 
data_Compound_10
_publ_requested_journal          'Beilstein J.Org.Chem.'
_publ_contact_author_name        ""Métro, Thomas-Xavier;Frédéric Lamaty"
_publ_contact_author_address     
;Institut des Biomolécules Max Mousseron (IBMM), 
UMR 5247, CNRS, Université de Montpellier, ENSCM, 
Campus Triolet, Place Eugène Bataillon, 
34095 Montpellier Cedex 5, 
France 
;
_publ_contact_author_email       frederic.lamaty@umontpellier.fr
loop_
_publ_author_name
_publ_author_address
"Pétry, Nicolas"
;Institut des Biomolécules Max Mousseron (IBMM), 
UMR 5247, CNRS, Université de Montpellier, ENSCM, 
Campus Triolet, Place Eugène Bataillon, 
34095 Montpellier Cedex 5, 
France 
;
'Benakki, Hafid'
;Institut des Biomolécules Max Mousseron (IBMM), 
UMR 5247, CNRS, Université de Montpellier, ENSCM, 
Campus Triolet, Place Eugène Bataillon, 
34095 Montpellier Cedex 5, 
France 
Laboratory of Chemistry Biology Applied to the Environment, 
aculty of Sciences, Moulay Ismail University 
BP: 11201 
Zitoune Meknès, 
Morocco 
;
'Clot, Eric'
;Institut Charles Gerhardt, UMR 5253 CNRS-UM-ENSCM, 
Université de Montpellier, Place Eugène Bataillon, cc 1501, 
34095 Montpellier Cedex 5, 
France 
;
'Retailleau, Pascal'
;Institut de Chimie des Substances Naturelles, 
CNRS UPR 2301, Université Paris-Saclay, 
1 Avenue de la Terrasse, 
91198 Gif-sur-Yvette, 
France
;
'Asserar, Fatima'
;Laboratory of Chemistry Biology Applied to the Environment, 
aculty of Sciences, Moulay Ismail University 
BP: 11201 
Zitoune Meknès, 
Morocco 
;
'Sekkat, Chakib'
;Laboratory of Chemistry Biology Applied to the Environment, 
aculty of Sciences, Moulay Ismail University 
BP: 11201 
Zitoune Meknès, 
Morocco 
;
"Métro, Thomas-Xavier"
;Institut des Biomolécules Max Mousseron (IBMM), 
UMR 5247, CNRS, Université de Montpellier, ENSCM, 
Campus Triolet, Place Eugène Bataillon, 
34095 Montpellier Cedex 5, 
France 
;
'Martinez, Jean'
;Institut des Biomolécules Max Mousseron (IBMM), 
UMR 5247, CNRS, Université de Montpellier, ENSCM, 
Campus Triolet, Place Eugène Bataillon, 
34095 Montpellier Cedex 5, 
France 
;
"Lamaty, Frédéric"
;Institut des Biomolécules Max Mousseron (IBMM), 
UMR 5247, CNRS, Université de Montpellier, ENSCM, 
Campus Triolet, Place Eugène Bataillon, 
34095 Montpellier Cedex 5, 
France 
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 Br2 O4'
_chemical_formula_sum            'C8 H12 Br2 O4'
_chemical_formula_weight         332.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   4.5421(4)
_cell_length_b                   12.1430(10)
_cell_length_c                   10.5679(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.227(11)
_cell_angle_gamma                90
_cell_volume                     582.87(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    262
_cell_measurement_theta_min      4.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       'small stick'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    6.941
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.652
_exptl_absorpt_process_details           
;
 REQAB (Higashi, 1998)
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku MicroMax003_Mo'
_diffrn_radiation_monochromator  'MaxFlux Confocal'
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 'HPAD Dectris Pilatus 200K'
_diffrn_measurement_device       
;
Rigaku XTALABPRO: Kappa 3 circle Pilatus 200K
;
_diffrn_measurement_device_type  
;
Rigaku microsource Mo Sealed tube
;
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            6277
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.206
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1331
_reflns_number_gt                1026
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0170P)²+0.1990P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1331
_refine_ls_number_parameters     65
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0522
_refine_ls_wR_factor_gt          0.0476
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.76187(6) 0.64092(2) 0.20592(3) 0.04490(10) Uani 1 1 d . . . . .
O1 O 0.9291(5) 0.36223(19) 0.23582(19) 0.0597(6) Uani 1 1 d . . . . .
C1 C 0.5720(6) 0.4604(2) 0.0461(2) 0.0371(6) Uani 1 1 d . . . . .
H1A H 0.473451 0.389770 0.039898 0.045 Uiso 1 1 calc R U . . .
H1B H 0.775292 0.449683 0.021110 0.045 Uiso 1 1 calc R U . . .
O2 O 0.6294(4) 0.42557(18) 0.38609(16) 0.0506(5) Uani 1 1 d . . . . .
C2 C 0.5664(5) 0.4976(2) 0.1818(2) 0.0341(5) Uani 1 1 d . . . . .
H2 H 0.361335 0.503276 0.209580 0.041 Uiso 1 1 calc R U . . .
C3 C 0.7298(5) 0.4200(2) 0.2689(2) 0.0370(6) Uani 1 1 d . . . . .
C4 C 0.7812(8) 0.3589(3) 0.4792(3) 0.0668(9) Uani 1 1 d . . . . .
H4C H 0.764340 0.282556 0.456513 0.100 Uiso 1 1 calc R U . . .
H4D H 0.694751 0.370465 0.560835 0.100 Uiso 1 1 calc R U . . .
H4E H 0.985308 0.379310 0.481913 0.100 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.970(2) . ?
O1 C3 1.199(3) . ?
C1 C2 1.504(3) . ?
C1 C1 1.515(5) 3_665 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O2 C3 1.323(3) . ?
O2 C4 1.447(3) . ?
C2 C3 1.510(3) . ?
C2 H2 0.9800 . ?
C4 H4C 0.9600 . ?
C4 H4D 0.9600 . ?
C4 H4E 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C1 114.5(3) . 3_665 ?
C2 C1 H1A 108.6 . . ?
C1 C1 H1A 108.6 3_665 . ?
C2 C1 H1B 108.6 . . ?
C1 C1 H1B 108.6 3_665 . ?
H1A C1 H1B 107.6 . . ?
C3 O2 C4 116.3(2) . . ?
C1 C2 C3 112.6(2) . . ?
C1 C2 Br1 112.26(18) . . ?
C3 C2 Br1 104.58(16) . . ?
C1 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
Br1 C2 H2 109.1 . . ?
O1 C3 O2 124.5(2) . . ?
O1 C3 C2 123.9(2) . . ?
O2 C3 C2 111.6(2) . . ?
O2 C4 H4C 109.5 . . ?
O2 C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
O2 C4 H4E 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 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
C1 C1 C2 C3 -176.2(3) 3_665 . . . ?
C1 C1 C2 Br1 -58.5(3) 3_665 . . . ?
C4 O2 C3 O1 2.0(4) . . . . ?
C4 O2 C3 C2 -176.8(2) . . . . ?
C1 C2 C3 O1 26.9(4) . . . . ?
Br1 C2 C3 O1 -95.3(3) . . . . ?
C1 C2 C3 O2 -154.3(2) . . . . ?
Br1 C2 C3 O2 83.5(2) . . . . ?

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.061




