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

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#
#                 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.
#
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#  fide research purposes only. It may contain copyright material
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_sa3346
_audit_creation_date             2014-04-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H17 Br O2'
_chemical_formula_sum            'C19 H17 Br O2'
_chemical_formula_weight         357.23
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.5798(14)
_cell_length_b                   15.675(4)
_cell_length_c                   19.082(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1669.1(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4309
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4686
_cell_measurement_theta_min      2.4991
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.467
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10540
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         3.364
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             2250
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0380
_diffrn_orient_matrix_UB_12      -0.1716
_diffrn_orient_matrix_UB_13      0.0350
_diffrn_orient_matrix_UB_21      -0.0375
_diffrn_orient_matrix_UB_22      -0.0022
_diffrn_orient_matrix_UB_23      -0.0516
_diffrn_orient_matrix_UB_31      0.0409
_diffrn_orient_matrix_UB_32      -0.0150
_diffrn_orient_matrix_UB_33      -0.0291
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3477
_reflns_number_total             3797
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2013)'
_computing_structure_solution    
;
'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 1211 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.024(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3797
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.5150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1048
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C)
2.d :
 C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.80701(11) 0.06104(3) 0.46500(3) 0.04841(19) Uani 1 1 d . . . . .
O1 O 0.3113(6) 0.4233(2) 0.3278(2) 0.0454(9) Uani 1 1 d . . . . .
O2 O 0.5520(7) 0.6578(2) 0.58722(17) 0.0384(8) Uani 1 1 d . . . . .
C1 C 0.6544(8) 0.5547(3) 0.3035(2) 0.0282(9) Uani 1 1 d . . . . .
H1 H 0.5035 0.5654 0.2787 0.034 Uiso 1 1 calc R . . . .
C2 C 0.7130(9) 0.4583(3) 0.2966(2) 0.0302(10) Uani 1 1 d . . . . .
H2 H 0.8679 0.4469 0.3190 0.036 Uiso 1 1 calc R . . . .
C3 C 0.5212(8) 0.4044(3) 0.3316(2) 0.0308(10) Uani 1 1 d . . . . .
C4 C 0.5959(8) 0.3220(3) 0.3650(2) 0.0280(10) Uani 1 1 d . . . . .
C5 C 0.4432(9) 0.2518(3) 0.3594(3) 0.0332(11) Uani 1 1 d . . . . .
H5 H 0.2993 0.2572 0.3352 0.040 Uiso 1 1 calc R . . . .
C6 C 0.5026(9) 0.1745(3) 0.3892(3) 0.0346(11) Uani 1 1 d . . . . .
H6 H 0.4003 0.1279 0.3852 0.042 Uiso 1 1 calc R . . . .
C7 C 0.7176(8) 0.1674(3) 0.4253(2) 0.0295(9) Uani 1 1 d . . . . .
C8 C 0.8704(8) 0.2358(3) 0.4329(3) 0.0323(10) Uani 1 1 d . . . . .
H8 H 1.0115 0.2306 0.4585 0.039 Uiso 1 1 calc R . . . .
C9 C 0.8095(9) 0.3128(3) 0.4017(2) 0.0310(9) Uani 1 1 d . . . . .
H9 H 0.9134 0.3590 0.4053 0.037 Uiso 1 1 calc R . . . .
C10 C 0.7244(13) 0.4307(4) 0.2196(3) 0.0563(16) Uani 1 1 d . . . . .
H10A H 0.5737 0.4425 0.1973 0.084 Uiso 1 1 calc GR . . . .
H10B H 0.7574 0.3707 0.2170 0.084 Uiso 1 1 calc GR . . . .
H10C H 0.8493 0.4618 0.1962 0.084 Uiso 1 1 calc GR . . . .
C11 C 0.8444(9) 0.6052(3) 0.2686(2) 0.0319(10) Uani 1 1 d . . . . .
C12 C 0.9996(10) 0.6453(3) 0.2423(3) 0.0395(12) Uani 1 1 d . . . . .
H12 H 1.1217 0.6769 0.2216 0.047 Uiso 1 1 calc R . . . .
C13 C 0.6223(8) 0.5827(3) 0.3790(2) 0.0252(9) Uani 1 1 d . . . . .
C14 C 0.7965(8) 0.5648(3) 0.4296(2) 0.0286(9) Uani 1 1 d . . . . .
H14 H 0.9343 0.5353 0.4169 0.034 Uiso 1 1 calc R . . . .
C15 C 0.7667(8) 0.5904(3) 0.4983(2) 0.0301(10) Uani 1 1 d . . . . .
H15 H 0.8835 0.5776 0.5314 0.036 Uiso 1 1 calc R . . . .
C16 C 0.5630(8) 0.6353(3) 0.5181(2) 0.0277(9) Uani 1 1 d . . . . .
C17 C 0.3894(8) 0.6539(3) 0.4689(3) 0.0297(9) Uani 1 1 d . . . . .
H17 H 0.2522 0.6837 0.4818 0.036 Uiso 1 1 calc R . . . .
C18 C 0.4218(9) 0.6275(3) 0.3996(2) 0.0293(10) Uani 1 1 d . . . . .
H18 H 0.3050 0.6405 0.3665 0.035 Uiso 1 1 calc R . . . .
C19 C 0.3393(11) 0.6963(3) 0.6114(3) 0.0424(12) Uani 1 1 d . . . . .
H19A H 0.3189 0.7506 0.5890 0.064 Uiso 1 1 calc GR . . . .
H19B H 0.3488 0.7042 0.6612 0.064 Uiso 1 1 calc GR . . . .
H19C H 0.2052 0.6603 0.6005 0.064 Uiso 1 1 calc GR . . . .


_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 C7 1.898(4) . ?
O1 C3 1.210(6) . ?
O2 C16 1.366(6) . ?
O2 C19 1.410(7) . ?
C1 C2 1.550(6) . ?
C1 C11 1.481(7) . ?
C1 C13 1.518(6) . ?
C2 C3 1.518(7) . ?
C2 C10 1.534(6) . ?
C3 C4 1.500(6) . ?
C4 C5 1.396(6) . ?
C4 C9 1.389(7) . ?
C5 C6 1.378(7) . ?
C6 C7 1.388(7) . ?
C7 C8 1.378(6) . ?
C8 C9 1.388(6) . ?
C11 C12 1.183(7) . ?
C13 C14 1.400(6) . ?
C13 C18 1.378(6) . ?
C14 C15 1.380(6) . ?
C15 C16 1.389(6) . ?
C16 C17 1.380(6) . ?
C17 C18 1.398(6) . ?

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
C16 O2 C19 117.7(4) . . ?
C11 C1 C2 109.4(4) . . ?
C11 C1 C13 110.9(4) . . ?
C13 C1 C2 112.8(3) . . ?
C3 C2 C1 110.9(4) . . ?
C3 C2 C10 107.1(4) . . ?
C10 C2 C1 111.4(4) . . ?
O1 C3 C2 121.3(4) . . ?
O1 C3 C4 120.4(4) . . ?
C4 C3 C2 118.1(4) . . ?
C5 C4 C3 118.5(4) . . ?
C9 C4 C3 122.8(4) . . ?
C9 C4 C5 118.7(4) . . ?
C6 C5 C4 120.9(5) . . ?
C5 C6 C7 118.9(4) . . ?
C6 C7 Br1 119.7(3) . . ?
C8 C7 Br1 118.6(4) . . ?
C8 C7 C6 121.7(4) . . ?
C7 C8 C9 118.7(4) . . ?
C8 C9 C4 121.1(4) . . ?
C12 C11 C1 178.3(5) . . ?
C14 C13 C1 121.0(4) . . ?
C18 C13 C1 121.0(4) . . ?
C18 C13 C14 118.0(4) . . ?
C15 C14 C13 120.9(4) . . ?
C14 C15 C16 120.3(4) . . ?
O2 C16 C15 115.5(4) . . ?
O2 C16 C17 124.8(4) . . ?
C17 C16 C15 119.8(4) . . ?
C16 C17 C18 119.4(4) . . ?
C13 C18 C17 121.7(4) . . ?

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
Br1 C7 C8 C9 177.6(3) . . . . ?
O1 C3 C4 C5 31.9(7) . . . . ?
O1 C3 C4 C9 -147.6(5) . . . . ?
O2 C16 C17 C18 179.8(4) . . . . ?
C1 C2 C3 O1 38.8(6) . . . . ?
C1 C2 C3 C4 -147.4(4) . . . . ?
C1 C13 C14 C15 -180.0(4) . . . . ?
C1 C13 C18 C17 -180.0(4) . . . . ?
C2 C1 C13 C14 52.3(6) . . . . ?
C2 C1 C13 C18 -128.5(4) . . . . ?
C2 C3 C4 C5 -142.0(4) . . . . ?
C2 C3 C4 C9 38.5(6) . . . . ?
C3 C4 C5 C6 -179.9(5) . . . . ?
C3 C4 C9 C8 178.8(4) . . . . ?
C4 C5 C6 C7 0.2(7) . . . . ?
C5 C4 C9 C8 -0.7(7) . . . . ?
C5 C6 C7 Br1 -178.5(4) . . . . ?
C5 C6 C7 C8 1.0(7) . . . . ?
C6 C7 C8 C9 -2.0(7) . . . . ?
C7 C8 C9 C4 1.8(7) . . . . ?
C9 C4 C5 C6 -0.4(7) . . . . ?
C10 C2 C3 O1 -82.8(6) . . . . ?
C10 C2 C3 C4 91.0(5) . . . . ?
C11 C1 C2 C3 -179.8(4) . . . . ?
C11 C1 C2 C10 -60.7(5) . . . . ?
C11 C1 C13 C14 -70.8(5) . . . . ?
C11 C1 C13 C18 108.5(5) . . . . ?
C13 C1 C2 C3 56.3(5) . . . . ?
C13 C1 C2 C10 175.5(4) . . . . ?
C13 C14 C15 C16 -0.6(7) . . . . ?
C14 C13 C18 C17 -0.7(6) . . . . ?
C14 C15 C16 O2 -179.8(4) . . . . ?
C14 C15 C16 C17 0.3(7) . . . . ?
C15 C16 C17 C18 -0.2(6) . . . . ?
C16 C17 C18 C13 0.5(7) . . . . ?
C18 C13 C14 C15 0.8(6) . . . . ?
C19 O2 C16 C15 -174.2(4) . . . . ?
C19 O2 C16 C17 5.8(7) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1004896'
