# Electronic Supplementary Material (ESI) for ChemComm.
# 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_chenc-26
_database_code_depnum_ccdc_archive 'CCDC 1431438'
_audit_update_record             
;
2015-10-15 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 Br'
_chemical_formula_sum            'C16 H19 Br'
_chemical_formula_weight         291.22

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   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.281(3)
_cell_length_b                   7.3569(12)
_cell_length_c                   19.925(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.092(12)
_cell_angle_gamma                90.00
_cell_volume                     2599.1(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    37
_cell_measurement_theta_min      4.97
_cell_measurement_theta_max      12.49

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    3.138
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2492
_exptl_absorpt_correction_T_max  0.3439
_exptl_absorpt_process_details   'North, et al., 1968'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3068
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2394
_reflns_number_gt                1737
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_cell_refinement       'XSCANS (Bruker, 1997)'
_computing_data_reduction        'XSCANS (Bruker, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'

_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)+(0.0100P)²+5.0000P] 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       0.00523(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2394
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.279
_refine_ls_restrained_S_all      1.279
_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
Br1 Br 0.14269(3) 0.04166(8) 0.40641(3) 0.0738(2) Uani 1 1 d . . .
C1 C 0.1523(2) 0.2488(6) 0.35291(19) 0.0492(10) Uani 1 1 d . . .
C2 C 0.1896(2) 0.3988(6) 0.3851(2) 0.0550(11) Uani 1 1 d . . .
H2 H 0.2116 0.3982 0.4323 0.066 Uiso 1 1 calc R . .
C3 C 0.1938(2) 0.5494(6) 0.3457(2) 0.0534(10) Uani 1 1 d . . .
H3 H 0.2174 0.6532 0.3673 0.064 Uiso 1 1 calc R . .
C4 C 0.1641(2) 0.5519(5) 0.27511(18) 0.0418(9) Uani 1 1 d . . .
C5 C 0.12786(19) 0.3967(5) 0.24251(18) 0.0374(8) Uani 1 1 d . . .
C6 C 0.1223(2) 0.2459(5) 0.28256(18) 0.0432(9) Uani 1 1 d . . .
H6 H 0.0980 0.1419 0.2617 0.052 Uiso 1 1 calc R . .
C7 C 0.1719(2) 0.7199(6) 0.2344(2) 0.0532(10) Uani 1 1 d . . .
H7A H 0.2248 0.7397 0.2363 0.064 Uiso 1 1 calc R . .
H7B H 0.1538 0.8240 0.2555 0.064 Uiso 1 1 calc R . .
C8 C 0.1283(2) 0.7059(5) 0.15931(19) 0.0472(10) Uani 1 1 d . . .
H8 H 0.1426 0.8036 0.1316 0.057 Uiso 1 1 calc R . .
C9 C 0.1446(2) 0.5202(5) 0.13233(18) 0.0405(9) Uani 1 1 d . . .
H9 H 0.1979 0.4891 0.1509 0.049 Uiso 1 1 calc R . .
C10 C 0.0953(2) 0.3976(5) 0.16450(17) 0.0387(8) Uani 1 1 d . . .
C11 C 0.0885(2) 0.2063(5) 0.13422(18) 0.0500(10) Uani 1 1 d . . .
H11A H 0.0486 0.1426 0.1488 0.060 Uiso 1 1 calc R . .
H11B H 0.1352 0.1416 0.1530 0.060 Uiso 1 1 calc R . .
C12 C 0.0718(3) 0.2015(6) 0.0551(2) 0.0620(12) Uani 1 1 d . . .
H12A H 0.0753 0.0771 0.0400 0.074 Uiso 1 1 calc R . .
H12B H 0.0207 0.2435 0.0359 0.074 Uiso 1 1 calc R . .
C13 C 0.1258(3) 0.3183(6) 0.0282(2) 0.0609(12) Uani 1 1 d . . .
H13A H 0.1119 0.3171 -0.0220 0.073 Uiso 1 1 calc R . .
H13B H 0.1763 0.2688 0.0434 0.073 Uiso 1 1 calc R . .
C14 C 0.1253(3) 0.5117(6) 0.05356(19) 0.0532(11) Uani 1 1 d . . .
H14A H 0.0758 0.5643 0.0353 0.064 Uiso 1 1 calc R . .
H14B H 0.1616 0.5830 0.0365 0.064 Uiso 1 1 calc R . .
C15 C 0.0435(2) 0.7042(6) 0.1520(2) 0.0532(10) Uani 1 1 d . . .
H15A H 0.0176 0.7658 0.1099 0.064 Uiso 1 1 calc R . .
H15B H 0.0311 0.7646 0.1911 0.064 Uiso 1 1 calc R . .
C16 C 0.0203(2) 0.5033(5) 0.1496(2) 0.0467(10) Uani 1 1 d . . .
H16A H -0.0110 0.4718 0.1044 0.056 Uiso 1 1 calc R . .
H16B H -0.0073 0.4773 0.1844 0.056 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
Br1 C1 1.892(4) . ?
C1 C2 1.371(6) . ?
C1 C6 1.376(5) . ?
C2 C3 1.370(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(5) . ?
C4 C7 1.504(5) . ?
C5 C6 1.384(5) . ?
C5 C10 1.523(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.517(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C15 1.523(5) . ?
C8 C9 1.523(5) . ?
C8 H8 0.9800 . ?
C9 C14 1.524(5) . ?
C9 C10 1.524(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.524(5) . ?
C10 C16 1.540(5) . ?
C11 C12 1.531(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.503(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.511(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.535(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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 121.2(4) . . ?
C2 C1 Br1 119.3(3) . . ?
C6 C1 Br1 119.5(3) . . ?
C3 C2 C1 118.3(4) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 122.1(4) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 C7 119.7(4) . . ?
C5 C4 C7 121.1(3) . . ?
C6 C5 C4 118.7(3) . . ?
C6 C5 C10 121.7(3) . . ?
C4 C5 C10 119.6(3) . . ?
C1 C6 C5 120.5(4) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C4 C7 C8 112.3(3) . . ?
C4 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C4 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C15 111.9(3) . . ?
C7 C8 C9 107.9(3) . . ?
C15 C8 C9 104.0(3) . . ?
C7 C8 H8 110.9 . . ?
C15 C8 H8 110.9 . . ?
C9 C8 H8 110.9 . . ?
C8 C9 C14 112.6(3) . . ?
C8 C9 C10 101.3(3) . . ?
C14 C9 C10 113.3(3) . . ?
C8 C9 H9 109.8 . . ?
C14 C9 H9 109.8 . . ?
C10 C9 H9 109.8 . . ?
C5 C10 C9 107.9(3) . . ?
C5 C10 C11 112.0(3) . . ?
C9 C10 C11 112.3(3) . . ?
C5 C10 C16 107.9(3) . . ?
C9 C10 C16 102.1(3) . . ?
C11 C10 C16 114.0(3) . . ?
C10 C11 C12 113.9(3) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 111.7(3) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 111.2(4) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C9 111.4(3) . . ?
C13 C14 H14A 109.4 . . ?
C9 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C9 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C8 C15 C16 106.1(3) . . ?
C8 C15 H15A 110.5 . . ?
C16 C15 H15A 110.5 . . ?
C8 C15 H15B 110.5 . . ?
C16 C15 H15B 110.5 . . ?
H15A C15 H15B 108.7 . . ?
C15 C16 C10 104.8(3) . . ?
C15 C16 H16A 110.8 . . ?
C10 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C10 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.076
