# 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_JP-02-10
_database_code_depnum_ccdc_archive 'CCDC 1437901'
_audit_update_record             
;
2015-11-27 deposited with the CCDC.
2016-03-17 downloaded from the CCDC.
;
_audit_creation_date             2015-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_formula_moiety         'C14 H16 O3'
_chemical_formula_sum            'C14 H16 O3'
_chemical_formula_weight         232.28
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.498(2)
_cell_length_b                   5.9876(8)
_cell_length_c                   14.857(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.208(7)
_cell_angle_gamma                90
_cell_volume                     1255.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2765
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.4
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   Multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.2287
_exptl_crystal_description       Prism
_exptl_crystal_F_000             496.2782
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12978
_diffrn_reflns_theta_full        27.4710
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.54
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.9965
_diffrn_measurement_details      
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.052875
_diffrn_orient_matrix_UB_12      0.021387
_diffrn_orient_matrix_UB_13      0.042028
_diffrn_orient_matrix_UB_21      0.050867
_diffrn_orient_matrix_UB_22      -0.106482
_diffrn_orient_matrix_UB_23      0.118182
_diffrn_orient_matrix_UB_31      0.028046
_diffrn_orient_matrix_UB_32      0.052476
_diffrn_orient_matrix_UB_33      0.035210
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -18
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -11
_reflns_number_gt                2190
_reflns_number_total             2864
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.2179
_refine_diff_density_min         -0.1712
_refine_diff_density_rms         0.0460
_refine_ls_d_res_high            0.7704
_refine_ls_d_res_low             5.7501
_refine_ls_goodness_of_fit_ref   1.0333
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2864
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.0333
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0969P)²+0.1545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1671
_olex2_refinement_description    
;
;
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_refinement_flags_posn
O1 O 0.17765(5) 0.45483(6) 0.36052(5) 0.0527(3) Uani 1.000000 .
O2 O -0.03638(5) 0.36940(6) 0.30638(5) 0.0704(4) Uani 1.000000 .
O3 O -0.02255(5) -0.18289(6) 0.37353(5) 0.0725(4) Uani 1.000000 .
H3 H -0.01643(5) -0.30777(6) 0.35300(5) 0.1088(6) Uiso 1.000000 GR
C4 C 0.23411(5) 0.68733(6) 0.48098(5) 0.0469(3) Uani 1.000000 .
C5 C -0.04371(5) -0.02707(6) 0.29952(5) 0.0500(4) Uani 1.000000 .
C6 C -0.00211(5) 0.19551(6) 0.33994(5) 0.0490(4) Uani 1.000000 .
C7 C 0.17270(6) 0.52410(6) 0.50816(5) 0.0524(4) Uani 1.000000 .
H7 H 0.15752(6) 0.51309(6) 0.56553(5) 0.0629(5) Uiso 1.000000 R
C8 C 0.28846(5) 0.86782(6) 0.52270(5) 0.0542(4) Uani 1.000000 .
H8 H 0.29000(5) 0.90469(6) 0.58384(5) 0.0650(5) Uiso 1.000000 R
C9 C 0.14150(5) 0.39066(6) 0.43465(5) 0.0493(4) Uani 1.000000 .
C10 C 0.33997(5) 0.99143(6) 0.47269(6) 0.0556(4) Uani 1.000000 .
C11 C 0.23397(5) 0.63695(6) 0.39031(5) 0.0477(3) Uani 1.000000 .
C12 C 0.39842(6) 1.18748(6) 0.51630(6) 0.0769(6) Uani 1.000000 .
H12a H 0.41726(6) 1.16576(6) 0.58197(6) 0.1153(9) Uiso 1.000000 GR
H12b H 0.45375(6) 1.20008(6) 0.49141(6) 0.1153(9) Uiso 1.000000 GR
H12c H 0.36153(6) 1.32167(6) 0.50334(6) 0.1153(9) Uiso 1.000000 GR
C13 C 0.00575(6) -0.09282(6) 0.22372(6) 0.0648(5) Uani 1.000000 .
H13a H 0.07261(6) -0.10578(6) 0.24925(6) 0.0971(7) Uiso 1.000000 GR
H13b H -0.01860(6) -0.23356(6) 0.19773(6) 0.0971(7) Uiso 1.000000 GR
H13c H -0.00550(6) 0.01930(6) 0.17628(6) 0.0971(7) Uiso 1.000000 GR
C14 C 0.33674(6) 0.93354(6) 0.38146(6) 0.0613(4) Uani 1.000000 .
H14 H 0.37166(6) 1.01745(6) 0.34832(6) 0.0736(5) Uiso 1.000000 R
C15 C 0.28389(6) 0.75681(6) 0.33821(5) 0.0590(4) Uani 1.000000 .
H15 H 0.28201(6) 0.72032(6) 0.27698(5) 0.0709(5) Uiso 1.000000 R
C16 C 0.08271(6) 0.18629(6) 0.41957(6) 0.0572(4) Uani 1.000000 .
H16a H 0.06115(6) 0.15528(6) 0.47548(6) 0.0686(5) Uiso 1.000000 R
H16b H 0.12230(6) 0.06225(6) 0.40972(6) 0.0686(5) Uiso 1.000000 R
C17 C -0.14920(6) -0.00812(6) 0.26233(6) 0.0814(6) Uani 1.000000 .
H17a H -0.17360(6) -0.14805(6) 0.23549(6) 0.1220(9) Uiso 1.000000 GR
H17b H -0.17900(6) 0.02915(6) 0.31179(6) 0.1220(9) Uiso 1.000000 GR
H17c H -0.16221(6) 0.10659(6) 0.21601(6) 0.1220(9) Uiso 1.000000 GR


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 C9 1.3781(11) . ?
O1 C11 1.3735(7) . ?
O2 C6 1.2109(7) . ?
O3 H3 0.8200 . ?
O3 C5 1.4212(9) . ?
C4 C7 1.4406(9) . ?
C4 C8 1.3964(8) . ?
C4 C11 1.3800(11) . ?
C5 C6 1.5281(7) . ?
C5 C13 1.5186(12) . ?
C5 C17 1.5070(11) . ?
C6 C16 1.5000(10) . ?
C7 H7 0.9300 . ?
C7 C9 1.3454(9) . ?
C8 H8 0.9300 . ?
C8 C10 1.3825(11) . ?
C9 C16 1.4788(8) . ?
C10 C12 1.5050(8) . ?
C10 C14 1.3894(12) . ?
C11 C15 1.3761(11) . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.3765(8) . ?
C15 H15 0.9300 . ?
C16 H16a 0.9700 . ?
C16 H16b 0.9700 . ?
C17 H17a 0.9600 . ?
C17 H17b 0.9600 . ?
C17 H17c 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
C11 O1 C9 105.70(6) . . ?
C5 O3 H3 109.5 . . ?
C8 C4 C7 136.29(8) . . ?
C11 C4 C7 105.20(5) . . ?
C11 C4 C8 118.51(7) . . ?
C6 C5 O3 105.81(6) . . ?
C13 C5 O3 110.40(5) . . ?
C13 C5 C6 107.86(6) . . ?
C17 C5 O3 110.77(6) . . ?
C17 C5 C6 110.78(5) . . ?
C17 C5 C13 111.05(6) . . ?
C5 C6 O2 120.00(6) . . ?
C16 C6 O2 122.80(5) . . ?
C16 C6 C5 117.18(4) . . ?
H7 C7 C4 126.57(4) . . ?
C9 C7 C4 106.86(7) . . ?
C9 C7 H7 126.57(5) . . ?
H8 C8 C4 120.16(5) . . ?
C10 C8 C4 119.67(7) . . ?
C10 C8 H8 120.16(4) . . ?
C7 C9 O1 111.37(6) . . ?
C16 C9 O1 114.89(6) . . ?
C16 C9 C7 133.61(8) . . ?
C12 C10 C8 120.42(7) . . ?
C14 C10 C8 119.27(5) . . ?
C14 C10 C12 120.31(7) . . ?
C4 C11 O1 110.87(6) . . ?
C15 C11 O1 125.67(7) . . ?
C15 C11 C4 123.46(5) . . ?
H12a C12 C10 109.5 . . ?
H12b C12 C10 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C10 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H13a C13 C5 109.5 . . ?
H13b C13 C5 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C5 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H14 C14 C10 118.72(4) . . ?
C15 C14 C10 122.56(7) . . ?
C15 C14 H14 118.72(5) . . ?
C14 C15 C11 116.53(7) . . ?
H15 C15 C11 121.74(4) . . ?
H15 C15 C14 121.74(5) . . ?
C9 C16 C6 115.43(5) . . ?
H16a C16 C6 108.42(5) . . ?
H16a C16 C9 108.42(5) . . ?
H16b C16 C6 108.42(3) . . ?
H16b C16 C9 108.42(4) . . ?
H16b C16 H16a 107.5 . . ?
H17a C17 C5 109.5 . . ?
H17b C17 C5 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 C5 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelx4
_audit_block_doi                 10.5517/cc1kcldx
_database_code_depnum_ccdc_archive 'CCDC 1441109'
_audit_update_record             
;
2015-12-08 deposited with the CCDC.
2016-03-17 downloaded from the CCDC.
;
_audit_creation_date             2015-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_formula_moiety         '2(C14 H15 Br O3)'
_chemical_formula_sum            'C28 H30 Br2 O6'
_chemical_formula_weight         622.35
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28356 2.56002 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.840(2)
_cell_length_b                   11.999(3)
_cell_length_c                   15.345(2)
_cell_angle_alpha                102.86(3)
_cell_angle_beta                 98.09(3)
_cell_angle_gamma                90.08(4)
_cell_volume                     1392.5(6)
_cell_formula_units_Z            2
_exptl_absorpt_coefficient_mu    2.949
_exptl_crystal_density_diffrn    1.4841
_exptl_crystal_F_000             631.2026
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14248
_diffrn_reflns_theta_full        27.6147
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         3.14
_diffrn_measured_fraction_theta_full 0.9643
_diffrn_measured_fraction_theta_max 0.9643
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3651
_reflns_number_total             6248
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.8191
_refine_diff_density_min         -1.2588
_refine_diff_density_rms         0.1728
_refine_ls_d_res_high            0.7667
_refine_ls_d_res_low             6.4955
_refine_ls_goodness_of_fit_ref   1.0101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     330
_refine_ls_number_reflns         6248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0770
_refine_ls_restrained_S_all      1.0101
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1205P)²+2.1670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2032
_refine_ls_wR_factor_ref         0.2399
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21a,H21b), C30(H30a,H30b)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C38(H38), C22(H22), C19(H19), C29(H29), C20(H20)
2.d Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c), C28(H28a,H28b,H28c), C31(H31a,H31b,H31c), C32(H32a,H32b,
 H32c), C34(H34a,H34b,H34c), C37(H37a,H37b,H37c)
;
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_refinement_flags_posn
Br1 Br 0.18059(10) 0.95791(7) 0.41359(4) 0.0645(3) Uani 1.000000 .
Br2 Br 0.34820(11) 0.21004(7) 0.58558(5) 0.0763(3) Uani 1.000000 .
O3 O 0.4810(5) 0.4682(3) 0.7532(3) 0.0467(9) Uani 1.000000 .
O4 O 0.0299(5) 1.1089(3) 0.2470(3) 0.0444(9) Uani 1.000000 .
O5 O 0.7537(5) 0.4095(3) 0.7257(3) 0.0463(9) Uani 1.000000 .
O6 O -0.2423(5) 1.0673(3) 0.2754(3) 0.0476(10) Uani 1.000000 .
O7 O -0.2377(7) 1.3349(4) 0.4230(4) 0.0840(17) Uani 1.000000 .
C8 C 0.0441(7) 0.9145(5) 0.2278(4) 0.0412(12) Uani 1.000000 .
O9 O 0.7333(8) 0.6062(5) 0.5880(4) 0.0822(16) Uani 1.000000 .
C10 C 0.4375(8) 0.3992(5) 0.8073(4) 0.0469(14) Uani 1.000000 .
C11 C 0.0688(7) 1.0093(5) 0.1923(4) 0.0440(13) Uani 1.000000 .
C12 C 0.0746(8) 0.8061(5) 0.1799(4) 0.0514(15) Uani 1.000000 .
C13 C -0.2072(9) 1.2425(5) 0.3805(5) 0.0547(16) Uani 1.000000 .
C14 C -0.0115(7) 0.9572(5) 0.3173(4) 0.0422(13) Uani 1.000000 .
C15 C 0.4623(7) 0.2854(5) 0.7739(4) 0.0409(12) Uani 1.000000 .
C16 C 0.8378(8) 0.5017(5) 0.7017(4) 0.0511(15) Uani 1.000000 .
C17 C 0.5763(7) 0.3989(4) 0.6889(3) 0.0370(11) Uani 1.000000 .
C18 C 0.3676(9) 0.2426(8) 0.9049(5) 0.063(2) Uani 1.000000 .
C19 C 0.4268(8) 0.2044(6) 0.8222(4) 0.0542(16) Uani 1.000000 .
C20 C 0.3747(9) 0.4374(7) 0.8886(5) 0.0629(18) Uani 1.000000 .
C21 C 0.5604(8) 0.4463(5) 0.6047(4) 0.0503(14) Uani 1.000000 .
C22 C 0.1267(9) 0.9986(7) 0.1095(4) 0.0611(18) Uani 1.000000 .
C23 C 0.1299(9) 0.7938(7) 0.0959(5) 0.068(2) Uani 1.000000 .
C24 C -0.0659(7) 1.0794(5) 0.3120(4) 0.0404(12) Uani 1.000000 .
C25 C -0.3575(12) 1.2326(7) 0.2238(6) 0.084(3) Uani 1.000000 .
C26 C 0.7112(8) 0.5306(5) 0.6242(4) 0.0501(14) Uani 1.000000 .
C27 C 0.5257(8) 0.2743(5) 0.6863(4) 0.0417(12) Uani 1.000000 .
C28 C 0.1581(12) 0.6725(8) 0.0420(5) 0.093(3) Uani 1.000000 .
C29 C 0.3419(10) 0.3571(9) 0.9358(5) 0.077(2) Uani 1.000000 .
C30 C -0.0474(8) 1.1767(5) 0.3953(4) 0.0474(14) Uani 1.000000 .
C31 C -0.4974(10) 1.1430(8) 0.3312(8) 0.097(3) Uani 1.000000 .
C32 C 0.3365(12) 0.1562(10) 0.9603(6) 0.098(3) Uani 1.000000 .
C34 C 0.8675(13) 0.6028(7) 0.7810(6) 0.087(3) Uani 1.000000 .
C35 C -0.3303(8) 1.1717(5) 0.3010(5) 0.0558(16) Uani 1.000000 .
C37 C 1.0023(10) 0.4588(9) 0.6670(7) 0.095(3) Uani 1.000000 .
C38 C 0.1560(9) 0.8894(8) 0.0641(5) 0.072(2) Uani 1.000000 .
H12 H 0.0584(8) 0.7424(5) 0.2033(4) 0.0617(18) Uiso 1.000000 R
H38 H 0.1957(9) 0.8801(8) 0.0086(5) 0.086(3) Uiso 1.000000 R
H22 H 0.1448(9) 1.0620(7) 0.0860(4) 0.073(2) Uiso 1.000000 R
H19 H 0.4421(8) 0.1271(6) 0.7997(4) 0.0651(19) Uiso 1.000000 R
H29 H 0.3007(10) 0.3810(9) 0.9906(5) 0.093(3) Uiso 1.000000 R
H20 H 0.3556(9) 0.5144(7) 0.9103(5) 0.075(2) Uiso 1.000000 R
H14 H -0.1097(7) 0.9112(5) 0.3245(4) 0.0506(15) Uiso 1.000000 R
H21a H 0.5689(8) 0.3864(5) 0.5515(4) 0.0603(17) Uiso 1.000000 R
H21b H 0.4520(8) 0.4840(5) 0.5958(4) 0.0603(17) Uiso 1.000000 R
H25a H -0.2480(13) 1.249(5) 0.207(3) 0.126(4) Uiso 1.000000 GR
H25b H -0.428(7) 1.185(3) 0.1728(17) 0.126(4) Uiso 1.000000 GR
H25c H -0.414(8) 1.303(3) 0.2424(17) 0.126(4) Uiso 1.000000 GR
H27 H 0.6275(8) 0.2271(5) 0.6842(4) 0.0501(15) Uiso 1.000000 R
H28a H 0.232(8) 0.633(2) 0.0795(16) 0.140(5) Uiso 1.000000 GR
H28b H 0.0491(16) 0.632(2) 0.023(4) 0.140(5) Uiso 1.000000 GR
H28c H 0.211(8) 0.6774(8) -0.010(3) 0.140(5) Uiso 1.000000 GR
H30a H 0.0554(8) 1.2238(5) 0.3994(4) 0.0569(17) Uiso 1.000000 R
H30b H -0.0427(8) 1.1480(5) 0.4499(4) 0.0569(17) Uiso 1.000000 R
H31a H -0.566(4) 1.090(5) 0.2826(17) 0.145(5) Uiso 1.000000 GR
H31b H -0.4726(10) 1.109(6) 0.382(3) 0.145(5) Uiso 1.000000 GR
H31c H -0.559(5) 1.2117(12) 0.348(5) 0.145(5) Uiso 1.000000 GR
H32a H 0.225(4) 0.120(5) 0.939(3) 0.148(5) Uiso 1.000000 GR
H32b H 0.423(6) 0.100(4) 0.955(4) 0.148(5) Uiso 1.000000 GR
H32c H 0.342(10) 0.1946(13) 1.0226(10) 0.148(5) Uiso 1.000000 GR
H34a H 0.7602(19) 0.623(4) 0.803(3) 0.131(4) Uiso 1.000000 GR
H34b H 0.947(7) 0.583(2) 0.8284(19) 0.131(4) Uiso 1.000000 GR
H34c H 0.914(8) 0.6664(19) 0.7625(13) 0.131(4) Uiso 1.000000 GR
H37a H 1.079(4) 0.438(6) 0.7148(15) 0.143(5) Uiso 1.000000 GR
H37b H 0.9760(15) 0.393(4) 0.618(3) 0.143(5) Uiso 1.000000 GR
H37c H 1.056(5) 0.518(2) 0.646(5) 0.143(5) Uiso 1.000000 GR


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 C14 1.954(6) . ?
Br2 C27 1.945(6) . ?
O3 C10 1.370(7) . ?
O3 C17 1.437(6) . ?
O4 C11 1.361(7) . ?
O4 C24 1.432(7) . ?
O5 C16 1.428(7) . ?
O5 C17 1.420(6) . ?
O6 C24 1.412(7) . ?
O6 C35 1.435(7) . ?
O7 C13 1.197(7) . ?
C8 C11 1.391(8) . ?
C8 C12 1.383(8) . ?
C8 C14 1.482(8) . ?
O9 C26 1.189(8) . ?
C10 C15 1.372(8) . ?
C10 C20 1.388(9) . ?
C11 C22 1.387(9) . ?
C12 C23 1.393(10) . ?
C12 H12 0.9300 . ?
C13 C30 1.499(9) . ?
C13 C35 1.532(9) . ?
C14 C24 1.544(8) . ?
C14 H14 0.9800 . ?
C15 C19 1.395(8) . ?
C15 C27 1.477(8) . ?
C16 C26 1.540(9) . ?
C16 C34 1.506(10) . ?
C16 C37 1.512(10) . ?
C17 C21 1.515(8) . ?
C17 C27 1.536(7) . ?
C18 C19 1.395(10) . ?
C18 C29 1.375(12) . ?
C18 C32 1.519(10) . ?
C19 H19 0.9300 . ?
C20 C29 1.371(12) . ?
C20 H20 0.9300 . ?
C21 C26 1.507(9) . ?
C21 H21a 0.9700 . ?
C21 H21b 0.9700 . ?
C22 C38 1.377(11) . ?
C22 H22 0.9300 . ?
C23 C28 1.539(10) . ?
C23 C38 1.370(12) . ?
C24 C30 1.518(8) . ?
C25 C35 1.515(10) . ?
C25 H25a 0.9600 . ?
C25 H25b 0.9600 . ?
C25 H25c 0.9600 . ?
C27 H27 0.9800 . ?
C28 H28a 0.9600 . ?
C28 H28b 0.9600 . ?
C28 H28c 0.9600 . ?
C29 H29 0.9300 . ?
C30 H30a 0.9700 . ?
C30 H30b 0.9700 . ?
C31 C35 1.513(10) . ?
C31 H31a 0.9600 . ?
C31 H31b 0.9600 . ?
C31 H31c 0.9600 . ?
C32 H32a 0.9600 . ?
C32 H32b 0.9600 . ?
C32 H32c 0.9600 . ?
C34 H34a 0.9600 . ?
C34 H34b 0.9600 . ?
C34 H34c 0.9600 . ?
C37 H37a 0.9600 . ?
C37 H37b 0.9600 . ?
C37 H37c 0.9600 . ?
C38 H38 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
C17 O3 C10 106.2(4) . . ?
C24 O4 C11 107.2(4) . . ?
C17 O5 C16 111.4(4) . . ?
C35 O6 C24 111.6(4) . . ?
C12 C8 C11 120.1(5) . . ?
C14 C8 C11 107.0(5) . . ?
C14 C8 C12 132.8(6) . . ?
C15 C10 O3 113.5(5) . . ?
C20 C10 O3 124.9(6) . . ?
C20 C10 C15 121.6(6) . . ?
C8 C11 O4 112.7(5) . . ?
C22 C11 O4 125.8(6) . . ?
C22 C11 C8 121.5(6) . . ?
C23 C12 C8 119.0(7) . . ?
H12 C12 C8 120.5(4) . . ?
H12 C12 C23 120.5(4) . . ?
C30 C13 O7 126.9(7) . . ?
C35 C13 O7 124.3(6) . . ?
C35 C13 C30 108.8(5) . . ?
C8 C14 Br1 110.3(4) . . ?
C24 C14 Br1 112.0(4) . . ?
C24 C14 C8 101.7(4) . . ?
H14 C14 Br1 110.83(17) . . ?
H14 C14 C8 110.8(3) . . ?
H14 C14 C24 110.8(3) . . ?
C19 C15 C10 120.4(6) . . ?
C27 C15 C10 107.7(5) . . ?
C27 C15 C19 131.9(5) . . ?
C26 C16 O5 104.4(5) . . ?
C34 C16 O5 110.3(6) . . ?
C34 C16 C26 110.7(6) . . ?
C37 C16 O5 108.4(6) . . ?
C37 C16 C26 109.6(6) . . ?
C37 C16 C34 113.1(7) . . ?
O5 C17 O3 108.4(4) . . ?
C21 C17 O3 109.1(4) . . ?
C21 C17 O5 106.3(4) . . ?
C27 C17 O3 105.8(4) . . ?
C27 C17 O5 104.2(4) . . ?
C27 C17 C21 122.4(5) . . ?
C29 C18 C19 119.9(7) . . ?
C32 C18 C19 118.9(8) . . ?
C32 C18 C29 121.3(8) . . ?
C18 C19 C15 118.2(6) . . ?
H19 C19 C15 120.9(4) . . ?
H19 C19 C18 120.9(4) . . ?
C29 C20 C10 117.5(7) . . ?
H20 C20 C10 121.3(4) . . ?
H20 C20 C29 121.3(4) . . ?
C26 C21 C17 103.0(5) . . ?
H21a C21 C17 111.2(3) . . ?
H21a C21 C26 111.2(3) . . ?
H21b C21 C17 111.2(3) . . ?
H21b C21 C26 111.2(3) . . ?
H21b C21 H21a 109.1 . . ?
C38 C22 C11 116.6(7) . . ?
H22 C22 C11 121.7(4) . . ?
H22 C22 C38 121.7(4) . . ?
C28 C23 C12 118.6(8) . . ?
C38 C23 C12 119.1(6) . . ?
C38 C23 C28 122.3(7) . . ?
O6 C24 O4 108.9(4) . . ?
C14 C24 O4 104.7(4) . . ?
C14 C24 O6 104.8(4) . . ?
C30 C24 O4 109.1(4) . . ?
C30 C24 O6 107.3(4) . . ?
C30 C24 C14 121.6(5) . . ?
H25a C25 C35 109.5 . . ?
H25b C25 C35 109.5 . . ?
H25b C25 H25a 109.5 . . ?
H25c C25 C35 109.5 . . ?
H25c C25 H25a 109.5 . . ?
H25c C25 H25b 109.5 . . ?
C16 C26 O9 124.5(6) . . ?
C21 C26 O9 128.0(6) . . ?
C21 C26 C16 107.4(5) . . ?
C15 C27 Br2 111.6(4) . . ?
C17 C27 Br2 112.6(4) . . ?
C17 C27 C15 101.8(4) . . ?
H27 C27 Br2 110.18(17) . . ?
H27 C27 C15 110.2(3) . . ?
H27 C27 C17 110.2(3) . . ?
H28a C28 C23 109.5 . . ?
H28b C28 C23 109.5 . . ?
H28b C28 H28a 109.5 . . ?
H28c C28 C23 109.5 . . ?
H28c C28 H28a 109.5 . . ?
H28c C28 H28b 109.5 . . ?
C20 C29 C18 122.4(6) . . ?
H29 C29 C18 118.8(4) . . ?
H29 C29 C20 118.8(4) . . ?
C24 C30 C13 103.1(5) . . ?
H30a C30 C13 111.1(4) . . ?
H30a C30 C24 111.1(3) . . ?
H30b C30 C13 111.1(4) . . ?
H30b C30 C24 111.1(3) . . ?
H30b C30 H30a 109.1 . . ?
H31a C31 C35 109.5 . . ?
H31b C31 C35 109.5 . . ?
H31b C31 H31a 109.5 . . ?
H31c C31 C35 109.5 . . ?
H31c C31 H31a 109.5 . . ?
H31c C31 H31b 109.5 . . ?
H32a C32 C18 109.5 . . ?
H32b C32 C18 109.5 . . ?
H32b C32 H32a 109.5 . . ?
H32c C32 C18 109.5 . . ?
H32c C32 H32a 109.5 . . ?
H32c C32 H32b 109.5 . . ?
H34a C34 C16 109.5 . . ?
H34b C34 C16 109.5 . . ?
H34b C34 H34a 109.5 . . ?
H34c C34 C16 109.5 . . ?
H34c C34 H34a 109.5 . . ?
H34c C34 H34b 109.5 . . ?
C13 C35 O6 103.9(5) . . ?
C25 C35 O6 110.5(6) . . ?
C25 C35 C13 110.4(6) . . ?
C31 C35 O6 108.1(6) . . ?
C31 C35 C13 110.8(6) . . ?
C31 C35 C25 112.8(7) . . ?
H37a C37 C16 109.5 . . ?
H37b C37 C16 109.5 . . ?
H37b C37 H37a 109.5 . . ?
H37c C37 C16 109.5 . . ?
H37c C37 H37a 109.5 . . ?
H37c C37 H37b 109.5 . . ?
C23 C38 C22 123.6(6) . . ?
H38 C38 C22 118.2(4) . . ?
H38 C38 C23 118.2(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
