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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1851351'
_audit_update_record             
;
2018-06-25 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 Br O'
_chemical_formula_weight         405.32

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

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.7077(18)
_cell_length_b                   9.7297(13)
_cell_length_c                   18.751(2)
_cell_angle_alpha                90
_cell_angle_beta                 116.691(8)
_cell_angle_gamma                90
_cell_volume                     1908.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9255
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      29.53

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    2.163
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56479
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.334
_diffrn_reflns_theta_max         30.562
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5813
_reflns_number_gt                4087
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0345P)²+1.2740P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5813
_refine_ls_number_parameters     239
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1034
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.005
_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 0.47379(2) 0.81439(3) 0.67443(2) 0.06487(11) Uani 1 1 d . . . . .
O1 O 0.31393(19) 0.08762(18) 0.42277(11) 0.0673(5) Uani 1 1 d D . . . .
C2 C 0.4408(2) 0.1820(2) 0.54980(14) 0.0554(6) Uani 1 1 d . . . . .
H2 H 0.4770 0.0957 0.5667 0.066 Uiso 1 1 calc R U . . .
C3 C 0.19031(17) 0.3437(2) 0.35981(11) 0.0358(4) Uani 1 1 d . . . . .
C4 C 0.07503(17) 0.35935(19) 0.21869(10) 0.0346(4) Uani 1 1 d . . . . .
C6 C 0.29325(18) 0.3285(2) 0.44295(11) 0.0376(4) Uani 1 1 d . . . . .
C7 C 0.05402(17) 0.3590(2) 0.33943(11) 0.0349(4) Uani 1 1 d . . . . .
C9 C 0.46531(19) 0.5356(2) 0.62947(12) 0.0453(5) Uani 1 1 d . . . . .
H9 H 0.5234 0.5230 0.6827 0.054 Uiso 1 1 calc R U . . .
C10 C -0.01504(17) 0.36527(19) 0.25632(11) 0.0350(4) Uani 1 1 d . . . . .
C11 C 0.0465(2) 0.2375(2) 0.16041(12) 0.0454(5) Uani 1 1 d . . . . .
H11B H 0.0562 0.1522 0.1894 0.054 Uiso 1 1 calc R U . . .
H11A H -0.0416 0.2433 0.1198 0.054 Uiso 1 1 calc R U . . .
C14 C 0.3474(2) 0.2022(2) 0.46992(13) 0.0461(5) Uani 1 1 d . . . . .
C16 C -0.14714(19) 0.3751(2) 0.22100(13) 0.0452(5) Uani 1 1 d . . . . .
H16 H -0.1941 0.3771 0.1657 0.054 Uiso 1 1 calc R U . . .
C17 C 0.20189(18) 0.3417(2) 0.29210(11) 0.0389(4) Uani 1 1 d . . . . .
H17 H 0.2794 0.3307 0.2903 0.047 Uiso 1 1 calc R U . . .
C18 C -0.0073(2) 0.3646(2) 0.38763(13) 0.0454(5) Uani 1 1 d . . . . .
H18 H 0.0390 0.3603 0.4429 0.055 Uiso 1 1 calc R U . . .
C20 C 0.1338(3) 0.2347(3) 0.12034(14) 0.0588(6) Uani 1 1 d . . . . .
H20A H 0.1091 0.1594 0.0824 0.071 Uiso 1 1 calc R U . . .
H20B H 0.2210 0.2188 0.1603 0.071 Uiso 1 1 calc R U . . .
C23 C 0.4772(2) 0.2892(2) 0.60147(13) 0.0524(6) Uani 1 1 d . . . . .
H23 H 0.5368 0.2747 0.6542 0.063 Uiso 1 1 calc R U . . .
C24 C 0.2889(2) 0.5775(2) 0.47173(12) 0.0457(5) Uani 1 1 d . . . . .
H24 H 0.2296 0.5929 0.4190 0.055 Uiso 1 1 calc R U . . .
C27 C 0.33419(17) 0.4423(2) 0.49620(10) 0.0361(4) Uani 1 1 d . . . . .
C28 C 0.42670(18) 0.4220(2) 0.57723(11) 0.0401(4) Uani 1 1 d . . . . .
C31 C 0.0710(2) 0.4946(2) 0.17431(12) 0.0433(4) Uani 1 1 d . . . . .
H31A H -0.0161 0.5116 0.1344 0.052 Uiso 1 1 calc R U . . .
H31B H 0.0967 0.5702 0.2121 0.052 Uiso 1 1 calc R U . . .
C34 C -0.2082(2) 0.3820(2) 0.26940(16) 0.0549(6) Uani 1 1 d . . . . .
H34 H -0.2967 0.3902 0.2462 0.066 Uiso 1 1 calc R U . . .
C35 C 0.3299(2) 0.6855(2) 0.52324(13) 0.0502(5) Uani 1 1 d . . . . .
H35 H 0.2994 0.7736 0.5058 0.060 Uiso 1 1 calc R U . . .
C40 C -0.1393(2) 0.3768(3) 0.35177(16) 0.0539(6) Uani 1 1 d . . . . .
H40 H -0.1820 0.3815 0.3832 0.065 Uiso 1 1 calc R U . . .
C41 C 0.41880(19) 0.6624(2) 0.60302(12) 0.0441(5) Uani 1 1 d . . . . .
C42 C 0.1275(3) 0.3686(3) 0.07721(15) 0.0630(7) Uani 1 1 d . . . . .
H42B H 0.0425 0.3798 0.0334 0.076 Uiso 1 1 calc R U . . .
H42A H 0.1881 0.3658 0.0551 0.076 Uiso 1 1 calc R U . . .
C45 C 0.1580(3) 0.4903(3) 0.13384(15) 0.0562(6) Uani 1 1 d . . . . .
H45A H 0.2463 0.4841 0.1742 0.067 Uiso 1 1 calc R U . . .
H45B H 0.1484 0.5748 0.1043 0.067 Uiso 1 1 calc R U . . .
H1A H 0.264(3) 0.116(4) 0.3748(13) 0.107(12) Uiso 1 1 d 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 C41 1.902(2) . ?
O1 C14 1.366(3) . ?
O1 H1A 0.869(18) . ?
C2 C23 1.356(3) . ?
C2 C14 1.417(3) . ?
C2 H2 0.9300 . ?
C3 C17 1.336(3) . ?
C3 C7 1.472(3) . ?
C3 C6 1.489(2) . ?
C4 C10 1.511(3) . ?
C4 C17 1.515(2) . ?
C4 C11 1.544(3) . ?
C4 C31 1.546(3) . ?
C6 C14 1.371(3) . ?
C6 C27 1.422(3) . ?
C7 C18 1.385(3) . ?
C7 C10 1.398(2) . ?
C9 C41 1.350(3) . ?
C9 C28 1.409(3) . ?
C9 H9 0.9300 . ?
C10 C16 1.386(3) . ?
C11 C20 1.517(3) . ?
C11 H11B 0.9700 . ?
C11 H11A 0.9700 . ?
C16 C34 1.386(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C40 1.385(3) . ?
C18 H18 0.9300 . ?
C20 C42 1.518(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C23 C28 1.409(3) . ?
C23 H23 0.9300 . ?
C24 C35 1.361(3) . ?
C24 C27 1.416(3) . ?
C24 H24 0.9300 . ?
C27 C28 1.429(2) . ?
C31 C45 1.520(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C34 C40 1.385(4) . ?
C34 H34 0.9300 . ?
C35 C41 1.404(3) . ?
C35 H35 0.9300 . ?
C40 H40 0.9300 . ?
C42 C45 1.521(4) . ?
C42 H42B 0.9700 . ?
C42 H42A 0.9700 . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?

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
C14 O1 H1A 106(3) . . ?
C23 C2 C14 119.6(2) . . ?
C23 C2 H2 120.2 . . ?
C14 C2 H2 120.2 . . ?
C17 C3 C7 108.40(16) . . ?
C17 C3 C6 127.85(18) . . ?
C7 C3 C6 123.71(17) . . ?
C10 C4 C17 100.66(15) . . ?
C10 C4 C11 112.66(16) . . ?
C17 C4 C11 111.62(16) . . ?
C10 C4 C31 111.09(16) . . ?
C17 C4 C31 111.47(16) . . ?
C11 C4 C31 109.16(15) . . ?
C14 C6 C27 118.98(17) . . ?
C14 C6 C3 119.89(18) . . ?
C27 C6 C3 121.10(17) . . ?
C18 C7 C10 121.06(18) . . ?
C18 C7 C3 130.85(17) . . ?
C10 C7 C3 108.08(16) . . ?
C41 C9 C28 120.70(18) . . ?
C41 C9 H9 119.6 . . ?
C28 C9 H9 119.6 . . ?
C16 C10 C7 119.89(19) . . ?
C16 C10 C4 130.01(17) . . ?
C7 C10 C4 110.10(16) . . ?
C20 C11 C4 112.61(18) . . ?
C20 C11 H11B 109.1 . . ?
C4 C11 H11B 109.1 . . ?
C20 C11 H11A 109.1 . . ?
C4 C11 H11A 109.1 . . ?
H11B C11 H11A 107.8 . . ?
O1 C14 C6 122.82(18) . . ?
O1 C14 C2 115.6(2) . . ?
C6 C14 C2 121.6(2) . . ?
C34 C16 C10 118.9(2) . . ?
C34 C16 H16 120.5 . . ?
C10 C16 H16 120.5 . . ?
C3 C17 C4 112.67(17) . . ?
C3 C17 H17 123.7 . . ?
C4 C17 H17 123.7 . . ?
C7 C18 C40 118.6(2) . . ?
C7 C18 H18 120.7 . . ?
C40 C18 H18 120.7 . . ?
C11 C20 C42 111.5(2) . . ?
C11 C20 H20A 109.3 . . ?
C42 C20 H20A 109.3 . . ?
C11 C20 H20B 109.3 . . ?
C42 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C2 C23 C28 121.59(18) . . ?
C2 C23 H23 119.2 . . ?
C28 C23 H23 119.2 . . ?
C35 C24 C27 121.78(18) . . ?
C35 C24 H24 119.1 . . ?
C27 C24 H24 119.1 . . ?
C24 C27 C6 122.48(16) . . ?
C24 C27 C28 117.85(18) . . ?
C6 C27 C28 119.66(18) . . ?
C23 C28 C9 122.52(18) . . ?
C23 C28 C27 118.49(19) . . ?
C9 C28 C27 118.98(19) . . ?
C45 C31 C4 112.31(18) . . ?
C45 C31 H31A 109.1 . . ?
C4 C31 H31A 109.1 . . ?
C45 C31 H31B 109.1 . . ?
C4 C31 H31B 109.1 . . ?
H31A C31 H31B 107.9 . . ?
C40 C34 C16 121.0(2) . . ?
C40 C34 H34 119.5 . . ?
C16 C34 H34 119.5 . . ?
C24 C35 C41 119.3(2) . . ?
C24 C35 H35 120.4 . . ?
C41 C35 H35 120.4 . . ?
C34 C40 C18 120.5(2) . . ?
C34 C40 H40 119.7 . . ?
C18 C40 H40 119.7 . . ?
C9 C41 C35 121.4(2) . . ?
C9 C41 Br1 119.91(15) . . ?
C35 C41 Br1 118.69(17) . . ?
C20 C42 C45 110.85(19) . . ?
C20 C42 H42B 109.5 . . ?
C45 C42 H42B 109.5 . . ?
C20 C42 H42A 109.5 . . ?
C45 C42 H42A 109.5 . . ?
H42B C42 H42A 108.1 . . ?
C31 C45 C42 111.7(2) . . ?
C31 C45 H45A 109.3 . . ?
C42 C45 H45A 109.3 . . ?
C31 C45 H45B 109.3 . . ?
C42 C45 H45B 109.3 . . ?
H45A C45 H45B 107.9 . . ?

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
C17 C3 C6 C14 -73.4(3) . . . . ?
C7 C3 C6 C14 104.3(2) . . . . ?
C17 C3 C6 C27 108.6(2) . . . . ?
C7 C3 C6 C27 -73.8(3) . . . . ?
C17 C3 C7 C18 179.0(2) . . . . ?
C6 C3 C7 C18 0.9(3) . . . . ?
C17 C3 C7 C10 0.3(2) . . . . ?
C6 C3 C7 C10 -177.71(18) . . . . ?
C18 C7 C10 C16 -1.0(3) . . . . ?
C3 C7 C10 C16 177.84(18) . . . . ?
C18 C7 C10 C4 179.12(18) . . . . ?
C3 C7 C10 C4 -2.1(2) . . . . ?
C17 C4 C10 C16 -177.1(2) . . . . ?
C11 C4 C10 C16 -58.1(3) . . . . ?
C31 C4 C10 C16 64.7(3) . . . . ?
C17 C4 C10 C7 2.8(2) . . . . ?
C11 C4 C10 C7 121.77(17) . . . . ?
C31 C4 C10 C7 -115.39(17) . . . . ?
C10 C4 C11 C20 177.86(17) . . . . ?
C17 C4 C11 C20 -69.7(2) . . . . ?
C31 C4 C11 C20 53.9(2) . . . . ?
C27 C6 C14 O1 -179.9(2) . . . . ?
C3 C6 C14 O1 2.1(3) . . . . ?
C27 C6 C14 C2 1.4(3) . . . . ?
C3 C6 C14 C2 -176.7(2) . . . . ?
C23 C2 C14 O1 -178.1(2) . . . . ?
C23 C2 C14 C6 0.7(4) . . . . ?
C7 C10 C16 C34 1.6(3) . . . . ?
C4 C10 C16 C34 -178.6(2) . . . . ?
C7 C3 C17 C4 1.6(2) . . . . ?
C6 C3 C17 C4 179.49(18) . . . . ?
C10 C4 C17 C3 -2.6(2) . . . . ?
C11 C4 C17 C3 -122.40(19) . . . . ?
C31 C4 C17 C3 115.2(2) . . . . ?
C10 C7 C18 C40 -0.1(3) . . . . ?
C3 C7 C18 C40 -178.6(2) . . . . ?
C4 C11 C20 C42 -56.0(3) . . . . ?
C14 C2 C23 C28 -1.7(4) . . . . ?
C35 C24 C27 C6 -179.4(2) . . . . ?
C35 C24 C27 C28 -0.9(3) . . . . ?
C14 C6 C27 C24 176.0(2) . . . . ?
C3 C6 C27 C24 -6.0(3) . . . . ?
C14 C6 C27 C28 -2.5(3) . . . . ?
C3 C6 C27 C28 175.56(18) . . . . ?
C2 C23 C28 C9 -178.5(2) . . . . ?
C2 C23 C28 C27 0.6(3) . . . . ?
C41 C9 C28 C23 177.1(2) . . . . ?
C41 C9 C28 C27 -2.0(3) . . . . ?
C24 C27 C28 C23 -177.0(2) . . . . ?
C6 C27 C28 C23 1.5(3) . . . . ?
C24 C27 C28 C9 2.1(3) . . . . ?
C6 C27 C28 C9 -179.35(18) . . . . ?
C10 C4 C31 C45 -178.43(17) . . . . ?
C17 C4 C31 C45 70.2(2) . . . . ?
C11 C4 C31 C45 -53.6(2) . . . . ?
C10 C16 C34 C40 -1.1(3) . . . . ?
C27 C24 C35 C41 -0.4(4) . . . . ?
C16 C34 C40 C18 0.0(4) . . . . ?
C7 C18 C40 C34 0.6(3) . . . . ?
C28 C9 C41 C35 0.7(3) . . . . ?
C28 C9 C41 Br1 -179.32(15) . . . . ?
C24 C35 C41 C9 0.6(4) . . . . ?
C24 C35 C41 Br1 -179.43(18) . . . . ?
C11 C20 C42 C45 55.7(3) . . . . ?
C4 C31 C45 C42 55.6(3) . . . . ?
C20 C42 C45 C31 -55.6(3) . . . . ?

_refine_diff_density_max         0.712
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_vr3000_a
_database_code_depnum_ccdc_archive 'CCDC 1858026'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 Br O'
_chemical_formula_weight         365.26

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           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                   12.928(3)
_cell_length_b                   16.007(4)
_cell_length_c                   8.3586(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.097(7)
_cell_angle_gamma                90.00
_cell_volume                     1725.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    8132
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.33

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.385
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      299(2)
_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       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            39902
_diffrn_reflns_av_R_equivalents  0.1108
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         27.83
_reflns_number_total             4077
_reflns_number_gt                2496
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0404P)²+0.7980P] 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         4077
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
Br01 Br -0.03124(3) 0.35466(2) 0.09702(4) 0.06909(15) Uani 1 1 d . . .
O1 O 0.30098(19) 0.64152(12) 0.7757(3) 0.0735(7) Uani 1 1 d . . .
H1 H 0.3253 0.6073 0.8410 0.110 Uiso 1 1 calc R . .
C17 C 0.38451(19) 0.41991(14) 0.7528(3) 0.0320(5) Uani 1 1 d . . .
C16 C 0.4172(2) 0.37639(14) 0.8930(3) 0.0342(6) Uani 1 1 d . . .
C11 C 0.28620(19) 0.46273(15) 0.7793(3) 0.0355(6) Uani 1 1 d . . .
C10 C 0.23040(19) 0.51568(16) 0.6545(3) 0.0379(6) Uani 1 1 d . . .
C4 C 0.16867(19) 0.47806(15) 0.5254(3) 0.0350(6) Uani 1 1 d . . .
C5 C 0.1220(2) 0.52910(16) 0.4004(3) 0.0405(6) Uani 1 1 d . . .
C18 C 0.4421(2) 0.41821(16) 0.6198(3) 0.0402(6) Uani 1 1 d . . .
H18 H 0.4199 0.4469 0.5269 0.048 Uiso 1 1 calc R . .
C13A C 0.3388(2) 0.38833(16) 1.0169(3) 0.0405(6) Uani 1 1 d . . .
C12B C 0.2611(2) 0.44569(17) 0.9287(3) 0.0442(7) Uani 1 1 d . . .
H12B H 0.2025 0.4667 0.9731 0.053 Uiso 1 1 calc R . .
C3C C 0.1513(2) 0.39078(16) 0.5173(3) 0.0420(6) Uani 1 1 d . . .
H3C H 0.1806 0.3567 0.5985 0.050 Uiso 1 1 calc R . .
C1D C 0.0481(2) 0.40667(18) 0.2708(3) 0.0450(7) Uani 1 1 d . . .
C6E C 0.0613(2) 0.49066(18) 0.2733(3) 0.0469(7) Uani 1 1 d . . .
H6E H 0.0303 0.5232 0.1911 0.056 Uiso 1 1 calc R . .
C2F C 0.0927(2) 0.35564(17) 0.3933(3) 0.0481(7) Uani 1 1 d . . .
H2F H 0.0823 0.2982 0.3899 0.058 Uiso 1 1 calc R . .
C9G C 0.2426(2) 0.60094(17) 0.6560(4) 0.0484(7) Uani 1 1 d . . .
C21H C 0.5087(2) 0.33141(17) 0.8990(3) 0.0475(7) Uani 1 1 d . . .
H21H H 0.5310 0.3022 0.9912 0.057 Uiso 1 1 calc R . .
C7I C 0.1385(2) 0.61652(17) 0.4085(4) 0.0528(8) Uani 1 1 d . . .
H7I H 0.1088 0.6506 0.3275 0.063 Uiso 1 1 calc R . .
C20J C 0.5668(2) 0.33046(18) 0.7658(4) 0.0552(8) Uani 1 1 d . . .
H20J H 0.6289 0.3009 0.7695 0.066 Uiso 1 1 calc R . .
C19K C 0.5335(2) 0.37285(18) 0.6279(4) 0.0518(8) Uani 1 1 d . . .
H19K H 0.5730 0.3709 0.5392 0.062 Uiso 1 1 calc R . .
C8L C 0.1966(2) 0.65130(18) 0.5319(4) 0.0594(8) Uani 1 1 d . . .
H8L H 0.2063 0.7089 0.5351 0.071 Uiso 1 1 calc R . .
C14M C 0.2885(3) 0.3040(2) 1.0550(4) 0.0633(9) Uani 1 1 d . . .
H14A H 0.2610 0.2785 0.9572 0.095 Uiso 1 1 calc R . .
H14B H 0.2334 0.3132 1.1243 0.095 Uiso 1 1 calc R . .
H14C H 0.3397 0.2680 1.1074 0.095 Uiso 1 1 calc R . .
C15N C 0.3869(3) 0.4294(2) 1.1709(4) 0.0678(9) Uani 1 1 d . . .
H15A H 0.4358 0.3917 1.2241 0.102 Uiso 1 1 calc R . .
H15B H 0.3332 0.4422 1.2407 0.102 Uiso 1 1 calc R . .
H15C H 0.4217 0.4799 1.1441 0.102 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
Br01 C1D 1.908(3) . ?
O1 C9G 1.373(3) . ?
O1 H1 0.8200 . ?
C17 C18 1.381(3) . ?
C17 C16 1.402(3) . ?
C17 C11 1.475(3) . ?
C16 C21H 1.383(4) . ?
C16 C13A 1.512(4) . ?
C11 C12B 1.341(3) . ?
C11 C10 1.490(3) . ?
C10 C9G 1.374(4) . ?
C10 C4 1.428(4) . ?
C4 C3C 1.416(4) . ?
C4 C5 1.426(3) . ?
C5 C6E 1.415(4) . ?
C5 C7I 1.416(4) . ?
C18 C19K 1.385(4) . ?
C18 H18 0.9300 . ?
C13A C12B 1.513(4) . ?
C13A C15N 1.537(4) . ?
C13A C14M 1.541(4) . ?
C12B H12B 0.9300 . ?
C3C C2F 1.361(4) . ?
C3C H3C 0.9300 . ?
C1D C6E 1.355(4) . ?
C1D C2F 1.401(4) . ?
C6E H6E 0.9300 . ?
C2F H2F 0.9300 . ?
C9G C8L 1.411(4) . ?
C21H C20J 1.387(4) . ?
C21H H21H 0.9300 . ?
C7I C8L 1.352(4) . ?
C7I H7I 0.9300 . ?
C20J C19K 1.379(4) . ?
C20J H20J 0.9300 . ?
C19K H19K 0.9300 . ?
C8L H8L 0.9300 . ?
C14M H14A 0.9600 . ?
C14M H14B 0.9600 . ?
C14M H14C 0.9600 . ?
C15N H15A 0.9600 . ?
C15N H15B 0.9600 . ?
C15N H15C 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
C9G O1 H1 109.5 . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 C11 130.5(2) . . ?
C16 C17 C11 108.4(2) . . ?
C21H C16 C17 119.6(2) . . ?
C21H C16 C13A 130.9(2) . . ?
C17 C16 C13A 109.5(2) . . ?
C12B C11 C17 108.3(2) . . ?
C12B C11 C10 129.1(2) . . ?
C17 C11 C10 122.6(2) . . ?
C9G C10 C4 118.9(2) . . ?
C9G C10 C11 120.6(2) . . ?
C4 C10 C11 120.4(2) . . ?
C3C C4 C5 118.2(2) . . ?
C3C C4 C10 122.0(2) . . ?
C5 C4 C10 119.8(2) . . ?
C6E C5 C7I 122.6(2) . . ?
C6E C5 C4 118.9(2) . . ?
C7I C5 C4 118.5(3) . . ?
C17 C18 C19K 118.6(2) . . ?
C17 C18 H18 120.7 . . ?
C19K C18 H18 120.7 . . ?
C16 C13A C12B 101.4(2) . . ?
C16 C13A C15N 112.2(2) . . ?
C12B C13A C15N 111.3(2) . . ?
C16 C13A C14M 110.2(2) . . ?
C12B C13A C14M 110.9(2) . . ?
C15N C13A C14M 110.6(2) . . ?
C11 C12B C13A 112.3(2) . . ?
C11 C12B H12B 123.8 . . ?
C13A C12B H12B 123.8 . . ?
C2F C3C C4 121.5(2) . . ?
C2F C3C H3C 119.3 . . ?
C4 C3C H3C 119.3 . . ?
C6E C1D C2F 121.5(3) . . ?
C6E C1D Br01 120.3(2) . . ?
C2F C1D Br01 118.2(2) . . ?
C1D C6E C5 120.4(3) . . ?
C1D C6E H6E 119.8 . . ?
C5 C6E H6E 119.8 . . ?
C3C C2F C1D 119.6(3) . . ?
C3C C2F H2F 120.2 . . ?
C1D C2F H2F 120.2 . . ?
O1 C9G C10 122.2(3) . . ?
O1 C9G C8L 116.5(2) . . ?
C10 C9G C8L 121.2(3) . . ?
C16 C21H C20J 119.2(3) . . ?
C16 C21H H21H 120.4 . . ?
C20J C21H H21H 120.4 . . ?
C8L C7I C5 121.1(3) . . ?
C8L C7I H7I 119.5 . . ?
C5 C7I H7I 119.5 . . ?
C19K C20J C21H 120.7(3) . . ?
C19K C20J H20J 119.6 . . ?
C21H C20J H20J 119.6 . . ?
C20J C19K C18 120.8(3) . . ?
C20J C19K H19K 119.6 . . ?
C18 C19K H19K 119.6 . . ?
C7I C8L C9G 120.5(3) . . ?
C7I C8L H8L 119.7 . . ?
C9G C8L H8L 119.7 . . ?
C13A C14M H14A 109.5 . . ?
C13A C14M H14B 109.5 . . ?
H14A C14M H14B 109.5 . . ?
C13A C14M H14C 109.5 . . ?
H14A C14M H14C 109.5 . . ?
H14B C14M H14C 109.5 . . ?
C13A C15N H15A 109.5 . . ?
C13A C15N H15B 109.5 . . ?
H15A C15N H15B 109.5 . . ?
C13A C15N H15C 109.5 . . ?
H15A C15N H15C 109.5 . . ?
H15B C15N H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.83
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.052
