# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mx4171
_database_code_depnum_ccdc_archive 'CCDC 1438278'
_audit_update_record             
;
2015-11-22 deposited with the CCDC.
2017-02-22 downloaded from the CCDC.
;
_audit_creation_date             2015-10-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 Br O2'
_chemical_formula_sum            'C15 H15 Br O2'
_chemical_formula_weight         307.18
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.813(4)
_cell_length_b                   5.321(3)
_cell_length_c                   15.394(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.594(8)
_cell_angle_gamma                90
_cell_volume                     639.7(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2339
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4607
_cell_measurement_theta_min      1.3234
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.204
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4523
_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    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7124
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.608
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.0571
	          2theta: -20.0297
scan:
	Number of images: 330
	           Slice: -110.0000 - 55.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.0571
	          2theta: -20.0297
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 7.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.0571
	          2theta: -20.0297
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             1605
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0135
_diffrn_orient_matrix_UB_12      0.0828
_diffrn_orient_matrix_UB_13      -0.0967
_diffrn_orient_matrix_UB_21      0.0388
_diffrn_orient_matrix_UB_22      0.1370
_diffrn_orient_matrix_UB_23      0.1227
_diffrn_orient_matrix_UB_31      0.0634
_diffrn_orient_matrix_UB_32      -0.0134
_diffrn_orient_matrix_UB_33      -0.0050
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2833
_reflns_number_total             2875
_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, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         2.433
_refine_diff_density_min         -0.770
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2875
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0575
_refine_ls_restrained_S_all      1.071
_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)+(0.0725P)²+1.8060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1501
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.96(3) 0.04(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 -0.61917(8) -0.3721(3) -0.38733(4) 0.0495(3) Uani 1 1 d . . . . .
O1 O -0.2498(8) -0.0965(9) -0.3913(4) 0.0354(12) Uani 1 1 d . . . . .
O2 O -0.0484(8) -0.4808(11) -0.4744(3) 0.0371(12) Uani 1 1 d . . . . .
H2 H -0.0215 -0.3401 -0.4910 0.056 Uiso 1 1 calc GR . . . .
C1 C -0.2494(7) -0.3496(15) -0.3624(4) 0.0245(11) Uani 1 1 d . . . . .
C2 C -0.3906(9) -0.5009(15) -0.4085(5) 0.0310(14) Uani 1 1 d . . . . .
H2A H -0.3838 -0.6741 -0.3890 0.037 Uiso 1 1 calc R . . . .
H2B H -0.3718 -0.4990 -0.4705 0.037 Uiso 1 1 calc R . . . .
C3 C -0.0770(9) -0.4747(14) -0.3831(4) 0.0294(14) Uani 1 1 d . . . . .
H3A H 0.0153 -0.3827 -0.3541 0.035 Uiso 1 1 calc R . . . .
H3B H -0.0758 -0.6451 -0.3606 0.035 Uiso 1 1 calc R . . . .
C4 C -0.2598(7) -0.3473(13) -0.2637(3) 0.0199(10) Uani 1 1 d . . . . .
C5 C -0.3377(9) -0.5391(13) -0.2177(4) 0.0274(13) Uani 1 1 d . . . . .
H5 H -0.3926 -0.6691 -0.2477 0.033 Uiso 1 1 calc R . . . .
C6 C -0.3344(9) -0.5386(13) -0.1272(4) 0.0280(13) Uani 1 1 d . . . . .
H6 H -0.3874 -0.6688 -0.0979 0.034 Uiso 1 1 calc R . . . .
C7 C -0.2541(6) -0.3489(13) -0.0796(3) 0.0186(10) Uani 1 1 d . . . . .
C8 C -0.1742(10) -0.1607(12) -0.1258(5) 0.0291(14) Uani 1 1 d . . . . .
H8 H -0.1169 -0.0330 -0.0957 0.035 Uiso 1 1 calc R . . . .
C9 C -0.1778(10) -0.1586(13) -0.2158(4) 0.0305(15) Uani 1 1 d . . . . .
H9 H -0.1242 -0.0285 -0.2449 0.037 Uiso 1 1 calc R . . . .
C10 C -0.2503(6) -0.3529(15) 0.0178(3) 0.0208(10) Uani 1 1 d . . . . .
C11 C -0.3346(9) -0.5366(13) 0.0639(4) 0.0285(13) Uani 1 1 d . . . . .
H11 H -0.3949 -0.6615 0.0339 0.034 Uiso 1 1 calc R . . . .
C12 C -0.3308(10) -0.5378(14) 0.1546(4) 0.0319(15) Uani 1 1 d . . . . .
H12 H -0.3865 -0.6647 0.1842 0.038 Uiso 1 1 calc R . . . .
C13 C -0.2448(8) -0.3515(16) 0.2006(4) 0.0282(12) Uani 1 1 d . . . . .
H13 H -0.2441 -0.3502 0.2610 0.034 Uiso 1 1 calc R . . . .
C14 C -0.1589(12) -0.1655(16) 0.1552(5) 0.0386(17) Uani 1 1 d . . . . .
H14 H -0.0984 -0.0413 0.1855 0.046 Uiso 1 1 calc R . . . .
C15 C -0.1634(10) -0.1651(13) 0.0655(5) 0.0308(15) Uani 1 1 d . . . . .
H15 H -0.1077 -0.0378 0.0360 0.037 Uiso 1 1 calc R . . . .
H1 H -0.256(10) -0.084(16) -0.437(6) 0.02(2) Uiso 1 1 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 C2 1.949(7) . ?
O1 C1 1.418(9) . ?
O1 H1 0.71(9) . ?
O2 H2 0.8200 . ?
O2 C3 1.430(8) . ?
C1 C2 1.525(9) . ?
C1 C3 1.543(9) . ?
C1 C4 1.524(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.392(9) . ?
C4 C9 1.391(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(9) . ?
C7 C8 1.387(9) . ?
C7 C10 1.499(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(9) . ?
C10 C15 1.404(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(9) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.394(11) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(10) . ?
C15 H15 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
C1 O1 H1 114(7) . . ?
C3 O2 H2 109.5 . . ?
O1 C1 C2 111.1(6) . . ?
O1 C1 C3 109.8(5) . . ?
O1 C1 C4 107.8(6) . . ?
C2 C1 C3 107.5(6) . . ?
C4 C1 C2 114.2(6) . . ?
C4 C1 C3 106.3(5) . . ?
Br1 C2 H2A 109.0 . . ?
Br1 C2 H2B 109.0 . . ?
C1 C2 Br1 113.0(5) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
O2 C3 C1 112.0(6) . . ?
O2 C3 H3A 109.2 . . ?
O2 C3 H3B 109.2 . . ?
C1 C3 H3A 109.2 . . ?
C1 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C1 122.5(6) . . ?
C9 C4 C1 119.8(6) . . ?
C9 C4 C5 117.5(5) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(6) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.7(6) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C8 117.3(5) . . ?
C6 C7 C10 120.9(6) . . ?
C8 C7 C10 121.7(6) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(6) . . ?
C9 C8 H8 119.3 . . ?
C4 C9 H9 119.3 . . ?
C8 C9 C4 121.4(6) . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C7 121.7(6) . . ?
C11 C10 C15 117.7(5) . . ?
C15 C10 C7 120.6(6) . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.2(6) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(6) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.1(6) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(7) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.4(6) . . ?
C14 C15 H15 119.3 . . ?

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
O2 H2 O2 0.82 2.06 2.881(4) 176.9 2_554
O1 H1 Br1 0.71(9) 3.06(9) 3.727(6) 157(8) 2_454

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
O1 C1 C2 Br1 -61.0(6) . . . . ?
O1 C1 C3 O2 -61.6(7) . . . . ?
O1 C1 C4 C5 149.9(6) . . . . ?
O1 C1 C4 C9 -35.4(8) . . . . ?
C1 C4 C5 C6 175.6(6) . . . . ?
C1 C4 C9 C8 -175.3(7) . . . . ?
C2 C1 C3 O2 59.3(8) . . . . ?
C2 C1 C4 C5 25.9(9) . . . . ?
C2 C1 C4 C9 -159.3(6) . . . . ?
C3 C1 C2 Br1 178.8(4) . . . . ?
C3 C1 C4 C5 -92.4(7) . . . . ?
C3 C1 C4 C9 82.3(8) . . . . ?
C4 C1 C2 Br1 61.2(8) . . . . ?
C4 C1 C3 O2 -177.9(6) . . . . ?
C4 C5 C6 C7 0.0(11) . . . . ?
C5 C4 C9 C8 -0.3(11) . . . . ?
C5 C6 C7 C8 -1.1(10) . . . . ?
C5 C6 C7 C10 -179.4(6) . . . . ?
C6 C7 C8 C9 1.5(11) . . . . ?
C6 C7 C10 C11 -3.8(9) . . . . ?
C6 C7 C10 C15 177.7(7) . . . . ?
C7 C8 C9 C4 -0.9(12) . . . . ?
C7 C10 C11 C12 -179.7(6) . . . . ?
C7 C10 C15 C14 179.8(7) . . . . ?
C8 C7 C10 C11 178.0(7) . . . . ?
C8 C7 C10 C15 -0.6(9) . . . . ?
C9 C4 C5 C6 0.7(10) . . . . ?
C10 C7 C8 C9 179.8(6) . . . . ?
C10 C11 C12 C13 1.2(11) . . . . ?
C11 C10 C15 C14 1.3(11) . . . . ?
C11 C12 C13 C14 -1.3(12) . . . . ?
C12 C13 C14 C15 1.4(12) . . . . ?
C13 C14 C15 C10 -1.4(13) . . . . ?
C15 C10 C11 C12 -1.2(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.96(3)
2 0.04(3)

####################################################################### 
# 
# 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_mx4298
_database_code_depnum_ccdc_archive 'CCDC 1439501'
_audit_update_record             
;
2015-11-28 deposited with the CCDC.
2017-02-22 downloaded from the CCDC.
;
_audit_creation_date             2015-11-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H14 Br F O2'
_chemical_formula_sum            'C11 H14 Br F O2'
_chemical_formula_weight         277.13
_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'
F F 0.0171 0.0103 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.651(2)
_cell_length_b                   16.364(7)
_cell_length_c                   38.4918(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3559(2)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    8474
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      28.3284
_cell_measurement_theta_min      1.3522
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.456
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5903
_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    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            34787
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.400
_diffrn_reflns_theta_min         1.352
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 55.2601
	          2theta: -20.0349
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 55.2601
	          2theta: -20.0349
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 55.2601
	          2theta: -20.0349
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             4653
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0088
_diffrn_orient_matrix_UB_12      0.0422
_diffrn_orient_matrix_UB_13      0.1716
_diffrn_orient_matrix_UB_21      -0.0528
_diffrn_orient_matrix_UB_22      0.0291
_diffrn_orient_matrix_UB_23      -0.0099
_diffrn_orient_matrix_UB_31      -0.0130
_diffrn_orient_matrix_UB_32      -0.0220
_diffrn_orient_matrix_UB_33      0.0047
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                6977
_reflns_number_total             7939
_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, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.602
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 
;
 Flack x determined using 2004 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         7939
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0694
_refine_ls_restrained_S_all      1.159
_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)+(0.0055P)²+10.0141P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1135
_refine_special_details          ?
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C2B(H2BB,H2BC), C3B(H3BA,H3BB), C2A(H2AB,H2AC),
 C3A(H3AA,H3AB)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C5B(H5B), C9B(H9B), C5A(H5A), C9A(H9A)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C10B(H10D,H10E,H10F), C11B(H11D,
 H11E,H11F), C10A(H10G,H10H,H10I), C11A(H11G,H11H,H11I)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O1B(H1B), O2B(H2BA), O1A(H1A), O2A(H2AA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.87275(17) 0.77379(6) 0.43743(2) 0.0414(2) Uani 1 1 d . . . . .
F1 F 0.8201(11) 0.9018(3) 0.28377(14) 0.0541(16) Uani 1 1 d . . . . .
O1 O 1.0369(10) 0.6131(3) 0.39013(15) 0.0267(13) Uani 1 1 d . . . . .
H1 H 0.8996 0.6229 0.3956 0.040 Uiso 1 1 calc GR . . . .
O2 O 1.5303(10) 0.6108(3) 0.40187(15) 0.0301(14) Uani 1 1 d . . . . .
H2 H 1.4613 0.5667 0.4027 0.045 Uiso 1 1 calc GR . . . .
C1 C 1.1660(14) 0.6879(4) 0.38763(19) 0.0215(16) Uani 1 1 d . . . . .
C2 C 1.1777(14) 0.7290(5) 0.42310(19) 0.0260(17) Uani 1 1 d . . . . .
H2A H 1.2935 0.7727 0.4223 0.031 Uiso 1 1 calc R . . . .
H2B H 1.2300 0.6894 0.4402 0.031 Uiso 1 1 calc R . . . .
C3 C 1.4174(15) 0.6623(5) 0.3771(2) 0.0266(18) Uani 1 1 d . . . . .
H3A H 1.4102 0.6339 0.3550 0.032 Uiso 1 1 calc R . . . .
H3B H 1.5127 0.7110 0.3739 0.032 Uiso 1 1 calc R . . . .
C4 C 1.0727(15) 0.7442(5) 0.35938(18) 0.0241(17) Uani 1 1 d . . . . .
C5 C 0.9044(14) 0.7187(5) 0.33519(19) 0.0272(17) Uani 1 1 d . . . . .
H5 H 0.8499 0.6652 0.3362 0.033 Uiso 1 1 calc R . . . .
C6 C 0.8137(15) 0.7711(6) 0.3094(2) 0.034(2) Uani 1 1 d . . . . .
C7 C 0.9049(18) 0.8487(5) 0.3089(2) 0.037(2) Uani 1 1 d . . . . .
C8 C 1.0755(18) 0.8786(5) 0.3313(2) 0.037(2) Uani 1 1 d . . . . .
C9 C 1.1566(16) 0.8250(5) 0.3567(2) 0.0282(18) Uani 1 1 d . . . . .
H9 H 1.2700 0.8431 0.3724 0.034 Uiso 1 1 calc R . . . .
C10 C 0.6150(16) 0.7450(6) 0.2855(2) 0.045(3) Uani 1 1 d . . . . .
H10A H 0.6078 0.6864 0.2846 0.067 Uiso 1 1 calc GR . . . .
H10B H 0.6435 0.7659 0.2625 0.067 Uiso 1 1 calc GR . . . .
H10C H 0.4676 0.7660 0.2940 0.067 Uiso 1 1 calc GR . . . .
C11 C 1.171(2) 0.9641(5) 0.3287(2) 0.051(3) Uani 1 1 d . . . . .
H11A H 1.0444 1.0025 0.3315 0.076 Uiso 1 1 calc GR . . . .
H11B H 1.2429 0.9717 0.3063 0.076 Uiso 1 1 calc GR . . . .
H11C H 1.2875 0.9726 0.3465 0.076 Uiso 1 1 calc GR . . . .
Br1B Br 0.56368(17) 0.48144(7) 0.26780(2) 0.0443(3) Uani 1 1 d . . . . .
F1B F 0.5611(12) 0.0957(3) 0.31300(15) 0.0556(17) Uani 1 1 d . . . . .
O1B O 0.7254(10) 0.4708(3) 0.34941(13) 0.0245(12) Uani 1 1 d . . . . .
H1B H 0.5876 0.4745 0.3430 0.037 Uiso 1 1 calc GR . . . .
O2B O 1.2206(10) 0.4968(3) 0.34377(14) 0.0278(13) Uani 1 1 d . . . . .
H2BA H 1.1349 0.5264 0.3555 0.042 Uiso 1 1 calc GR . . . .
C1B C 0.8581(13) 0.4244(5) 0.32441(19) 0.0221(16) Uani 1 1 d . . . . .
C2B C 0.8695(14) 0.4720(5) 0.28996(19) 0.0252(17) Uani 1 1 d . . . . .
H2BB H 0.9778 0.4445 0.2743 0.030 Uiso 1 1 calc R . . . .
H2BC H 0.9315 0.5263 0.2944 0.030 Uiso 1 1 calc R . . . .
C3B C 1.1093(15) 0.4191(5) 0.3392(2) 0.0264(18) Uani 1 1 d . . . . .
H3BA H 1.1033 0.3913 0.3614 0.032 Uiso 1 1 calc R . . . .
H3BB H 1.2054 0.3862 0.3237 0.032 Uiso 1 1 calc R . . . .
C4B C 0.7685(15) 0.3371(5) 0.3203(2) 0.0250(18) Uani 1 1 d . . . . .
C5B C 0.6068(16) 0.3043(5) 0.3437(2) 0.031(2) Uani 1 1 d . . . . .
H5B H 0.5483 0.3370 0.3615 0.037 Uiso 1 1 calc R . . . .
C6B C 0.5303(15) 0.2233(6) 0.3412(2) 0.0319(19) Uani 1 1 d . . . . .
C7B C 0.6302(19) 0.1753(5) 0.3152(2) 0.038(2) Uani 1 1 d . . . . .
C8B C 0.7950(16) 0.2043(5) 0.2915(2) 0.032(2) Uani 1 1 d . . . . .
C9B C 0.8628(16) 0.2853(5) 0.2947(2) 0.0318(19) Uani 1 1 d . . . . .
H9B H 0.9748 0.3062 0.2794 0.038 Uiso 1 1 calc R . . . .
C10B C 0.341(2) 0.1882(6) 0.3652(3) 0.053(3) Uani 1 1 d . . . . .
H10D H 0.3109 0.2261 0.3838 0.079 Uiso 1 1 calc GR . . . .
H10E H 0.3958 0.1374 0.3748 0.079 Uiso 1 1 calc GR . . . .
H10F H 0.1984 0.1791 0.3523 0.079 Uiso 1 1 calc GR . . . .
C11B C 0.9003(18) 0.1478(5) 0.2646(2) 0.047(3) Uani 1 1 d . . . . .
H11D H 0.9298 0.1779 0.2436 0.070 Uiso 1 1 calc GR . . . .
H11E H 0.7916 0.1041 0.2598 0.070 Uiso 1 1 calc GR . . . .
H11F H 1.0464 0.1257 0.2731 0.070 Uiso 1 1 calc GR . . . .
Br1A Br 0.17865(17) 0.28098(6) 0.45967(3) 0.0398(2) Uani 1 1 d . . . . .
F1A F 0.0520(11) 0.5506(4) 0.57434(13) 0.0547(16) Uani 1 1 d . . . . .
O1A O 0.3518(10) 0.4510(3) 0.42152(13) 0.0246(12) Uani 1 1 d . . . . .
H1A H 0.2091 0.4441 0.4241 0.037 Uiso 1 1 calc GR . . . .
O2A O 0.8492(11) 0.4290(4) 0.41851(14) 0.0320(14) Uani 1 1 d . . . . .
H2AA H 0.7988 0.4518 0.4011 0.048 Uiso 1 1 calc GR . . . .
C1A C 0.4743(14) 0.4252(5) 0.45237(19) 0.0244(18) Uani 1 1 d . . . . .
C2A C 0.4896(14) 0.3308(5) 0.4531(2) 0.0290(19) Uani 1 1 d . . . . .
H2AB H 0.5937 0.3139 0.4718 0.035 Uiso 1 1 calc R . . . .
H2AC H 0.5571 0.3116 0.4314 0.035 Uiso 1 1 calc R . . . .
C3A C 0.7265(14) 0.4587(5) 0.44830(19) 0.0273(19) Uani 1 1 d . . . . .
H3AA H 0.7188 0.5178 0.4470 0.033 Uiso 1 1 calc R . . . .
H3AB H 0.8168 0.4447 0.4689 0.033 Uiso 1 1 calc R . . . .
C4A C 0.3680(14) 0.4618(5) 0.4854(2) 0.0249(17) Uani 1 1 d . . . . .
C5A C 0.1996(15) 0.5242(5) 0.4836(2) 0.0278(18) Uani 1 1 d . . . . .
H5A H 0.1587 0.5457 0.4621 0.033 Uiso 1 1 calc R . . . .
C6A C 0.0917(16) 0.5547(5) 0.5134(2) 0.033(2) Uani 1 1 d . . . . .
C7A C 0.1659(16) 0.5226(6) 0.5448(2) 0.034(2) Uani 1 1 d . . . . .
C8A C 0.3351(19) 0.4639(6) 0.5483(2) 0.041(2) Uani 1 1 d . . . . .
C9A C 0.4361(17) 0.4336(5) 0.5180(2) 0.033(2) Uani 1 1 d . . . . .
H9A H 0.5520 0.3934 0.5196 0.040 Uiso 1 1 calc R . . . .
C10A C -0.1016(18) 0.6192(6) 0.5118(3) 0.050(3) Uani 1 1 d . . . . .
H10G H -0.2433 0.5981 0.5223 0.074 Uiso 1 1 calc GR . . . .
H10H H -0.1324 0.6330 0.4880 0.074 Uiso 1 1 calc GR . . . .
H10I H -0.0512 0.6671 0.5242 0.074 Uiso 1 1 calc GR . . . .
C11A C 0.412(3) 0.4349(8) 0.5841(2) 0.079(4) Uani 1 1 d . . . . .
H11G H 0.4654 0.4808 0.5976 0.118 Uiso 1 1 calc GR . . . .
H11H H 0.5389 0.3962 0.5818 0.118 Uiso 1 1 calc GR . . . .
H11I H 0.2809 0.4094 0.5957 0.118 Uiso 1 1 calc GR . . . .


_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 1.952(8) . ?
F1 C7 1.386(9) . ?
O1 H1 0.8200 . ?
O1 C1 1.428(9) . ?
O2 H2 0.8200 . ?
O2 C3 1.424(9) . ?
C1 C2 1.524(10) . ?
C1 C3 1.536(11) . ?
C1 C4 1.520(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.395(11) . ?
C4 C9 1.408(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.409(11) . ?
C6 C7 1.371(12) . ?
C6 C10 1.513(12) . ?
C7 C8 1.383(13) . ?
C8 C9 1.391(11) . ?
C8 C11 1.503(12) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
Br1B C2B 1.933(8) . ?
F1B C7B 1.362(10) . ?
O1B H1B 0.8200 . ?
O1B C1B 1.436(9) . ?
O2B H2BA 0.8200 . ?
O2B C3B 1.430(9) . ?
C1B C2B 1.539(10) . ?
C1B C3B 1.531(11) . ?
C1B C4B 1.524(10) . ?
C2B H2BB 0.9700 . ?
C2B H2BC 0.9700 . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C4B C5B 1.392(11) . ?
C4B C9B 1.402(10) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.397(12) . ?
C6B C7B 1.393(12) . ?
C6B C10B 1.525(12) . ?
C7B C8B 1.385(12) . ?
C8B C9B 1.386(11) . ?
C8B C11B 1.512(11) . ?
C9B H9B 0.9300 . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 0.9600 . ?
Br1A C2A 1.954(8) . ?
F1A C7A 1.386(9) . ?
O1A H1A 0.8200 . ?
O1A C1A 1.438(8) . ?
O2A H2AA 0.8200 . ?
O2A C3A 1.426(9) . ?
C1A C2A 1.547(11) . ?
C1A C3A 1.536(11) . ?
C1A C4A 1.529(10) . ?
C2A H2AB 0.9700 . ?
C2A H2AC 0.9700 . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C4A C5A 1.396(11) . ?
C4A C9A 1.393(11) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.392(11) . ?
C6A C7A 1.380(12) . ?
C6A C10A 1.520(13) . ?
C7A C8A 1.363(13) . ?
C8A C9A 1.389(11) . ?
C8A C11A 1.522(12) . ?
C9A H9A 0.9300 . ?
C10A H10G 0.9600 . ?
C10A H10H 0.9600 . ?
C10A H10I 0.9600 . ?
C11A H11G 0.9600 . ?
C11A H11H 0.9600 . ?
C11A H11I 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
C1 O1 H1 109.5 . . ?
C3 O2 H2 109.5 . . ?
O1 C1 C2 109.9(6) . . ?
O1 C1 C3 104.9(6) . . ?
O1 C1 C4 113.0(6) . . ?
C2 C1 C3 108.5(6) . . ?
C4 C1 C2 112.8(6) . . ?
C4 C1 C3 107.3(6) . . ?
Br1 C2 H2A 109.1 . . ?
Br1 C2 H2B 109.1 . . ?
C1 C2 Br1 112.4(5) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
O2 C3 C1 113.5(6) . . ?
O2 C3 H3A 108.9 . . ?
O2 C3 H3B 108.9 . . ?
C1 C3 H3A 108.9 . . ?
C1 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C1 122.2(7) . . ?
C5 C4 C9 117.4(7) . . ?
C9 C4 C1 120.4(7) . . ?
C4 C5 H5 118.7 . . ?
C4 C5 C6 122.5(8) . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C10 121.8(8) . . ?
C7 C6 C5 115.8(8) . . ?
C7 C6 C10 122.2(8) . . ?
C6 C7 F1 117.4(8) . . ?
C6 C7 C8 125.6(8) . . ?
C8 C7 F1 117.0(8) . . ?
C7 C8 C9 116.4(8) . . ?
C7 C8 C11 122.6(8) . . ?
C9 C8 C11 121.1(9) . . ?
C4 C9 H9 118.9 . . ?
C8 C9 C4 122.2(8) . . ?
C8 C9 H9 118.9 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1B O1B H1B 109.5 . . ?
C3B O2B H2BA 109.5 . . ?
O1B C1B C2B 109.4(6) . . ?
O1B C1B C3B 105.4(6) . . ?
O1B C1B C4B 113.0(6) . . ?
C3B C1B C2B 108.1(6) . . ?
C4B C1B C2B 113.4(6) . . ?
C4B C1B C3B 107.0(6) . . ?
Br1B C2B H2BB 109.1 . . ?
Br1B C2B H2BC 109.1 . . ?
C1B C2B Br1B 112.5(5) . . ?
C1B C2B H2BB 109.1 . . ?
C1B C2B H2BC 109.1 . . ?
H2BB C2B H2BC 107.8 . . ?
O2B C3B C1B 113.7(6) . . ?
O2B C3B H3BA 108.8 . . ?
O2B C3B H3BB 108.8 . . ?
C1B C3B H3BA 108.8 . . ?
C1B C3B H3BB 108.8 . . ?
H3BA C3B H3BB 107.7 . . ?
C5B C4B C1B 120.8(7) . . ?
C5B C4B C9B 118.1(7) . . ?
C9B C4B C1B 120.9(7) . . ?
C4B C5B H5B 119.2 . . ?
C4B C5B C6B 121.6(8) . . ?
C6B C5B H5B 119.2 . . ?
C5B C6B C10B 122.1(8) . . ?
C7B C6B C5B 117.3(8) . . ?
C7B C6B C10B 120.6(8) . . ?
F1B C7B C6B 117.8(8) . . ?
F1B C7B C8B 118.7(8) . . ?
C8B C7B C6B 123.5(8) . . ?
C7B C8B C9B 117.0(8) . . ?
C7B C8B C11B 120.4(8) . . ?
C9B C8B C11B 122.5(8) . . ?
C4B C9B H9B 118.8 . . ?
C8B C9B C4B 122.4(8) . . ?
C8B C9B H9B 118.8 . . ?
C6B C10B H10D 109.5 . . ?
C6B C10B H10E 109.5 . . ?
C6B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C8B C11B H11D 109.5 . . ?
C8B C11B H11E 109.5 . . ?
C8B C11B H11F 109.5 . . ?
H11D C11B H11E 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C1A O1A H1A 109.5 . . ?
C3A O2A H2AA 109.5 . . ?
O1A C1A C2A 109.6(6) . . ?
O1A C1A C3A 104.9(6) . . ?
O1A C1A C4A 112.5(6) . . ?
C3A C1A C2A 107.9(7) . . ?
C4A C1A C2A 113.5(6) . . ?
C4A C1A C3A 108.0(6) . . ?
Br1A C2A H2AB 109.3 . . ?
Br1A C2A H2AC 109.3 . . ?
C1A C2A Br1A 111.6(6) . . ?
C1A C2A H2AB 109.3 . . ?
C1A C2A H2AC 109.3 . . ?
H2AB C2A H2AC 108.0 . . ?
O2A C3A C1A 114.3(7) . . ?
O2A C3A H3AA 108.7 . . ?
O2A C3A H3AB 108.7 . . ?
C1A C3A H3AA 108.7 . . ?
C1A C3A H3AB 108.7 . . ?
H3AA C3A H3AB 107.6 . . ?
C5A C4A C1A 120.9(7) . . ?
C9A C4A C1A 120.7(7) . . ?
C9A C4A C5A 118.3(7) . . ?
C4A C5A H5A 119.3 . . ?
C6A C5A C4A 121.4(7) . . ?
C6A C5A H5A 119.3 . . ?
C5A C6A C10A 122.1(8) . . ?
C7A C6A C5A 116.7(8) . . ?
C7A C6A C10A 121.2(8) . . ?
C6A C7A F1A 116.8(8) . . ?
C8A C7A F1A 118.4(7) . . ?
C8A C7A C6A 124.7(8) . . ?
C7A C8A C9A 117.1(8) . . ?
C7A C8A C11A 120.8(8) . . ?
C9A C8A C11A 122.1(9) . . ?
C4A C9A H9A 119.2 . . ?
C8A C9A C4A 121.6(8) . . ?
C8A C9A H9A 119.2 . . ?
C6A C10A H10G 109.5 . . ?
C6A C10A H10H 109.5 . . ?
C6A C10A H10I 109.5 . . ?
H10G C10A H10H 109.5 . . ?
H10G C10A H10I 109.5 . . ?
H10H C10A H10I 109.5 . . ?
C8A C11A H11G 109.5 . . ?
C8A C11A H11H 109.5 . . ?
C8A C11A H11I 109.5 . . ?
H11G C11A H11H 109.5 . . ?
H11G C11A H11I 109.5 . . ?
H11H C11A H11I 109.5 . . ?

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 O2 0.82 2.11 2.898(8) 161.2 1_455
O2 H2 O1A 0.82 2.12 2.903(8) 159.6 1_655
O1B H1B Br1B 0.82 2.90 3.276(5) 110.4 .
O1B H1B O2B 0.82 2.11 2.893(8) 160.8 1_455
O2B H2BA O1 0.82 2.02 2.808(8) 159.7 .
O2B H2BA O1B 0.82 2.50 2.839(8) 106.3 .
O1A H1A O2A 0.82 2.06 2.865(8) 167.0 1_455
O2A H2AA O1B 0.82 2.05 2.834(8) 158.6 .

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
F1 C7 C8 C9 179.1(8) . . . . ?
F1 C7 C8 C11 -1.2(14) . . . . ?
O1 C1 C2 Br1 -71.4(7) . . . . ?
O1 C1 C3 O2 -61.3(8) . . . . ?
O1 C1 C4 C5 -9.7(10) . . . . ?
O1 C1 C4 C9 170.7(7) . . . . ?
C1 C4 C5 C6 178.8(7) . . . . ?
C1 C4 C9 C8 -179.8(8) . . . . ?
C2 C1 C3 O2 56.1(8) . . . . ?
C2 C1 C4 C5 -135.1(8) . . . . ?
C2 C1 C4 C9 45.3(10) . . . . ?
C3 C1 C2 Br1 174.5(5) . . . . ?
C3 C1 C4 C5 105.4(8) . . . . ?
C3 C1 C4 C9 -74.1(9) . . . . ?
C4 C1 C2 Br1 55.7(8) . . . . ?
C4 C1 C3 O2 178.3(6) . . . . ?
C4 C5 C6 C7 1.3(12) . . . . ?
C4 C5 C6 C10 -174.2(8) . . . . ?
C5 C4 C9 C8 0.6(12) . . . . ?
C5 C6 C7 F1 179.9(7) . . . . ?
C5 C6 C7 C8 0.2(14) . . . . ?
C6 C7 C8 C9 -1.2(15) . . . . ?
C6 C7 C8 C11 178.5(10) . . . . ?
C7 C8 C9 C4 0.7(13) . . . . ?
C9 C4 C5 C6 -1.7(12) . . . . ?
C10 C6 C7 F1 -4.6(13) . . . . ?
C10 C6 C7 C8 175.7(9) . . . . ?
C11 C8 C9 C4 -178.9(9) . . . . ?
F1B C7B C8B C9B -179.4(8) . . . . ?
F1B C7B C8B C11B -1.6(14) . . . . ?
O1B C1B C2B Br1B -67.0(7) . . . . ?
O1B C1B C3B O2B -60.9(8) . . . . ?
O1B C1B C4B C5B -11.8(11) . . . . ?
O1B C1B C4B C9B 174.1(7) . . . . ?
C1B C4B C5B C6B -177.2(8) . . . . ?
C1B C4B C9B C8B 176.3(8) . . . . ?
C2B C1B C3B O2B 56.0(8) . . . . ?
C2B C1B C4B C5B -137.1(8) . . . . ?
C2B C1B C4B C9B 48.8(10) . . . . ?
C3B C1B C2B Br1B 178.7(5) . . . . ?
C3B C1B C4B C5B 103.8(9) . . . . ?
C3B C1B C4B C9B -70.3(9) . . . . ?
C4B C1B C2B Br1B 60.2(8) . . . . ?
C4B C1B C3B O2B 178.5(6) . . . . ?
C4B C5B C6B C7B 2.8(13) . . . . ?
C4B C5B C6B C10B -175.9(9) . . . . ?
C5B C4B C9B C8B 2.1(13) . . . . ?
C5B C6B C7B F1B 178.5(8) . . . . ?
C5B C6B C7B C8B -1.5(14) . . . . ?
C6B C7B C8B C9B 0.6(14) . . . . ?
C6B C7B C8B C11B 178.4(9) . . . . ?
C7B C8B C9B C4B -0.9(13) . . . . ?
C9B C4B C5B C6B -3.0(13) . . . . ?
C10B C6B C7B F1B -2.8(14) . . . . ?
C10B C6B C7B C8B 177.2(9) . . . . ?
C11B C8B C9B C4B -178.6(9) . . . . ?
F1A C7A C8A C9A 176.2(8) . . . . ?
F1A C7A C8A C11A -5.2(15) . . . . ?
O1A C1A C2A Br1A -68.1(7) . . . . ?
O1A C1A C3A O2A -60.4(8) . . . . ?
O1A C1A C4A C5A -10.6(11) . . . . ?
O1A C1A C4A C9A 169.1(8) . . . . ?
C1A C4A C5A C6A 176.3(8) . . . . ?
C1A C4A C9A C8A -177.5(9) . . . . ?
C2A C1A C3A O2A 56.4(8) . . . . ?
C2A C1A C4A C5A -135.7(8) . . . . ?
C2A C1A C4A C9A 44.0(11) . . . . ?
C3A C1A C2A Br1A 178.2(5) . . . . ?
C3A C1A C4A C5A 104.7(8) . . . . ?
C3A C1A C4A C9A -75.6(10) . . . . ?
C4A C1A C2A Br1A 58.5(8) . . . . ?
C4A C1A C3A O2A 179.5(6) . . . . ?
C4A C5A C6A C7A 2.4(13) . . . . ?
C4A C5A C6A C10A -176.5(8) . . . . ?
C5A C4A C9A C8A 2.2(13) . . . . ?
C5A C6A C7A F1A -177.5(8) . . . . ?
C5A C6A C7A C8A 0.0(14) . . . . ?
C6A C7A C8A C9A -1.2(15) . . . . ?
C6A C7A C8A C11A 177.4(10) . . . . ?
C7A C8A C9A C4A 0.0(14) . . . . ?
C9A C4A C5A C6A -3.5(12) . . . . ?
C10A C6A C7A F1A 1.5(13) . . . . ?
C10A C6A C7A C8A 178.9(9) . . . . ?
C11A C8A C9A C4A -178.5(10) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
