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


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_name                'Dilip Kumar Maiti'
_publ_contact_author_name        'Dilip Kumar Maiti'
_publ_contact_author_email       maitidk@yahoo.com

data_pp494_0m
_database_code_depnum_ccdc_archive 'CCDC 799249'
#TrackingRef '- CIF CCDC 799249.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 Br O'
_chemical_formula_weight         213.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   12.286(8)
_cell_length_b                   4.978(3)
_cell_length_c                   14.499(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.853(8)
_cell_angle_gamma                90.00
_cell_volume                     848.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      24.61

_exptl_crystal_description       cubic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424.0
_exptl_absorpt_coefficient_mu    4.780
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_T_max  0.866
_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  'Bruker Kappa Apex 2'
_diffrn_measurement_method       FastFourierTransform
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5232
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         24.61
_reflns_number_total             1420
_reflns_number_gt                1077
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex CCD, Bruker Smart'
_computing_cell_refinement       'Apex CCD, Bruker Smart'
_computing_data_reduction        'Apex CCD, Bruker Smart'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)
_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^)+(0.1000P)^2^+0.0000P] 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_number_reflns         1420
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.1183
_refine_ls_wR_factor_gt          0.1006
_refine_ls_goodness_of_fit_ref   0.812
_refine_ls_restrained_S_all      0.812
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.65980(4) -0.41506(9) 0.95962(3) 0.0615(3) Uani 1 1 d . . .
C2 C 0.3431(4) 0.3870(9) 0.6399(4) 0.0581(13) Uani 1 1 d . . .
H3 H 0.2856 0.5113 0.6149 0.070 Uiso 1 1 calc R . .
C3 C 0.3556(3) 0.2765(9) 0.7302(3) 0.0472(10) Uani 1 1 d . . .
H4 H 0.3073 0.3265 0.7662 0.057 Uiso 1 1 calc R . .
C4 C 0.4408(3) 0.0916(8) 0.7656(3) 0.0387(9) Uani 1 1 d . . .
C5 C 0.5125(3) 0.0151(8) 0.7115(3) 0.0376(9) Uani 1 1 d . . .
C7 C 0.5986(3) -0.1879(8) 0.7665(3) 0.0387(9) Uani 1 1 d . . .
H8 H 0.5705 -0.3705 0.7489 0.046 Uiso 1 1 calc R . .
C8 C 0.5974(3) -0.1253(8) 0.8685(3) 0.0399(9) Uani 1 1 d . . .
H7 H 0.6448 0.0342 0.8899 0.048 Uiso 1 1 calc R . .
C9 C 0.4754(3) -0.0493(9) 0.8613(3) 0.0458(10) Uani 1 1 d . . .
H6 H 0.4289 -0.2068 0.8612 0.055 Uiso 1 1 calc R . .
H5 H 0.4716 0.0696 0.9132 0.055 Uiso 1 1 calc R . .
C1 C 0.4150(4) 0.3142(11) 0.5868(3) 0.0593(12) Uani 1 1 d . . .
H2 H 0.4060 0.3918 0.5267 0.071 Uiso 1 1 calc R . .
C6 C 0.5011(4) 0.1263(9) 0.6217(3) 0.0507(11) Uani 1 1 d . . .
H1 H 0.5495 0.0769 0.5858 0.061 Uiso 1 1 calc R . .
O1 O 0.7055(2) -0.1543(6) 0.7503(3) 0.0601(9) Uani 1 1 d . . .
H9 H 0.7332 -0.3020 0.7460 0.090 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 0.0785(4) 0.0378(3) 0.0564(4) -0.0013(2) 0.0009(3) 0.0118(2)
C2 0.039(2) 0.054(3) 0.072(3) 0.008(3) 0.001(2) 0.0013(19)
C3 0.038(2) 0.039(3) 0.063(3) 0.000(2) 0.014(2) 0.0039(18)
C4 0.0317(19) 0.038(2) 0.044(2) -0.0019(18) 0.0084(18) -0.0039(16)
C5 0.040(2) 0.030(2) 0.043(2) -0.0048(18) 0.0117(19) -0.0039(16)
C7 0.0331(19) 0.029(2) 0.058(3) -0.0052(18) 0.0189(18) -0.0064(16)
C8 0.041(2) 0.024(2) 0.050(3) -0.0044(17) 0.0056(19) -0.0003(15)
C9 0.051(2) 0.040(3) 0.051(3) 0.000(2) 0.022(2) 0.0051(19)
C1 0.067(3) 0.056(3) 0.046(3) 0.008(2) 0.004(2) -0.008(3)
C6 0.061(3) 0.046(3) 0.049(3) -0.008(2) 0.020(2) -0.009(2)
O1 0.0485(17) 0.0326(16) 0.113(3) 0.0077(18) 0.0449(19) 0.0029(13)

_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 C8 1.957(4) . ?
C2 C1 1.378(7) . ?
C2 C3 1.388(7) . ?
C2 H3 0.9300 . ?
C3 C4 1.377(6) . ?
C3 H4 0.9300 . ?
C4 C5 1.392(6) . ?
C4 C9 1.501(6) . ?
C5 C6 1.383(6) . ?
C5 C7 1.512(6) . ?
C7 O1 1.409(4) . ?
C7 C8 1.515(6) . ?
C7 H8 0.9800 . ?
C8 C9 1.520(5) . ?
C8 H7 0.9800 . ?
C9 H6 0.9700 . ?
C9 H5 0.9700 . ?
C1 C6 1.393(6) . ?
C1 H2 0.9300 . ?
C6 H1 0.9300 . ?
O1 H9 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
C1 C2 C3 120.6(4) . . ?
C1 C2 H3 119.7 . . ?
C3 C2 H3 119.7 . . ?
C4 C3 C2 118.8(4) . . ?
C4 C3 H4 120.6 . . ?
C2 C3 H4 120.6 . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 C9 129.6(4) . . ?
C5 C4 C9 109.7(3) . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 C7 128.9(4) . . ?
C4 C5 C7 110.2(4) . . ?
O1 C7 C5 112.1(3) . . ?
O1 C7 C8 114.3(3) . . ?
C5 C7 C8 100.0(3) . . ?
O1 C7 H8 110.0 . . ?
C5 C7 H8 110.0 . . ?
C8 C7 H8 110.0 . . ?
C7 C8 C9 105.8(3) . . ?
C7 C8 Br1 113.3(3) . . ?
C9 C8 Br1 114.5(3) . . ?
C7 C8 H7 107.6 . . ?
C9 C8 H7 107.6 . . ?
Br1 C8 H7 107.6 . . ?
C4 C9 C8 100.9(3) . . ?
C4 C9 H6 111.6 . . ?
C8 C9 H6 111.6 . . ?
C4 C9 H5 111.6 . . ?
C8 C9 H5 111.6 . . ?
H6 C9 H5 109.4 . . ?
C2 C1 C6 121.0(5) . . ?
C2 C1 H2 119.5 . . ?
C6 C1 H2 119.5 . . ?
C5 C6 C1 118.1(4) . . ?
C5 C6 H1 121.0 . . ?
C1 C6 H1 121.0 . . ?
C7 O1 H9 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.61
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.072