# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1486177'
_audit_update_record             
;
2016-08-18 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            AA132
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H18 Br2'
_chemical_formula_iupac          ?
_chemical_formula_weight         538.26

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9338(4)
_cell_length_b                   13.1529(7)
_cell_length_c                   13.7120(10)
_cell_angle_alpha                64.451(5)
_cell_angle_beta                 83.600(6)
_cell_angle_gamma                79.575(6)
_cell_volume                     1108.84(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      26.36
_cell_measurement_temperature    298.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536

_exptl_absorpt_coefficient_mu    3.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.61

_exptl_special_details           
;
;

_diffrn_ambient_temperature      298.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω

_diffrn_detector_area_resol_mean 10.000

_diffrn_reflns_number            9899
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17

_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.
;

_reflns_number_total             4518
_reflns_number_gt                3519
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1024
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_restrained_S_all      0.946
_refine_ls_number_reflns         4518
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0611P)²+0.1344P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.456
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0066(12)

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'

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

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br2 1.22689(4) -0.05411(2) 0.59906(2) 0.05692(13) Uani d . 1 . .
Br Br1 -0.62077(5) 0.35747(3) 1.10166(3) 0.07202(15) Uani d . 1 . .
C C27 0.8426(4) -0.07550(19) 0.6961(2) 0.0462(6) Uani d . 1 . .
H H27 0.8667 -0.1481 0.6978 0.055 Uiso calc R 1 . .
C C26 0.6634(4) -0.03689(19) 0.7344(2) 0.0449(6) Uani d . 1 . .
H H26 0.5682 -0.0847 0.7626 0.054 Uiso calc R 1 . .
C C21 -0.3961(4) 0.3266(2) 0.9275(2) 0.0537(7) Uani d . 1 . .
H H21 -0.508 0.3646 0.888 0.064 Uiso calc R 1 . .
C C29 0.9503(4) 0.1031(2) 0.6535(2) 0.0493(6) Uani d . 1 . .
H H29 1.0475 0.1497 0.6275 0.059 Uiso calc R 1 . .
C C28 0.9834(4) -0.0050(2) 0.6557(2) 0.0421(6) Uani d . 1 . .
C C25 0.6240(3) 0.07183(19) 0.7315(2) 0.0410(6) Uani d . 1 . .
C C12 0.3345(3) 0.22623(19) 0.7203(2) 0.0400(5) Uani d . 1 . .
C C13 0.3510(3) 0.29274(19) 0.6025(2) 0.0389(5) Uani d . 1 . .
C C18 0.2794(3) 0.41081(19) 0.5563(2) 0.0448(6) Uani d . 1 . .
C C11 0.4367(3) 0.11392(19) 0.7753(2) 0.0423(6) Uani d . 1 . .
C C10 0.3700(4) 0.0467(2) 0.8777(2) 0.0544(7) Uani d . 1 . .
H H10 0.4349 -0.0269 0.9143 0.065 Uiso calc R 1 . .
C C9 0.2085(4) 0.0865(2) 0.9270(2) 0.0569(7) Uani d . 1 . .
H H9 0.1575 0.0364 0.9922 0.068 Uiso calc R 1 . .
C C8 0.1210(4) 0.1988(2) 0.8817(2) 0.0470(6) Uani d . 1 . .
C C19 -0.0588(4) 0.2353(2) 0.9357(2) 0.0474(6) Uani d . 1 . .
C C20 -0.2283(4) 0.2913(2) 0.8791(2) 0.0502(6) Uani d . 1 . .
H H20 -0.2289 0.3056 0.8065 0.06 Uiso calc R 1 . .
C C22 -0.3949(4) 0.3045(2) 1.0350(2) 0.0485(6) Uani d . 1 . .
C C30 0.7726(4) 0.1400(2) 0.6901(2) 0.0483(6) Uani d . 1 . .
H H30 0.7495 0.213 0.6874 0.058 Uiso calc R 1 . .
C C14 0.4108(4) 0.2395(2) 0.5319(2) 0.0449(6) Uani d . 1 . .
H H14 0.4555 0.1616 0.5609 0.054 Uiso calc R 1 . .
C C15 0.4051(4) 0.2997(2) 0.4212(2) 0.0530(7) Uani d . 1 . .
H H15 0.4435 0.2621 0.3767 0.064 Uiso calc R 1 . .
C C16 0.3422(4) 0.4160(3) 0.3763(2) 0.0607(8) Uani d . 1 . .
H H16 0.3425 0.4573 0.3015 0.073 Uiso calc R 1 . .
C C17 0.2793(4) 0.4697(2) 0.4431(2) 0.0577(8) Uani d . 1 . .
H H17 0.2352 0.5477 0.4123 0.069 Uiso calc R 1 . .
C C1 0.2039(3) 0.4657(2) 0.6277(2) 0.0470(6) Uani d . 1 . .
C C2 0.1817(4) 0.5851(2) 0.5897(3) 0.0663(9) Uani d . 1 . .
H H2 0.211 0.6295 0.5174 0.08 Uiso calc R 1 . .
C C5 0.0982(4) 0.4544(3) 0.8056(3) 0.0575(7) Uani d . 1 . .
H H5 0.0712 0.4114 0.8786 0.069 Uiso calc R 1 . .
C C6 0.1575(3) 0.3993(2) 0.7369(2) 0.0461(6) Uani d . 1 . .
C C7 0.1985(3) 0.2733(2) 0.7798(2) 0.0418(6) Uani d . 1 . .
C C23 -0.2310(4) 0.2466(3) 1.0946(2) 0.0602(8) Uani d . 1 . .
H H23 -0.2322 0.2308 1.1676 0.072 Uiso calc R 1 . .
C C24 -0.0646(4) 0.2121(3) 1.0444(2) 0.0604(8) Uani d . 1 . .
H H24 0.0459 0.1724 1.0846 0.072 Uiso calc R 1 . .
C C4 0.0793(4) 0.5719(3) 0.7659(4) 0.0748(11) Uani d . 1 . .
H H4 0.0408 0.6072 0.8124 0.09 Uiso calc R 1 . .
C C3 0.1173(5) 0.6367(3) 0.6580(4) 0.0796(12) Uani d . 1 . .
H H3 0.0993 0.7157 0.6312 0.096 Uiso calc R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br2 C28 . 1.902(2) ?
Br1 C22 . 1.900(3) ?
C27 C28 . 1.373(4) ?
C27 C26 . 1.391(3) ?
C27 H27 . 0.93 ?
C26 C25 . 1.390(3) ?
C26 H26 . 0.93 ?
C21 C22 . 1.375(4) ?
C21 C20 . 1.381(4) ?
C21 H21 . 0.93 ?
C29 C30 . 1.364(4) ?
C29 C28 . 1.386(3) ?
C29 H29 . 0.93 ?
C25 C30 . 1.397(4) ?
C25 C11 . 1.485(3) ?
C12 C7 . 1.411(3) ?
C12 C11 . 1.426(3) ?
C12 C13 . 1.472(3) ?
C13 C14 . 1.409(4) ?
C13 C18 . 1.415(3) ?
C18 C17 . 1.405(4) ?
C18 C1 . 1.453(4) ?
C11 C10 . 1.378(4) ?
C10 C9 . 1.382(4) ?
C10 H10 . 0.93 ?
C9 C8 . 1.380(4) ?
C9 H9 . 0.93 ?
C8 C7 . 1.429(4) ?
C8 C19 . 1.490(4) ?
C19 C20 . 1.387(4) ?
C19 C24 . 1.383(4) ?
C20 H20 . 0.93 ?
C22 C23 . 1.377(4) ?
C30 H30 . 0.93 ?
C14 C15 . 1.378(4) ?
C14 H14 . 0.93 ?
C15 C16 . 1.384(4) ?
C15 H15 . 0.93 ?
C16 C17 . 1.374(5) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?
C1 C6 . 1.405(4) ?
C1 C2 . 1.409(3) ?
C2 C3 . 1.372(5) ?
C2 H2 . 0.93 ?
C5 C4 . 1.386(4) ?
C5 C6 . 1.406(4) ?
C5 H5 . 0.93 ?
C6 C7 . 1.482(3) ?
C23 C24 . 1.383(4) ?
C23 H23 . 0.93 ?
C24 H24 . 0.93 ?
C4 C3 . 1.376(5) ?
C4 H4 . 0.93 ?
C3 H3 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C28 C27 C26 . . 119.1(2) ?
C28 C27 H27 . . 120.4 ?
C26 C27 H27 . . 120.4 ?
C25 C26 C27 . . 121.2(2) ?
C25 C26 H26 . . 119.4 ?
C27 C26 H26 . . 119.4 ?
C22 C21 C20 . . 118.9(3) ?
C22 C21 H21 . . 120.6 ?
C20 C21 H21 . . 120.6 ?
C30 C29 C28 . . 118.9(2) ?
C30 C29 H29 . . 120.6 ?
C28 C29 H29 . . 120.6 ?
C27 C28 C29 . . 121.1(2) ?
C27 C28 Br2 . . 119.95(18) ?
C29 C28 Br2 . . 118.95(19) ?
C26 C25 C30 . . 117.4(2) ?
C26 C25 C11 . . 122.4(2) ?
C30 C25 C11 . . 120.1(2) ?
C7 C12 C11 . . 118.8(2) ?
C7 C12 C13 . . 117.7(2) ?
C11 C12 C13 . . 123.3(2) ?
C14 C13 C18 . . 117.9(2) ?
C14 C13 C12 . . 121.6(2) ?
C18 C13 C12 . . 119.9(2) ?
C17 C18 C13 . . 118.6(3) ?
C17 C18 C1 . . 122.6(2) ?
C13 C18 C1 . . 118.8(2) ?
C10 C11 C12 . . 118.5(2) ?
C10 C11 C25 . . 118.9(2) ?
C12 C11 C25 . . 122.3(2) ?
C9 C10 C11 . . 121.3(2) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C8 C9 C10 . . 121.5(3) ?
C8 C9 H9 . . 119.2 ?
C10 C9 H9 . . 119.2 ?
C9 C8 C7 . . 118.2(2) ?
C9 C8 C19 . . 119.1(2) ?
C7 C8 C19 . . 122.6(2) ?
C20 C19 C24 . . 117.6(2) ?
C20 C19 C8 . . 120.9(2) ?
C24 C19 C8 . . 121.4(2) ?
C21 C20 C19 . . 121.9(3) ?
C21 C20 H20 . . 119.1 ?
C19 C20 H20 . . 119.1 ?
C21 C22 C23 . . 121.0(2) ?
C21 C22 Br1 . . 119.6(2) ?
C23 C22 Br1 . . 119.5(2) ?
C29 C30 C25 . . 122.3(2) ?
C29 C30 H30 . . 118.9 ?
C25 C30 H30 . . 118.9 ?
C15 C14 C13 . . 121.8(2) ?
C15 C14 H14 . . 119.1 ?
C13 C14 H14 . . 119.1 ?
C14 C15 C16 . . 120.1(3) ?
C14 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C17 C16 C15 . . 119.4(3) ?
C17 C16 H16 . . 120.3 ?
C15 C16 H16 . . 120.3 ?
C16 C17 C18 . . 122.2(3) ?
C16 C17 H17 . . 118.9 ?
C18 C17 H17 . . 118.9 ?
C6 C1 C2 . . 119.2(3) ?
C6 C1 C18 . . 119.9(2) ?
C2 C1 C18 . . 120.9(3) ?
C3 C2 C1 . . 120.9(3) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C4 C5 C6 . . 120.8(3) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C1 . . 118.5(2) ?
C5 C6 C7 . . 121.5(3) ?
C1 C6 C7 . . 119.4(2) ?
C12 C7 C8 . . 119.0(2) ?
C12 C7 C6 . . 117.4(2) ?
C8 C7 C6 . . 123.4(2) ?
C24 C23 C22 . . 119.1(3) ?
C24 C23 H23 . . 120.4 ?
C22 C23 H23 . . 120.4 ?
C23 C24 C19 . . 121.5(3) ?
C23 C24 H24 . . 119.2 ?
C19 C24 H24 . . 119.2 ?
C3 C4 C5 . . 120.2(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C4 C3 C2 . . 120.2(3) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C28 C27 C26 C25 . . . . 0.7(4) ?
C26 C27 C28 C29 . . . . 0.6(4) ?
C26 C27 C28 Br2 . . . . -178.2(2) ?
C30 C29 C28 C27 . . . . -1.4(4) ?
C30 C29 C28 Br2 . . . . 177.4(2) ?
C27 C26 C25 C30 . . . . -1.0(4) ?
C27 C26 C25 C11 . . . . -177.8(2) ?
C7 C12 C13 C14 . . . . -152.3(2) ?
C11 C12 C13 C14 . . . . 22.5(4) ?
C7 C12 C13 C18 . . . . 18.4(3) ?
C11 C12 C13 C18 . . . . -166.7(2) ?
C14 C13 C18 C17 . . . . -2.6(3) ?
C12 C13 C18 C17 . . . . -173.7(2) ?
C14 C13 C18 C1 . . . . 175.6(2) ?
C12 C13 C18 C1 . . . . 4.6(3) ?
C7 C12 C11 C10 . . . . 13.8(4) ?
C13 C12 C11 C10 . . . . -161.0(3) ?
C7 C12 C11 C25 . . . . -159.3(2) ?
C13 C12 C11 C25 . . . . 25.9(4) ?
C26 C25 C11 C10 . . . . 49.1(4) ?
C30 C25 C11 C10 . . . . -127.6(3) ?
C26 C25 C11 C12 . . . . -137.8(3) ?
C30 C25 C11 C12 . . . . 45.5(4) ?
C12 C11 C10 C9 . . . . -0.3(4) ?
C25 C11 C10 C9 . . . . 173.0(3) ?
C11 C10 C9 C8 . . . . -7.6(5) ?
C10 C9 C8 C7 . . . . 1.8(5) ?
C10 C9 C8 C19 . . . . 176.9(3) ?
C9 C8 C19 C20 . . . . -126.5(3) ?
C7 C8 C19 C20 . . . . 48.4(4) ?
C9 C8 C19 C24 . . . . 51.9(4) ?
C7 C8 C19 C24 . . . . -133.3(3) ?
C22 C21 C20 C19 . . . . -0.5(4) ?
C24 C19 C20 C21 . . . . 2.1(4) ?
C8 C19 C20 C21 . . . . -179.6(3) ?
C20 C21 C22 C23 . . . . -1.1(4) ?
C20 C21 C22 Br1 . . . . 177.5(2) ?
C28 C29 C30 C25 . . . . 1.1(4) ?
C26 C25 C30 C29 . . . . 0.1(4) ?
C11 C25 C30 C29 . . . . 177.0(3) ?
C18 C13 C14 C15 . . . . 1.5(4) ?
C12 C13 C14 C15 . . . . 172.4(2) ?
C13 C14 C15 C16 . . . . 1.0(4) ?
C14 C15 C16 C17 . . . . -2.3(4) ?
C15 C16 C17 C18 . . . . 1.0(5) ?
C13 C18 C17 C16 . . . . 1.5(4) ?
C1 C18 C17 C16 . . . . -176.8(3) ?
C17 C18 C1 C6 . . . . 162.5(2) ?
C13 C18 C1 C6 . . . . -15.7(4) ?
C17 C18 C1 C2 . . . . -19.3(4) ?
C13 C18 C1 C2 . . . . 162.4(2) ?
C6 C1 C2 C3 . . . . 0.6(5) ?
C18 C1 C2 C3 . . . . -177.6(3) ?
C4 C5 C6 C1 . . . . 2.2(4) ?
C4 C5 C6 C7 . . . . 173.5(3) ?
C2 C1 C6 C5 . . . . -2.7(4) ?
C18 C1 C6 C5 . . . . 175.5(2) ?
C2 C1 C6 C7 . . . . -174.2(2) ?
C18 C1 C6 C7 . . . . 4.0(4) ?
C11 C12 C7 C8 . . . . -19.5(4) ?
C13 C12 C7 C8 . . . . 155.6(2) ?
C11 C12 C7 C6 . . . . 155.2(2) ?
C13 C12 C7 C6 . . . . -29.8(3) ?
C9 C8 C7 C12 . . . . 11.7(4) ?
C19 C8 C7 C12 . . . . -163.2(3) ?
C9 C8 C7 C6 . . . . -162.6(3) ?
C19 C8 C7 C6 . . . . 22.5(4) ?
C5 C6 C7 C12 . . . . -152.2(2) ?
C1 C6 C7 C12 . . . . 19.0(3) ?
C5 C6 C7 C8 . . . . 22.2(4) ?
C1 C6 C7 C8 . . . . -166.6(3) ?
C21 C22 C23 C24 . . . . 1.1(5) ?
Br1 C22 C23 C24 . . . . -177.5(2) ?
C22 C23 C24 C19 . . . . 0.5(5) ?
C20 C19 C24 C23 . . . . -2.1(5) ?
C8 C19 C24 C23 . . . . 179.6(3) ?
C6 C5 C4 C3 . . . . 0.5(5) ?
C5 C4 C3 C2 . . . . -2.6(5) ?
C1 C2 C3 C4 . . . . 2.1(5) ?

