# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_201out
_database_code_depnum_ccdc_archive 'CCDC 1407752'

_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1,3-dibromo-2-phenyl-1H-indene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 Br2'
_chemical_formula_sum            'C15 H10 Br2'
_chemical_formula_weight         350.05

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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'
'-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                   16.202(2)
_cell_length_b                   7.6187(11)
_cell_length_c                   20.676(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2552.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.97
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    6.325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3644
_exptl_absorpt_correction_T_max  0.3644
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      293(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 smart apex II CCD'
_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            28281
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2250
_reflns_number_gt                1563
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0314P)²+2.7210P] 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         2250
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0733
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002

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 0.60019(3) 0.17941(5) 0.490275(18) 0.05087(14) Uani 1 1 d . . .
Br2 Br 0.60152(3) 0.10577(6) 0.75823(2) 0.06678(16) Uani 1 1 d . . .
C1 C 0.4405(3) 0.0901(5) 0.6517(2) 0.0532(10) Uani 1 1 d . . .
H1 H 0.4687 -0.0019 0.6713 0.064 Uiso 1 1 calc R . .
C2 C 0.3557(3) 0.0860(6) 0.6486(2) 0.0619(12) Uani 1 1 d . . .
H2 H 0.3271 -0.0086 0.6660 0.074 Uiso 1 1 calc R . .
C15 C 0.6279(3) 0.1856(5) 0.67440(17) 0.0453(9) Uani 1 1 d . . .
C5 C 0.4403(3) 0.3640(5) 0.59555(19) 0.0523(10) Uani 1 1 d . . .
H5 H 0.4682 0.4575 0.5767 0.063 Uiso 1 1 calc R . .
C13 C 0.6264(2) 0.3019(5) 0.57180(17) 0.0426(9) Uani 1 1 d . . .
H13 H 0.6163 0.4279 0.5664 0.051 Uiso 1 1 calc R . .
C14 C 0.5751(2) 0.2339(5) 0.62777(17) 0.0411(9) Uani 1 1 d . . .
C6 C 0.4846(2) 0.2302(5) 0.62592(17) 0.0437(9) Uani 1 1 d . . .
C3 C 0.3131(3) 0.2211(7) 0.6198(2) 0.0651(12) Uani 1 1 d . . .
H3 H 0.2557 0.2187 0.6185 0.078 Uiso 1 1 calc R . .
C9 C 0.7139(3) 0.2065(5) 0.65531(18) 0.0452(9) Uani 1 1 d . . .
C4 C 0.3548(3) 0.3579(7) 0.5934(2) 0.0647(13) Uani 1 1 d . . .
H4 H 0.3258 0.4486 0.5737 0.078 Uiso 1 1 calc R . .
C11 C 0.7868(3) 0.3099(5) 0.5610(2) 0.0532(10) Uani 1 1 d . . .
H11 H 0.7867 0.3561 0.5194 0.064 Uiso 1 1 calc R . .
C10 C 0.7140(2) 0.2739(4) 0.59233(18) 0.0428(9) Uani 1 1 d . . .
C8 C 0.7868(3) 0.1743(5) 0.6870(2) 0.0605(11) Uani 1 1 d . . .
H8 H 0.7870 0.1298 0.7289 0.073 Uiso 1 1 calc R . .
C12 C 0.8606(3) 0.2758(6) 0.5929(3) 0.0623(12) Uani 1 1 d . . .
H12 H 0.9105 0.2976 0.5723 0.075 Uiso 1 1 calc R . .
C7 C 0.8600(3) 0.2098(6) 0.6549(3) 0.0651(13) Uani 1 1 d . . .
H7 H 0.9099 0.1886 0.6757 0.078 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 0.0599(2) 0.0562(3) 0.0365(2) -0.00024(17) -0.0046(2) 0.0007(2)
Br2 0.0848(3) 0.0809(3) 0.0346(2) 0.0067(2) 0.0020(2) 0.0018(3)
C1 0.059(3) 0.052(3) 0.049(3) -0.005(2) 0.006(2) -0.003(2)
C2 0.073(3) 0.065(3) 0.048(3) -0.008(2) 0.011(2) -0.015(3)
C15 0.064(3) 0.040(2) 0.032(2) -0.0032(16) 0.0008(19) 0.0016(19)
C5 0.059(3) 0.052(3) 0.046(2) 0.0015(19) 0.000(2) 0.005(2)
C13 0.057(2) 0.031(2) 0.040(2) 0.0001(16) 0.0015(18) 0.0003(17)
C14 0.053(2) 0.0302(19) 0.040(2) -0.0038(16) 0.0038(18) -0.0016(17)
C6 0.053(2) 0.044(2) 0.034(2) -0.0070(17) 0.0037(19) -0.0009(19)
C3 0.054(3) 0.082(4) 0.059(3) -0.019(3) 0.007(2) -0.005(3)
C9 0.059(3) 0.037(2) 0.040(2) -0.0065(16) -0.0063(19) 0.0003(19)
C4 0.060(3) 0.077(4) 0.058(3) -0.008(2) -0.004(2) 0.019(3)
C11 0.058(3) 0.044(2) 0.057(3) -0.0051(19) 0.004(2) -0.007(2)
C10 0.052(2) 0.0303(19) 0.046(2) -0.0060(16) -0.0040(19) -0.0050(17)
C8 0.073(3) 0.056(3) 0.053(3) -0.005(2) -0.014(2) 0.002(2)
C12 0.055(3) 0.050(3) 0.082(4) -0.014(2) 0.003(3) -0.003(2)
C7 0.054(3) 0.061(3) 0.081(4) -0.016(3) -0.018(3) 0.003(2)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C13 1.973(4) . ?
Br2 C15 1.886(4) . ?
C1 C2 1.376(6) . ?
C1 C6 1.391(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(6) . ?
C2 H2 0.9300 . ?
C15 C14 1.340(5) . ?
C15 C9 1.457(5) . ?
C5 C4 1.386(6) . ?
C5 C6 1.395(5) . ?
C5 H5 0.9300 . ?
C13 C10 1.496(5) . ?
C13 C14 1.516(5) . ?
C13 H13 0.9800 . ?
C14 C6 1.467(5) . ?
C3 C4 1.357(6) . ?
C3 H3 0.9300 . ?
C9 C8 1.373(5) . ?
C9 C10 1.400(5) . ?
C4 H4 0.9300 . ?
C11 C10 1.373(5) . ?
C11 C12 1.390(6) . ?
C11 H11 0.9300 . ?
C8 C7 1.385(6) . ?
C8 H8 0.9300 . ?
C12 C7 1.377(7) . ?
C12 H12 0.9300 . ?
C7 H7 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
C2 C1 C6 120.8(4) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 120.3(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C14 C15 C9 112.7(3) . . ?
C14 C15 Br2 127.3(3) . . ?
C9 C15 Br2 120.1(3) . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C10 C13 C14 104.7(3) . . ?
C10 C13 Br1 112.3(2) . . ?
C14 C13 Br1 111.9(2) . . ?
C10 C13 H13 109.3 . . ?
C14 C13 H13 109.3 . . ?
Br1 C13 H13 109.3 . . ?
C15 C14 C6 130.6(4) . . ?
C15 C14 C13 107.1(3) . . ?
C6 C14 C13 122.3(3) . . ?
C1 C6 C5 118.0(4) . . ?
C1 C6 C14 121.2(4) . . ?
C5 C6 C14 120.8(4) . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C8 C9 C10 120.6(4) . . ?
C8 C9 C15 132.4(4) . . ?
C10 C9 C15 107.0(3) . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C10 C11 C12 118.5(4) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 C13 130.7(4) . . ?
C9 C10 C13 108.4(3) . . ?
C9 C8 C7 118.3(4) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C7 C12 C11 120.3(4) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C7 C8 121.5(4) . . ?
C12 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?

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 0.0(6) . . . . ?
C9 C15 C14 C6 178.3(4) . . . . ?
Br2 C15 C14 C6 -3.9(6) . . . . ?
C9 C15 C14 C13 -2.5(4) . . . . ?
Br2 C15 C14 C13 175.3(3) . . . . ?
C10 C13 C14 C15 3.4(4) . . . . ?
Br1 C13 C14 C15 125.3(3) . . . . ?
C10 C13 C14 C6 -177.3(3) . . . . ?
Br1 C13 C14 C6 -55.4(4) . . . . ?
C2 C1 C6 C5 -1.5(6) . . . . ?
C2 C1 C6 C14 -178.7(4) . . . . ?
C4 C5 C6 C1 2.0(6) . . . . ?
C4 C5 C6 C14 179.2(4) . . . . ?
C15 C14 C6 C1 -40.1(6) . . . . ?
C13 C14 C6 C1 140.7(4) . . . . ?
C15 C14 C6 C5 142.8(4) . . . . ?
C13 C14 C6 C5 -36.4(5) . . . . ?
C1 C2 C3 C4 1.0(7) . . . . ?
C14 C15 C9 C8 179.9(4) . . . . ?
Br2 C15 C9 C8 2.0(6) . . . . ?
C14 C15 C9 C10 0.4(4) . . . . ?
Br2 C15 C9 C10 -177.5(2) . . . . ?
C2 C3 C4 C5 -0.5(7) . . . . ?
C6 C5 C4 C3 -1.1(7) . . . . ?
C12 C11 C10 C9 0.8(5) . . . . ?
C12 C11 C10 C13 177.6(4) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C15 C9 C10 C11 179.3(3) . . . . ?
C8 C9 C10 C13 -177.7(3) . . . . ?
C15 C9 C10 C13 1.9(4) . . . . ?
C14 C13 C10 C11 179.7(4) . . . . ?
Br1 C13 C10 C11 58.1(5) . . . . ?
C14 C13 C10 C9 -3.2(4) . . . . ?
Br1 C13 C10 C9 -124.8(3) . . . . ?
C10 C9 C8 C7 -0.2(6) . . . . ?
C15 C9 C8 C7 -179.6(4) . . . . ?
C10 C11 C12 C7 -0.9(6) . . . . ?
C11 C12 C7 C8 0.5(7) . . . . ?
C9 C8 C7 C12 0.0(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.067

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
