# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_csh_3_14205
_database_code_depnum_ccdc_archive 'CCDC 1500487'
_audit_update_record             
;
2016-08-22 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 O3'
_chemical_formula_weight         270.31

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   7.6236(2)
_cell_length_b                   6.9169(2)
_cell_length_c                   26.9337(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.6170(10)
_cell_angle_gamma                90.00
_cell_volume                     1413.44(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9996
_cell_measurement_theta_min      2.953
_cell_measurement_theta_max      28.7535

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9847
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150
_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 APEX-II CCD'
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19971
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0128
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         28.78
_reflns_number_total             3670
_reflns_number_gt                3327
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.1000P)²+0.1400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3670
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1449
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_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
O1 O 0.83689(9) 1.14450(10) 0.54138(3) 0.02321(19) Uani 1 1 d . . .
O3 O 0.66140(10) 0.60446(11) 0.60632(3) 0.0267(2) Uani 1 1 d . . .
H3 H 0.6532 0.7072 0.5911 0.040 Uiso 1 1 calc R . .
C4 C 0.95367(12) 0.89562(13) 0.59331(3) 0.0181(2) Uani 1 1 d . . .
C8 C 1.12416(12) 0.97145(14) 0.59745(3) 0.0203(2) Uani 1 1 d . . .
C6 C 1.13389(13) 0.70479(14) 0.64860(3) 0.0193(2) Uani 1 1 d . . .
C12 C 1.20365(13) 0.57311(14) 0.68918(4) 0.0199(2) Uani 1 1 d . . .
C10 C 0.82327(13) 0.58443(14) 0.62784(3) 0.0198(2) Uani 1 1 d . . .
C3 C 0.80250(13) 0.98356(14) 0.56574(3) 0.0204(2) Uani 1 1 d . . .
C7 C 1.23146(13) 0.85323(15) 0.63136(4) 0.0232(2) Uani 1 1 d . . .
H7 H 1.3508 0.8735 0.6406 0.028 Uiso 1 1 calc R . .
C9 C 1.19445(14) 1.14605(15) 0.57318(4) 0.0262(2) Uani 1 1 d . . .
H9A H 1.1671 1.1375 0.5377 0.039 Uiso 1 1 calc R . .
H9B H 1.3199 1.1523 0.5809 0.039 Uiso 1 1 calc R . .
H9C H 1.1413 1.2602 0.5854 0.039 Uiso 1 1 calc R . .
C5 C 0.95547(12) 0.71945(13) 0.62440(3) 0.0178(2) Uani 1 1 d . . .
C13 C 1.13374(14) 0.57913(14) 0.73523(4) 0.0227(2) Uani 1 1 d . . .
H13 H 1.0405 0.6620 0.7397 0.027 Uiso 1 1 calc R . .
C17 C 1.34471(14) 0.45002(15) 0.68340(4) 0.0254(2) Uani 1 1 d . . .
H17 H 1.3947 0.4470 0.6533 0.030 Uiso 1 1 calc R . .
C15 C 1.33996(15) 0.33723(16) 0.76803(4) 0.0297(3) Uani 1 1 d . . .
H15 H 1.3844 0.2575 0.7941 0.036 Uiso 1 1 calc R . .
C1 C 0.75545(15) 1.41449(16) 0.48936(4) 0.0294(2) Uani 1 1 d . . .
H1A H 0.8089 1.5018 0.5141 0.044 Uiso 1 1 calc R . .
H1B H 0.6601 1.4785 0.4700 0.044 Uiso 1 1 calc R . .
H1C H 0.8417 1.3741 0.4678 0.044 Uiso 1 1 calc R . .
C14 C 1.20212(15) 0.46267(15) 0.77438(4) 0.0257(2) Uani 1 1 d . . .
H14 H 1.1554 0.4688 0.8050 0.031 Uiso 1 1 calc R . .
C16 C 1.41115(15) 0.33131(17) 0.72267(5) 0.0323(3) Uani 1 1 d . . .
H16 H 1.5039 0.2476 0.7184 0.039 Uiso 1 1 calc R . .
C11 C 0.84228(14) 0.39629(14) 0.65543(4) 0.0246(2) Uani 1 1 d . . .
H11A H 0.8101 0.4137 0.6887 0.037 Uiso 1 1 calc R . .
H11B H 0.9624 0.3533 0.6568 0.037 Uiso 1 1 calc R . .
H11C H 0.7665 0.3014 0.6385 0.037 Uiso 1 1 calc R . .
O2 O 0.64860(10) 0.92330(12) 0.56437(3) 0.0319(2) Uani 1 1 d . . .
C2 C 0.68616(14) 1.24087(16) 0.51459(4) 0.0272(2) Uani 1 1 d . . .
H2A H 0.6027 1.2802 0.5376 0.033 Uiso 1 1 calc R . .
H2B H 0.6269 1.1543 0.4901 0.033 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
O1 C3 1.3312(12) . ?
O1 C2 1.4571(11) . ?
O3 C10 1.3183(12) . ?
C4 C8 1.3959(13) . ?
C4 C3 1.4429(13) . ?
C4 C5 1.4779(12) . ?
C8 C7 1.4232(13) . ?
C8 C9 1.4972(13) . ?
C6 C7 1.3751(14) . ?
C6 C5 1.4532(13) . ?
C6 C12 1.4808(12) . ?
C12 C17 1.3922(14) . ?
C12 C13 1.3979(14) . ?
C10 C5 1.3838(13) . ?
C10 C11 1.4986(13) . ?
C3 O2 1.2423(13) . ?
C13 C14 1.3873(13) . ?
C17 C16 1.3944(15) . ?
C15 C16 1.3852(18) . ?
C15 C14 1.3862(16) . ?
C1 C2 1.5011(15) . ?

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
C3 O1 C2 116.28(8) . . ?
C8 C4 C3 124.98(9) . . ?
C8 C4 C5 107.91(8) . . ?
C3 C4 C5 127.00(9) . . ?
C4 C8 C7 107.91(9) . . ?
C4 C8 C9 129.67(9) . . ?
C7 C8 C9 122.40(9) . . ?
C7 C6 C5 108.05(8) . . ?
C7 C6 C12 122.78(9) . . ?
C5 C6 C12 128.81(9) . . ?
C17 C12 C13 118.89(9) . . ?
C17 C12 C6 121.28(9) . . ?
C13 C12 C6 119.73(9) . . ?
O3 C10 C5 123.80(9) . . ?
O3 C10 C11 110.50(8) . . ?
C5 C10 C11 125.70(9) . . ?
O2 C3 O1 119.80(8) . . ?
O2 C3 C4 125.33(9) . . ?
O1 C3 C4 114.85(8) . . ?
C6 C7 C8 110.48(9) . . ?
C10 C5 C6 125.37(8) . . ?
C10 C5 C4 128.90(9) . . ?
C6 C5 C4 105.55(8) . . ?
C14 C13 C12 120.64(9) . . ?
C16 C17 C12 120.17(10) . . ?
C16 C15 C14 119.64(9) . . ?
C13 C14 C15 120.18(10) . . ?
C15 C16 C17 120.46(10) . . ?
O1 C2 C1 107.14(8) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.78
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_csh_03_4106
_database_code_depnum_ccdc_archive 'CCDC 1500488'
_audit_update_record             
;
2016-08-22 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H34 Br2 O6'
_chemical_formula_weight         698.43

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'
O O 0.0106 0.0060 '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           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   7.5076(6)
_cell_length_b                   7.9269(6)
_cell_length_c                   13.2339(10)
_cell_angle_alpha                94.761(4)
_cell_angle_beta                 94.576(4)
_cell_angle_gamma                98.120(4)
_cell_volume                     773.64(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    150
_cell_measurement_reflns_used    5786
_cell_measurement_theta_min      2.6075
_cell_measurement_theta_max      28.6835

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    2.664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6752
_exptl_absorpt_correction_T_max  0.7405
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150
_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 APEX-II CCD'
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9113
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0510
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         28.28
_reflns_number_total             5920
_reflns_number_gt                5410
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.1000P)²+0.1400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.279(19)
_refine_ls_number_reflns         5920
_refine_ls_number_parameters     385
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   0.763
_refine_ls_restrained_S_all      0.762
_refine_ls_shift/su_max          0.150
_refine_ls_shift/su_mean         0.028

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 -0.19444(3) 0.55887(3) -0.437047(18) 0.03049(13) Uani 1 1 d . . .
Br2 Br 0.85051(3) 0.30120(3) 1.317314(18) 0.03041(13) Uani 1 1 d . . .
C1 C -0.1361(6) 0.5906(7) -0.2930(4) 0.0226(10) Uani 1 1 d . . .
C2 C -0.2392(5) 0.6872(6) -0.2322(4) 0.0253(11) Uani 1 1 d . . .
H2 H -0.3339 0.7353 -0.2622 0.030 Uiso 1 1 calc R . .
C4 C -0.0549(5) 0.6374(5) -0.0847(3) 0.0148(8) Uani 1 1 d . . .
C5 C 0.0427(6) 0.5441(6) -0.1464(4) 0.0210(10) Uani 1 1 d . . .
H5 H 0.1382 0.4971 -0.1164 0.025 Uiso 1 1 calc R . .
C6 C 0.0053(6) 0.5181(6) -0.2489(4) 0.0233(10) Uani 1 1 d . . .
H6 H 0.0726 0.4534 -0.2886 0.028 Uiso 1 1 calc R . .
C3 C -0.1992(6) 0.7088(7) -0.1310(4) 0.0251(11) Uani 1 1 d . . .
H3 H -0.2673 0.7717 -0.0907 0.030 Uiso 1 1 calc R . .
C11 C 0.1574(5) 0.6229(6) 0.0833(4) 0.0176(9) Uani 1 1 d . . .
H11 H 0.1644 0.5004 0.0716 0.021 Uiso 1 1 calc R . .
C8 C -0.1170(5) 0.7219(6) 0.0974(4) 0.0207(10) Uani 1 1 d . . .
H8 H -0.2294 0.7554 0.0832 0.025 Uiso 1 1 calc R . .
C7 C -0.0143(5) 0.6638(6) 0.0245(4) 0.0168(9) Uani 1 1 d . . .
C10 C 0.1322(6) 0.6672(6) 0.1912(3) 0.0180(9) Uani 1 1 d . . .
C9 C -0.0296(6) 0.7247(6) 0.1989(4) 0.0200(9) Uani 1 1 d . . .
O1 O 0.4221(4) 0.6647(5) -0.0077(3) 0.0243(7) Uani 1 1 d . . .
C12 C 0.3282(6) 0.7300(7) 0.0461(4) 0.0211(9) Uani 1 1 d . . .
C14 C -0.1136(6) 0.7816(8) 0.2919(4) 0.0282(11) Uani 1 1 d . . .
H14A H -0.0619 0.7339 0.3497 0.042 Uiso 1 1 calc R . .
H14B H -0.2415 0.7433 0.2828 0.042 Uiso 1 1 calc R . .
H14C H -0.0914 0.9043 0.3030 0.042 Uiso 1 1 calc R . .
C15 C 0.2767(6) 0.6538(6) 0.2673(3) 0.0178(9) Uani 1 1 d . . .
C17 C 0.3187(9) 0.7045(12) 0.5437(5) 0.0465(18) Uani 1 1 d . . .
H17A H 0.2410 0.6031 0.5566 0.070 Uiso 1 1 calc R . .
H17B H 0.2514 0.7989 0.5436 0.070 Uiso 1 1 calc R . .
H17C H 0.4175 0.7294 0.5959 0.070 Uiso 1 1 calc R . .
C16 C 0.3913(6) 0.6763(9) 0.4410(4) 0.0326(13) Uani 1 1 d . . .
H16A H 0.4324 0.5657 0.4336 0.039 Uiso 1 1 calc R . .
H16B H 0.4920 0.7646 0.4342 0.039 Uiso 1 1 calc R . .
C13 C 0.3614(7) 0.9215(6) 0.0818(5) 0.0268(12) Uani 1 1 d . . .
H13A H 0.4061 0.9847 0.0279 0.040 Uiso 1 1 calc R . .
H13B H 0.4488 0.9424 0.1401 0.040 Uiso 1 1 calc R . .
H13C H 0.2502 0.9574 0.0996 0.040 Uiso 1 1 calc R . .
O2 O 0.4240(5) 0.6181(6) 0.2464(3) 0.0361(10) Uani 1 1 d . . .
O3 O 0.2435(4) 0.6836(5) 0.3644(3) 0.0291(9) Uani 1 1 d . . .
C18 C 0.7952(6) 0.2693(6) 1.1743(4) 0.0203(10) Uani 1 1 d . . .
C19 C 0.8973(6) 0.1763(7) 1.1167(3) 0.0256(11) Uani 1 1 d . . .
H19 H 0.9927 0.1301 1.1475 0.031 Uiso 1 1 calc R . .
C21 C 0.7137(5) 0.2217(6) 0.9628(4) 0.0197(9) Uani 1 1 d . . .
C22 C 0.6134(6) 0.3200(6) 1.0250(4) 0.0188(9) Uani 1 1 d . . .
H22 H 0.5200 0.3701 0.9953 0.023 Uiso 1 1 calc R . .
C23 C 0.6545(6) 0.3425(6) 1.1318(4) 0.0206(10) Uani 1 1 d . . .
H23 H 0.5877 0.4056 1.1728 0.025 Uiso 1 1 calc R . .
C20 C 0.8562(6) 0.1513(7) 1.0102(3) 0.0219(10) Uani 1 1 d . . .
H20 H 0.9246 0.0873 0.9708 0.026 Uiso 1 1 calc R . .
C24 C 0.6708(6) 0.1971(6) 0.8514(3) 0.0187(9) Uani 1 1 d . . .
C28 C 0.4955(6) 0.2357(6) 0.8007(3) 0.0169(9) Uani 1 1 d . . .
H28 H 0.4876 0.3578 0.8137 0.020 Uiso 1 1 calc R . .
C25 C 0.7732(6) 0.1406(7) 0.7828(3) 0.0202(10) Uani 1 1 d . . .
H25 H 0.8858 0.1081 0.7982 0.024 Uiso 1 1 calc R . .
C27 C 0.5230(6) 0.1927(6) 0.6888(4) 0.0191(9) Uani 1 1 d . . .
C26 C 0.6855(5) 0.1359(6) 0.6793(4) 0.0200(9) Uani 1 1 d . . .
C29 C 0.7739(6) 0.0792(7) 0.5891(4) 0.0246(10) Uani 1 1 d . . .
H29A H 0.6902 0.0695 0.5294 0.037 Uiso 1 1 calc R . .
H29B H 0.8112 -0.0300 0.5979 0.037 Uiso 1 1 calc R . .
H29C H 0.8777 0.1614 0.5815 0.037 Uiso 1 1 calc R . .
O4 O 0.2317(4) 0.1930(5) 0.8910(3) 0.0330(9) Uani 1 1 d . . .
C30 C 0.3310(6) 0.1300(6) 0.8337(4) 0.0178(8) Uani 1 1 d . . .
C32 C 0.3748(6) 0.2098(7) 0.6101(4) 0.0266(11) Uani 1 1 d . . .
C34 C 0.3349(9) 0.1466(10) 0.3389(5) 0.0387(14) Uani 1 1 d . . .
H34A H 0.3684 0.0340 0.3312 0.058 Uiso 1 1 calc R . .
H34B H 0.4389 0.2304 0.3346 0.058 Uiso 1 1 calc R . .
H34C H 0.2433 0.1569 0.2857 0.058 Uiso 1 1 calc R . .
C33 C 0.2645(7) 0.1747(8) 0.4385(4) 0.0296(11) Uani 1 1 d . . .
H33A H 0.2207 0.2841 0.4449 0.035 Uiso 1 1 calc R . .
H33B H 0.1655 0.0851 0.4460 0.035 Uiso 1 1 calc R . .
C31 C 0.2929(8) -0.0519(8) 0.7984(5) 0.0337(13) Uani 1 1 d . . .
H31A H 0.2606 -0.0655 0.7262 0.051 Uiso 1 1 calc R . .
H31B H 0.1947 -0.1055 0.8323 0.051 Uiso 1 1 calc R . .
H31C H 0.3983 -0.1044 0.8135 0.051 Uiso 1 1 calc R . .
O5 O 0.2321(5) 0.2454(6) 0.6348(3) 0.0336(10) Uani 1 1 d . . .
O6 O 0.4141(4) 0.1720(5) 0.5161(3) 0.0252(8) 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
Br1 C1 1.909(5) . ?
Br2 C18 1.894(5) . ?
C1 C2 1.413(7) . ?
C1 C6 1.389(7) . ?
C2 C3 1.341(8) . ?
C4 C3 1.412(7) . ?
C4 C5 1.378(7) . ?
C4 C7 1.444(6) . ?
C5 C6 1.356(8) . ?
C11 C10 1.475(7) . ?
C11 C7 1.540(6) . ?
C11 C12 1.572(6) . ?
C8 C7 1.372(7) . ?
C8 C9 1.445(7) . ?
C10 C9 1.364(6) . ?
C10 C15 1.442(6) . ?
C9 C14 1.492(7) . ?
O1 C12 1.180(6) . ?
C12 C13 1.531(7) . ?
C15 O2 1.226(6) . ?
C15 O3 1.338(6) . ?
C17 C16 1.515(9) . ?
C16 O3 1.453(6) . ?
C18 C23 1.378(7) . ?
C18 C19 1.368(7) . ?
C19 C20 1.410(6) . ?
C21 C22 1.418(7) . ?
C21 C20 1.403(7) . ?
C21 C24 1.474(6) . ?
C22 C23 1.413(7) . ?
C24 C25 1.326(7) . ?
C24 C28 1.511(5) . ?
C28 C27 1.529(7) . ?
C28 C30 1.507(6) . ?
C25 C26 1.466(6) . ?
C27 C26 1.370(6) . ?
C27 C32 1.491(6) . ?
C26 C29 1.480(7) . ?
O4 C30 1.230(6) . ?
C30 C31 1.459(8) . ?
C32 O5 1.209(6) . ?
C32 O6 1.321(7) . ?
C34 C33 1.470(9) . ?
C33 O6 1.464(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
C2 C1 C6 120.7(5) . . ?
C2 C1 Br1 119.3(4) . . ?
C6 C1 Br1 120.1(4) . . ?
C1 C2 C3 119.4(4) . . ?
C3 C4 C5 118.2(4) . . ?
C3 C4 C7 119.6(4) . . ?
C5 C4 C7 122.2(4) . . ?
C6 C5 C4 122.7(4) . . ?
C5 C6 C1 118.2(5) . . ?
C2 C3 C4 120.8(5) . . ?
C10 C11 C7 104.3(4) . . ?
C10 C11 C12 113.6(4) . . ?
C7 C11 C12 109.3(4) . . ?
C7 C8 C9 111.9(4) . . ?
C8 C7 C4 129.2(4) . . ?
C8 C7 C11 105.5(4) . . ?
C4 C7 C11 125.3(4) . . ?
C9 C10 C11 110.1(4) . . ?
C9 C10 C15 131.3(5) . . ?
C11 C10 C15 118.4(4) . . ?
C10 C9 C14 129.3(5) . . ?
C10 C9 C8 108.1(4) . . ?
C14 C9 C8 122.6(4) . . ?
O1 C12 C13 122.9(5) . . ?
O1 C12 C11 121.0(5) . . ?
C13 C12 C11 116.2(4) . . ?
O2 C15 O3 120.4(4) . . ?
O2 C15 C10 123.2(4) . . ?
O3 C15 C10 116.5(4) . . ?
C17 C16 O3 106.7(4) . . ?
C15 O3 C16 116.5(4) . . ?
C23 C18 C19 122.4(5) . . ?
C23 C18 Br2 118.7(4) . . ?
C19 C18 Br2 118.9(3) . . ?
C20 C19 C18 119.2(4) . . ?
C22 C21 C20 118.1(5) . . ?
C22 C21 C24 120.7(4) . . ?
C20 C21 C24 121.2(5) . . ?
C21 C22 C23 120.4(4) . . ?
C18 C23 C22 118.9(5) . . ?
C19 C20 C21 121.0(5) . . ?
C25 C24 C21 127.0(4) . . ?
C25 C24 C28 110.8(4) . . ?
C21 C24 C28 122.2(4) . . ?
C27 C28 C24 100.5(3) . . ?
C27 C28 C30 112.8(4) . . ?
C24 C28 C30 113.2(4) . . ?
C24 C25 C26 111.1(4) . . ?
C26 C27 C32 130.6(5) . . ?
C26 C27 C28 111.0(4) . . ?
C32 C27 C28 118.4(4) . . ?
C27 C26 C25 106.6(4) . . ?
C27 C26 C29 131.9(4) . . ?
C25 C26 C29 121.4(4) . . ?
O4 C30 C31 119.8(5) . . ?
O4 C30 C28 121.4(5) . . ?
C31 C30 C28 118.7(4) . . ?
O5 C32 O6 126.2(4) . . ?
O5 C32 C27 120.5(5) . . ?
O6 C32 C27 113.2(4) . . ?
O6 C33 C34 107.0(4) . . ?
C32 O6 C33 113.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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_lky_iii_22801
_database_code_depnum_ccdc_archive 'CCDC 1500489'
_audit_update_record             
;
2016-08-22 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 Br2'
_chemical_formula_weight         299.99

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   P2(1)

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

_cell_length_a                   4.3644(3)
_cell_length_b                   15.4436(10)
_cell_length_c                   7.8210(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.674(5)
_cell_angle_gamma                90.00
_cell_volume                     519.66(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    3673
_cell_measurement_theta_min      2.6375
_cell_measurement_theta_max      28.321

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    7.748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3361
_exptl_absorpt_correction_T_max  0.4566
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150
_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 APEX-II CCD'
_diffrn_measurement_method       /w
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7121
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         28.27
_reflns_number_total             2531
_reflns_number_gt                2374
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.98(3)
_refine_ls_number_reflns         2531
_refine_ls_number_parameters     118
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1405
_refine_ls_goodness_of_fit_ref   0.671
_refine_ls_restrained_S_all      0.671
_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 -0.00100(16) 0.70074(3) 1.05877(10) 0.0400(2) Uani 1 1 d . . .
Br2 Br 0.38175(12) 0.30289(4) 0.61278(7) 0.02799(18) Uani 1 1 d . . .
C1 C 0.0739(14) 0.6308(4) 0.8696(9) 0.0306(13) Uani 1 1 d . . .
C2 C 0.2312(17) 0.6645(5) 0.7457(10) 0.0359(14) Uani 1 1 d . . .
H2 H 0.3023 0.7214 0.7525 0.043 Uiso 1 1 calc R . .
C3 C 0.2799(16) 0.6103(4) 0.6100(9) 0.0341(13) Uani 1 1 d . . .
H3 H 0.3853 0.6323 0.5256 0.041 Uiso 1 1 calc R . .
C4 C 0.1778(14) 0.5247(4) 0.5952(7) 0.0246(11) Uani 1 1 d . . .
C5 C 0.2376(13) 0.4681(4) 0.4518(8) 0.0243(11) Uani 1 1 d . . .
C6 C 0.3972(14) 0.4946(4) 0.3275(8) 0.0299(12) Uani 1 1 d . . .
H6 H 0.4668 0.5516 0.3318 0.036 Uiso 1 1 calc R . .
C7 C 0.4657(16) 0.4420(5) 0.1923(8) 0.0334(13) Uani 1 1 d . . .
C8 C 0.5227(17) 0.3959(5) 0.0786(9) 0.0396(15) Uani 1 1 d . . .
H8 H 0.5670 0.3600 -0.0096 0.048 Uiso 1 1 calc R . .
C9 C 0.1210(13) 0.3780(4) 0.4434(8) 0.0277(11) Uani 1 1 d . . .
H9A H 0.1185 0.3553 0.3275 0.033 Uiso 1 1 calc R . .
H9B H -0.0906 0.3774 0.4664 0.033 Uiso 1 1 calc R . .
C10 C 0.0187(16) 0.4945(4) 0.7232(9) 0.0330(13) Uani 1 1 d . . .
H10 H -0.0565 0.4381 0.7157 0.040 Uiso 1 1 calc R . .
C11 C -0.0323(16) 0.5459(5) 0.8624(9) 0.0361(14) Uani 1 1 d . . .
H11 H -0.1347 0.5239 0.9481 0.043 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 1.904(6) . ?
Br2 C9 1.972(6) . ?
C1 C2 1.380(10) . ?
C1 C11 1.388(9) . ?
C2 C3 1.396(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(9) . ?
C3 H3 0.9300 . ?
C4 C10 1.391(9) . ?
C4 C5 1.479(8) . ?
C5 C6 1.351(9) . ?
C5 C9 1.480(8) . ?
C6 C7 1.405(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.198(11) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.395(9) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

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 C11 122.0(6) . . ?
C2 C1 Br1 120.1(5) . . ?
C11 C1 Br1 117.9(5) . . ?
C1 C2 C3 117.7(6) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 123.0(6) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C3 C4 C10 116.7(6) . . ?
C3 C4 C5 121.9(5) . . ?
C10 C4 C5 121.4(5) . . ?
C6 C5 C9 117.9(6) . . ?
C6 C5 C4 123.0(5) . . ?
C9 C5 C4 119.1(5) . . ?
C5 C6 C7 124.6(6) . . ?
C5 C6 H6 117.7 . . ?
C7 C6 H6 117.7 . . ?
C8 C7 C6 178.8(7) . . ?
C7 C8 H8 180.0 . . ?
C5 C9 Br2 111.6(4) . . ?
C5 C9 H9A 109.3 . . ?
Br2 C9 H9A 109.3 . . ?
C5 C9 H9B 109.3 . . ?
Br2 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C4 122.4(6) . . ?
C11 C10 H10 118.8 . . ?
C4 C10 H10 118.8 . . ?
C1 C11 C10 118.2(6) . . ?
C1 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.103
