# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelx

_audit_creation_date             2013-07-23T09:44:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C30 H16 Br2'
_chemical_formula_weight         536.25

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.362(3)
_cell_length_b                   15.987(2)
_cell_length_c                   8.160(1)
_cell_angle_alpha                90
_cell_angle_beta                 97.389(9)
_cell_angle_gamma                90
_cell_volume                     2116.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    19661
_cell_measurement_theta_min      2.815
_cell_measurement_theta_max      28.624
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_coefficient_mu    3.846
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_T_max  0.787

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.123
_diffrn_reflns_number            18497
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.815
_diffrn_reflns_theta_max         28.624
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.956
_reflns_number_total             5184
_reflns_number_gt                2065
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.1250P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5184
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.2121
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.2444
_refine_ls_wR_factor_gt          0.1962
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.834
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.128

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2109(4) 0.0424(4) 0.6982(8) 0.0376(17) Uani 1 d . .
C2 C 0.2856(4) 0.0089(4) 0.6557(8) 0.0388(17) Uani 1 d . .
H2 H 0.3333 0.0144 0.7304 0.047 Uiso 1 calc . .
C3 C 0.2903(5) -0.0311(6) 0.5090(9) 0.057(2) Uani 1 d . .
H3 H 0.3404 -0.0522 0.4854 0.068 Uiso 1 calc . .
C4 C 0.2190(5) -0.0402(6) 0.3939(9) 0.058(2) Uani 1 d . .
H4 H 0.2206 -0.0719 0.2987 0.069 Uiso 1 calc . .
C5 C 0.1471(5) -0.0020(6) 0.4236(9) 0.053(2) Uani 1 d . .
H5 H 0.1014 -0.004 0.3432 0.064 Uiso 1 calc . .
C6 C 0.1414(4) 0.0395(5) 0.5714(9) 0.0436(18) Uani 1 d . .
C7 C 0.0691(5) 0.0822(5) 0.5958(10) 0.051(2) Uani 1 d . .
H7 H 0.023 0.0785 0.5166 0.062 Uiso 1 calc . .
C8 C 0.0657(5) 0.1284(5) 0.7323(10) 0.053(2) Uani 1 d . .
H8 H 0.0184 0.1593 0.7416 0.064 Uiso 1 calc . .
C9 C 0.1331(5) 0.1317(5) 0.8650(10) 0.0459(19) Uani 1 d . .
C10 C 0.2022(4) 0.0801(4) 0.8546(9) 0.0377(16) Uani 1 d . .
C11 C 0.2613(4) 0.0702(4) 1.0019(8) 0.0356(16) Uani 1 d . .
C12 C 0.2638(5) 0.1325(5) 1.1227(9) 0.0455(19) Uani 1 d . .
C13 C 0.1943(5) 0.1894(5) 1.1190(11) 0.057(2) Uani 1 d . .
H13 H 0.1946 0.2305 1.1997 0.069 Uiso 1 calc . .
C14 C 0.1300(5) 0.1831(5) 1.0006(10) 0.0494(19) Uani 1 d . .
H14 H 0.0824 0.2137 1.0095 0.059 Uiso 1 calc . .
C15 C 0.3352(5) 0.1379(5) 1.2392(10) 0.053(2) Uani 1 d . .
C16 C 0.3982(5) 0.0842(5) 1.2405(9) 0.048(2) Uani 1 d . .
C17 C 0.3880(4) 0.0091(5) 1.1407(8) 0.0400(17) Uani 1 d . .
C18 C 0.3155(4) -0.0016(4) 1.0345(8) 0.0344(16) Uani 1 d . .
C19 C 0.2960(4) -0.0846(4) 0.9657(8) 0.0382(17) Uani 1 d . .
C20 C 0.3615(5) -0.1398(5) 0.9583(9) 0.0435(18) Uani 1 d . .
C21 C 0.4402(5) -0.1218(5) 1.0508(9) 0.052(2) Uani 1 d . .
H21 H 0.484 -0.1583 1.0452 0.063 Uiso 1 calc . .
C22 C 0.4513(5) -0.0533(6) 1.1449(10) 0.052(2) Uani 1 d . .
H22 H 0.5006 -0.046 1.2139 0.063 Uiso 1 calc . .
C23 C 0.3487(5) -0.2136(5) 0.8608(10) 0.052(2) Uani 1 d . .
H23 H 0.3929 -0.2496 0.8543 0.062 Uiso 1 calc . .
C24 C 0.2743(6) -0.2329(5) 0.7776(10) 0.058(2) Uani 1 d . .
H24 H 0.2694 -0.2775 0.7037 0.07 Uiso 1 calc . .
C25 C 0.2032(5) -0.1850(5) 0.8028(8) 0.0434(18) Uani 1 d . .
C26 C 0.2133(4) -0.1139(4) 0.9062(7) 0.0325(15) Uani 1 d . .
C27 C 0.1409(4) -0.0775(4) 0.9545(8) 0.0394(17) Uani 1 d . .
H27 H 0.1455 -0.0341 1.0309 0.047 Uiso 1 calc . .
C28 C 0.0639(5) -0.1058(5) 0.8899(9) 0.0441(18) Uani 1 d . .
H28 H 0.0172 -0.0809 0.9226 0.053 Uiso 1 calc . .
C29 C 0.0550(5) -0.1706(5) 0.7770(9) 0.0470(19) Uani 1 d . .
H29 H 0.0027 -0.1871 0.7303 0.056 Uiso 1 calc . .
C30 C 0.1214(6) -0.2095(5) 0.7350(10) 0.056(2) Uani 1 d . .
H30 H 0.1145 -0.2535 0.66 0.068 Uiso 1 calc . .
Br1 Br 0.34324(7) 0.22742(7) 1.39437(13) 0.0794(4) Uani 1 d . .
Br2 Br 0.49892(6) 0.10314(7) 1.37414(11) 0.0712(4) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.419(10) . ?
C1 C10 1.434(10) . ?
C1 C6 1.436(10) . ?
C2 C3 1.368(11) . ?
C2 H2 0.93 . ?
C3 C4 1.408(11) . ?
C3 H3 0.93 . ?
C4 C5 1.374(12) . ?
C4 H4 0.93 . ?
C5 C6 1.391(11) . ?
C5 H5 0.93 . ?
C6 C7 1.402(11) . ?
C7 C8 1.344(11) . ?
C7 H7 0.93 . ?
C8 C9 1.443(11) . ?
C8 H8 0.93 . ?
C9 C14 1.384(11) . ?
C9 C10 1.411(10) . ?
C10 C11 1.451(10) . ?
C11 C12 1.398(10) . ?
C11 C18 1.454(10) . ?
C12 C15 1.411(11) . ?
C12 C13 1.453(11) . ?
C13 C14 1.338(11) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 C16 1.339(12) . ?
C15 Br1 1.904(8) . ?
C16 C17 1.448(11) . ?
C16 Br2 1.881(8) . ?
C17 C18 1.386(9) . ?
C17 C22 1.435(11) . ?
C18 C19 1.461(10) . ?
C19 C20 1.395(10) . ?
C19 C26 1.456(10) . ?
C20 C23 1.424(11) . ?
C20 C21 1.434(11) . ?
C21 C22 1.337(11) . ?
C21 H21 0.93 . ?
C22 H22 0.93 . ?
C23 C24 1.351(12) . ?
C23 H23 0.93 . ?
C24 C25 1.429(12) . ?
C24 H24 0.93 . ?
C25 C26 1.413(9) . ?
C25 C30 1.436(11) . ?
C26 C27 1.420(10) . ?
C27 C28 1.378(10) . ?
C27 H27 0.93 . ?
C28 C29 1.381(10) . ?
C28 H28 0.93 . ?
C29 C30 1.334(12) . ?
C29 H29 0.93 . ?
C30 H30 0.93 . ?

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 C10 124.3(6) . . ?
C2 C1 C6 116.0(6) . . ?
C10 C1 C6 119.7(6) . . ?
C3 C2 C1 122.5(7) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 119.8(8) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.4(8) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.3(7) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 120.5(7) . . ?
C5 C6 C1 120.4(7) . . ?
C7 C6 C1 119.0(7) . . ?
C8 C7 C6 120.8(8) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 122.2(8) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C14 C9 C10 120.5(7) . . ?
C14 C9 C8 121.2(8) . . ?
C10 C9 C8 118.3(7) . . ?
C9 C10 C1 118.1(6) . . ?
C9 C10 C11 117.9(7) . . ?
C1 C10 C11 124.0(6) . . ?
C12 C11 C10 117.6(7) . . ?
C12 C11 C18 118.2(7) . . ?
C10 C11 C18 124.2(6) . . ?
C11 C12 C15 117.7(7) . . ?
C11 C12 C13 118.6(7) . . ?
C15 C12 C13 123.7(7) . . ?
C14 C13 C12 120.6(8) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C9 121.0(8) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C16 C15 C12 122.4(8) . . ?
C16 C15 Br1 119.3(6) . . ?
C12 C15 Br1 118.3(6) . . ?
C15 C16 C17 119.6(7) . . ?
C15 C16 Br2 121.1(6) . . ?
C17 C16 Br2 119.3(6) . . ?
C18 C17 C22 119.1(7) . . ?
C18 C17 C16 118.7(7) . . ?
C22 C17 C16 122.1(7) . . ?
C17 C18 C11 118.0(6) . . ?
C17 C18 C19 118.6(6) . . ?
C11 C18 C19 123.4(6) . . ?
C20 C19 C26 118.0(7) . . ?
C20 C19 C18 117.4(7) . . ?
C26 C19 C18 124.6(6) . . ?
C19 C20 C23 119.3(7) . . ?
C19 C20 C21 119.5(7) . . ?
C23 C20 C21 121.1(7) . . ?
C22 C21 C20 120.9(8) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C17 120.7(8) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
C24 C23 C20 121.9(7) . . ?
C24 C23 H23 119.1 . . ?
C20 C23 H23 119.1 . . ?
C23 C24 C25 120.2(8) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 118.9(7) . . ?
C26 C25 C30 118.7(7) . . ?
C24 C25 C30 122.3(7) . . ?
C25 C26 C27 117.3(6) . . ?
C25 C26 C19 119.3(6) . . ?
C27 C26 C19 123.3(6) . . ?
C28 C27 C26 120.9(7) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 120.9(7) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C30 C29 C28 120.1(7) . . ?
C30 C29 H29 120 . . ?
C28 C29 H29 120 . . ?
C29 C30 C25 121.6(8) . . ?
C29 C30 H30 119.2 . . ?
C25 C30 H30 119.2 . . ?

# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 951885'
