# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_fxm-lyb
_database_code_depnum_ccdc_archive 'CCDC 1479692'
_audit_update_record             
;
2016-05-16 deposited with the CCDC.
2016-09-07 downloaded from the CCDC.
;
_audit_creation_date             2015-09-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.21 svn.r3230 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        1,3-diene
_chemical_formula_moiety         'C18 H19 Br O3'
_chemical_formula_sum            'C18 H19 Br O3'
_chemical_formula_weight         363.24
_chemical_absolute_configuration rmad
_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 0.0181 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'
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           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                   8.7409(4)
_cell_length_b                   12.0555(4)
_cell_length_c                   16.4217(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1730.45(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4550
_cell_measurement_temperature    292.56(10)
_cell_measurement_theta_max      72.4250
_cell_measurement_theta_min      4.5510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9066
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         4.550
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.56(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   17.00  105.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega   17.00  105.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  -30.0000 88

#__ type_ start__ end____ width___ exp.time_
  3 omega  -31.00   63.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega   20.00  104.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   75.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   91.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00  135.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   91.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   81.00  176.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   91.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00  135.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
 12 omega   57.00  150.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
 13 omega  -31.00   53.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
 14 omega   17.00  105.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000   30.0000 88

#__ type_ start__ end____ width___ exp.time_
 15 omega   10.00  104.00   1.0000    1.1800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   60.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1623421000
_diffrn_orient_matrix_UB_12      -0.0494349000
_diffrn_orient_matrix_UB_13      0.0001945000
_diffrn_orient_matrix_UB_21      -0.0569040000
_diffrn_orient_matrix_UB_22      -0.0970720000
_diffrn_orient_matrix_UB_23      0.0529670000
_diffrn_orient_matrix_UB_31      -0.0381888000
_diffrn_orient_matrix_UB_32      -0.0665474000
_diffrn_orient_matrix_UB_33      -0.0775799000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2928
_reflns_number_total             3091
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 
;
 Flack x determined using 1173 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.086
_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)+(0.0995P)²+0.2319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1445
_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
2. Restrained distances
 C1-C00K
 1.29 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C00H(H00G,H00H), C00I(H00I,H00J)
3.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00K(H00N)
3.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.d Idealised Me refined as rotating group:
 C00G(H00A,H00E,H00F), C00J(H00K,H00L,H00M), C00L(H00O,H00P,H00Q)
;
_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
Br01 Br 0.15736(11) 0.10178(5) 0.50089(4) 0.1011(4) Uani 1 1 d . . . . .
O002 O 0.5273(4) 0.7015(4) 0.6496(2) 0.0678(9) Uani 1 1 d . . . . .
O003 O 0.5007(5) 0.4952(3) 0.7501(2) 0.0753(11) Uani 1 1 d . . . . .
O004 O 0.4438(5) 0.6217(4) 0.5352(2) 0.0785(11) Uani 1 1 d . . . . .
C005 C 0.3541(4) 0.3851(4) 0.6575(2) 0.0480(8) Uani 1 1 d . . . . .
C006 C 0.4328(5) 0.6392(4) 0.6063(3) 0.0542(10) Uani 1 1 d . . . . .
C007 C 0.4018(5) 0.4873(4) 0.6986(3) 0.0542(10) Uani 1 1 d . . . . .
C008 C 0.2378(6) 0.2198(4) 0.5650(3) 0.0597(10) Uani 1 1 d . . . . .
C009 C 0.2363(5) 0.4083(4) 0.6029(3) 0.0510(9) Uani 1 1 d . . . . .
C00A C 0.2430(5) 0.6624(5) 0.7260(3) 0.0597(11) Uani 1 1 d . . . . .
C00B C 0.3518(6) 0.1947(4) 0.6204(3) 0.0620(11) Uani 1 1 d . . . . .
H00B H 0.3874 0.1224 0.6261 0.074 Uiso 1 1 calc R . . . .
C00C C 0.4115(5) 0.2797(4) 0.6668(3) 0.0572(10) Uani 1 1 d . . . . .
H00C H 0.4895 0.2658 0.7040 0.069 Uiso 1 1 calc R . . . .
C00D C 0.1772(6) 0.3244(4) 0.5548(3) 0.0603(11) Uani 1 1 d . . . . .
H00D H 0.0998 0.3380 0.5172 0.072 Uiso 1 1 calc R . . . .
C00E C 0.3103(4) 0.5859(4) 0.6608(3) 0.0513(9) Uani 1 1 d . . . . .
C00F C 0.2040(5) 0.7682(5) 0.7121(4) 0.0674(13) Uani 1 1 d . . . . .
C00G C 0.2219(8) 0.8260(5) 0.6322(4) 0.0811(16) Uani 1 1 d . . . . .
H00A H 0.3045 0.8783 0.6357 0.122 Uiso 1 1 calc GR . . . .
H00E H 0.1289 0.8644 0.6191 0.122 Uiso 1 1 calc GR . . . .
H00F H 0.2438 0.7725 0.5906 0.122 Uiso 1 1 calc GR . . . .
C00H C 0.1885(5) 0.5274(4) 0.6076(3) 0.0606(11) Uani 1 1 d . . . . .
H00G H 0.0880 0.5339 0.6323 0.073 Uiso 1 1 calc R . . . .
H00H H 0.1851 0.5602 0.5537 0.073 Uiso 1 1 calc R . . . .
C00I C 0.6537(8) 0.7541(7) 0.6080(5) 0.0898(19) Uani 1 1 d . . . . .
H00I H 0.6645 0.8300 0.6266 0.108 Uiso 1 1 calc R . . . .
H00J H 0.6345 0.7552 0.5498 0.108 Uiso 1 1 calc R . . . .
C00J C 0.1365(9) 0.8419(7) 0.7770(5) 0.105(2) Uani 1 1 d . . . . .
H00K H 0.0271 0.8425 0.7720 0.157 Uiso 1 1 calc GR . . . .
H00L H 0.1751 0.9159 0.7707 0.157 Uiso 1 1 calc GR . . . .
H00M H 0.1644 0.8141 0.8298 0.157 Uiso 1 1 calc GR . . . .
C00K C 0.2085(10) 0.6117(8) 0.8050(4) 0.105(2) Uani 1 1 d D . . . .
H00N H 0.2706 0.6421 0.8452 0.126 Uiso 1 1 calc R . . . .
C00L C 0.7949(7) 0.6919(11) 0.6250(7) 0.132(4) Uani 1 1 d . . . . .
H00O H 0.7930 0.6228 0.5960 0.198 Uiso 1 1 calc GR . . . .
H00P H 0.8022 0.6777 0.6824 0.198 Uiso 1 1 calc GR . . . .
H00Q H 0.8817 0.7347 0.6078 0.198 Uiso 1 1 calc GR . . . .
C1 C 0.1275(19) 0.5453(12) 0.8330(8) 0.195(8) Uani 1 1 d D . . . .
H1A H 0.0584 0.5076 0.8000 0.234 Uiso 1 1 calc R . . . .
H1B H 0.1318 0.5299 0.8885 0.234 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 C008 1.905(5) . ?
O002 C006 1.324(6) . ?
O002 C00I 1.445(7) . ?
O003 C007 1.212(6) . ?
O004 C006 1.190(6) . ?
C005 C007 1.465(6) . ?
C005 C009 1.394(5) . ?
C005 C00C 1.376(7) . ?
C006 C00E 1.537(6) . ?
C007 C00E 1.561(6) . ?
C008 C00B 1.383(7) . ?
C008 C00D 1.378(7) . ?
C009 C00D 1.383(6) . ?
C009 C00H 1.497(7) . ?
C00A C00E 1.530(6) . ?
C00A C00F 1.340(8) . ?
C00A C00K 1.465(8) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.380(8) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00E C00H 1.547(6) . ?
C00F C00G 1.494(9) . ?
C00F C00J 1.508(8) . ?
C00G H00A 0.9600 . ?
C00G H00E 0.9600 . ?
C00G H00F 0.9600 . ?
C00H H00G 0.9700 . ?
C00H H00H 0.9700 . ?
C00I H00I 0.9700 . ?
C00I H00J 0.9700 . ?
C00I C00L 1.471(11) . ?
C00J H00K 0.9600 . ?
C00J H00L 0.9600 . ?
C00J H00M 0.9600 . ?
C00K H00N 0.9300 . ?
C00K C1 1.164(12) . ?
C00L H00O 0.9600 . ?
C00L H00P 0.9600 . ?
C00L H00Q 0.9600 . ?
C1 H1A 0.9300 . ?
C1 H1B 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
C006 O002 C00I 118.2(5) . . ?
C009 C005 C007 109.8(4) . . ?
C00C C005 C007 128.5(4) . . ?
C00C C005 C009 121.8(4) . . ?
O002 C006 C00E 111.1(4) . . ?
O004 C006 O002 125.2(5) . . ?
O004 C006 C00E 123.6(5) . . ?
O003 C007 C005 126.1(5) . . ?
O003 C007 C00E 125.6(5) . . ?
C005 C007 C00E 108.1(3) . . ?
C00B C008 Br01 117.7(4) . . ?
C00D C008 Br01 118.3(4) . . ?
C00D C008 C00B 123.9(4) . . ?
C005 C009 C00H 111.4(4) . . ?
C00D C009 C005 119.8(4) . . ?
C00D C009 C00H 128.8(4) . . ?
C00F C00A C00E 123.6(5) . . ?
C00F C00A C00K 119.6(6) . . ?
C00K C00A C00E 116.5(6) . . ?
C008 C00B H00B 120.9 . . ?
C00C C00B C008 118.2(5) . . ?
C00C C00B H00B 120.9 . . ?
C005 C00C C00B 119.1(4) . . ?
C005 C00C H00C 120.4 . . ?
C00B C00C H00C 120.4 . . ?
C008 C00D C009 117.1(4) . . ?
C008 C00D H00D 121.4 . . ?
C009 C00D H00D 121.4 . . ?
C006 C00E C007 101.1(3) . . ?
C006 C00E C00H 109.9(4) . . ?
C00A C00E C006 115.0(4) . . ?
C00A C00E C007 112.2(4) . . ?
C00A C00E C00H 113.8(4) . . ?
C00H C00E C007 103.3(4) . . ?
C00A C00F C00G 124.5(5) . . ?
C00A C00F C00J 122.7(6) . . ?
C00G C00F C00J 112.8(6) . . ?
C00F C00G H00A 109.5 . . ?
C00F C00G H00E 109.5 . . ?
C00F C00G H00F 109.5 . . ?
H00A C00G H00E 109.5 . . ?
H00A C00G H00F 109.5 . . ?
H00E C00G H00F 109.5 . . ?
C009 C00H C00E 105.9(3) . . ?
C009 C00H H00G 110.6 . . ?
C009 C00H H00H 110.6 . . ?
C00E C00H H00G 110.6 . . ?
C00E C00H H00H 110.6 . . ?
H00G C00H H00H 108.7 . . ?
O002 C00I H00I 109.8 . . ?
O002 C00I H00J 109.8 . . ?
O002 C00I C00L 109.2(6) . . ?
H00I C00I H00J 108.3 . . ?
C00L C00I H00I 109.8 . . ?
C00L C00I H00J 109.8 . . ?
C00F C00J H00K 109.5 . . ?
C00F C00J H00L 109.5 . . ?
C00F C00J H00M 109.5 . . ?
H00K C00J H00L 109.5 . . ?
H00K C00J H00M 109.5 . . ?
H00L C00J H00M 109.5 . . ?
C00A C00K H00N 110.2 . . ?
C1 C00K C00A 139.7(11) . . ?
C1 C00K H00N 110.2 . . ?
C00I C00L H00O 109.5 . . ?
C00I C00L H00P 109.5 . . ?
C00I C00L H00Q 109.5 . . ?
H00O C00L H00P 109.5 . . ?
H00O C00L H00Q 109.5 . . ?
H00P C00L H00Q 109.5 . . ?
C00K C1 H1A 120.0 . . ?
C00K C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?

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
Br01 C008 C00B C00C 179.7(4) . . . . ?
Br01 C008 C00D C009 179.2(4) . . . . ?
O002 C006 C00E C007 -79.2(5) . . . . ?
O002 C006 C00E C00A 41.9(5) . . . . ?
O002 C006 C00E C00H 172.0(4) . . . . ?
O003 C007 C00E C006 72.8(6) . . . . ?
O003 C007 C00E C00A -50.3(6) . . . . ?
O003 C007 C00E C00H -173.4(5) . . . . ?
O004 C006 C00E C007 97.5(5) . . . . ?
O004 C006 C00E C00A -141.4(5) . . . . ?
O004 C006 C00E C00H -11.3(6) . . . . ?
C005 C007 C00E C006 -103.8(4) . . . . ?
C005 C007 C00E C00A 133.1(4) . . . . ?
C005 C007 C00E C00H 10.1(5) . . . . ?
C005 C009 C00D C008 1.2(7) . . . . ?
C005 C009 C00H C00E 10.5(5) . . . . ?
C006 O002 C00I C00L -102.6(8) . . . . ?
C006 C00E C00H C009 95.3(5) . . . . ?
C007 C005 C009 C00D 177.5(4) . . . . ?
C007 C005 C009 C00H -4.0(5) . . . . ?
C007 C005 C00C C00B -178.5(4) . . . . ?
C007 C00E C00H C009 -12.0(5) . . . . ?
C008 C00B C00C C005 1.1(7) . . . . ?
C009 C005 C007 O003 179.3(5) . . . . ?
C009 C005 C007 C00E -4.1(5) . . . . ?
C009 C005 C00C C00B 0.6(7) . . . . ?
C00A C00E C00H C009 -134.0(4) . . . . ?
C00B C008 C00D C009 0.6(8) . . . . ?
C00C C005 C007 O003 -1.5(8) . . . . ?
C00C C005 C007 C00E 175.1(4) . . . . ?
C00C C005 C009 C00D -1.8(6) . . . . ?
C00C C005 C009 C00H 176.7(4) . . . . ?
C00D C008 C00B C00C -1.7(8) . . . . ?
C00D C009 C00H C00E -171.2(5) . . . . ?
C00E C00A C00F C00G -0.6(8) . . . . ?
C00E C00A C00F C00J 179.5(5) . . . . ?
C00E C00A C00K C1 -65(2) . . . . ?
C00F C00A C00E C006 42.8(6) . . . . ?
C00F C00A C00E C007 157.7(4) . . . . ?
C00F C00A C00E C00H -85.4(6) . . . . ?
C00F C00A C00K C1 109.8(19) . . . . ?
C00H C009 C00D C008 -177.0(5) . . . . ?
C00I O002 C006 O004 0.7(8) . . . . ?
C00I O002 C006 C00E 177.3(5) . . . . ?
C00K C00A C00E C006 -142.7(5) . . . . ?
C00K C00A C00E C007 -27.8(6) . . . . ?
C00K C00A C00E C00H 89.2(6) . . . . ?
C00K C00A C00F C00G -175.0(6) . . . . ?
C00K C00A C00F C00J 5.1(8) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-09-28
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1480048'
_audit_update_record             
;
2016-05-16 deposited with the CCDC.
2016-09-07 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        lactone
_chemical_formula_moiety         'C16 H13 Br I O3'
_chemical_formula_sum            'C16 H13 Br I O3'
_chemical_formula_weight         460.07
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C64 H52 Br4 I4 O12'
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'
I I -0.3257 6.8362 '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           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                   7.5432(2)
_cell_length_b                   12.7924(3)
_cell_length_c                   17.2791(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1667.36(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6171
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      72.4880
_cell_measurement_theta_min      4.3040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    17.959
_exptl_absorpt_correction_T_max  0.090
_exptl_absorpt_correction_T_min  0.009
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.8069
_exptl_crystal_size_mid          0.6162
_exptl_crystal_size_min          0.4356
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10267
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         4.300
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00  106.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       36.2921    0.0000 -180.0000 139

#__ type_ start__ end____ width___ exp.time_
  2 omega   23.00   90.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -60.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega   23.00   90.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   60.0000 67

#__ type_ start__ end____ width___ exp.time_
  4 omega   10.00  104.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   90.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00   90.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   91.00   1.0000   25.0900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00  109.00   1.0000   25.0900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   91.00   1.0000   25.0900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   91.00   1.0000   25.0900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   91.00   1.0000   25.0900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   98.00   1.0000   25.0900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   40.00   98.00   1.0000   25.0900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00  135.00   1.0000   25.0900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 95

#__ type_ start__ end____ width___ exp.time_
 14 omega   17.00  105.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
 15 omega   20.00  104.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
 16 omega   10.00  104.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
 17 omega   10.00  104.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
 18 omega  -33.00   55.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
 19 omega   70.00  178.00   1.0000   25.0900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000    0.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1138800000
_diffrn_orient_matrix_UB_12      0.0901658000
_diffrn_orient_matrix_UB_13      0.0320625000
_diffrn_orient_matrix_UB_21      -0.1694339000
_diffrn_orient_matrix_UB_22      -0.0622596000
_diffrn_orient_matrix_UB_23      -0.0186518000
_diffrn_orient_matrix_UB_31      0.0060356000
_diffrn_orient_matrix_UB_32      -0.0499425000
_diffrn_orient_matrix_UB_33      0.0810807000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2900
_reflns_number_total             2966
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.153
_refine_ls_abs_structure_details 
;
 Flack x determined using 1111 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2966
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0651
_refine_ls_restrained_S_all      1.070
_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)+(0.1263P)²+2.4765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.1841
_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
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C12(H12), C13(H13), C14(H14), C16(H16)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I1 I 0.91824(14) 0.65917(9) 0.72425(8) 0.0913(5) Uani 1 1 d . . . . .
Br1 Br 0.2773(2) 0.33177(13) 0.46816(8) 0.0749(5) Uani 1 1 d . . . . .
O1 O 0.4659(10) 0.6017(5) 0.8080(4) 0.0450(16) Uani 1 1 d . . . . .
O2 O 0.2707(9) 0.3756(6) 0.8816(5) 0.0486(17) Uani 1 1 d . . . . .
O3 O 0.5125(9) 0.3907(6) 0.9537(4) 0.0445(15) Uani 1 1 d . . . . .
C1 C 0.9082(16) 0.4935(10) 0.7479(9) 0.063(3) Uani 1 1 d . . . . .
H1A H 0.8141 0.4624 0.7174 0.076 Uiso 1 1 calc R . . . .
H1B H 1.0192 0.4618 0.7319 0.076 Uiso 1 1 calc R . . . .
C2 C 0.8771(14) 0.4694(10) 0.8311(8) 0.054(3) Uani 1 1 d . . . . .
H2 H 0.9727 0.4765 0.8646 0.064 Uiso 1 1 calc R . . . .
C3 C 0.7257(12) 0.4391(6) 0.8608(5) 0.0326(16) Uani 1 1 d . . . . .
C4 C 0.7004(13) 0.4195(7) 0.9474(6) 0.040(2) Uani 1 1 d . . . . .
C5 C 0.722(2) 0.5204(12) 0.9943(8) 0.068(3) Uani 1 1 d . . . . .
H5A H 0.6306 0.5690 0.9799 0.102 Uiso 1 1 calc GR . . . .
H5B H 0.8359 0.5505 0.9838 0.102 Uiso 1 1 calc GR . . . .
H5C H 0.7124 0.5048 1.0485 0.102 Uiso 1 1 calc GR . . . .
C6 C 0.806(2) 0.3298(11) 0.9772(8) 0.067(3) Uani 1 1 d . . . . .
H6A H 0.7790 0.3190 1.0309 0.101 Uiso 1 1 calc GR . . . .
H6B H 0.9299 0.3446 0.9715 0.101 Uiso 1 1 calc GR . . . .
H6C H 0.7766 0.2680 0.9484 0.101 Uiso 1 1 calc GR . . . .
C7 C 0.4273(12) 0.3939(6) 0.8879(5) 0.0334(17) Uani 1 1 d . . . . .
C8 C 0.5508(11) 0.4184(6) 0.8203(5) 0.0300(16) Uani 1 1 d . . . . .
C9 C 0.4781(10) 0.5165(6) 0.7783(5) 0.0302(16) Uani 1 1 d . . . . .
C10 C 0.4256(11) 0.4847(6) 0.7004(5) 0.0319(16) Uani 1 1 d . . . . .
C11 C 0.4588(11) 0.3785(7) 0.6901(5) 0.0324(18) Uani 1 1 d . . . . .
C12 C 0.5451(12) 0.3305(7) 0.7597(5) 0.0360(18) Uani 1 1 d . . . . .
H12 H 0.5863 0.2624 0.7651 0.043 Uiso 1 1 calc R . . . .
C13 C 0.3493(14) 0.5455(7) 0.6433(6) 0.041(2) Uani 1 1 d . . . . .
H13 H 0.3295 0.6163 0.6515 0.049 Uiso 1 1 calc R . . . .
C14 C 0.3029(14) 0.4999(9) 0.5741(7) 0.049(2) Uani 1 1 d . . . . .
H14 H 0.2508 0.5388 0.5347 0.058 Uiso 1 1 calc R . . . .
C15 C 0.3370(14) 0.3933(9) 0.5651(6) 0.043(2) Uani 1 1 d . . . . .
C16 C 0.4110(12) 0.3297(7) 0.6209(6) 0.0399(18) Uani 1 1 d . . . . .
H16 H 0.4281 0.2585 0.6128 0.048 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
I1 C1 2.160(13) . ?
Br1 C15 1.905(10) . ?
O1 C9 1.208(11) . ?
O2 C7 1.209(12) . ?
O3 C4 1.469(12) . ?
O3 C7 1.307(12) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.488(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.311(15) . ?
C3 C4 1.529(13) . ?
C3 C8 1.516(12) . ?
C4 C5 1.532(16) . ?
C4 C6 1.489(15) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.525(12) . ?
C8 C9 1.550(10) . ?
C8 C12 1.537(11) . ?
C9 C10 1.461(12) . ?
C10 C11 1.392(12) . ?
C10 C13 1.382(13) . ?
C11 C12 1.499(12) . ?
C11 C16 1.398(13) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.375(16) . ?
C14 H14 0.9300 . ?
C14 C15 1.396(16) . ?
C15 C16 1.379(15) . ?
C16 H16 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
C7 O3 C4 113.6(7) . . ?
I1 C1 H1A 109.0 . . ?
I1 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 I1 113.0(10) . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
C1 C2 H2 117.4 . . ?
C3 C2 C1 125.2(11) . . ?
C3 C2 H2 117.4 . . ?
C2 C3 C4 122.7(9) . . ?
C2 C3 C8 129.0(9) . . ?
C8 C3 C4 108.3(7) . . ?
O3 C4 C3 103.6(7) . . ?
O3 C4 C5 105.9(9) . . ?
O3 C4 C6 107.2(9) . . ?
C3 C4 C5 111.5(9) . . ?
C6 C4 C3 113.5(9) . . ?
C6 C4 C5 114.2(10) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 O3 123.5(9) . . ?
O2 C7 C8 124.6(9) . . ?
O3 C7 C8 111.9(7) . . ?
C3 C8 C7 102.4(7) . . ?
C3 C8 C9 112.5(7) . . ?
C3 C8 C12 117.8(7) . . ?
C7 C8 C9 108.0(6) . . ?
C7 C8 C12 110.7(7) . . ?
C12 C8 C9 105.3(7) . . ?
O1 C9 C8 123.9(8) . . ?
O1 C9 C10 128.5(8) . . ?
C10 C9 C8 107.5(7) . . ?
C11 C10 C9 109.9(8) . . ?
C13 C10 C9 127.9(8) . . ?
C13 C10 C11 122.2(9) . . ?
C10 C11 C12 112.0(8) . . ?
C10 C11 C16 119.9(8) . . ?
C16 C11 C12 128.0(8) . . ?
C8 C12 H12 127.5 . . ?
C11 C12 C8 105.0(7) . . ?
C11 C12 H12 127.5 . . ?
C10 C13 H13 120.4 . . ?
C14 C13 C10 119.3(9) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 121.2 . . ?
C13 C14 C15 117.6(9) . . ?
C15 C14 H14 121.2 . . ?
C14 C15 Br1 117.3(8) . . ?
C16 C15 Br1 117.7(8) . . ?
C16 C15 C14 125.0(9) . . ?
C11 C16 H16 122.0 . . ?
C15 C16 C11 116.0(8) . . ?
C15 C16 H16 122.0 . . ?

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
I1 C1 C2 C3 103.0(13) . . . . ?
Br1 C15 C16 C11 177.8(7) . . . . ?
O1 C9 C10 C11 -178.5(9) . . . . ?
O1 C9 C10 C13 -0.2(15) . . . . ?
O2 C7 C8 C3 177.6(8) . . . . ?
O2 C7 C8 C9 58.8(11) . . . . ?
O2 C7 C8 C12 -56.0(11) . . . . ?
O3 C7 C8 C3 -5.0(9) . . . . ?
O3 C7 C8 C9 -123.9(8) . . . . ?
O3 C7 C8 C12 121.4(8) . . . . ?
C1 C2 C3 C4 -177.6(11) . . . . ?
C1 C2 C3 C8 1.7(18) . . . . ?
C2 C3 C4 O3 178.3(9) . . . . ?
C2 C3 C4 C5 64.9(13) . . . . ?
C2 C3 C4 C6 -65.8(13) . . . . ?
C2 C3 C8 C7 -176.0(10) . . . . ?
C2 C3 C8 C9 -60.3(13) . . . . ?
C2 C3 C8 C12 62.3(13) . . . . ?
C3 C8 C9 O1 -49.3(11) . . . . ?
C3 C8 C9 C10 132.4(7) . . . . ?
C3 C8 C12 C11 -130.5(8) . . . . ?
C4 O3 C7 O2 -177.9(9) . . . . ?
C4 O3 C7 C8 4.7(10) . . . . ?
C4 C3 C8 C7 3.5(8) . . . . ?
C4 C3 C8 C9 119.1(8) . . . . ?
C4 C3 C8 C12 -118.2(8) . . . . ?
C7 O3 C4 C3 -2.2(10) . . . . ?
C7 O3 C4 C5 115.3(10) . . . . ?
C7 O3 C4 C6 -122.4(10) . . . . ?
C7 C8 C9 O1 63.0(11) . . . . ?
C7 C8 C9 C10 -115.4(7) . . . . ?
C7 C8 C12 C11 112.2(7) . . . . ?
C8 C3 C4 O3 -1.1(9) . . . . ?
C8 C3 C4 C5 -114.6(9) . . . . ?
C8 C3 C4 C6 114.8(10) . . . . ?
C8 C9 C10 C11 -0.3(9) . . . . ?
C8 C9 C10 C13 178.0(9) . . . . ?
C9 C8 C12 C11 -4.3(9) . . . . ?
C9 C10 C11 C12 -2.7(10) . . . . ?
C9 C10 C11 C16 177.0(8) . . . . ?
C9 C10 C13 C14 -177.5(9) . . . . ?
C10 C11 C12 C8 4.4(10) . . . . ?
C10 C11 C16 C15 2.0(14) . . . . ?
C10 C13 C14 C15 -0.4(15) . . . . ?
C11 C10 C13 C14 0.6(15) . . . . ?
C12 C8 C9 O1 -178.7(8) . . . . ?
C12 C8 C9 C10 2.9(9) . . . . ?
C12 C11 C16 C15 -178.4(9) . . . . ?
C13 C10 C11 C12 178.9(8) . . . . ?
C13 C10 C11 C16 -1.4(14) . . . . ?
C13 C14 C15 Br1 -178.6(8) . . . . ?
C13 C14 C15 C16 1.1(17) . . . . ?
C14 C15 C16 C11 -1.9(16) . . . . ?
C16 C11 C12 C8 -175.2(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4 1 5 0.1779 4.0000 1.0000 5.0000 -0.2050 -0.8333 0.3796
0 -3 10 0.3591 -0.0000 -3.0000 10.0000 0.0501 0.0003 0.9606
-4 -1 -5 0.2578 -4.0000 -1.0000 -5.0000 0.2050 0.8333 -0.3796
5 -2 2 0.1700 5.0000 -2.0000 2.0000 -0.6856 -0.7600 0.2922
-4 0 5 0.2852 -4.0000 0.0000 5.0000 0.6158 0.5845 0.3813
-4 3 -6 0.2781 -4.0000 3.0000 -6.0000 0.5336 0.6029 -0.6605
-1 4 -10 0.2615 -1.0000 4.0000 -10.0000 0.1539 0.1069 -1.0166
3 -6 -3 0.2568 3.0000 -6.0000 -3.0000 -0.9788 -0.0788 0.0745
-1 6 7 0.2526 -1.0000 6.0000 7.0000 0.8793 -0.3347 0.2619
1 -8 0 0.2201 1.0000 -8.0000 -0.0000 -0.8352 0.3286 0.4056
-3 -7 0 0.1911 -3.0000 -7.0000 -0.0000 -0.2895 0.9441 0.3315
3 5 -4 0.2478 3.0000 5.0000 -4.0000 -0.0191 -0.7450 -0.5559
-3 -1 -9 0.2929 -3.0000 -1.0000 -9.0000 -0.0371 0.7384 -0.6979
-4 -4 -4 0.2527 -4.0000 -4.0000 -4.0000 -0.0334 1.0014 -0.1487
-4 -3 4 0.2779 -4.0000 -3.0000 4.0000 0.3133 0.7899 0.4500

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Et2O/PE
_chemical_properties_physical    
Air-sensitive,Heat-sensitive,Oxygen-sensitive,Light-sensitive,Photo-sensitive
