# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               'RSC Advances'
_journal_coden_cambridge         1500
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_name                'Jinxing Ye'
_publ_contact_author_name        'Jinxing Ye'
_publ_contact_author_email       yejx@ecust.edu.cn

data_mo_dm1195_0m
_database_code_depnum_ccdc_archive 'CCDC 818724'
#TrackingRef '- mo_dm1195_0m.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 Br O2 P'
_chemical_formula_weight         415.25

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'
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'
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   C2

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

_cell_length_a                   27.703(8)
_cell_length_b                   5.8189(16)
_cell_length_c                   12.466(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.008(5)
_cell_angle_gamma                90.00
_cell_volume                     1957.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3302
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      30.27

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    2.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5142
_exptl_absorpt_correction_T_max  0.8983
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6706
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.1105
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         26.99
_reflns_number_total             4066
_reflns_number_gt                2564
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0625P)^2^+5.0189P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4066
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.1837
_refine_ls_wR_factor_gt          0.1598
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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
P1 P 0.33803(5) 0.0172(2) 0.29774(10) 0.0321(3) Uani 1 1 d . . .
Br1 Br 0.56431(4) 0.0532(4) 0.14208(10) 0.1351(7) Uani 1 1 d . . .
C1 C 0.3872(2) 0.2207(9) 0.3558(4) 0.0346(13) Uani 1 1 d . . .
H1A H 0.3746 0.3749 0.3334 0.042 Uiso 1 1 calc R . .
C2 C 0.3987(2) 0.2135(10) 0.4827(5) 0.0420(15) Uani 1 1 d . . .
H2A H 0.3678 0.2174 0.5069 0.050 Uiso 1 1 calc R . .
H2B H 0.4152 0.0696 0.5075 0.050 Uiso 1 1 calc R . .
C3 C 0.4306(2) 0.4072(12) 0.5346(6) 0.0499(18) Uani 1 1 d . . .
H3A H 0.4444 0.3690 0.6110 0.060 Uiso 1 1 calc R . .
H3B H 0.4579 0.4227 0.4984 0.060 Uiso 1 1 calc R . .
C4 C 0.4305(2) 0.1794(10) 0.3054(5) 0.0390(14) Uani 1 1 d . . .
C5 C 0.4413(3) 0.3289(14) 0.2279(6) 0.0567(19) Uani 1 1 d . . .
H5 H 0.4216 0.4580 0.2080 0.068 Uiso 1 1 calc R . .
C6 C 0.4809(3) 0.2912(19) 0.1793(6) 0.072(2) Uani 1 1 d . . .
H6 H 0.4879 0.3954 0.1283 0.087 Uiso 1 1 calc R . .
C7 C 0.5093(2) 0.1027(18) 0.2063(7) 0.070(2) Uani 1 1 d . . .
C8 C 0.5004(3) -0.0489(13) 0.2846(7) 0.064(2) Uani 1 1 d . . .
H8 H 0.5208 -0.1764 0.3036 0.077 Uiso 1 1 calc R . .
C9 C 0.4616(2) -0.0129(12) 0.3349(6) 0.0502(17) Uani 1 1 d . . .
H9 H 0.4559 -0.1151 0.3881 0.060 Uiso 1 1 calc R . .
C10 C 0.32842(17) 0.0412(10) 0.1506(4) 0.0307(11) Uani 1 1 d . . .
C11 C 0.3435(2) -0.1400(11) 0.0932(5) 0.0475(16) Uani 1 1 d . . .
H11 H 0.3583 -0.2693 0.1305 0.057 Uiso 1 1 calc R . .
C12 C 0.3362(3) -0.1259(14) -0.0203(6) 0.059(2) Uani 1 1 d . . .
H12 H 0.3463 -0.2468 -0.0590 0.071 Uiso 1 1 calc R . .
C13 C 0.3146(2) 0.0627(14) -0.0760(5) 0.0546(19) Uani 1 1 d . . .
H13 H 0.3104 0.0711 -0.1520 0.065 Uiso 1 1 calc R . .
C14 C 0.2991(2) 0.2405(13) -0.0192(6) 0.0550(18) Uani 1 1 d . . .
H14 H 0.2842 0.3694 -0.0567 0.066 Uiso 1 1 calc R . .
C15 C 0.3059(2) 0.2263(11) 0.0937(5) 0.0417(15) Uani 1 1 d . . .
H15 H 0.2948 0.3456 0.1317 0.050 Uiso 1 1 calc R . .
C16 C 0.28163(19) 0.1145(10) 0.3287(4) 0.0333(12) Uani 1 1 d . . .
C17 C 0.2413(2) -0.0354(11) 0.3059(5) 0.0476(17) Uani 1 1 d . . .
H17 H 0.2455 -0.1805 0.2779 0.057 Uiso 1 1 calc R . .
C18 C 0.1961(2) 0.0234(17) 0.3231(5) 0.0556(16) Uani 1 1 d . . .
H18 H 0.1697 -0.0791 0.3060 0.067 Uiso 1 1 calc R . .
C19 C 0.1899(2) 0.2364(13) 0.3661(6) 0.0542(18) Uani 1 1 d . . .
H19 H 0.1590 0.2773 0.3778 0.065 Uiso 1 1 calc R . .
C20 C 0.2278(3) 0.3869(13) 0.3915(6) 0.0532(17) Uani 1 1 d . . .
H20 H 0.2232 0.5284 0.4224 0.064 Uiso 1 1 calc R . .
C21 C 0.2742(2) 0.3299(11) 0.3713(5) 0.0416(15) Uani 1 1 d . . .
H21 H 0.3000 0.4358 0.3864 0.050 Uiso 1 1 calc R . .
O1 O 0.40664(18) 0.6180(8) 0.5305(4) 0.0614(14) Uani 1 1 d . . .
H1 H 0.3952 0.6533 0.4661 0.092 Uiso 1 1 calc R . .
O2 O 0.35002(16) -0.2246(7) 0.3348(3) 0.0449(10) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0336(7) 0.0262(7) 0.0333(7) 0.0011(7) 0.0008(5) 0.0004(7)
Br1 0.0753(6) 0.2210(17) 0.1227(9) -0.0107(11) 0.0513(6) 0.0386(10)
C1 0.040(3) 0.021(3) 0.038(3) 0.002(2) -0.003(2) 0.001(2)
C2 0.042(3) 0.037(3) 0.041(3) -0.001(3) -0.003(3) 0.000(3)
C3 0.048(4) 0.045(4) 0.046(4) -0.013(3) -0.013(3) 0.005(3)
C4 0.037(3) 0.036(3) 0.039(3) 0.001(3) -0.003(2) -0.001(3)
C5 0.052(4) 0.070(5) 0.048(4) 0.016(4) 0.011(3) 0.009(4)
C6 0.044(4) 0.112(7) 0.061(5) 0.022(5) 0.011(4) 0.006(5)
C7 0.033(3) 0.111(7) 0.068(5) -0.019(5) 0.013(3) 0.005(4)
C8 0.037(4) 0.059(6) 0.091(6) -0.019(4) 0.003(4) 0.009(3)
C9 0.050(4) 0.033(4) 0.065(4) 0.000(3) 0.008(3) 0.002(3)
C10 0.028(2) 0.029(3) 0.032(2) 0.000(3) 0.0021(19) -0.004(3)
C11 0.052(4) 0.040(4) 0.047(4) -0.002(3) 0.005(3) 0.013(3)
C12 0.079(5) 0.061(5) 0.043(4) -0.015(4) 0.023(4) 0.008(4)
C13 0.053(4) 0.075(6) 0.035(3) 0.004(4) 0.010(3) -0.004(4)
C14 0.050(4) 0.061(5) 0.050(4) 0.012(4) 0.003(3) 0.013(4)
C15 0.041(3) 0.043(4) 0.041(3) -0.001(3) 0.011(3) 0.010(3)
C16 0.035(3) 0.037(3) 0.025(3) 0.001(2) 0.002(2) -0.001(3)
C17 0.058(4) 0.043(5) 0.041(3) -0.006(3) 0.009(3) -0.012(3)
C18 0.038(3) 0.065(4) 0.062(4) 0.000(5) 0.009(3) -0.013(4)
C19 0.039(3) 0.069(5) 0.059(4) 0.009(4) 0.021(3) 0.002(4)
C20 0.066(5) 0.044(4) 0.056(4) 0.004(3) 0.030(3) 0.004(4)
C21 0.046(3) 0.039(4) 0.044(3) 0.004(3) 0.019(3) -0.003(3)
O1 0.070(3) 0.045(3) 0.058(3) -0.009(2) -0.009(2) 0.011(3)
O2 0.059(3) 0.029(2) 0.043(2) 0.0051(18) 0.0020(19) 0.000(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 O2 1.495(4) . ?
P1 C16 1.784(6) . ?
P1 C10 1.799(5) . ?
P1 C1 1.827(5) . ?
Br1 C7 1.896(7) . ?
C1 C4 1.493(8) . ?
C1 C2 1.542(8) . ?
C1 H1A 0.9800 . ?
C2 C3 1.487(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O1 1.390(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.382(9) . ?
C4 C9 1.410(9) . ?
C5 C6 1.385(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.347(13) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(12) . ?
C8 C9 1.378(10) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.361(8) . ?
C10 C11 1.391(8) . ?
C11 C12 1.385(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(9) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.394(8) . ?
C16 C17 1.394(8) . ?
C17 C18 1.363(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.349(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.405(9) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
O1 H1 0.8200 . ?

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
O2 P1 C16 112.1(3) . . ?
O2 P1 C10 111.1(3) . . ?
C16 P1 C10 105.1(2) . . ?
O2 P1 C1 113.2(2) . . ?
C16 P1 C1 108.6(3) . . ?
C10 P1 C1 106.2(3) . . ?
C4 C1 C2 115.3(4) . . ?
C4 C1 P1 109.0(4) . . ?
C2 C1 P1 110.6(4) . . ?
C4 C1 H1A 107.2 . . ?
C2 C1 H1A 107.2 . . ?
P1 C1 H1A 107.2 . . ?
C3 C2 C1 113.0(5) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
O1 C3 C2 115.0(5) . . ?
O1 C3 H3A 108.5 . . ?
C2 C3 H3A 108.5 . . ?
O1 C3 H3B 108.5 . . ?
C2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C9 117.7(6) . . ?
C5 C4 C1 121.0(5) . . ?
C9 C4 C1 121.3(5) . . ?
C4 C5 C6 121.7(7) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 119.7(8) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.7(7) . . ?
C6 C7 Br1 119.8(7) . . ?
C8 C7 Br1 119.4(7) . . ?
C7 C8 C9 120.5(7) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 119.7(7) . . ?
C8 C9 H9 120.2 . . ?
C4 C9 H9 120.2 . . ?
C15 C10 C11 119.2(5) . . ?
C15 C10 P1 122.5(4) . . ?
C11 C10 P1 118.2(4) . . ?
C12 C11 C10 119.3(6) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C13 C12 C11 120.9(6) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 119.7(6) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 119.5(6) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C10 C15 C14 121.3(6) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C21 C16 C17 117.4(5) . . ?
C21 C16 P1 125.4(4) . . ?
C17 C16 P1 117.2(5) . . ?
C18 C17 C16 122.2(7) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C17 C18 C19 119.1(7) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C20 C19 C18 121.2(6) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 120.0(7) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 120.0(6) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C3 O1 H1 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 1.96 2.744(6) 160.7 1_565

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.072