 
data_MA_1_0m_a
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C16 H16 N2 O4 Se' 
_chemical_formula_sum
 'C16 H16 N2 O4 Se' 
_chemical_formula_weight          379.27

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'
 'Se'  'Se'  -0.0929   2.2259
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_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'
 
_cell_length_a                    5.2732(10)
_cell_length_b                    11.353(2)
_cell_length_c                    14.331(3)
_cell_angle_alpha                 105.300(6)
_cell_angle_beta                  97.375(6)
_cell_angle_gamma                 101.622(6)
_cell_volume                      795.5(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     300(2)
_cell_measurement_reflns_used      9926
_cell_measurement_theta_min        3.00
_cell_measurement_theta_max       27.09
 
_exptl_crystal_description       'block'
_exptl_crystal_colour            'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.583          
_exptl_crystal_F_000              384
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.250
_exptl_crystal_size_mid           0.190
_exptl_crystal_size_min           0.060
_exptl_absorpt_coefficient_mu     2.382
_shelx_estimated_absorpt_T_min    0.587
_shelx_estimated_absorpt_T_max    0.870
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.5333
_exptl_absorpt_correction_T_max   0.7456
_exptl_absorpt_process_details    
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       300(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'i-mu-s microfocus source'
_diffrn_measurement_device_type   
 'Bruker D8 QUEST diffractometer with PHOTON II detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             20734
_diffrn_reflns_av_unetI/netI      0.0304
_diffrn_reflns_av_R_equivalents   0.0378
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          1.919
_diffrn_reflns_theta_max          27.421
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.992
_diffrn_measured_fraction_theta_full  0.991
_diffrn_reflns_Laue_measured_fraction_max    0.992
_diffrn_reflns_Laue_measured_fraction_full   0.991
_diffrn_reflns_point_group_measured_fraction_max   0.992
_diffrn_reflns_point_group_measured_fraction_full  0.991
_reflns_number_total              3595
_reflns_number_gt                 3188
_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 APEX4'
_computing_cell_refinement       'Bruker APEX4/SAINT'
_computing_data_reduction        'Bruker APEX4/SAINT'
_computing_structure_solution     'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.0365P)²+0.2750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3595
_refine_ls_number_parameters      210
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0352
_refine_ls_R_factor_gt            0.0293
_refine_ls_wR_factor_ref          0.0726
_refine_ls_wR_factor_gt           0.0699
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.035
_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
Se1_1 Se 1.12607(4) 0.73410(2) 0.46576(2) 0.03920(9) Uani 1 1 d . . . . .
O1_1 O 0.0196(3) 0.57730(16) 0.14636(12) 0.0567(4) Uani 1 1 d . . . . .
O2_1 O 1.3315(4) 0.76582(16) 0.83937(11) 0.0550(4) Uani 1 1 d . . . . .
O3_1 O 0.3359(4) 0.75117(17) 0.16894(14) 0.0614(5) Uani 1 1 d . . . . .
O4_1 O 1.1583(4) 0.9026(2) 0.93550(12) 0.0718(5) Uani 1 1 d . . . . .
N1_1 N 0.7592(4) 0.79973(17) 0.30961(15) 0.0529(5) Uani 1 1 d . . . . .
H1A_1 H 0.909395 0.843702 0.345277 0.063 Uiso 1 1 calc R U . . .
H1B_1 H 0.677513 0.828125 0.267843 0.063 Uiso 1 1 calc R U . . .
N2_1 N 0.8227(5) 1.01121(19) 0.84520(14) 0.0586(5) Uani 1 1 d . . . . .
H2A_1 H 0.712786 1.057232 0.841744 0.070 Uiso 1 1 calc R U . . .
H2B_1 H 0.891865 1.007028 0.901578 0.070 Uiso 1 1 calc R U . . .
C1_1 C 0.7848(4) 0.63838(17) 0.38783(13) 0.0317(4) Uani 1 1 d . . . . .
C2_1 C 0.6515(4) 0.68579(17) 0.31923(13) 0.0326(4) Uani 1 1 d . . . . .
C3_1 C 0.4021(4) 0.61029(17) 0.26274(13) 0.0336(4) Uani 1 1 d . . . . .
C4_1 C 0.2968(4) 0.49405(19) 0.27723(16) 0.0405(5) Uani 1 1 d . . . . .
H4_1 H 0.132578 0.445592 0.240862 0.049 Uiso 1 1 calc R U . . .
C5_1 C 0.4315(4) 0.4508(2) 0.34394(17) 0.0460(5) Uani 1 1 d . . . . .
H5_1 H 0.359695 0.373405 0.352414 0.055 Uiso 1 1 calc R U . . .
C6_1 C 0.6746(4) 0.52270(19) 0.39858(15) 0.0406(5) Uani 1 1 d . . . . .
H6_1 H 0.765975 0.492669 0.443484 0.049 Uiso 1 1 calc R U . . .
C7_1 C 1.0160(4) 0.81691(17) 0.58374(14) 0.0340(4) Uani 1 1 d . . . . .
C8_1 C 1.1249(4) 0.80418(17) 0.67201(14) 0.0339(4) Uani 1 1 d . . . . .
H8_1 H 1.241121 0.752506 0.672283 0.041 Uiso 1 1 calc R U . . .
C9_1 C 1.0651(4) 0.86725(18) 0.76168(14) 0.0350(4) Uani 1 1 d . . . . .
C10_1 C 0.8870(4) 0.94504(18) 0.76154(15) 0.0380(4) Uani 1 1 d . . . . .
C11_1 C 0.7716(4) 0.95307(18) 0.66985(15) 0.0389(4) Uani 1 1 d . . . . .
H11_1 H 0.648870 1.001240 0.667981 0.047 Uiso 1 1 calc R U . . .
C12_1 C 0.8353(4) 0.89192(18) 0.58339(14) 0.0370(4) Uani 1 1 d . . . . .
H12_1 H 0.758026 0.900258 0.524147 0.044 Uiso 1 1 calc R U . . .
C13_1 C 0.2560(4) 0.6549(2) 0.19015(15) 0.0405(5) Uani 1 1 d . . . . .
C14_1 C -0.1394(5) 0.6177(3) 0.0771(2) 0.0686(8) Uani 1 1 d . . . . .
H14A_1 H -0.307834 0.558157 0.052836 0.103 Uiso 1 1 calc R U . . .
H14B_1 H -0.051968 0.622795 0.022954 0.103 Uiso 1 1 calc R U . . .
H14C_1 H -0.164125 0.699020 0.109260 0.103 Uiso 1 1 calc R U . . .
C15_1 C 1.1857(4) 0.8496(2) 0.85385(15) 0.0428(5) Uani 1 1 d . . . . .
C16_1 C 1.4712(6) 0.7484(3) 0.9261(2) 0.0700(8) Uani 1 1 d . . . . .
H16A_1 H 1.567267 0.685490 0.906739 0.105 Uiso 1 1 calc R U . . .
H16B_1 H 1.347261 0.721681 0.964442 0.105 Uiso 1 1 calc R U . . .
H16C_1 H 1.591938 0.826508 0.964792 0.105 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
Se1_1 C7_1 1.9269(18) . ?
Se1_1 C1_1 1.9294(19) . ?
O1_1 C13_1 1.338(3) . ?
O1_1 C14_1 1.443(3) . ?
O2_1 C15_1 1.330(3) . ?
O2_1 C16_1 1.442(3) . ?
O3_1 C13_1 1.219(3) . ?
O4_1 C15_1 1.208(3) . ?
N1_1 C2_1 1.354(3) . ?
N2_1 C10_1 1.360(3) . ?
C1_1 C6_1 1.381(3) . ?
C1_1 C2_1 1.416(3) . ?
C2_1 C3_1 1.423(3) . ?
C3_1 C4_1 1.404(3) . ?
C3_1 C13_1 1.471(3) . ?
C4_1 C5_1 1.369(3) . ?
C5_1 C6_1 1.380(3) . ?
C7_1 C8_1 1.376(3) . ?
C7_1 C12_1 1.400(3) . ?
C8_1 C9_1 1.405(3) . ?
C9_1 C10_1 1.413(3) . ?
C9_1 C15_1 1.471(3) . ?
C10_1 C11_1 1.409(3) . ?
C11_1 C12_1 1.370(3) . ?
 
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_1 Se1_1 C1_1 99.01(8) . . ?
C13_1 O1_1 C14_1 116.1(2) . . ?
C15_1 O2_1 C16_1 116.84(19) . . ?
C6_1 C1_1 C2_1 120.58(18) . . ?
C6_1 C1_1 Se1_1 119.36(15) . . ?
C2_1 C1_1 Se1_1 120.05(14) . . ?
N1_1 C2_1 C1_1 120.34(18) . . ?
N1_1 C2_1 C3_1 122.05(18) . . ?
C1_1 C2_1 C3_1 117.60(16) . . ?
C4_1 C3_1 C2_1 119.70(17) . . ?
C4_1 C3_1 C13_1 120.52(18) . . ?
C2_1 C3_1 C13_1 119.78(17) . . ?
C5_1 C4_1 C3_1 121.15(19) . . ?
C4_1 C5_1 C6_1 119.69(18) . . ?
C5_1 C6_1 C1_1 121.27(19) . . ?
C8_1 C7_1 C12_1 118.94(17) . . ?
C8_1 C7_1 Se1_1 118.45(14) . . ?
C12_1 C7_1 Se1_1 122.59(14) . . ?
C7_1 C8_1 C9_1 121.67(18) . . ?
C8_1 C9_1 C10_1 119.36(18) . . ?
C8_1 C9_1 C15_1 119.44(18) . . ?
C10_1 C9_1 C15_1 121.19(18) . . ?
N2_1 C10_1 C11_1 119.18(19) . . ?
N2_1 C10_1 C9_1 123.04(19) . . ?
C11_1 C10_1 C9_1 117.78(18) . . ?
C12_1 C11_1 C10_1 121.84(19) . . ?
C11_1 C12_1 C7_1 120.35(18) . . ?
O3_1 C13_1 O1_1 121.5(2) . . ?
O3_1 C13_1 C3_1 125.4(2) . . ?
O1_1 C13_1 C3_1 113.06(18) . . ?
O4_1 C15_1 O2_1 121.5(2) . . ?
O4_1 C15_1 C9_1 125.4(2) . . ?
O2_1 C15_1 C9_1 113.03(17) . . ?
 
_refine_diff_density_max    0.286
_refine_diff_density_min   -0.427
_refine_diff_density_rms    0.058



