 
data_Compound_19

_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           'C14 H18 N2 O6' 
_chemical_formula_sum
 'C14 H18 N2 O6' 
_chemical_formula_weight          310.30

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'
 'N'  'N'   0.0311   0.0180
 '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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            5
_space_group_name_H-M_alt         'C 2'
_space_group_name_Hall            'C 2y'
 
_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, -z'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z'
 
_cell_length_a                    12.5371(10)
_cell_length_b                    5.8884(5)
_cell_length_c                    10.3764(7)
_cell_angle_alpha                 90
_cell_angle_beta                  105.615(9)
_cell_angle_gamma                 90
_cell_volume                      737.75(10)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used           2158
_cell_measurement_theta_min             4.4
_cell_measurement_theta_max             70.5
 
_exptl_crystal_description        'thick plate'
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.397          
_exptl_crystal_F_000              328
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.31
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.09
_exptl_absorpt_coefficient_mu     0.933
_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         0.777
_exptl_absorpt_process_details    'REQAB (Higashi, 1998)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      1.54187
_diffrn_radiation_type            CuK\a
_diffrn_source                          'Rigaku Rotating Anode'
_diffrn_radiation_monochromator         'Osmic Confocal CMF mirrors'
_diffrn_measurement_specimen_support    'Fiber'
_diffrn_detector                        'Rigaku Rapid 2 curved IP'
_diffrn_measurement_device
;
Crystal Goniometer -chi-partial
;
_diffrn_measurement_device_type
;
Rigaku mm007HF 
;
_diffrn_detector_area_resol_mean        10.0000
_diffrn_measurement_method              'profile data from ω-scans'
_diffrn_reflns_number             4789
_diffrn_reflns_av_unetI/netI      0.0364
_diffrn_reflns_av_R_equivalents   0.0476
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        6
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          4.424
_diffrn_reflns_theta_max          72.098
_diffrn_reflns_theta_full         67.687
_diffrn_measured_fraction_theta_max   0.969
_diffrn_measured_fraction_theta_full  0.982
_diffrn_reflns_Laue_measured_fraction_max    0.969
_diffrn_reflns_Laue_measured_fraction_full   0.982
_diffrn_reflns_point_group_measured_fraction_max   0.977
_diffrn_reflns_point_group_measured_fraction_full  0.989
_reflns_number_total              1341
_reflns_number_gt                 1093
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.829
_reflns_Friedel_fraction_max      0.986
_reflns_Friedel_fraction_full     0.998
 
_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 2.0 r16 (Rigaku, 2014)
;
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_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
;
 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)+(0.0449P)²+0.0602P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    direct
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef        0.0033(10)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack    0.0(4)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          1339
_refine_ls_number_parameters      103
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0462
_refine_ls_R_factor_gt            0.0346
_refine_ls_wR_factor_ref          0.0968
_refine_ls_wR_factor_gt           0.0813
_refine_ls_goodness_of_fit_ref    1.111
_refine_ls_restrained_S_all       1.110
_refine_ls_shift/su_max           0.000
_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
C1 C 0.5939(2) 0.2031(5) 0.9500(3) 0.0499(7) Uani 1 1 d . . . . .
H1 H 0.601629 0.038033 0.944311 0.060 Uiso 1 1 calc R U . . .
N1 N 0.48410(17) 0.2715(4) 0.8667(2) 0.0473(6) Uani 1 1 d . . . . .
O1 O 0.4639(2) 0.7305(4) 0.7710(2) 0.0811(8) Uani 1 1 d . . . . .
C2 C 0.6707(2) 0.3184(6) 0.8790(3) 0.0615(9) Uani 1 1 d . . . . .
H2A H 0.741521 0.241294 0.896994 0.074 Uiso 1 1 calc R U . . .
H2B H 0.682786 0.476434 0.905302 0.074 Uiso 1 1 calc R U . . .
O2 O 0.39045(17) 0.5853(3) 0.56806(18) 0.0602(6) Uani 1 1 d . . . . .
C3 C 0.6064(3) 0.2963(6) 0.7325(3) 0.0694(9) Uani 1 1 d . . . . .
H3A H 0.617028 0.147233 0.698197 0.083 Uiso 1 1 calc R U . . .
H3B H 0.629839 0.410618 0.678567 0.083 Uiso 1 1 calc R U . . .
O3 O 0.29991(15) 0.3164(4) 0.8303(2) 0.0671(7) Uani 1 1 d . . . . .
C4 C 0.4857(3) 0.3317(5) 0.7312(3) 0.0536(8) Uani 1 1 d . . . . .
H4 H 0.438686 0.226173 0.667496 0.064 Uiso 1 1 calc R U . . .
C5 C 0.4455(2) 0.5727(5) 0.6973(3) 0.0519(8) Uani 1 1 d . . . . .
C7 C 0.3907(2) 0.2694(5) 0.9057(3) 0.0493(7) Uani 1 1 d . . . . .
C6 C 0.3490(3) 0.8047(6) 0.5199(3) 0.0745(10) Uani 1 1 d . . . . .
H6A H 0.306841 0.793038 0.428021 0.112 Uiso 1 1 calc R U . . .
H6B H 0.409877 0.907009 0.526855 0.112 Uiso 1 1 calc R U . . .
H6C H 0.302388 0.861125 0.572537 0.112 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
C1 N1 1.471(3) . ?
C1 C7 1.508(4) 2_657 ?
C1 C2 1.521(4) . ?
C1 H1 0.9800 . ?
N1 C7 1.339(3) . ?
N1 C4 1.455(4) . ?
O1 C5 1.186(3) . ?
C2 C3 1.523(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O2 C5 1.335(3) . ?
O2 C6 1.431(4) . ?
C3 C4 1.523(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O3 C7 1.227(3) . ?
C4 C5 1.516(4) . ?
C4 H4 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 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
N1 C1 C7 111.2(2) . 2_657 ?
N1 C1 C2 102.0(2) . . ?
C7 C1 C2 115.9(2) 2_657 . ?
N1 C1 H1 109.2 . . ?
C7 C1 H1 109.2 2_657 . ?
C2 C1 H1 109.2 . . ?
C7 N1 C4 122.4(2) . . ?
C7 N1 C1 125.2(2) . . ?
C4 N1 C1 112.3(2) . . ?
C1 C2 C3 102.2(2) . . ?
C1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
C1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C5 O2 C6 116.2(2) . . ?
C2 C3 C4 104.8(2) . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C4 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
N1 C4 C5 111.2(2) . . ?
N1 C4 C3 103.3(2) . . ?
C5 C4 C3 113.4(3) . . ?
N1 C4 H4 109.6 . . ?
C5 C4 H4 109.6 . . ?
C3 C4 H4 109.6 . . ?
O1 C5 O2 124.2(3) . . ?
O1 C5 C4 126.1(2) . . ?
O2 C5 C4 109.6(2) . . ?
O3 C7 N1 122.8(3) . . ?
O3 C7 C1 122.8(3) . 2_657 ?
N1 C7 C1 114.4(2) . 2_657 ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
 
_refine_diff_density_max    0.156
_refine_diff_density_min   -0.172
_refine_diff_density_rms    0.035





