# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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. 
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#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1574456'
_audit_update_record             
;
2017-09-14 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;
_audit_creation_date             2017-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H27 Br O3'
_chemical_formula_sum            'C26 H27 Br O3'
_chemical_formula_weight         467.38
_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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   14.839(4)
_cell_length_b                   17.596(4)
_cell_length_c                   8.652(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2259.2(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7046
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4661
_cell_measurement_theta_min      2.3149
_shelx_estimated_absorpt_T_max   0.820
_shelx_estimated_absorpt_T_min   0.587
_exptl_absorpt_coefficient_mu    1.844
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.72002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.112
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15380
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.458
_diffrn_reflns_theta_min         2.745
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4673
_reflns_number_total             5155
_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  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 1521 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0162P)²+0.8236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0877
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C15(H15), C16(H16), C18(H18), C23(H23), C24(H24),
 C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.47613(3) 0.29058(3) 0.13965(6) 0.04757(15) Uani 1 1 d . . . . .
O1 O 0.39601(19) 0.59781(19) 0.3925(4) 0.0399(8) Uani 1 1 d . . . . .
H1 H 0.452361 0.601671 0.387785 0.060 Uiso 1 1 calc GR . . . .
O2 O 0.26861(18) 0.43798(15) 0.3209(3) 0.0267(6) Uani 1 1 d . . . . .
O3 O 0.40844(19) 0.40433(19) 0.4001(4) 0.0382(8) Uani 1 1 d . . . . .
C1 C 0.2154(3) 0.5777(2) 0.4599(5) 0.0232(8) Uani 1 1 d . . . . .
H1A H 0.253535 0.565472 0.367934 0.028 Uiso 1 1 calc R . . . .
C2 C 0.2746(3) 0.6304(2) 0.5577(5) 0.0250(9) Uani 1 1 d . . . . .
C3 C 0.3644(3) 0.6397(2) 0.5154(5) 0.0269(9) Uani 1 1 d . . . . .
C4 C 0.4203(3) 0.6894(2) 0.5945(5) 0.0306(10) Uani 1 1 d . . . . .
H4 H 0.480327 0.697621 0.559994 0.037 Uiso 1 1 calc R . . . .
C5 C 0.3883(3) 0.7270(2) 0.7242(5) 0.0301(10) Uani 1 1 d . . . . .
H5 H 0.426955 0.760650 0.778733 0.036 Uiso 1 1 calc R . . . .
C6 C 0.3011(3) 0.7162(2) 0.7753(5) 0.0285(9) Uani 1 1 d . . . . .
C7 C 0.2452(3) 0.6690(2) 0.6883(5) 0.0272(9) Uani 1 1 d . . . . .
H7 H 0.184313 0.662926 0.719906 0.033 Uiso 1 1 calc R . . . .
C8 C 0.2689(3) 0.7532(3) 0.9232(5) 0.0428(12) Uani 1 1 d . . . . .
H8A H 0.311934 0.742646 1.006389 0.064 Uiso 1 1 calc GR . . . .
H8B H 0.209696 0.732709 0.951100 0.064 Uiso 1 1 calc GR . . . .
H8C H 0.264189 0.808266 0.907920 0.064 Uiso 1 1 calc GR . . . .
C9 C 0.1273(3) 0.6131(2) 0.3891(5) 0.0271(9) Uani 1 1 d . . . . .
C10 C 0.0993(3) 0.5620(3) 0.2538(5) 0.0371(11) Uani 1 1 d . . . . .
H10A H 0.148032 0.560283 0.177413 0.056 Uiso 1 1 calc GR . . . .
H10B H 0.044769 0.582601 0.205446 0.056 Uiso 1 1 calc GR . . . .
H10C H 0.087181 0.510592 0.291895 0.056 Uiso 1 1 calc GR . . . .
C11 C 0.0471(3) 0.6203(3) 0.4985(5) 0.0359(11) Uani 1 1 d . . . . .
H11A H 0.032792 0.570411 0.542350 0.054 Uiso 1 1 calc GR . . . .
H11B H -0.005191 0.639556 0.441391 0.054 Uiso 1 1 calc GR . . . .
H11C H 0.062119 0.655719 0.582116 0.054 Uiso 1 1 calc GR . . . .
C12 C 0.1505(3) 0.6917(2) 0.3236(5) 0.0413(12) Uani 1 1 d . . . . .
H12A H 0.158271 0.727791 0.408825 0.062 Uiso 1 1 calc GR . . . .
H12B H 0.101452 0.708981 0.256343 0.062 Uiso 1 1 calc GR . . . .
H12C H 0.206438 0.688509 0.263897 0.062 Uiso 1 1 calc GR . . . .
C13 C 0.2016(3) 0.5012(2) 0.5399(5) 0.0234(8) Uani 1 1 d . . . . .
C14 C 0.2315(3) 0.4340(2) 0.4721(5) 0.0243(9) Uani 1 1 d . . . . .
C15 C 0.2186(3) 0.3634(2) 0.5386(5) 0.0297(10) Uani 1 1 d . . . . .
H15 H 0.239097 0.318894 0.487617 0.036 Uiso 1 1 calc R . . . .
C16 C 0.1756(3) 0.3581(2) 0.6796(5) 0.0314(10) Uani 1 1 d . . . . .
H16 H 0.166260 0.309689 0.725491 0.038 Uiso 1 1 calc R . . . .
C17 C 0.1461(3) 0.4232(2) 0.7548(5) 0.0286(9) Uani 1 1 d . . . . .
C18 C 0.1600(3) 0.4931(2) 0.6837(5) 0.0272(9) Uani 1 1 d . . . . .
H18 H 0.140214 0.537689 0.735571 0.033 Uiso 1 1 calc R . . . .
C19 C 0.1001(3) 0.4188(3) 0.9096(5) 0.0424(12) Uani 1 1 d . . . . .
H19A H 0.065298 0.371561 0.916034 0.064 Uiso 1 1 calc GR . . . .
H19B H 0.059610 0.462337 0.921880 0.064 Uiso 1 1 calc GR . . . .
H19C H 0.145570 0.419519 0.991832 0.064 Uiso 1 1 calc GR . . . .
C20 C 0.3568(3) 0.4230(2) 0.2988(5) 0.0283(9) Uani 1 1 d . . . . .
C21 C 0.3783(3) 0.4326(2) 0.1321(5) 0.0287(9) Uani 1 1 d . . . . .
C22 C 0.4259(3) 0.3792(2) 0.0455(5) 0.0335(10) Uani 1 1 d . . . . .
C23 C 0.4357(3) 0.3870(3) -0.1117(6) 0.0431(12) Uani 1 1 d . . . . .
H23 H 0.466096 0.348858 -0.169250 0.052 Uiso 1 1 calc R . . . .
C24 C 0.4018(3) 0.4498(3) -0.1858(6) 0.0470(13) Uani 1 1 d . . . . .
H24 H 0.408502 0.454890 -0.294462 0.056 Uiso 1 1 calc R . . . .
C25 C 0.3580(3) 0.5055(3) -0.1029(5) 0.0407(12) Uani 1 1 d . . . . .
H25 H 0.336774 0.549777 -0.153937 0.049 Uiso 1 1 calc R . . . .
C26 C 0.3450(3) 0.4970(3) 0.0542(5) 0.0342(10) Uani 1 1 d . . . . .
H26 H 0.313286 0.534970 0.110224 0.041 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 C22 1.911(4) . ?
O1 H1 0.8400 . ?
O1 C3 1.376(5) . ?
O2 C14 1.421(5) . ?
O2 C20 1.348(5) . ?
O3 C20 1.210(5) . ?
C1 H1A 1.0000 . ?
C1 C2 1.532(5) . ?
C1 C9 1.572(5) . ?
C1 C13 1.529(5) . ?
C2 C3 1.391(6) . ?
C2 C7 1.389(6) . ?
C3 C4 1.386(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(6) . ?
C6 C7 1.395(6) . ?
C6 C8 1.513(6) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.533(6) . ?
C9 C11 1.526(6) . ?
C9 C12 1.534(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.392(5) . ?
C13 C18 1.396(6) . ?
C14 C15 1.382(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(6) . ?
C17 C18 1.391(6) . ?
C17 C19 1.505(6) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.487(6) . ?
C21 C22 1.395(6) . ?
C21 C26 1.407(6) . ?
C22 C23 1.374(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.373(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.376(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.382(6) . ?
C26 H26 0.9500 . ?

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 H1 109.5 . . ?
C20 O2 C14 119.8(3) . . ?
C2 C1 H1A 104.2 . . ?
C2 C1 C9 116.9(3) . . ?
C9 C1 H1A 104.2 . . ?
C13 C1 H1A 104.2 . . ?
C13 C1 C2 111.2(3) . . ?
C13 C1 C9 114.4(3) . . ?
C3 C2 C1 118.3(4) . . ?
C7 C2 C1 124.4(4) . . ?
C7 C2 C3 117.2(4) . . ?
O1 C3 C2 117.8(4) . . ?
O1 C3 C4 121.0(4) . . ?
C4 C3 C2 121.2(4) . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.7(4) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 117.8(4) . . ?
C5 C6 C8 120.6(4) . . ?
C7 C6 C8 121.6(4) . . ?
C2 C7 C6 122.9(4) . . ?
C2 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C1 107.0(3) . . ?
C10 C9 C12 107.9(4) . . ?
C11 C9 C1 116.1(3) . . ?
C11 C9 C10 108.2(3) . . ?
C11 C9 C12 109.2(4) . . ?
C12 C9 C1 108.3(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C1 121.0(4) . . ?
C14 C13 C18 115.5(4) . . ?
C18 C13 C1 123.5(4) . . ?
C13 C14 O2 118.0(3) . . ?
C15 C14 O2 118.8(4) . . ?
C15 C14 C13 122.9(4) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(4) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.3(4) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C18 118.4(4) . . ?
C16 C17 C19 121.1(4) . . ?
C18 C17 C19 120.5(4) . . ?
C13 C18 H18 118.3 . . ?
C17 C18 C13 123.3(4) . . ?
C17 C18 H18 118.3 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C20 C21 108.9(3) . . ?
O3 C20 O2 124.4(4) . . ?
O3 C20 C21 126.7(4) . . ?
C22 C21 C20 123.6(4) . . ?
C22 C21 C26 117.6(4) . . ?
C26 C21 C20 118.7(4) . . ?
C21 C22 Br1 121.3(3) . . ?
C23 C22 Br1 117.5(4) . . ?
C23 C22 C21 121.2(4) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.2(5) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.2(5) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.1(5) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 119.7 . . ?
C25 C26 C21 120.6(5) . . ?
C25 C26 H26 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 Br1 0.84 3.05 3.499(3) 115.5 2_665
O1 H1 O3 0.84 2.07 2.903(4) 170.5 2_665

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
