# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ay01
_database_code_depnum_ccdc_archive 'CCDC 1407428'
_audit_update_record             
;
2015-06-18 deposited with the CCDC.
2015-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 Br Cl O3'
_chemical_formula_sum            'C20 H19 Br Cl O3'
_chemical_formula_weight         422.71

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   8.241(3)
_cell_length_b                   9.598(4)
_cell_length_c                   25.276(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.148(6)
_cell_angle_gamma                90
_cell_volume                     1973.8(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2533
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      19.98

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             860
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    2.233
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'SADABS; Bruker,2001'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14919
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.632
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3470
_reflns_number_gt                1919
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT Bruker, 2001'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1164P)²+16.5775P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3470
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1841
_refine_ls_R_factor_gt           0.1232
_refine_ls_wR_factor_ref         0.3589
_refine_ls_wR_factor_gt          0.3237
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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 0.4357(2) 0.19407(18) 0.04341(7) 0.1003(8) Uani 1 1 d . . . . .
Cl1 Cl 0.8937(8) 0.4843(5) 0.0633(3) 0.156(3) Uani 1 1 d . . . . .
O1 O 0.6612(16) -0.2609(10) 0.1609(4) 0.094(3) Uani 1 1 d . . . . .
O2 O 0.5161(12) -0.2403(9) 0.0805(4) 0.077(3) Uani 1 1 d . . . . .
O3 O 0.8341(13) 0.1252(12) 0.2457(4) 0.094(3) Uani 1 1 d . . . . .
C1 C 0.8219(15) -0.0016(12) 0.1458(5) 0.059(3) Uani 1 1 d . . . . .
H1 H 0.8390 -0.0442 0.1815 0.070 Uiso 1 1 calc R U . . .
C2 C 0.8394(13) 0.1556(12) 0.1543(6) 0.057(3) Uani 1 1 d . . . . .
C3 C 0.8540(16) 0.2373(14) 0.1117(7) 0.074(4) Uani 1 1 d . . . . .
H3 H 0.8504 0.1971 0.0781 0.089 Uiso 1 1 calc R U . . .
C4 C 0.8743(19) 0.3807(16) 0.1176(9) 0.103(6) Uani 1 1 d . . . . .
C5 C 0.879(2) 0.4351(18) 0.1694(11) 0.110(7) Uani 1 1 d . . . . .
H5 H 0.8920 0.5306 0.1745 0.132 Uiso 1 1 calc R U . . .
C6 C 0.864(2) 0.353(2) 0.2121(11) 0.117(8) Uani 1 1 d . . . . .
H6 H 0.8665 0.3929 0.2458 0.140 Uiso 1 1 calc R U . . .
C7 C 0.8459(14) 0.2104(17) 0.2052(7) 0.073(4) Uani 1 1 d . . . . .
C8 C 0.6394(14) -0.0377(11) 0.1193(4) 0.050(3) Uani 1 1 d . . . . .
H8 H 0.6278 -0.0146 0.0811 0.060 Uiso 1 1 calc R U . . .
C9 C 0.6073(17) -0.1902(13) 0.1237(5) 0.064(3) Uani 1 1 d . . . . .
C10 C 0.469(2) -0.3885(16) 0.0831(8) 0.107(6) Uani 1 1 d . . . . .
H10A H 0.5460 -0.4453 0.0682 0.161 Uiso 1 1 calc R U . . .
H10B H 0.3608 -0.4018 0.0631 0.161 Uiso 1 1 calc R U . . .
H10C H 0.4689 -0.4145 0.1198 0.161 Uiso 1 1 calc R U . . .
C11 C 0.9548(17) -0.0570(12) 0.1172(6) 0.068(4) Uani 1 1 d . . . . .
H11 H 1.0610 -0.0473 0.1358 0.082 Uiso 1 1 calc R U . . .
C12 C 0.945(2) -0.1136(17) 0.0728(7) 0.090(5) Uani 1 1 d . . . . .
H12 H 0.8402 -0.1277 0.0536 0.108 Uiso 1 1 calc R U . . .
C13 C 1.089(2) -0.1617(17) 0.0474(8) 0.110(6) Uani 1 1 d . . . . .
H13A H 1.1898 -0.1390 0.0705 0.166 Uiso 1 1 calc R U . . .
H13B H 1.0868 -0.1160 0.0135 0.166 Uiso 1 1 calc R U . . .
H13C H 1.0829 -0.2607 0.0420 0.166 Uiso 1 1 calc R U . . .
C14 C 0.5130(13) 0.0449(10) 0.1428(4) 0.046(3) Uani 1 1 d . . . . .
C15 C 0.4934(16) 0.0192(13) 0.1956(6) 0.069(4) Uani 1 1 d . . . . .
H15 H 0.5509 -0.0526 0.2150 0.083 Uiso 1 1 calc R U . . .
C16 C 0.382(2) 0.1061(19) 0.2196(7) 0.089(5) Uani 1 1 d . . . . .
H16 H 0.3678 0.0923 0.2550 0.107 Uiso 1 1 calc R U . . .
C17 C 0.3008(19) 0.205(2) 0.1906(10) 0.101(7) Uani 1 1 d . . . . .
H17 H 0.2319 0.2619 0.2071 0.121 Uiso 1 1 calc R U . . .
C18 C 0.3104(17) 0.2314(15) 0.1383(8) 0.086(5) Uani 1 1 d . . . . .
C19 C 0.4189(14) 0.1502(11) 0.1143(6) 0.064(3) Uani 1 1 d . . . . .
C20 C 0.804(3) 0.183(2) 0.2950(7) 0.134(8) Uani 1 1 d . . . . .
H20A H 0.9023 0.2281 0.3127 0.201 Uiso 1 1 calc R U . . .
H20B H 0.7735 0.1105 0.3175 0.201 Uiso 1 1 calc R U . . .
H20C H 0.7171 0.2503 0.2882 0.201 Uiso 1 1 calc R U . . .


_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 C19 1.868(15) . ?
Cl1 C4 1.72(2) . ?
O1 C9 1.188(15) . ?
O2 C9 1.314(15) . ?
O2 C10 1.479(17) . ?
O3 C7 1.326(18) . ?
O3 C20 1.421(18) . ?
C1 C11 1.502(17) . ?
C1 C2 1.527(16) . ?
C1 C8 1.585(17) . ?
C1 H1 0.9800 . ?
C2 C3 1.351(19) . ?
C2 C7 1.385(18) . ?
C3 C4 1.39(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.40(3) . ?
C5 C6 1.36(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.39(2) . ?
C6 H6 0.9300 . ?
C8 C14 1.505(15) . ?
C8 C9 1.495(16) . ?
C8 H8 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.238(19) . ?
C11 H11 0.9300 . ?
C12 C13 1.51(2) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.389(17) . ?
C14 C19 1.402(16) . ?
C15 C16 1.44(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.32(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.36(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.40(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C9 O2 C10 115.7(12) . . ?
C7 O3 C20 118.6(14) . . ?
C11 C1 C2 110.9(10) . . ?
C11 C1 C8 115.7(10) . . ?
C2 C1 C8 109.7(9) . . ?
C11 C1 H1 106.7 . . ?
C2 C1 H1 106.7 . . ?
C8 C1 H1 106.7 . . ?
C3 C2 C7 121.6(13) . . ?
C3 C2 C1 118.7(12) . . ?
C7 C2 C1 119.6(13) . . ?
C2 C3 C4 120.9(16) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 116.9(17) . . ?
C3 C4 Cl1 120.8(17) . . ?
C5 C4 Cl1 122.4(15) . . ?
C6 C5 C4 122.4(16) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C7 120(2) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
O3 C7 C2 119.2(13) . . ?
O3 C7 C6 122.2(17) . . ?
C2 C7 C6 118.7(18) . . ?
C14 C8 C9 110.2(9) . . ?
C14 C8 C1 112.7(9) . . ?
C9 C8 C1 110.5(10) . . ?
C14 C8 H8 107.8 . . ?
C9 C8 H8 107.8 . . ?
C1 C8 H8 107.8 . . ?
O1 C9 O2 122.8(12) . . ?
O1 C9 C8 124.8(13) . . ?
O2 C9 C8 112.3(11) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C1 130.1(15) . . ?
C12 C11 H11 115.0 . . ?
C1 C11 H11 115.0 . . ?
C11 C12 C13 125.2(17) . . ?
C11 C12 H12 117.4 . . ?
C13 C12 H12 117.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 118.8(11) . . ?
C15 C14 C8 118.7(10) . . ?
C19 C14 C8 122.5(11) . . ?
C14 C15 C16 118.7(14) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 118.9(16) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 124.8(15) . . ?
C16 C17 H17 117.6 . . ?
C18 C17 H17 117.6 . . ?
C17 C18 C19 117.4(16) . . ?
C18 C19 C14 121.3(14) . . ?
C18 C19 Br1 116.2(12) . . ?
C14 C19 Br1 122.4(9) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C11 C1 C2 C3 51.2(16) . . . . ?
C8 C1 C2 C3 -77.8(13) . . . . ?
C11 C1 C2 C7 -126.5(12) . . . . ?
C8 C1 C2 C7 104.4(12) . . . . ?
C7 C2 C3 C4 -1(2) . . . . ?
C1 C2 C3 C4 -178.4(12) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C2 C3 C4 Cl1 179.7(10) . . . . ?
C3 C4 C5 C6 0(3) . . . . ?
Cl1 C4 C5 C6 -179.7(15) . . . . ?
C4 C5 C6 C7 1(3) . . . . ?
C20 O3 C7 C2 -166.2(13) . . . . ?
C20 O3 C7 C6 14(2) . . . . ?
C3 C2 C7 O3 -178.7(12) . . . . ?
C1 C2 C7 O3 -1.0(17) . . . . ?
C3 C2 C7 C6 1.4(18) . . . . ?
C1 C2 C7 C6 179.1(12) . . . . ?
C5 C6 C7 O3 178.8(15) . . . . ?
C5 C6 C7 C2 -1(2) . . . . ?
C11 C1 C8 C14 -167.9(10) . . . . ?
C2 C1 C8 C14 -41.5(13) . . . . ?
C11 C1 C8 C9 68.3(13) . . . . ?
C2 C1 C8 C9 -165.2(10) . . . . ?
C10 O2 C9 O1 6.3(19) . . . . ?
C10 O2 C9 C8 -175.8(11) . . . . ?
C14 C8 C9 O1 -88.9(16) . . . . ?
C1 C8 C9 O1 36.3(17) . . . . ?
C14 C8 C9 O2 93.3(12) . . . . ?
C1 C8 C9 O2 -141.5(10) . . . . ?
C2 C1 C11 C12 -116.7(17) . . . . ?
C8 C1 C11 C12 9(2) . . . . ?
C1 C11 C12 C13 178.1(14) . . . . ?
C9 C8 C14 C15 56.1(14) . . . . ?
C1 C8 C14 C15 -67.8(13) . . . . ?
C9 C8 C14 C19 -126.4(11) . . . . ?
C1 C8 C14 C19 109.7(12) . . . . ?
C19 C14 C15 C16 -2.7(16) . . . . ?
C8 C14 C15 C16 175.0(11) . . . . ?
C14 C15 C16 C17 1.0(19) . . . . ?
C15 C16 C17 C18 2(2) . . . . ?
C16 C17 C18 C19 -3(2) . . . . ?
C17 C18 C19 C14 0.7(19) . . . . ?
C17 C18 C19 Br1 -177.4(10) . . . . ?
C15 C14 C19 C18 1.8(17) . . . . ?
C8 C14 C19 C18 -175.7(11) . . . . ?
C15 C14 C19 Br1 179.8(8) . . . . ?
C8 C14 C19 Br1 2.3(15) . . . . ?

_refine_diff_density_max         0.934
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.119

