 
data_Compound_15a

_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           'C12 H16 N2 O4' 
_chemical_formula_sum
 'C12 H16 N2 O4' 
_chemical_formula_weight          252.27

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'
 'N'  'N'   0.0061   0.0033
 '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       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
 
_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+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    5.8495(4)
_cell_length_b                    9.7200(7)
_cell_length_c                    21.3731(15)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1215.21(15)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     333
_cell_measurement_theta_min       3.5
_cell_measurement_theta_max       27.5
 
_exptl_crystal_description        stick
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.379          
_exptl_crystal_F_000              536
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.31
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.06
_exptl_absorpt_coefficient_mu     0.104
_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         0.848
_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             21483
_diffrn_reflns_av_unetI/netI      0.0159
_diffrn_reflns_av_R_equivalents   0.0292
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        7
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -27
_diffrn_reflns_limit_l_max        27
_diffrn_reflns_theta_min          4.301
_diffrn_reflns_theta_max          27.477
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.989
_diffrn_measured_fraction_theta_full  0.986
_diffrn_reflns_Laue_measured_fraction_max    0.989
_diffrn_reflns_Laue_measured_fraction_full   0.986
_diffrn_reflns_point_group_measured_fraction_max   0.991
_diffrn_reflns_point_group_measured_fraction_full  0.989
_reflns_number_total              2772
_reflns_number_gt                 2519
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.705
_reflns_Friedel_fraction_max      0.994
_reflns_Friedel_fraction_full     0.993
 
_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 (Sheldrick, 2015)'
_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)+(0.0664P)²+0.0182P] 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_abs_structure_details
;
 Flack x determined using 995 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.1(2)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          2765
_refine_ls_number_parameters      183
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0346
_refine_ls_R_factor_gt            0.0312
_refine_ls_wR_factor_ref          0.0925
_refine_ls_wR_factor_gt           0.0902
_refine_ls_goodness_of_fit_ref    1.051
_refine_ls_restrained_S_all       1.060
_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
C1 C 0.6920(3) 0.34070(17) 0.69111(8) 0.0448(4) Uani 1 1 d . . . . .
H1 H 0.582133 0.266090 0.697905 0.054 Uiso 1 1 calc DR U . A 1
C2 C 0.8557(17) 0.3541(11) 0.7487(5) 0.067(2) Uani 0.652(12) 1 d . . P B 1
H2A H 0.930383 0.443178 0.749925 0.081 Uiso 0.652(12) 1 calc R U P B 1
H2B H 0.776191 0.338188 0.787827 0.081 Uiso 0.652(12) 1 calc R U P B 1
C3 C 1.0237(9) 0.2389(6) 0.73386(17) 0.0695(14) Uani 0.652(12) 1 d . . P B 1
H3A H 1.165528 0.251447 0.756690 0.083 Uiso 0.652(12) 1 calc R U P B 1
H3B H 0.959451 0.150061 0.744712 0.083 Uiso 0.652(12) 1 calc R U P B 1
C2B C 0.833(3) 0.3198(18) 0.7457(9) 0.061(4) Uani 0.348(12) 1 d . . P B 2
H2B1 H 0.793428 0.232871 0.765214 0.073 Uiso 0.348(12) 1 calc DR U P B 2
H2B2 H 0.804556 0.392626 0.775729 0.073 Uiso 0.348(12) 1 calc R U P B 2
C3B C 1.0781(11) 0.3191(13) 0.7284(3) 0.062(3) Uani 0.348(12) 1 d . . P B 2
H3B1 H 1.168844 0.265952 0.757728 0.075 Uiso 0.348(12) 1 calc R U P B 2
H3B2 H 1.139503 0.411547 0.725362 0.075 Uiso 0.348(12) 1 calc R U P B 2
C4 C 1.0638(3) 0.2491(2) 0.66432(11) 0.0623(5) Uani 1 1 d . . . . .
H4A H 1.190646 0.310167 0.655153 0.075 Uiso 0.652(12) 1 calc R U P B 1
H4B H 1.095174 0.159394 0.646441 0.075 Uiso 0.652(12) 1 calc R U P B 1
H4C H 1.192120 0.274169 0.637931 0.075 Uiso 0.348(12) 1 calc R U P B 2
H4D H 1.057143 0.149810 0.668256 0.075 Uiso 0.348(12) 1 calc R U P B 2
C5 C 0.8233(3) 0.34391(17) 0.58023(8) 0.0471(4) Uani 1 1 d . . . . .
C6 C 0.5934(3) 0.40889(16) 0.56653(7) 0.0423(3) Uani 1 1 d . . . . .
H6 H 0.479307 0.336196 0.560633 0.051 Uiso 1 1 calc R U . . .
C7 C 0.5879(4) 0.50534(18) 0.51053(7) 0.0559(4) Uani 1 1 d . . . . .
H7A H 0.731548 0.554180 0.506093 0.067 Uiso 1 1 calc R U . . .
H7B H 0.556430 0.455374 0.472193 0.067 Uiso 1 1 calc R U . . .
C8 C 0.3943(4) 0.60351(18) 0.52625(8) 0.0560(4) Uani 1 1 d . . . . .
H8A H 0.247013 0.562582 0.516823 0.067 Uiso 1 1 calc R U . . .
H8B H 0.409208 0.688971 0.503168 0.067 Uiso 1 1 calc R U . . .
C9 C 0.4214(3) 0.62794(15) 0.59713(7) 0.0432(3) Uani 1 1 d . . . . .
H9 H 0.272688 0.644060 0.616940 0.052 Uiso 1 1 calc R U . . .
C10 C 0.5675(3) 0.47487(15) 0.67899(7) 0.0402(3) Uani 1 1 d . . . . .
C11 C 0.5836(3) 0.74612(16) 0.60977(7) 0.0449(4) Uani 1 1 d . . . . .
C12 C 0.5957(5) 0.9889(2) 0.61959(10) 0.0767(7) Uani 1 1 d . . . . .
H12A H 0.494433 1.066548 0.618042 0.115 Uiso 0.42(4) 1 calc R U P . .
H12B H 0.667605 0.984896 0.659932 0.115 Uiso 0.42(4) 1 calc R U P . .
H12C H 0.710580 0.998236 0.587788 0.115 Uiso 0.42(4) 1 calc R U P . .
H12D H 0.753979 0.966572 0.625799 0.115 Uiso 0.58(4) 1 calc R U P . .
H12E H 0.580807 1.048224 0.583909 0.115 Uiso 0.58(4) 1 calc R U P . .
H12F H 0.537831 1.034884 0.656053 0.115 Uiso 0.58(4) 1 calc R U P . .
N13 N 0.8489(2) 0.30516(14) 0.64020(7) 0.0470(3) Uani 1 1 d . . . . .
N14 N 0.5212(2) 0.49872(12) 0.61848(5) 0.0406(3) Uani 1 1 d . . . . .
O15 O 0.5097(3) 0.55268(13) 0.72096(5) 0.0572(4) Uani 1 1 d . . . . .
O16 O 0.9682(3) 0.32554(17) 0.53995(7) 0.0703(4) Uani 1 1 d . . . . .
O17 O 0.7870(2) 0.73588(16) 0.61627(7) 0.0650(4) Uani 1 1 d . . . . .
O18 O 0.4672(3) 0.86412(12) 0.60908(7) 0.0622(4) Uani 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C2B 1.443(18) . ?
C1 N13 1.465(2) . ?
C1 C10 1.516(2) . ?
C1 C2 1.564(9) . ?
C1 H1 0.9800 . ?
C2 C3 1.523(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.508(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2B C3B 1.48(2) . ?
C2B H2B1 0.9700 . ?
C2B H2B2 0.9700 . ?
C3B C4 1.532(7) . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
C4 N13 1.463(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C4 H4D 0.9700 . ?
C5 O16 1.221(2) . ?
C5 N13 1.344(2) . ?
C5 C6 1.514(2) . ?
C6 N14 1.4743(18) . ?
C6 C7 1.521(2) . ?
C6 H6 0.9800 . ?
C7 C8 1.518(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.542(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N14 1.4583(19) . ?
C9 C11 1.514(2) . ?
C9 H9 0.9800 . ?
C10 O15 1.2211(19) . ?
C10 N14 1.3416(18) . ?
C11 O17 1.202(2) . ?
C11 O18 1.334(2) . ?
C12 O18 1.445(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H12D 0.9600 . ?
C12 H12E 0.9600 . ?
C12 H12F 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
C2B C1 N13 102.1(8) . . ?
C2B C1 C10 122.3(8) . . ?
N13 C1 C10 112.15(12) . . ?
N13 C1 C2 102.7(4) . . ?
C10 C1 C2 110.9(4) . . ?
N13 C1 H1 110.3 . . ?
C10 C1 H1 110.3 . . ?
C2 C1 H1 110.3 . . ?
C3 C2 C1 99.8(7) . . ?
C3 C2 H2A 111.8 . . ?
C1 C2 H2A 111.8 . . ?
C3 C2 H2B 111.8 . . ?
C1 C2 H2B 111.8 . . ?
H2A C2 H2B 109.5 . . ?
C4 C3 C2 104.9(4) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.8 . . ?
C1 C2B C3B 110.6(12) . . ?
C1 C2B H2B1 109.5 . . ?
C3B C2B H2B1 109.5 . . ?
C1 C2B H2B2 109.5 . . ?
C3B C2B H2B2 109.5 . . ?
H2B1 C2B H2B2 108.1 . . ?
C2B C3B C4 99.9(9) . . ?
C2B C3B H3B1 111.8 . . ?
C4 C3B H3B1 111.8 . . ?
C2B C3B H3B2 111.8 . . ?
C4 C3B H3B2 111.8 . . ?
H3B1 C3B H3B2 109.5 . . ?
N13 C4 C3 103.8(2) . . ?
N13 C4 C3B 101.4(3) . . ?
N13 C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
N13 C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
N13 C4 H4C 111.5 . . ?
C3B C4 H4C 111.5 . . ?
N13 C4 H4D 111.5 . . ?
C3B C4 H4D 111.5 . . ?
H4C C4 H4D 109.3 . . ?
O16 C5 N13 123.62(17) . . ?
O16 C5 C6 122.74(16) . . ?
N13 C5 C6 113.61(14) . . ?
N14 C6 C5 110.84(12) . . ?
N14 C6 C7 102.80(12) . . ?
C5 C6 C7 115.36(15) . . ?
N14 C6 H6 109.2 . . ?
C5 C6 H6 109.2 . . ?
C7 C6 H6 109.2 . . ?
C8 C7 C6 103.25(14) . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
C6 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
C7 C8 C9 103.74(14) . . ?
C7 C8 H8A 111.0 . . ?
C9 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C9 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
N14 C9 C11 110.29(13) . . ?
N14 C9 C8 102.47(12) . . ?
C11 C9 C8 110.89(14) . . ?
N14 C9 H9 111.0 . . ?
C11 C9 H9 111.0 . . ?
C8 C9 H9 111.0 . . ?
O15 C10 N14 123.04(14) . . ?
O15 C10 C1 122.71(14) . . ?
N14 C10 C1 114.23(13) . . ?
O17 C11 O18 125.29(17) . . ?
O17 C11 C9 125.32(16) . . ?
O18 C11 C9 109.30(15) . . ?
O18 C12 H12A 109.5 . . ?
O18 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O18 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O18 C12 H12D 109.5 . . ?
H12A C12 H12D 141.1 . . ?
H12B C12 H12D 56.3 . . ?
H12C C12 H12D 56.3 . . ?
O18 C12 H12E 109.5 . . ?
H12A C12 H12E 56.3 . . ?
H12B C12 H12E 141.1 . . ?
H12C C12 H12E 56.3 . . ?
H12D C12 H12E 109.5 . . ?
O18 C12 H12F 109.5 . . ?
H12A C12 H12F 56.3 . . ?
H12B C12 H12F 56.3 . . ?
H12C C12 H12F 141.1 . . ?
H12D C12 H12F 109.5 . . ?
H12E C12 H12F 109.5 . . ?
C5 N13 C4 122.42(16) . . ?
C5 N13 C1 124.90(13) . . ?
C4 N13 C1 111.35(15) . . ?
C10 N14 C9 122.09(12) . . ?
C10 N14 C6 124.47(13) . . ?
C9 N14 C6 112.90(11) . . ?
C11 O18 C12 117.04(18) . . ?
 
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
N13 C1 C2 C3 -36.8(6) . . . . ?
C10 C1 C2 C3 -156.8(5) . . . . ?
C1 C2 C3 C4 41.1(7) . . . . ?
N13 C1 C2B C3B 18.7(14) . . . . ?
C10 C1 C2B C3B -107.5(13) . . . . ?
C1 C2B C3B C4 -35.3(15) . . . . ?
C2 C3 C4 N13 -29.7(7) . . . . ?
C2B C3B C4 N13 36.2(10) . . . . ?
O16 C5 C6 N14 -142.53(16) . . . . ?
N13 C5 C6 N14 39.31(19) . . . . ?
O16 C5 C6 C7 -26.3(2) . . . . ?
N13 C5 C6 C7 155.59(14) . . . . ?
N14 C6 C7 C8 -32.20(16) . . . . ?
C5 C6 C7 C8 -152.96(13) . . . . ?
C6 C7 C8 C9 38.97(17) . . . . ?
C7 C8 C9 N14 -29.94(18) . . . . ?
C7 C8 C9 C11 87.74(16) . . . . ?
C2B C1 C10 O15 -26.5(8) . . . . ?
N13 C1 C10 O15 -148.09(17) . . . . ?
C2 C1 C10 O15 -33.9(5) . . . . ?
C2B C1 C10 N14 155.2(8) . . . . ?
N13 C1 C10 N14 33.58(19) . . . . ?
C2 C1 C10 N14 147.8(4) . . . . ?
N14 C9 C11 O17 23.1(2) . . . . ?
C8 C9 C11 O17 -89.7(2) . . . . ?
N14 C9 C11 O18 -160.36(13) . . . . ?
C8 C9 C11 O18 86.84(17) . . . . ?
O16 C5 N13 C4 6.3(3) . . . . ?
C6 C5 N13 C4 -175.60(16) . . . . ?
O16 C5 N13 C1 171.93(16) . . . . ?
C6 C5 N13 C1 -9.9(2) . . . . ?
C3 C4 N13 C5 172.6(3) . . . . ?
C3B C4 N13 C5 139.5(5) . . . . ?
C3 C4 N13 C1 5.2(3) . . . . ?
C3B C4 N13 C1 -28.0(5) . . . . ?
C2B C1 N13 C5 -160.2(7) . . . . ?
C10 C1 N13 C5 -27.6(2) . . . . ?
C2 C1 N13 C5 -146.7(4) . . . . ?
C2B C1 N13 C4 6.9(7) . . . . ?
C10 C1 N13 C4 139.46(15) . . . . ?
C2 C1 N13 C4 20.3(4) . . . . ?
O15 C10 N14 C9 7.4(2) . . . . ?
C1 C10 N14 C9 -174.24(14) . . . . ?
O15 C10 N14 C6 178.38(16) . . . . ?
C1 C10 N14 C6 -3.3(2) . . . . ?
C11 C9 N14 C10 63.7(2) . . . . ?
C8 C9 N14 C10 -178.15(15) . . . . ?
C11 C9 N14 C6 -108.15(14) . . . . ?
C8 C9 N14 C6 9.95(18) . . . . ?
C5 C6 N14 C10 -34.0(2) . . . . ?
C7 C6 N14 C10 -157.77(16) . . . . ?
C5 C6 N14 C9 137.71(14) . . . . ?
C7 C6 N14 C9 13.90(18) . . . . ?
O17 C11 O18 C12 -2.7(3) . . . . ?
C9 C11 O18 C12 -179.26(15) . . . . ?
 
_refine_diff_density_max    0.154
_refine_diff_density_min   -0.134
_refine_diff_density_rms    0.029





