# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       jlzhang@chem.ecnu.edu.cn
_publ_contact_author_name        'Junliang Zhang'
loop_
_publ_author_name
'Yanqing Zhang'
'Junliang Zhang'

data_(1R,_2S)-1j
_database_code_depnum_ccdc_archive 'CCDC 837842'
#TrackingRef '(1R,_2S)-1j.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 Br O'
_chemical_formula_weight         339.22

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   5.3417(12)
_cell_length_b                   9.098(2)
_cell_length_c                   32.164(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1563.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5563
_exptl_absorpt_correction_T_max  0.9301
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14433
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2761
_reflns_number_gt                1914
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0175P)^2^+0.4436P] 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   0.005(14)
_refine_ls_number_reflns         2761
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.52297(9) 0.91349(5) 0.133435(14) 0.07732(19) Uani 1 1 d . . .
O1 O -0.3195(6) 0.1584(3) 0.01968(10) 0.0787(9) Uani 1 1 d . . .
C1 C 0.1718(8) 0.6167(4) 0.05587(12) 0.0560(11) Uani 1 1 d . . .
H1A H 0.1837 0.5912 0.0279 0.067 Uiso 1 1 calc R . .
C2 C 0.3299(8) 0.7220(4) 0.07154(13) 0.0609(11) Uani 1 1 d . . .
H2A H 0.4487 0.7652 0.0543 0.073 Uiso 1 1 calc R . .
C3 C 0.3143(8) 0.7642(5) 0.11253(13) 0.0561(10) Uani 1 1 d . . .
C4 C 0.1393(8) 0.6985(5) 0.13754(13) 0.0628(11) Uani 1 1 d . . .
H4A H 0.1258 0.7270 0.1652 0.075 Uiso 1 1 calc R . .
C5 C -0.0170(9) 0.5907(5) 0.12224(10) 0.0620(10) Uani 1 1 d . . .
H5A H -0.1319 0.5462 0.1399 0.074 Uiso 1 1 calc R . .
C6 C -0.0058(8) 0.5472(3) 0.08070(10) 0.0484(9) Uani 1 1 d . . .
C7 C -0.1647(7) 0.4321(4) 0.06220(12) 0.0527(10) Uani 1 1 d . . .
H7A H -0.1652 0.4335 0.0317 0.063 Uiso 1 1 calc R . .
C8 C -0.3984(7) 0.3761(4) 0.08018(12) 0.0604(12) Uani 1 1 d . . .
H8A H -0.5337 0.3530 0.0611 0.072 Uiso 1 1 calc R . .
H8B H -0.4520 0.4175 0.1065 0.072 Uiso 1 1 calc R . .
C9 C -0.1781(7) 0.2745(4) 0.08079(11) 0.0494(10) Uani 1 1 d . . .
C10 C -0.0587(7) 0.2428(4) 0.11993(12) 0.0516(10) Uani 1 1 d . . .
C11 C 0.0335(8) 0.2191(4) 0.15274(11) 0.0535(10) Uani 1 1 d . . .
C12 C 0.1356(8) 0.1906(4) 0.19305(11) 0.0496(10) Uani 1 1 d . . .
C13 C 0.3389(9) 0.2684(5) 0.20761(13) 0.0700(12) Uani 1 1 d . . .
H13A H 0.4146 0.3379 0.1905 0.084 Uiso 1 1 calc R . .
C14 C 0.4317(9) 0.2455(6) 0.24684(13) 0.0770(13) Uani 1 1 d . . .
H14A H 0.5671 0.3004 0.2563 0.092 Uiso 1 1 calc R . .
C15 C 0.3265(9) 0.1430(5) 0.27185(14) 0.0708(13) Uani 1 1 d . . .
H15A H 0.3904 0.1274 0.2984 0.085 Uiso 1 1 calc R . .
C16 C 0.1291(10) 0.0632(5) 0.25844(13) 0.0746(13) Uani 1 1 d . . .
H16A H 0.0584 -0.0076 0.2757 0.089 Uiso 1 1 calc R . .
C17 C 0.0329(8) 0.0863(5) 0.21948(11) 0.0655(10) Uani 1 1 d . . .
H17A H -0.1036 0.0312 0.2106 0.079 Uiso 1 1 calc R . .
C18 C -0.1724(8) 0.1569(4) 0.04819(13) 0.0543(11) Uani 1 1 d . . .
C19 C 0.0265(9) 0.0438(4) 0.05104(11) 0.0659(12) Uani 1 1 d . . .
H19A H 0.0082 -0.0250 0.0286 0.099 Uiso 1 1 calc R . .
H19B H 0.0128 -0.0070 0.0771 0.099 Uiso 1 1 calc R . .
H19C H 0.1875 0.0903 0.0492 0.099 Uiso 1 1 calc R . .

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
Br1 0.0778(3) 0.0641(3) 0.0901(3) -0.0088(2) -0.0147(3) 0.0014(3)
O1 0.076(2) 0.081(2) 0.079(2) -0.0246(17) -0.0343(18) 0.0135(17)
C1 0.077(3) 0.047(3) 0.044(2) -0.004(2) 0.005(2) 0.013(3)
C2 0.074(3) 0.044(3) 0.064(3) 0.003(2) 0.008(2) 0.002(2)
C3 0.058(3) 0.054(3) 0.056(3) -0.002(2) -0.007(2) 0.018(2)
C4 0.068(3) 0.071(3) 0.050(2) -0.013(2) -0.003(2) 0.009(2)
C5 0.063(2) 0.072(3) 0.051(2) -0.006(2) 0.006(2) 0.003(3)
C6 0.051(2) 0.044(2) 0.049(2) -0.0010(16) -0.001(2) 0.013(2)
C7 0.055(2) 0.056(3) 0.048(2) 0.003(2) -0.0044(19) 0.013(2)
C8 0.050(3) 0.070(3) 0.061(2) -0.011(2) -0.006(2) 0.011(2)
C9 0.049(2) 0.053(3) 0.047(2) -0.001(2) -0.0002(19) 0.007(2)
C10 0.048(3) 0.056(2) 0.051(2) 0.000(2) -0.002(2) 0.003(2)
C11 0.057(3) 0.053(2) 0.050(2) -0.0026(19) -0.003(2) 0.009(2)
C12 0.056(3) 0.049(3) 0.043(2) -0.002(2) -0.002(2) 0.012(2)
C13 0.075(3) 0.078(3) 0.058(3) 0.012(2) -0.007(3) -0.011(3)
C14 0.074(3) 0.094(3) 0.063(3) 0.006(3) -0.011(2) -0.022(3)
C15 0.076(3) 0.087(4) 0.050(3) 0.003(2) -0.010(3) 0.005(3)
C16 0.094(4) 0.071(3) 0.059(3) 0.016(2) 0.005(2) -0.008(3)
C17 0.068(3) 0.070(3) 0.059(2) 0.001(2) -0.002(2) -0.009(3)
C18 0.048(3) 0.054(3) 0.062(3) -0.002(2) 0.000(2) -0.005(2)
C19 0.069(3) 0.064(3) 0.065(3) -0.0085(19) 0.000(3) 0.018(3)

_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 1.881(4) . ?
O1 C18 1.208(4) . ?
C1 C2 1.373(5) . ?
C1 C6 1.392(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.376(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.370(5) . ?
C4 C5 1.379(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.395(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.473(5) . ?
C7 C8 1.467(5) . ?
C7 C9 1.555(5) . ?
C7 H7A 0.9800 . ?
C8 C9 1.497(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.440(5) . ?
C9 C18 1.498(5) . ?
C10 C11 1.184(5) . ?
C11 C12 1.430(5) . ?
C12 C13 1.378(5) . ?
C12 C17 1.387(5) . ?
C13 C14 1.372(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.354(6) . ?
C14 H14A 0.9300 . ?
C15 C16 1.351(6) . ?
C15 H15A 0.9300 . ?
C16 C17 1.371(5) . ?
C16 H16A 0.9300 . ?
C17 H17A 0.9300 . ?
C18 C19 1.481(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
C2 C1 C6 121.7(4) . . ?
C2 C1 H1A 119.1 . . ?
C6 C1 H1A 119.1 . . ?
C1 C2 C3 120.6(4) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C4 C3 C2 118.8(4) . . ?
C4 C3 Br1 120.6(3) . . ?
C2 C3 Br1 120.5(4) . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 121.2(4) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C1 C6 C5 116.7(4) . . ?
C1 C6 C7 118.9(3) . . ?
C5 C6 C7 124.3(4) . . ?
C8 C7 C6 125.3(3) . . ?
C8 C7 C9 59.3(3) . . ?
C6 C7 C9 121.8(3) . . ?
C8 C7 H7A 113.3 . . ?
C6 C7 H7A 113.3 . . ?
C9 C7 H7A 113.3 . . ?
C7 C8 C9 63.3(2) . . ?
C7 C8 H8A 117.4 . . ?
C9 C8 H8A 117.4 . . ?
C7 C8 H8B 117.4 . . ?
C9 C8 H8B 117.4 . . ?
H8A C8 H8B 114.5 . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 C18 117.4(3) . . ?
C8 C9 C18 116.6(3) . . ?
C10 C9 C7 120.0(3) . . ?
C8 C9 C7 57.4(2) . . ?
C18 C9 C7 112.9(3) . . ?
C11 C10 C9 177.9(4) . . ?
C10 C11 C12 177.8(5) . . ?
C13 C12 C17 117.0(4) . . ?
C13 C12 C11 121.0(4) . . ?
C17 C12 C11 121.9(4) . . ?
C14 C13 C12 121.3(4) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C17 120.1(4) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C16 C17 C12 121.1(4) . . ?
C16 C17 H17A 119.4 . . ?
C12 C17 H17A 119.4 . . ?
O1 C18 C19 121.4(4) . . ?
O1 C18 C9 120.7(4) . . ?
C19 C18 C9 117.8(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
C6 C1 C2 C3 -1.2(6) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C1 C2 C3 Br1 -177.7(3) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
Br1 C3 C4 C5 178.9(3) . . . . ?
C3 C4 C5 C6 -1.4(6) . . . . ?
C2 C1 C6 C5 0.6(5) . . . . ?
C2 C1 C6 C7 -178.3(3) . . . . ?
C4 C5 C6 C1 0.7(6) . . . . ?
C4 C5 C6 C7 179.4(4) . . . . ?
C1 C6 C7 C8 -163.3(4) . . . . ?
C5 C6 C7 C8 17.9(6) . . . . ?
C1 C6 C7 C9 124.0(4) . . . . ?
C5 C6 C7 C9 -54.7(5) . . . . ?
C6 C7 C8 C9 -109.2(4) . . . . ?
C7 C8 C9 C10 109.0(4) . . . . ?
C7 C8 C9 C18 -101.3(4) . . . . ?
C8 C7 C9 C10 -107.0(4) . . . . ?
C6 C7 C9 C10 8.0(5) . . . . ?
C6 C7 C9 C8 115.0(4) . . . . ?
C8 C7 C9 C18 107.9(4) . . . . ?
C6 C7 C9 C18 -137.1(4) . . . . ?
C8 C9 C10 C11 7(13) . . . . ?
C18 C9 C10 C11 -143(12) . . . . ?
C7 C9 C10 C11 73(12) . . . . ?
C9 C10 C11 C12 30(21) . . . . ?
C10 C11 C12 C13 -132(11) . . . . ?
C10 C11 C12 C17 46(11) . . . . ?
C17 C12 C13 C14 -1.3(6) . . . . ?
C11 C12 C13 C14 177.5(4) . . . . ?
C12 C13 C14 C15 1.2(7) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
C14 C15 C16 C17 -0.5(7) . . . . ?
C15 C16 C17 C12 0.3(7) . . . . ?
C13 C12 C17 C16 0.5(6) . . . . ?
C11 C12 C17 C16 -178.3(4) . . . . ?
C10 C9 C18 O1 160.4(4) . . . . ?
C8 C9 C18 O1 10.2(6) . . . . ?
C7 C9 C18 O1 -53.6(5) . . . . ?
C10 C9 C18 C19 -22.6(5) . . . . ?
C8 C9 C18 C19 -172.8(3) . . . . ?
C7 C9 C18 C19 123.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.042