# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_50201d_0m
_database_code_depnum_ccdc_archive 'CCDC 1438272'
_audit_update_record             
;
2015-11-21 deposited with the CCDC.
2016-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 Br O'
_chemical_formula_weight         363.24

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.2828(11)
_cell_length_b                   9.4782(12)
_cell_length_c                   10.3493(12)
_cell_angle_alpha                113.833(2)
_cell_angle_beta                 108.559(2)
_cell_angle_gamma                91.384(2)
_cell_volume                     777.26(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3351
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      30.51

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.646
_shelx_estimated_absorpt_T_min   0.504
_shelx_estimated_absorpt_T_max   0.620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.636
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5822
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.305
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3665
_reflns_number_gt                2828
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0312P)²] 
 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         3665
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_restrained_S_all      0.896
_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_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 0.54746(3) 0.31046(3) 0.34581(3) 0.03431(10) Uani 1 1 d . . . . .
O1 O 0.3458(2) -0.38330(19) 0.18898(19) 0.0328(4) Uani 1 1 d . . . . .
C1 C 0.7593(2) 0.1165(3) 0.2617(2) 0.0221(5) Uani 1 1 d . . . . .
C2 C 0.7299(3) 0.2656(3) 0.3021(2) 0.0224(5) Uani 1 1 d . . . . .
C3 C 0.8299(3) 0.3927(3) 0.3146(3) 0.0249(5) Uani 1 1 d . . . . .
C4 C 0.7953(3) 0.5457(3) 0.3540(3) 0.0301(6) Uani 1 1 d . . . . .
H4 H 0.7040 0.5665 0.3714 0.036 Uiso 1 1 calc R U . . .
C5 C 0.8959(3) 0.6642(3) 0.3668(3) 0.0356(6) Uani 1 1 d . . . . .
H5 H 0.8721 0.7644 0.3928 0.043 Uiso 1 1 calc R U . . .
C6 C 1.0321(3) 0.6351(3) 0.3413(3) 0.0352(6) Uani 1 1 d . . . . .
H6 H 1.0996 0.7160 0.3511 0.042 Uiso 1 1 calc R U . . .
C7 C 1.0683(3) 0.4872(3) 0.3016(3) 0.0309(6) Uani 1 1 d . . . . .
H7 H 1.1602 0.4695 0.2847 0.037 Uiso 1 1 calc R U . . .
C8 C 0.9684(3) 0.3616(3) 0.2859(3) 0.0247(5) Uani 1 1 d . . . . .
C9 C 1.0044(3) 0.2047(3) 0.2442(3) 0.0245(5) Uani 1 1 d . . . . .
C10 C 1.1402(3) 0.1679(3) 0.2145(3) 0.0344(6) Uani 1 1 d . . . . .
H10 H 1.2073 0.2453 0.2185 0.041 Uiso 1 1 calc R U . . .
C11 C 1.1756(3) 0.0201(3) 0.1797(3) 0.0380(6) Uani 1 1 d . . . . .
H11 H 1.2667 -0.0011 0.1621 0.046 Uiso 1 1 calc R U . . .
C12 C 1.0754(3) -0.0978(3) 0.1708(3) 0.0371(6) Uani 1 1 d . . . . .
H12 H 1.0999 -0.1975 0.1477 0.045 Uiso 1 1 calc R U . . .
C13 C 0.9420(3) -0.0678(3) 0.1957(3) 0.0266(5) Uani 1 1 d . . . . .
H13 H 0.8755 -0.1481 0.1882 0.032 Uiso 1 1 calc R U . . .
C14 C 0.9013(3) 0.0843(3) 0.2333(2) 0.0222(5) Uani 1 1 d . . . . .
C15 C 0.6499(3) -0.0157(3) 0.2421(3) 0.0229(5) Uani 1 1 d . . . . .
C16 C 0.5602(3) -0.1260(3) 0.0980(3) 0.0261(5) Uani 1 1 d . . . . .
H16 H 0.5686 -0.1163 0.0146 0.031 Uiso 1 1 calc R U . . .
C17 C 0.4574(3) -0.2516(3) 0.0749(3) 0.0261(5) Uani 1 1 d . . . . .
H17 H 0.3979 -0.3244 -0.0228 0.031 Uiso 1 1 calc R U . . .
C18 C 0.4450(3) -0.2664(3) 0.1990(3) 0.0251(5) Uani 1 1 d . . . . .
C19 C 0.5352(3) -0.1577(3) 0.3441(3) 0.0287(6) Uani 1 1 d . . . . .
H19 H 0.5277 -0.1679 0.4275 0.034 Uiso 1 1 calc R U . . .
C20 C 0.6363(3) -0.0341(3) 0.3647(3) 0.0272(5) Uani 1 1 d . . . . .
H20 H 0.6963 0.0380 0.4624 0.033 Uiso 1 1 calc R U . . .
C21 C 0.2534(3) -0.4971(3) 0.0400(3) 0.0381(7) Uani 1 1 d . . . . .
H21A H 0.1893 -0.4460 -0.0140 0.057 Uiso 1 1 calc R U . . .
H21B H 0.1896 -0.5731 0.0468 0.057 Uiso 1 1 calc R U . . .
H21C H 0.3194 -0.5485 -0.0127 0.057 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 C2 1.903(2) . ?
O1 C18 1.372(3) . ?
O1 C21 1.430(3) . ?
C1 C2 1.364(3) . ?
C1 C14 1.453(3) . ?
C1 C15 1.499(3) . ?
C2 C3 1.440(3) . ?
C3 C4 1.414(3) . ?
C3 C8 1.420(3) . ?
C4 C5 1.379(4) . ?
C5 C6 1.384(4) . ?
C6 C7 1.375(4) . ?
C7 C8 1.413(3) . ?
C8 C9 1.452(3) . ?
C9 C10 1.410(3) . ?
C9 C14 1.416(3) . ?
C10 C11 1.375(4) . ?
C11 C12 1.391(4) . ?
C12 C13 1.357(3) . ?
C13 C14 1.427(3) . ?
C15 C16 1.385(3) . ?
C15 C20 1.391(3) . ?
C16 C17 1.398(3) . ?
C17 C18 1.387(3) . ?
C18 C19 1.387(3) . ?
C19 C20 1.384(3) . ?

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
C18 O1 C21 116.72(19) . . ?
C2 C1 C14 118.4(2) . . ?
C2 C1 C15 122.80(19) . . ?
C14 C1 C15 118.79(19) . . ?
C1 C2 C3 123.7(2) . . ?
C1 C2 Br1 118.71(17) . . ?
C3 C2 Br1 117.57(16) . . ?
C4 C3 C8 119.4(2) . . ?
C4 C3 C2 122.6(2) . . ?
C8 C3 C2 118.1(2) . . ?
C5 C4 C3 120.4(2) . . ?
C4 C5 C6 120.5(2) . . ?
C7 C6 C5 120.4(2) . . ?
C6 C7 C8 121.2(2) . . ?
C7 C8 C3 118.1(2) . . ?
C7 C8 C9 122.1(2) . . ?
C3 C8 C9 119.8(2) . . ?
C10 C9 C14 118.5(2) . . ?
C10 C9 C8 121.9(2) . . ?
C14 C9 C8 119.57(19) . . ?
C11 C10 C9 121.4(2) . . ?
C10 C11 C12 120.1(2) . . ?
C13 C12 C11 120.2(2) . . ?
C12 C13 C14 121.5(2) . . ?
C9 C14 C13 118.2(2) . . ?
C9 C14 C1 120.4(2) . . ?
C13 C14 C1 121.4(2) . . ?
C16 C15 C20 118.0(2) . . ?
C16 C15 C1 119.7(2) . . ?
C20 C15 C1 122.3(2) . . ?
C15 C16 C17 121.5(2) . . ?
C18 C17 C16 119.3(2) . . ?
O1 C18 C17 124.0(2) . . ?
O1 C18 C19 116.2(2) . . ?
C17 C18 C19 119.8(2) . . ?
C20 C19 C18 120.0(2) . . ?
C19 C20 C15 121.3(2) . . ?

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
C14 C1 C2 C3 1.6(3) . . . . ?
C15 C1 C2 C3 -177.0(2) . . . . ?
C14 C1 C2 Br1 -178.00(16) . . . . ?
C15 C1 C2 Br1 3.4(3) . . . . ?
C1 C2 C3 C4 178.8(2) . . . . ?
Br1 C2 C3 C4 -1.5(3) . . . . ?
C1 C2 C3 C8 -1.2(4) . . . . ?
Br1 C2 C3 C8 178.42(17) . . . . ?
C8 C3 C4 C5 -1.0(4) . . . . ?
C2 C3 C4 C5 179.0(2) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C3 -0.9(4) . . . . ?
C6 C7 C8 C9 -180.0(2) . . . . ?
C4 C3 C8 C7 1.4(3) . . . . ?
C2 C3 C8 C7 -178.6(2) . . . . ?
C4 C3 C8 C9 -179.5(2) . . . . ?
C2 C3 C8 C9 0.5(3) . . . . ?
C7 C8 C9 C10 -1.0(4) . . . . ?
C3 C8 C9 C10 179.9(2) . . . . ?
C7 C8 C9 C14 178.7(2) . . . . ?
C3 C8 C9 C14 -0.3(3) . . . . ?
C14 C9 C10 C11 -1.8(4) . . . . ?
C8 C9 C10 C11 177.9(2) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C10 C9 C14 C13 1.3(3) . . . . ?
C8 C9 C14 C13 -178.5(2) . . . . ?
C10 C9 C14 C1 -179.5(2) . . . . ?
C8 C9 C14 C1 0.8(3) . . . . ?
C12 C13 C14 C9 0.0(4) . . . . ?
C12 C13 C14 C1 -179.2(2) . . . . ?
C2 C1 C14 C9 -1.4(3) . . . . ?
C15 C1 C14 C9 177.3(2) . . . . ?
C2 C1 C14 C13 177.8(2) . . . . ?
C15 C1 C14 C13 -3.5(3) . . . . ?
C2 C1 C15 C16 104.1(3) . . . . ?
C14 C1 C15 C16 -74.5(3) . . . . ?
C2 C1 C15 C20 -77.1(3) . . . . ?
C14 C1 C15 C20 104.3(3) . . . . ?
C20 C15 C16 C17 0.8(3) . . . . ?
C1 C15 C16 C17 179.6(2) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C21 O1 C18 C17 1.5(3) . . . . ?
C21 O1 C18 C19 -179.3(2) . . . . ?
C16 C17 C18 O1 178.7(2) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
O1 C18 C19 C20 -178.7(2) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C15 0.1(4) . . . . ?
C16 C15 C20 C19 -0.7(3) . . . . ?
C1 C15 C20 C19 -179.6(2) . . . . ?

_refine_diff_density_max         0.473
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.077

_shelxl_version_number           2013-2



