 
data_MA_2_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       orthorhombic
_space_group_IT_number            18
_space_group_name_H-M_alt         'P 21 21 2'
_space_group_name_Hall            'P 2 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, -y, z'
 '-x+1/2, y+1/2, -z'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    9.2080(17)
_cell_length_b                    19.174(3)
_cell_length_c                    4.5051(7)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      795.4(2)
_cell_formula_units_Z             2
_cell_measurement_temperature     300(2)
_cell_measurement_reflns_used      9901
_cell_measurement_theta_min        4.25
_cell_measurement_theta_max       26.33
 
_exptl_crystal_description       'plate'
_exptl_crystal_colour            'gold'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.584          
_exptl_crystal_F_000              384
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.310
_exptl_crystal_size_mid           0.270
_exptl_crystal_size_min           0.090
_exptl_absorpt_coefficient_mu     2.382
_shelx_estimated_absorpt_T_min    0.525
_shelx_estimated_absorpt_T_max    0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5175
_exptl_absorpt_correction_T_max  0.7454
_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             31206
_diffrn_reflns_av_unetI/netI      0.0197
_diffrn_reflns_av_R_equivalents   0.0396
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -24
_diffrn_reflns_limit_k_max        23
_diffrn_reflns_limit_l_min        -5
_diffrn_reflns_limit_l_max        5
_diffrn_reflns_theta_min          2.124
_diffrn_reflns_theta_max          26.519
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.984
_diffrn_measured_fraction_theta_full  0.984
_diffrn_reflns_Laue_measured_fraction_max    0.984
_diffrn_reflns_Laue_measured_fraction_full   0.984
_diffrn_reflns_point_group_measured_fraction_max   0.986
_diffrn_reflns_point_group_measured_fraction_full  0.987
_reflns_number_total              1638
_reflns_number_gt                 1559
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.646
_reflns_Friedel_fraction_max      0.989
_reflns_Friedel_fraction_full     0.991
 
_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)+(0.0321P)²+0.0983P] 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_abs_structure_details
;
 Flack x determined using 590 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.048(5)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          1638
_refine_ls_number_parameters      106
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0246
_refine_ls_R_factor_gt            0.0227
_refine_ls_wR_factor_ref          0.0586
_refine_ls_wR_factor_gt           0.0577
_refine_ls_goodness_of_fit_ref    1.095
_refine_ls_restrained_S_all       1.095
_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
Se1_1 Se 0.000000 0.500000 -0.01288(6) 0.05571(16) Uani 1 2 d S T P . .
O1_1 O 0.4516(2) 0.58670(10) 0.6233(6) 0.0644(6) Uani 1 1 d . . . . .
O2_1 O 0.4004(2) 0.67990(10) 0.8964(5) 0.0594(5) Uani 1 1 d . . . . .
N1_1 N 0.1411(3) 0.74012(12) 0.8255(6) 0.0569(6) Uani 1 1 d . . . . .
H1A_1 H 0.074240 0.770324 0.860472 0.068 Uiso 1 1 calc R U . . .
H1B_1 H 0.225758 0.745059 0.903517 0.068 Uiso 1 1 calc R U . . .
C1_1 C 0.2180(2) 0.63405(11) 0.5759(5) 0.0352(5) Uani 1 1 d . . . . .
C2_1 C 0.1132(3) 0.68466(12) 0.6472(6) 0.0412(6) Uani 1 1 d . . . . .
C3_1 C -0.0256(2) 0.67733(14) 0.5216(7) 0.0501(6) Uani 1 1 d . . . . .
H3_1 H -0.097368 0.709681 0.567704 0.060 Uiso 1 1 calc R U . . .
C4_1 C -0.0573(3) 0.62355(15) 0.3325(6) 0.0504(7) Uani 1 1 d . . . . .
H4_1 H -0.149732 0.620377 0.250351 0.061 Uiso 1 1 calc R U . . .
C5_1 C 0.0464(3) 0.57362(13) 0.2613(5) 0.0416(6) Uani 1 1 d . . . . .
C6_1 C 0.1830(3) 0.58009(12) 0.3813(5) 0.0374(5) Uani 1 1 d . . . . .
H6_1 H 0.253869 0.547599 0.331431 0.045 Uiso 1 1 calc R U . . .
C7_1 C 0.3628(3) 0.63687(13) 0.7144(6) 0.0416(6) Uani 1 1 d . . . . .
C8_1 C 0.5942(3) 0.5864(2) 0.7597(12) 0.0905(14) Uani 1 1 d . . . . .
H8A_1 H 0.643575 0.543867 0.710177 0.136 Uiso 1 1 calc R U . . .
H8B_1 H 0.584209 0.589776 0.971304 0.136 Uiso 1 1 calc R U . . .
H8C_1 H 0.649393 0.625412 0.687870 0.136 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 C5_1 1.924(2) 2_565 ?
Se1_1 C5_1 1.924(2) . ?
O1_1 C7_1 1.327(3) . ?
O1_1 C8_1 1.450(4) . ?
O2_1 C7_1 1.214(3) . ?
N1_1 C2_1 1.357(3) . ?
C1_1 C6_1 1.394(3) . ?
C1_1 C2_1 1.406(3) . ?
C1_1 C7_1 1.473(3) . ?
C2_1 C3_1 1.404(3) . ?
C3_1 C4_1 1.369(4) . ?
C4_1 C5_1 1.389(4) . ?
C5_1 C6_1 1.375(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
C5_1 Se1_1 C5_1 100.11(14) 2_565 . ?
C7_1 O1_1 C8_1 115.4(2) . . ?
C6_1 C1_1 C2_1 119.8(2) . . ?
C6_1 C1_1 C7_1 120.2(2) . . ?
C2_1 C1_1 C7_1 120.0(2) . . ?
N1_1 C2_1 C3_1 119.3(2) . . ?
N1_1 C2_1 C1_1 123.1(2) . . ?
C3_1 C2_1 C1_1 117.6(2) . . ?
C4_1 C3_1 C2_1 121.3(2) . . ?
C3_1 C4_1 C5_1 121.1(2) . . ?
C6_1 C5_1 C4_1 118.4(2) . . ?
C6_1 C5_1 Se1_1 121.5(2) . . ?
C4_1 C5_1 Se1_1 120.09(19) . . ?
C5_1 C6_1 C1_1 121.7(2) . . ?
O2_1 C7_1 O1_1 121.7(2) . . ?
O2_1 C7_1 C1_1 124.7(2) . . ?
O1_1 C7_1 C1_1 113.6(2) . . ?
 
_refine_diff_density_max    0.234
_refine_diff_density_min   -0.170
_refine_diff_density_rms    0.038



