5959(4) 0.0758(18) Uani 1 1 d . . .
H7 H -0.0493 0.3953 0.5950 0.091 Uiso 1 1 calc R . .
C8 C 0.1252(6) 0.4229(6) 0.6570(3) 0.0698(17) Uani 1 1 d . . .
H8 H 0.1060 0.4701 0.6961 0.084 Uiso 1 1 calc R . .
C9 C 0.2462(6) 0.3968(5) 0.6596(3) 0.0651(16) Uani 1 1 d . . .
H9 H 0.3077 0.4271 0.7002 0.078 Uiso 1 1 calc R . .
C10 C 0.2764(5) 0.3251(5) 0.6014(3) 0.0573(14) Uani 1 1 d . . .
H10 H 0.3576 0.3065 0.6041 0.069 Uiso 1 1 calc R . .
C11 C 0.3105(4) 0.3037(4) 0.4137(3) 0.0439(11) Uani 1 1 d . . .
C12 C 0.3261(5) 0.4352(5) 0.4316(3) 0.0575(14) Uani 1 1 d . . .
H12 H 0.2978 0.4691 0.4714 0.069 Uiso 1 1 calc R . .
C13 C 0.3852(5) 0.5176(6) 0.3892(3) 0.0729(17) Uani 1 1 d . . .
H13 H 0.3959 0.6048 0.4017 0.087 Uiso 1 1 calc R . .
C14 C 0.4267(5) 0.4683(7) 0.3295(3) 0.0723(17) Uani 1 1 d . . .
H14 H 0.4649 0.5224 0.3017 0.087 Uiso 1 1 calc R . .
C15 C 0.4116(6) 0.3384(6) 0.3111(4) 0.0769(18) Uani 1 1 d . . .
H15 H 0.4400 0.3058 0.2711 0.092 Uiso 1 1 calc R . .
C16 C 0.3535(5) 0.2549(5) 0.3524(3) 0.0625(15) Uani 1 1 d . . .
H16 H 0.3436 0.1678 0.3394 0.075 Uiso 1 1 calc R . .
C17 C 0.0960(4) 0.1363(4) 0.3913(3) 0.0435(12) Uani 1 1 d . . .
C18 C 0.0179(5) 0.2287(5) 0.3454(3) 0.0598(14) Uani 1 1 d . . .
H18 H 0.0356 0.3165 0.3521 0.072 Uiso 1 1 calc R . .
C19 C -0.0862(6) 0.1882(7) 0.2896(4) 0.0821(19) Uani 1 1 d . . .
H19 H -0.1376 0.2494 0.2604 0.099 Uiso 1 1 calc R . .
C20 C -0.1127(6) 0.0574(9) 0.2781(3) 0.085(2) Uani 1 1 d . . .
H20 H -0.1815 0.0313 0.2411 0.102 Uiso 1 1 calc R . .
C21 C -0.0356(6) -0.0354(7) 0.3222(3) 0.0788(19) Uani 1 1 d . . .
H21 H -0.0537 -0.1229 0.3143 0.095 Uiso 1 1 calc R . .
C22 C 0.0691(5) 0.0031(5) 0.3785(3) 0.0569(14) Uani 1 1 d . . .
H22 H 0.1204 -0.0589 0.4072 0.068 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
P1 C17 1.821(5) . ?
P1 C11 1.823(5) . ?
P1 C4 1.829(4) . ?
P1 C5 1.834(4) . ?
C1 C2 1.328(9) . ?
C1 H1A 0.9300 . ?
C1 H1B 0.9300 . ?
C2 C3 1.502(8) . ?
C2 H2 0.9300 . ?
C1' C2' 1.310(10) . ?
C1' H1'1 0.9300 . ?
C1' H1'2 0.9300 . ?
C2' C3 1.498(9) . ?
C2' H2' 0.9300 . ?
C3 C4 1.559(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 H3'A 0.9700 . ?
C3 H3'B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.413(6) . ?
C5 C6 1.414(6) . ?
C6 C7 1.422(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.402(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.401(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.398(6) . ?
C11 C16 1.414(6) . ?
C12 C13 1.423(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.410(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.416(6) . ?
C17 C18 1.419(6) . ?
C18 C19 1.409(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.389(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.403(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.413(7) . ?
C21 H21 0.9300 . ?
C22 H22 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
C17 P1 C11 106.9(2) . . ?
C17 P1 C4 110.7(2) . . ?
C11 P1 C4 111.2(2) . . ?
C17 P1 C5 110.5(2) . . ?
C11 P1 C5 109.3(2) . . ?
C4 P1 C5 108.3(2) . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 C3 119.1(10) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2' C1' H1'1 120.0 . . ?
C2' C1' H1'2 120.0 . . ?
H1'1 C1' H1'2 120.0 . . ?
C1' C2' C3 135.0(16) . . ?
C1' C2' H2' 112.5 . . ?
C3 C2' H2' 112.5 . . ?
C2' C3 C2 23.6(8) . . ?
C2' C3 C4 105.0(8) . . ?
C2 C3 C4 122.4(7) . . ?
C2' C3 H3A 129.9 . . ?
C2 C3 H3A 106.7 . . ?
C4 C3 H3A 106.7 . . ?
C2' C3 H3B 100.1 . . ?
C2 C3 H3B 106.7 . . ?
C4 C3 H3B 106.7 . . ?
H3A C3 H3B 106.6 . . ?
C2' C3 H3'A 108.0 . . ?
C2 C3 H3'A 86.1 . . ?
C4 C3 H3'A 110.2 . . ?
H3A C3 H3'A 23.6 . . ?
H3B C3 H3'A 124.9 . . ?
C2' C3 H3'B 113.8 . . ?
C2 C3 H3'B 114.7 . . ?
C4 C3 H3'B 111.3 . . ?
H3A C3 H3'B 89.1 . . ?
H3B C3 H3'B 17.6 . . ?
H3'A C3 H3'B 108.5 . . ?
C3 C4 P1 112.9(3) . . ?
C3 C4 H4A 109.0 . . ?
P1 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
P1 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C10 C5 C6 119.5(4) . . ?
C10 C5 P1 118.2(4) . . ?
C6 C5 P1 122.2(4) . . ?
C5 C6 C7 119.2(5) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 120.1(5) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 120.4(5) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.4(5) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 120.3(5) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C12 C11 C16 118.7(4) . . ?
C12 C11 P1 123.0(4) . . ?
C16 C11 P1 118.3(4) . . ?
C11 C12 C13 120.4(5) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.0(5) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.8(5) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.0(5) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C22 C17 C18 118.8(5) . . ?
C22 C17 P1 122.4(4) . . ?
C18 C17 P1 118.7(4) . . ?
C19 C18 C17 120.3(5) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.5(6) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.0(6) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.5(6) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 119.9(5) . . ?
C21 C22 H22 120.1 . . ?
C17 C22 H22 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
C1' C2' C3 C2 38(2) . . . . ?
C1' C2' C3 C4 179(3) . . . . ?
C1 C2 C3 C2' -2(3) . . . . ?
C1 C2 C3 C4 -48.3(19) . . . . ?
C2' C3 C4 P1 143.4(11) . . . . ?
C2 C3 C4 P1 161.0(8) . . . . ?
C17 P1 C4 C3 -75.2(4) . . . . ?
C11 P1 C4 C3 166.2(3) . . . . ?
C5 P1 C4 C3 46.1(4) . . . . ?
C17 P1 C5 C10 176.0(4) . . . . ?
C11 P1 C5 C10 -66.7(4) . . . . ?
C4 P1 C5 C10 54.6(4) . . . . ?
C17 P1 C5 C6 -5.9(5) . . . . ?
C11 P1 C5 C6 111.4(4) . . . . ?
C4 P1 C5 C6 -127.3(4) . . . . ?
C10 C5 C6 C7 -0.8(7) . . . . ?
P1 C5 C6 C7 -178.9(4) . . . . ?
C5 C6 C7 C8 1.7(8) . . . . ?
C6 C7 C8 C9 -1.1(9) . . . . ?
C7 C8 C9 C10 -0.4(9) . . . . ?
C8 C9 C10 C5 1.3(8) . . . . ?
C6 C5 C10 C9 -0.7(7) . . . . ?
P1 C5 C10 C9 177.5(4) . . . . ?
C17 P1 C11 C12 116.2(4) . . . . ?
C4 P1 C11 C12 -122.8(4) . . . . ?
C5 P1 C11 C12 -3.3(4) . . . . ?
C17 P1 C11 C16 -60.3(4) . . . . ?
C4 P1 C11 C16 60.6(4) . . . . ?
C5 P1 C11 C16 -179.8(4) . . . . ?
C16 C11 C12 C13 -0.6(7) . . . . ?
P1 C11 C12 C13 -177.1(4) . . . . ?
C11 C12 C13 C14 0.5(8) . . . . ?
C12 C13 C14 C15 -0.4(9) . . . . ?
C13 C14 C15 C16 0.3(9) . . . . ?
C14 C15 C16 C11 -0.3(9) . . . . ?
C12 C11 C16 C15 0.4(7) . . . . ?
P1 C11 C16 C15 177.1(4) . . . . ?
C11 P1 C17 C22 127.0(4) . . . . ?
C4 P1 C17 C22 5.7(5) . . . . ?
C5 P1 C17 C22 -114.2(4) . . . . ?
C11 P1 C17 C18 -51.0(4) . . . . ?
C4 P1 C17 C18 -172.3(4) . . . . ?
C5 P1 C17 C18 67.8(4) . . . . ?
C22 C17 C18 C19 1.8(8) . . . . ?
P1 C17 C18 C19 179.8(4) . . . . ?
C17 C18 C19 C20 -1.1(9) . . . . ?
C18 C19 C20 C21 0.2(9) . . . . ?
C19 C20 C21 C22 -0.1(9) . . . . ?
C20 C21 C22 C17 0.8(8) . . . . ?
C18 C17 C22 C21 -1.6(7) . . . . ?
P1 C17 C22 C21 -179.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.631
_refine_diff_density_min         -1.227
_refine_diff_density_rms         0.103
