# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_d19327
_database_code_depnum_ccdc_archive 'CCDC 1830878'
_audit_update_record             
;
2018-03-19 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H30'
_chemical_formula_sum            'C42 H30'
_chemical_formula_weight         534.66

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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                   9.6495(9)
_cell_length_b                   25.376(2)
_cell_length_c                   14.0175(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.672(3)
_cell_angle_gamma                90.00
_cell_volume                     3270.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.213
_cell_measurement_theta_max      24.871

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.086
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9688
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'D8 Venture'
_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            49860
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.04
_reflns_number_total             5737
_reflns_number_gt                4665
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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.
;

_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.070(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5737
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0978
_refine_ls_wR_factor_ref         0.3573
_refine_ls_wR_factor_gt          0.3319
_refine_ls_goodness_of_fit_ref   1.603
_refine_ls_restrained_S_all      1.603
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8685(3) 0.58279(11) 0.76426(19) 0.0421(7) Uani 1 1 d . . .
C2 C 0.7567(3) 0.58431(12) 0.8188(2) 0.0455(7) Uani 1 1 d . . .
C3 C 0.7344(3) 0.62979(13) 0.8690(2) 0.0518(8) Uani 1 1 d . . .
H3 H 0.7908 0.6605 0.8694 0.062 Uiso 1 1 calc R . .
C4 C 0.6297(4) 0.62970(15) 0.9179(2) 0.0611(9) Uani 1 1 d . . .
H4 H 0.6173 0.6603 0.9534 0.073 Uiso 1 1 calc R . .
C5 C 0.5439(4) 0.58695(16) 0.9166(3) 0.0665(10) Uani 1 1 d . . .
H5 H 0.4704 0.5882 0.9488 0.080 Uiso 1 1 calc R . .
C6 C 0.5650(4) 0.54210(15) 0.8681(3) 0.0651(10) Uani 1 1 d . . .
H6 H 0.5065 0.5119 0.8670 0.078 Uiso 1 1 calc R . .
C7 C 0.6729(3) 0.54101(13) 0.8203(2) 0.0553(8) Uani 1 1 d . . .
H7 H 0.6882 0.5096 0.7881 0.066 Uiso 1 1 calc R . .
C8 C 0.9625(3) 0.53437(11) 0.7842(2) 0.0469(7) Uani 1 1 d . . .
C9 C 1.0336(3) 0.51939(14) 0.8806(2) 0.0598(9) Uani 1 1 d . . .
H9 H 1.0199 0.5390 0.9348 0.072 Uiso 1 1 calc R . .
C10 C 1.1267(4) 0.47530(16) 0.9006(3) 0.0765(11) Uani 1 1 d . . .
H10 H 1.1757 0.4656 0.9678 0.092 Uiso 1 1 calc R . .
C11 C 1.1466(4) 0.44692(15) 0.8247(4) 0.0764(11) Uani 1 1 d . . .
H11 H 1.2105 0.4175 0.8384 0.092 Uiso 1 1 calc R . .
C12 C 1.0742(5) 0.46044(14) 0.7272(3) 0.0779(11) Uani 1 1 d . . .
H12 H 1.0870 0.4398 0.6739 0.093 Uiso 1 1 calc R . .
C13 C 0.9818(4) 0.50430(12) 0.7057(3) 0.0590(9) Uani 1 1 d . . .
H13 H 0.9326 0.5135 0.6382 0.071 Uiso 1 1 calc R . .
C14 C 0.8862(3) 0.62187(11) 0.7040(2) 0.0419(7) Uani 1 1 d . . .
C15 C 1.0063(3) 0.62305(11) 0.6564(2) 0.0437(7) Uani 1 1 d . . .
C16 C 1.1510(3) 0.61418(11) 0.7114(2) 0.0461(7) Uani 1 1 d . . .
H16 H 1.1759 0.6074 0.7813 0.055 Uiso 1 1 calc R . .
C17 C 1.2590(3) 0.61525(12) 0.6649(3) 0.0529(8) Uani 1 1 d . . .
H17 H 1.3572 0.6088 0.7028 0.063 Uiso 1 1 calc R . .
C18 C 1.2247(3) 0.62547(13) 0.5651(3) 0.0584(9) Uani 1 1 d . . .
H18 H 1.2992 0.6258 0.5337 0.070 Uiso 1 1 calc R . .
C19 C 1.0830(4) 0.63540(14) 0.5093(2) 0.0591(9) Uani 1 1 d . . .
H19 H 1.0597 0.6427 0.4397 0.071 Uiso 1 1 calc R . .
C20 C 0.9742(3) 0.63470(13) 0.5555(2) 0.0514(8) Uani 1 1 d . . .
H20 H 0.8767 0.6423 0.5174 0.062 Uiso 1 1 calc R . .
C21 C 0.7868(3) 0.66810(11) 0.67810(19) 0.0412(7) Uani 1 1 d . . .
C22 C 0.8451(3) 0.71922(11) 0.6899(2) 0.0473(7) Uani 1 1 d . . .
H22 H 0.9477 0.7238 0.7110 0.057 Uiso 1 1 calc R . .
C23 C 0.7554(3) 0.76305(11) 0.6713(2) 0.0473(7) Uani 1 1 d . . .
H23 H 0.7975 0.7972 0.6818 0.057 Uiso 1 1 calc R . .
C24 C 0.6043(3) 0.75796(10) 0.6375(2) 0.0402(7) Uani 1 1 d . . .
C25 C 0.5471(3) 0.70698(11) 0.6214(2) 0.0417(7) Uani 1 1 d . . .
H25 H 0.4447 0.7023 0.5967 0.050 Uiso 1 1 calc R . .
C26 C 0.6366(3) 0.66305(11) 0.6409(2) 0.0418(7) Uani 1 1 d . . .
H26 H 0.5946 0.6289 0.6286 0.050 Uiso 1 1 calc R . .
C27 C 0.5094(3) 0.80486(11) 0.62293(19) 0.0407(7) Uani 1 1 d . . .
C28 C 0.3762(3) 0.80585(12) 0.5464(2) 0.0455(7) Uani 1 1 d . . .
H28 H 0.3537 0.7784 0.4981 0.055 Uiso 1 1 calc R . .
C29 C 0.2764(3) 0.84622(12) 0.5398(2) 0.0530(8) Uani 1 1 d . . .
C30 C 0.3247(4) 0.89187(13) 0.5960(3) 0.0605(9) Uani 1 1 d . . .
H30 H 0.2676 0.9231 0.5821 0.073 Uiso 1 1 calc R . .
C31 C 0.4553(4) 0.89152(12) 0.6716(3) 0.0593(9) Uani 1 1 d . . .
H31 H 0.4881 0.9227 0.7092 0.071 Uiso 1 1 calc R . .
C32 C 0.5403(3) 0.84576(11) 0.6937(2) 0.0474(7) Uani 1 1 d . . .
C33 C 0.6250(4) 0.83529(13) 0.8006(2) 0.0585(9) Uani 1 1 d . . .
H33 H 0.7262 0.8428 0.8238 0.070 Uiso 1 1 calc R . .
C34 C 0.5591(4) 0.81556(15) 0.8633(3) 0.0680(10) Uani 1 1 d . . .
H34 H 0.6121 0.8084 0.9311 0.082 Uiso 1 1 calc R . .
C35 C 0.3983(4) 0.80480(14) 0.8241(2) 0.0610(9) Uani 1 1 d . . .
C36 C 0.3488(4) 0.75845(13) 0.7709(2) 0.0550(8) Uani 1 1 d . . .
H36 H 0.4043 0.7270 0.7876 0.066 Uiso 1 1 calc R . .
C37 C 0.2197(3) 0.75835(13) 0.6941(3) 0.0558(9) Uani 1 1 d . . .
H37 H 0.1868 0.7268 0.6577 0.067 Uiso 1 1 calc R . .
C38 C 0.1371(3) 0.80404(15) 0.6695(3) 0.0644(10) Uani 1 1 d . . .
C39 C 0.1686(5) 0.84467(16) 0.7384(4) 0.0782(12) Uani 1 1 d . . .
H39 H 0.1009 0.8725 0.7335 0.094 Uiso 1 1 calc R . .
C40 C 0.3003(5) 0.84458(16) 0.8149(3) 0.0732(11) Uani 1 1 d . . .
H40 H 0.3223 0.8728 0.8616 0.088 Uiso 1 1 calc R . .
C41 C 0.0503(3) 0.81438(17) 0.5623(3) 0.0747(11) Uani 1 1 d . . .
H41 H -0.0509 0.8068 0.5394 0.090 Uiso 1 1 calc R . .
C42 C 0.1162(3) 0.83406(15) 0.5004(3) 0.0673(10) Uani 1 1 d . . .
H42 H 0.0636 0.8404 0.4322 0.081 Uiso 1 1 calc R . .


_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 C14 1.347(4) . ?
C1 C2 1.500(3) . ?
C1 C8 1.502(4) . ?
C2 C7 1.369(4) . ?
C2 C3 1.402(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.362(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.370(4) . ?
C8 C13 1.398(4) . ?
C9 C10 1.409(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.345(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C21 1.489(4) . ?
C14 C15 1.503(3) . ?
C15 C20 1.385(4) . ?
C15 C16 1.394(4) . ?
C16 C17 1.387(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.361(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.391(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C26 1.389(4) . ?
C21 C22 1.404(4) . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.395(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.398(4) . ?
C24 C27 1.478(4) . ?
C25 C26 1.386(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.402(4) . ?
C27 C32 1.404(4) . ?
C28 C29 1.389(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.399(5) . ?
C29 C42 1.507(4) . ?
C30 C31 1.379(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.401(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.498(5) . ?
C33 C34 1.329(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.505(5) . ?
C34 H34 0.9500 . ?
C35 C40 1.362(5) . ?
C35 C36 1.397(5) . ?
C36 C37 1.377(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.390(5) . ?
C37 H37 0.9500 . ?
C38 C39 1.381(6) . ?
C38 C41 1.505(6) . ?
C39 C40 1.392(6) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C42 1.321(5) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?

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
C14 C1 C2 123.3(2) . . ?
C14 C1 C8 122.3(2) . . ?
C2 C1 C8 114.4(2) . . ?
C7 C2 C3 118.1(3) . . ?
C7 C2 C1 120.5(3) . . ?
C3 C2 C1 121.4(3) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C2 C7 C6 121.4(3) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C9 C8 C13 118.6(3) . . ?
C9 C8 C1 120.3(3) . . ?
C13 C8 C1 121.1(3) . . ?
C8 C9 C10 120.9(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 119.5(3) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C1 C14 C21 122.5(2) . . ?
C1 C14 C15 123.7(2) . . ?
C21 C14 C15 113.8(2) . . ?
C20 C15 C16 118.4(2) . . ?
C20 C15 C14 119.6(2) . . ?
C16 C15 C14 122.0(2) . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 119.5(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C15 C20 C19 120.8(3) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C26 C21 C22 117.7(2) . . ?
C26 C21 C14 122.7(2) . . ?
C22 C21 C14 119.6(2) . . ?
C23 C22 C21 121.0(2) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 121.2(3) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C25 117.5(2) . . ?
C23 C24 C27 120.8(2) . . ?
C25 C24 C27 121.7(2) . . ?
C26 C25 C24 121.4(2) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C21 121.1(2) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
C28 C27 C32 118.4(2) . . ?
C28 C27 C24 120.4(3) . . ?
C32 C27 C24 120.6(2) . . ?
C29 C28 C27 121.3(3) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C30 117.9(3) . . ?
C28 C29 C42 119.1(3) . . ?
C30 C29 C42 120.4(3) . . ?
C31 C30 C29 119.9(3) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 120.8(3) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C31 C32 C27 118.2(3) . . ?
C31 C32 C33 118.3(3) . . ?
C27 C32 C33 120.7(3) . . ?
C34 C33 C32 120.2(3) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 118.3(3) . . ?
C33 C34 H34 120.8 . . ?
C35 C34 H34 120.8 . . ?
C40 C35 C36 117.3(3) . . ?
C40 C35 C34 120.6(3) . . ?
C36 C35 C34 119.7(3) . . ?
C37 C36 C35 120.0(3) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 120.5(3) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C39 C38 C37 117.5(4) . . ?
C39 C38 C41 120.3(3) . . ?
C37 C38 C41 119.8(4) . . ?
C38 C39 C40 119.5(3) . . ?
C38 C39 H39 120.2 . . ?
C40 C39 H39 120.2 . . ?
C35 C40 C39 121.3(4) . . ?
C35 C40 H40 119.3 . . ?
C39 C40 H40 119.3 . . ?
C42 C41 C38 119.3(3) . . ?
C42 C41 H41 120.3 . . ?
C38 C41 H41 120.3 . . ?
C41 C42 C29 118.8(3) . . ?
C41 C42 H42 120.6 . . ?
C29 C42 H42 120.6 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.343
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.092
####################################################################### 
# 
# 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_d19302
_database_code_depnum_ccdc_archive 'CCDC 1833417'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 Br'
_chemical_formula_sum            'C16 H11 Br'
_chemical_formula_weight         283.16

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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                   13.8830(16)
_cell_length_b                   11.6713(13)
_cell_length_c                   7.3807(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.738(4)
_cell_angle_gamma                90.00
_cell_volume                     1194.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5737
_cell_measurement_theta_min      2.938
_cell_measurement_theta_max      25.199

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    3.412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5787
_exptl_absorpt_correction_T_max  0.8756
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(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  'D8 Venture'
_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            14005
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         25.32
_reflns_number_total             2147
_reflns_number_gt                1723
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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.
;

_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)+(0.0400P)²+2.8961P] where P=(Fo²+2Fc²)/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         2147
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.1542(3) 0.6053(3) 0.3098(6) 0.0346(9) Uani 1 1 d . . .
C2 C 0.1551(3) 0.5032(3) 0.4055(5) 0.0334(9) Uani 1 1 d . . .
C3 C 0.2314(3) 0.4900(3) 0.5356(5) 0.0366(9) Uani 1 1 d . . .
H3 H 0.2276 0.4321 0.6255 0.044 Uiso 1 1 calc R . .
C4 C 0.3120(3) 0.5596(3) 0.5354(5) 0.0351(9) Uani 1 1 d . . .
H4 H 0.3631 0.5488 0.6241 0.042 Uiso 1 1 calc R . .
C5 C 0.3186(3) 0.6453(3) 0.4061(5) 0.0319(8) Uani 1 1 d . . .
C6 C 0.2348(3) 0.6763(3) 0.3075(5) 0.0338(9) Uani 1 1 d . . .
H6 H 0.2324 0.7452 0.2391 0.041 Uiso 1 1 calc R . .
C7 C 0.4157(3) 0.6763(3) 0.3391(5) 0.0360(9) Uani 1 1 d . . .
H7 H 0.4477 0.7441 0.3800 0.043 Uiso 1 1 calc R . .
C8 C 0.4563(3) 0.6065(3) 0.2206(5) 0.0338(9) Uani 1 1 d . . .
H8 H 0.5185 0.6224 0.1785 0.041 Uiso 1 1 calc R . .
C9 C 0.4012(3) 0.5025(3) 0.1558(5) 0.0323(8) Uani 1 1 d . . .
C10 C 0.3257(3) 0.5161(3) 0.0252(5) 0.0342(9) Uani 1 1 d . . .
H10 H 0.3291 0.5742 -0.0643 0.041 Uiso 1 1 calc R . .
C11 C 0.2457(3) 0.4446(3) 0.0263(5) 0.0351(9) Uani 1 1 d . . .
H11 H 0.1947 0.4539 -0.0630 0.042 Uiso 1 1 calc R . .
C12 C 0.2398(3) 0.3593(3) 0.1576(5) 0.0337(9) Uani 1 1 d . . .
C13 C 0.3238(3) 0.3301(3) 0.2562(6) 0.0371(9) Uani 1 1 d . . .
H13 H 0.3265 0.2612 0.3249 0.045 Uiso 1 1 calc R . .
C14 C 0.4040(3) 0.4016(3) 0.2549(6) 0.0369(9) Uani 1 1 d . . .
H14 H 0.4613 0.3809 0.3226 0.044 Uiso 1 1 calc R . .
C15 C 0.1425(3) 0.3294(3) 0.2244(6) 0.0386(9) Uani 1 1 d . . .
H15 H 0.1106 0.2613 0.1843 0.046 Uiso 1 1 calc R . .
C16 C 0.1013(3) 0.3996(3) 0.3407(6) 0.0367(9) Uani 1 1 d . . .
H16 H 0.0388 0.3837 0.3813 0.044 Uiso 1 1 calc R . .
Br1 Br 0.05053(3) 0.63595(4) 0.13880(7) 0.0543(2) Uani 1 1 d . . .


_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 1.385(6) . ?
C1 C6 1.392(5) . ?
C1 Br1 1.903(4) . ?
C2 C3 1.404(6) . ?
C2 C16 1.488(5) . ?
C3 C4 1.383(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(5) . ?
C5 C7 1.502(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.339(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.500(5) . ?
C8 H8 0.9500 . ?
C9 C14 1.386(6) . ?
C9 C10 1.399(5) . ?
C10 C11 1.388(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(6) . ?
C12 C15 1.501(5) . ?
C13 C14 1.392(6) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.335(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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 122.0(4) . . ?
C2 C1 Br1 119.2(3) . . ?
C6 C1 Br1 117.5(3) . . ?
C1 C2 C3 115.5(4) . . ?
C1 C2 C16 122.9(4) . . ?
C3 C2 C16 118.8(3) . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 117.8(4) . . ?
C4 C5 C7 119.3(4) . . ?
C6 C5 C7 120.5(4) . . ?
C5 C6 C1 119.5(4) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C8 C7 C5 118.7(3) . . ?
C8 C7 H7 120.6 . . ?
C5 C7 H7 120.6 . . ?
C7 C8 C9 118.5(3) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C14 C9 C10 117.4(4) . . ?
C14 C9 C8 121.2(4) . . ?
C10 C9 C8 118.8(3) . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 117.7(4) . . ?
C13 C12 C15 121.2(4) . . ?
C11 C12 C15 118.5(4) . . ?
C12 C13 C14 120.1(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.7(4) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C12 119.3(3) . . ?
C16 C15 H15 120.4 . . ?
C12 C15 H15 120.4 . . ?
C15 C16 C2 118.8(3) . . ?
C15 C16 H16 120.6 . . ?
C2 C16 H16 120.6 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.32
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.443
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.077
