# 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_AV_7_M_D
_database_code_depnum_ccdc_archive 'CCDC 984338'
_audit_update_record             
;
2016-02-05 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_date             2015-12-16T19:42:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C10  H17  Br1  O2'
_chemical_formula_sum            'C10 H17 Br O2'
_chemical_formula_weight         249.14
_chemical_absolute_configuration rmad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.2235(4)
_cell_length_b                   9.7990(6)
_cell_length_c                   9.2211(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.094(2)
_cell_angle_gamma                90
_cell_volume                     558.04(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      2.226
_cell_measurement_theta_max      25.846
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.652
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_number            15283
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.226
_diffrn_reflns_theta_max         25.846
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_coverage         0.883
_reflns_number_total             2106
_reflns_number_gt                2030
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0837P)²+2.7318P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2106
_refine_ls_number_parameters     68
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1465
_refine_ls_wR_factor_gt          0.1427
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_diff_density_max         2.179
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.16

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.75326(13) 0.64526(15) 0.13240(8) 0.0292(3) Uani 1 1 d . . . . .
O2 O 0.4235(10) 0.6237(8) 0.6088(7) 0.0263(16) Uani 1 1 d . . . . .
O1 O 0.5692(10) 0.5494(6) 0.4185(6) 0.0171(12) Uani 1 1 d . . . . .
C9 C 0.3625(13) 0.4925(9) 0.1348(8) 0.0154(6) Uani 1 1 d . . . . .
H9A H 0.2847 0.4095 0.1568 0.023 Uiso 1 1 calc R U . . .
H9B H 0.3342 0.5121 0.03 0.023 Uiso 1 1 calc R U . . .
H9C H 0.3128 0.5692 0.1901 0.023 Uiso 1 1 calc R U . . .
C5 C 0.9229(13) 0.4448(9) 0.4093(9) 0.0154(6) Uani 1 1 d . . . . .
H5A H 1.009 0.4086 0.3345 0.019 Uiso 1 1 calc R U . . .
H5B H 0.9699 0.5399 0.431 0.019 Uiso 1 1 calc R U . . .
C8 C 0.7349(12) 0.3539(9) 0.0875(9) 0.0154(6) Uani 1 1 d . . . . .
H8A H 0.8931 0.361 0.1037 0.023 Uiso 1 1 calc R U . . .
H8B H 0.6846 0.3673 -0.0165 0.023 Uiso 1 1 calc R U . . .
H8C H 0.6905 0.2634 0.1178 0.023 Uiso 1 1 calc R U . . .
C1 C 0.5276(13) 0.5337(9) 0.5578(8) 0.0154(6) Uani 1 1 d . . . . .
C4 C 0.9679(13) 0.3590(9) 0.5484(9) 0.0154(6) Uani 1 1 d . . . . .
H4A H 1.1262 0.357 0.5781 0.019 Uiso 1 1 calc R U . . .
H4B H 0.9205 0.2642 0.5252 0.019 Uiso 1 1 calc R U . . .
C2 C 0.6061(13) 0.4112(9) 0.6441(9) 0.0154(6) Uani 1 1 d . . . . .
H2A H 0.5579 0.328 0.5884 0.019 Uiso 1 1 calc R U . . .
H2B H 0.5408 0.4099 0.7367 0.019 Uiso 1 1 calc R U . . .
C6 C 0.6824(13) 0.4442(9) 0.3479(8) 0.0154(6) Uani 1 1 d . . . . .
H6 H 0.62 0.3538 0.3709 0.019 Uiso 1 1 calc R U . . .
C3 C 0.8571(13) 0.4088(9) 0.6794(9) 0.0154(6) Uani 1 1 d . . . . .
H3 H 0.8922 0.3403 0.7592 0.019 Uiso 1 1 calc R U . . .
C7 C 0.6300(13) 0.4694(9) 0.1821(9) 0.0154(6) Uani 1 1 d . . . . .
C10 C 0.9442(13) 0.5471(9) 0.7402(8) 0.0154(6) Uani 1 1 d . . . . .
H10A H 0.8965 0.6195 0.6703 0.023 Uiso 1 1 calc R U . . .
H10B H 1.1028 0.5444 0.7558 0.023 Uiso 1 1 calc R U . . .
H10C H 0.8888 0.5653 0.8333 0.023 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C7 1.963(8) . ?
O2 C1 1.223(11) . ?
O1 C1 1.351(9) . ?
O1 C6 1.448(10) . ?
C9 C7 1.683(11) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C5 C4 1.530(11) . ?
C5 C6 1.534(11) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C8 C7 1.615(12) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C1 C2 1.489(12) . ?
C4 C3 1.542(11) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C2 C3 1.556(11) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C6 C7 1.543(10) . ?
C6 H6 1 . ?
C3 C10 1.539(11) . ?
C3 H3 1 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?

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 C6 120.5(6) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C5 C6 112.1(7) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C1 O1 117.1(8) . . ?
O2 C1 C2 122.1(7) . . ?
O1 C1 C2 120.8(7) . . ?
C5 C4 C3 115.5(7) . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
C3 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
C1 C2 C3 112.3(7) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
O1 C6 C5 109.8(6) . . ?
O1 C6 C7 106.0(6) . . ?
C5 C6 C7 116.3(6) . . ?
O1 C6 H6 108.2 . . ?
C5 C6 H6 108.2 . . ?
C7 C6 H6 108.2 . . ?
C10 C3 C4 113.1(7) . . ?
C10 C3 C2 111.2(7) . . ?
C4 C3 C2 112.1(6) . . ?
C10 C3 H3 106.7 . . ?
C4 C3 H3 106.7 . . ?
C2 C3 H3 106.7 . . ?
C6 C7 C8 111.9(7) . . ?
C6 C7 C9 111.1(6) . . ?
C8 C7 C9 114.0(6) . . ?
C6 C7 Br1 109.3(5) . . ?
C8 C7 Br1 107.0(5) . . ?
C9 C7 Br1 103.0(5) . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C6 O1 C1 O2 -177.0(7) . . . . ?
C6 O1 C1 C2 3.0(11) . . . . ?
C6 C5 C4 C3 -62.8(9) . . . . ?
O2 C1 C2 C3 -112.1(9) . . . . ?
O1 C1 C2 C3 67.9(10) . . . . ?
C1 O1 C6 C5 -73.6(9) . . . . ?
C1 O1 C6 C7 160.1(7) . . . . ?
C4 C5 C6 O1 85.8(8) . . . . ?
C4 C5 C6 C7 -154.0(7) . . . . ?
C5 C4 C3 C10 -66.8(9) . . . . ?
C5 C4 C3 C2 59.9(9) . . . . ?
C1 C2 C3 C10 48.2(9) . . . . ?
C1 C2 C3 C4 -79.5(9) . . . . ?
O1 C6 C7 C8 -176.8(6) . . . . ?
C5 C6 C7 C8 61.0(9) . . . . ?
O1 C6 C7 C9 -48.1(8) . . . . ?
C5 C6 C7 C9 -170.4(7) . . . . ?
O1 C6 C7 Br1 64.8(7) . . . . ?
C5 C6 C7 Br1 -57.4(8) . . . . ?

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
C6 H6 O2 1 2.28 3.243(11) 161 2_646


# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3 and Hexane'
####################################################################### 
# 
# 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_AV-96-P
_database_code_depnum_ccdc_archive 'CCDC 984339'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_date             2015-02-26T18:54:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C7  H11  Br  O2'
_chemical_formula_sum            'C7 H11 Br O2'
_chemical_formula_weight         207.07

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_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'
'-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                   13.176(3)
_cell_length_b                   7.6455(17)
_cell_length_c                   15.656(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1577.2(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    302(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      2.602
_cell_measurement_theta_max      26.435
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.149
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      302(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_number            18017
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.602
_diffrn_reflns_theta_max         26.435
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_number_total             1611
_reflns_number_gt                1307
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+3.1471P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1611
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.044
_refine_diff_density_min         -1.066
_refine_diff_density_rms         0.078

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.33182(3) 0.55377(9) 0.56204(3) 0.0734(2) Uani 1 d . .
O2 O 0.46889(19) 0.7551(3) 0.69140(13) 0.0454(6) Uani 1 d . .
O1 O 0.4640(2) 0.7657(4) 0.82881(15) 0.0551(7) Uani 1 d . .
C1 C 0.5127(3) 0.7298(4) 0.7673(2) 0.0389(7) Uani 1 d . .
C6 C 0.5177(3) 0.7113(5) 0.6119(2) 0.0430(8) Uani 1 d . .
H6 H 0.5423 0.5904 0.6141 0.052 Uiso 1 calc . .
C2 C 0.6180(3) 0.6656(5) 0.7709(2) 0.0457(8) Uani 1 d . .
H2A H 0.6221 0.5553 0.7406 0.055 Uiso 1 calc . .
H2B H 0.6359 0.6437 0.8301 0.055 Uiso 1 calc . .
C3 C 0.6945(3) 0.7918(6) 0.7329(3) 0.0560(10) Uani 1 d . .
H3A H 0.6768 0.9096 0.7504 0.067 Uiso 1 calc . .
H3B H 0.761 0.7655 0.7563 0.067 Uiso 1 calc . .
C5 C 0.6047(4) 0.8326(5) 0.5926(2) 0.0561(11) Uani 1 d . .
H5A H 0.6171 0.8315 0.5315 0.067 Uiso 1 calc . .
H5B H 0.5853 0.9507 0.6084 0.067 Uiso 1 calc . .
C4 C 0.7011(3) 0.7867(6) 0.6379(3) 0.0574(11) Uani 1 d . .
H4A H 0.7215 0.67 0.6206 0.069 Uiso 1 calc . .
H4B H 0.7537 0.867 0.6196 0.069 Uiso 1 calc . .
C7 C 0.4357(4) 0.7264(6) 0.5463(2) 0.0605(11) Uani 1 d . .
H7A H 0.4651 0.7129 0.4899 0.073 Uiso 1 calc . .
H7B H 0.4057 0.842 0.5496 0.073 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C7 1.918(5) . ?
O2 C1 1.335(4) . ?
O2 C6 1.440(4) . ?
O1 C1 1.189(4) . ?
C1 C2 1.473(5) . ?
C6 C7 1.494(5) . ?
C6 C5 1.506(6) . ?
C6 H6 0.98 . ?
C2 C3 1.517(5) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C4 1.491(6) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C5 C4 1.496(6) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?

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 O2 C6 122.8(3) . . ?
O1 C1 O2 117.0(3) . . ?
O1 C1 C2 123.6(3) . . ?
O2 C1 C2 119.4(3) . . ?
O2 C6 C7 104.7(3) . . ?
O2 C6 C5 111.7(3) . . ?
C7 C6 C5 111.4(3) . . ?
O2 C6 H6 109.7 . . ?
C7 C6 H6 109.7 . . ?
C5 C6 H6 109.7 . . ?
C1 C2 C3 113.5(3) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 114.4(3) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C4 C5 C6 114.0(3) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C3 C4 C5 114.7(3) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C6 C7 Br1 112.0(3) . . ?
C6 C7 H7A 109.2 . . ?
Br1 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
Br1 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?



# END of CIF
####################################################################### 
# 
# 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_catalyst
_database_code_depnum_ccdc_archive 'CCDC 984340'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_date             2015-03-02T19:00:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14  H14  O2  Se'
_chemical_formula_sum            'C14 H14 O2 Se'
_chemical_formula_weight         293.21

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.1527(10)
_cell_length_b                   26.213(4)
_cell_length_c                   8.0982(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.797(5)
_cell_angle_gamma                90
_cell_volume                     1299.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      2.645
_cell_measurement_theta_max      25.468
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.877
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_number            18829
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.645
_diffrn_reflns_theta_max         25.468
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             2409
_reflns_number_gt                1988
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0250P)²+3.0286P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2409
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.11
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.74
_refine_diff_density_rms         0.069

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.75555(9) 0.72409(2) 0.39807(7) 0.0573(2) Uani 1 d . .
O2 O 0.3478(6) 0.92126(12) 0.5976(4) 0.0622(9) Uani 1 d . .
O1 O 0.2668(7) 0.54109(13) 0.6291(5) 0.0743(11) Uani 1 d . .
C1 C 0.5842(7) 0.66985(16) 0.4782(5) 0.0432(10) Uani 1 d . .
C8 C 0.6094(8) 0.78348(16) 0.4679(5) 0.0455(10) Uani 1 d . .
C6 C 0.4040(8) 0.67615(17) 0.5635(6) 0.0494(11) Uani 1 d . .
H6 H 0.3562 0.7088 0.5863 0.059 Uiso 1 calc . .
C11 C 0.4233(8) 0.87499(16) 0.5504(5) 0.0459(10) Uani 1 d . .
C5 C 0.2928(8) 0.63390(17) 0.6160(6) 0.0509(11) Uani 1 d . .
H5 H 0.172 0.6385 0.6748 0.061 Uiso 1 calc . .
C4 C 0.3607(8) 0.58537(17) 0.5815(6) 0.0511(11) Uani 1 d . .
C9 C 0.7153(7) 0.81506(17) 0.5872(6) 0.0515(11) Uani 1 d . .
H9 H 0.8502 0.8054 0.6402 0.062 Uiso 1 calc . .
C10 C 0.6241(8) 0.86036(17) 0.6282(6) 0.0503(11) Uani 1 d . .
H10 H 0.697 0.8813 0.7084 0.06 Uiso 1 calc . .
C12 C 0.3142(8) 0.84370(18) 0.4323(6) 0.0520(11) Uani 1 d . .
H12 H 0.1778 0.8531 0.3813 0.062 Uiso 1 calc . .
C2 C 0.6520(8) 0.62127(18) 0.4446(6) 0.0551(12) Uani 1 d . .
H2 H 0.7741 0.6167 0.3872 0.066 Uiso 1 calc . .
C13 C 0.4089(8) 0.79857(18) 0.3910(6) 0.0523(12) Uani 1 d . .
H13 H 0.3369 0.7778 0.3099 0.063 Uiso 1 calc . .
C3 C 0.5420(9) 0.57969(18) 0.4946(7) 0.0613(13) Uani 1 d . .
H3 H 0.5895 0.5471 0.47 0.074 Uiso 1 calc . .
C7 C 0.0831(10) 0.5441(2) 0.7174(9) 0.0845(19) Uani 1 d . .
H7A H 0.1243 0.5585 0.825 0.127 Uiso 1 calc . .
H7B H 0.0243 0.5105 0.7296 0.127 Uiso 1 calc . .
H7C H -0.0254 0.5653 0.658 0.127 Uiso 1 calc . .
C14 C 0.1398(10) 0.9377(2) 0.5247(8) 0.0830(18) Uani 1 d . .
H14A H 0.1453 0.943 0.4079 0.125 Uiso 1 calc . .
H14B H 0.1013 0.9691 0.5755 0.125 Uiso 1 calc . .
H14C H 0.0324 0.9122 0.5415 0.125 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Se1 C8 1.912(4) . ?
Se1 C1 1.922(4) . ?
O2 C11 1.367(5) . ?
O2 C14 1.421(6) . ?
O1 C4 1.369(6) . ?
O1 C7 1.400(7) . ?
C1 C6 1.375(6) . ?
C1 C2 1.376(6) . ?
C8 C13 1.382(6) . ?
C8 C9 1.384(6) . ?
C6 C5 1.391(6) . ?
C6 H6 0.93 . ?
C11 C12 1.381(6) . ?
C11 C10 1.383(6) . ?
C5 C4 1.376(6) . ?
C5 H5 0.93 . ?
C4 C3 1.386(7) . ?
C9 C10 1.368(6) . ?
C9 H9 0.93 . ?
C10 H10 0.93 . ?
C12 C13 1.375(6) . ?
C12 H12 0.93 . ?
C2 C3 1.366(7) . ?
C2 H2 0.93 . ?
C13 H13 0.93 . ?
C3 H3 0.93 . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?

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
C8 Se1 C1 102.25(19) . . ?
C11 O2 C14 118.1(4) . . ?
C4 O1 C7 118.8(4) . . ?
C6 C1 C2 119.1(4) . . ?
C6 C1 Se1 125.4(3) . . ?
C2 C1 Se1 115.5(4) . . ?
C13 C8 C9 118.6(4) . . ?
C13 C8 Se1 121.6(3) . . ?
C9 C8 Se1 119.4(3) . . ?
C1 C6 C5 120.3(4) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O2 C11 C12 124.4(4) . . ?
O2 C11 C10 115.6(4) . . ?
C12 C11 C10 120.0(4) . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
O1 C4 C5 125.5(5) . . ?
O1 C4 C3 115.9(4) . . ?
C5 C4 C3 118.6(5) . . ?
C10 C9 C8 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.0(4) . . ?
C9 C10 H10 120 . . ?
C11 C10 H10 120 . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C3 C2 C1 120.7(5) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C12 C13 C8 121.2(4) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?



# END of CIF
####################################################################### 
# 
# 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_Catalyst_NBS
_database_code_depnum_ccdc_archive 'CCDC 984341'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_date             2015-03-12T08:45:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14  H14  Br2  O2  Se'
_chemical_formula_sum            'C14 H14 Br2 O2 Se'
_chemical_formula_weight         453.01

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8195(7)
_cell_length_b                   8.6185(8)
_cell_length_c                   11.8731(11)
_cell_angle_alpha                84.638(4)
_cell_angle_beta                 85.762(4)
_cell_angle_gamma                75.567(4)
_cell_volume                     770.45(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      2.448
_cell_measurement_theta_max      25.401
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.953
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    7.618
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_number            25951
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.448
_diffrn_reflns_theta_max         25.401
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_number_total             2843
_reflns_number_gt                2534
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0945P)²+0.7123P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2843
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.129
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.035
_refine_diff_density_min         -1.456
_refine_diff_density_rms         0.199

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.08094(5) 0.52738(4) 0.81560(3) 0.02826(18) Uani 1 d . .
Br2 Br 0.20838(7) 0.63940(6) 0.97694(4) 0.0415(2) Uani 1 d . .
Br1 Br -0.08113(7) 0.42410(6) 0.67033(4) 0.0428(2) Uani 1 d . .
O1 O 0.6638(4) -0.0801(4) 0.8392(3) 0.0504(9) Uani 1 d . .
O2 O 0.3072(5) 0.9840(4) 0.4537(3) 0.0481(9) Uani 1 d . .
C4 C 0.5283(6) 0.0537(5) 0.8359(4) 0.0345(10) Uani 1 d . .
C10 C 0.2529(6) 0.8878(5) 0.5381(4) 0.0338(9) Uani 1 d . .
C1 C 0.2704(5) 0.3362(5) 0.8191(3) 0.0291(9) Uani 1 d . .
C5 C 0.5745(6) 0.1986(6) 0.8058(4) 0.0384(10) Uani 1 d . .
H5 H 0.6951 0.1996 0.7899 0.046 Uiso 1 calc . .
C7 C 0.1636(5) 0.6694(5) 0.7013(3) 0.0287(9) Uani 1 d . .
C3 C 0.3542(6) 0.0513(5) 0.8602(4) 0.0352(10) Uani 1 d . .
H3 H 0.3236 -0.0474 0.8828 0.042 Uiso 1 calc . .
C11 C 0.3101(6) 0.7230(5) 0.5244(4) 0.0366(10) Uani 1 d . .
H11 H 0.3812 0.6861 0.4592 0.044 Uiso 1 calc . .
C8 C 0.1019(6) 0.8325(5) 0.7145(4) 0.0348(10) Uani 1 d . .
H8 H 0.0295 0.8686 0.7793 0.042 Uiso 1 calc . .
C6 C 0.4458(6) 0.3403(5) 0.7991(4) 0.0346(10) Uani 1 d . .
H6 H 0.4769 0.4398 0.7809 0.042 Uiso 1 calc . .
C9 C 0.1475(6) 0.9425(5) 0.6316(4) 0.0373(10) Uani 1 d . .
H9 H 0.1063 1.0546 0.6394 0.045 Uiso 1 calc . .
C2 C 0.2230(6) 0.1938(5) 0.8518(4) 0.0343(9) Uani 1 d . .
H2 H 0.1024 0.1933 0.8682 0.041 Uiso 1 calc . .
C12 C 0.2627(6) 0.6145(5) 0.6059(4) 0.0332(9) Uani 1 d . .
H12 H 0.2982 0.5026 0.5963 0.04 Uiso 1 calc . .
C13 C 0.6212(8) -0.2312(6) 0.8690(6) 0.0636(17) Uani 1 d . .
H13A H 0.5553 -0.2277 0.9426 0.095 Uiso 1 calc . .
H13B H 0.7304 -0.3166 0.8736 0.095 Uiso 1 calc . .
H13C H 0.5486 -0.2527 0.8113 0.095 Uiso 1 calc . .
C14 C 0.2640(8) 1.1528(6) 0.4663(5) 0.0573(15) Uani 1 d . .
H14A H 0.1352 1.1939 0.4697 0.086 Uiso 1 calc . .
H14B H 0.3158 1.2075 0.4014 0.086 Uiso 1 calc . .
H14C H 0.3113 1.1727 0.5363 0.086 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
Se1 C1 1.921(4) . ?
Se1 C7 1.926(4) . ?
Se1 Br1 2.5585(6) . ?
Se1 Br2 2.5888(6) . ?
O1 C4 1.358(5) . ?
O1 C13 1.430(6) . ?
O2 C10 1.353(5) . ?
O2 C14 1.428(6) . ?
C4 C3 1.376(6) . ?
C4 C5 1.393(6) . ?
C10 C9 1.379(7) . ?
C10 C11 1.400(6) . ?
C1 C2 1.382(6) . ?
C1 C6 1.383(6) . ?
C5 C6 1.376(6) . ?
C5 H5 0.95 . ?
C7 C12 1.377(6) . ?
C7 C8 1.387(6) . ?
C3 C2 1.391(6) . ?
C3 H3 0.95 . ?
C11 C12 1.378(6) . ?
C11 H11 0.95 . ?
C8 C9 1.392(6) . ?
C8 H8 0.95 . ?
C6 H6 0.95 . ?
C9 H9 0.95 . ?
C2 H2 0.95 . ?
C12 H12 0.95 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?

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 Se1 C7 103.47(18) . . ?
C1 Se1 Br1 92.60(12) . . ?
C7 Se1 Br1 91.60(12) . . ?
C1 Se1 Br2 91.89(12) . . ?
C7 Se1 Br2 92.60(12) . . ?
Br1 Se1 Br2 172.98(2) . . ?
C4 O1 C13 117.6(4) . . ?
C10 O2 C14 117.8(4) . . ?
O1 C4 C3 123.6(4) . . ?
O1 C4 C5 116.0(4) . . ?
C3 C4 C5 120.4(4) . . ?
O2 C10 C9 124.4(4) . . ?
O2 C10 C11 115.0(4) . . ?
C9 C10 C11 120.6(4) . . ?
C2 C1 C6 121.3(4) . . ?
C2 C1 Se1 116.0(3) . . ?
C6 C1 Se1 122.5(3) . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
C12 C7 C8 121.3(4) . . ?
C12 C7 Se1 122.3(3) . . ?
C8 C7 Se1 116.0(3) . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C7 C8 C9 119.2(4) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C5 C6 C1 119.2(4) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C7 C12 C11 119.6(4) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?



# END of CIF
####################################################################### 
# 
# 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_AV-356
_database_code_depnum_ccdc_archive 'CCDC 1407583'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_date             2015-02-20T16:03:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11  H11  Br  O4'
_chemical_formula_sum            'C11 H11 Br O4'
_chemical_formula_weight         287.11

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6207(4)
_cell_length_b                   8.4724(3)
_cell_length_c                   12.7806(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.9350(10)
_cell_angle_gamma                90
_cell_volume                     1111.18(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      2.916
_cell_measurement_theta_max      25.719
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.695
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_number            29448
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.916
_diffrn_reflns_theta_max         25.719
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             2119
_reflns_number_gt                1886
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0308P)²+0.8739P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2119
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.035
_refine_ls_R_factor_gt           0.03
_refine_ls_wR_factor_ref         0.0737
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.74381(3) 0.45943(4) 0.29237(3) 0.06122(13) Uani 1 d . .
O2 O 0.47382(14) 0.61718(17) 0.30637(12) 0.0375(3) Uani 1 d . .
O3 O 0.23298(16) 0.55614(19) 0.16029(14) 0.0456(4) Uani 1 d . .
O1 O 0.41843(17) 0.6757(2) 0.45528(14) 0.0505(4) Uani 1 d . .
O4 O 0.03702(16) 0.3580(2) 0.11348(13) 0.0512(4) Uani 1 d . .
C1 C 0.3975(2) 0.5954(3) 0.37514(17) 0.0361(5) Uani 1 d . .
C7 C 0.2141(2) 0.4611(2) 0.24194(17) 0.0337(4) Uani 1 d . .
C6 C 0.1065(2) 0.3603(3) 0.21893(17) 0.0361(5) Uani 1 d . .
C2 C 0.2909(2) 0.4765(3) 0.34744(17) 0.0337(4) Uani 1 d . .
C9 C 0.4680(2) 0.5036(2) 0.22072(18) 0.0373(5) Uani 1 d . .
H9 H 0.464 0.3942 0.249 0.045 Uiso 1 calc . .
C3 C 0.2614(2) 0.3884(3) 0.43009(18) 0.0418(5) Uani 1 d . .
H3 H 0.3135 0.398 0.5024 0.05 Uiso 1 calc . .
C5 C 0.0786(2) 0.2738(3) 0.3019(2) 0.0433(5) Uani 1 d . .
H5 H 0.0057 0.2048 0.2871 0.052 Uiso 1 calc . .
C4 C 0.1566(2) 0.2875(3) 0.4065(2) 0.0473(6) Uani 1 d . .
H4 H 0.1374 0.2263 0.4627 0.057 Uiso 1 calc . .
C10 C 0.5902(3) 0.5236(3) 0.1830(2) 0.0478(6) Uani 1 d . .
H10A H 0.5992 0.6357 0.1642 0.057 Uiso 1 calc . .
H10B H 0.5831 0.4599 0.1168 0.057 Uiso 1 calc . .
C8 C 0.3504(3) 0.5341(3) 0.1271(2) 0.0482(6) Uani 1 d . .
H8A H 0.3667 0.6294 0.0877 0.058 Uiso 1 calc . .
H8B H 0.3388 0.4439 0.0763 0.058 Uiso 1 calc . .
C11 C -0.0720(3) 0.2541(4) 0.0841(2) 0.0650(8) Uani 1 d . .
H11A H -0.0432 0.1455 0.1029 0.097 Uiso 1 calc . .
H11B H -0.1113 0.2614 0.0059 0.097 Uiso 1 calc . .
H11C H -0.1366 0.284 0.1232 0.097 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C10 1.933(3) . ?
O2 C1 1.353(3) . ?
O2 C9 1.447(3) . ?
O3 C7 1.373(3) . ?
O3 C8 1.429(3) . ?
O1 C1 1.201(3) . ?
O4 C6 1.360(3) . ?
O4 C11 1.426(3) . ?
C1 C2 1.489(3) . ?
C7 C2 1.391(3) . ?
C7 C6 1.396(3) . ?
C6 C5 1.382(3) . ?
C2 C3 1.393(3) . ?
C9 C10 1.507(3) . ?
C9 C8 1.513(4) . ?
C9 H9 1 . ?
C3 C4 1.373(3) . ?
C3 H3 0.95 . ?
C5 C4 1.384(4) . ?
C5 H5 0.95 . ?
C4 H4 0.95 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?

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 O2 C9 119.02(16) . . ?
C7 O3 C8 117.31(17) . . ?
C6 O4 C11 117.8(2) . . ?
O1 C1 O2 117.8(2) . . ?
O1 C1 C2 123.3(2) . . ?
O2 C1 C2 118.94(18) . . ?
O3 C7 C2 121.17(19) . . ?
O3 C7 C6 118.09(19) . . ?
C2 C7 C6 120.4(2) . . ?
O4 C6 C5 125.8(2) . . ?
O4 C6 C7 115.02(19) . . ?
C5 C6 C7 119.2(2) . . ?
C7 C2 C3 119.6(2) . . ?
C7 C2 C1 120.95(19) . . ?
C3 C2 C1 119.2(2) . . ?
O2 C9 C10 107.18(18) . . ?
O2 C9 C8 110.50(18) . . ?
C10 C9 C8 109.36(19) . . ?
O2 C9 H9 109.9 . . ?
C10 C9 H9 109.9 . . ?
C8 C9 H9 109.9 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C9 C10 Br1 111.88(17) . . ?
C9 C10 H10A 109.2 . . ?
Br1 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
Br1 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O3 C8 C9 113.17(18) . . ?
O3 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
O3 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?



# END of CIF
