# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_a00101
_database_code_depnum_ccdc_archive 'CCDC 1484867'
_audit_update_record             
;
2016-06-12 deposited with the CCDC.
2016-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.19 H2.19 Br0.13'
_chemical_formula_weight         38.87

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.167(11)
_cell_length_b                   10.880(11)
_cell_length_c                   14.496(15)
_cell_angle_alpha                73.632(13)
_cell_angle_beta                 79.944(12)
_cell_angle_gamma                89.367(13)
_cell_volume                     1514(3)
_cell_formula_units_Z            31
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8802
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      23.17

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.697
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33585
_diffrn_reflns_av_unetI/netI     0.1186
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.488
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5944
_reflns_number_gt                3926
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.1504P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5944
_refine_ls_number_parameters     331
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.095
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.99864(4) 0.43702(4) 0.21693(3) 0.07519(19) Uani 1 1 d . . . . .
Br2 Br 0.73798(7) 0.82930(6) -0.44460(3) 0.1114(2) Uani 1 1 d . . . . .
C1 C 0.5653(3) 0.7220(3) 0.0006(2) 0.0432(7) Uani 1 1 d . . . . .
C2 C 0.6058(3) 0.7504(3) -0.1077(2) 0.0448(7) Uani 1 1 d . . . . .
C3 C 0.8032(3) 0.6832(4) 0.0187(2) 0.0517(8) Uani 1 1 d . . . . .
H3 H 0.8281 0.7459 -0.0406 0.062 Uiso 1 1 calc R U . . .
C4 C 0.9017(3) 0.6211(4) 0.0668(3) 0.0557(9) Uani 1 1 d . . . . .
H4 H 0.9915 0.6428 0.0412 0.067 Uiso 1 1 calc R U . . .
C5 C 0.1774(3) 0.9437(3) -0.1502(2) 0.0471(8) Uani 1 1 d . . . . .
C6 C 0.2181(3) 0.9987(4) -0.0834(2) 0.0525(8) Uani 1 1 d . . . . .
H6 H 0.1892 1.0795 -0.0815 0.063 Uiso 1 1 calc R U . . .
C7 C 0.4455(3) 0.7582(3) 0.0414(2) 0.0438(7) Uani 1 1 d . . . . .
C8 C 0.8646(3) 0.5274(3) 0.1528(2) 0.0507(8) Uani 1 1 d . . . . .
C9 C 0.6679(3) 0.6548(3) 0.0562(2) 0.0420(7) Uani 1 1 d . . . . .
C10 C 0.6344(3) 0.5576(3) 0.1438(2) 0.0463(7) Uani 1 1 d . . . . .
H10 H 0.5448 0.5351 0.1698 0.056 Uiso 1 1 calc R U . . .
C11 C 0.2999(3) 0.9366(3) -0.0200(2) 0.0514(8) Uani 1 1 d . . . . .
H11 H 0.3240 0.9758 0.0243 0.062 Uiso 1 1 calc R U . . .
C12 C 0.4021(3) 0.7423(3) 0.1477(2) 0.0435(7) Uani 1 1 d . . . . .
C13 C 0.6093(3) 0.8725(4) -0.1692(2) 0.0531(8) Uani 1 1 d . . . . .
H13 H 0.5851 0.9400 -0.1430 0.064 Uiso 1 1 calc R U . . .
C14 C 0.4794(3) 0.7815(4) 0.2046(2) 0.0506(8) Uani 1 1 d . . . . .
H14 H 0.5621 0.8229 0.1755 0.061 Uiso 1 1 calc R U . . .
C15 C 0.0945(3) 1.0191(4) -0.2243(3) 0.0564(9) Uani 1 1 d . . . . .
C16 C 0.2778(3) 0.6853(4) 0.1943(2) 0.0523(8) Uani 1 1 d . . . . .
H16 H 0.2217 0.6608 0.1578 0.063 Uiso 1 1 calc R U . . .
C17 C 0.3467(3) 0.8179(3) -0.0209(2) 0.0428(7) Uani 1 1 d . . . . .
C18 C 0.7313(3) 0.4944(3) 0.1925(2) 0.0487(8) Uani 1 1 d . . . . .
H18 H 0.7076 0.4304 0.2512 0.058 Uiso 1 1 calc R U . . .
C19 C 0.6449(3) 0.6517(3) -0.1486(2) 0.0511(8) Uani 1 1 d . . . . .
H19 H 0.6461 0.5688 -0.1079 0.061 Uiso 1 1 calc R U . . .
C20 C 0.2171(3) 0.8221(4) -0.1454(3) 0.0587(9) Uani 1 1 d . . . . .
H20 H 0.1872 0.7798 -0.1858 0.070 Uiso 1 1 calc R U . . .
C21 C 0.3005(3) 0.7593(4) -0.0823(3) 0.0556(9) Uani 1 1 d . . . . .
H21 H 0.3255 0.6767 -0.0816 0.067 Uiso 1 1 calc R U . . .
C22 C 0.6829(4) 0.7960(4) -0.3072(3) 0.0623(10) Uani 1 1 d . . . . .
C23 C 0.2352(3) 0.6641(4) 0.2932(3) 0.0596(9) Uani 1 1 d . . . . .
H23 H 0.1517 0.6241 0.3218 0.072 Uiso 1 1 calc R U . . .
C24 C 0.6820(3) 0.6742(4) -0.2487(3) 0.0593(9) Uani 1 1 d . . . . .
H24 H 0.7058 0.6069 -0.2753 0.071 Uiso 1 1 calc R U . . .
C25 C 0.3130(4) 0.7005(4) 0.3514(3) 0.0556(9) Uani 1 1 d . . . . .
C26 C 0.4363(3) 0.7604(4) 0.3038(3) 0.0583(9) Uani 1 1 d . . . . .
H26 H 0.4915 0.7871 0.3399 0.070 Uiso 1 1 calc R U . . .
C27 C 0.6483(4) 0.8976(4) -0.2697(3) 0.0655(10) Uani 1 1 d . . . . .
H27 H 0.6510 0.9808 -0.3106 0.079 Uiso 1 1 calc R U . . .
C28 C 0.2639(4) 0.6734(5) 0.4608(3) 0.0743(12) Uani 1 1 d . . . . .
C29 C -0.0390(5) 1.0445(7) -0.1723(4) 0.133(3) Uani 1 1 d . U . . .
H29A H -0.0279 1.1055 -0.1374 0.200 Uiso 1 1 calc R U . . .
H29B H -0.0787 0.9660 -0.1271 0.200 Uiso 1 1 calc R U . . .
H29C H -0.0960 1.0782 -0.2190 0.200 Uiso 1 1 calc R U . . .
C30 C 0.0674(8) 0.9468(7) -0.2950(5) 0.141(3) Uani 1 1 d . U . . .
H30A H 0.0136 0.9971 -0.3388 0.211 Uiso 1 1 calc R U . . .
H30B H 0.0208 0.8667 -0.2591 0.211 Uiso 1 1 calc R U . . .
H30C H 0.1507 0.9308 -0.3317 0.211 Uiso 1 1 calc R U . . .
C31 C 0.1331(7) 0.7435(8) 0.4780(4) 0.152(3) Uani 1 1 d . U . . .
H31A H 0.0612 0.6992 0.4641 0.228 Uiso 1 1 calc R U . . .
H31B H 0.1433 0.8297 0.4357 0.228 Uiso 1 1 calc R U . . .
H31C H 0.1136 0.7452 0.5448 0.228 Uiso 1 1 calc R U . . .
C32 C 0.3589(8) 0.7340(7) 0.5098(4) 0.145(3) Uani 1 1 d . U . . .
H32A H 0.3216 0.7196 0.5777 0.217 Uiso 1 1 calc R U . . .
H32B H 0.3699 0.8245 0.4784 0.217 Uiso 1 1 calc R U . . .
H32C H 0.4443 0.6957 0.5037 0.217 Uiso 1 1 calc R U . . .
C33 C 0.1707(6) 1.1394(7) -0.2860(5) 0.140(3) Uani 1 1 d . U . . .
H33A H 0.2553 1.1182 -0.3178 0.210 Uiso 1 1 calc R U . . .
H33B H 0.1853 1.1923 -0.2455 0.210 Uiso 1 1 calc R U . . .
H33C H 0.1205 1.1849 -0.3344 0.210 Uiso 1 1 calc R U . . .
C34 C 0.2487(9) 0.5357(6) 0.5086(4) 0.171(4) Uani 1 1 d . U . . .
H34A H 0.2063 0.4948 0.4701 0.256 Uiso 1 1 calc R U . . .
H34B H 0.1946 0.5206 0.5723 0.256 Uiso 1 1 calc R U . . .
H34C H 0.3350 0.5012 0.5147 0.256 Uiso 1 1 calc R U . . .


_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 1.894(3) . ?
Br2 C22 1.902(4) . ?
C1 C7 1.364(4) . ?
C1 C9 1.489(4) . ?
C1 C2 1.493(5) . ?
C2 C13 1.373(5) . ?
C2 C19 1.389(5) . ?
C3 C4 1.382(4) . ?
C3 C9 1.392(4) . ?
C4 C8 1.365(5) . ?
C5 C20 1.366(5) . ?
C5 C6 1.393(5) . ?
C5 C15 1.531(4) . ?
C6 C11 1.377(4) . ?
C7 C12 1.487(5) . ?
C7 C17 1.489(4) . ?
C8 C18 1.385(5) . ?
C9 C10 1.395(5) . ?
C10 C18 1.377(4) . ?
C11 C17 1.375(5) . ?
C12 C14 1.383(4) . ?
C12 C16 1.386(5) . ?
C13 C27 1.389(5) . ?
C14 C26 1.381(5) . ?
C15 C33 1.495(7) . ?
C15 C29 1.496(6) . ?
C15 C30 1.516(6) . ?
C16 C23 1.376(5) . ?
C17 C21 1.375(4) . ?
C19 C24 1.385(5) . ?
C20 C21 1.388(5) . ?
C22 C24 1.357(6) . ?
C22 C27 1.381(6) . ?
C23 C25 1.387(5) . ?
C25 C26 1.391(5) . ?
C25 C28 1.522(5) . ?
C28 C34 1.460(8) . ?
C28 C31 1.543(7) . ?
C28 C32 1.546(8) . ?

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
C7 C1 C9 124.9(3) . . ?
C7 C1 C2 121.3(3) . . ?
C9 C1 C2 113.8(3) . . ?
C13 C2 C19 118.0(3) . . ?
C13 C2 C1 122.1(3) . . ?
C19 C2 C1 119.8(3) . . ?
C4 C3 C9 122.0(3) . . ?
C8 C4 C3 118.8(3) . . ?
C20 C5 C6 116.1(3) . . ?
C20 C5 C15 123.5(3) . . ?
C6 C5 C15 120.4(3) . . ?
C11 C6 C5 121.7(3) . . ?
C1 C7 C12 124.5(3) . . ?
C1 C7 C17 120.4(3) . . ?
C12 C7 C17 115.0(3) . . ?
C4 C8 C18 121.5(3) . . ?
C4 C8 Br1 119.2(3) . . ?
C18 C8 Br1 119.4(3) . . ?
C3 C9 C10 117.4(3) . . ?
C3 C9 C1 120.1(3) . . ?
C10 C9 C1 122.4(3) . . ?
C18 C10 C9 121.4(3) . . ?
C17 C11 C6 121.3(3) . . ?
C14 C12 C16 116.8(3) . . ?
C14 C12 C7 123.7(3) . . ?
C16 C12 C7 119.6(3) . . ?
C2 C13 C27 121.5(3) . . ?
C26 C14 C12 121.3(3) . . ?
C33 C15 C29 112.6(5) . . ?
C33 C15 C30 105.7(5) . . ?
C29 C15 C30 106.6(5) . . ?
C33 C15 C5 109.4(3) . . ?
C29 C15 C5 109.9(3) . . ?
C30 C15 C5 112.7(3) . . ?
C23 C16 C12 121.8(3) . . ?
C11 C17 C21 117.3(3) . . ?
C11 C17 C7 120.3(3) . . ?
C21 C17 C7 122.3(3) . . ?
C10 C18 C8 119.1(3) . . ?
C24 C19 C2 121.5(3) . . ?
C5 C20 C21 122.3(3) . . ?
C17 C21 C20 120.9(3) . . ?
C24 C22 C27 121.8(3) . . ?
C24 C22 Br2 119.4(3) . . ?
C27 C22 Br2 118.8(3) . . ?
C16 C23 C25 122.0(3) . . ?
C22 C24 C19 118.8(3) . . ?
C23 C25 C26 116.0(3) . . ?
C23 C25 C28 120.6(4) . . ?
C26 C25 C28 123.4(3) . . ?
C14 C26 C25 122.1(3) . . ?
C22 C27 C13 118.4(4) . . ?
C34 C28 C25 111.0(4) . . ?
C34 C28 C31 112.6(6) . . ?
C25 C28 C31 109.0(4) . . ?
C34 C28 C32 109.1(5) . . ?
C25 C28 C32 112.1(4) . . ?
C31 C28 C32 102.8(5) . . ?

_refine_diff_density_max         0.576
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.083



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       ', Luminescent'
