# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1536256'
_audit_update_record             
;
2017-03-06 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;
_audit_creation_date             2017-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 Br F2 O'
_chemical_formula_sum            'C18 H17 Br F2 O'
_chemical_formula_weight         367.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H17 O1 F2 Br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   34.5876(4)
_cell_length_b                   9.19962(10)
_cell_length_c                   4.92247(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1566.29(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12038
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      67.0800
_cell_measurement_theta_min      2.5490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.762
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0074
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            13397
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.215
_diffrn_reflns_theta_max         67.215
_diffrn_reflns_theta_min         2.555
_diffrn_ambient_temperature      123.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -179.00   0.00   1.00   10.00    --  -90.00  60.00-108.00  179
  2  ω   -110.00  69.00   1.00   10.00    --  -21.00  30.00 -36.00  179
  3  ω   -179.00   0.00   1.00   10.00    --  -90.00  60.00-180.00  179
  4  ω   -179.00   0.00   1.00   10.00    --  -90.00  60.00 -36.00  179
  5  ω   -179.00   0.00   1.00   10.00    --  -90.00  60.00 108.00  179
  6  ω   -179.00   0.00   1.00   10.00    --  -90.00  60.00  36.00  179
  7  ω   -179.00   0.00   1.00   10.00    --  -90.00  30.00 108.00  179
  8  ω    -99.00  80.00   1.00   10.00    --  -10.00  30.00 108.00  179
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn944+ (2x2 bin mode)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0160927000
_diffrn_orient_matrix_UB_12      -0.0113232000
_diffrn_orient_matrix_UB_13      0.2910486000
_diffrn_orient_matrix_UB_21      -0.0244783000
_diffrn_orient_matrix_UB_22      0.1323031000
_diffrn_orient_matrix_UB_23      0.0847545000
_diffrn_orient_matrix_UB_31      -0.0335598000
_diffrn_orient_matrix_UB_32      -0.1019964000
_diffrn_orient_matrix_UB_33      0.0777939000
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-003'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1456
_reflns_number_total             1462
_reflns_odcompleteness_completeness 98.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.10
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       
;
Rigaku Collection Strategy
(Daniels, L. M. (2011). Acta Cryst. A67, C143)
;
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    
;
Mercury CSD 3.9 (Macrae, C. F., et al. (2006). J. Appl. Cryst. 39, 453-457)
POV-Ray 3.7 (Persistence of Vision Pty. Ltd. (2004)) 
;
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1462
_refine_ls_number_restraints     118
_refine_ls_R_factor_all          0.0236
_refine_ls_R_factor_gt           0.0235
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+0.9302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0627
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C14-C13 \\sim C14-C15
 with sigma of 0.02
 C16-C15 \\sim C12-C13
 with sigma of 0.02
 C11-C12 \\sim C11-C10 \\sim C11-C16
 with sigma of 0.02
 C16-C13 \\sim C15-C12
 with sigma of 0.02
3. Restrained planarity
 O1, C9, C8, C10
 with sigma of 0.1
 C11, C14, C13, C12, C16, C15
 with sigma of 0.1
4. Rigid body (RIGU) restrains
 C5, C1, C6, C4, C7, C9, C2, C11, C3, C14, C13, C12, C8, C10, C16, C15, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O1(0.5) H5A(0.5) H5B(0.5) H7A(0.5) H7B(0.5) C11(0.5) C14(0.5)
 H14(0.5) C13(0.5) H13(0.5) C12(0.5) H12(0.5) H8A(0.5) H8B(0.5) C10(0.5)
 H10A(0.5) H10B(0.5) C16(0.5) H16(0.5) C15(0.5) H15(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C14(H14), C13(H13), C12(H12), C16(H16), C15(H15)
;
_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 0.32557(2) 0.250000 1.29147(6) 0.03693(13) Uani 1 2 d S T P . .
F1 F 0.50499(3) 0.36850(11) 0.78835(19) 0.0317(2) Uani 1 1 d . . . . .
O1 O 0.60528(5) 0.2693(13) 0.1426(4) 0.0217(18) Uani 0.5 1 d . U . A -1
C5 C 0.46275(6) 0.250000 0.4846(5) 0.0291(5) Uani 1 2 d S TU P . .
H5A H 0.460430 0.336921 0.367143 0.035 Uiso 0.5 1 calc R . . . .
H5B H 0.460430 0.163079 0.367142 0.035 Uiso 0.5 1 calc R . . . .
C1 C 0.36927(6) 0.250000 1.0561(5) 0.0259(5) Uani 1 2 d S TU P . .
C6 C 0.50223(6) 0.250000 0.6169(5) 0.0226(4) Uani 1 2 d S TU P . .
C4 C 0.42996(6) 0.250000 0.6869(5) 0.0252(5) Uani 1 2 d S TU P . .
C7 C 0.53604(6) 0.250000 0.4247(4) 0.0227(4) Uani 1 2 d S TU P . .
H7A H 0.534485 0.336963 0.306693 0.027 Uiso 0.5 1 calc R . . . .
H7B H 0.534485 0.163037 0.306693 0.027 Uiso 0.5 1 calc R . . . .
C9 C 0.60919(6) 0.250000 0.3834(4) 0.0223(4) Uani 1 2 d S TU P . .
C2 C 0.38431(4) 0.38048(18) 0.9681(4) 0.0318(4) Uani 1 1 d . U . . .
H2 H 0.374116 0.469879 1.032846 0.038 Uiso 1 1 calc R . . . .
C11 C 0.68112(9) 0.2324(18) 0.3045(6) 0.023(2) Uani 0.5 1 d D U . A -1
C3 C 0.41455(5) 0.37910(19) 0.7836(4) 0.0315(4) Uani 1 1 d . U . . .
H3 H 0.424978 0.468755 0.721961 0.038 Uiso 1 1 calc R . . . .
C14 C 0.73699(8) 0.262(2) -0.1021(6) 0.0307(17) Uani 0.5 1 d D U . A -1
H14 H 0.755758 0.271918 -0.241810 0.037 Uiso 0.5 1 calc R . . A -1
C13 C 0.7251(5) 0.1257(18) -0.022(4) 0.034(2) Uani 0.5 1 d D U . A -1
H13 H 0.735749 0.041679 -0.105089 0.041 Uiso 0.5 1 calc R . . A -1
C12 C 0.6974(5) 0.1110(17) 0.182(3) 0.031(2) Uani 0.5 1 d D U . A -1
H12 H 0.689477 0.016607 0.237046 0.037 Uiso 0.5 1 calc R . . A -1
C8 C 0.57486(6) 0.250000 0.5721(5) 0.0268(5) Uani 1 2 d S TU P A .
H8A H 0.576275 0.336896 0.690278 0.032 Uiso 0.5 1 calc R . . . .
H8B H 0.576275 0.163104 0.690277 0.032 Uiso 0.5 1 calc R . . . .
C10 C 0.64890(7) 0.2234(7) 0.5101(6) 0.0289(17) Uani 0.5 1 d D U . A -1
H10A H 0.653451 0.296273 0.654576 0.035 Uiso 0.5 1 calc R . . A -1
H10B H 0.649192 0.125962 0.595526 0.035 Uiso 0.5 1 calc R . . A -1
C16 C 0.6939(4) 0.3695(16) 0.223(3) 0.027(2) Uani 0.5 1 d D U . A -1
H16 H 0.683632 0.453910 0.307894 0.032 Uiso 0.5 1 calc R . . A -1
C15 C 0.7217(5) 0.3842(16) 0.020(3) 0.028(2) Uani 0.5 1 d D U . A -1
H15 H 0.730088 0.478150 -0.034427 0.034 Uiso 0.5 1 calc R . . A -1


_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(2) . ?
F1 C6 1.3821(16) . ?
O1 C9 1.206(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.513(3) . ?
C5 C4 1.509(3) . ?
C1 C2 1.378(2) . ?
C1 C2 1.378(2) 7_565 ?
C6 C7 1.504(3) . ?
C4 C3 1.386(2) . ?
C4 C3 1.386(2) 7_565 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.526(3) . ?
C9 C8 1.507(3) . ?
C9 C10 1.528(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(2) . ?
C11 C12 1.389(9) . ?
C11 C10 1.507(4) . ?
C11 C16 1.396(10) . ?
C3 H3 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.379(11) . ?
C14 C15 1.380(10) . ?
C13 H13 0.9500 . ?
C13 C12 1.392(10) . ?
C12 H12 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C16 H16 0.9500 . ?
C16 C15 1.394(9) . ?
C15 H15 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
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C4 C5 C6 113.23(19) . . ?
C2 C1 Br1 119.41(10) 7_565 . ?
C2 C1 Br1 119.40(10) . . ?
C2 C1 C2 121.1(2) . 7_565 ?
F1 C6 F1 104.14(17) . 7_565 ?
F1 C6 C5 108.97(12) 7_565 . ?
F1 C6 C5 108.97(12) . . ?
F1 C6 C7 109.30(11) . . ?
F1 C6 C7 109.30(11) 7_565 . ?
C7 C6 C5 115.54(18) . . ?
C3 C4 C5 121.04(11) 7_565 . ?
C3 C4 C5 121.04(11) . . ?
C3 C4 C3 117.9(2) 7_565 . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C6 C7 C8 112.64(18) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
O1 C9 C8 121.14(19) . . ?
O1 C9 C10 121.7(2) . . ?
C8 C9 C10 117.16(19) . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.90(15) . . ?
C3 C2 H2 120.6 . . ?
C12 C11 C10 123.2(10) . . ?
C12 C11 C16 118.3(3) . . ?
C16 C11 C10 118.5(10) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 C4 121.56(16) . . ?
C2 C3 H3 119.2 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.1(4) . . ?
C15 C14 H14 120.0 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 120.1(7) . . ?
C12 C13 H13 120.0 . . ?
C11 C12 C13 120.9(7) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 C7 113.58(18) . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 C9 112.4(3) . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.8(6) . . ?
C15 C16 H16 119.6 . . ?
C14 C15 C16 119.9(6) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.623
_oxdiff_exptl_absorpt_empirical_full_min 0.511
