# Electronic Supplementary Material (ESI) for ChemComm.
# 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_CL461


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H19 Br O'
_chemical_formula_sum            'C19 H19 Br O'
_chemical_formula_weight         343.25
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.8879(6)
_cell_length_b                   12.4088(9)
_cell_length_c                   13.0415(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1600.15(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3760
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      25.79
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    2.565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_T_max  0.814


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

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.049
_diffrn_reflns_number            12698
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             3674
_reflns_number_gt                3181
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 2012),
           CRYSCAL (T. Roisnel, local program)
;

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

_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)+(0.0302P)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     none
_refine_ls_number_reflns         3674
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.043
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0663
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(7)
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.055

# End of res file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.46772(3) 0.80969(3) 0.94865(2) 0.04110(10) Uani 1 1 d . . .
C1 C 0.6281(3) 0.86202(19) 0.8849(2) 0.0240(6) Uani 1 1 d . . .
C2 C 0.6393(3) 0.86098(19) 0.7797(2) 0.0241(6) Uani 1 1 d . . .
H2 H 0.5675 0.8343 0.7385 0.029 Uiso 1 1 calc R . .
C3 C 0.7568(2) 0.89948(18) 0.7347(2) 0.0224(5) Uani 1 1 d . . .
H3 H 0.765 0.8993 0.6621 0.027 Uiso 1 1 calc R . .
C4 C 0.8633(2) 0.93859(18) 0.79444(19) 0.0186(5) Uani 1 1 d . . .
C5 C 0.8482(3) 0.9388(2) 0.9003(2) 0.0264(6) Uani 1 1 d . . .
H5 H 0.9196 0.9653 0.9421 0.032 Uiso 1 1 calc R . .
C6 C 0.7315(2) 0.90122(19) 0.9460(2) 0.0283(6) Uani 1 1 d . . .
H6 H 0.7222 0.9022 1.0184 0.034 Uiso 1 1 calc R . .
C7 C 0.9909(2) 0.97791(17) 0.74307(19) 0.0186(5) Uani 1 1 d . . .
H7 H 0.9642 1.0201 0.6809 0.022 Uiso 1 1 calc R . .
O8 O 1.05968(17) 1.04898(13) 0.81156(13) 0.0230(4) Uani 1 1 d . . .
C9 C 1.1710(3) 1.10140(19) 0.7616(2) 0.0268(6) Uani 1 1 d . . .
H9A H 1.2144 1.1522 0.8101 0.032 Uiso 1 1 calc R . .
H9B H 1.137 1.1435 0.7025 0.032 Uiso 1 1 calc R . .
C10 C 1.2756(3) 1.02020(18) 0.7243(2) 0.0219(5) Uani 1 1 d . . .
H10A H 1.3185 0.9848 0.7841 0.026 Uiso 1 1 calc R . .
H10B H 1.3471 1.0583 0.6854 0.026 Uiso 1 1 calc R . .
C11 C 1.2100(2) 0.93419(18) 0.65546(19) 0.0193(5) Uani 1 1 d . . .
H11 H 1.1789 0.9707 0.5913 0.023 Uiso 1 1 calc R . .
C12 C 1.0847(2) 0.88596(18) 0.70842(18) 0.0169(5) Uani 1 1 d . . .
H12 H 1.0348 0.8418 0.6566 0.02 Uiso 1 1 calc R . .
C13 C 1.1278(2) 0.8109(2) 0.79567(18) 0.0193(5) Uani 1 1 d . . .
H13A H 1.1854 0.8508 0.8449 0.023 Uiso 1 1 calc R . .
H13B H 1.0469 0.7846 0.8327 0.023 Uiso 1 1 calc R . .
C14 C 1.2065(3) 0.71531(18) 0.7518(2) 0.0222(5) Uani 1 1 d . . .
H14A H 1.2512 0.6767 0.8089 0.027 Uiso 1 1 calc R . .
H14B H 1.1417 0.6648 0.7195 0.027 Uiso 1 1 calc R . .
C15 C 1.3120(3) 0.74624(18) 0.67380(19) 0.0195(5) Uani 1 1 d . . .
C16 C 1.3112(2) 0.84769(18) 0.62514(18) 0.0185(5) Uani 1 1 d . . .
C17 C 1.4067(3) 0.86985(19) 0.5496(2) 0.0251(5) Uani 1 1 d . . .
H17 H 1.405 0.9378 0.5162 0.03 Uiso 1 1 calc R . .
C18 C 1.5044(3) 0.7948(2) 0.5221(2) 0.0291(6) Uani 1 1 d . . .
H18 H 1.5696 0.8116 0.4711 0.035 Uiso 1 1 calc R . .
C19 C 1.5057(2) 0.6948(2) 0.57019(19) 0.0294(6) Uani 1 1 d . . .
H19 H 1.5722 0.6428 0.5523 0.035 Uiso 1 1 calc R . .
C20 C 1.4101(3) 0.67116(18) 0.6440(2) 0.0243(5) Uani 1 1 d . . .
H20 H 1.411 0.6021 0.6754 0.029 Uiso 1 1 calc R . .





#----------------------------------------------------------------------------#
#                   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
Br1 C1 1.905(3) . ?
C1 C2 1.377(4) . ?
C1 C6 1.384(4) . ?
C2 C3 1.387(4) . ?
C2 H2 0.95 . ?
C3 C4 1.397(3) . ?
C3 H3 0.95 . ?
C4 C5 1.389(4) . ?
C4 C7 1.509(3) . ?
C5 C6 1.380(4) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 O8 1.428(3) . ?
C7 C12 1.539(3) . ?
C7 H7 1 . ?
O8 C9 1.435(3) . ?
C9 C10 1.524(4) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.539(3) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C16 1.520(3) . ?
C11 C12 1.539(3) . ?
C11 H11 1 . ?
C12 C13 1.531(3) . ?
C12 H12 1 . ?
C13 C14 1.529(3) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.507(3) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 C20 1.400(3) . ?
C15 C16 1.410(3) . ?
C16 C17 1.391(3) . ?
C17 C18 1.389(3) . ?
C17 H17 0.95 . ?
C18 C19 1.390(4) . ?
C18 H18 0.95 . ?
C19 C20 1.380(4) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?


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(3) . . ?
C2 C1 Br1 119.9(2) . . ?
C6 C1 Br1 119.0(2) . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 C7 122.0(2) . . ?
C3 C4 C7 119.6(2) . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
O8 C7 C4 108.68(19) . . ?
O8 C7 C12 110.75(18) . . ?
C4 C7 C12 113.24(18) . . ?
O8 C7 H7 108 . . ?
C4 C7 H7 108 . . ?
C12 C7 H7 108 . . ?
C7 O8 C9 111.21(18) . . ?
O8 C9 C10 111.47(19) . . ?
O8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
O8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108 . . ?
C9 C10 C11 111.0(2) . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108 . . ?
C16 C11 C10 111.3(2) . . ?
C16 C11 C12 111.85(19) . . ?
C10 C11 C12 110.3(2) . . ?
C16 C11 H11 107.7 . . ?
C10 C11 H11 107.7 . . ?
C12 C11 H11 107.7 . . ?
C13 C12 C7 113.6(2) . . ?
C13 C12 C11 110.23(19) . . ?
C7 C12 C11 109.19(18) . . ?
C13 C12 H12 107.9 . . ?
C7 C12 H12 107.9 . . ?
C11 C12 H12 107.9 . . ?
C14 C13 C12 109.60(19) . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C13 114.0(2) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.6 . . ?
C20 C15 C16 118.2(2) . . ?
C20 C15 C14 119.8(2) . . ?
C16 C15 C14 121.9(2) . . ?
C17 C16 C15 119.4(2) . . ?
C17 C16 C11 119.4(2) . . ?
C15 C16 C11 121.1(2) . . ?
C18 C17 C16 121.5(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 119.2(2) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C15 121.8(2) . . ?
C19 C20 H20 119.1 . . ?
C15 C20 H20 119.1 . . ?


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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(4) . . . . ?
Br1 C1 C2 C3 179.95(17) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C2 C3 C4 C7 178.8(2) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C7 C4 C5 C6 -179.1(2) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
Br1 C1 C6 C5 179.71(19) . . . . ?
C5 C4 C7 O8 -22.5(3) . . . . ?
C3 C4 C7 O8 158.2(2) . . . . ?
C5 C4 C7 C12 101.0(3) . . . . ?
C3 C4 C7 C12 -78.3(3) . . . . ?
C4 C7 O8 C9 -171.43(18) . . . . ?
C12 C7 O8 C9 63.6(2) . . . . ?
C7 O8 C9 C10 -61.3(3) . . . . ?
O8 C9 C10 C11 54.5(3) . . . . ?
C9 C10 C11 C16 -175.3(2) . . . . ?
C9 C10 C11 C12 -50.5(3) . . . . ?
O8 C7 C12 C13 64.8(2) . . . . ?
C4 C7 C12 C13 -57.5(3) . . . . ?
O8 C7 C12 C11 -58.7(2) . . . . ?
C4 C7 C12 C11 179.0(2) . . . . ?
C16 C11 C12 C13 51.0(3) . . . . ?
C10 C11 C12 C13 -73.5(2) . . . . ?
C16 C11 C12 C7 176.47(19) . . . . ?
C10 C11 C12 C7 52.0(3) . . . . ?
C7 C12 C13 C14 173.34(19) . . . . ?
C11 C12 C13 C14 -63.7(2) . . . . ?
C12 C13 C14 C15 45.8(3) . . . . ?
C13 C14 C15 C20 166.3(2) . . . . ?
C13 C14 C15 C16 -17.1(3) . . . . ?
C20 C15 C16 C17 0.2(3) . . . . ?
C14 C15 C16 C17 -176.5(2) . . . . ?
C20 C15 C16 C11 -178.4(2) . . . . ?
C14 C15 C16 C11 4.9(4) . . . . ?
C10 C11 C16 C17 -76.5(3) . . . . ?
C12 C11 C16 C17 159.5(2) . . . . ?
C10 C11 C16 C15 102.1(3) . . . . ?
C12 C11 C16 C15 -21.9(3) . . . . ?
C15 C16 C17 C18 -1.1(4) . . . . ?
C11 C16 C17 C18 177.6(2) . . . . ?
C16 C17 C18 C19 0.9(4) . . . . ?
C17 C18 C19 C20 0.2(4) . . . . ?
C18 C19 C20 C15 -1.1(4) . . . . ?
C16 C15 C20 C19 0.9(4) . . . . ?
C14 C15 C20 C19 177.7(2) . . . . ?


#----------------------------------------------------------------------------#
# END OF CIF FILE FOR CL                                                     #
#----------------------------------------------------------------------------#
_database_code_depnum_ccdc_archive 'CCDC 998587'
