data_publication_text
_publ_requested_journal          'Beilstein Journal of organic chemistry'
_publ_contact_author_name        'Laurent J. Jouffret'
_publ_contact_author_address     
'CNRS, UMR 6296, ICCF, F-63178 Aubière Cedex, France'
_publ_contact_author_email       laurent.jouffret@uca.fr
loop_
_publ_author_name
_publ_author_address
;
'Pypec, Maxime'
;

;
'Universite Clermont Auvergne, Institut de Chimie de Clermont-Ferrand,' 
'BP 10448, F-63000 Clermont-Ferrand, France and CNRS, UMR 6296, ICCF, F-63178 Aubiere Cedex, France'
;

;
'Jouffret, Laurent'
;

;
'Universite Clermont Auvergne, Institut de Chimie de Clermont-Ferrand,' 
'BP 10448, F-63000 Clermont-Ferrand, France and CNRS, UMR 6296, ICCF, F-63178 Aubiere Cedex, France'
;

;
'Taillefumier, Claude'
;

;
'Universite Clermont Auvergne, Institut de Chimie de Clermont-Ferrand,' 
'BP 10448, F-63000 Clermont-Ferrand, France and CNRS, UMR 6296, ICCF, F-63178 Aubiere Cedex, France'
;

;
'Roy, Olivier'
;

;
'Universite Clermont Auvergne, Institut de Chimie de Clermont-Ferrand,' 
'BP 10448, F-63000 Clermont-Ferrand, France and CNRS, UMR 6296, ICCF, F-63178 Aubiere Cedex, France'
;

 
data_MP420
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_formula_sum
 'C15 H22 N4 O4' 
_chemical_formula_weight          322.36

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            61
_space_group_name_H-M_alt         'P b c a'
_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+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x+1/2, -y, z+1/2'
 '-x, -y, -z'
 '-x-1/2, y-1/2, z'
 'x, -y-1/2, z-1/2'
 'x-1/2, y, -z-1/2'
 
_cell_length_a                    10.3108(12)
_cell_length_b                    11.2142(12)
_cell_length_c                    28.442(3)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      3288.7(6)
_cell_formula_units_Z             8
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     541
_cell_measurement_theta_min       2.63
_cell_measurement_theta_max       24.31
 
_exptl_crystal_description        rod
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.302          
_exptl_crystal_F_000              1376
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.624
_exptl_crystal_size_mid           0.142
_exptl_crystal_size_min           0.134
_exptl_absorpt_coefficient_mu     0.096
_shelx_estimated_absorpt_T_min    0.943
_shelx_estimated_absorpt_T_max    0.987
_exptl_absorpt_correction_type    numerical
_exptl_absorpt_correction_T_min   0.9197  
_exptl_absorpt_correction_T_max   1.0000
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_diffrn_ambient_temperature       173(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    molybdene
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             122188
_diffrn_reflns_av_unetI/netI      0.0312
_diffrn_reflns_av_R_equivalents   0.0796
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -40
_diffrn_reflns_limit_l_max        40
_diffrn_reflns_theta_min          2.778
_diffrn_reflns_theta_max          30.506
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              5015
_reflns_number_gt                 3393
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0396P)²+1.1109P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          5015
_refine_ls_number_parameters      219
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0753
_refine_ls_R_factor_gt            0.0410
_refine_ls_wR_factor_ref          0.1042
_refine_ls_wR_factor_gt           0.0889
_refine_ls_goodness_of_fit_ref    1.005
_refine_ls_restrained_S_all       1.005
_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
O1 O 0.23723(9) 0.37377(8) 0.64455(3) 0.0274(2) Uani 1 1 d . . . . .
O2 O 0.34197(8) 0.53731(7) 0.51078(3) 0.02509(19) Uani 1 1 d . . . . .
O3 O 0.16219(9) 0.62881(8) 0.40681(3) 0.0322(2) Uani 1 1 d . . . . .
O4 O 0.28570(9) 0.23785(8) 0.58921(3) 0.0308(2) Uani 1 1 d . . . . .
N1 N 0.19208(10) 0.39190(9) 0.51903(3) 0.0215(2) Uani 1 1 d . . . . .
N2 N 0.13331(10) 0.29388(9) 0.49668(4) 0.0226(2) Uani 1 1 d . . . . .
H10 H 0.1592(14) 0.2291(14) 0.5109(5) 0.034(4) Uiso 1 1 d . . . . .
N3 N 0.47836(10) 0.51133(10) 0.40615(4) 0.0258(2) Uani 1 1 d . . . . .
H11 H 0.5182(15) 0.4997(14) 0.4334(6) 0.036(4) Uiso 1 1 d . . . . .
C1 C 0.35167(15) 0.70303(12) 0.36809(5) 0.0329(3) Uani 1 1 d . . . . .
H14 H 0.293292 0.766898 0.357837 0.049 Uiso 1 1 calc R U . . .
H13 H 0.386630 0.661699 0.340502 0.049 Uiso 1 1 calc R U . . .
H1 H 0.423138 0.737263 0.386361 0.049 Uiso 1 1 calc R U . . .
C2 C 0.27802(12) 0.61597(11) 0.39809(4) 0.0243(3) Uani 1 1 d . . . . .
N4 N 0.34383(10) 0.52029(9) 0.41434(3) 0.0229(2) Uani 1 1 d . . . . .
C4 C 0.27706(12) 0.42942(10) 0.44125(4) 0.0224(2) Uani 1 1 d . . . . .
H4A H 0.320856 0.351797 0.436484 0.027 Uiso 1 1 calc R U . . .
H4B H 0.186928 0.421917 0.429617 0.027 Uiso 1 1 calc R U . . .
C5 C 0.27471(11) 0.45849(10) 0.49340(4) 0.0189(2) Uani 1 1 d . . . . .
C6 C 0.16960(12) 0.41735(11) 0.56840(4) 0.0234(2) Uani 1 1 d . . . . .
H21 H 0.075347 0.413448 0.574849 0.028 Uiso 1 1 calc R U . . .
H20 H 0.199182 0.499462 0.575366 0.028 Uiso 1 1 calc R U . . .
C7 C 0.23911(12) 0.33153(11) 0.60033(4) 0.0217(2) Uani 1 1 d . . . . .
C8 C 0.29476(15) 0.29743(12) 0.67966(4) 0.0334(3) Uani 1 1 d . . . . .
H5 H 0.374021 0.259616 0.666869 0.040 Uiso 1 1 calc R U . . .
H6 H 0.233031 0.233574 0.688430 0.040 Uiso 1 1 calc R U . . .
C9 C 0.32829(12) 0.37030(12) 0.72216(4) 0.0270(3) Uani 1 1 d . . . . .
C10 C 0.41336(14) 0.32179(13) 0.75465(5) 0.0356(3) Uani 1 1 d . . . . .
H22 H 0.451157 0.245880 0.748986 0.043 Uiso 1 1 calc R U . . .
C11 C 0.44338(16) 0.38345(16) 0.79525(5) 0.0460(4) Uani 1 1 d . . . . .
H23 H 0.500158 0.348710 0.817708 0.055 Uiso 1 1 calc R U . . .
C12 C 0.39198(16) 0.49446(15) 0.80348(5) 0.0434(4) Uani 1 1 d . . . . .
H2 H 0.414184 0.536850 0.831258 0.052 Uiso 1 1 calc R U . . .
C13 C 0.27565(15) 0.48148(13) 0.73088(5) 0.0370(3) Uani 1 1 d . . . . .
H3 H 0.216643 0.515443 0.709001 0.044 Uiso 1 1 calc R U . . .
C14 C 0.30825(17) 0.54396(14) 0.77135(5) 0.0433(4) Uani 1 1 d . . . . .
H4 H 0.272704 0.620877 0.776813 0.052 Uiso 1 1 calc R U . . .
C15 C -0.00654(13) 0.30385(13) 0.49262(5) 0.0349(3) Uani 1 1 d . . . . .
H8 H -0.044196 0.317037 0.523826 0.052 Uiso 1 1 calc R U . . .
H7 H -0.041673 0.230117 0.479210 0.052 Uiso 1 1 calc R U . . .
H9 H -0.028208 0.371131 0.472083 0.052 Uiso 1 1 calc R U . . .
C3 C 0.50929(14) 0.41495(13) 0.37358(5) 0.0357(3) Uani 1 1 d . . . . .
H17 H 0.471890 0.340220 0.385203 0.054 Uiso 1 1 calc R U . . .
H16 H 0.603653 0.406619 0.371101 0.054 Uiso 1 1 calc R U . . .
H15 H 0.473095 0.433278 0.342548 0.054 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
O1 C7 1.3441(14) . ?
O1 C8 1.4428(15) . ?
O2 C5 1.2275(13) . ?
O3 C2 1.2282(16) . ?
O4 C7 1.1977(15) . ?
N1 C5 1.3472(15) . ?
N1 N2 1.4071(13) . ?
N1 C6 1.4513(15) . ?
N2 C15 1.4509(17) . ?
N2 H10 0.874(16) . ?
N3 N4 1.4102(14) . ?
N3 C3 1.4588(17) . ?
N3 H11 0.887(16) . ?
C1 C2 1.5027(17) . ?
C1 H14 0.9800 . ?
C1 H13 0.9800 . ?
C1 H1 0.9800 . ?
C2 N4 1.3511(15) . ?
N4 C4 1.4484(15) . ?
C4 C5 1.5189(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C7 1.5050(17) . ?
C6 H21 0.9900 . ?
C6 H20 0.9900 . ?
C8 C9 1.4996(18) . ?
C8 H5 0.9900 . ?
C8 H6 0.9900 . ?
C9 C13 1.3822(19) . ?
C9 C10 1.3854(18) . ?
C10 C11 1.381(2) . ?
C10 H22 0.9500 . ?
C11 C12 1.373(2) . ?
C11 H23 0.9500 . ?
C12 C14 1.374(2) . ?
C12 H2 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H3 0.9500 . ?
C14 H4 0.9500 . ?
C15 H8 0.9800 . ?
C15 H7 0.9800 . ?
C15 H9 0.9800 . ?
C3 H17 0.9800 . ?
C3 H16 0.9800 . ?
C3 H15 0.9800 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C7 O1 C8 115.63(10) . . ?
C5 N1 N2 117.44(9) . . ?
C5 N1 C6 121.03(10) . . ?
N2 N1 C6 121.47(9) . . ?
N1 N2 C15 113.81(10) . . ?
N1 N2 H10 108.0(10) . . ?
C15 N2 H10 113.9(10) . . ?
N4 N3 C3 111.89(10) . . ?
N4 N3 H11 108.8(10) . . ?
C3 N3 H11 110.1(10) . . ?
C2 C1 H14 109.5 . . ?
C2 C1 H13 109.5 . . ?
H14 C1 H13 109.5 . . ?
C2 C1 H1 109.5 . . ?
H14 C1 H1 109.5 . . ?
H13 C1 H1 109.5 . . ?
O3 C2 N4 120.82(11) . . ?
O3 C2 C1 122.00(12) . . ?
N4 C2 C1 117.15(11) . . ?
C2 N4 N3 119.61(10) . . ?
C2 N4 C4 120.05(10) . . ?
N3 N4 C4 120.32(10) . . ?
N4 C4 C5 111.87(10) . . ?
N4 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N4 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
O2 C5 N1 122.57(10) . . ?
O2 C5 C4 122.61(10) . . ?
N1 C5 C4 114.82(10) . . ?
N1 C6 C7 112.46(10) . . ?
N1 C6 H21 109.1 . . ?
C7 C6 H21 109.1 . . ?
N1 C6 H20 109.1 . . ?
C7 C6 H20 109.1 . . ?
H21 C6 H20 107.8 . . ?
O4 C7 O1 124.20(11) . . ?
O4 C7 C6 126.34(11) . . ?
O1 C7 C6 109.42(10) . . ?
O1 C8 C9 109.23(11) . . ?
O1 C8 H5 109.8 . . ?
C9 C8 H5 109.8 . . ?
O1 C8 H6 109.8 . . ?
C9 C8 H6 109.8 . . ?
H5 C8 H6 108.3 . . ?
C13 C9 C10 118.89(12) . . ?
C13 C9 C8 123.07(12) . . ?
C10 C9 C8 118.01(12) . . ?
C11 C10 C9 120.20(14) . . ?
C11 C10 H22 119.9 . . ?
C9 C10 H22 119.9 . . ?
C12 C11 C10 120.66(14) . . ?
C12 C11 H23 119.7 . . ?
C10 C11 H23 119.7 . . ?
C11 C12 C14 119.69(14) . . ?
C11 C12 H2 120.2 . . ?
C14 C12 H2 120.2 . . ?
C9 C13 C14 120.58(13) . . ?
C9 C13 H3 119.7 . . ?
C14 C13 H3 119.7 . . ?
C12 C14 C13 119.96(15) . . ?
C12 C14 H4 120.0 . . ?
C13 C14 H4 120.0 . . ?
N2 C15 H8 109.5 . . ?
N2 C15 H7 109.5 . . ?
H8 C15 H7 109.5 . . ?
N2 C15 H9 109.5 . . ?
H8 C15 H9 109.5 . . ?
H7 C15 H9 109.5 . . ?
N3 C3 H17 109.5 . . ?
N3 C3 H16 109.5 . . ?
H17 C3 H16 109.5 . . ?
N3 C3 H15 109.5 . . ?
H17 C3 H15 109.5 . . ?
H16 C3 H15 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
C5 N1 N2 C15 -116.06(12) . . . . ?
C6 N1 N2 C15 66.78(14) . . . . ?
O3 C2 N4 N3 -176.29(11) . . . . ?
C1 C2 N4 N3 5.36(16) . . . . ?
O3 C2 N4 C4 1.83(17) . . . . ?
C1 C2 N4 C4 -176.53(11) . . . . ?
C3 N3 N4 C2 -111.59(13) . . . . ?
C3 N3 N4 C4 70.30(14) . . . . ?
C2 N4 C4 C5 -87.79(13) . . . . ?
N3 N4 C4 C5 90.31(13) . . . . ?
N2 N1 C5 O2 -171.57(10) . . . . ?
C6 N1 C5 O2 5.60(17) . . . . ?
N2 N1 C5 C4 9.09(15) . . . . ?
C6 N1 C5 C4 -173.73(10) . . . . ?
N4 C4 C5 O2 -12.53(16) . . . . ?
N4 C4 C5 N1 166.80(10) . . . . ?
C5 N1 C6 C7 -103.36(13) . . . . ?
N2 N1 C6 C7 73.70(14) . . . . ?
C8 O1 C7 O4 -0.79(18) . . . . ?
C8 O1 C7 C6 176.91(11) . . . . ?
N1 C6 C7 O4 -15.19(17) . . . . ?
N1 C6 C7 O1 167.17(10) . . . . ?
C7 O1 C8 C9 160.12(11) . . . . ?
O1 C8 C9 C13 18.09(19) . . . . ?
O1 C8 C9 C10 -163.74(12) . . . . ?
C13 C9 C10 C11 0.7(2) . . . . ?
C8 C9 C10 C11 -177.50(14) . . . . ?
C9 C10 C11 C12 -1.5(2) . . . . ?
C10 C11 C12 C14 1.0(3) . . . . ?
C10 C9 C13 C14 0.5(2) . . . . ?
C8 C9 C13 C14 178.67(14) . . . . ?
C11 C12 C14 C13 0.3(3) . . . . ?
C9 C13 C14 C12 -1.0(2) . . . . ?
 
_refine_diff_density_max    0.230
_refine_diff_density_min   -0.222
_refine_diff_density_rms    0.045



